2088: It's A Sissy World free porn video

2088: It's a Sissy World Charles Pauline - Data Processor Cindy Pauline - Charles' wife Ms. Miriam Jensdotter - Charles' Boss James Marie - Charles' work friend Ms. Marysdau - James' boss Creampuff - A Sissy Store Worker Babykins - A Sissy Store Worker Suzi - The Sissy Store Owner Butterscotch - Creampuff's Roommate Supervisor Gabriellez - Creampuff's Apartment Supervisor Janice and Roger - Passengers on the Looper Ms. Hardcastle - Milking Salon Director Nurse Hamilton - Milking Salon Receptionist and Associate Director Missy Chambermaid - Milking Salon Worker Jacob - Sissy Store Administrator Introduction Recently married, Charles and Cindy move to Chicago to start a new life together. But it's 2088 and the world has changed such that Women now occupy most management and political positions. Charles struggles as a data processor in the big city under a dictatorial boss who enjoys doling out harsh punishments for minor infractions. Charles can handle the spankings. It's when his punishment includes Sissy clothing that things begin to spin dangerously out of control... Year 2088 Chapter 1: A New Job "Good luck on your first day!" Cindy gave me a quick hug and kiss and then propelled me to the bus with a playful swat on my bottom. "You too, honey!" I watched and waved as she stepped into a waiting car-share and was whisked away. I used my heads-up to find the bus (10 blocks walk) to the looper which took me downtown. Fresh from college and just moved to Chicago, it was the first day at work for both of us. Cindy had landed an associate's position at a top-10 law firm, while I was joining the Data Processing pool for CICI (Computer Information Centralized, Incorporated). Like most wives, Cindy would be making about 10 times my salary, but she still felt it was important that I 'be useful' as a man and make my own money. I was grateful for my DP assistant's job. It was a plum position for any man fresh out of community college. I vowed to do the best I could to make myself indispensable. "You've been assigned to Ms. Jensdotter," said the nice man at reception (call me 'Mike!'), walking me to my desk. "She's... um... one of our most respected managers!" The office floor had all of the Data Processing (DP) assistants in an open area, surrounded by manager's offices with windows. I was led to the far side of the room to a desk just outside of an expensive looking, dark-wood door that had 'Ms. Jensdotter' carefully stenciled on it. "Here are your tablets," Mike said. "If you need a glove controller you can get one from the IT cabinet over there. Use your chip to open it, but anything you use will be deducted from your pay. Understand?" "Yes, Mike, I understand. Thanks." I looked around the room. The rest of the men (and the two token women) in the DP pool were filing in, each setting up their tablets and logging in. Open floor plans and centralized DP pools were the latest trend. Gone were the days of working at home with flexible hours. Management wanted you working together in the open so they could keep an eye on their DP resources. "You're the new man, I guess." I looked up at a tall, stern, well dressed woman in a suit-skirt. "Yes, Ma'am," I said. "What's your name?" "Charles Pauline, Ma'am." "Well, I hope you last longer than the last five," she said. "I swear, you men are so useless! You take days to do even the simplest of correlations and then the work is sloppy. You're not useless like those others, are you?" "No, Ma'am!" "Well, we'll see. Now take these clothes to the cleaners, it's one block south, and then on your way back, get me a grande latte, two extra shots, skim." "Yes, ma'am," I accepted the bag of dirty clothes from her and hurried out of the office. My new job had started! As I walked to the cleaners, the day seemed especially wonderful. The sun was out, the air was fresh and I couldn't stop smiling. I was so happy to have my job! I would do anything to keep it. * * * "My office, Mr. Pauline." Ms. Jensdotter's loud, angry voice projected from my tablet. I blushed as the men around me looked over. Could I be in trouble? I entered Ms. Jensdotter's office and carefully closed the door behind me. "How may I be of service?" I asked. "Here, Mr. Pauline." I walked to Ms. Jensdotter's side. "Do you see a problem?" she asked, gesturing to the tables and statistics displayed on her desk display. "No... ma'am?" I was honestly confused. It was just the data processing she had asked for. "Validate," she called out. "** Five records failed. Within statistical error. **" "Five records failed." Her acid tone made it clear that I had committed a grievous error. "I will not accept such sloppy work, Mr. Pauline. Understand?" "But... but..." I was flummoxed. They taught us in school not to overdo the analysis. Tracking down and fixing every last record was generally a waste of resources. "It's within statistical error. Those five records will not affect the outcome." Ms. Jensdotter bolted out of her chair and slapped me hard in the face. "I WILL NOT TOLERATE BACK TALK!" She towered over me. "Errors build up! Five records today will be five hundred tomorrow. The reason why this company is so well respected is that we have 100 percent completeness and 100 percent accuracy. You are expected to track down and fix every last record. Otherwise, why wouldn't I have a computer do it? Do we understand each other, MISTER Pauline?" "Yes, ma'am!" I cried, feeling horrible. "Yes, I promise, Ma'am!" "Hold out your hands." "Ma'am?" "I said, HOLD OUT YOUR HANDS!" Frightened, I did as instructed, feeling vulnerable. "Palms up." I watched as Ms. Jensdotter fetched a thin, whippy cane from her desk. The vicious looking shaft was the same thickness as my little finger. "I know it's fashionable to use more high-tech methods," she said, "you know, collars, bracelets, embedded neurological stimulators, social shaming... But I prefer the old-fashion methods. Five strokes - because it's your first transgression. Hold still, and keep quiet. Take it like a man." With a swish and a meaty *thwack*, she sliced the cane across my palms leaving a stripe of pain that made me jerk my hands hands away. I did my best to stay quiet, but I couldn't help a small yip of pain. I stepped away from her, my flight instinct engaged. "Get back here," Ms. Jensdotter hissed. With shaking knees, I stepped back into place. "Palms out!" she barked I revealed two bright-red line segments which connected when I held my hands together. I felt a tear drip down my cheek. "Take your punishment like a man," she said. "Because if you don't... well we both know what that means, don't we?" Of course I knew what that meant, but I held it in. Don't say it! Don't even think it! Because once it's out there... I steeled myself for more punishment. What followed was four more strokes, each one criss-crossing my palms, each leaving an angry red welt. By the time she was done, I was openly crying. "There, there," she said, pulling me into a hug and holding my head to her chest and stroking the back of my head. "You men are so emotional. It's just a little punishment for bad work. It's nothing that you didn't agree to in your employment contract." "Y-y-yes, Ma'am," I said, wiping away my tears. "M-may I g-go now?" "Not until you speak your transgression, apologize, humbly promise to do better in the future, and then thank me for taking the time to correct you." I gulped. This would be hard. "I... I... I'm sorry for not correcting the five failed records--" I started. "And for not consulting me about if they should be fixed," Ms. Jensdotter interrupted. "Now start again." My face burned with humiliation. "I apologize for not consulting you about what to do with those five failed records," I said. "And I apologize for not correcting them so that you would have a 100-percent clean data set. I promise--" "Humbly promise." "I *humbly* promise to do better in the future. Thank you, Ms. Jensdotter...." I paused and took a deep breath. "Thank you for taking the time to correct me." "You may go." As I left the office, the entire room stopped work to look at me. Half of them looked at me with pity. The other half had a haughty 'you-got-what-you-deserved' look. * * * For the rest of the day, I fumed - angry and humiliated. 'How dare she talk that way to me!' I told myself. And the patronizing looks from the rest of the staff was even worse. I was just doing my job! Just like I had been taught at DPCC (Data Processing Community College)! You are not supposed to worry about those last few records - not when doing a large statistical aggregation! It's just a waste of money! But instead I just sat meekly at my desk and continued working through my assigned tasks, doing my best to hide the red stripes on my hands which burned like hot coals. This couldn't possibly be legal, could it? Maybe my wife Cindy could check my contract? She was a lawyer, after all. She would be able to help. I took one of my 10-minute government mandated bathroom breaks to run my hands under some cold water. "My name is James." I looked up at a stick thin man with shaggy hair and a friendly, freckled smile. He gave me a quick hug from behind. "I saw what happened with you and Ms. Jensdotter. She can be..." I saw him struggle to come up with a politically correct term. "... a very demanding boss," he finished. I dried my hands and we walked out of the bathroom together. "Appropriately demanding, of course!" James added. But I could tell from the way he had frozen his facial expression, that he meant the exact opposite. He was being careful because all of our conversations are computer and video monitored at work. But that was no different than at DPCC, so naturally we were both adept at speaking one thing out-loud while communicating the opposite with our eyes. "Charles," I said. "It's a pleasure to meet you. Is it okay if we don't shake hands?" I showed him my hands with the five red stripes. "Oh!" James gasped. "Of course! I just wanted to say, if you ever need any advice or help around here, just let me know. I've been here for over a year now, so I think I know what's what." "Thank you, James," I said, honestly grateful. We hugged and kissed each other on the cheek, and then touched our wrists together to exchange our contact info. * * * "She's within her rights," said Cindy. "How is that possible?" I asked, appalled. "It's standard for DP assistant jobs," Cindy explained, showing me the clause in my employment contract. "Ever since the right to waive your rights was established by the Supreme Court, most DP assistant contracts, like yours, require that you waive your rights to fair and equal treatment. Yours is a bit unusual in that you waived your right to Bodily Integrity as well. Did you mean to do that?" "But... but... that's not fair!" I sputtered, outraged. "I had no idea what that would lead to!" "Oh, honey, I realize that you're just a naive young man, but welcome to the real world. This is how it works." How I hated how she would talk to me in that patronizing manner! I have a two-year community college degree! I graduated at the top of my class! I'm not like one of those construction grunts. "You have to see it from the company's perspective," Cindy continued. "The government has mandated that humans must fill these jobs, they can't be automated. You know, like construction jobs, truck drivers... you know. Of course, that's horribly unfair for the company, especially since the jobs are mostly filled by lazy men who just goof off all day long." "Not all men are lazy!" "I know, pookums. You're definitely not lazy. That why I love you so much. But a lot of men *are* lazy. I see it all the time. Welfare Johns on the dole, living off their government check, spending the money on weed. It's disgusting." She grimaced, like smelling something foul. "My point is," she continued, "companies are not allowed to automate these jobs. It's prohibited by the government, and that's a huge burden on these companies." "Did you waive your rights?" "Oh, hell no!" Cindy laughed. "No woman would ever waive their rights. We don't need to." "Well, that's just sexist!" "Oh please," Cindy rolled her eyes. "You men are all alike. How many times do I have to tell you - it's not based on your sex, it's based on your job. Is it women's fault that most men end up in these menial low paying, government mandated jobs? No! That's just the way it works." "It's not fair." "Now, don't pout," Cindy said, teasingly, giving me a kiss on my tightly clenched lips. "After all, men don't pout. You know who pouts?" "Yes," I sulked, knowing full well what she was referring to. But her statement worked, and I stopped pouting and forced myself to smile. "That's my boy," Cindy said, cooing to me. "Now, I need you to promise me that you will stay at your job and do everything that Ms. Jensdotter expects of you. Can you do that?" "Yes, Cindy. I'll do my best." "Charles, you need to do better than that! Remember, Mother pulled some serious strings to get you that job. It's an excellent position for a man of your training. For any man, in fact." "I understand," I said. "I need you to be a model employee. After all, your work also reflects on me and Mother. Now do you promise to do everything Ms. Jensdotter asks you to do?" "Yes, Cindy, I promise," I said, feeling defeated. "That's my good boy." Cindy gave me a hug and a kiss on the head. "Now, when's dinner?" * * * The weeks went by quickly as both Cindy and I settled into our respective jobs and I gradually got our apartment organized. Cindy's job was going great. She'd been accepted by the other partners at the law firm and was impressing her clients. She'd was also put in charge of managing the office renovations, which she seemed to enjoy. I worked as diligently and as carefully for Ms. Jensdotter as I could, occasionally working extra hours in the evening or morning to make sure my work was accurate. The extra effort paid off, because she found only two very minor mistakes. One a misspelled field name and a single data value which was off by a small percent. I suspected she was using a automated validator to double-check my work. Whatever. That was her right. Anyway, both of those infractions were punished with two strokes across my palms. After a couple of weeks of error free work, I began to feel like I could handle the job. And the other parts of the job weren't too bad. Once a week I would have to take Ms. Jensdotter's laundry to a special service, and then pick it up when they were done. Also she had me get her coffee twice a day and once she had me take her niece to the museum for the afternoon. The niece was a real brat (I swear, every new generation of women are getting more and more obnoxious and overbearing). She whined the whole time, telling me that being a man from the DP Pool made me "not worthy" of being her escort, demanding that I carry her book bag everywhere and making me buy her snacks (which I had to pay for out of my own money - *sigh*). James and I often ate lunch together and occasionally our breaks would line up. I would have liked to spend more time with him after work, but we both had wives to take care of (and wives come first, as the saying goes). "Everything okay, James?" "Oh, yes!" James said covering his wince with a forced smile. "My boss, Ms. Marysdau? She... um... found a mistake in my work, for which I am terribly sorry. I am so grateful that she took the time to give me corrective actions," he winced again, "and put me on remedial training. Isn't it wonderful to have bosses that take such good care of their DP staff to make sure that we are all operating at the highest possible level?" Of course, I could tell that James was lying through his teeth. There was nothing overt, of course, but if you're a man whose been through DP college, you can tell these things. Fortunately, women and computers don't seem to be nearly as good at reading men's facial expressions as other men. "I completely agree," I said, giving James' hand a quick squeeze. "I know that corrective actions can be difficult at times, but they make us better employees and better men, and for that I'm grateful!" We then went on to talk about more mundane subjects, but all the time James was squirming in his seat. What had his boss done to him? * * * "Now don't be mad," Cindy said, as we were slipping into bed one night. "Why shouldn't I be mad?" Cindy hesitated. "Mom enrolled you into a new training program," she explained. "'House Husband's Handbook for the Happy Home.'" "WHAT? Cindy!" I said, exasperated. "I know perfectly well how to take care of a home and how to take care of my wife! My father taught me well!" "I know, I know!" At least she had the decency to look sheepish about it. "She just wants the best for her daughter. I told her you don't need it, but she insisted. So, if you don't mind...?" I sighed. "Fine," I said. Immediately a note appeared on my heads-up with the new program. "The things I do for you!" "I am so lucky to have you," Cindy said. "I just want you to know how much I appreciate how hard you're working to make our home a comfortable retreat." I blushed and stammered a 'thank you,' and then willingly submitted as she pushed my head between her legs. She sighed as I licked and pleasured her 'down there', which I was happy to do, because, you know... wives come first. "Oh yes," she moaned, "I am a *very* lucky wife." * * * Chapter 2: A Major Mistake Something was wrong. After lunch with James, I felt the stares as I walked through a sea of DP workers to my desk. They looked at me with sick fascination. And pity. And eagerness to take my job. Oh sure, all of the men in the DP pool pretend to be nice and cooperative and we kiss and hug and say 'thank you' and 'you're welcome' (after all, Big Company is always listening, right?). But the truth is we're all back-stabbing bitches inside, hoping for the other to fail so we can take over. There are few opportunities for men to advance, so those that do arise are attacked like piranha on raw veal. As soon as I got to my desk, I saw the reason for the stares . My tablets were all flashing a **SEE ME IMMEDIATELY**, note from Ms. Jensdotter. "Shit," I muttered, quickly following it up with "I do so hope I haven't disappointed Ms. Jensdotter! If so, I do so hope that she will accept my sincerest apologies." After all, you never know when your statements might help with the review board, so it's always best to leave a trail of verbal good intentions wherever you go. I picked up my stenotab, knocked, and entered Ms. Jensdotter's office, closing the door behind me. Ms. Jensdotter was working and didn't look up. From my training I knew better than to interrupt. So I stood there, patiently waiting for her to acknowledge me. After about fifteen minutes, I indicated the door and asked, "Would you rather I come back later?" "Don't you *dare*," Ms. Jensdotter growled. Chastened, I stood still, getting more freaked out by the second until finally, after a good thirty minutes she finally stopped working and looked up. She flicked something on her screen and my tablet beeped. "See anything wrong with your analysis on X3242?" I looked at my tablet and flicked through the data. I knew it well, and I thought I had done a solid job of organizing the content. Then I went back to the original request, where I saw a statement circled by Ms. Jensdotter. I had missed an entire column of data! 'Oh shit, oh shit, oh shit...' the words ran through my head as I felt my stomach drop like a stone. This was a MAJOR error which meant that the entire dataset was broken! Of course, fixing it would only take a few minutes, but this was more than a misspelled field name. If this had gotten to the customer (whoever that was, I still wasn't entirely certain who our customers were, since all of the datasets were hashed and anonymized for security) then it would be a major black eye. "I am *so* sorry, Ms. Jensdotter!" I said, my heart racing. I felt sweat break out on my forehead. "I don't know how this happened! I always double-check the DWO, but somehow I must have missed that last sentence. I promise, I will triple and quadruple check all work orders from now on!" But Ms. Jensdotter just looked at me, her stare boring into me, making it clear how displeased she was. "Of course I have to note this in your public record," she said. With another flick she sent an 'Official Public Notice of Negligent Performance' which popped onto my tablet. "Sign there and see that you do better next time." "No!" I cried, impulsively rushing to her desk. "Please Ms. Jensdotter! I can't be 'Noticed'! My... my wife would see it! And m- m-my m-mother-in-law! They would be so disappointed... please!" OPNs came in a variety of shapes and forms, but the OPN-NP was the worst. It was an official flag on your public record that would stick with you forever. All it took was three and I'd be fired and never get another DP job again. With an OPN-NP on my record, the only jobs I could get would be low-level construction jobs - manual labor, basically, and I did *NOT* want that. "Please," I pleaded. "I'll do anything to avoid a 'Notice'. Isn't there some way I can make this up to you? Please?" Already I was tearing up. "Men," Ms. Jensdotter snorted. "You all feel you're entitled to a government mandated job, don't you? No need to work. No need to be useful. Just show up and who cares? Is that it? So what if you get fired, isn't that right? You'll just go out and live off your welfare check. You *disgust* me!" "Ms. Jensdotter, please," I pleaded, tears streaming down my cheeks. "And here, Charles, I thought you were different. Your Mother-In-Law, Rose, called me and assured me that you were a hard worker and careful about everything you did. But look at this. Such an *obvious* error. I shudder what to think if the computer hadn't caught your mistake." "Please, Ms. Jensdotter. Please." I laid myself and my future bare before her. Ms. Jensdotter just sat there, staring at me. Until finally, I saw her open the bottom drawer of her desk. My heart leapt with hope, until I saw what she had fetched. It was a much larger cane. "RC monitor off," she said. There was a beep from the room computer. This cane was at least 2 feet long and had a shaft which was as thick as my thumb, with a leather grip on one end. "Pull down your pants and lean over the table," she commanded. "Underwear too." I walked over to the table, it was a small but solid rectangular hardwood table used for meetings, and did as instructed. The office air conditioning was cold on my bottom. "Now, I hope you appreciate this," she said, fetching two more items from her desk drawer. "Open up." I opened my mouth and Ms. Jensdotter shoved a rubber ball into it. It just fit. "That's to protect your teeth, and muffle any sounds you might make." Next she took a leather strap and tied my wrists together behind my back. "And that's to keep your hands out of the way. And now, I believe that we are ready for your punishment. Twenty strokes." What followed was so excruciating I almost lost my mind. Each stroke across my bottom raised a bright red welt and an explosion of pain. I bit down and screamed into my gag and jerked against the table, sobbing and drooling. The strokes continued at a measured pace for an enormously long time. Each one followed immediately by a hot flash of pain making me spasm and cry out, the pain blossoming in the seconds which followed, searing into my brain, as Ms. Jensdotter waited for its full effect before delivering the next one. By the time she was done, Ms. Jensdotter was breathing hard with the exertion. "Stay there," she said, "and don't move." My bottom was radiating and pulsating with a searing blaze. The agony so intense I felt broken. I sobbed so hard that tears puddled on the table beneath me. Behind me, I heard some fabric on fabric sounds. "So hot," she murmured, as I felt her hand trace the angry red stripes on my bottom, causing me to tremble. "Oh yessss..." The hand disappeared, and I couldn't tell what was happening, until I heard a long sigh. After another second, Ms. Jensdotter released my arms and pulled the rubber ball from my mouth. I moved to get up, but she pushed me back down, pressing my face into the pool of drool and tears on the table. "Stay down until I tell you to get up," she said. Ms. Jensdotter walked back to her desk. When she returned, I felt her pulling at my underwear, then something cold and metallic? And then cutting! "There, you may get up now." She had cut away my underwear! What the fuck?! "You won't be needing these anymore," she said, throwing the remnants of my grey cotton briefs into the trash can. I was so astonished that I couldn't think of what to say. Imagine, your boss - cutting off your underwear? I hid my penis as I turned around to face her, naked and exposed, but I didn't dare pull up my pants until she told me to. "Don't get too comfortable," Ms. Jensdotter said. "I still haven't decided if I should post your Public Notice or not. RC: James Marie." "Yes, Ms. Jensdotter?" The voice of James came out loud and clear from the room speakers. "Come to my office, James. Out." Oh god no. Not James! I felt my face turn bright red with shame. Ms. Jensdotter looked at me for a long time, with something halfway between a smirk and a glare. As the seconds stretched out, I began to shiver in the cold. There was a beep. "James Marie," the room computer announced. "Have him wait," Ms. Jensdotter said. "Yes, Ms. Jensdotter," the RC responded. "Isn't there something you're forgetting, Charles?" Ms. Jensdotter asked, after another minute of staring at me. Damn. Yes, there was. "I apologize for not including the required field into the data set," I said, looking at the ground. "I realize that was a grave error. I humbly promise to do everything in my power to prevent the problem from ever happening again. Thank you for taking the time to correct my transgression." "Very good," she gave me a thin smile. "Charles, I have decided to *not* submit the Public Notice." "Oh, thank you Ms. Jensdotter!" Relief flooded over me. "BUT ONLY IF," she continued, "you agree to one more corrective action." "Yes, Ms. Jensdotter. Anything, Ms. Jensdotter." "You will be on probation for a fortnight. During that time, to make sure you fully understand the seriousness of your infraction, you are to wear sissy panties underneath your regular clothes." "Sissy Panties?" I gasped. "But I'm not a--" I stopped short. As everyone knows, the absolute, unbreakable man's rule Number 1 is: You never, ever (not ever!), say 'I am not a sissy.' Because as soon as you say that, you have basically admitted that you *are* a sissy, because only a true sissy would ever have to say that. "Yes, Charles?" Ms. Jensdotter looked at me, her eyes piercing. She knew exactly about rule #1, and how close I had just come to breaking it. "But I'm a man," I said. "I wear men's clothing." "Who knows?" Ms. Jensdotter said, her voice cutting deep. "Maybe you'll come to enjoy wearing sissy panties." Her implication was clear. If I came to enjoy sissy panties, then I would be classified as a sissy. And that must *never* happen. I shuddered at the thought. My life would be ruined. Worse than ruined, destroyed. "Never," I said. "Then you have nothing to fear, do you?" she said. "If you hate them so much, then wearing them for a week will simply be a distasteful chore. Regardless, wearing Sissy Panties is my final corrective action for your latest transgression, do you accept?" "Yes, Ms. Jensdotter. Thank you, Ms. Jensdotter," I said humbly. "And you'll be monitored," she added. "And if we discover that you secretly enjoy wearing them..." She let the words hang in the air. The implication was clear. "I won't," I stated, definitively. I wouldn't let myself enjoy them. Not ever. "RC, let James in." James walked in the door and his look of pity at seeing my red and blotchy eyes, runny nose, and pants down around my ankles made me wish for a hole to open up in the ground and swallow me up. I hung my head, wondering if I could ever again look James in the eye. "You may pull up your pants." I frantically reached down and pulled up my pants, almost getting my penis caught in the zipper as I tucked in the shirt tails. It felt strange wearing pants with no underwear and everything just flopping around in the coarse fabric. "James? Take Charles shopping for Sissy panties. He'll need enough for a fortnight's probation. I think you know the drill," Ms. Jensdotter smirked. "Yes, Ms. Jensdotter," James replied. "That will be all." * * * Chapter 3: The Sissy Store James and I walked to the Sissy Store down the street from the office, about a block away. These days, there are dozens of Sissy Chains around the country, so there's almost always one nearby. Since James and I couldn't talk openly, we had to speak in code. "I'm sorry you have to go through this," James said, "but I know you'll be a better person once it's all over!" He said this with as much enthusiasm as he could, for the monitors. During the business hours the company monitors your lens video and tympanic audio, even outside. "I'll let you in on a secret," James said, stopping me. "Ah... are you sure?" I asked, looking around, as if there might be a company spy watching. "I'm wearing Sissy Panties right now." James pulled out the waistband of his pants and showed me a glimpse of pink silk inside. "Oh, James!" I held a hand over my mouth. "Yeah, I know," he shrugged. "I made a huge error last week. I was caned, just like you. Apparently, a fortnight in sissy panties is a new punishment that the women managers have thought up." James paused, then realized he should add a positive spin on the statement. "And I think it's an excellent idea!" he added. "After all, we all need to learn the consequences of our actions, don't you agree, Charles?" "Oh, yes, James," I said, agreeing with him, while at the same time thinking how horrible it was. "And my Manager, Ms. Marysdau, she's just absolutely the best," he continued. "She said we have nothing to fear. If we are truly men, wearing Sissy Panties will not affect us. After a fortnight, our punishment will be over and we can go back to wearing regular men's briefs, and no one will be the wiser." James didn't say anything more about what would happen if the Sissy Panties actually did affect us, for down that road exist possibilities too horrible to say out loud. No, I needed to focus on the fact that I was a man, through and through, and no amount of wearing Sissy Panties could ever change that. But when we rounded a corner and I saw the Sissy Store, a lifetime of schoolyard taunting, bullying and prejudice took over. "I can't!" I cried, running into an alley, out of sight. Ever since I was in elementary school, boys teased boys about having sissy tendencies. Just a glance at a Sissy Store was all it took to earn a day's worth of merciless verbal abuse. "Charlie, looking at the Sissy Store!" one of my friends would tease. "Betcha wanna go visit, dontcha, Char-lee? Betcha wanna go there and let them take *real* good care of you, dontcha, Princess Char-lee? Princess Char-lee girl? Princess Cherry? Sweet Princess Cherry?" I had pretty rotten friends back then, I now realize. I got into fights all through elementary school, trying to prove my manliness. All someone had to do was to call me "Princess Cherry" or "S.I.T." (Sissy In Training) and I would lash out. I spent more time in the principal's office than in the classroom. "I think you're overcompensating," my Mom would say, whenever I came home from a fight, bruised or cut. I didn't understand what she meant at the time, but I do now. Finally it got to be too much and I was expelled. "Oh Charles," Mom said, when she picked me up that day. "You don't need to fight to prove you're a man. It's not what's outside that's important. It's who you are the inside." From that day forward I was home-schooled, and with the calmer and more regimented home environment (Mom was a former Admiral in the Navy), I settled down and actually began to enjoy my studies. By the time I was ready for DP Community College, I had become a much more respectful, level-headed person. But turning that corner and seeing the Sissy Store, and knowing that I was actually supposed to go into it (!) made it all come back. All that childhood teasing, all of those tears and lashing out. "I can't! I just can't!" I cried, pressing against the wall. I could practically hear the chants of my obnoxious elementary school friends crying 'Cherry's an S.I.T.! Cherry's an S.I.T.!' "Charles, you don't have a choice!" James tried to counsel me. "You have to do this, or you will lose your job and get 'Noticed' for sure!" "I can't, I just can't," I looked at James with wild eyes. "Listen," he hissed at me, grabbing me harshly by the arm. "Stop this! This is your punishment and you have to take it. There is *No Choice*, do you understand? Now pull yourself together and start acting like a MAN, goddamn it! Take your punishment like a MAN!" He was right, of course. This sort of quivering behavior is probably just what they were looking for! I could practically hear Ms. Jensdotter saying: 'Interesting, I think he protests too much!' 'Shit. Charles!' I yelled at myself inside. 'Snap out of it! Calm yourself!' Finally, I was able to control my breathing and stand up straight. "That's better," James said, releasing my arm. "Now remember, take it like a man." "Like a man," I repeated to myself. "Like a man." This mantra would be my shield. "Like a man. Like a man..." * * * "Welcome To Suzi's Sissy Store! It's Cotton Candy Pink Week!" said two bright and smiling Sissies as we stepped into the store. James and I were visually assaulted by an onslaught of PINK. All of the surfaces of all of the walls and counters were a light pink color ("Cotton Candy Pink!") with 'pink on pink' pictures of lollypops, hard candy wrappers, soda pop, gummy bears, jelly beans - all moving. And the smell! Lavender and baby powder and roses... suffocatingly strong. it felt like diving into a pink ocean and breathing pink until it filled you up. The store itself was stuffed overflowing with racks and racks of an overwhelming array of clothing of all kinds. In the center of the store was a large, queen-sized bed, with a pink tulle draped headboard, a bed skirt draped with layers and layers of pink ruffles, pink ruffled pillows, and a ridiculous pink comforter covered in rows and rows of pink fabric flowers. Off to one side, in the baby-sissy area, was a white painted wood, adult-size crib. It was tall, with a ruffled pink skirt around the bottom, and two mattresses (pastel blue polkadot and pink princess) and a white with pink bunnies crib bumper with pink ribbon trim and pink ribbon ties that circled the inside. The main Sissy in charge (Suzi, presumably, wearing a closely tailored professional-looking pink suit with a white silk blouse) clapped her hands twice, and immediately two Sissies appeared from behind a screen and surrounded us with their shiny pink satin and frills. Each was wearing outrageously sissy dresses, overflowing with bows, lace, ribbons, and petticoats, pink satin opera gloves, light pink stockings and pink ruffled socks with white and pink ribbons. Their faces were made up Sissy-style, with pink iridescent eye shadow, pink lips, and exaggerated pink rouge making them look like they were permanently blushing with embarrassment. "Mademoiselle Jamee!" the Sissy called 'Babykins' cried out. "You're back! We're so happy! Do you need some more sissy panties? Maybe a sissy training bra? Ma petite amie?" "Ah, no!" James said, backing away. But Babykins was having none of that! She grasped hold of his hand and forcibly pulled him to the center of the store. "I'm just here for Charles! That's all! I don't need any more sissy things! Definitely not!" The other sissy grasped my hand to her chest and looked at me, eyes wide with a solemn and sincere expression. Because of her pink satin gloves, flouncy pink satin and lace dress, my immediate reaction was that my hand had been pulled into a silk and satin quicksand which might eventually devour my whole body if I didn't escape! I desperately tried to pull away, but she held me firmly to her body. "My name is Creampuff," she said, looking directly into my eyes with an unsettling intensity. "What is your name?" "Ch-Charles," I stammered, trying again to disengage my hand, but failing. "Ah! Mademoiselle Charlie!" she repeated. "Are you looking to become a Sissy? It would be so wonderful if you were, then we could be Sissy friends! And there is no better, more true and loving friend than a Sissy friend! Would you like to become a Sissy and be my Sissy friend?" "No!" I said quickly. I looked at Jamie... Sorry *JAMES*, with shock and horror. This was so much worse than I was expecting! "Are you here shopping for your own Sissy?" Creampuff asked. "Tell me all about her! I'm sure I can become *her* Sissy friend, if you'll just introduce us!" "No... not that... either..." I was having a hard time forming words and sentences. "Well, if you're not here shopping for you, and you're not here shopping for your Sissy, then who are you shopping for, Mademoiselle Charlie?" Creampuff asked, batting her eyes with feigned innocence. She pulled me closer and now I was enveloped by her perfume, a potent rose and lavender combination which closed around me like I was drowning. I looked at James for help, but he just looked back and shrugged as if to say: 'go ahead and tell her'. "I need to buy some Sissy Panties..." I said. "EEEeeee!!" Creampuff's squeal was high-pitched, uninhibited and painful to my eardrums. "I LOVE shopping for Sissy Panties! That's just about my most favorite thing in the world! But who are the panties for??" "They're..." I looked around and at James again, but he just looked away. "They're for me," I admitted, finally, hanging my head. "I'm being forced to wear them as punishment by my boss. But that does NOT mean I'm becoming a Sissy! I'm a MAN. This is just temporary!" "Oooh! Another 'punishment' Sissy! That's becoming very popular these days! Lots of bosses are making their staff wear Sissy Panties as punishment. Sometimes more! Well maybe it won't be punishment for you! You never know... you might like it?" "Never!" I said, a little too loudly and a little too harshly. I jerked my hand violently away from her. "Creampuff and Babykins understand," Babykins said, reaching over and stroking my back. "Poor, nervous boysie-woysies," somehow, she was able to hug both James and me at the same time, "so concerned with their manhoodies! Ooh!" She looked down at our crotches and made an 'O' with her mouth. "But sometimes," Babykins whispered into my ear so that only I could hear, "it's not your choice. Sometimes it's just destiny." I pushed Babykins roughly away. "Please stop," I pleaded. "I just need to buy some Panties and get out of here, as quickly as--" "And put them on," James interrupted. "You have to buy them and put them on. You need to wear them back to the office." "*And put them on,*" I said through gritted teeth. "Please, or we'll go to some other store." "I'm so sorry," Creampuff said, both of the Sissy's dropping to their knees, their heads bowed. "Sometimes, Creampuff and Babykins come on too strong too fast. Can you forgive us?" I rolled my eyes, exasperated. Did absolutely everything have to be so dramatic? "Fine," I said. "I forgive you. Can I just buy a pair of panties now?" "Of course," Creampuff hopped up. "Let's just measure you." "Do I have to be measured?" I whined. "I usually buy a men's medium." "Of course we have to measure you!" Creampuff said, approaching me with a tape measure. "Please," I whined. "My waist is 30-inches. There. Isn't that enough?" "Men's sizes and Sissy sizes have nothing to do with each other," she explained. Creampuff dropped to her feet. "Please, Mademoiselle Charlie. I *have* to measure you, it's my job. I have to do it or I'll be punished. And not in the nice way. Please, please, please..." She looked up at me with sad, doleful eyes. For a second I worried she might actually start crying. "Okay... fine," I relented. "YAAY!!" Creampuff jumped up. "Mademoiselle Charlie? Here, I'll help you take your shirt out of your pants!" "Out here? In the open?" I looked around wildly. "I can't do that!" "MISTER Pauline," said Suzy, the professionally dressed shop owner, with a disdainful tone. "There is no dressing room here. Sissies just undress right here in the store." "But... But..." I looked around. "James?" I pleaded, but James was pretending to be intensely interested in something in the far corner. "I would just like to add, MISTER Pauline, that should you cause poor Creampuff here more distress, I would need to lodge a complaint with your owner," she paused significantly, "or wife." A lump in my throat, I scanned the room, hoping for some sort of lifeline but found nothing I could hide behind. After minute, my shoulders slumped, and I held out my arms. With an exited squeal, both Babykins and Creampuff quickly undressed me, leaving me standing naked in the store. Worse, because my briefs had been cut off by Ms. Jensdotter, my crotch and bottom were fully naked. A red flush gradually spread over over my whole body. "Oh, Charlie!" Creampuff touching the red stripes on my bottom. "Creampuff has something for that," she whispered in my ear, disappearing behind the screen and returning a moment later with a small jar of some creamy ointment which she proceeded to rub over my bottom. "Thank you," I said gratefully, feeling the burn and itch subside. I saw my buns in the mirror and was surprised to see the red welts start to fade. "You keep it," she said, handing the jar to me. "It will reduce bruising as well. Babykins?" Creampuff tried to sound efficient but couldn't help the girlish giggle in her voice. "Please take down these measurements." Creampuff first measured around my waist which was smaller than I realized. Her satin gloved fingers gave me weird goosebumps as they caressed my bare skin. She then measured around the widest part of my hip, and then at the top of each leg, slithering a hand between my legs and then measuring the diameter right at the crotch. "Someone's having fun," she whispered, giving me a sly look as she rubbed the back of her hand against my hardening member, almost as if by accident. "NO," I said, jerking away. 'What the fuck is wrong with me?' I chastised myself. My data processor mind kicked in and I realized that the iterations were becoming unstable. 'SHIT,' I realized, 'if this keeps up...' "Hmmm..." Creampuff just hummed and finished measuring each of my inseams, one hand working its way deep into my crotch as she did. "That's enough!" I stepped away. "Are we done??" "We're done," Creampuff said, bashful. Quickly I snatched up my pants to put them on, but I was stopped by Babykins. "No, no!" she said. "Otherwise, you'll have have to take them off again. Here, wear this robe instead." She helped me into a ridiculous shimmery silk robe trimmed with white marabou feathers. It settled and stroked sensuously over my naked body. Once it was on, Babykins ran her hands down the robe, ostensibly to make it drape correctly. "Enough," I pleaded, as she ran her hands over my bottom. "Sorry," she said, not sounding sorry at all. "Okay, so now the best part! You get to choose what panties you want!" Creampuff jumped up and fetched a large tablet. James and I were both pulled to the center of the store and pushed onto the bed. James and I were pushed together and then surrounded by our two Sissy guides like a big slumber party, all of us looking at the large tablet Creampuff was working. "Please," I pleaded. "I just want the simplest pair of panties I can get." "Oh, YUCK," Creampuff pretended to gag. "We can't sell you those! We really can't." "Why not?" "Because," Babykins explained, "those can only be bought by owners who want to punish their Sissy's." "Oh. Okay." That made no sense to me. I looked pleadingly at James. "How about the same panties I bought?" James asked. "Okie dokie!" Creampuff made a few motions and I was looking at James' panties on the screen. It was also duplicated on all the surfaces in the store as well as if we were floating in a virtual cloud of panties. "Let me show you!" Babykins bounced off the bed and rifled through the racks, returning with a pink Sissy Panty that was delicately trimmed in a lighter pink around the legs and waist. "That's what you're wearing?" I asked, shocked. I looked over at James, who gave me an embarrassed shrug, and then looked away, his face coloring. "Ohhh, Jamie, you're blushing!" Babykins said. "Just like a Sissy would! It's sooo adorable!" "Please stop," James said. "Isn't there something with less... uh... lace?" I asked. "Well... I guess..." Creampuff said, clearly not happy. She flipped the image on her tablet to a different pair of panties. These were essentially the same, but the lace was the same color as the panties and also a bit thinner and more discrete. "But you don't want that," Babykins said. "Yes, I do," I said, defiantly. "I'll buy them." "No, you really don't," Creampuff tried to stop me, but I was already working my way out of their nest and trying to get up. "Please, Charlie, let me show you some other options!" "Charles," James said, putting a hand on my arm. "They're not Sissy enough." "What do you mean?" "Ms. Jensdotter will see them and just send you back to get a more Sissy pair." "How do you know? Are you sure?" James looked away for a second and then back at me. "Yes, I'm sure," he said. "Because that's what happened with me and Ms. Marysdau. I got sent back twice before she accepted my purchase." Shit. I looked at the Sissies who were both nodding their heads in agreement with James. "Okay, fine," I said, finally. "Then just give me the exact same panties that James bought. Ms. Jensdotter can't complain about that, can she?" "Makes sense," James said. "Are you really really sure?" Creampuff said, with such sadness in her voice. "We have thousands and thousands of Sissy Panties! I usually spend hours looking for just the right style! I'm really good at it!" "No! Please!" I shouted, but then regretted it as Creampuff shrank back. "I, ah, need to get back to work. Please, uh... Creampuff, I just want to buy the exact same type as James bought. Please." "Well... okay," she said, flipping to the 'buy' screen. "I just need your credit account." She held out the tablet and I touched it with the back of my wrist. "Why's it paused?" I asked. That never happened before. Transactions usually went through immediately. "I know why!" Babykins smirked. Just as the screen flashed 'transaction on hold' I got a beep in my ear and Cindy appeared on my heads-up. "Charles?" "Oh! Cindy!" I said, shocked, looking around the store, frantic. "What in the *world* are you doing in a Sissy store? Is there something you need to tell me?" "What? NO! No! It's just..." I looked around frantically, trying to think of a good excuse. But it was impossible. Even if I could, I would be betrayed by my biometrics. So now Cindy would have to know. "I'm sorry, Cindy. I made a mistake at work today, and as part of my punishment, uh... um... Ms. Jensdotter is making me wear Sissy Panties. But just for a fortnight! I'm so sorry!" "Oh.... interesting," she said, giving me not at all the reaction I was expecting. "I'll have to call and ask her about that. The other managers at my office have been talking about doing the same for our DP staff. There's this new management philosophy going around. But Charles, shame on you for making such a grievous error! Ms. Jensdotter is quite right to punish you so severely! I'm surprised you didn't get Noticed. She must be a very tolerant manager to let you off with just wearing sissy panties for a fortnight. Unless you received some other punishment? Did she punish you in some other way, Charles?" "I was also caned," I whispered, blushing. But even though I whispered, everyone on the bed could hear me. Creampuff and Babykins both looked at me with understanding. Now they understood where the red stripes on my bottom came from. "How many strokes?" "Twenty strokes," I said, embarrassed. "Ah, well, that explains it then," Cindy said, probably referring to biometrics or alarms she probably received. "I approve. I hope you took your punishment like a man?" "Yes, Cindy," I thought about how I had blubbered and cried the whole time. "Good for you," Cindy snorted in a way which let me know that she could probably tell I was lying. "Now let's see about these Sissy Panties, which ones were you going to buy? Show me. That's some Sissy Store, by the way! I've never seen the inside of one before." "Creampuff?" I asked. "I need to see James' panties again." "Who is James?" Cindy asked. "Oh... he's uh... a colleague at work. He's being punished in the same way." Hearing this, James gave me a 'what the fuck?' look, embarrassed to be called out. He turned away, making it clear he didn't want to be seen. "Oh! So you've found a playmate at work! Oh, Charles, I'm so happy for you! Is he there? Can I see him? I mouthed a 'sorry!' to James, and then turned to look at him. My lens camera capturing his half-grimace / half-smile as he waved to my wife. "Tell him I said 'hello', and I hope that he and his wife can join us for dinner some day." "My wife, Cindy, says 'hello' and she's inviting you and your wife to dinner some day," I said. "Oh, ah..." James blushed (much to Babykin's delight). "Thank you, Mrs. Pauline. I will ask my wife tonight but I'm almost certain she would be delighted." "Wonderful!" Cindy said. I smiled and nodded gratefully to James. "Now are these the panties?" she asked, as I looked towards Creampuff who was holding up the panties I had selected. "Oh, Charles, I'm not sure they look Sissy enough. Is there anything Sissier?" I gulped. "Sh-she wants, uh... my wife wants something... more Sissy." I tried to communicate with my eyes to Creampuff, 'Please! Tell her there's nothing more Sissy!' but Creampuff just squealed with delight and began flipping through panties which I was forced to look at. "Such a wide variety!" Cindy enthused. "So many shades of pink and so much lace! I like these with the rows and rows of overlapping lace. But I heard that some Sissy Panties have a... I don't know what it's called, a sleeve? For your little peenie, Charles. Do they have any of those? Ask them, Charles!" "Please... Cindy... do I have to...?" Creampuff could sense my distress and gave me a hug, her satin hand squeezing my bottom a little too intimately. "It will be okay," Creampuff whispered in my ear. "Charles, I'm only doing this for your own good. Do you want to be constantly told to wear Sissy lingerie as punishment?" "No! Of course not!" "Well, then, if we demonstrate to Ms. Jensdotter that you can wear the most Sissy pair of panties possible and take it like a man, then don't you see? She will give up on punishing you this way. Trust me, show her how you have purposefully selected the most effeminate pair of Sissy Panties possible, and then after a fortnight you'll be free of them forever." "But... but... what if..." I stuttered. I was feeling trapped and panicky. "What if..." "What if what?" Cindy prompted. "Charles! Speak up! What are you concerned about?" What if I can't take it? I wanted to say. What if... I find them to be... But I couldn't complete the sentence - not even in my mind. It was too dangerous. "Nothing, Cindy," I said, finally. "Of course you're right." "Yes I am. Now ask your new Sissy friends if they can show us something with a sleeve for your peenie." "She wants to see..." I took a couple of deep breaths to settle my heart, "a pair with a sleeve... for my... p..." but I couldn't get out the last word. Men had cocks or penises or hard, throbbing rods, they most certainly *didn't* have peenies. Only Sissies had peenies. "Your what?" Babykins asked. "What does she want a sleeve for?" "My peenie," I said, finally, my face flushing bright red. 'God, I wonder what my biometrics are showing now,' I wondered. I looked over at James who looked shocked but sympathetic. "Oh!" Creampuff gasped, delighted. "Oh! Oh! Such a WONDERFUL idea! Oh, you will so *love* a sleeve! There's nothing that makes a Sissy feel so cosseted and special all day long as a nice grasping sleeve! We have lots!" Creampuff quickly pulled up a number of varieties, and after another 10 minutes of excruciating review, Cindy was finally satisfied. "Perfect," Cindy said, with satisfaction. "You go ahead and buy them and I'll approve the purchase. And make sure you get Creampuff to show you how to wear them properly. Do you understand, Charles?" "Yes, Cindy." "Very good. Now I want you to buy seven pairs, okay?" "Seven pairs?" I gasped. "Yes, dear. One for every day of the week," Cindy said, as if I were a dummy not to know that. "Yes, Ma'am," I only used 'Ma'am' when I felt particularly like a husband under my wife's firm hand. "That's my obedient hubby," Cindy said. "Now I need to go. Give Creampuff my thanks." I looked at the final selection with despair. It was a delicate shimmery light pink color, with gathered stitching that would caused it to run up into and cup my bottom cheeks. But that wasn't the worst part. The worst part was that there was not only a sleeve (the peenie sleeve), but also a sack underneath, for my... "Num nums," Creampuff said, out-loud, seeing where I was looking. My god! Did she have to say it so loudly? I closed my eyes in anguish. When would this torture end?? And then, to make it completely obvious, the sleeve had a tight circle of lace at the base... around the num-nums sack... and then one more around the head of the peenie with a bit of elastic to hold it in place. "This is *such* a special pair of Sissy Panties," Babykins said, her voice hushed with admiration. "I wish I had this pair! Oh, I hope my owner will buy me these some day," she said wistfully. "Me too," Creampuff said, her eyes wide and her voice in awe. I tapped my wrist on the tablet to pay for the purchase and this time it went through without a hitch. "Would Charlie like to buy some more Sissy underthings? A bra? Some bloomers? Some Sissy Stockings?" Babykins asked. "Or Jamie! Would you like your own pair of Charlie's panties? Don't they look delicious?" "No!" James said much too quickly and loudly, looking disgusted. "Definitely not." Babykins continued the hard sell, showing James and me all of the latest Sissy Styles while Creampuff went to the back to fetch the first pair which was just finished by the Robot Seamstress. Seeing it in person was much worse than on the tablet. The peenie sleeve was flat-out vulgar, it looked like some weird sea creature worm with ribs that would swallow up my most sensitive organ. The lace was more prominent than I realized. And worse, the inside was double-lined. "Two layers of the most silky satin fabric for your sissy bottom," Creampuff pointed out. "Now Charlie, let's put this on while the others are being sewn." Babykins pulled James over to a love-seat in the corner of the store where she continued to browse through Sissy clothing with him. James, embarrassed for me having to change in the middle of the store, became suddenly interested in what was on her tablet. "Now, let's try this on," Creampuff said, reaching to unfasten the belt of my robe. "No!" I said, backing away and holding the robe shut. "I'm sure it's fine. You measured me, right? I'l... ah... just take them and change in the bathroom at work." "But Charlie," Creampuff said, looking at me with those same sad eyes. "When you buy more than one, you have to try it on before the others are manufactured. After all, I could have made an error with the measuring tape." Creampuff placed one hand on my arm, holding the panties with the other. "Please," she said, her eyes intense and sad in their over-done pink sissy makeup. I hesitated. The store was currently empty except for James and me. "Okay." "Thank you." Creampuff unbelted my belt and slipped the robe off me. I was now fully naked. She then knelt before me and held out the panties. I stepped in them and then Creampuff slowly, very slowly, pulled the panties up my legs. I got goosebumps as they traveled up my legs. I felt my nipples tingle as she pulled them, slowly, every so slowly, over my hips. I felt my breath catch in my throat as she pulled them snug around my ass cheeks and 'peenie'. "What are you doing?" I gasped, as Creampuff reached through the sleeve in the front of the panties. With two satin-covered fingers, she grasped the tip of my penis and then slowly (did she have to go quite so slow??) pulled it through the sleeve until the head of my peenie was exposed at the end. "It sticks out," I gasped. "That's the way it's designed." "What? You mean--" "Oui, Mademoiselle Charlie," Creampuff smiled. The end of the sleeve had a small amount of white lace and wide light pink satin ribbon which went around my penis that Creampuff tied with a bow. She then made sure my balls were in the 'num num sack' and tied a (much wider) shiny pink satin ribbon around that too. "I... I can't!" I groaned. My parts were all on display and mostly surrounded by shiny pink nylon, lace and ribbons. "Oooh, look! Mademoiselle Charlie's peenie is swelling!" It was true. The Sissy panties were stroking and grasping at my most sensitive parts. The gathered nylon satin bottom worked its way between my butt cheeks, like an intimate embrace. The sleeve was narrow and double lined with soft, silky satin as well, stroking my shaft. Worse, it felt better and better the harder I got! The collar around the head of my peenie was caressing sensuously that spot right underneath my little peenie helmet. And my balls were being constantly clutched and grabbed at by the num-nums sack. Just then, an older matronly looking woman entered the store, dragging her own sissy, a simpering bit of whiny fluff, behind her. "Looksies!" Creampuff called out. To my horror, everyone in the store looked over! "Oh, they're so adorable!" Cried Creampuff. "Jamie, shouldn't we buy you a pair as well?" "No!" Jamie said, horrified. "Oh, those *are* adorable panties!" Said the matronly woman. She walked over, dragging her sissy with her to come see the panties. The Sissy in her high heels and ridiculously high girls party dress scrambled to keep up. "They're new," said Suzi, the manager, walking over as well. Now I was surrounded by women and sissies, all staring at my panties. "From the 2088 fall 'Prissy' line of undergarments." I desperately tried to cover myself up with my hands, but at a snap of the manager's fingers, Creampuff grasped my hands and pulled them behind me, forcing me to stand still and be exposed to all of these strangers. "Look, Baby June!" See how all of her little Sissy parts are so nicely presented!" The matronly woman reached out and ran her manicured fingers over my shaft in the peenie sleeve, and then grasped my num-nums in the num-num sack. "And the fabric is so soft and luxurious." I groaned. Her fondling was making my peenie hard, which was making the sleeve tighter and even more stimulating! If only Cindy hadn't put me on that strict orgasm schedule, then I'd could to the bathroom and relieve myself. But ever since she caught me masturbating in the shower, I was on orgasm lock-down and Cindy would be immediately alerted to any transgression by my biometrics. "Do you remember your vows, Charles?" She had asked. "You promised to obey. Every time you masturbate without permission, it's like you're cheating on me and breaking your sacred wedding vows. Remember that." This mean that there was nothing I could do but grit my teeth and bear it. And so here I was, being fondled in a pink, heavily scented Sissy store wearing a pair of stimulating panties and struggling to hold it all in. 'Hold it in, hold it in!' I muttered to myself. Finally, the matron's inspection was over. "We'll get three pairs for my son," she declared. "Pink, yellow, and light blue." The Sissy next to her squealed in alarm, but could do nothing as he was dragged away to shop for something else. "Please, may I put my pants on now?" I begged. "Of course, Mademoiselle Charlie," Creampuff said. Unfortunately, I was not allowed to dress myself as both Creampuff and Babykins dressed me, tucking in my shirt and fastening my pants, all the while "accidentally" stroking me in all sorts of intimate places. By the time I was fully dressed, my peenie was as hard as stone and I had to stand still and take a few deep breaths to get myself under control. "I have to get out of here," I whispered to James, feeling desperate. "I know," he whispered back. "I can could see that." "The rest of your panties are ready," said Suzi, the owner, holding up a bright pink shopping bag. It had light pink tissue paper sticking out of it and it said "I'm a Suzi's Sissy!" on the side. And I would have to carry this out in public?? "Bye bye, Mademoisselle Jamie! Bye bye, Mademoisselle Charlie!" Babykins and Creampuff both called out. But before we could leave the store, the owner stopped us. "Would you like to leave a tip?" she asked, holding up her tablet. On the display were pictures of Babykins and Creampuff with suggested tip amounts. James and I looked at each other. "Okay," we both said, tapping our wrists to the display. * * * The walk back to the office was quiet, both James and I lost in our own thoughts. I did my best to hold the bag so that no one could see it. As I walked, I was constantly reminded of my new Sissy panties. The two layers of slippery fabric moved around my bottom sensuously with every step. Worse, I could feel my satin encased peenie moving as it slipped in and around the ruffles. The bow around my num nums and the bow around the hood were both constant reminders of what I was wearing. "It's only for two weeks," James said. "Yeah." Somehow that statement was not as reassuring as it should have been. We both looked at each other, then hugged and parted for our workstations. Of course, I had to endure the snorts of derision from the DP assistants who saw my pink "I'm A Suzi Sissy" bag. ** Come immediately into my office ** said the red flashing note on my tablet when I arrived. I looked around and saw the rest of the DP pool look at me with pity. "Mister Pauline are you wearing Sissy Panties?" Ms. Jensdotter asked. "Yes, Ms. Jensdotter." "Look me in the eye." I looked up at Ms. Jensdotter, who was looking back at me with an intense expression. "Yes, Ms. Jensdotter?" "Now tell me... Charlie, what are you wearing for underwear?" She had never called me 'Charlie' before. How much of my time at the Sissy Store had she monitored? "Ms. Jensdotter, I am wearing..." the words stuck in my throat. "Sissy Panties," I finally got out. "Show me." I was just about to ask, 'Do I have to?' but the expression on her face made it clear that there was no room for discussion. And so I unbuckled my pants and pushed them down to my ankles. My peenie in the sleeve popped out as if to say 'hello' in all of its lace and ribboned glory, half swollen. "Oh, how darling!" Ms. Jensdotter cried out, eyes wide. "I had no idea you would take to this task so enthusiastically, Charlie!" Ms. Jensdotter got up walked over to me to get a closer look. "Ms. Marysdau had to send James back three times before he got a pair that were Sissy enough." She stroked her hands across my bottom and then went around front, cupping my num-nums. "My wife helped to pick them out," I explained, only slightly bending the truth. "She thought, um, that a more Sissy pair would better demonstrate how much of a man I am." "That only works if you don't end up liking them, of course," Ms. Jensdotter said, a predatory flicker in her eyes. She looked me right in the eye as she lightly grabbed my peenie between two fingers and then slowly pulled along the sleeve, from base to tip before finally letting go. I sucked in my breath. "Yes, Ma'am," I agreed, desperately trying to control my passions. I had to keep my feelings under control or my entire punishment period would be a disaster! "Pull up your pants and get back to work," Ms. Jensdotter said, smacking my bottom before returning to her desk. "Yes, Ma'am. Thank you, Ma'am." "Charlie?" Ms. Jensdotter said just as I was about to leave. "Yes, Ms. Jensdotter?" "You look good in Sissy Panties." "Uh..." I flushed five shades of red. "Thank you, Ms. Jensdotter." * * * Chapter 4: A frustrating week Oh My God - The fucking sissy panties! The rest of the day at work was torture. The panties kept stroking around my buns and the peenie sleeve kept me bothered all day long. Every break I had, I would run to the kitchen, fetch a glass of ice water, then run to the bathroom. Sitting on the toilet (panties at my ankles), I would pour the ice water over my hard peenie to make it go down. Even then, it was hit or miss. Sometimes, even ice water wasn't enough. I tried just pulling the panties on, without using the peenie sleeve, but then I got a note on my heads-up: 'use of sleeve required, notification will be sent to owner unless corrected in 100 seconds, 99, 98, 97. . . '. That meant, of course, that the panties were wired with sensors for proper usage, like a lot of clothes these days, and that their data was flowing through my account. That further meant that Cindy would be able to see the data streams if she wanted. So... fuck. I had no choice but to put them on properly, which meant that, invariably, my peenie was already hard again before I pulled my pants back up. Shit! If that weren't bad enough, the sleeve held my peenie at odd angles, especially when I was stiff (which was practically all the time). This mean the head and the balls, which were both exposed, would be pressing against my pants, getting rubbed as I sat or walked. It also meant I was constantly adjusting things since my peenie was constantly getting trapped at odd angles. The peenie sleeve was obviously not designed to be worn with pants. This made me wonder if it would work better if I were in a ... ... but no! 'Get back to work, Charles!' I would scold myself. 'Get back to work now! Stop thinking about your peenie sleeve!' But then, a few minutes later, I would shift in my chair and there it would be again, poking against my pants, begging for relief. I wondered if I might not make it. What would happen if I orgasmed at my desk chair from wearing an overly intimate pair of panties? I would get a public notice for certain. And Cindy would be horrified if I orgasmed without her permission. I could already hear her voice in my head, "A major violation of your wedding vows of devotion and obedience to your wife," she would say, reciting my vows back to me, the same vows which were written into the wedding contract I had signed. I just needed to get home. Get home and then I could take off the damn panties and get some relief. Get home and then I could have sex with my wife, Cindy, and take care of my problem. * * * "No sex, and the panties stay on." I stared at Cindy, dumbfounded. "But Cindy--" I whined. "No buts! Charles, I'm still very angry at you for your mistake at work. If this is the punishment your boss, Ms. Jensdotter, has decided for you, then this is the punishment that you will have at home, for disappointing your wife." "But Cindy, I..." "But what, Charles? We just had sex yesterday. You should be fine, at least for now. Are the panties making you *excited*? Are you getting nice and hard wearing them? Is that your problem? Are you worried that you might have an *accident* in them?" I looked at her, shocked. Then I remembered that she could monitor my data feed which included my full biometrics. Probably she could tell exactly how I was feeling and how my body was reacting. I blushed with shame. "No," I said, being petulant. "I'm not worried about that." "Good. Because you know who loves wearing Sissy panties, don't you?" I toed the ground. I knew *exactly* who loved wearing Sissy panties. "That's not me," I said, avoiding the dreaded word. "Well then, prove it. You only have to control yourself for fourteen days. Two weeks and then your punishment will be over." * * * Fourteen days! How would I ever manage it? I sat at my desk the next day struggling, again, to hold my passions at bay. The previous night with Cindy had been worse than torture. It had been excruciating. At Cindy's insistence, I had gone to bed naked except for my Sissy Panties which had to stay on. All night the damn panties had stroked my passions. Several times I had to go to the bathroom and take a cold shower just to settle down. If Cindy was awake, she would insist on giving me another "good-night kiss," which usually meant she would lay on top of me, her firm female body clad in a slinky nightgown pressed against my body, as she gave me a deep kiss before returning to her side to go to bed. The kisses were nice, but I wondered if she did them on purpose to keep me all riled up all night long. But somehow I had done it. I got through the night. Another cold shower in the morning and I made it to work. "Lunch?" James asked, stopping by my desk. "Yes, please!" I jumped up. "I'm having such trouble controlling, uh, my 'natural proclivities'," I said as we ate our sandwiches. "This is torture!" "I know," James agreed. "I'm on edge almost all day long, and my panties are like normal men's briefs compared to yours! I have no idea how you've managed even one day." "Of course the punishment is fair and just," I added, for the corporate monitors. "Oh, absolutely!" James agreed, although I could see in his eyes that he actually thought it was awful and unfair. "As weak men, we need to learn to control ourselves, don't we?" "Oh, yes, absolutely," I agreed, with as much fake wholehearted enthusiasm as I could manage. "But what are we going to do?" James asked. "The panties are constant stimulation. I'm afraid that my will is slipping." "Mine too," I agreed. "About the only time I can forget I'm wearing them is..." I looked up at James, eyes wide. "What?" James asks. "About the only time I forget that I'm wearing them is when I'm doing data science," I said, with sudden realization. "Oh... interesting." * * * With a fervor that would have put a New Women's Party poll worker to shame, I devoted 150% of my energy to my job. Every spare second of every day suddenly became a second which I could use to think about data science. I began to obsess about the tools I used, going carefully through every last predictor and correlation statistic and running them all on whatever dataset I had on hand, experimenting and testing until I understood every last flag and parameter. I made myself obsess about the data. I would process and reprocess it eight or nine times before I was completely satisfied I understood it. I would try random non-linear combinations just to see what might produce a better correlation. I would download public data sets and mash them up with the data in various random ways, just to see what popped out. At home and on the looper, I sat with my tablet for hours re-reading my old data science textbooks, re-learning the concepts and re-doing the exercises. Then I bought new, advanced textbooks and started plowing through those too. Feedback neural networks, pruned random forests, hybrid combinations, all manner of data analysis, pattern recognition, and meta correlations went through my voracious study. I experimented with everything on dozens of test data sets, analyzing them from all dimensions until I felt I understood each and every algorithm completely before moving on. And it worked! During the day, my passions were kept at bay. I would go through a cycle of action -> feeling -> reaction. I might move in some weird direction, then the panties would pull on my peenie or run up my bottom, distracting me, and then immediately I would turn to whatever data science project I was currently working on and attack it with even more focused attention. After a week, I began to feel like I might make it. The only problem occurred at night... * * * Cindy and I were relaxing in bed, reading and snuggling before turning out the lights and going to sleep. I had just taken a long cold shower, so I was soft... for now. At Cindy's insistence, I was naked except for my Sissy Panties while she was wearing one of her fancier nightgowns. Recently, Cindy had re-invented her wardrobe, replacing all of her college clothes with items that were more upscale, professional and woman-powerful. Wool tailored suits, pantyhose (yes, they made a comeback), high quality blouses with starched white collars, and high heels. This was unfortunate because strong women dressed in strong clothing has always been a sure way to get my passions fired up. Once Cindy upped her wardrobe, she would come from work, looking sharp and put- together, and it would be so bad that I would have to immediately jump in the shower and turn it on full-cold. Or I would quickly fetch my tablet and study some intricate paragraphs on 5-fold cross correlation. What was worse is that she started teasing me with her body! She would stroke me and press against me. Our physical intimacy was at least double what it was previously. But even though I begged and begged, she refused to have sex until I was no longer wearing Sissy Panties. "I can't think of you that way when you're wearing those panties," she would say. Or, "you need to prove that you can control yourself, like a man." Or, "honestly, Charles, I would think that a true man would actually want sex *less* after wearing sissy panties all day. Being a true man, you must really hate them, I'm sure. I'm surprised you want sex at all, how disgusted you must be with those silky and soft lace fabrics stroking your most intimate parts all day long." "Well then, let me take them off!" I begged. "Let me wear my male underwear at home, please. And then I'll be the man you married, and we can have sex. *Please* Cindy." "I've already told you, Charlie, that you need to wear your Sissy Panties 24x7 until your punishment is over. Only then can you really convince Ms. Jensdotter that you've done your time and that you are a true man. That's why I've taken all of your male underwear and locked them away in the safe. There can be no backsliding. Just prove to her that you're 100% man and that no amount of wearing Sissy Panties will change you, and then she'll back down. I'm sure of it." I had to admit that her logic was sound, but it sure felt like a bad idea. But now that my male underwear was all locked away, I was stuck with wearing my Sissy Panties with their ridiculous bows, satin and lace everywhere I went, even on the weekends. Every time I sat down I would feel my bottom slide on the layers of shiny fabric. * * * As we relaxed in bed, Cindy reached over and stroked my panties, feeling the satin and lace. "I've never thought about owning a Sissy before, but I'm starting to understand the appeal," she said. "I'm NOT a Sissy!" I said, angrily, then immediately cursed myself, realizing that I had said the dreaded phrase, the phrase which no man should ever need to say. Damn it! Of course I blamed the panties. Even with my focus on data science, it was impossible not to think of the sissy panties and sissies in general about a million times a day. "Of course not, Charlie," Cindy said, placating me. "I know you're all man, and you know you're all man. And when your two week period is over, Ms. Jensdotter will also know that you're all man. I'm just saying that seeing you in these panties... well it's made me wonder what owning a Sissy might actually be like." "Wh-what do you mean?" I asked, nervous. "I thought I was taking care of the house well enough?" "Of course you are," she cooed. "You're amazing. Dinner was super yummy, and I'm ever so grateful that you've taken over all of the laundry and cleaning. It just that, as my husband, well there are just some things I can't discuss with you. Some things I would never ask you to do." "And you could discuss them with a Sissy? You could do these things with a Sissy? But Cindy, I thought you and I had no secrets from each other!" "And we don't. It's just that... well there are certain feminine feelings and situations that I could never discuss with a real man, Charlie. That's all. You're wonderful around the house, and I really, really appreciate that, but there are just some things which I would never ask you to do because I respect you too much, you know, as a man. It's not because you're not a good husband and most definitely not because you're not my soul mate. I guess I just realized that having a Sissy servant might... have some advantages, that's all." "Harrumph," I said, sitting back, feeling nonplussed. "I don't know why I can't be all those things for you. I don't understand why you feel the need to bring someone else into our household." "Now I never said that! All I said was that I can now understand the appeal, whereas I never had before. Come here, sweetie." Cindy held out her arms and after putting up a token resistance, I succumbed and crawled into her embrace. My head nuzzled her breasts as she stroked me. "Women are just complex, demanding creatures," Cindy said. "Tell me about it!" I replied, with mock exasperation. Cindy laughed. "I promise you that I will never bring some other Sissy into our household." "Thank you, Cindy." We lay like that for a while. "Hey!" I squirmed. "Why are you always feeling up my bottom?" "I can't help myself," she said. "Your buns are just so yummy in those panties!" I squirmed some more under her playful caresses. My god I was hard! And the Sissy Sleeve on my peenie made it at least 100 times worse. "*Please* can we have sex?" I begged for about the millionth time. "When your punishment is over." * * * "Hey, there. You're a man, aren't you?" He looked like a college student. His earnest expression was framed by glasses and sandy hair. He held up tablet. "We're looking for volunteers for the Jacobsen campaign," he explained. "Bump here to be put on the list." "Why would I want to help Jacobsen?" I asked, taking a step backwards. "He wants to get rid of the government mandated jobs." "Exactly! They're holding us back, man. Don't you see? Government mandated jobs are low-level, low-skill positions. They are mostly filled by men, right? But they are our chains! They are a crutch. They are limiting our true potential! Look at how well Women are doing! They hold 89% of management and professional jobs and 99% of the wealth of this country! Men have become second class citizens!" "But I need my job!" I stepped back, horrified. "If it's no longer mandated, they'll just get a computer to do it and then I'll have nothing! What the hell will I do then??" "We're men! We'll think of something. We'll invent new jobs. We'll compete with women for management jobs. You know, men used to run the world!" "The world's changed," I spat out, walking away. But his words entered my brain and I started to wonder. The elections were coming up. I knew who Cindy was going to vote for, Anna Womansfield of the 'New Women's Party". She had been cajoling me to join her for months now. The New Women's party was promising to radically restructure society to benefit both men and women. But they were very skimpy on details other than promising to 'perpetuate and expand' the government mandated jobs program, to institute a 'radical, progressive new agenda to move our country forward', and to 'empower the leaders of the future'. It all sounded good, but still I planned to vote for the same congressman I always had. After all, he was one of the last few men in the senate, and he had always been an honest and hard worker as far as I could tell. * * * I noticed a shift in Ms. Jensdotter's attitude towards me. I think I expected her to become more demanding and more of a bitch, but the opposite occurred. Instead she became solicitous and interested. Even... motherly. "How is Charlie doing today?" she would ask, every morning. Her use of the diminutive form of my name set my teeth on edge. I had asked her several times to please call me 'Charles', but she would just pooh-pooh my objections and continue calling my "Charlie". Every morning she stopped by my desk and stood right beside me as I explained what I was doing that day. She would then make helpful suggestions as to how to better process the data, or remind me not to forget certain things, or suggest different data I could try to get better correlations. All of this she would do while leaning over and pointing to the tablets on my desk, a hand gently caressing my back. Since she was standing and I was sitting, this put my face about level with her breasts. Did she realize how much her bosom in her starched white blouse was affecting me? Was it intentional or just an accident when they brushed against my face? Of course it didn't help that my member was trapped in its sleeve and I hadn't had sex in a week. Any little thing would make me hard for hours now. But I knew for a fact that my biometrics were being closely monitored. And I knew, further, that if I orgasmed while wearing Sissy Panties... No, the possibilities of what might happen were too terrible to consider! Immediately after each of her visits, I would dive back into work with a vengeance, forcing my brain back into data science to try and erase the image of her well rounded breasts in their lace bra peeking out from between her starched, low-cut V-neck blouse... And every government mandated break I had, I would fetch a glass of ice water and head to the bathroom. But mostly I just gritted my teeth and counted the seconds until my punishment was over and I could remove the infuriatingly stimulating panties and take care of my problems by having normal sex with my wife again. * * * "Charlie, pull up a chair and sit next to me," said Ms. Jensdotter, after our mid-afternoon status meeting. "I want to talk about the best way to label your data sets." I pulled up a chair so that I could see the screens on her desk. Ms. Jensdotter had one of the new holographic desk displays. The top of the desk was tilted slightly and the images felt like they were floating in the air above the desk surface. It made visualizing and manipulating three and four dimensional correlations vastly easier than on my ancient tablets. "Closer," she commanded. "Don't be shy." And so I skooched the chair closer, but still Ms. Jensdotter wasn't satisfied. She pulled me even closer until our legs were touching. For the next twenty minutes, Ms. Jensdotter explained about the corporate dataset and field naming conventions. It wasn't anything that wasn't already covered in the manual. I took notes on my tablet as she explained. I wanted to ask why she was taking her valuable time to explain this to me one-on-one. Had I made an error? But I held my tongue. As long as she was happy, I told myself. That's all that mattered. "Now, do you understand? Is there anything I need to cover again?" "No, Ms. Jensdotter," I said, trying to be as humble as I could. "You were very thorough." "You're a good little boy, Charlie," she said, patting my leg and then leaving her hand there. "I realize that I didn't take enough time to personally take you through the corporate standards, and in that respect I believe I share the responsibility in your poor performance during your first few weeks at CICI. And so I've decided to turn over a new leaf and to invest some of my own time as a mentor, so that we can make a better team together. What do you say to that, Charlie?" But I wasn't paying attention. All I could think about was her hand on my leg, which was now stroking back and forth. The entire focus of my world had narrowed in to that. And then... oh god! A finger reached down and began to lazily trace circles around my inner thighs. I held my breath, desperately trying to control my instinct to jump up and run away. Goosebumps broke out on my arms. "Charlie?" Ms. Jensdotter prompted, with a smirk. Shit. What had she been talking about? The finger worked it's way up my thigh, closer to my crotch. Was it something about working together as team? "That sounds like a wonderful idea, Ms. Jensdotter," I said, taking a chance by giving a generic, but hopefully appropriate, response. "I appreciate this very much." "Excellent," she purred. "Now you can thank me with a hug and a kiss and then you can go back to your desk." Desperate to leave, it didn't cross my mind how inappropriate the request was. With my tablet in one hand, I moved closer to give Ms. Jensdotter a hug, but the action actually made my crotch press into her hand! Boldly, Ms. Jensdotter found my penis (sheathed in the multiple layers of satin by the Sissy Panties) and squeezed it. Desperate to leave, I tried to give her a quick hug and a chaste kiss on the cheek. "Oh, you can do better than that, Charlie," Ms. Jensdotter breathed, putting an arm around my waist and pulling me close. She held me for ten long seconds, one hand pushing my ass forward and the other blatantly groping my crotch and hard penis. I struggled, desperately horny and afraid I might start to spurt right at any moment. But there was nothing I could do. The more I struggled, the more she held me tight, and so finally I was forced to just relax and let her hug and grope me as much as she wanted, gasping as I very nearly lost control. "That's better," she said finally. "And now I want a kiss." But as I went to peck her on the cheek, she turned her head and planted a big kiss right on my lips! I tried to pull away, but she put her hands around my head and pulled me in, making sure we had a long makeout session. "Oops," she said, smirking, as she finally let me go. * * * "Are you saying I just have to take it?" I looked at Cindy, not believing that she could be so unconcerned. It was after hours and I was no longer being monitoring by the business, so I could talk more freely. Cindy and I were at a sushi restaurant downtown near her office for an early dinner. "You're in the business world now," Cindy shrugged, adding some wasabi to her soy sauce. "The rules are different." "But aren't you angry? Angry that your husband is being abused in this way?" "This is no different than women have been treated throughout our entire history," Cindy pointed out. "Being chased around desk, hands thrust up our skirts, being made to wear makeup and low-cut dresses to 'give the right impression' to customers?" "Have *you* been treated like this?" "Of course not!" Cindy snorted, derisively. "No one would dare! But then I'm a lawyer for a top-10 law firm. It's completely different for me." "But it's not right! It makes me feel uncomfortable. And there must be monitors everywhere. I could sue for sexual harassment! I could get her ass thrown in jail!" "Oh honey, no you can't. You waived your rights to sue the company for any sort of grievance when you signed your employment contract." "But the laws are still on the books, right? I just read yesterday--" "Stop. You had the right to sue, but you waived it. Remember the right to waive your rights? You exercised your right to waive your rights when you signed the DP employment contract, and you no longer have the right to sue for harassment." "But I would have never gotten the job otherwise..." I whined. "It's not my fault that you're in a government mandated job with gross oversupply. You could have gone to college to become a lawyer, like me." "My parents didn't think I'd do well as a male lawyer," I sighed. "They encouraged me to go into data processing. You know that businesses only want women lawyers these days." "Well, there you go. I'm not sure I would have married a male lawyer anyway. Ugh. Just the thought makes my skin crawl. Much better to have an DP cutie like you to cuddle with." She reached out and tickled me. "Stop!" I said, batting her hands away, but grateful for the loving attention all the same. "Besides, what did Ms. Jensdotter do that was so bad, anyway? So she groped you. Big deal. You men like being groped by women. It's a known fact. And she kissed you. So what? I bet you encouraged her, didn't you?" "What do you mean, encouraged her? How could I have encouraged her?" "Oh, you know. Maybe you complimented her on her executive skills. Or you asked for her help with something. Or you just stood there looking adorable." "No! How dare you insinuate that it was somehow my fault!" I was incensed. "And why aren't you mad about this? Why aren't you marching into Ms. Jensdotter's office and protecting my honor?" "Oh honey, it's just business. You know the saying: What happens in Ms. Manager's office, stays in Ms. Manager's office. As long as it's part of your job, I'm okay with it. And you need this job. Do I need to remind you of the strings my mother pulled to get you such a plum position?" "No, you don't need to remind me," I harrumphed. I reached for my glass of sparkling water, and sipped it. Cindy refused to let me drink alcohol, saying that there was nothing as unattractive as a drunk male. I suppose she's right. I tried to think. Obviously I wasn't going to get any help from my wife Cindy. What was I going to do? More than at any other time in my life, the planet felt like an unfair, inhospitable place. The system seemed to be rigged against me and my (mostly male) workers in the DP pool. I understood that DP data processing jobs were protected by the government against automation. But that wasn't much help when there were 5 applicants for every job. I shivered, wondering what might happen if I lost my job, and worse, got a public Notice from Ms. Jensdotter. I sighed and leaned my head against Cindy's shoulder. I guess I would just have to live with it. * * * Chapter 5: The Dress Code With a combination of cold showers, ice water and fiercely attacking my DP studies and project work, I had been able to survive the first week without any 'accidental spurting'. Now, entering the second week, I felt calmer and more in-control. The panties were less of a novelty and they affected me less than they had the first week. 'You can do this,' I counseled myself. 'Just one more week.' As James and I stepped out of the elevator, we noticed racks of white shirts being rolled down the hall. "What do you suppose those are for?" James asked as we watched the movers (all men) turn left and roll them into one of the unused conference rooms. "No idea. That looks like the company's logo embroidered on them. Maybe it's marketing swag?" I suggested. Each rack was being carefully tabulated by a woman who double checked the contents and directed the men where to put them. "Yeah, maybe," but James looked doubtful. "It's just that our company never does conferences or anything like that." * * * The mystery was solved when I got to my desk. "*** New Dress Code ***," said the corporate-wide note on my tablet. To encourage a more professional and diligent atmosphere, all hourly workers will be issued corporate shirts. These shirts must be worn at all times while on the job by all hourly workers - no exceptions. Shirts must be paired with long pants or skirts. Pants and skirts must be of a professional-quality fabric (no jeans) in dark blue. Pants and skirts must be clean, crisp (not faded) and in good repair (no tears). At our assigned time, James and I went to stand in line to receive our shirts. "A dress code will be nice and convenient," James said - but in such a way that any other man could tell that he meant the opposite. After all, a dress code? For a professional data processor? They were treating us like children all over again. "Yes, I agree," I said, saying the right words for the monitors but hating every second of it. "No more trying to choose what shirts to wear." "Exactly. And the shirts look very nice. Professional and clean," James pointed out. "Yes, they do. Very professional. Very... clean." "NEXT!" called the woman. I stepped up and tapped my wrist to her tablet. "Charles Underwood," she said, looking at the tablet. "Your boss, Ms. Jensdotter, has asked for an upgrade." "An upgrade?" I looked back at James, who just shrugged. "Yes. It's a shirt with a higher quality fabric. More fashionable. Charles Underwood!" She shouted to a helper (a man) who was working in back. He sifted through the racks and in a few minutes can forward with a bundle of shirts. "Faster, next time," she snapped at her helper. "Yes, ma'am'," the man said, nodding. The female manager went through the shirts, touching the left collar of each one to her tablet. As she did, a soft red light built into the collar blinked on. 'What the heck is that for?' I wondered. "Put one on," she instructed. "Room 5, down the hall. And then come back so we can check the fit." * * * I stood in disbelief, staring at myself in the mirror. It was a blouse. It was a fucking blouse! It was made from a gauzy nylon/polyester chiffon and had pearl buttons at the sleeves and up the front. It was fitted (with style lines that nipped in at the waist) and had a rounded, peter-pan collar. And there, just above my left breast, where a name tag might typically go, they had embroidered the company logo and my name: Charlie Damn it! They used the diminutive of my name. It took me several minutes to control my anger so I could say something positive. "This is a very nice uniform shirt," I finally got out for the monitor. "I will be happy to wear it." * * * On the way to lunch, I saw that they had used "Jamie" for James' shirts. "I asked Ms. Marysdau," James said, "if I could have my original given name instead of 'Jamie', you know, only because I thought that a more formal atmosphere might be more appropriate for better work? But Ms. Marysdau properly pointed out that I shouldn't be questioning the decisions of the organization and now that she has explained it to me, I fully understand. And then she, most properly, gave me a demerit mark to help me remember not to question the decisions of the organization who only have my best interests at heart." It couldn't be more obvious. James had complained about the name on his blouse and was dinged by his boss. "I see," I said. "I'm glad the company is using our less formal names. It makes me feel like I'm part of a family." We looked at each other, trying to maintain neutral expressions, but it was apparent that we both hated it. "What's the red spot for?" I asked. James had a similar soft glowing spot on his collar which showed through the fabric. I had one too, in the same place. "Oh, it indicates my outstanding demerit," James said. "Demerits show on our collars?" I asked, horrified. I couldn't help myself - I immediately reached up and covered my own spot. Previously, my demerits had been just between me and Ms. Jensdotter. But now everyone could see I had a demerit? Everyone could tell immediately that I was on probation for a mistake that I had made? No wonder I kept getting double-takes as people went by. They would look at me, then down at my collar, and then back at me with an expression of: 'Oh, I thought Charles was pretty smart, but I see he has a demerit. Interesting.' It all made sense now. "Yes," James said, "and I must say, it makes sense. After all, we shouldn't be shy about everyone knowing our demerits, don't you agree, Charlie?" I looked at him in shock. He had called me 'Charlie'. That was a first. Were we supposed to refer to each other by the names on our shirts now? I supposed it must be a rule, otherwise why would James have made such a point of it? "Oh, I completely agree... Jamie," I said. Although Jamie's face didn't betray any disappointment, I could tell that my calling him Jamie - while expected - was deeply painful. I looked him in the eyes and I could tell he understood that I was sorry for having to do it. * * * "Ah, you're wearing the new uniform shirt, I see!" Ms. Jensdotter stopped by my desk. "Yes, Ms. Jensdotter. I am very pleased that the company went to all this extra effort to provide such nice uniform shirts for its hourly staff!" I did my best to smile and express enthusiasm - quite a trick since I was burning up inside. "Such nice fabric," she exclaimed, reaching out to hold the sleeve. She ran the soft chiffon fabric between two fingers, oohing and ahhing. "I was one of the managers who requested an upgrade. I hope you appreciate it." "Oh, yes, Ms. Jensdotter," I said. "It's quite a high quality shirt." It was hard to call it a 'high quality shirt' when it was this gauzy white chiffon fabric. It wasn't transparent, but it was much too thin and silky to be a man's shirt. "But what?" Ms. Jensdotter asked, sensing my hesitation, her eyes boring into me. "Nothing!" I said quickly. "I love it! Honestly!" "Of course you do," she smirked. "We specifically purchased something you DP sis--" She stopped herself short. "We tried to get something fashionable and unisex that everyone in the DP pool would enjoy wearing," she finished. "Well, thank you," I said, wondering what she had almost said. But her expression was inscrutable. * * * "Are you getting looks on the looper?" "Yeah," Jamie rolled his eyes. It was after work hours (no work monitors) and we were walking to the new roasted & wilted veggie juice bar down the street. Cindy was working late, so I had an hour to spare before I would have to head home to prepare dinner. "I just ignore them," Jamie offered. "It helps to have the logo, actually. At least we can say it's a required uniform." "I feel nervous," I said. "Like... vulnerable. This man sat down next to me in the looper, and you know they're so cramped already, and when he reached over me to grab a magazine I flinched." "I hear ya," Jamie agreed. "It sucks. What's worse is that people seem to know the purpose of the red light on the collar. I accidentally bumped this guy in the coffee shop this morning fetching coffee for Ms. Marysdau, and he reamed me out pointing to my collar and telling me how much of a loser I was." "Oh Jamie!" I impulsively reached out and squeezed his hand. "I'm so sorry!" "Yeah, well..." he just shrugged as if to say 'what can you do?' We walked into the bar, past the people sipping on various thick concoctions while nibbling on fennel straws and saut?ed fiddleheads with dipping sauces. "Hi girls!" said the waiter in a cheery voice. "Shall I need to precheck with your owner?" Jamie and I looked at each other... shocked. "We're *not* Sissies," I said, in a defensive voice, giving the waiter a hard stare. "Oh!" he looked back and forth between us, realizing he'd made a mistake. "I'm so sorry! I shouldn't have assumed... Sorry! It was just the... shirt. Listen, I'll just shut up, okay? First drinks on me, okay?" Jamie and I looked at each other, all joy having been removed from the outing. "No thanks," I said. "I should probably be getting home. "Me too." As we left, I noticed the stares and smirks from the rest of the restaurant. 'My god, they all think we're Sissies,' I thought to myself, my ears burning and my face turning beat red. 'And I bet they think our owners rejected the precheck!' Jamie and I stood outside the restaurant for a second, just looking at each other. "See ya tomorrow," he said. "Yeah." We hugged and kissed and then went our separate ways. * * * Chapter 6: The End of the Punishment Period The last day of my probation period. Thank god. I counted down the hours, minutes, and seconds with help from an app on my heads-up. Just a few more hours and I would be back in normal underwear and then I would go home and *finally* return to being the man of the house. I had some ordinary briefs with me at work so I could change as soon as the day was over. And OH GOD was I horny! I had never gone without orgasm for more than a few days since I was twelve. Like all men, I had registered with the official Government Porn Registry on my 13th birthday and I had browsed porn all the time, masturbating constantly, until I got married. "No more porn for you," Cindy declared when we got married. As part of the marriage contract (typical for most husbands these days), all of my accounts were subsumed by hers. This gave her the right to cancel my porn rights, which, of course, she did. Without porn, Cindy became my outlet for relief and my romantic obsession. Which was the whole point, of course. All husbands should be dependent on their wives for sexual satisfaction. Fortunately for me, she was more than happy to oblige, almost as much as I wanted. And so, being cut off for these last two weeks had been pure torture. Not to mention the slippery satin panties I was wearing all day, with that infuriating peenie sleeve. Thank god for data science! I learned more about data science in the last two weeks than I had in almost two years of DP community college. And I found all sorts of interesting, off-label correlations in the data, combining it with publicly available datasets from Census, topography maps from the USGS and public social media data. Some of the results were pretty interesting. Certainly Ms. Jensdotter thought they were interesting. I had forced data science to take over my life, so I could maintain control, and it had worked, but just barely. I was desperately looking forward to getting back to enjoying my life... and enjoying my *wife*. Almost there. I just had to get through the afternoon. ** Charlie, it's time for another mentoring session ** As soon as the note popped up on, I fetched my tablet and scurried into Ms. Jensdotter's office, the very image of an obedient and eager DP assistant. She was wearing a 1940's inspired power suit fashionable with women these days. It had the 'power shoulders', a row of buttons up the front, and a crisp A-line skirt. The jacket was fitted, highlighting her ample bosom. Underneath she wore a white linen blouse. While it was definitely updated, it would not have looked out of place in a war room from WWII. She looked powerful. "Where's the chair?" I asked. Normally I would pull up a chair and sit next to her as she reviewed company policies or DP processes, all the while having to endure some 'under-the-table' hand action as she stroked my legs and ran her fingers across my crotch. But today the chair was gone. "Oh, someone borrowed it," Ms. Jensdotter said, breezily. "RC, monitor off." The room controls softly chimed an acknowledgement. Ms. Jensdotter motioned me over. "Are you wearing your Sissy Panties?" "Yes, Ms. Jensdotter." A light blush rose to my cheeks. "Show me," she said, with a penetrating gaze. "After all, how will I know unless you show me?" "Oh.... okay." I felt a shiver run through me. Slowly, I undid my belt and revealed the ridiculous pink confection of lace and satin which was my Sissy Panties. "So beautiful," she purred, batting my hands away and pushing my pants down to my knees. "I had no idea they made such beautiful panties. Oh dear, are you...?" She gently grasped my penis through the Sissy Sleeve and slowly drew it through her fingers. I sucked in my breath. I was quite swollen already. I closed my eyes and gritted my teeth, trying to control myself "Come, sit on my lap," Ms. Jensdotter said, tugging on my peenie. "Since there's no chair," she added as an afterthought. I reached down to pull up my pants. "No!" Ms. Jensdotter barked, before continuing in a more soothing voice. "Leave them down. After all, this is the last day you'll be wearing Sissy Panties, correct? And so humor your poor old boss and let her enjoy them this one last time." I heard mocking in her voice. I paused for a second, feeling like this was a very bad situation, but what option did I have? I sat carefully in her lap, my pants still around my knees, the multiple layers of satin in the Sissy Panty slipping against each other as my bottom nestled between her legs, like a child in her mommy's arms. "You know," she said, once I was settled, "I don't really need to see your panties to know that you are wearing them." She put one hand around my waist and began to gently stroke my chest through the gauzy uniform shirt. I reacted to her touch to a worrying degree. "Uh, Ms. J-J-Jensdotter, M-Ma'am?" I stuttered. "Perhaps we should just focus on data science?" I held up my tablet to show her my latest correlations. "Please?" The pleading in my voice was pathetic. "Hush, there's plenty of time for that later," Ms. Jensdotter said, gently taking my tablet away and putting it aside. "I want to spend this time getting to know you better. Did you know that all Sissy clothing is tagged and tracked? It's required by law. Here, let me show you." She swiped across her desktop and spoke 'Charlie Underwood, clothing'. The screen displayed seven pairs of Sissy Panties and three uniform shirts. All of them had unique IDs and all had green 'active' badges. One pair of panties had a pulsing red light and a small activity graph. With a flick Ms. Jensdotter selected the entire set and spoke "map, all time". I gasped. There, mapped across the city and the neighboring county was all my movements for the last two weeks! Ms. Jensdotter zoomed into the office location on the map, and there I was, a pulsing pink dot. "You see? All Sissy clothing is uniquely keyed so that it can be tracked wherever you go. There's sensors everywhere so, basically, it's impossible to escape." Her voice had a tone of control and authority which made me shiver. Tracked everywhere? Even outside of work hours? "How does that make you feel, Charlie?" Ms. Jensdotter asked. She pulled me closer, one arm wrapped around my waist and the other stroking my leg. "Do you feel monitored? Followed? Trapped and unable to escape?" "How did you get this data? I mean..." "Your wife gave me access to your feeds." "Cindy?" "Yes, Cindy Pauline, your wife. I asked, and she said it was her honor. She thought it would prove that you were a real man. And that if you weren't... " Ms. Jensdotter let that statement hang for a moment. "Which reminds me, there's something else I want to show you." I squirmed as Ms. Jensdotter wrapped her arms around me and spoke "Charlie Underwood, Biometrics." The display showed my standard health statistics, pulse, temperature, blood pressure, calorie levels (ingest and burn), and so on. "Sex-ex," she spoke. The biometrics swiped right and her desktop monitor displayed my 'sexual excitement levels'. "The Sissy Panties actually measure your... uh... tumescence," she giggled. "As well as the temperature and electrical activity of your, uh, private parts. This is combined with your standard biometrics... See this line here? It is your estimated overall sexual excitement." The line she pointed at seemed to bounce up and down dozens of times per day. "And these red peaks? These are when you're dangerously close to doing your little Sissy Spurties, as we say. And look!" she pointed to the far right of the graph, which was being extended in real time. "This is your status right now. Why Charlie, you're in the red zone right this minute!" I gasped. She was right. There were three lines under the "sexual excitement" graph, and they were all bumped up and showing red. I stared at the graphs, shocked. I knew they were monitoring my video and audio streams, all companies did that. But I had no idea that the Sissy Panties were adding additional data! In retrospect, perhaps I should have known. "I must say, you surprised me, Charlie. Our models predicted a 97.5% chance that you'd spurt by now. Even with the ice water in the bathroom and the cold showers at home, oh yes, we know all about those! But still, somehow you maintained control. That's admirable and quite remarkable. That makes you one of two or three in ten thousand. At the very edge of the bell curve. 99th percentile." "Thanks," I said, still staring at the graphs. The lines bumped up a little. Damn, how long could I last in the red zone before it was too much? Desperate for a distraction, I tried to recall my latest data science correlation. It had something to do with sloping elevations-- But Ms. Jensdotter, seeing the lines start to drop, pulled me tighter into her lap, kissed my cheek and ran her fingers through my hair, like a mother might do with her daughter. And just like that, the lines jumped back up again. I tried desperately to focus on data science, but it was impossible. "And it's only because you've had such good self-control that we're here now," Ms. Jensdotter explained. "It's time to test to see where your, shall we say, proclivities lie." Ms. Jensdotter opened up a drawer and pulled out what looked like a heavily embellished, silk-satin towel. It was trimmed in lace and embroidered with flowers and bunnies and the words: 'My First Spurties Towel'. Ms. Jensdotter laid it over my leg. It was thick and soft and must have had multiple layers of soft material sewn together. "My Sissy Cupcake hand-made and hand-embroidered this for you," she whispered into my ear. "Isn't it beautiful?" "Y-y-yes," I stuttered. It drew my eyes like a magnet, and I could feel it on my leg as if it somehow exuded a kind of tingling sexual energy, as if it were alive and might soon swallow me up into a kind of silky sissy cocoon. "Oh, look," Ms. Jensdotter said, "your graph is jumping up. Do you see that horizontal line? That's the line of no return. You should be careful to keep your excitement below that line." I watched as my graph flirted within a few pixels of the line. "Please... Ms. Jensdotter... please..." "Please, what? Charlie?" she asked. I arched my back and groaned out loud as Ms. Jensdotter sensuously stroked her hands over and around my body ending on my breasts, her fingers tweaking and flicking back and forth across my nipples. "Please..." I begged her, squirming to get away. "Please... may I go now?" "No," she said, firmly. "Oh Charlie, even though you were able to maintain your control - just barely - for your two week punishment period, we both know what you really want, don't we? After all, I have access to your porn registry. Did you know that? And analysis on your viewing habits shows a marked tendency towards strong women, submissiveness and women's clothing. I've talked with Cindy, your wife, and she seems like quite a strong woman to me. Don't you agree?" "Yes, but that doesn't mean--" I wriggled some more, trying feebly to escape her clutches. Her assault on my nipples was driving me insane. I looked at my graphs and all indicators were now bumping right up against the horizontal line of no return. "Of course not," Ms. Jensdotter said. "Liking strong women doesn't mean that you're a sissy. No one said it did. After all, Sissies like giving pleasure to both women *and* men... *and* other Sissies, don't they, Charlie? Like your sissy friend Jamie." "Please," I moaned, desperate to make her stop. "Jamie is only a friend. And I'm only supposed to do this with my wife." "Oh, your wife and I talk all the time. I'm sure it will be okay with her. As long as you maintain control. And besides, I can't let you go until we've tried your new spurties towel, now can I?" she said, reaching down and picking up the towel. "My sissy made it specially for you. See how beautiful and soft it is?" Ms. Jensdotter rubbed the towel across my cheek. It *was* deliciously soft, thick, and smooth, and I could tell it was covered in real silk. It smelled of baby powder and potpourri. "Isn't that nice?" Ms. Jensdotter said. "Yes..." I sighed. I glanced quickly at my charts. Did I see a quick jump over the line? "Why don't you kiss it?" she asked. "Kiss it so I can tell my Sissy Cupcake how you blessed the towel that she hand-made for you with a kiss before its first use. Kiss it, Charlie." I hesitated, looking around the room, desperate to figure a way out of her clutches. "Kiss it," Ms. Jensdotter said, holding it up to my lips. Thinking it might be better to get this over with, I pursed my lips and kissed it. The soft silk and and lace felt heavenly against my face. "That's my Charlie," she cooed. "Now do you know what a spurties towel is for?" "No..." I moaned. "It's for catching Sissy spurties, of course! Sissies are spurting all the time - it's their nature. That's why they need to be milked so often. So whoever they are with, a woman, a man, or another Sissy, they always have a spurties towel handy to catch their spurties nice and neat and to never make a mess. We know, of course, that Sissy Spurties can be quite messy, don't we?" "Please, Ms. Jensdotter... please let me go," I struggled some more, but for some reason I was feeling weak and powerless. "I don't want to break my wedding vows!" "Whether you break your wedding vows or not is entirely up to you, Charlie. Shall we christen your spurties towel?" "No. Ms. Jensdotter, please, I think we're done here... oh, oh, oh....!" Ms. Jensdotter silenced my objections by wrapping the spurties towel around my hard member trapped in the Sissy Sleeve of my Sissy Panties and started to stroke. All of my indicators immediately jumped well above the line. "Stop! Please, Ms. Jensdotter! Please, Ma'am! Please stop!" I was practically in hysterics now. "No," she growled into my ear. "I will not stop. Because we both know who you really are, Charlie! Deep down inside you're a sissy. You love wearing your panties. You love being subservient to strong women, and probably men too and bending to their will. You love being forced to wear sissy panties and to sit in the laps of strong women while they stroke your peenie with a spurties towel, don't you? You love it like a sissy loves it." "Nooooo..." I moaned. But even though I struggled and twisted and squirmed and wriggled, Ms. Jensdotter held me firmly in her arms, one hand stroking my chest and gently pinching my nipples and another with the soft and evil spurties towel, wrapped around my member, the silk of the towel sliding smoothly over the nylon satin of the peenie sleeve, the tip of my peenie nestled in the towel itself. "Let go," she whispered, nibbling, kissing and licking my ear. "You know you can't hold on any longer. You know you need release. Just let go and let it happen. Come on Charlie, I know you can. I know you want to. Let go, my dear. Give in to your better. I know what's best for you." "Please..." I whimpered one last time, but it was too late. My trends were all way over the line by now. With a cry, I convulsed and spurted. And spurted and spurted. Over two weeks of sexual denial, stimulation, and frustration battered down my willpower and I came and came and came, my body spasming in pleasure, flooded by the most powerful orgasm I had ever known. So overwhelmed, I burst into tears. I had failed. Two weeks of self control, cold showers, careful dressing and walking, data science mind games and it was all for nothing. I had failed to complete my punishment and I had failed my boss, my wife and her mother. I'd get a Public Notice now for sure, and my life would be ruined. I'd never get another job as a data processor. Cindy would divorce me and throw me out onto the street, homeless. All because I couldn't maintain control for just another few hours. I had spurted, and worse, I had done it in the firm hands of my boss, Ms. Jensdotter, at work, during working hours as she whispered sissy thoughts into my head. "There, there," Ms. Jensdotter cooed, as I sobbed my heart out, my head nestled into her neck, her hair brushing against my face. She continued to milk my member as I cried, drawing out all of my spermy cream into the sissy towel, my body jerking and twitching with aftershocks well after the initial climax. ** Public Notice, Approve? ** I looked up, in horror. So quickly?? There, floating above her desk was a dialog: Official Public Notice of Negligent Performance Charles Underwood 1) Violation of corrective program (dated 2088-05-30, CharlesUnderwood418) terms. 2) Violation of Appendix C, section 3, subsection 2 of CharlesUnderwood418 employment contract, prohibition of sexual acts in the workplace. Four factor approval process required. Approve? I struggled to get up, but Ms. Jensdotter held me fast in her lap. And then I noticed... ...a second red spot had appeared on my collar. "Yes, this is your second demerit," Ms. Jensdotter said, with a smug voice. "How terrible. You know, Charlie, having two simultaneous demerits is usually an automatic OPN-NP. Hmmm.... I wonder if I should approve?" "Please Ms. Jensdotter!" I pleaded. "My first demerit was going to expire tonight." "A pity then that you couldn't control yourself for just a few more hours," she smirked. "But not my problem. After all, rules are rules." "Please, Ms. Jensdotter," I said, grasping at her wool tailored jacket like a little child. "I put myself at your mercy. What do I need to do?" "Now *that's* exactly the sort of willing attitude that I'm looking for in my assistant," Ms. Jensdotter said, a predatory note in her voice. "Oh Charlie, maybe this will work out after all. Now, I have exactly four conditions from you before I will consider dismissing the Public Notice." "F-four c-c-conditions?" I stammered. "Wh-what are they?" "Tutt, tutt, Charlie. 'Yours is not to reason why. Yours is but to do and die.' As a man, you should understand that. Remember your male, military tradition. Not that there's much call for that these days." She was referring, of course, to soldiers being obsolete thanks to battlefield robots. "So now you have an order from a *superior officer*," she continued. "What will you do? Do you understand that I am molding you into my perfect assistant in the way that I see fit? Will you question and wonder why? Or will you take your punishment *like a man*? Do you trust that your punishment will turn you into the assistant that I need? Like the hammer forging the iron into a blade of steel?" Of course, by referring to men's glory days in the military as the defenders of freedom, Ms. Jensdotter knew exactly what she was doing. She was appealing to my sense of duty and to every man's desire to be significant and respected. But she was also drawing a clear line. 'Do as I say, without question, or you will be fired.' There was an unbending will behind her words. "Yes, Ms. Jensdotter," I said, humbly. "Yes, what, Charlie? Be specific." "Yes, Ms. Jensdotter," I said, my voice shaking. "I trust you. I will agree to your punishments... to-to-to make me a b-b-better assistant. Whatever you feel is best." I hung my head, feeling lower and more submissive than I had ever felt in my life. "That's my darling Charlie," she said as she stroked my hair. "Condition one is the cane. Get up, bare your bottom and lean over the desk." I gulped. I should have known that a caning would be part of the punishment. I got up on unsteady feet and minced over to the desk (my pants were still around my knees) before lowering my panties (my penis still trapped inside that accursed sheath) and assuming the position. Ms. Jensdotter stood behind me, lightly stroking my bare bottom with her fingers as I twitched and shivered. "It was twenty strokes last time," she said, swishing the cane through the air to test it. "And so I think that this will need to be forty strokes this time." Forty strokes! I groaned out-loud and hid my head in my arms. "No hiding!" she commanded, grasping my hair and pulling my head up. "Maybe we need to make it clear why you are being punished?" She pushed my arms apart and placed the spurties towel flat on the desk, right under my face so I was forced to look down directly into it. Oh my god, did I really spurt that much cream? There were great big globs of it all over, slowly soaking into the silk embroidery. The cloying, moist smell was pungent. "Now let's see if you can take your punishment like a man," she sneered. I felt the cool rod rest briefly against the curved flesh of my soft buns before Ms. Jensdotter pulled it back and gave me the first of my forty strokes. The caning continued at slow, but measured pace, Ms. Jensdotter choosing her spots carefully to cover as much un-touched skin as possible. Each stroke raised an bright pink line across my bottom. Where the lines crossed, the skin turned purple. I started strong, maintaining my composure, staring down at the source of my shame - 'My First Spurties Towel', wet with gloppy cream. And I made it almost to twenty, jerking forward and grunting with every stroke, before my willpower started to crumble. "That's it, Charlie," Ms. Jensdotter said, grunting with effort as she gave me another stroke, this time at the top of my thighs. "It's okay. Just let go. Surrender to me. You don't have to be a strong man all the time." A few strokes later, I gave in. "Ms. Jensdotter!" I cried. "Please stop! Please stop!" "I'm sorry, Charlie," she said, applying another vicious swipe. "But you must take *all* your medicine. How else will you learn? Now let it all out, that's a good sissy assistant." And I did, crying and wailing as I received each new stripe from the cane. My tears dripped down onto my Spurties Towel, mixing in with the sperm from before and wetting the towel even more. And still the strokes continued. Lines of pain, burned into my brain, and I sobbed and sobbed, until at some point, it pushed me past some hidden boundary that I didn't even know I had. A place of acceptance. Of true submission to a higher power. "All done," Ms. Jensdotter announced, finally. I stayed bent over the desk on my arms, staring down at my towel. I winced and clenched as I felt Ms. Jensdotter's hand trace along the stripes on my bottom which radiated raw heat. There was a long pause and I heard the rustle of clothing followed by heavy breathing. A few moments later there was a moan and then I felt a hand gripping my ass! "Oh, Ms. Jensdotter!" I cried. I tried to escape by shuffling sideways, but she held me in place, gripping and kneading my sore bottom, until finally I heard a long sigh and she relaxed her grip. "Stay," she commanded. I heard more rustling of fabric. "Ah yes," she sighed. "Very nice. Now Charlie, kiss the cane and thank me for your punishment." The cane appeared before me, a polished wooden rod. I was too far gone to object. Gently I lowered my lips and kissed it. "Thank you for taking your time to correct me," I said. "I... ah... I understand that I violated policy and... um... I appreciate you providing this individual attention to make me a better assistant." "That's my Charlie," Ms. Jensdotter said. I heard a desk drawer open and close. "Now this is the second condition, an adornment. Some jewelry I want you to wear." Ms. Jensdotter grasped my wrist and tapped it with a shiny silver device shaped like a... it was a silver butt plug! And it had a wide, pink jewel decoration on flat end that glowed and pulsed twice to signal a successful pairing with my implants. "This will make your little butt hole so pretty!" she said. "Now lick it. You'll want it to be nice and lubricated." She held the silver tip to my mouth. Disgusted with myself, I accepted it into my mouth, getting it as wet as I could with my saliva. It was smooth and cool to the touch. Ms. Jensdotter thrust it back and forth a few times, I could tell she was simulating a man's cock (damn her), before finally pulling it out. Parting my ass cheeks with one hand, she pressed the tip against my anal rosette and worked it in, slowly but firmly, finding the right angle, until finally the wide part finally passed my sphincter. "Oh look, you're drawing it in, deep inside you! Oh, Charlie! It is so pretty on you! I'm recording this, by the way. I can't wait to show these videos to all my colleagues." "Please no! Ms. Jensdotter!" I stood up quickly, hiding my bottom with my hands. Being punished by Ms. Jensdotter was one thing. Sharing embarrassing video with all of the staff, however...? "Lay back down!" Ms. Jensdotter barked, pushing me back into place, my ass in the air displaying my new butt-plug jewelry, I was sure, to Ms. Jensdotter's ocular cameras. "Don't worry," she said, in a more conciliatory tone. "It's just 'Your-Eyes-Only' for a few friends and colleagues. I promise." "Thank you, Ms. Jensdotter," I said, my face flushed bright red. "I apologize for my outburst." "I understand this is hard for you," she said, her hands stroking my bare bottom and occasionally dipping down to wiggle the butt plug (making me dance and squirm). "After all, you're not used to being a..." she paused, "... uh... I mean... assistants like you can be very emotional." Assistants like me? What did she mean by that? "Yes, Ms. Jensdotter." "You may stand up now and put your clothes back in order." "Thank you, Ms. Jensdotter." Quickly, I did as she said, grateful to pull up my Sissy Panties and trousers and tuck in my uniform shirt. I felt the butt plug move about inside my bottom as I stood. This would take some getting used to. And if that weren't bad enough, my peenie was already hard inside the sheath of my Sissy Panties. "Am I done, Ms. Jensdotter? May I go?" "Most certainly not!" Ms. Jensdotter just laughed at me. "I have two more conditions. Do you want to hear what they are?" Red faced, I stared at the ground. "Yes, Ma'am," I mumbled. "Of course, Ma'am. Thank you, Ma'am." "That's better, my Charlie," Ms. Jensdotter said, coming over to me and placing an arm around my waist, pulling us together, intimately. I looked down at the seams of her sharply tailored suit. She looked so strong and superior. "Your new jewelry item is, of course, a gift from me, and I expect you to have it firmly in place while you are at work. Now I can't control what you wear outside of work, but it would be pleasing to me if you wore it on your off hours as well." 'Fat chance of that,' I thought to myself. "Now since you were unable to complete your first probationary period with a clean record, I think we will have to continue it for another month." "Another month?" I gasped, looking up at Ms. Jensdotter with a shocked expression. "Careful, Charlie," Ms. Jensdotter warned. "The OPN is still waiting for my approval." "Yes, Ma'am," I said, quickly. "I understand Ma'am. Of course, that makes sense. Will I have to...?" "Have to what, Charlie?" she asked, mercilessly. I gulped. "Will I have to wear the Sissy Panties for... for another whole month?" I asked, my last words coming out as almost a whimper for mercy. "Yes you will," she said, triumph glittering in her eyes. "But you just did two weeks, Charlie. What's another month? I'm sure you'll be fine." "Oh my gosh," I mumbled, crestfallen. "Another month. Another month..." I had just barely lasted for two weeks. How would I ever last for an entire month! And I knew that if I had another slip-up, I'd be noticed for sure (if not fired outright), and then my career would be over. "Charlie..." Ms. Jensdotter's voice had a note of motherly concern. "I can tell you're worried about maintaining control over your... shall we say... your passions. I know that this is not easy for someone... like you. Would it help if I recommended you for a milking schedule?" "A milking schedule!" I said, incensed, taking an abrupt step backwards. "No! I don't need a milking schedule! I'm not a... a... " Ms. Jensdotter looked at me, an eyebrow raised. "I'm a man!" I finished. "Milking schedules are for men too. Well, I've ever actually heard of a man being put on a schedule..." She smirked. "At least not in this company. But there's always a first. Maybe you will be the first, Charlie. You would be blazing new trails, crossing new boundaries!" "No!" I said definitively. "I do NOT want to be put on a milking schedule." "Suit yourself," she shrugged. "But know this. There will be no more warnings, no more probation. If you have another lapse, I will be forced to submit a public notice." "I understand," I said, through gritted teeth. "And there is one final condition." Another?? "Yes, Ms. Jensdotter?" "In addition to your Sissy Panties, you will wear a Sissy Bra as well." Oh no... my heart sank to the floor. "A-a-a... A Sissy B-B-Bra?" I stuttered, suddenly feeling weepy. "Yes. And you will wear both the bra and the panties for the duration of your probationary period." "But--" "Now go immediately to the Sissy Store and purchase a bra. I will expect to see it when you come back. You are dismissed." * * * Chapter 7: The Bra "Mademoiselle Charlie!!" Creampuff squealed, running over to me and grasping me into a big Sissy hug. "Oh, it is so *wonderful* to see you again, Mademoiselle Charlie! How have you and your panties been these last two weeks? Have you enjoyed all of their special features? Don't you love all of the lace adornments? Don't they make it just so wonderfully sissy in all of the best ways? And the sheath! Don't you just *love* the sheath? After I saw what you had picked out, I bought one for myself! And it is *so* yummy! I can barely control myself every day... not that I was very good at it before...." All of this came out in a rush, punctuated by giggles as Creampuff led me to the big bed in the store. There was another couple already on the bed, a nervous and embarrassed young man and his Sissy going through her tablet and making choices about sissy panties. This didn't bother Creampuff, who pushed me onto the bed and then clambered on top of me, laying her body across mine and giving me little kisses on the cheek. The action made the plug in my ass pull out a little before my sphincter drew it back in, the action of which made me gasp and wriggle my bottom. "Is something the matter?" Creampuff asked. "Is there something going on... down there?" It was 'Sissy Baby Girl Week' in the store and all of the video walls were decorated in a screaming pink baby girl theme, with pacifiers and cribs and baby dresses and dollies and stuffed animals. On the other side of the store, the sides of the crib had been let down and a second couple, another man and a sissy, were snuggled up together with another tablet going through panties and bras. Creampuff herself was dressed in a shiny nylon pink satin sissy baby- girl dress. It was "smocked" with embroidery that gathered the fabric high on her chest. The waistline was actually above her (ample) breasts and then the skirts and multiple petticoats cascaded down over her breasts to end just below her crotch. It was such a disgustingly sissy outfit it made me hot and embarrassed for her. Other than the dress, Creampuff was wearing a poufy set of thick plastic-covered disposable diapers (pink with printed baby-girl dollies and stuffed teddy bears on it), shiny silk-nylon tights (thick and slippery with little pink ribbons running down the side) and ballerina slippers also decorated with big pink bows. "Oh, Charlie!" she said, running her slippery nylon covered legs over the bulge in my pants. "I'm so glad you are so happy to see me! But why haven't you been back to visit over these last two weeks! I've been so lonely without you!" Creampuff put on a pouty face. "I... uh... was busy with work..." I said, trying to sound gruff and manly. "Oh, poo," she said. "That's a lie. You may be able to hide your emotions from the monitors in the cloud, but you can't hide them from me, Charlee. I know you were ashamed of me and having to visit the sissy store. But that's okay," she whispered into my ear, "all sissies are ashamed at first. I'm ashamed even now. It's part of being a sissy. The shame comes from knowing that, deep down inside, what you really are is Sissy." I looked at her sharply. This was not the case. I'm a man! My first reaction was to storm out of the store or violently pushing Creampuff away, but that would have been lashing out, but I restrained myself since I knew that anything negative would be immediately reported to Cindy. But fuck, why am I so hard? I sat up and gently pushed Creampuff off of me. Unable now to lay on top of me, she instead nestled her bottom up next to mine, her delicate hands with their bright pink nails draped around me. "I'm just here to buy..." I started, but then couldn't finish. I looked around the store, my face flaming bright red. "... a sissy bra," I finished, almost in a whisper. "A what?" Creampuff asked. She knew very well what I had said, of course. She just wanted to embarrass me more by making me say it out- loud. "A sissy bra," I said, a bit louder, so that only she could hear. "I'm sorry, Charlie, what was that?" she mimed holding up a hand to her ear. "A sissy bra," I said, hiding my eyes but saying it loud so that everyone in the store could hear. "A sissy bra?" Creampuff said. "Is this for you to wear?" she asked. "Yes," I admitted. "A sissy bra for *YOU* to wear, Charlee?" Creampuff said, nice and loud, making me wish I could just instantaneously disappear. "Well, that's wonderful! We've been getting lots and lots of manly, manly men buying sissy panties, you know, as punishment for their wrongdoings. But you're only the second one who is buying a *bra*. How wonderful! Oh, you'll so love the feeling of smooth satin and silk on your breasts and nipples. Once you try one on, you'll be wearing them forever! Let's see if we can find a thoroughly Sissy bra for you to wear!" Creampuff started flipping through various sissy bras on her tablet, the images replicated on the walls in front of us so that everyone could see. I kept trying to pick one of the plain, unadorned bras with simple straps and nylon or cotton cups and no lace, but Creampuff refused to sell those to me. "You know that your wife, Cindy, would refuse to let you purchase them," she counseled. Finally, we agreed on a style. It had shiny nylon-satin cups gathered around the edges, pink ribbon shoulder straps, delicate scalloped lace around the neckline, a small decorated pink ribbon in the middle, and a wide stretchy lace around the torso under my breasts. Of course, as last time, my wife Cindy had to approve the purchase remotely. "What is this?" she asked. "I'm being punished at work again," I explained, holding my head between my hands. "I... I have to wear a sissy bra in addition to my sissy panties for the next month." "THE NEXT MONTH!" Cindy said, shocked. Creampuff looked over at me, honestly shocked and holding her hands over her mouth. "What did you do??" asked Cindy. I suspect she already knew what I had done, after all, she would have been notified of my orgasm, but I think she wanted me to say it out-loud. "It's not my fault!" I tried to explain. "Ms. Jensdotter made me... lose control." "Lose control? How??" "I... I spurted. In her office." "Charles!! How could you?" "She made me take my pants off! And she forced me to sit in her lap..." "Forced you. Uh huh." The sarcastic acid dripping from Cindy's words burned into me. "You broke your wedding vows." "It's not fair!" I cried, feeling myself tear up. "I would have been fine except that-- that-- she--" "Shhhhh..." Cindy said, shushing me. "It's okay Charlie. These things happen. So you failed the test. I had a suspicion you might. Ms. Jensdotter told me what she was going to do ahead of time and I admit that I was worried. But I let her do it so we could both see what your limits are. I do know that it's hard to maintain control for... men like you sometimes, especially in circumstances like that." "I'm so sorry, Cindy," I said, feeling horrible. Cindy sighed. "I'll forgive you this time. And now, you'll just have to deal with this new situation, won't you? You'll need to take your punishment like the man that I know you are. Did you get a Public Notice?" "No. Not if I wear a sissy bra for the next month in addition to sissy panties. That's my new punishment period." "Well then, it looks like Ms. Jensdotter is being more than fair. I've seen the style you've picked out and it looks appropriate to me. Buy five pairs in different sissy colors and I'll approve them. Now I have to go to a meeting, but we'll get through this together, okay? I still love you, Charlie." "I love you too, Cindy," I said, sniffling, as she disconnected. After choosing five different colors, I bumped my wrist to the tablet and the sale went through, immediately followed by a note on the screen: "Repeat Customer Special Gift!" "Yaay!!" Creampuff said, bouncing up from the bed. "You have bought so much from us that you get a free gift! And I get to choose it!" Creampuff skipped away, disappearing in the back of the store. "You're free gift," she purred, holding up a bit of pink and white lace and ribbon. "Wha--what is it?" I asked, shuffling away from her. "Shush, it's okay. You only have to wear it in the store," she said. "It's your first sissy collar. See? It's even embroidered with your name: Charlie. And see what it says here? 'Obedience'. All sissy collars remind their wearers that they must be obedient to their betters." "Please, no, Creampuff," I protested as Creampuff placed the lace and ribbon collar around my neck. But I didn't do anything to stop her. I just let her collar me and tie it in the back with a big bow. "Shhhh...." she said, tracing a finger over the collar. "It looks beautiful on you." Creampuff took a long ribbon and tied it around the small ring stitched into the front of the collar. "When you wear the collar, you must obey," she said. "Now come with me." Creampuff got up from the bed and tugged on the ribbon. I followed her across the store where there was a small open area with a mirror where she tied the ribbon to a ring on the wall. "Now stay still, like a good little sissy," she said, giving me a kiss on the lips with a wet, open mouth. Her fingers strayed down to my pants where they undid my belt, unzipped, unhooked and pushed my pants down to my knees. My hard penis sheathed in the sissy panties thrust out, the red tip surrounded by its lace collar like a pet eager to be played with. Next, Creampuff carefully undid the buttons on my logo uniform shirt and tossed it aside, leaving me naked from the knees up except for sissy panties and the collar. "I'll be right back," she said, first sucking and licking each of my nipples before leaving me alone in the dressing area behind the screen. I stood there, shifting on my feet, exposed and naked, the leash on my collar tied to the hook on the wall preventing me from sitting or leaving to go hide. Everyone in the store could see. I reached up to undo the collar, but then dropped my hands again. Creampuff had told me to stay still and be a good little sissy, and I felt compelled to obey her. But this was ridiculous! I was a man! I could do as I wished! My god I was horny. I saw myself in the mirror. My little peenie stuck straight out, straining as if waiting eagerly for Creampuff. The sheath was stretched to full length. It was stained with the remnants of my spurties at the office. My num nums in the pink sack looked full and heavy and bloated, framed by the pink lace and ribbons of the panties. "And here we are!" Creampuff skipped back into the dressing room holding the first of my new Sissy Bras. In three dimensions it looked even more overwhelmingly sissy. Shiny with white lace trim and light pink cups. "Now let's try this on for fit," she said holding it up. "Charlie?" Creampuff said warningly when I hesitated. "You still have the obedience collar on. Trust me, you'll love it, I just know you will!" I let her slip the bra up my arms. It was like a soft cloud of lace and satin and ribbons settling over my chest. Turning me around, she hooked it up in back (with six hooks) so it was nice and snug. "There," Creampuff said, turning me to face the mirror. I turned away in shame, not wanting to see the image, but Creampuff turned my head and forced me to look. "Don't you look delicious," she said. She circled my waist with her arms and reached up to play with my nipples inside their satin prisons. "Did you realize that Ms. Jensdotter opened up parts of your profile to the store?" "What... what does that mean?" I asked, squirming in her embrace. "It means that I know a few more things about you," she whispered into my ear. "It was necessary in order to make the right bra for you." "Wha--- what do you know?" I shivered, wondering where this was going. "Just that you have something hidden down here," Creampuff said, her cool slender hand slipping down into my Sissy Panties and then between my buns. She placed a finger on the jewel of my butt plug and worked it back and forth, making me gasp and hiss with pleasure. "Although I have no idea why a self-professed 'man'," she said 'man' in such a way that I could hear the air quotes, "like you would agree to be pegged with a Sissy Trainer." "Pegged? What do you mean? What's a Sissy Trainer?" "You mean you don't know what it is?" Creampuff asked, her voice ringed with surprise. "Oh, Charlee! But how can that be?" She continued to manipulate the butt plug, this time gently thrusting it in and out. My hips matched her motion, my throbbing penis with its lace collar bouncing up and down in the mirror. "Hands on your pretty titties," Creampuff commanded, with an extra press of the plug. As if shocked, my hands jumped up to my breasts, covering them. Creampuff reached down with her other hand and started stroking my peenie through the sheath of the panties. "Now play with your cute little nipples," she commanded, "and let's just enjoy ourselves while the rest of your Sissy Bras are being made." "Please... what's a Sissy Trainer?" I begged. As if in a trance, I stroked my own nipples through the satin nylon bra cups. "Shhhh," Creampuff said. "I can't tell you. Let's just say that you'll be full of all sorts of delicious sissy feelings." "But what's that mean?" "Don't worry," Creampuff increased her motions sensing I was near. "You'll come to love it, I promise!" Suddenly, I realized where this was headed! "Stop!" I begged. "No," Creampuff responded. "Please... I can't... I shouldn't... I mean, Cindy... my wife...!" But it was already too late. with a few more strokes and a loud grunt, my peenie spurted, globs of sperm splatting against the mirror like a Rorschach test. "That's my good little sissy!" Cooed Creampuff, continuing to manipulate me through the after shocks. After a few more spurts I finally settled down, then looked towards Creampuff with teary eyes. What was becoming of me? My heads-up beeped. "Charles, what *are* you doing??" Cindy demanded. She had been notified of my orgasm. "Violating your marriage vows *twice* in one day?" "I'm so sorry, I'm so sorry!" I blubbered. "I'm in the Sissy Store, and..." "It's my fault, Ms. Pauline!" volunteered Creampuff. I looked at her so Cindy could see her. "I tied him up, see? And then fondled him until he had to spurt. You know how Sissies are." Cindy laughed. "Yes," she admitted, "I do know how sissies are. Or so I've heard." Wait... was Cindy referring to Creampuff or to me? "Well, alright, Charlie. You fell into a Sissy Trap, I guess I can't blame you for that." "Thank you, Cindy." My face was bright red with shame. "But now you know. If it happens again, I will assume that you are willfully breaking your wedding vows, and I will want a divorce. Do you understand?" I gulped. This was serious. "Yes, Cindy," I whispered. "Good. We understand each other." She logged off. "What a nice wife," Creampuff said. "I wish I had a nice strict owner like her." Creampuff gathered up the drops of cream leaking from my peenie with her fingers. "Now Charlie, you still have the obedience collar on," she reminded me, bringing her fingers to my lips. I looked at her, begging with my eyes to please not continue, but Creampuff was insistent. "Obey your betters," she whispered. Reluctantly, opened my mouth to accept her fingers, tasting my cream for the first time, an organic, slightly salty, slimy taste. Creampuff continued for a while, thrusting a finger into my mouth as if I were sucking on a little sissy peenie. Finally, she untied the leash from the wall. "And now, the mirror," she said, pulling the leash down so that I was on my knees facing the mirror. I stuck out my tongue which met the tongue in the mirror at the cool glass where I licked up my spurties, drawing it all into my mouth at Creampuff's command. "You *are* a good sissy," she said with a pat on my head and running her fingers through my hair. Creampuff pulled me up by the leash and pulled me into a long kiss. "And you taste good too," she sighed. * * * Finally, Creampuff untied my collar (placing it in a special holder, like a small flat jewelry box), cleaned up the rest of the mess with a hand towel and allowed me to get dressed. "I can't go out like this!" I said, as I buttoned my uniform shirt. "What's the matter?" she asked, turning to view me in the mirror. She handed me a bright pink 'Sissy Store' bag which contained my newly manufactured bras. "The bra! It shows through the uniform shirt!" It was true. The light fabric of the uniform shirt clearly showed the outline of the bra underneath. Now everyone at work would know I wore a bra underneath. As would everyone I passed on the street... and on the looper... and the bus...!! "I think that, just maybe, that's what Ms. Jensdotter wanted all along," Creampuff said, giving me a kiss on the cheek. "It's part of your punishment." "What? How do you know?" "She sent instructions," Creampuff shrugged. "I'm sorry, my sweet Charlie. But I'm afraid it's time for you to go back to work." Creampuff dragged me from the dressing room, and joined by Suzi, the owner, gently, but firmly, led me to the exit. Just before I left, I left a tip for Creampuff on Suzi's tablet and a moment later found myself on the street. * * * Stepping off the elevator at the office, I just looked at the floor. My ears were burning and I dared not look anyone in the face. As I entered the main work area, I heard whispers followed by a deafening silence. Everyone could see what I was wearing underneath, and I could feel the eyes of the room follow me as I walked between the desks, down the center of the room, to my work station. I dared not look up, and focussed my eyes on the carpet and low-cubicle walls that made up the corridor, occasionally veering left or right when a pair of feet entered my narrow view. Finally I made it to my desk and sat down and started to work my way through the notes which had arrived while I was out. Gradually, the sounds of the office returned to normal. I turned to the wall for a second, fetching a tissue from the desk drawer. Tears squeezed out of my tightly shut eyes and dripped down my cheeks. I dabbed at my eyes trying to steady my breathing and my hands. A note flashed up on my tablets. ** Summons: Ms. Jensdotter ** I wiped my eyes and blew my nose, and still staring at the ground, got up and entered her office. "Yes, Ms. Jensdotter?" I asked. "Didn't I say that I wanted to see the bra as soon as you came back?" "Yes, Ma'am," I said, my voice quavering. "I was just about--" "You've been at your desk for five minutes," she interrupted, consulting her display. "Plenty of time to do whatever personal tasks you data processors need when you first arrive. Take off your shirt." "Yes, Ms. Jensdotter," I said, slowly unbuttoning my uniform shirt and revealing the sissy bra. "Wonderful," said Ms. Jensdotter. "You have made a very appropriate selection, Charlie. I worried that you might try and sneak by with something... shall we say... less frilly. Less Sissy? But I can see that you have accepted fully the spirit of your punishment and have selected something wholly appropriate." What was that? As she continue to praise my selection of bra, the jeweled plug in my bottom started to hum. It was distracting. "The bow in the front and the gathered lace is an especially nice touch," she continued. "Don't you agree, Charlie? Don't you agree that this is a beautiful Sissy bra to wear?" Of course, whenever a superior asks you 'don't you agree?' there is no other choice but to agree with everything they said. "Yes, Ms. Jensdotter," I said, with as much enthusiasm as I could muster. "It is a very beautiful Sissy Bra." The jewel in my bottom thrummed with pleasure. "And I bet you'll enjoy wearing it during your punishment period. Why, I bet that it will barely be any sort of punishment at all, wearing this bra." I knew I was supposed to answer her affirmatively, but I just couldn't. My shameful walk through the cubicles was still too fresh in my mind. The warming hum of my jewel stopped and was replaced by something cold which made me shiver. "Humph," Ms. Jensdotter snorted, sitting back and surveying me. "Still a bit of fight left, I see. Put your shirt back on, Charlie. Dismissed." "Thank you, Ma'am." * * * The rest of the day I kept my head down and didn't dare look up from my tablets. All around I could hear fresh whispers as new people would come into the room and see the bra outlined underneath my uniform shirt. I could imagine what they were wondering. 'Is he doing this willingly?' they wondered. 'Is he becoming a Sissy?' That would be the easiest train of thought. That I was a Sissy and had actually *asked* Ms. Jensdotter to wear the bra to work. A Sissy In Training. An S.I.T. A sitter. But I could also tell that there was another set of whispers. What if I was *not* doing this willingly? What if this was some form of new punishment? Is this why we were all given these new cheap nylon uniform shirts? So that they could punish us by making us wear bras underneath which would show to the rest of the world? How was I going to take the looper home? I fretted. Everyone on the street, everyone in the train... they would all just automatically assume that I was a sissy... Desperate, I tried to think of what I could do. My shirt! I opened up my desk drawer and breathed a sigh of relief. There it was, my dress shirt from when I was first issued my uniform shirts. I had left it in the desk! And so, before heading home, I changed from my uniform shirt into my old dress shirt in the men's bathroom, and it was 100x better. If you looked carefully, you could just make out the bra, but only if you looked very carefully and knew what you were looking for. * * * Back at home, I picked up the ingredients and made dinner. "And there's my naughty husband." I turned around and there was Cindy, fresh from work, standing in the kitchen doorway. "I'm so sorry," I said, rushing forward to take her coat and tablet. I hung up the coat in the closet and put the tablet on her desk and returned with a glass of wine. "Well, show me," she said, nodding. Blushing, I took off my shirt and put it aside, revealing my new Sissy Bra. Cindy saw it and just shook her head. "You were so close," she said. "It was your last day, wasn't it?" "Yes. But Cindy, Ms. Jensdotter had it in for me! She refused to let me go until I... I..." "You what?" Cindy said, with a hard edge to her voice. "Until I had lost control. She forced me into her lap--" "Forced you??" "Well not forced, exactly, but there wasn't a chair and she told me-- " "And did you think to say no? Did you think to fight her?" "It wasn't like that! I wasn't really given an option!" But Cindy just shook her head and tutted. "Here's what I think, *Charlie*. I think you were so hot and horny for your boss that you didn't really fight it. I think you wanted to be manipulated by her into losing control. I think she laid the trap and you willingly walked right into it. Just like what happened with Creampuff." "No! I would never do that!" "It all seems very suspicious to me. And now here you are, with another month's worth of probation." "Please Cindy, I'm so sorry! Please..." I was on the verge of tears. "Pull down your panties and then bend over," she commanded. With shakey hands, I obeyed. "So that's what it looks like," she said, awed, reaching out and touching the jeweled butt plug. It flashed a pink crystalline light at her. "It looks beautiful on you... in you, I mean." Cindy giggled. "Please, Cindy, I'll just take off this bra and I'll take out the jewel and then I can be your husband again--" "Stop! Charlie, you'll do no such thing. How much longer is your punishment?" "A month..." "Well then, for a month you'll have to wear the bra and keep the jewel in your bottom all the time, even when you're at home." "No! Cindy, please!" "Charlie?" Cindy said with a note of warning in her voice. "Yes?" I asked, meekly. "Do you really think I can have sex with you like this?" "What do you mean?" "Knowing that you're being punished at work. Punished for transgressions. Punished for loss of control." "But, it was not my fault--" "Stop. It most certainly was. I've talked to Ms. Jensdotter..." "You've--" "AND," she talked over me, "I've found her to be a very reasonable woman. Firm, yes, demanding, yes, but fair and reasonable. She told me that she even offered to put you on a milking schedule?" "Well, yes, but..." "Well, I think you should take her up on that. It will make it a lot easier for you to make it through the month, don't you think? After all, if you have one more instance where you 'lose control', then you'll be noticed and maybe fired, isn't that right?" "But..." I was going to say 'Only sissies are put onto milking schedules', but saying the words out loud felt dangerous, somehow. "Men don't get put onto milking schedules," I said. "Ms. Jensdotter explained that they have professional milking services right in the building and that, because of equal opportunity laws, they are available to men as well. Of course, real men rarely use them, but that doesn't mean that it doesn't happen. I was talking to one of the partners over lunch, and she said that at her prior job she had heard of a man being milked on a schedule. So you see, it does happen." "I'm sorry, but *no*." I put my foot down. "I'm not going to be milked like some... some..." I paused, unable to finish the sentence. "Just no. I don't need it." "Are you worried that if you do it you'll be breaking your wedding vows?" "Well..." "Oh, darling, that is so sweet of you! But just so you know, I don't believe that a sissy milking - as long as it's done by a professional milker in a professional setting - it's not breaking your wedding vows. Just so you know. Okay?" "Okay, but that's not the problem! The problem is I'm a man! And men don't get milked. We don't. *I* don't. I won't!" "Well, fine, have it your way. If you feel you can make it for a whole month without an orgasm, then..." she shrugged. "All I can say is that you need to take your punishment *LIKE A MAN* and then we can return to normal." "Yes, Cindy," I said, feeling defeated. "Now in the meantime,I know you'll be understanding when I say that I have needs as well, and there's a construction worker that I've had my eye on. I'm sure you won't object if I have sex with him while you're otherwise indisposed." "WHAT??" I shouted. "You can't be serious!!" "I most certainly am serious! Why should *I* have to suffer for *your* punishment? I've been for two whole weeks without an orgasm. Not like you! That's the longest since I turned 12! And why? Because of your mistakes!" "But... but... what about our wedding vows!" "What about them?" she asked, arching her eyes at me. I quickly ran through our vows in my head. As was typical for men these days, I had vowed to be faithful to my wife in mind and body and to obey her and support her in all things. After all, Women would have a much harder time of it - without guaranteed jobs like men have. And what had she vowed? She vowed to spend her life with me, and to help me when I needed help, and to accept me unconditionally with all of my faults and strengths. For the first time I realized that she had never vowed to be faithful. "Please, Cindy..." I was reduced to begging. "Lots of women are doing it these days," she said, "keeping a stud in the city. Our offices are being renovated and he's one of the construction workers, and I saw him looking at me the other day." "I can't believe you'd betray me like that." "Charlie," Cindy said, gently but clearly holding firm. "It's not betrayal. It's just sex. I will always love you and we will always be together. You are my husband. But I am a woman. I need to be free to satisfy my needs. You understand that, don't you? And when you are... like this, you're not doing your husbandly duty. I don't find you sexually appealing knowing that during the day you're wearing Sissy Panties and a Sissy Bra. You can understand that, can't you?" "What... what's his name?" I asked, feeling my face flush with embarrassment. "I don't actually know," she answered, giggling. "He's just a piece of meat. Seriously. Of course, a hot, muscled piece of meat that I can tame for my own purposes, but really, just a stud. That's all." "Cindy..." "Charlie! I'm not asking your permission. I don't need your permission. If you want a divorce, fine! Good luck finding another wife who will take you." "No! I don't want that! I'm sorry, it's just a shock, that's all." "Good. On the positive side, I've restored some of your porn rights. So if you want, you can view porn again. But remember that you are not allowed to orgasm without my permission. Sissy milking is fine, but jerking off - that's the worst violation of all. It's selfish and undisciplined and incredibly hurtful to me as you wife. You understand that, right Charlie?" "Of course I do!" I said, my head swirling at all of these new developments. "I'm a man. I understand my vows, and I swear I'll be faithful to you, Cindy." "Very good." And so we kissed and made up and I set the table for dinner. * * * After I helped Cindy get ready for bed, we snuggled for a while and then she went to sleep. But I couldn't sleep, I was too curious. She had restored my porn rights? So I picked up my tablet and started to browse. But it was all Sissy Porn! Nothing but Sissies being used and abused by their dominant wives and bosses and their male studs. Was that...? I shifted in bed, my bottom tingling. The jewel was emitting its warm hum again. I flipped through more porn, trying to find something which wasn't Sissy related. But the program forced me to look at each image for at least five seconds or watch the entire video before moving to another one. And if my eyes strayed away (or if I closed them), then the counter stopped! So I was forced to look. And if there was a video (there were lots of videos, but all of them short, like 10 to 30 seconds), I was forced to watch it all the way through. And all the time my anus hummed, making me horny in my Sissy Panties. My free hand went up to stroke a nipple through my new bra. When I finally got to sleep, I had horny sissy dreams of dominant woman. * * * Chapter 8: Mandatory Sissy Education "Why aren't you wearing your uniform shirt?" Cindy asked. "I... uh..." I had tried to sneak out the front door wearing my old work shirt. "Charlie?" "You can see the bra through the shirt," I explained. "I... I didn't want people to see it in public." "Don't you think that's part of the purpose of the bra? For people to see it?" "But Cindy!" "No buts. Take off that old shirt and put on your new uniform shirt. You're wearing it to work. And leave your jacket at home. It's too warm for that anyway. No arguments." Cindy snapped her fingers and pointed me back to the bedroom where I had to change. * * * "Anyone SITting here?" I looked up. A man was asking about the seat next to me and the woman looked on and smirked. "No," I muttered, hugging myself and turning to the window-display. The two settled into their seats as the doors shick-ed closed and the looper took off. "Is this a good place to SIT?" the man continued. "Do you like SIT- ing here?" "Roger, stop it," said the woman. Jesus, what an asshole. Of course I knew what he was doing, it was a common playground taunt, using the word SIT in every sentence to imply that someone was a Sissy-In-Training. "I'm sure she likes it," the man continued. "They all do. They like being humiliated by real men and women. Don't you?" He poked my shoulder with a meaty finger. "Please..." I mumbled, trying to make myself as small as possible. "Roger, stop. You're making the poor dear uncomfortable." "Look at you, no makeup? And that's a pretty manly pair of pants. Too bad we're in public. If you were *my* sissy, I'd spank some obedience into you." "Roger! You're going to get us into trouble. Stop this instant." "Yes, Janice," Roger said, finally leaving me alone. "Very good," said the woman. But then she tapped me on the knee. "You really could use a little makeup and a more feminine pair of pants," she told me. * * * People were staring and smirking at me all the way from the looper to the office. Everyone could see that I was wearing a Sissy Bra underneath the uniform shirt. As I walked down the street, I was passed by a woman who nudged her male companion and nodded back towards me. He snorted and licked his lips and they burst out laughing. They didn't even bother to hide it! It felt like my face would be permanently red I was so embarrassed. As I stood in the elevator up to my floor, I felt a finger tracing the bra straps down my back by someone standing behind me. I fidgeted but didn't move, not wanting to make a scene. Of course the elevator stopped at every goddamn floor, letting out one or two people at a time, so the finger had a long time to linger before I finally was able to get off. I looked back but everyone behind me just looked bored and un-interested so I couldn't tell who had done it. Damn. I hurried to my desk, trying to get there quickly before more people could see the bra visible underneath my uniform shirt. "Jamie?" I gasped, running into him. I looked at my friend, astonished. He was wearing a sissy bra too. "What happened?" "Well, Ms. Marysdau felt I needed additional incentive," he shrugged. "And of course I agree, after all I know that she's just trying to make me a better, more humble person and a better more hard-working employee." Jamie said all of this while staring at the ground. It was only after he was finished that he looked up and noticed that I was wearing a Sissy Bra as well. "Oh Charlie!" he said. I could tell he was sorry for me, but of course he couldn't say so out loud. "I see that you're being... helped... by your boss as well!" "Yes, Jamie," I said, reaching out and giving him a hug. "Lunch, later?" "Yes, definitely." * * * Rather than endure the patronizing looks of our fellow employees in the cafeteria, Jamie and I decided to go to a local restaurant for lunch. Unfortunately, the waitress didn't believe we were men and not Sissies, so we had to get pre-approval from our wives. Fortunately, they both allowed it. Once we got settled, I told Jamie all about my encounter with Ms. Jensdotter and how I had lost control and ended up in a Sissy Bra for a month. "So, why did Ms. Davis put you in a bra? Did you do something wrong?" I asked. "No! I didn't do anything wrong! My wife was nice enough to drain me every night, so I felt perfectly in control. Ms. Davis just called me into her office, told me that my punishment wasn't sufficient, and just ordered me to wear a Sissy Bra. It is so unfair!" Jamie suddenly realized he was still being monitored, even though we were no longer in the office, it was still office hours. "Or so I thought at first," he quickly amended. "But now I realize, of course, that she is perfectly correct. That I *do* need an additional punishment period to truly learn my lesson and become the best employee that I can be." I looked at Jamie with sympathy. "But what's worse," Jamie continued, is now my wife is upset. 'You must have done something wrong,' she keeps saying. I keep telling her to review my dstreams, but she keeps saying she doesn't have time. Anyway, the upshot of all this is that now she won't help drain me in the evenings. 'You'll just have to live with the consequences,' she keeps saying. 'No more help from me!' Charlie, I'm already so horny! Sometimes, I think I just need to go into the bathroom or some hallway someplace and, you know, take care of things? But I know I'll be breaking my wedding vows and I know my wife will be notified and probably she'll want a divorce and then I'll be thrown out on the street and then what will I do?" "Oh, Jamie!" I reached out and grasped his hand. "I understand. I'm in exactly the same boat. It took every ounce of willpower I had to last the first two weeks. I have no idea how I'll make it through an entire month." We sat like that for a while, holding hands. "Do you have a..." I nodded down towards my backside. "A jewel?" Jamie rolled his eyes. "Yeah. Ms. Marysdau is making me use it, and my wife says I have to wear it when I'm at home too. It's insidious, isn't it? I heard that the humming is actually an air compressor. And it does the cold blasts by releasing the compressed air out of small holes around the neck." "Like cold farts," I joked. "Yeah," Jamie laughed. "Cold, unpleasant farts." "Yeah," I squirmed a bit. "I'm actually having a hard time getting used to it. I mean, it just goes off at random times and when it hums..." "... I know," Jamie finished off my sentence. We got our meals (salads, vegetables) and ate them quickly. The time on our lunch-35 was running out. As we walked quickly back to the office, I brought up another subject that had been worrying me. "Ms. Jensdotter offered to sign me up for a..." I started, but I was too embarassed to say it outloud. "The... schedule? You know, the program?" Jamie suggested. We both knew what we were talking about. "Yeah." "Ms. Davis offered it for me too." "I don't want to do it." "Me neither... but..." "I know. These panties. The bra. The jewel... they're driving me insane. I'm worried..." "... me too." At the front stairs of the office building we just stopped and looked at each other. I could read the desperation in Jamie's eyes, and I'm sure he could read it in mine. How could we possibly maintain control without being on a milking program? But milking programs were only for Sissies. If we signed up for it... what did that mean? * * * Over the next few days, the workings of the jewel became clear. It would emit a warm, pleasing hum whenever I did or viewed something Sissy, and it would give me a cold blast whenever I tried to rebel. I began to dread having to take a shower, because that meant removing my Sissy panties and my Sissy bra, and I always got cold blasts whenever I did that. But fortunately, it gave me a long, warming hum when my shower was over and I put them back on. Also, it hummed whenever I touched my bra. How did it know when I did this? There must have been sensors in the bra which transmitted the information into my dstreams. I could tell that the jewel was getting smarter. It would randomly hum some times, but it seemed to be getting less and less random as the days passed. And of course how could I help but be horny? I defy anyone to not get erect while having a jeweled plug up your anus humming away during the day. It makes you squirm. It makes you think about being penetrated, 'back there'. It takes your mind of whatever you were doing to focus on your bottom. I found myself in the bathroom more and more, spraying cold water on my face and pouring ice water on my peenie. Once I found Jamie in there as well, doing the same thing. We couldn't grimace (the monitors would pick it up), but we could tell what he was thinking just by looking at his eyes. More than ever, I cherished the hours when I could focus entirely on work and data science. Data processing was able to occupy my brain so I could focus on just doing the best job I could and it would keep the sexual excitement at bay. As before, I spent every possible moment double checking my work, exploring new techniques, mashing up the data with public data sets, quadruple checking my work with additional regressions to verify things that I knew were correct. I even got compliments from Ms. Jensdotter on my new-found attention to detail. And after about a week, I thought: Okay, maybe I can get through this. Maybe I can handle it. But then I got 'educated'. * * * **Mandatory Educational Curriculum ** Said the note on my tablet. Apparently, Ms. Jensdotter had provided several interactive videos for me to view. Of course, mandatory training was nothing new. I had to do a ton if it when I first started the job to get up-to-speed on all of the endless policies and procedures. But I thought I was over that! I looked at my work queue. Was there something else I could be doing? But no. My work queue was empty. The only item I had on my queue was this 'mandatory education' assignment. There was nothing else I could do to put it off. I sighed and opened up the first link. ** On the Joys and Pleasures of Becoming a SISSY ** Oh god no... what fresh hell is this? Just the title caused a jolt up my spine. And in my peenie. On the screen was a sissy in an overtly pink, frilly 'birthday girl' outfit bedecked with bows, ribbons, and miles of tulle underskirt. She smiled at me, patiently, waiting for me to start the interactive training experience. I looked around to see if anyone could see me watching it. I tried to zoom out to make her image smaller so it wouldn't be so obvious but the zoom button was greyed out. I tried to lower the brightness of the screen, but it was stubbornly set to 'MAX' (making the pinks glaringly, almost painfully pink). I tilted the tablet towards the wall a bit and shifted my position, doing my best to shield the screen from prying eyes. Of course, tilting the screen that meant that my front was now exposed to the field of office cubicles which made up the main floor. This meant that everyone could clearly see my Sissy Bra through the gauzy uniform shirt. A (female) manager walked by and then swiveled her head to stare at my chest as she walked by, smiling to herself. I hid my face in my hands and took a couple of deep breaths. "Ready to start?" asked the Sissy on the screen. She was computer generated, of course, probably based on real a human template. As a computer automaton, she would patiently interact with me until the media experience was completed. The audio went directly into my implants, so I would be the only one to hear what she said. That was a small blessing, at least. "Yes," I whispered. It didn't matter how softly I spoke. The implants would pick it up. Sub-vocal controls was considered polite behavior in an office environment. Hi Charlie! My name is Butttercup! She waited. Shit, she wants me to respond! I closed my eyes for a second before responding. "Hi Buttercup." I am *so* glad to meet you, Charlie. As she spoke, the jewel in my bottom thrummed, but so slightly that I almost couldn't feel it. It was more like a tingle, 'down there'. "And I'm glad to meet you too." Yay! I just know that we're going to get on so amazingly *fabulously*. Now, as you may have guessed, Charlie, I am a Sissy, and I am here to tell you that I *love* it. Becoming a Legal Sissy is the best choice I have ever made in my life, and I am here to tell you my story. Charlie, have you ever thought of becoming a legal Sissy? "No, Buttercup, I have not." But why not, Charlie? Haven't you ever thought about it, maybe just a little bit? I squirmed. Of course I *had* thought about it. What male hasn't? After all, it's an option we all have, and every now and then you hear about a friend or the guy who lives two doors down, or your old roommate from your sophomore year who became a legal Sissy. "Maybe a little bit, but not seriously," I answered. I knew my answers and the correlating biometrics would be monitored. It would be best to be as truthful as possible. I thought so! [she giggled, winking at me] The jewel hummed away in my bottom. Damn it. I squirmed in my seat, flexing my bottom in response. I tried to fast forward, but standard media controls were disabled, including volume. I tried to look away, but the program monitored your eyes and automatically paused whenever you weren't looking at it with your eyes open. Shit. I took a couple of deep breaths and returned to watching. Oh Charlie, it will be OK, don't worry. [Buttercup held her hands to her heart and gave me an air kiss.] Like you, I used to be a man, desperately holding on to my masculinity. Like you, I used to tease my schoolmates with schoolyard taunts like they were S.I.T.'s or limp wristed or that pink was their favorite color. And I swore to anyone who would listen that I was all man, in every possible way, and that there was not even a little bit of Sissy in me. Buttercup looked down at the ground minute, feeling sad, before looking back up with a cute pout. But I was wrong. All my protests were just covering up what was inside of me. I am a Sissy, Charlie, I really am! It was just my male pride prevented me from seeing the truth within myself. It was just my dumb stubbornness which held me back from being truly happy and joining the Sissy Sisterhood and realizing my true place in the world. My proper place in the world. The place where I was always meant to be. As she said these words, Buttercup looked me directly in the eyes. Of course, she's just a computer simulation, but I understood the intent. I understood it perfectly. And the jewel continued to hum, driving me insane. How did I come to this realization, Charlie? Well, it was a process with many steps and many realizations that occurred to me over a period of months. It was painful and there were tears, but I am here to tell you that it was worth it. Yes, I had self doubt, yes I wondered if becoming a Sissy was the right choice, and yes I was worried and scared. But once I took the plunge and executed my change of status, I can honestly tell you that I feel like the happiest Sissy alive. And I want to tell you *all* about it. I want to tell you every last, fabulous pink detail. Okay, Charlie? Will you let me do that? Will you let me tell you all about how I came to realize that I was, truly and deep inside, a Sissy? And how I became, to the fullest extent allowed by law, a Legal Sissy? And how I came to realize what a special, wonderful, oh-so-satisfying experience it is to be a Sissy? Will you let me tell you all that, Charlie? I looked at Buttercup, incredulous. What is Ms. Jensdotter trying to do to me? I was completely at a loss. Why was she was forcing me take training on Sissy conversion? Why did I have to sit for this? Why was it mandatory? I thought about getting up and going to the bathroom, but my scheduled break wasn't for another hour. Of course, I'm allowed unscheduled breaks, but only three per week and I had already used two. I stared at the page for a while longer. Charlie? ** Mandatory training segment must be completed before end of the business day ** The note popped up on the screen. Great. So if I procrastinated and delayed, I'd have to stay until it was all read anyway. I looked at the clock. It was only 2pm. Three hours until the end of the day. I went back to the training. The first step of my journey was to learn to let go and just trust my wife and my boss. These are strong, independent, smart, college- educated women. Once I realized that they only had my best interests in mind, then I was able to open my heart to the possibility that maybe, just maybe, *what* they were saying and *where* they were leading me was what was something I needed to hear and where I needed to go. Trusting someone is scary. You put your life in their hands. And when they say things which are against your preconceived notions, it can take a while to listen with an open and accepting mind. But sometimes you just have to let go. Let go of who you think you are and say: 'I trust you. Lead me.' Once I learned how to do that, my life began to change... for the better. At this point, the training changed to question-answer mode. It would ask me questions and then record my answers, and I had to answer as honestly and truthfully as possible, since my biometrics were being closely monitored in lie-detector mode. Do you trust your wife, Cindy, to do what's best for you? And, of course, I had to answer by saying 'yes' out-loud. Do you trust your boss, Ms. Jensdotter, to do what's best for you? I said 'yes', but apparently the program didn't believe me (or it detected something in my bio-stream) because it asked several times and I had to say 'yes' each time before it was finally satisfied. As my responses got more and more confident, the jewel in my bottom would stimulate me more and more. Positive reinforcement. The questions continued, all along the same theme and asking roughly the same sorts of questions, over and over, until even I was convinced that I trusted my wife and my boss even more than I trusted my own feelings or, especially, 'unscientific, preconceived male- centric beliefs'. Finally, Buttercup continued: The second step of my journey was to admit to myself that I felt pleasure. Even when pleasure smacks you in the face, sometimes you just don't admit to it when it reveals uncomfortable truths about who you are. Let me give you an example. I am submissive. It was something that I have always known about myself ever since I first started browsing porn and had a wet dream where I was kneeling before a strong, dominant woman. But I always just thought to myself, "lots of men are submissive," and didn't think anything about it. After all, just because you're submissive and you get all hot and bothered by having a strong woman tell you what to do - that doesn't make you a Sissy, right? Of course it doesn't. But as I looked around at the construction workers, truck drivers, and athletes in the world I began to wonder. How many of them feel the same way that I do? Of course, we are all reporting to and taking orders from women these days, that's just the world we live in. But taking orders from a woman is entirely different than being sexually excited by a dominant woman. I am someone who, when she holds my chin in her firm fingers, causes me to melt with panting desire. And women who are wearing those old-fashioned, 1940's style victory suits with the shoulders and the pressed A-line skirts? Oh god! Just seeing one of them and I am reduced to a quivering puddle of panting desire. No, that intense *sexual* excitement domineering woman... if I were to be perfectly honest with myself... it felt wrong. It felt... unmanly. Real men don't feel that way. Real men don't feel so weak and small in the face of a woman like that. Real men don't feel weak and small... like a baby. Like a... sissy. Shit. I felt my pulse starting to race. I had to look away. I put my hand in my lap and tried to press on my hard member, trying to get it to settle down. Why was Ms. Jensdotter making me read this?? 'Perhaps she knows what's best for you,' said the voice in the back of my head. ** PING ** ** You must continue reading ** Damn it. I looked at the clock. Still 20 minutes before my break. Shit, shit! I read some more about how Buttercup found strong women to be so desirable and how she wanted nothing more than to curl up and be in their arms receiving their cooing attentions, 'like a Sissy,' she emphasized. But, of course, it's not just dominant women that turned me on. Not at all. In fact, I found lots of other things that turned me on which I should have questioned all along. For example, I always enjoyed giving my wife oral sex. A lot. If I were honest with myself, I would admit that I preferred it over penetrative sex, which was always so full of the stress of 'having to perform'. My idea of a perfect evening would be to make her orgasm with my mouth, and then to go off and masturbate. At the time I told myself that it was just because I was being a 'nice guy'. Isn't it wonderful that I care about my wife's pleasure, even more than my own? Isn't it great that I work so hard to make sure that she can reach her peak and how I put her pleasure in bed above my own? But is that what a real man would do? Wouldn't a real man want to take his pleasure from her? Wouldn't a real man prefer to actually *fuck* his wife, rather than always giving her a good pussy licking like a... ... like a Sissy? I stared in astonishment at the article. It was like he was reciting the events of my own life. Yes, my relationship with Cindy was based primarily on oral sex after which she would give me permission to masturbate as a reward. Of course we would have penetrative sex every now and then, but she certainly didn't seem to enjoy it as much. I had always assumed that it was because of how it stimulated her clitoris... but maybe there was something more to it? Perhaps she didn't enjoy it as much because... because of... Oh god, I was so horny! Shit, I looked at the clock. Just five more minutes. ** PING ** ** You must continue reading ** GOD DAMN READER! I silently swore, inside my head, at the stupid monitor which was demanding my attention. Fuck. ** You must continue reading ** Shit. Just five more minutes. I returned to the document. Because, Sissies love to please. We love to please *everyone*. We are happy, sexual beings which live to provide pleasure to both men and women. We love nothing more than snuggling up to a dominant woman and bringing her pleasure with our tongues and noses and lips. Hearing her gasp with pleasure because of what we are doing to her, because of the service that we are providing, because we are able to lick and suck on her pleasure button - when she pushes our head hard between her legs and squeezes - when we are forced to smell and taste and truly live inside *her* pleasure and *her* orgasm... Are you excited? Charlie? Does reading this make you all hard and sweaty? Is your heart beating? Do you feel like you might lose it at any second? Well, my name is Buttercup, and I'm telling you, Charlie, that I feel that way whenever I am with a dominant women. Sissies love to bring pleasure to others, in any way that we can. And not just with women, but with men too. After all, Sissies love pleasuring everyone. Men, women, and other Sissies. For us, giving pleasure is what fulfills us. Love and pleasure gives us purpose. It makes us whole. To be used for pleasure, to be the recipient and the vehicle for that pleasure. To be be owned and... Time for my break! Finally! I raced to the bathroom, and splashed cold water on my face and breathing hard. It took the whole break to settle down. * * * It was touch and go, but somehow I made it through the day. Buttercup spent a lot more time on the joys of serving people as a legal Sissy, and I had to grit my teeth through the descriptions of all of the ways that a sissy would provide pleasure to her owner and the people around her. And not only physical pleasure, but emotional pleasure as well. But then she veered off onto a new subject. Do you ever wonder about your place in life? This took me by surprised. She was drilling into topics that I hoped would remain unexamined. What is your purpose? What are you good at? "I'm good at data engineering," I mumbled. Yes, you're good at data engineering... Buttercup admitted. But aren't a lot of other men good at it as well? Aren't there lots of other men out there who would love your job and could do it just as well as you could? I shook my head. Now Charlie, you know the truth, don't you? Aren't there a lot of other men with your same training which could do your silly little DP job just as well as you? I said nothing. Now Charlie, you know you have to answer me. And I'll know if you're lying. You know that, don't you? Now tell, me... aren't there a lot of other men who could do your job just as well as you can? I fidgeted on my seat. She wasn't going to let up on this, was she? Charlie? "Yes..." I muttered, finally. Yes... what? "Yes, there are a lot of other men who could do my job." And just as well as you, isn't that right? "Yes," I admitted. That's right, Charlie. And how do you compare to your wife? How do you compare to your boss, Ms. Jensdotter? "What do you mean?" Well, do you have as much education as they do? Do you have as much responsibility? Do you make as much money as they do? "I... I don't know." Now Charlie, I can tell when you're lying. Tell the truth, dear. I thought about how Cindy had been through law school, and about what level Ms. Jensdotter must be at. I saw the degrees on her wall. And of course they were making more money. That's pretty much guaranteed for women in 2088. "No," I admitted. "I don't have as much education as they do. Nor do I have as much responsibility. I don't know how much they make, but I imagine it's more than I make." Would you like to know how much more they make? "No." Your wife already makes more than 5 times what you make. And Ms. Jensdotter makes almost 40 times your salary. I gasped. I had no idea their salaries would be so large! That's how much the world values their skills and abilities. Think, Charlie, how that compares to how much the world values your skills and abilities. That's quite a big difference, isn't it? "Yes," I agreed, feeling pretty small and insignificant. Now look around you, Charlie. Would it surprise you to know that you are paid less than everyone on this floor? "Really?" I looked around. "But... but... I'm a dedicated data assistant!" Yes, but you're also brand new. Everyone else has more seniority than you. They also negotiated their salaries, whereas you took your very first offer. "Why are you doing this?" I said, feeling tears rise to my eyes. Quickly I fetched a handkerchief and dabbed at my eyes, turning away so the others in the office wouldn't see me. Charlie, don't be sad. I'm telling you this because you need to learn your place in this world. Your place is not with men. You are not manly like construction workers or football players. You place is is not with women. They are smart and educated and hold the responsibility of the world in their hands. I know you know this... deep down inside. I hid my face in my hands, not wanting to admit the truth of what Buttercup was saying. Don't you, Charlie? "Yes," I said. That's right, my darling. But there is a place for you in this world. There is a place where you can contribute, have value, and have a purpose in life. There is a place where you can live a life free of heavy concerns of women and the crude posturing of men. A place where you can fully be yourself and devote yourself to beautiful things and beautiful feelings. A place of pleasure and service. I knew what she was going to say. But I just sat there, as Buttercup looked at me with her doe-like and caring eyes. Time's up, Charlie. We'll talk again tomorrow. Buttercup smiled and waved goodbye. * * * Chapter 9: My Wife has News "I'm home!" "Oh, Cindy, I'm so glad to see you!" I put down my apron and rushed to the foyer to greet my wife in the foyer. The training with Buttercup had rattled me, and I was glad to have some real husband-and-wife time with Cindy so I could re-assert myself as a man. I took Cindy's jacket and briefcase from her, put them away and then turned for a welcome home hug. "Oh!" I said, looking at her, surprised. "What?" Cindy asked, with a sly smile on her face. "You look... different," I said. "Radiant." Cindy grinned and tousled my hair. She really did look like she was glowing from the inside. Her face was flush and her hair cascaded down in wavy curls over her shoulders. Her normally buttoned-up blouse gapped open showing generous amounts of cleavage and lace bra. And she smelled... musky. "I did it," Cindy said. "Did what?" "I left work an hour early and found that construction worker I told you about. His name is 'Ed', by the way. I took him to a short-term hotel room and got the fucking I needed. And oh..." she closed her eyes in memory, "he is *so* good. Really. Such endurance. So strong. And so... firm." Cindy sighed and pulled me into a hug, only now I didn't want the hug! Even though I knew it was her right to seek out satisfaction if she needed it, it felt like betrayal. "Oh Cindy," I sobbed, feeling like a failure for not keeping my wife satisfied. "There, there, Charlie," she soothed. "I still love you. You're my soul mate. It was just nice to have a good thorough pussy pounding. You know... since you've been out of commission these last few weeks." "Was he..." I started to ask. "Was he what?" I wanted to ask if he was bigger than me, but I thought better of it. "Nothing," I muttered. "Come," she said, grasping me by the hand and leading me to the bedroom. Cindy sat down on the bed and pushed her high-heeled shoes off. "Take off your clothes, down to your bra and panties." "Uh..." I fidgeted. Something felt different. This was the first time she had every given me such a direct command. "Okay..." I stripped, carefully folding everything and putting it on the bedroom chair. I felt humiliated in my sissy bra and panties standing before my fully-dressed wife. "Our little peenie friend wants to come out to play," she giggled. My penis *was* hard, the little head sticking out from the sissy sleeve, framed by its lace collar. "Maybe Charlie likes to hear about how his wife was soundly fucked by a construction worker before coming home to work." "No..." I moaned. I desperately willed for my hard-on to go away, but it ignored me. I think it even twitched a bit. "Now Charlie, I really want you to be okay with my having sex with Ed. You know, it's just a physical need. You understand that, don't you?" "I... I guess." "And all of the ladies at work do it. You know how hard it is to be a lawyer, don't you? And so naturally I'll need some 'stress relief'. It's no different than seeing a massage therapist. He's just massaging... um... different places. Deep massage..." "Okay." I looked down at the ground, feeling lost and desperate. "I still love you." "Really?" I looked up, my eyes moist. "Oh honey! Of course I do. I will *always* love you, forever. Now, kneel down, because I have a special treat for you." "A special treat?" I asked, as I knelt. "Yes," Cindy stroked my hair affectionately and then pulled up her skirt, reached underneath and pulled her panties off her long elegant legs, tossing them aside. Her naked pussy and bottom were exposed as she sat on the bed in front of me. "Now lick me," she said. "Yes, Ma'am," I said, happy to be giving her pleasure like I always do. But as I got closer, something was wrong. The hair in her pussy was wet, sticky and matted. And as she clenched up, I saw a milky white ooze dribble out. "Cindy..." "Hush dear." Cindy put her hands behind my head and pulled me in to her crotch. "I need you to clean me," she said. "I need some of your special love. I'm sore, and so I need your tenderness. Please, Charlie." Ugh. She was rank. I stuck out my tongue and began to lick, gently lapping at her crotch. The taste wasn't too bad, no worse than normal. But the smell of male spunk was overpowering. "That's my darling," she sighed, pulling me closer and wrapping her legs around my head. 'I'm licking up another man's orgasm,' I realized. 'He fucked my wife, and now I'm cleaning her up.' "And swallow," Cindy instructed. I licked some more, going deeper this time, and then swallowed. Cindy lay back, confident now that I wouldn't pull away. "That's my darling," she sighed. "Ed said that I should make sure to have you do this so you could become a part of our lovemaking. He is so smart about these things. I guess he's fucked a lot of horny wives in the city with husbands at home. He says that it's best if everything's out in the open. No secrets. You agree with that, don't you?" "Mmm-hmmm," I said, trying to sound ambivalent while continuing to lick. "That's my darling Charlie," she said. "Well, how about this? I promise that no matter who I sleep with, no matter what man I fuck, I will always come home and tell you about it and I will always have you clean me up afterwards." I tried to pull away, but Cindy just closed her legs tight and pulled me back into her crotch, mashing my face into her pussy. "That will be my promise to you," she said, scooting forward and draping her legs down my back, humping my face with her pussy. "So that you'll always know exactly who I'm having sex with." "Mmmfff!!" I struggled, trying to get away, trapped. Cindy just used her legs to hold me in place, my face mashed into her sex. What should I do? I could fight harder, I thought. Why don't I? Be a man! Set some boundaries! Struggle more! Get away! But like always, after a minute or two, I gave in. I stuck out my tongue, slipped it deep into her pussy and continued licking. "That's my dear, dear, sweet Charlie," she sighed, relaxing, knowing she had won the battle, knowing how the force of her personality had triumphed over me. And as I continued to lick and such, gradually focusing more and more on her nubbin, gradually bringing Cindy to a nice, soft, flowing orgasm, I heard Buttercup (from my training) in my head. What is your place in this world? She asked. * * * I did not sleep well that night. My session with Cindy had made my peenie desperately hard. I tossed and turned, aching for a soothing orgasm but knowing that I wasn't allowed to have one. I went to the sink several times to splash cold water on my face, but I was only able to actually control my passions by standing in a cold shower for a good 15 minutes, coming out freezing and wretched. Why was all this affecting me so much? Of course my sissy panties were always a problem. They were maddening, stroking my peenie whenever I moved, and clutching at my balls and little head whenever I got hard. And the jewel. It kept humming and throbbing at all of the most unfortunate times. Like when I knelt down to lick my wife it was going off like crazy. But it was more than that. It was how Cindy's attitude was changing. Of course she always had a sense of entitlement - all women do - but since starting her new job she was becoming more and more confident, domineering and demanding. Rather than asking my opinion, she commanded me. Rather than suggest, she would tell me what she wanted and then she would expect me to follow and obey. It fed into something deep inside of me. My deep, submissive streak. But no! I could not be like that! I was a man, not a... not a sissy! I would not be forced to give up my rights and I was definitely not going to lose what little position I had in this world! But my hard peenie throbbing for attention, desperate for relief, and I tossed and turned, unable to sleep. * * * I slouched into work that morning, sleep deprived and emotional. I had 'borrowed' one of Cindy's old college sweaters to cover up my shirt and the bra during the commute in the looper, but it was too hot to wear in the office so I took it off and draped it over the back of the chair. I sat and adjusted my bra straps so they were comfortable. I tried to do it subtly so no one could tell, but I probably failed "Please god," I muttered. "Please let there be some data processing work on my job queue." But no, nothing. Nothing except more training videos. I fidgeted, not wanting to begin. Maybe if I just sat here quietly, then nothing would happen? Maybe it would all just go away? ** Continue your educational curriculum? ** The note flashed up on the screen. I sat staring at the note. I couldn't, I just couldn't. I knew if I clicked "yes" and started the training, things would go downhill... very, very quickly. Ms. Jensdotter popped into my heads-up. "Charlie?' she asked. "Are you okay?" "Yes, Ms. Jensdotter." "Then why are you just sitting there? Don't you have work to do? Education materials to attend to?" I could hear the smirk in her voice. "Yes, Ms. Jensdotter," I sighed. "Well, then, get to it!" Her video disappeared. ** Mandatory Educational Curriculum ** The interactive video popped up and this time it didn't wait for me to click "yes", it just automatically began. I was stuck. Charlie! Hi! It's Buttercup again. Did you miss me? "No," I said, softly. Awww... Well, *I* missed you. Are you ready to begin a brand new day of training on how to be a Sissy? "No. I don't want to take this training!" Well, I'm afraid I have to give it to you, But don't worry. I just know you'll love it! Okie dokie? Let's begin. Today we're going to talk about the actual steps it takes to become a Legal Sissy. And so Buttercup took me through the process of becoming a Legal Sissy. It was frighteningly easy. I needed my wife's approval and then I had to fill out an electronic on-line form and answer a few questions. And then after a two week waiting period, I would be a Legal Sissy. But don't worry, the law mandates that you can return to your formal status after a one year trial period. You will be allowed to change your mind and cancel your Legal Sissy Status. Buttercup explained. Well, at least that was encouraging. That if I did become a Legal Sissy, I would have a way to get out of it. Would you like to start a trial period right now? "No!" I said, a little too quickly and too loudly. Are you sure? "Yes, definitely." Well, you just let me know if you want to? Okay? And I will help you through the entire process. Just ask for Buttercup. 'Great,' I thought to myself. She's installed herself as a full-time digital assistant. That means she'll always be listening to what I say and all I have to do is ask for 'Buttercup?' at any time and she'll be right there, in my head, begging to help me become a sissy. It was a lot like sitting down at work next to a bowl of candy. Even though you're on a diet and you've sworn you will never have another piece of candy, it's right there and so easy to reach out and just take a bite... I shook my head and adjusted my peenie. God I was hard. "What's next?" I asked. Buttercup next went into the changes in status that would occur when I became a legal sissy. It's freedom. She began. Of course, first and foremost, it's the freedom to be who you really are, deep down inside. I know you better than you know yourself, Charlie. And this is who really are. "You don't know me, you're just a program," I muttered. Buttercup just ignored me. And freedom from worry or stress about your place in life or the need for survival. You'll be fully taken care of by your owner, or if your owner dies, by the state. This means you have free health-care for life, including as much plastic surgery as your owner will allow. You have a job for life. All of the administrative trivia of living will be completely take care of. You'll never need to worry about earning a paycheck, paying taxes, insurance, house payments, clothing payments, or any of that. Everything will be automatically taken care of for you and all you need to do is focus on giving and receiving pleasure. I squirmed some more. It sounded like heaven. And we sissies are a close-knit group. Don't think of this as losing anything at all, because what you'll be gaining is access to an exclusive club of Legal Sissies in your community. We organize sleep overs, makeup sessions, dress-up parties, and just social meetups because we just love being together. Doesn't that sound nice, Charlie? "Yes..." I muttered, before I could censor my words. Of course it does. Buttercup purred. I'm sure you'll just *love* it. You know that sissies are allowed unlimited orgasms? Women don't have the time and Men aren't allowed. But it's encouraged for sissies, because it leaves us in a state of happy orgasmic bliss and eager to please. I know how you already love seeing Creampuff. She's waiting for you, Charlie. She's just waiting to become your Sissy friend and lover. Imagine what sort of mischief you two might get into, if you spent the night together? Imagine what sort of mischief you might get into, snuggled in bed, naked except for sissy panties and bras, maybe even zipped up together in a Sissy Sack, little peenies sliding deliciously against each other, little nipples rubbing as delicious fingers find little crevices. Maybe there would be three-some? Three sissies in bed all exploring each other, little peenies up bottoms, three sets of hands stroking and pinching and thrusting... SHIT! I stood up quickly and turned off the screen, breathing hard, pounding on the desk, forcing my libido down with sheer force of will. I looked up and saw all of the other data processors in the room, staring at me. "Charlie!" It was Ms. Jensdotter, in person, standing by my desk. Clearly she was upset that I was taking an unscheduled break. "I'm sorry, Ms. Jensdotter. I... uh... need to go to the bathroom. Please!" "No," she said, bluntly. "You know it won't help, Charlie. You know what you need." "Please, can we go into your office?" "No, Charlie. Ask me here." I looked around at the open area. Everyone was pretending to work, but I could clearly tell that they were all looking at me with my bra clearly showing through my gauzy uniform shirt. Could they see my hard peenie poking out the front of my pants? My hands fluttered down, trying to (ungracefully and too late) hide the evidence. I knew what I had to do. It was an impossible choice, but there was no other option. If I didn't, all hope would be lost. If I did, at least there was a sliver of a chance that I could complete my probation period and get back on track. "Ms. Jensdotter..." I started. Suddenly my throat was dry. "Yes, Charlie?" God she looked beautiful in that tailored, starched pleated skirt suit and low-cut blouse. So confident and such a woman. She looked at me with her commanding eyes, knowing exactly what I was going through. "I would like to be put on a milking schedule," I said, softly so no one else could hear. "A what?" Ms. Jensdotter asked, mercilessly. "Speak up, Charlie, so I can hear you." I looked at her with pleading eyes, but it was hopeless. "A milking schedule," I said, a bit louder this time. The closest desks could definitely hear. I saw some shocked and embarrassed (for me) faces of the men working closest to me, and some general whispers in the room. "What about a milking schedule?" Ms. Jensdotter asked, much too loud. "I need... I need..." I faltered for a second, took a deep breath and closed my eyes. "I need for you to recommend me to be put on a milking schedule," I said, clearly. My face burned bright red. The room was dead silent. "Very well, Charlie," said Ms. Jensdotter. "I suspected you would need it. Some people just have no self control, but we can't help who we are, can we?" "No ma'am," I said, a tear leaking down my face. "Well, your place is already reserved. Go to the third floor. They're expecting you." * * * Chapter 10: The Milking Schedule "Welcome Charlie." I stopped and stared. The woman at the desk before me was a nurse. And old-fashioned, traditional nurse. I had read about nurses in stories and I had seen them in movies, but I had never actually met one in person. Forever ago they were replaced by computer terminals, but even that went away as Virtual Nursing Assistants would install themselves into your heads-up as soon as you stepped into a doctor's office or hospital or submitted to a care plan. But here she was. An actual nurse, looking at me through her black, cats-eye glasses (a black cord running behind her neck), as if daring me to come forward. She looked sharp, stern, severe, demanding... and beautiful. She wore an exaggerated old-style nurse's uniform, in all white and made of starched cotton fabric. The top was fitted and buttoned-up with a collar, two breast pockets, elbow-length sleeves, and turned- up cuffs. Her large breasts showed a glimpse of cleavage at the bottom of the v-neck collar framed in lace from her bra. Although currently hidden behind the desk, I imagined she also had on a white skirt (below the knee), white hose and white flats with practical rubber soles that would go "squeak squeak" on the linoleum floors as she walked. Her name badge, pinned in place just above her left breast, said "Nurse Hamilton". She looked at me with a no-nonsense expression. My jewel hummed at the sight of her. If there were any thought of perhaps canceling my milking for today, one look at her and I knew it was hopeless. I always had a thing for dominant woman, as far back as I can remember, and this nurse was a vision of control. I was much too horny now to let it go for even another hour. "I have some questions I need to ask you." Her voice was professional and no-nonsense, as if I were a boy who had been sent to the principal. "Okay." "Since you are new, I will let you off with only a warning," she reprimanded, "but be aware that the only acceptable responses for a pledge are 'yes, ma'am', and 'no, ma'am.' Alternatively, you can address me by my full name and title, which is "Nurse Hamilton". Do you understand?" Her scolding caused my heart to race. "Yes, Nurse Hamilton." Did this mean I was a pledge? "Now I have some questions to ask you before we get started. Be aware that your responses are being recorded in your permanent record. Do you agree to this stipulation?" "Yes, Ma'am." "Very good. What is your gender?" "Male," I said, confidently. "Uh, Ma'am," I added. I knew that if I was going to get through this ordeal, I was going to have to hang on to my male identity as tenaciously as I could. "That's it? Just male?" she asked. "Not Male Curious? Male Questioning? Male Exploring Sissy Potential? Male with Sissy Tendencies? Male with Sissy Leanings?" "No Ma'am," I pleaded. "Just male. Thank you, Ma'am." "Male Sissy In Denial," I heard her mutter under her breath. "Excuse me, Ma'am?" I asked. "Nothing. See?" Nurse Hamilton showed me her tablet. "Claims to be male." I sighed. It would have to do. "Do you enter the milking program of your own free will?" "Yes, Nurse Hamilton." "Do you understand that once you begin, milking sessions are mandatory?" "Mandatory? Uh... Ma'am?" That was not a word I liked. The jewel hummed merrily inside my bottom. "Yes, mandatory. You are required to attend every session on your milking schedule, or you will be assigned punishments as we see fit, which may include physical punishments, notifications to your owner, wife or supervisor, workplace sanction, public notice, financial penalty, or any combination thereof." Oh god. Suddenly this had become very, very real. I gulped. "Yes, Ma'am. I understand. Yes, Ma'am." The jewel in my bottom throbbed at my positive response. Oh god, I was so horny. I thought I might actually orgasm right there in front of her. I imagined how ashamed I would be if a wet spot started growing on the front of my pants. "Very good. Do you, Charles Pauline, willingly waive the right to terminate your participation in the milking program?" "Uh, what does that mean? Ma'am?" Having first-hand experience with my employment contract made me leery of waving my rights. The jewel gave me a small cold blast at my questioning response. "It means that only your employer or your wife or owner would have the right to terminate or modify your attendance in the program." I thought about it. I was pretty sure that Cindy would terminate the program if I asked her to. Also, if worse came to worse, I figured I could looking for another job and then the program would be terminated when I switched jobs. "Yes, Ma'am." "Yes what?" she asked, impatiently. "What are you saying yes to? Be specific, pledge." I shuffled my feet. "Yes, Nurse Hamilton, I agree to waive my right to terminate my participation in the milking program," I said, finally. "Very good," she purred. The magic jewel gave me an especially vigorous warm hum. I clenched up my buns, trying to cope. "That is very, very good. Now, I see that you're scheduled for twice-a-day milkings, at 10am and 3:30pm." "Twice a day?" I gasped, shocked. "Ma'am," I added, as an afterthought. "Yes," the nurse said. "Twice a day. This is usually the case for the first month or so. It helps ensure... compliance. Do you understand that you will need to report promptly twice a day at 10am and 3:30pm for milkings, no exceptions?" I looked at the floor and studied the patterns on the linoleum. "Yes, Ma'am," I said. "Very good. Now I need you to read this statement and ID yourself and then you'll be fully signed up." The wall behind the nurse lit up with the pledge. "I, Charles Underwood, have pledged myself to the CICI corporation milking program. I understand that I will be milked twice a day, every day at 10am and 3:30pm. I waive my right to termination on my own behalf and I understand that my participation is mandatory and that if I miss a session I will be subjected to penalties, financial and otherwise, and other punishments. I enter this milking program of my own free will. Further, I pledge to do my best to follow all instructions of my handlers and the staff immediately and without question, as I understand that this is in my best interest. Thank you." I reached out and tapped my wrist to her tablet and that was it. I was now formally pledged to the program. Nurse Hamilton reached into her side desk drawer and pulled out something lacy and white with pink satin bows. She stood up and walked around the desk and held it up to me. "This is your sissy pledge collar," she said, showing it to me." It was a flimsy collar with rows of lace and a soft pink ribbon down the center. Embroidered into collar was the words "Sissy Pledge" in cursive script. A small silver bell hung from a loop in the center. It had an electronically activated tongue-and-slot fastener in the back. "I have to... wear a collar, Ma'am?" my voice quavered. "Yes. As you know, milking schedules are typically for sissies. It's only recently that they've been opened up to men as well. The collar is required element which is a necessary part of the program. Any further questions?" The tone of her voice made it clear that no additional questions would be tolerated. "No, Nurse Hamilton, sorry ma'am," I gulped. "Very good, now hold up your wrist." Nurse Hamilton touched the collar to my wrist which activated the electronics and sensors and connected the collar to my personal data stream. She then snapped it around my neck. Small motors in the collar automatically cinched it tight to make a snug fit. It would be a constant presence around my neck, not suffocating, but always there and always slightly uncomfortable. Nurse Hamilton pulled out a length of pink ribbon which she clipped to the collar. "Come," she said, leading me by the leash into the corridor behind the receptionist's desk. The bell tinkled merrily with every step I took. She took me into a large changing room, but one which had been designed for sissies. All of the lockers were designed to look like French provincial furniture (light pink with gold trim), swags of pink and cream fabric and tulle were everywhere, and instead of benches there were pink satin ottomans. Next to every locker was a small dressing table with mirror and makeup. "Sissy Station Seven," said a voice in my ear. "This is your assigned Sissy Station," explained nurse Hamilton. A screen on the locker displayed my name and picture. "The system will try and give you this station every time, but it may change if we have a lot of Sissies that day. The station will be set up automatically for you." "Set up automatically?" I asked. "Uh... Nurse Hamilton?" I had thought I would just go into the milking station and drop my pants and get... milked by someone. Or maybe have to do it myself. This was starting to look like a much bigger deal than I expected. "Yes. You will be expected to change in preparation for your milking. The clothes are automatically sized and you will find them in your locker." Nervous, I opened up the locker and looked inside. What I found was a sheer, white gauzy robe with pink fuzzy marabou trim around the cuffs, hem, and neckline and a wide pink ribbon around the waist. On the floor of the locker was a pair of pink fuzzy marabou mules with two-inch heels. "I... No." I said, stepping back, horrified. "The robe was... too much. And the shoes. All fuzzy trim and sheer and satin ribbons everywhere. "I can't," I said, looking up at Nurse Hamilton. She looked at me amused. "Charlie, you agreed to follow all of the instructions of the staff, did you not?" "Yes, Nurse Hamilton," I quivered. "Does someone need a few strokes from the 'obedience rod?' ?" "No!" I gasped. "No..." "That sounds like a ye-es," she trilled reaching for a convenient rod with a leather handle hanging from the dresser. I looked around and noticed that every station had one. I tried to back away, but Nurse Hamilton pulled on my leash (the bell of my collar tinkled) and pulled it down, forcing me to bend over, my thin pants tight against my bottom. Through some sensor, the Sissy collar automatically tightened around my neck. I panicked it threatening to cut off my air supply. "There's no escape," Nurse Hamilton growled, twisting my wrist behind my back, holding me in place. She pulled back and gave me a vicious stroke on my bottom. Even through my pants and panties, the pain was searing in intensity. "Stop!" I screeched, desperately reaching back to stop her. "Please!" But Nurse Hamilton simply captured both wrists together in a vice- like grip and held them out of the way high up on my back as she continued to lay down my punishments. Unlike Ms. Jensdotter, Nurse Hamilton was a professional. Every stroke was delivered on-target. The pacing was slow and deliberate, designed to maximize the pain experience. But it wasn't so much the pain as it was the humiliation and how quickly it happened. God she was strong! No matter how I struggled, I never got even close to escaping. With the collar and the cane, I felt weak and powerless. "Stop!!" I wailed, breaking into tears. "Very good," she said, letting me up. Immediately the Sissy collar relaxed. "I think we've learned our lesson, now haven't we? That you'll always obey?" "Y-y-y-yes, Nurse Hamilton," I whimpered, wiping my eyes. She was breathing hard and looking at me triumphant with a glint in her eye. 'My god, she's enjoying this,' I realized. 'She'd be happy to do it all day long!' I reached for the robe. "What are you doing?" asked Nurse Hamilton. "Oh, such a silly sissy! You need to take off your blouse first! Hang it up on the hangars in your locker, like a good little Sissy. Sissy's are always very neat about their clothes." I removed my blouse and hung it up. "Now your pants. Don't you worry, Sissy, I've seen it all before," she said, reaching a hand out and stroking my bottom. "God how I love to break in in sweet new Sissies like you." "But I'm not a sissy," I murmured softly. "Of course not, dearie." "Leave on your Sissy Panties and Sissy Bra, since those are mandated by your owner... sorry... I meant your wife." Nurse Hamilton's smirk indicated she wasn't really sorry. Soon I was standing before her in just panties and a bra. Everything else was hung up in my locker. "I see someone is anxious for her milking," Nurse Hamilton said, pinching the tip of my peenie, still hard and stiff in it's satin sleeve. It bobbed out in front as if answering her question with a 'yes, please!'. "That's a cute pair of panties. My compliments." "Thank you, Ma'am," I mumbled, quickly reaching for the robe, needing something, anything, to hide my modesty. The robe was a gossamer thing of beauty, soft and sheer as it settled about my body. Unfortunately, it provided absolutely no coverage, as my panties and bra were clearly visible. The marabou trim around the hem stroked around my legs like a sensuous whisper. I pulled out the pink two-inch mules with the marabou trim and stepped into them, unused to the heels, I tottered a bit before finally getting my balance. "Now, I am here giving you my personal attention," Nurse Hamilton said, "do you understand?" Nurse Hamilton wrapped me up in her arms, pressing my face against her starch uniform, as her hands roamed freely over my satin covered private parts, stroking and tweaking. "Yes, Ma'am. Thank you, Ma'am," I gasped, trying desperately to control myself. Nurse Hamilton turned me to the dressing table mirror and I watched as she took advantage of my body. "Oh, you virgin sissies are just the most adorable," she said, grinning and watching my collar. "You stammer and gasp and squirm and it is just the most delicious display of sissy femininity. Don't ever lose that innocence, Charlie." "No, Ma'am. I won't Ma'am," I replied, unconvincingly, feeling myself fast approaching orgasm. Was this the milking? Was I finally going to get some relief? But as I looked, my collar flashed red and Nurse Hamilton let me go and stepped away. "Poo," she said, disappointed. "Well, you are a first-time sissy, I guess I shouldn't expect more than that." What the heck had just happened? "Please," I whined. Desperate, I reached for my own peenie, intent on finishing myself off, but Nurse Hamilton grasped my wrist and pulled it behind my back. "No, no, no!" she chided me. "Can't have sissy's playing with themselves or else milking parlors would go out of business! Don't you know the cardinal rule? No masturbating. Let's make sure you're kept safe from temptation." Nurse Hamilton pulled out a wide, pink velvet ribbon from a bundle of ribbons hanging next to the dressing table. Pulling my arms behind my back, she expertly tied my wrists together, positioning the large floppy bow so that I couldn't reach it. "There, all safe," she said, kissing me on the lips. "Now, let's take you to the waiting room." * * * Nurse Hamilton took me by the leash to a waiting room full of over- stuffed sofas and throw pillows. The walls were a rich red brocade and there was an actual chandelier hanging from the ceiling. Nurse Hamilton lead me over to a sofa, told me to sit, and then she hung my leash from a hook placed high on the wall behind me. I was trapped. With my hands tied behind me, there would be no way I could slip the leash from the hook, no way to unclip the leash from my collar, and no way to untie my hands. "Andy? Christeen? I'm sure you'll take care of our new pledge, now won't you?" For the first time, I saw two other sissies in the waiting room. One was dressed in a pink rubber dress, so skin tight it looked like it was painted on and below the knee so she could barely walk. It hugged every curve so that nothing was left to the imagination, including a pair of ample breasts with hard fat nipples. The second sissy was dressed in a long elegant party gown, cream colored, flowing with ruffles and firmly cinched-in bodice and covered with lace. Both were exquisitely made up with beautiful hair and makeup. "Of course, Nurse Hamilton," they both sang, getting up from their chairs and walking over to me. Andy's rubber dress squeaked and creaked as she walked, and Christeen's dress rustled deliciously as her long gown flowed around her legs. "Now remember the cardinal rule," said Nurse Hamilton. "No orgasms," they trilled in unison. "That's right, cheers, Charlie. Andy and Christineen, I'm sure, will keep you company until Madam Hardcastle is ready for you." Nurse Hamilton left, leaving me alone with the two sissies. "Your name is Charlie?" Andy asked, sitting down next to me. A strong smell of rubber washed over to me as she leaned in close to me and placed a gloved hand at my back, stroking it. "Y-yes," I said, bashfully. "Isn't that dress awfully hot inside?" "Yes, it is," Andy admitted, "but that's part of the attraction. You have to want it. The tightness, the heat, the compression... it's the whole experience. For me, the hotter the better." As Andy pressed her body against me, I tried to lean away, but Christeen was also pressing her body against me from the other side. I struggled, but with my hands tied behind my back and the leash attached to the hook on the wall, there was not much I could do. Andy grasped my chin and gently turned my head to face to her. The rubber of her gloves on my skin felt oddly perverted. My jewel thrummed. "You're so adorable," she said, licking my lips with the tip of her tongue. I felt her hot breath on my cheek. "So, ah... are you girls, ah... data engineers with PDI too?" "Oh, no," said Christeen. She slipped a satin-gloved hand into my sheer robe and stoked my bare leg with it. "We're models with the Sissy Modeling Agency upstairs. Sissy clothing is the fastest growing segment of the modern apparel industry, did you know that?" Christeen turned my head away from Andy. The silk satin on Christeen's fingers was smooth and cool. "Uh... no, I didn't," I gasped as she leaned in and gently kissed my lips with little kisses. "Well it is," she said, with a throaty whisper. "This year it will almost certainly outgrow men's fashion. It might even someday surpass women's fashion." "Wow." Andy undid my robe, pushing it aside to expose my sissy panties and sissy bra. "Nice panties and bra," she said. Andy gently squeezed one of my breasts and then pinched the nipple, making me gasp. "Very nice, especially for a *pledge*," she said, referring to the word 'pledge' on my sissy collar. "It's not like that," I protested, as the two sissies passed me back and forth, each one giving me little kisses or licks and then turning my head back to the other as their fingers explored inside my robes. "I'm a man, really I am. I'm just doing this to avoid punishment for an error I made..." "Of course, sweetie," Christeen said. "That's what I keep telling my aunt. But I think we both know the truth," she whispered into my ear, her warm breath making me shiver. "I have an idea!" Andy said suddenly, reaching for her purse (also rubber). Let's give Charlie a makeover! She has absolutely no makeup. And her hair! So blah! I bet she'd look just *adorable* with just a bit of sprucing up!" "What a *wonderful* idea!" Christine said, reaching for her (satin and lace) purse. "Now, Charlie, turn towards me -- don't pout! That is such an unattractive look for you -- and I'll cover up some of those small blemishes..." "Please no!" I whimpered. But there was nothing I could do, as the two passed me back and forth, each one expertly adding makeup. "We've had just *tons* of experience with makeup," Andy explained, brushing foundation onto my cheeks. "Of course, as models, we mostly have professionals do our makeup, but there's plenty of times when we have to do it ourselves," Christeen continued, adding eyeliner and eye shadow. "In fact, our company is coming out with a new 'sissy series' makeup line! It's a whole new line of especially bright and cheerful colors, specifically designed for sissies to make them beautiful and appealing." Andy continued with blush and then started to outline my lips. "And with the recent growth spurt in Legal Sissies, it's sure to be a huge hit. It's really a whole new market segment, Sissy Makeup. Considering how much makeup Sissies use," Christeen giggled as she continued to work on my eyes. How many steps were there?? "I bet it will be even bigger than women's makeup!" Finally, after a few more adjustments, they were finished. "Now, for the final touch," Christine pulled out a pink-lace hairband: it was one of those stiff half-circles, that she placed over my head, pulling my (longish) hair back and away from my face. "Oh... she's beautiful," Andy said, standup up and turning to look at me from a few steps away. "She is," Christeen said. "Charlie, would you like to see?" "No," I said, sourly, feeling like a painted clown. "Oh, don't be that way. Here," Christeen reached for my hand and tapped our two wrists together, "let me show you." Christeen projected her video into my internal heads-up and I could see myself from their perspective, and the image almost made me faint. What I saw was a teary, young girl, eyes wide, in her gauzy and fur trimmed nightgown and pink sissy underwear, hair pulled back with the pink hairband and the white and pink collar attached to the pink ribbon which went up to the hook. Her breasts and panties were barely exposed, as if teasing the viewer with her desires. She was vulnerable, sexy, beautiful, and oh-so delicious. "Th-th-that's me?" I gasped. "Yes it is!" said a towering, stern-looking woman standing in the doorway. She was dressed in stiff Victorian clothes, including corset and long skirt. She wore a high-necked, button up, cream colored cotton blouse with rows of narrow pleats up the middle. On her feet were mid-calf lace up boots with a chunky Victorian heel made of soft brown leather. She looked every bit the English headmistress. "You're wearing makeup, Charlie," she observed. "Yes... uh... ma'am?" "You may call me Miss Hardcastle." "Yes, Miss Hardcastle." "I see that makeup wasn't on your pre-preparation instructions, Charlie. Why are you wearing makeup?" "That was us," Christeen offered, giggling. "We put makeup on Charlie. Doesn't she look *amazing*?" "But with her consent, of course," Andy added. "She really seemed to like it and she looks soooo beautiful, don't you agree?" WITH my consent? I looked from Andy to Christeen, shocked. "But... I hadn't..." I started. "Yes, she does look beautiful, and I can see that you love it." Miss Hardcastle tugged on my leash to stop my objections. "You weren't supposed to start on makeup for another month, but I think we can accelerate that, don't you?" "Uh..." I said, stupidly. "The correct answer is 'Yes, Miss Hardcastle'." "Yes, Miss Hardcastle," I said, feeling trapped. "Very good, Charlie. Now wearing makeup without prior approval merits punishment. I believe that a paddling of 20 strokes should suffice." "Twenty!?!" I gasped, followed quickly by, "yes, Miss Hardcastle." "In the waiting room." "In here??" I cried, shocked, followed quickly with "Yes, Miss Hardcastle." Miss Hardcastle fetched a paddle from the wall. I hadn't noticed before, but the wall was decorated with a whole variety of spanking and caning implements. "I do love how new sissies squirm and shiver when they're getting their first spanking at the milking salon," Miss Hardcastle observed as she bent me over and handed my leash to Andy, who held it firmly in her squeaky rubber-gloved hand and tugged on it to make sure I was bent over, my hands, tied behind my back, my bottom sticking up in the air. The jewel throbbed merrily in anticipation. Miss Hardcastle pushed aside my sheer robes and, with a finger running between my buns, pushed down my sissy panties. "Oh, Miss Hardcastle," I moaned in fear. "All sissies are paddled on their bare bottoms, surely you should know that, Charlie." "I'm a pledge, Miss Hardcastle." "Pledges too. Now prepare yourself, Charlie." I looked at Christeen and Andy with pleading eyes, and although they looked back with sympathy, it was clear that they were not about to help. Miss Hardcastle placed the paddle on my bottom and rubbed it, then pulled back and gave me a nice hard spank. "Oh!" I cried. "Now, this is a sissy spanking," Miss Hardcastle said, conversationally. She lightly rubbed my bottom with the paddle each time before giving me the next stroke. "Hard, but not too hard. Just a nice Sissy spanking to make sure a sissy knows her place." "But I'm a pledge," I whined, mostly to myself. "Miss Hardcastle." Each spank was carefully calibrated with increasing strength to keep the sting at exactly 'sissy strength'. What I didn't know is that Miss Hardcastle was watching her heads-up display, transmitted by my sissy collar, which told her exactly how strong each spank should be. The spanks were not spanks for punishment, not really. Instead they were sissy spanks designed to feed into my sexual fantasies of submission. "It's okay to cry," said Christeen, placing a gloved hand on my cheek. "Let go," she counseled. "But... but..." I stammered, trying to hold it in as Miss Hardcastle delivered another swat. "You are so brave," said Andy, giving me a kiss on the lips and then running a pair of rubber-gloved fingers over my lips. "It's only us sissies here. Christeen and we always cry when we're spanked. Don't we, Christeen? So it's okay, Charlie. Let go. We'll fix your makeup when you're all done. We promise." "Okay..." I said, tears starting to down my cheeks. Just then, Miss Hardcastle delivered an extra hard spank which thrust me over the edge and I was truly and honestly sobbing. It was as much the pain as it was the whole experience of being dressed up and made-up and humiliated at work and at home... and then, the final humiliation, being spanked with bare bottom in a public place like a waiting room - treated like a naughty little girl... a naughty little girl who just wanted a good cry! "There, all done," announced Miss Hardcastle. "Now, was that so bad? Oh, there, there, Charlie. That wasn't so bad, was it?" "No... Miss Hardcastle," I sniffled. Miss Hardcastle pulled me into a hug to comfort me, my hard penis brushing up against her starched linen skirts, my stiff nipples rubbing against her ribbed blouse. As she hugged me I glanced over her shoulder and stiffened. Jamie had entered the room!! He was sitting on the far side of the waiting room, staring at me with wide eyes. He too was wearing a gauzy, marabou trim robe, and marabou slippers. I could see his baby blue panties and matching bra, both in silky satin, clearly through the almost transparent gauze of the robe. Like me, his hands were tied behind his back and his collar was on a leash which was looped around a hook in the wall above him. My face flushed bright red. Being made up and spanked in front of Christeen and Andy, two strangers, was bad enough. Realizing now that Jamie had witnessed it, made it 1000 times worse. Miss Hardcastle must have been notified on her heads-up, because she gently released me and looked over. "Friend of yours?" she whispered to me. I nodded. "Oh, how delicious," she said, wickedly. "Someone has a little sissy friend already." * * * Miss Hardcastle led me down a hallway. Everything was decorated in Victorian style with ornate wallpapers, Chinese rugs, wall sconces throwing out warm light through frosted glass shades, dark wood antiques with knobs and spindles and claw feet, crown molding and baseboards. It was like stepping back into an old home or fancy boarding school, even though I knew that this was all inside a modern office building. 'Has this always been here?' I wondered. Were these secret Victorian hide-aways hidden all over the place in office buildings around the city and maybe homes and strip malls all over the the United States? Always hidden to non-sissies and never even suspected by the men and women who walked past them every day? She opened a dark-wood door and ushered me into her study. It was heavily furnished with overstuffed sofas, a big dresser / armoire, a bed with an ornate canopy with heavy satin drapes dripping with lace and tassels, dark wood end-tables, book cases, and various oil paintings of sissies and stern mistresses with ornate gold frames. The paintings looked like they were human rendered, but it's impossible to be sure these days. I looked around, realizing the true purpose of some of the furniture. There was a set of standing stocks (with arm holes, leg holes and neck holes all padded with soft-velvet foam padding), a spanking bench with manacles to keep errant Sissies in line, some sort of peenie milking machine with tubes and jars (for catching sissy cream?) and what looked like a breast milking machine with suction cups attached to tubes. Did some sissies produce milk? Was that a thing? The thought made me shiver with fear. On one wall was an enormous floor to ceiling mirror with a large ornate carved wooden frame. It looked antique since the glass was slightly fogged from age and the silver was etched with cracks. In it I saw myself standing next to Miss Hardcastle. She was much taller than me especially in heels, her holding my leash and the both of us standing in the middle of this overstuffed, sumptuously decorated and fabric covered room. I still had my hands tied behind my back. The antique mirror reflected the scene as if we had stepped out of the pages of some sexy romantic bodice buster novel. "Oh, such a room of delights for sissies," Miss Hardcastle said, observing me. I realized with a start that some big data machine was probably analyzing the video from my eye-cameras and correlating it with my bio-metrics probably to determine what sorts of treatments turned me on the most. "Yes, indeed," continued Miss Hardcastle, "lots of things for sexually torturing my sissy during her milking sessions. "Oh, how delightful for you!" "I'm a pledge, Miss Hardcastle." "Of course, Sissy Pledge Charlie, you are correct, you have not ascended to full sissy status... yet. But that is merely a choice - your choice. Just say the word and I would be happy to initiate the proceedings." "P-p-proceedings?" I stammered. "Yes. To Legal Sissy status. Just let me know when you're ready. Not too long, I hope. Now look over there, what do you see?" "A... a door?" I asked, not sure if I was missing something. "Exactly. A closet door. And what do you suppose is behind that door? Why clothing, of course. Sissy clothing. A world of delightful sissy clothing for playing dress up. And we all know how sissies just *love* to play dress up, don't you?" "Y-yes, Miss Hardcastle." I gulped, looking at the door, my imagination running wild with what sorts of exotic outfits of taffeta, satin, lace, silk, elastic and nylon it might contain. "Oh, poor dear, you're dripping," Miss Hardcastle pointed, opening my sissy robe so that my poor peenie, in the panty sleeve with its little head sticking out, was dripping onto the floor. "Someone must be excited, hmm? Excited to try all of these lovely delights in my bedroom study?" "Yes, Miss Hardcastle," I said, shivering again. The evidence was clear. I could not deny it. "Well, you will have many days in the future for that, assuming, of course, that you graduate from pledge to full Legal Sissy. For today, I think, we give you a simple milking of your sissy cream, now follow me." Miss Hardcastle went to sit on one of the over stuffed sofas and pulled me onto her lap. My hands were still tied behind my back, so I was defenseless as she untied my robe and played with my nipples. "Oh, so eager, my little sissy pledge, so ready for her spurties." Miss Hardcastle whispered into my ear. She pinched the head of my peenie for emphasis. Miss Hardcastle reached to the end table where there were a large stack of satin covered towels. She wrapped one around my peenie. "Ohhhhhmmmm, Miss Hardcastle," I moaned, ready to spurt. But then she pulled it away! "I almost forgot," she said, devilishly. "Miss Charlie needs to do something for me before I can bring her the sweet relief she craves. Will you do something for me, my Miss Charlie?" "Yes, Miss Hardcastle! Oh, yes! Anything!" "That's my good little girl. Now what I need is for Miss Charlie to say: 'I love wearing my sissy underwear.' That's all. Can you say that for me, Charlie?" "I love wearing my sissy underwear?" I asked. "That's right." "I love wearing my sissy underwear," I said, this time as a statement. "That's my good girl," Miss Hardcastle cooed, wrapping my peenie with the soft spurties towel and gently stroking me, with very slow strokes. "Keep saying it, Miss Charlie." "I love wearing my sissy panties," I said. "I love wearing my sissy bra. I love wearing my sissy underwear." I said it over and over, not realizing that I was changing the words, in my delirium, my desire, my desperate need to spurt. And Miss Hardcastle encouraged me and kept stroking, going oh-so-slowly. "You want to wear your sissy underwear all the time," supplied Miss Hardcastle. "I want to wear my sissy underwear all the time," I said. "I love wearing my pretty sissy underwear. My cute, adorable sissy things." "They are so pretty and feel so nice. You love how they feel." "They are so pretty and feel so nice," I repeated, in a fog of desperate desire as she went slowly, keeping me just at the edge, no doubt consulting my biometrics on her heads-up. "I love how they feel against my peenie and against my boobies." "You want to wear them forever." "I love wearing my sissy underwear and I want to wear them forever!" I babbled. "Oh MISS HARDCASTLE!" I squealed. "That's my good girl!!" Miss Hardcastle encouraged, bringing me over the threshold, my legs kicking out. My long denied passions spurt forth, arcing across the room and landing with wet splats on the hardwood floors in front of the sofa before Miss Hardcastle used the spurties towel to catch the rest, expertly making sure that I didn't soil the sofa or her clothing. I spurted and spurted and spurted, lasting a good five minutes. It was the most intense and long lasting orgasm I had ever had. * * * "My goodness, Charlie, that was quite a mess you made," Miss Hardcastle said. "But then, I guess that should be expected of sissies... I'm sorry, sissy *pledges* that have been so long denied," she chuckled. Miss Hardcastle tossed the spurties towel into a basket of used towels and then fetched a second one which she used to squeeze my peenie with long strokes from the root to the tip, milking it of all of the sissy cream that it contained, capturing it in the towel which she added to the basket. "You did very well, Miss Charlie," she said, giving me a hug from behind and then nuzzling and kissing my cheek. She reached over and rang a silver hand bell, and almost instantly the door opened and a sissy maid walked in and curtseyed. "Clean this up," Miss Hardcastle indicated my spurts on the hardwood floor, "and then escort Charlie back to her station so she can get dressed and return to work. Now Charlie, one more thing, we've checked with your wife and she wants you to keep your Sissy Collar and makeup on all day long." "She... WHAT?" I gasped, suddenly shivering in fright. "Uh... Miss Hardcastle? Are you certain? That doesn't sound quite right..." My protests were interrupted by a video of Cindy which played in my heads-up. "Yes, I think that is a lovely idea. Definitely, Charlie should remain collared for the remainder of the day, and since her delightful friends went to such effort to apply such professional makeup to her - she really does look so lovely! - then yes, I agree she should wear her makeup for the rest of the day as well." It was irrefutable. That was Cindy. The video was digitally signed against her device for authenticity, so I knew it couldn't have been faked. But no... I couldn't... I would be wearing makeup and my sissy collar... in public? "What about the hair band?" I asked, tentatively, touching the pink hair band on my head which held my hair back. "What do you think, Charlie?" She asked. "I... I need to wear that too?" I shuddered. "Yes, I think you should, now don't you?" "I guess. But...." I was trying to voice some other objection. Everyone will think I'm a sissy, what will everyone in the office think?? "Charlie? Are we agreed?" "Yes, Miss Hardcastle," I said, my shoulders slumping. "We are agreed, Thank you Miss Hardcastle." * * * Chapter 11: Missy Chambermaid "My name is Missy Chambermaid," said the sissy maid as she escorted down the hall, our heels clicking musically on the hardwood floors, leading me by the ribbon attached to my sissy collar. "I typically work mornings during weekdays, so I expect that we'll see each other every day. If you need anything, just ask. Usually after the first time, Nurse Hamilton doesn't escort sissies to the waiting room, that will be my job." "Okay... Missy?" "Missy Chambermaid," she corrected. "Okay, Missy Chambermaid. Thank you, Missy Chambermaid." Already it was becoming second nature to follow every sentence with the full name of the person I was talking to. That was worrying. As we walked back to the changing rooms, I realized how exhausted I was. The milking had drained me not only of sissy cream, but of emotion and energy as well. As I click-clicked on my pink high-heel mules with the marabou trim behind Missy Chambermaid, I felt compliant and submissive. Accepting. Numb. If this happened after just one milking, what would I be like at the end of the month? Missy Chambermaid led me back to my station where she untied my hands. I put away the robe and shoes and got dressed for work (pants, translucent top and dress shoes). Missy Chambermaid watched as I changed. 'Why won't she leave me alone?' I wondered, annoyed. Makeup remover was right there, on the dressing table. If only I had a few moments to myself, I could tone down the look, but Missy was watching closely to make sure I behaved. "Don't you look lovely!" Missy Chambermaid exclaimed. "Selfie!" She threw her remote into the air where it hovered, about six feet away to take our picture. I saw the picture in my heads-up and grimaced. "Awww now, big smile, for me?" Missy asked. And so I did my best to give her a 'I'm-so-happy-to-be-here' smile and the picture of the two of us (me in my work clothes but made up and with my sissy collar and looking very feminine next to Missy in full sissy maid costume) was very much like all of the sissy porn I had been browsing recently. "Thank you," I said, once Missy had a picture she liked. "I'll just leave this here..." I moved to take off my hair band, thinking that if I could just make my hair look more masculine I might be okay. "OH NO!!" Missy said, with exaggerated horror, "You can't do that! It completes the whole look!! Besides, didn't Christeen give that to you as a present? Do you know how famous she is? She's practically like royalty in the sissy world! If she gives you a gift like a hair band, well, you wear the gift! With pride!" I fretted and fumed, trying to decide if I should try and press the point. "Does a certain little sissy need another spanking?" Missy asked, grasping my leash which was still attached to the collar. "Maybe we should do it in the public hallway? Or at your desk? I know where you work, Charlie." "No!" I said, hurriedly, shivering with fright. "I'm sorry, Missy Chambermaid! I didn't understand what a special gift this was from Christeen. Of course I'll wear it! I'm sorry for saying I wouldn't!" I said this last line like a cowed little girl, which I suppose I was. "That's better," said Missy, who was now all smiles again. "I know how hard it can be for pledges, but you'll soon get the hang of it." Missy lead me back to the front desk where she unclipped my leash (finally!), gave me a brief kiss on the cheek, and then, with a swat on my bottom, propelled me back into the hall and back to work. * * * As I walked to my desk, I did my best to keep my head up high and walk like it was no big deal, but I could feel the eyes of the entire office on me. And with my hair pulled back in the hair band and my face made up by Andy and Christeen, there was no place to hide. My face was burning red. Would people see how embarrassed I was through the makeup? How good was the concealer? Finally I reached my desk and sat down, staring intently at the tablets, not daring to look up. I touched my wrist to the tablet to authenticate. *** Come into my office *** I groaned, what now? I got up slowly and walked into Ms. Jensdotter's office. "You wanted to see me?" "Oh, yes," she said. "Come here, Charlie. Let me see you. I heard that Christeen and Andy gave you a makeover? Do you know what an honor that is? Of course, I wouldn't know, but I understand that they are two of the top sissy models in the business. Their owners must be raking it in. And look at you! So precious! I love the hairband. My, my, you are starting to look like a real sissy now." "Yes, Ms. Jensdotter. Thank you, Ms. Jensdotter," I said, trying to get this over as quickly as possible. "Come closer," she said, grasping my crotch as soon as I stepped within her reach. "Hard already?" she crowed. "But didn't you *just* finish with your milking? How much sissy cream did you spurt? I bet it was a lot." "Yes, Ms. Jensdotter. It was," I blushed. "Well, good for you." Ms. Jensdotter got up and pushed me against the desk. Her legs straddled my leg, humping it. "You're such a pretty sissy," she said, stroking my hair. "Why would you ever want to return to being a man?" "B-because..." was the only response I could think of. She ran a hand between my legs, groping my hard peenie in its sissy panties. "It's not harassment if it's hard," she whispered, stating the obvious. Of course, this was literally true since the courts recently ruled that female to male harassment did not exist if the man was sexually excited, as proven by an engorged member. This has led to regular abuse of men by women who make them do all sorts of humiliating sexual and debasing things only to fondle him to erection at the end of it thus 'proving' that he wanted it all along, and therefore it was consensual. "P-please, Ms. Jensdotter," I whimpered, just wanting to be out of there. "Well, fine, but only because I don't want to muss up your makeup," She lightly kissed me on the cheek and then licked my ear. Turning me around, she gave me two hard spanks on my bottom and then propelled me back to my desk. ? * * Chapter 12: The rest of the day I saw James for lunch. He was wearing a collar too, but no makeup. "Oh my gosh, Charlie! I was there when... you know... when I saw you with Christeen and Andy. I'm told they're quite famous! You should be... you should feel honored." "Oh yes, I am," I said, desperately trying not to cry and make a scene. After all, it would ruin my makeup which was so complex that it would be impossible for me to fix. James had also been signed up by his boss, Ms. Marysdau, for twice a day milkings, at 10:45 and 3:45. So we would probably be seeing each other in passing in the salon every day. "Where is this headed, Charlie? Do you think... are we going to be forced..." Jamie leaned close to me, "that we'll be forced to be come Legal Sissies?" he whispered. "I don't know," I said, dabbing at my eyes with a handkerchief. "I don't think my wife would want that." "Mine neither. At least I hope not." "And they can't make us do it without our consent. We have to legally waive our rights." "I know...." Jamie reached out and held my arm. "But I'm worried, Charlie. I'm worried that I'm actually starting to think about doing it. You know, committing myself." "Jamie, no!" "I know," he said. "But sometimes..." I thought back to my dream from the night before where I was with Cindy and Ms. Jensdotter and they were holding a tablet. The tablet said 'Charles Pauline has agreed to waive all of his rights and become a Legal Sissy'. The jewel in my bottom was humming and something was sucking on my peenie. "Just touch your wrist to the table and become a Legal Sissy forever," Ms. Jensdotter said. "We both know you want it," Cindy added. I had reached out my wrist, getting closer and closer... And that's when I woke up. I looked up at Jamie, and he could see the truth in my eyes. "Me too, Jamie," I whispered. We looked at each other, worried. "We just have to get past this month," I said, trying to marshal my courage. "Just one month of probation. And then we can go back to normal. Then we'll have proven to them that we don't want to be sissies. We just have to stick to our guns and not waive our rights." "I know," Jamie said. "I'm just starting to think..." "Starting to think what?" "Nothing," Jamie said. "Let's get back to work or we'll be late." * * * The rest of the day was more 'Educational Curriculum'. Basically this meant that Buttercup, my virtual teacher, continued to lead me through the ins and outs of life as a Legal Sissy. It was fascinating in a way, how much legal precedent had been developed around legal sissyhood. It was an extension of the 'right to waive one's rights' which had been established by the courts. Becoming a Legal Sissy meant waiving your rights to freedom and giving yourself and all your possessions (now and into the future) to your wife or owner. "The ultimate self-sacrifice," said Buttercup, proudly. "And in exchange for this sacrifice, you will be taken care of. Forever." The 3:30 milking was much less involved. This would turn out to be a pattern. A complex scenario for 10:30, and then a perfunctory milking for 3:30. This time, I was introduced to the 'automatic sissy milker'. Missy Chambermaid showed me into what was like an examining room and then Nurse Hamilton pulled down my panties and slipped a cylinder, lined on the inside with soft, puffy, lubricated latex, over my hard little peenie. The tip of the device was attached to wires and tubes and it sucked on my little peenie while I sat in Nurse Hamilton's lap and she kissed me on the lips and played with my nipples until my little peenie spurted. Oh so nice...! My sissy cream ended up in a glass test-tube which Nurse Hamilton set aside in a refrigerator 'for analysis and banking', she said. Banking for what? I wondered. After it was over I was forced to fix my makeup (with a quick lesson from Missy Chambermaid at my dressing table) and then sent on my way. * * * 'Everyone thinks I'm a sissy,' I thought to myself, fingering my sissy collar as I watched people stare at me as they entered the looper. My face burned red. I tried to turn up the collar on my blouse to hide the pink lace around my neck, but discovered that the blouse collar was sewn down. And so there was nothing to do but just try and ignore all of the attention and just get home where I could use some of Cindy's makeup remover to wash my face. I faced the wall, turning my back to the aisle. It had been a horrible, embarrassing day. Why had Cindy said I should wear makeup all day? Why had she said I should wear a collar all day? I fumed when I thought about this. I was used to Cindy taking advantage of me, and now Ms. Jensdotter. After all, I'm a man. Men understand that women run the world and in exchange men get guaranteed jobs protected from automation. But it still rankled. "Wearing makeup today, I see. Finally took my advice, I see." I looked up. It was the couple from before. All I could remember was that his name was Roger. "You look lovely, dear," the lady said. "Very pretty. Very feminine. Who did your makeup today?" "Two... uh... sissies. Named Christeen and Andy?" "*The* Christeen and Andy?" said Roger, suddenly interested. "I believe so? They were doing a photo shoot in my building today." "Holy crap! I didn't know they were in the city." "Roger browses a lot of sissy porn," his wife explained. I looked at her, uncomprehending. "Like a lot of wives, it's the only type of porn I allow Roger to browse," she explained. "He's always nice and randy for me when I need him, and it's not like he'd ever leave me for a sissy, isn't that right, Roger?" "Hell no," Roger snorted. "Exactly. So it's nice and safe." "You could be a sissy porn model," Roger said. He started stroking my cheek with his hand. The intimacy of his touch made my skin crawl. "You'd just need some tits and a better outfit." "This is my stop!" I said, suddenly getting up. "I don't think so," Roger said, grasping my hand and pulling me down into his lap. "I've seen you on this train a bunch of times, and you always get off after we do. That means you've got at least five more stops to go." "No, really, this is my stop." "Dear, I can tell that you're lying," the lady said. "And my heads-up confirms it. Now why don't you just sit quietly in Roger's lap. He won't bite. I promise." "But I'm not a sissy," I whined. "I have a wife. She won't like it if I s-s-sit in another man's lap." I was close to tears, but somehow I kept it under control. Roger put his arms around my waist and kissed my neck, pulling me more firmly into his lap. I felt a hard lump in his pants pressing against my bottom. Was that what I thought it was...? "Please let me go," I struggled to get up, but Roger held me firm. I think that my squirming had the opposite affect from what I wanted, rubbing my bottom across the expanding bulge in his pants. "She's a feisty one," he chuckled. "Now dear, settle down. Just give Roger his fun and we'll let you go when we get to our destination. No harm done." "No!" I protested. I struggled some more, trying to leverage my way out of his lap. "Settle down," Roger growled. "Or I'll be forced to lay you across my lap and spank you. Right here in public." "Sp-p-p-spank me?" I cursed myself that I couldn't get the quiver out of my voice. "Yes. Sissies like you need to learn their place and learn to obey their betters." "You really should listen to Roger," his wife agreed. "Please... no..." I whimpered, my eyes starting to overflow. "Oh now, Roger, look at what you've done. The poor dear is crying." Roger gave a big sigh. "Okay, I'll make you a deal," he said. "You give me a nice long kiss, on the lips! And then I'll let you go and you can get off." "A-a-a kiss?" I asked. "Yes. Either that or I turn you over and bare your bottom for a good sissy spanking. You choose." I looked back and forth between the wife and Roger, and they both looked at me with raised eyebrows. I looked around the rest of the compartment, but everyone else was pointedly staring away as if nothing unusual was happening. Why weren't they helping me? Couldn't they see what an outrage this was? It took a moment to sink in about what a horrible choice I was being given. A kiss or a spanking. All of this in public on the looper in a closed car with no escape. "A kiss," I finally agreed. "Good choice," Roger smiled a wide toothy smile. "Pucker up." I scrunched my eyes closed and puckered my lips, wanting to get it over with as quickly as possible. "Hey- -MMFF!" I gasped, my eyes wide open, as Roger grasped my hair and pulled me roughly to his lips. "Stopmmmff!" I tried to push him away, but it was too late. His rough handling caused me to gasp and cry out, opening my mouth and giving him the opportunity to thrust his tongue inside. "Mmmff!!!" I struggled and bucked, his fat tongue deep in my mouth now as he tightened his grasp around my waist and in my hair, tilting my head so I couldn't escape. "Mmmm, mhmm, mhmmm," Roger moaned, clearly enjoying himself while his wife laughed at my discomfort. I continued to struggle, trying desperately to push away and disengage myself, but Roger must have been in construction, because his meaty hands were just too strong. Worse, he was able to wrap his arms around me, hugging me tight to his body, as he probed with his tongue, deep in my mouth. With his free hand he reached down and grasp my bottom! His fingers dug into my ass, causing me to yelp and squirm even harder. I could hear his wife chuckling and goading her husband on. "Relax," she said. "Give him a real kiss and then he'll let you go, I promise." I struggled some more, gradually losing strength until finally, exhausted, I gave up. Roger took advantage of my acquiescence to kiss me in earnest, giving me multiple long kisses with tongue. "Kiss me back, sissy," he growled, before returning to kissing me. What could I do? I closed my eyes, opened my mouth and submitted. "There you go," Roger's wife purred as our kiss continued. "You've tamed another sissy, Roger." Finally he was done with me and let me go. I slipped back off his lap and into my own chair, dazed at what had just happened. I felt used. Humiliated. Embarrassed. Debased. Weak. Vulnerable. I looked up at the wife with watery eyes. "There, there," she soothed, patting my hand as they got up to leave. "You'll be just fine. Just doing your sissy duty is all. And I really must thank you, my dear. Roger will be a raging stallion tonight." * * * "Nobody likes a sourpuss," Cindy said, seeing my sour expression over dinner that night. "Especially not a wife who's had a long hard day and just wants to relax when she gets home." "Of course. I'm sorry, Cindy," I said. "But why can't I wash off my makeup?" "Because I don't want you to," she explained. "Now give me a smile. You know how much prettier you are when you smile." I did my best to shake off my funk and give her a nice, happy smile. "That's better. Now be a dear and tell me all about your day." And so I told Cindy about the educational training I was taking and how I eventually had to sign up for milking sessions, which she knew, of course, since she had to approve them and pay for them. "I must say that... what was their names again, dear?" "Christeen and Andy." "Yes, Christeen and Andy, they did such a lovely job. You look... absolutely lovely! I... I never realized just how pretty your bone structure was." "Thank you." "I honestly thought you'd last at least a few more days before starting your milking schedule," Cindy said with a smirk. "But perhaps you're enjoying wearing sissy clothes and learning about sissies a little too much, hmmm?" "No! I mean... I don't think so." "Your biometrics say otherwise, and they don't lie. What were you doing when you finally decided you needed sissy milking sessions?" "I was doing my educational sessions." "And what were you learning about?" I felt a hot wave of shame. "I was learning about becoming a Legal Sissy, from a virtual assistant." "That's what I thought," said Cindy, thoughtfully. "You know, Charlie, if you wanted to become a legal sissy, it would be okay with me." I stared back at my wife in horror. "Are you making me become a sissy?" I asked, tears springing to my eyes. "Oh, Charlie, of course not. It's just that..." "Just what??" My voice betrayed my anguish. "Well, if you *did* want to commit to legal sissyhood, then I just wanted you to know that I would support you every step of the way. After all, I wouldn't want to be the one to stand between you and your dreams." "Oh... Cindy!" I was crying in earnest now. "But dear, that's why we got married, isn't it? To support each other? I love you so much, and if being a sissy is what's best for you, then I just want you to know that all you have to do is say the word, and I'll make it happen. Okay?" "But you know that I don't want to become a sissy, don't you? I'm a man. I'm... your husband. Please, Cindy, you know that, right?" "Of course, dear! Of course I know that. But this whole experience had been..." She paused. "It's been what?" "Well, it's been very illuminating. For example, I never thought I would see you with makeup on and wearing a sissy bra under a blouse like that. And your sissy collar, it..." "It what?" "Nothing dear. I just wanted to say that we're both learning a lot about ourselves through the whole experience, and I think we should both keep an open mind to all possibilities. That's all." "Okay." I carefully dabbed the tears out of my eyes and settled down. "That's my good girl, Charlie." I sat staring at her, shocked. She had just called me a 'good girl'. But Cindy hadn't apparently noticed and I didn't want to make a big deal about it, so I just let it slide. * * * Chapter 13: The Dress The next couple of weeks settled into a routine. Every day at 10:30am and 3pm I went for my milking sessions, and each time I was more than ready to spurt. Mornings were usually Ms. Hardcastle, who would spank me and stroke my peenie me while making me say positive things about wearing sissy clothes or being a sissy. Things like: "I love wearing sissy panties!" "Wearing a sissy bra makes me feel so pretty!" "I love my milking sessions with Ms. Hardcastle!" "Wearing pretty sissy clothes makes me feel like a pretty sissy!" "I love being a sissy!" The sissy collar was "my" sissy collar, but thankfully Cindy wasn't making me wear it all day long after that first day. And so I carried it in my book-bag or pocket and then put it on before I stepped into the milking salon locker room. Every day I would approach the locker shaking with trepidation. What would I find? What would I be made to wear? But for the first week it was just the sheer sissy robe and the pink marabou trimmed mules like I had worn the first day. Each time Missy Chambermaid would tie my hands behind my back with a ribbon, then clip a second ribbon to my collar and take me to the waiting room where I was "hooked up, nice and safe", waiting for Ms, Hardcastle or Nurse Hamilton. It wasn't until the second week when I got something new to wear: a garter belt with stockings. Before putting them on, I had to go through a training session on "How to Wear and Care for your Stockings" where Buttercup taught me all about how to put on stockings (gathering them and then sliding them up my legs - which even I had to admit was a delicious feeling), how to attach the tabs (and looking oh-so-feminine while doing it) and how to check and adjust the seams during the day. The garter belt was a wide elastic belt of satin and lace which fit snug around my waist with garters made of silk ribbons and bows. In the training, Buttercup also went into the washing and care of the garters and stockings. 'Why would I need to know that?" I wondered. After all, the milking salon took care of cleaning and caring for the garments. I understood that they had quite a sizable staff (and growing) of sissy maids and laundry sissies. I found out the reason that evening. I was just finishing up dinner (pasta with a vodka sauce), when Cindy came up behind me and grabbed my bottom, making me squeak with surprise. "I see you have homework," Cindy said. "Homework?" I turned around to face her and we hugged and kissed. "Yes, homework from your milking salon." I blushed beet red. Literally the last thing in the world I wanted to discuss with Cindy was my milking sessions. They were a source of deep, deep shame. At home was the last place where I still felt (marginally) like a man and a husband. "I... I don't remember any homework," I stammered. "These two packages just arrived," Cindy said indicating two boxes on the countertop. "Open them." The first package contained a plastic bottle of depilatory cream, and a package of razors. "For your legs," Cindy read the instructions. "They want you to shave your legs every morning, and to use this depilatory shaving cream. Oh look, it's an 'all in one' with depilatory, hair growth inhibitor, and moisturizer all together. It should make your legs look nice and baby girl soft." "But I don't want my legs to be smooth and baby girl soft..." I said softly. Cindy looked at me with a strange expression for a second. "It's just until the probationary period is over," she said, finally. "Then you don't need to shave every morning. Unless you want to, of course." "Want to?" "You might discover that you like it," Cindy explained, reaching down and stroking my bottom, making me moan slightly. "See?" The next package contained about a dozen packages of stockings (all shades of pink) and several garter belts, all pink and white with lace trim and fancy ribbon bows. "Aren't these pretty!" Cindy exclaimed while I grimaced. And look, there's a note from the salon." Charlie: After consulting with Ms. Jensdotter, it was decided to upgrade your uniform. These are your everyday office stockings to be worn underneath your office uniform. I trust that you remember your training so you can properly take care of this beautiful new lingerie! If you have questions, you can always retake the training from your milking salon training page, or consult Buttercup, your personal MVA (Milking Virtual Assistant). Missy Chambermaid "A hand written note," Cindy said, amazed. "With actual pen and paper. I've only ever read about them in novels." * * * And so the next day I had to wake up 10 minutes early to shave with the depilatory cream and then put on garters and stockings. Fortunately, my pants were long enough to hide the pink stockings so no one could see, as long as I hid my legs under my desk as I worked. But the constant tugging by the garter belt and the feeling of the garter ribbons and tabs under my pants was a constant reminder of what I was wearing underneath. That day at my afternoon milking, I was made to wear pink socks. "Stockings *and* socks?" I asked. They had ruffled, folded-over tops which with a very small amount of lace around the wavy edges. "Yes, stockings and socks," Missy Chambermaid confirmed. "It's part of the standard sissy uniform." "But I'm not a...." I hesitated. "But I'm just a pledge," I said, finally. "And an adorable one at that," she said giving me a kiss on the cheek as I was lead to Nurse Hamilton's soft sucking tube. And so, my 'standard outfit' for milking sessions was this: My sissy panties, my sissy bra, the sissy collar, the sheer marabou trimmed robe and the pink marabou mules. After a week they also added a pair of long, opera length, pink gloves. In the mornings I would see Headmistress Hardcastle, where she would spank me with a rod and then kiss me and fondle me as I squirmed and said things like 'I love to be dressed in sissy clothes' or 'I love my milking mommies'. In the afternoons, I would be put onto an Nurse Hamliton's lap with the sucking sleeve and she would milk me for the second time. * * * "It's a dress," I said, taking a step back. "Isn't it beautiful?" Missy Chambermaid said, reaching into my locker and pulling it out. It was a fully Sissy party dress. The skirts were made of rows and rows of scrunched satin flounces and lace in various shades of pink and white which were super short, just barely long enough to cover my bottom and crotch (and not when I leaned over) The bodice was fitted and high-neck, with a wide flouncy pink collar. It had short poufy sleeves also trimmed in lace. "And see?" Missy Chambermaid reached into the locker for a second item. "It comes with these satin and tule ballerina petticoats! They'll give your skirts such luscious volume! Why, you won't be able to walk through a door or past furniture without your skirts bushing up against them." "No..." I shuddered, backing away. It was to much. Just much too much. "I'm not..." "Not what?" Missy asked, slyly. "I'm not a sissy!" I said finally, stamping my foot. I had already stripped I was naked except for my sissy panties, sissy bra, garters and stockings. My little hard peenie (trapped in the peenie sleeve and peenie collar) bounced up and down, ruining my statement somewhat. "Are you sure?" Missy asked, grasping my little hardness and stroking it. "I think you protest too much! You know what they say about people who say they're *not* sissies, don't you?" "But it's true. I don't care! I'm not... I can't... I... No!" I brushed Missy's hand away and crossed my arms over my chest in what I hoped was an attitude of immovable defiance. "But look, Charlie. Look at how delicious and sumptuous this is. Can't you imagine it wrapped around your body? Can't you imagine what it feels like surrounded all this fabric?" "I... no..." I had to remain strong. I was *not* going to give in! "But Charlie. You'll be such a beautiful sissy in your pretty party dress. Do you know that you'll be the very first sissy at this milking salon to 'come out' in your party dress? Don't you feel special? All of the other sissies will be so envious! You'll be the center of attention for sure!" I felt myself waver just a bit. The dress did look yummy. "I... I don't care. I don't want to be a beautiful sissy. I... I don't want to be the center of attention!" "Are you sure?" Missy said, holding the dress up to me. "Yes," I said, resisting the urge to reach out and drown myself in the folds. "I... I'm *not* a sissy," I stamped my foot again. "I was afraid of this," Missy said. "It's a common problem with our pledges, thinking that they're not sissies - although we all know they are, deep down in their heart of hearts. Well, I think I'll need some persuasive help." The mirror flickered to life. "Cindy?" "Hello Charlie. Your milk maid missy tells me that you are not following instructions." "But... Cindy," I hated the whining in my voice, but I couldn't seem to help it, "they're making me wear a Sissy dress. I... I can't! I won't. I don't need to. The... the milkings have been going just fine. Why do I... why do I have to wear a dress?" "Now Charlie, you know that this is all for your own good. I am paying for a top-of-the-line milking salon just so you can do your business twice a day and this disobedience is *very* disappointing. Very disappointing indeed." "But Cindy... it's... But why?!?" "I pay the salon to determine what is and what is not necessary, and I expect you to obey their instructions, Charlie. Are you experts in running a milking salon? Do you know how to crunch all your bio and vision data and vision data to come up with a long-term plan?" "I... no..." I admitted. "Everything they do is for a reason," she said, smiling at some internal thought. "And yours is not to question why, but simply to do as your told." "But Cindy..." "Enough Charlie! End of discussion! I expect to hear a glowing report on your cooperation from Missy by the end of the day, or don't bother coming home. I will lock the doors and freeze your accounts and you can sleep on the street. Do you understand?" I looked back and forth between Missy (with her superior 'I told you so' smile) and Cindy (with her stern 'the next word I hear from you better be 'Yes' ' expression). I felt tears dripping down my cheeks. "Yes, Cindy," I said, sniffling. "I understand." "And will you be a good girl and follow all your instructions to the letter?" "Yes, Ma'am." "Promise me. Cross your heart and hope to die." "Yes, ma'am, I promise. Cross my heart and hope to die." "Very good. Missy, can you take it from here?" "Oh yes, Ms. Pauline!" Missy looked over at me, smirking. "I can most definitely handle it from here." "Very good." The mirror blinked off. "Now now," Missy said, fetching a tissue and dabbing away my tears. "Everything will be fine, Charlie, you'll see. After all, you'll just be wearing it in the milking salon. We'll make sure you change into your uniform before you leave and no one will be the wiser." "Thank you, Missy Chambermaid" I said, accepting the tissue and blowing my nose. "Now, let's have you slip into this," she said holding the petticoats up. With my hands over my head, I dove into them. Missy pulled them down my body until they settled at my waist, the elastic hugging me intimately and sticking out from my waist, almost like a ballerina tutu, not hiding my pink stockings and garters at all. Next came the dress, which I stepped into. Missy Chambermaid held it open for me as I slipped my arms into the sleeves and I stood there obediently stood she zipped it up, the waist and bodice closing snugly about my body - trapping me in it's stain and lace embrace. The skirts stuck out almost sideways, fluffed out by the rows and rows of silky petticoats and crinoline. There was a big pink bow on my chest. The short cap sleeves ended in rows of lace. Next she put on a curly wig full of flouncy golden curls and tied a big pink ribbon in it across the top of my head with a bow on top. This was followed with my now standard opera gloves and a new pair of sparkly pink pair of pumps with kitten heels and big pink bows on top. "Now some makeup..." Missy said, quickly doing my face and lips and then applying an extra amount of blush giving me rosy little girl cheeks, "and a purse," she handed me a small pink purse with a long strap, "and we're done! That wasn't so bad, now was it?" "No, ma'am," I said, feeling small, girly and powerless. Missy tied my hands behind my back with a big pink ribbon and attached the ribbon leash to my collar. "EEEP!" I squealed as Missy Chambermaid reached under my skirts and squeezed my bottom though my panties! "Oh, that is such the best part," she said, huskily, as I blushed and turned away. * * * Missy Chambermaid continued to stroke and fondle my bottom while leading me out to the waiting room, until my collar flashed red indicating that I was right at the edge, when she stopped, leaving me panting with need. Missy Chambermaid led me over to a pole in the middle of the room. The waiting room was busy that day. When I first started my milking, there would be only me, or only one or two other sissies. Over the next few weeks, this grew until there were regularly six or more sissies waiting for their milkings, most of them I recognized as Data Processors from my office. She hung the leash over a hook on the pole. There was no place to sit, so I had to stand. I looked around, feeling awkward and out of place. I was the only one wearing a sissy dress. All of the others were wearing the standard marabou trimmed robe with marabou mules. They all looked at me with interest, some with envy. Were they looking forward to this same treatment? Others looked at me with fear, knowing this might soon be their fate. "Doesn't Charlie look just so adorable in her new party frock?" Missy Chambermaid asked all the sissies in the room. "And she just *loves* her new pretty dress, don't you, Charlie?" "Y-yes, Missy," I stammered, staring at the ground. "Of course you do!" said Missy, reaching a hand under my skirts and giving my peenie a pinch on the head. I 'eep'ed! In surprise. "Now it would be lovely if everyone here came up and gave Charlie a hug and a peck on the cheek," Missy said, "and congratulated her on her new dress. It's what sissies do, after all." Her smile was indulgent, but you could tell it was more of a command than a request. "I love your new party dress," said the first sissy, Kitty, as she gave me a hug and kissed me on the cheek. I could smell her shampoo and perfume. "Hi, my name is Sammi," said the next one, giving me a quick peck on the cheek and a squeeze around the waist. As she pressed her body to mine, I could feel her hard penis on my leg. The skirts of the dress were so pouffy that they scrunched up as we hugged. "I... I'm a pledge from the 4th floor. I think your party dress is very pretty." "And I'm Kandi Kane," said the next sissy, aggressively reaching under my skirts and grabbing my bottom as we hugged. "Maybe we can play together sometime?" She reached behind me and touched her wrist to mine, transferring her contact information into my address book. "Call me," she whispered, giving my ear a lick. "I'm jealous," said the next sissy, who's name was Pattie-kins. She pressed her crotch into mine and rubbed our peenies together, back and forth, making me blush and look away. "And you blush so prettily! I'm so lonely at home. Please come visit me! My mistress loves to have sissy visitors! Here's my contact," she reached around me and touched her wrist to mine. Each other other sissies and pledges did the same, each one rubbing their silky bodies against me with hugs and pecks on the cheek, and whispered nothings, leaving me panting and desperately horny by the time it was over. "Perfect," Missy said, staring at me, my eyes heavy lidded with lust. "Now remember this lesson, Charlie. All sissies just want to play." * * * When Ms. Hardcastle was finally ready for me, she took me in the back, and oohed and aahed over my pretty dress and shoes and pink purse with the sparkly trim. "Don't you look just like an adorable little sissy girl," she said, as she turned me to the full length mirror and reached under my skirts with a satin milking towel to grasp my peenie. "Yes," I admitted, looking at myself in the mirror. With my blushing cheeks, the curly blonde hair and the pink dress, I was forced to admit the truth. I looked like a girl. A little girl. "Tell me," she commanded, stroking me more firmly. "I... I look like an adorable little girl," I stammered. "And what sorts of men look like adorable little girls?" she asked. My peenie was hard and pulsing. "Sissies," I whispered. "That's right... sissies," she said. "You look just like a sissy, don't you, Charlie?" "Yes..." I whispered, unconsciously thrusting my hips towards her hand. "Sissy Charlie..." she whispered. "Sissy Charlie..." "Sissy Charlie," I repeated to myself. I turned and pressed my face into her bosom, holding her tight and shuddering as my peenie shot its cream into the towel. "That was fast!" Ms. Hardcastle laughed. "I think someone really enjoys her new party outfit! I think you'll be having lots more party dresses in your future," she added, winking at me. * * * Chapter 14: Makeup & Cock Sucking My humiliations that day were not over. "Sissy Charlie, this is Mandy Makeup!" Missy introduced me as she escorted me back to the changing rooms. Mandy was a bright and happy sissy with a twinkle in her eyes. "She's here to teach you how to put on makeup!" "Teach me...?" I looked back and forth between them. "Yes, teach you! But don't worry, Sissy Charlie--" "I'm just a pledge--" "Anyone can learn! And once you know how easy and amazing makeup is, why, you'll feel positively naked without it!" "I can't believe that you got a personal session with both Andy *and* Christeen," Mandy Makeup gushed. "We just switched to using Christeen's line of sissy makeup, and it is *so amazing*. She really understands Sissies in a way that the other brands can't match." Mandy then proceeded to train me on how to do my makeup. We sat down at the dressing table and she took me carefully through all of the steps of applying concealer, foundation, powder, blush, eye shadow, brow highlighter, eye liner, lip liner and lipstick. "Oh, you look so wonderful!" Missy Chambermaid said, when I was done. "I just know that your wife will want you to wear it all day!" I looked at Missy with a pleading expression. "What's the matter, Charlie?" she asked. "Don't you want me to submit a glowing report on how cooperative you've been today? Or should I call your wife to ask her opinion?" "No!" I said quickly, still smarting from the tongue lashing I had received earlier. "No," I added, glumly. "I am sure you are correct, Missy, I'm sure Cindy would want me to wear my makeup all day long." "Wonderful!" said Many Makeup. "So, then, I think you'll need this!" Mandy gave me bright pink bag containing a complete set of makeup ("all your own") to take home with me. "So you can practice at home and wear makeup for your wife," she said. Mandy then gave me a small bright pink purse (with a long thing shoulder strap) filled with 'travel makeup' so I could touch up my face during the day. "That way you'll be looking fresh and pretty all day long," she said. "Just like a sissy should." * * * As expected, once Cindy learned I was taking makeup classes, she wanted me to wear it all day long and every day. And since I was wearing makeup all day, I had to keep it neat and pretty all day long, which meant carrying a purse around with me wherever I went. As if I didn't already look enough like a sissy with the sheer blouses showing my bra! Now I had to carry around a pink purse slung of my shoulder as well. My face burned as I carried it into the office that first day. 'No one will ever think of me as a man ever again,' I thought, depressed. Of course Ms. Jensdotter loved my new look and took every opportunity to compliment me on it. "You look so pretty and friendly," she exclaimed. "I don't know why you haven't been wearing makeup all along. It suits you so well! Don't you think you look so pretty, Charlie? Especially with that pink lipstick and pink eyeshadow?" "Yes, Ms. Jensdotter," I said, because of course I had to agree with her. "I agree. I do look very pretty." But that wasn't enough for Ms. Jensdotter. She also insisted on endless "makeup inspections". Either by calling me into her office, or simply observing me through the tablet camera. Any imperfection would be pointed out and I would have to fix it *right away*! "After all, if you're going to wear makeup while being my assistant," she reasoned, "of which I heartily approve, then you will need to do it correctly. And that means making sure your makeup is always perfect. Do you understand, Charlie?" "Yes, Ms. Johnson." This was especially a problem because of my tendency to bite my lip when I was thinking. I got rid of that habit in a hurry! But no matter how careful I was, it seemed like I was endlessly fixing my makeup, no matter how careful I tried to be. "A sissy and her makeup..." I thought, thinking that must be what I looked like from afar, an office girl at her desk, staring intently into her compact mirror, making some small adjustment. And that first time I took a drink of coffee and saw my lip print on the porcelain rim... I just stared at it forever absorbing the fact that it was *my lips* which had produced that print! That was the first time I had felt entirely like a sissy while sitting at my desk at work. It was a serious "What the fuck" moment. The upshot of this was that I was constantly opening up my purse and checking my makeup. And since it occurred so frequently, there was no way I could take the time to walk to the bathroom to do it. This meant I was forced to fix my makeup at my desk, where everyone in the office could see. I would open up my pink purse and pull out my compact (I don't know why I couldn't use the mirror app on my tablet, but it had been disabled by IT-Ops) and then carefully check my face for any blemishes or crinkles which I would have to fix immediately, using tissue to wipe away problem spots and makeup to fix things back up again. All of this at my desk. With everyone on the office floor watching. Please God! Why couldn't you open up a hole to swallow me up?? Once everything was fixed, I would close up all of my tubes, return them to the purse, snap shut the purse, then hang it over my chair, out of the way. And every time, the jewel in my bottom would hum with pleasure. * * * "You're makeup is so pretty," Nurse Hamilton observed during my 3pm milking. "It's good for a sissy to always make sure her makeup is absolutely perfect." "Yes, Nurse Hamilton, thank you, Nurse Hamilton," I said, meekly submitting as she slipped the milking sleeve over my peenie and turned on the milking machine. The lubricated soft rubber sleeve gently sucked my peenie like a real pair of sissy lips. "Now Charlie, it's time you met your new boyfriend," Nurse Hamilton gave me a wicked smile. "Voila!" Nurse Hamilton pulled aside a curtain to reveal an anatomically correct male robot. "Now, fetch a pad and kneel before him and let's get started, shall we?" Oh god. I stood, frozen to the spot. "His name is 'Robert'," Nurse Hamilton offered, as if that would make a difference. I was in my pretty pink sissy party outfit, with my satin opera gloves, sissy collar, golden curls, and full, pouty makeup. The skirts brushed softly against my thighs. I could feel the garters tug on my silk stockings and my bra straps on my shoulders. My peenie in its peenie sleeve twitched. "Oh, you sissies," Nurse Hamilton tsk-tsked. She fetched a thick foam-rubber pad (with a soft terry cloth cover) from a stack against the wall and placed it in front of the robot. She then pulled me by the leash, down towards the ground, until I was forced to kneel in front of Robert - the male robot. Oh shit, his member moved! "It's just a robot," Nurse Hamilton said, caressing my shoulders. "It's not a real man. And it's just the two of us in this room." But still I just knelt there, not moving. It was a male robot, with an anatomically accurate penis, just inches away from my face. No, no, no!! "Let's start with just a little kiss, shall we?" Nurse Hamilton said, reasonably. Fetching another pad, she knelt down beside me and held Robert's soft rubber penis towards me with one hand and then with the other pushed my head forwards, until my lips touched his member. "There, now that wasn't so bad, was it?" The skin on his penis was surprisingly soft and... skin-like. Not like real rubber at all. And the smell, there was a slight rubber smell, but only very faint. Oh shit, the robot penis jerked. Oh shit. Oh shit. "Now, how about a kiss right on the tip?" Nurse Hamilton held the robot cock and pointed it directly at my lips. I stared at it and then looked over to Nurse Hamilton and back, feeling my heart sink. It's hard to communicate how dependent and submissive you feel in a sissy party dress with full makeup, stockings and with your hands tied behind your back. At least it was just a robot and not an actual man, right? I puckered my lips and put a kiss right on the tip of the member. "That's my sissy," Nurse Hamilton cooed. The jewel in my bottom throbbed with pleasure. 'It's just a robot, it's just a robot,' I kept telling myself as Nurse Hamilton had me place my lips around the circumcised tip and gently suck it into my mouth. 'Not at all like sucking off a real man." Because if it had been a real man and I enjoyed it... But no, I didn't want to think about that. That day, Robert kept his hands to himself as Nurse Hamilton coached me. She had me look up adoringly into his eyes as I took his rubber cock into my mouth, sucking it deeper and deeper. That first time didn't take long. With the milking machine on my peenie and Robert's cock in my mouth, my lips and tongue sliding over his hard fleshy pole, it wasn't long before we both orgasmed, me into the tube and Robert into my mouth. And ugh, he tasted like man sperm. Salty and viscous. Nurse Hamilton held my head in place so I couldn't pull away. "Take it all," she whispered into my ear. "Swallow it like a good little sissy." I whimpered and struggled, as Robert's robot cock continued to twitch and spurt, filling my mouth with his fake seed. Finally, both he and I had finished spurting. But Nurse Hamilton wouldn't let me go until I swallowed it all, and then opened my mouth to show her that it was all gone. And then I had to take his penis and clean it up, sucking on it some more to get out all of the remaining sperm and then licking any drops that remained on his penis or his balls. "Such a good sissy," she said. "Now that wasn't so bad, was it?" "No, Ma'am," I said, but only because I knew it was expected of me. "Of course not. Because you're a natural-born cock-sucker, aren't you?" I didn't answer. Her words were like an knife in my side. Unfortunately, that wasn't the first time I would have to kneel before my new 'robot boyfriend.' Practically every afternoon at 3 in the afternoon I would be kneeling in front of him, getting more cocksucking experience. And Robert was more than just a passive cock. After that first time, he became more animated with moving hands and moving hips. And everything was synchronized. The robot would groan and I would feel his hands on my head as he thrust his hips forward, driving his cock forward down my throat, and this would be synchronized with the peenie tube which would be sucking and rippling down the length of my poor, excited peenie, and the jewel in my bottom which would be humming merrily away. Typically, Robert and I would orgasm at the same time, his cock jerking and pulsing as warm salty liquid was shot down my throat. But sometimes I would come quickly and then be forced to continue the sucking until Robert was finally satisfied as well, which might take another five or ten minutes. To add to the indignity, after every session I was scored against several metrics (enthusiasm, energy, depth, teeth avoidance, amount of skin contact, amount of eye contact, amount of gagging, etc.) and I'd receive little 'cock sucking badges' whenever I received a new high score in oral performance. And every few days I would 'level up' which meant that Robert would have a slightly larger cock for me to suck the next time. There was even a 'highlights reel' that would play in the dressing room mirror as I changed into my office clothes. It would point out where I lost points and give me recommendations on how to improve my technique for future sessions. I never spoke of my cock sucking lessons to Cindy. I imagined that she must have known about it, she was paying for everything after all, but she never mentioned it. * * * Cindy did see my purse, however, since I was required by Ms. Jensdotter to take it home every night. "No personal effects are allowed at your desk overnight," she smirked, reciting long-standing company policy. Seeing it, Cindy insta-bought a small pink wallet to match the purse. "No need to carry your book bag back and forth anymore," Cindy reasoned. "Now all you need is your purse." "But..." I tried to argue. I had been hiding the purse in my book bag so it wouldn't show on the looper as rode to work, but Cindy made it clear that I had to use my purse from now on, no matter where I went. To make sure I was behaving, she took my book bag away and gave it to charity. Cindy further demanded that I continue using makeup even when at home. And so I had to continue to maintain my makeup in the evenings while making and serving dinner, only taking it off before going to bed, and then I would have to reapply it in the morning, after serving her breakfast and after my morning shower. Which, of course, meant I was fully made up whenever I traveled to and from work, having to endure the stares and comments of the other people on the bus and the looper. "Weekends too?" I asked, shocked. "But you look so pretty," Cindy said. "I know that when your punishment is over, you'll go back to being boring old Charles Pauline, but for now, yes, I want you to wear makeup on the mornings too. So I have my pretty little Charlie serving me and brightening up the house as the chores get done." I sighed. My last respite had been taken away. * * * As the days passed, I noticed changes in the office. I saw more and more men wearing bras underneath their sheer office shirts. 'Serves them right,' I thought smugly to myself, thinking about all of the stares and whispers and snide comments I had heard when I first appeared wearing my bra. Later, I could tell many of them were wearing makeup too. Once, when I sat down to review a dataset with another data processor, I saw his eyes go wide and his jaw clench up. He shifted nervously in his seat, looking at me as he tried desperately to concentrate on a new correlation technique I was teaching him. When I heard a soft humming, I understood why. He had a jewel thrust up his bottom, just like me. I smiled at him with sympathy and reached out to squeeze his hand for reassurance. But he jerked his hand away and glared at me. 'I'm not like you,' he snapped in a terse whisper. But behind his angry, red expression I saw something else. Worry. And doubt. * * * Chapter 15: The Second Punishment Period is almost over It had been three and a half weeks and *thank god* there were just a few more days until my probation was over. The whole time I was insanely attentive to Ms. Jensdotter, making sure to triple check all my work and to carefully take notes on every last procedure, every last analysis, every last correlation & quality check, so she would have nothing to complain about. My track record was perfect. "You have learned what it takes to be my assistant, I think," Ms. Jensdotter said, admiring my latest work. "This work is very well done." "Thank you, Ms. Jensdotter," I said, feeling fidgety but trying my best to sound humble and submissive like I knew she wanted. My mid- afternoon milking session was coming up, and I could feel my pulse start to quicken as my body looked forward to its second daily release. "You say that you noticed a correlation with one of the global databases?" "Yes. I realized that if I paired the F&G columns they made a two dimensional coordinate system which correlated well with GD-12-A1895. This allowed me to increase the R-squared to 0.8523. It seemed too good to be true, so I triple checked the provenance and there's no cross contamination, as far as I can tell. They are completely independent, and yet they reinforce." "Indeed they do," Ms. Jensdotter said, staring intently at the data and quickly flipping through the analysis with an expert's eye. She looked up a column, studied it, and then looked at me, with a weird expression. "Very interesting indeed," she said, going back to the table and checking other rows. "Yes, very, very interesting and very helpful. Why Charlie, I believe that you may have actually put us over the line. You have found the path to achieve our goal!" "Wonderful!" I said with forced enthusiasm. Of course I had no idea what that goal was. All of the data was heavily obfuscated and anonymized. None of the data processors, myself included, had any idea what we were working on. Theoretically it could be anything from patterns of fish in the ocean to supply chain product quality tests. But I did have a sense that it might, at least in part, contain data about population demographics. It was hard to know for sure, but there were clues. For example, in some data sets I found pairs of numbers that were clearly coordinates on a grid, and then I found that the correlations improved if I mapped the coordinates to a sphere, like the earth. Then you're like, oh, I bet they're latitude and longitude numbers. And then you start checking clusters against urban areas, and soon you're able to orient things. "Yes, excellent work," Ms. Jensdotter said, muting her screens and motioning me to come over. "Now let's talk about your future, Charlie," she said, grasping me around the waist and pulling me into her lap. "Ms. Jensdotter!" I squealed, remembering what happened last time. "What are you doing?" "I know you only have a week left in your probation," Ms. Jensdotter grasped me firmly about the waist and began to unbutton my blouse, "and over the last few weeks you've gotten a taste of what it's like to be a sissy." She undid the last button of my work blouse and pulled it apart revealing my lacy sissy bra. "Please Ms. Jensdotter..." "Oh hush. I won't bite. I promise. Not this time." "Okay..." I said, my voice unsteady. "Look at this," she flicked with her hand and an application form for becoming a Legal Sissy swiped onto her screen. "Please, Ms. Jensdotter..." I struggled to try and extract myself, but she held me firm. "Tell me, Charlie, are you enjoying your milking sessions?" I squirmed as she tweaked and played with my nipples through the bra. "They're okay, I guess." "Just okay?" Ms. Jensdotter snorted. "I've seen the data. I think they're more than just okay! I've seen how your heart rate and perspiration increase as your times get closer. I've seen the reports of your sessions." "You've seen my session reports??" I gasped. "Yes, of course. Your wife graciously opened that portion of your file for the company. Now admit to me that you love your sissy milking sessions." "I... I..." "Charlie?" I struggled with what to say. She would know if I was lying, but I couldn't think of a good half-lie to divert the question. "Yes, Ms. Jensdotter. I love my sissy milking sessions," I finally admitted. "Yes, I know you do. Did you know that sissies can be milked whenever they desire? Not just on a schedule." "Yes, Ms. Jensdotter." "Have you ever thought about becoming a Legal Sissy, Charlie?" She indicated the the 'Legal Sissy application form' on her monitor. "You'll be able to wear pretty sissy clothes all day long and you'll be told what to do and you'll have all of your needs taken care of. Doesn't that sound wonderful? Just say the word and I can help you get the process started." I stared at the screen. All it would take was a touch of my wrist to the sensor in her desk, and then after the waiting period and the in- person interview at the courthouse... I would be a Legal Sissy. ** Just touch your wrist ** The thought went through my head. ** Just touch your wrist ** Ms. Jensdotter unzipped my pants and pulled out my peenie, sheathed by the sissy panties. She slowly stroked it until I was hard and aching. How was it that I could be milked twice a day and still be so quick to get excited? What was wrong with me? "I want you to know," she whispered in my ear, glancing over at my biometrics on her screen, "that what you're feeling right now is all you. This is who you are, Charlie. You are a Sissy who loves to wear bras and panties. You are a Sissy who loves being in the arms of a strong woman or man and being teased and played with. You are an obedient Sissy who desperately desires to be told what to do." "No..." I moaned, my eyes still riveted on the application form. "Oh, yes, Charlie. It's true. You are a sissy. And deep down you know it's true." "No. I have a wife... " I desperately held on to that one last thought. I am a man. I have a wife. "You can still be with Cindy even if you become a Legal Sissy, you know that, don't you? I know that Cindy doesn't have a sissy of her own. Wouldn't you like to be Cindy's sissy? And take care of all of her intimate needs?" "No..." I tried to squirm free but Ms. Jensdotter held me fast. "That's not what your biometrics are saying," she breathed into my ear. "They are not 100% accurate," I said, unconvincingly. "They aren't admissible in court." "Well, for now," Ms. Jensdotter said cryptically, letting me go. I scurried away to a safe distance, breathing hard and trying to control myself. "Charlie, look into your heart, you know it's just a matter of time. The data doesn't lie." "I... I... I'm sorry, Ms. Jensdotter. But... I can't. I won't. I'm married. I have a wife. I'm... I'm not a..." I almost said 'I'm not a sissy.' "I'm not like that, honestly." "Ha," she snorted. "Enjoy your 3 o'clock milking." * * * Ms. Jensdotter was way off base, I reasoned. But there was something about how close I came to actually touching my wrist to the Legal Sissy form which made my heart race. It was close. Much too close. Damn her! "We have something special for your milking this afternoon!" Missy trilled when I got to my dressing table. "Special?" I asked, worried. Special things at the milking salon were generally not good. For example, the last 'special treat' I got was when they increased the size of my jewel for the third time. Nurse Hamilton reviewed the data from the jewel sensors (apparently the jewel had pressure, temperature, pulse, and other bio-chemical sensors built into it - it was transmitting this all the time as part of my bio data) and decided I was ready for an 'upgrade'. "You should have no trouble with this one," Nurse Hamilton had said, showing me a short, thick silver rod with a pear-shaped bulb at the end." Just seeing it caused me to sweat. "Don't worry, you'll love it. The bigger size allows for bigger batteries and more, um, aggressive vibrations." Wonderful. But she was correct, or rather the data was correct. She lubricated it and inserted it and although it was terribly uncomfortable (I felt like a turkey stuffed for Thanksgiving), it was tolerable and not painful. Of course the larger bulk was uncomfortable, giving my bottom a "Sissy Wiggle" as I walked. "You're looking a little bow legged there," Cindy giggled, when I got home that evening. "Unh--" it throbbed inside m "-- uh... I have a..." I blushed. "A what?" Cindy pressed. "A new... um... jewel," I looked away, embarrassed. "Really??" she asked, eyes wide. Of course she had seen my jewel before, it glimmered and glowed when we were in the bathroom together. She loved to push a finger between my bottom and wriggle it back and forth when I least expected it, making me squeal to her wicked delight. I had to take off my work uniform and pull down my panties while Cindy inspected my bottom. "Oh my *GOD*," she exclaimed, pulling it out half way before releasing and watching my bottom pull it back in. "It's HUGE. I don't know how you could stand such a massive pole up your butt!" "I... uh..." I pulled up my panties and pants. "It's not so bad," I said, flushed with shame. "Well, I know that *I* could never handle that monster in my bottom!" * * * And so, when Missy said "Special" that afternoon, the vibrator throbbed this massive deep throb, sending pulses through my entire body and making me so weak that I had to hold on to the dressing table for fear of falling to my knees before her. "What's special?" I asked, shaking a little. "You're going to have a nap! Ms. Jensdotter said that your work has been so stellar recently, that you're allowed to take 'sissy naps' now." Missy's smile was a mile wide. "S-s-sissy naps?" "Yes! It's one of the absolutely best parts about being a sissy. Mandated naps every afternoon. Surely you knew about Sissy Naps?" My jewel throbbed some more. "N-No," I stammered. "Somehow, I hadn't heard about Sissy Naps." "Well then it's no wonder you've not yet applied for Legal Sissyhood! Once you get used to Sissy Naps, well, there's just no going back. Now, let's get you dressed." In my locker was a Sissyfied onesie romper, made of super soft nylon fabric. "Panties off," she instructed. Of course, Missy had seen me dozens of times now in just my sissy panties, but something about having to be completely naked (except for stockings and garters) felt especially shameful. The jewel throbbed some more and my hard little peenie thrust out for attention, bobbing back and forth in the warmth of the changing room (the changing room was always kept nice and warm, better for naked sissies to change in). Missy held open the romper and I stepped into it. As she drew it up my body, the soft, silky nylon satin slipped over and around my naked peenie. The romper had no legs, just leg holes trimmed in lace and ribbons and scrunched up with elastic - like a baby's romper. I slipped my arms into the short sleeves, also trimmed in lace and ribbons and elastic, feeling them grip snugly (not too tight, just right) around my arms. Missy zipped me up in back. The bodice of the romper was a sailor-style collar, also trimmed with ribbons with eyelet lace, which looked almost like a small bib draped over my shoulders. I looked ridiculous, like an adult baby. My smooth hairless legs made the effect even more pronounced. Was this why had always insisted that I shave and use depilatory everywhere? "Now for your mittens," Missy said, holding two pink puffs of padded fabric adorned with ribbons. "You're gonna love these!" I put my hands in each of the mittens and was surprised to realize that there were individual tubes for each of my fingers and thumb, like a glove with a mitten sewn around it. They were made of soft, lightweight, breathable padded quilting. "Now we tighten these..." As Missy worked, I felt a ribbon inside tighten around the base of each finger and the base of my thumb, gently gripping each digit in a snug embrace. A second ribbon tightened around my wrist. 'There's no way these are coming off,' I realized. Next she had me hold my hand in a fist (thumb on top) and then slipped on a second small bag around each hand, carefully tightening it around my wrist so it would be inescapable. The bag stretched tight over my mitten-padded fists, Once both hands were done I stared at them, realizing how my hands were now completely useless. Just like a baby. "Now the booties." Instead of my marabou mules, or the pumps with the kitten heels, or the pink sparkly sandals, or the white Mary Janes with the buckle on top, Missy slipped satin baby booties onto my feet, tying the ribbons snug around my ankles. They were "pink pink" with pink ribbons and pink lace. "Such a pretty baby girl," Missy said, almost motherly, before reaching back into the locker again, this time pulling out an adult- sized baby bonnet which she put on my head and tied around my neck. It was shaped a little like an old prairie bonnet and it covered my head with had a wide ring of fabric sewn on front, framing my face. Once it was on and tied underneath my chin, with another piece buttoned around my neck, it was like looking through a cone out into the world. My entire view was framed in pink lace - like the entire world had been put into a Sissy picture frame. Was this to be my life? Looking at the world from a Sissy's perspective? Everywhere I look I see pink and white and lace and ribbons in all directions? After hugging me, stroking my peenie and tweaking my nipples through the silky, shiny pink bodice, Missy attached a ribbon leash to my collar and led me out to the waiting room. Opening a gate, she led me into a play area full of stuffed animals, soft pink pillows and brightly colored toys. She hung my leash from a hook. The length was extra long, so that I could sit and move about the play area without feeling anything more than the slightest tug on the leash. She next tied a ribbon around one wrist, then through a loop sewn into the the back of my romper, and then back to my other wrist. This limited the movement of my arms so that I wouldn't be able to reach up and unhook myself. "I almost forgot! My sissy baby needs a binky!" She pulled out a pink baby pacifier and plunked it into my mouth. It was attached to another ribbon which she tied around my neck so that I wouldn't lose it. But the ribbon was so tight that I was forced to suck on it until someone untied me. "Now wait here for Ms. Hardcastle," she said, tickling me in the ribs and eliciting some baby-like giggles before leaving the play area and locking the gate behind her. I looked around the waiting area at the other sissies who all studiously avoided my gaze. The play area had always been a part of the waiting room, but this was the first time I had ever seen it used. Was I the first? Was I always destined to be leading the way for future sissies in the building? I reached out to a large stuffed bunny rabbit and hugged it close to my chest, nuzzling it, feeling close to tears. Every week they found new ways to push me deeper and deeper into sissihood. 'Maybe it would be easier if I just gave in and became a Legal Sissy,' the thought ran through my head. Something about the idea of just giving in felt like it would be such a relief from this constant, humiliating descent and ongoing fight to maintain some link to my manhood. I tried stacking some blocks. It was challenging with the mittens and my restricted range of movement. I had to use both hands and carefully stack blocks one at a time. I sucked on my binky, trying to prevent drool from dripping down my chin. 'Just like a baby,' I realized. "Look, a playmate!" Missy announced, opening the gate and leading in a second sissy. This one was dressed just like me, but in lemon yellow instead of pink. She had the same romper, the same booties and the same mittens. It wasn't until Missy had finished fussing with her, attaching the leash, the ribbons to the wrists and giving her a binky before I dared to look her in the eyes. It was Jamie! Both of us gasped in recognition. Even inside that bonnet and sucking on the binky, it was clear who it was. I blushed a deep, rosy red in shame. Oh Jamie, I thought to myself. What has happened to us? "Are our two babies ready for their nappy-nap?" Ms. Hardcastle appeared, opening the gate and fetching our leashes. "Oh Charlie, you can take your bunny with you. Jamie? Would you like a bunny of your own? Here you go." She plucked a second bunny from the pile and handed it to Jamie who grasped it with his mittened hands. Ms. Hardcastle led us out of the waiting room, past all of the prying eyes of the other sissies waiting their turn, and down the hall to a new door. It turned out to be a nursery, done up with pink duckling wall paper, pink shaggy carpet, a changing table, and a large adult- sized crib in the center with a mobile containing various baby animals hanging above it. Ms. Hardcastle lowered the gate on the crib and had us both crawl up and inside. "Now, let's just make sure you're both nice and comfy for your nappy- nap," she said, with exaggerated baby talk. First she removed and untied our binkies and placed them on the dressing table. Next she untied the ribbons holding our wrists together, first re-tying mine so it went around Jamie, running through a loop sewn into he back of his romper. Then she did the same with Jamie. Ms. Hardcastle took up the slack in both ribbons, pulling our two bodies together, each one of us forced to hug the other, our arms tied around each other and no way to escape. As we squirmed in this close embrace, she continued to take up the slack until our bodies were pressed close against each other and unable to separate. "There," she said, satisfied. "Now, just one more adjustment." Taking a cord, she threaded it through eyelets spaced along the wide rim of each of our bonnets, going back and forth between Jamie and me. When she was done, she tightened up the cords, drawing our heads together until our noses were just barely touching. "So lovely," Ms. Hardcastle sighed. "Two sissies in a sissy embrace, taking their nap." Ms. Hardcastle closed the gate, trapping us, placed our two bunnies with us and then covered the entire crib with a soft blanket. She then dimmed the lights and closed the door, leaving us alone in the room. "Jamie?" I asked. "Charlie!" Jamie responded. "I had no idea it would be you. I didn't ask for this. You must believe me." "Of course not, why would I believe that?" "I don't know..." Jamie shifted on the soft mattress. I felt his soft body in the silk romper rub against me. "Isn't this crazy?" I asked. "I know," Jamie said. We paused like that, both of us shifting and trying to get comfortable. "I'm glad it's you," Jamie said, quietly. "Me too." Jamie shifted some more. Was that... did I feel his? I felt my peenie getting hard. Could he feel it too? "Do you... could I..." Jamie paused. "Could you what?" "Is it okay if we hug? I feel like I need it," Jamie said. "We're kind-of being forced to hug, aren't we?" "Yeah. But..." Jamie paused. "But that's not a real hug. You know what I mean." I did. "Sure," I said, finally. "Thank you," Jamie sighed, pulling me into a hug. In the close-space of our tied-together bonnets, he couldn't put his head on my shoulder, so instead our faces ended up side-by-side, cheeks pressed against each other, as Jamie hugged me and I hugged back. "Oh! I'm sorry," I said. "About what?" "Our... my..." I blushed and looked away. "My peenie," I said finally. I was embarrassingly hard. "Oh Charlie, it's okay," Jamie said. "Can't you feel mine?" He pressed his hips forward. Our peenies touched and rubbed against each other. Jamie's was hard too. "Yes," I breathed. "It's only natural. I'm so hard. I need my milking." "Me too." We lay like that for a while, our peenies rubbing together. "Sometimes I think..." "Think what?" "Oh Charlie. Sometimes I think I really *am* a sissy. I mean... deep down inside." "Jamie!" "I know! I shouldn't. But look at us! Here we are, dressed in sissy baby clothes, in a crib..." Rubbing against each other... "Charlie..." Jamie kissed me on the cheek. "Jamie?" I could tell from the tone of his voice that something was up. "I... I think I'm going to apply to become a Legal Sissy tomorrow." "But Jamie! You can't! What am I going to do without you to help me through this?" "You could apply with me!" I closed my eyes. For the second time today I felt the tug of temptation. "No," I said, finally. "I can't." Jamie kissed me on the cheek again, closer... "Why not?" he asked. "I have a wife, Jamie. I am her husband. I... I just can't." "But you'll still have her. My wife says she'll take me on as her owner and guardian. In some ways, I think I'll be even closer to her than before. She was always so... so standoffish. She treated me like the enemy, in some way. Do you know what I mean? Like marriage was a competition that I had never signed up for. And you know what? I don't want to compete anymore. I don't want to fight or debate or negotiate or try and convince her that I don't have some ulterior motive when all I really want is to be nice and treat her nice, like she deserves to be treated..." "Oh, Jamie," I said pulling him into a hug, feeling his cheek wet from tears. "So... join me Charlie..." Jamie placed his lips on mine... his lips were so soft and moist... I could smell his sissy makeup and sissy perfume... Oh god, I was hard. "Join me," Jamie breathed, pulling me into a kiss and opening his lips. "Oh... Jamie..." I tasted his lipstick as our tongues sought each other out. We squirmed and hugged and kissed like that... lost in each other's arms, safe from the world in this baby cocoon, feeling out urgency overtake us as our peenies slid and thrust against each other -- our jewels merrily humming and throbbing in our baby bottoms -- until we both soiled our rompers with our sissy cream. And then it started all over again. * * * "It looks like our two baby sissies will need to be put into diapers next time," grinned Ms. Hardcastle as we stepped out of the crib, our wet crotches cooling in the open air. "We're sorry, Ms. Hardcastle," I said, my face red with shame. "That's okay, sweetie," she said kissing me on the forehead and hugging me to her bosom. "It's expected from our sissies. This is what we have maids for," she added, turning to Missy Chambermaid who was already stripping the crib and putting the soiled sheets into the hamper. "Now, did you two sissies have a nice nap?" Jamie and I looked at each other. We hadn't napped at all. Instead it was a full hour of hugging and humping and kissing and spurting. For the first time... probably in my life... I felt completely sated. "It was *wonderful*, Ms. Hardcastle," said Jamie. "In fact..." Jamie looked at me and then back at Ms. Hardcastle." "Yes, Jamie?" "I'm ready," Jamie said simply. "Oh Jamie!!" Missy squealed, dropping the linens on the floor. "How wonderful!!" "It *is* wonderful," said Ms. Hardcastle, pulling Jamie into a hug, pressing his face against her ample chest in its starch white, pleated Victorian blouse. "It's wonderful to see one of our own graduate. I wish you all the best as a Legal Sissy, Jamie." "Thank you, Ms. Hardcastle." "Now go with Missy who will take you to my office. I'll be there in a moment to finalize your application." "Join me, Charlie," Jamie whispered in to my ear as we hugged goodbye. "Please..." I shook my head. "Please..." Jamie pleaded, pressing his lips into mine, his sissy tongue slipping into my mouth making me moan. "Please..." he said again. I turned my face away. "I'm sorry, Jamie." "Come, Jamie," Missy said, leading him out of the room. "And you sure, Charlie?" Ms. Hardcastle said, placing an arm around my shoulders. "Y-yes, Ms. Hardcastle," I said, my voice wavering. "Well, it just goes to show. There are always outliers." "Ms. Hardcastle?" "The ML had predicted you'd turn first, not Jamie. I was so sure they were right that I put you first in the office pool, but you surprised us all you devious little minx! Well, no matter, we'll get a nice bonus for Jamie. And we'll get another one when you turn too." I shifted nervously as Ms. Hardcastle placed a finger under my chin and made me look up into her eyes. "Because we both know it's only a matter of time," she said, kissing me on the lips. * * * For the next few days I looked for Jamie in the office, but he was nowhere to be found. The lead data analyst on the floor (who was now wearing a sissy bra like I was, I could see it underneath his blouse) told me that Jamie was on an unpaid leave of absence. "But for how long?" I asked. "I don't know." I looked around the office, trying to figure out what to do. Should I call Jamie at home? It took me a second to realize that the analyst had asked me a question. "What was that?" I asked. "I wondered about your makeup." "What about it?" He hesitated. "Did they make you wear it? Or did you choose to wear it?" I blushed, feeling awkward. I had forgotten it was on, but of course everyone else could see it and was wondering about it. Suddenly I wanted to fetch my compact and look to see if it needed to be fixed up. "It's complicated," I said finally. * * * Chapter 16: Just two days left The end of my punishment period was just two days away. Finally, I would return to being Charles, husband of Cindy, and hopefully put this whole sissy business behind me. No more milking sessions. No more wearing sissy panties or sissy bras. No more keeping my skin all smooth with depilatory soap and moisturizing creams. No more stockings and garters. I reached into my purse for my compact, inspecting my makeup and making a small adjustment. I applied some extra mascara to make my lashes look bigger. The jewel in my bottom hummed as I performed this task (it had been increased in size again, "You're almost at Maximum!" exclaimed Nurse Hamilton). Both the makeup and the accompanying hum from the jewel had become automatic. Expected. Routine. But it still made me horny. In two days all this would be set aside and I would return to normal. Just today and tomorrow and then I was free. Finger's crossed. * * * It had been a long, long day. The morning milking was a full party dress and in the afternoon milking I kept making mistakes with my cock sucking, and so I had to do it over five times until it was perfect. "Sometimes I think you're making mistakes on purpose," Nurse Hamilton observed. "Because you like it so much." "I am not!" I protested. "I swear, Nurse Hamilton!" And I got caned by Ms. Jensdotter. It was the first time in a week, but she caned me not just once, but twice for very small infractions (one of my descriptions had an extra space, I had left the original English spelling of the field name and hadn't corrected it to American spelling). And she had been especially persistent about my makeup, making me fix it up at least three times an hour. "It's too bad that you're not in skirts," she lamented. "Then we could all see your seamed stockings and you'd forever be bending over to make sure they were always nice and straight. Wouldn't that be nice, Charlie? Doesn't that make you want to become a Legal Sissy?" I didn't answer. My jewel thrummed. "Ah well. Soon enough, I'm sure." On the way home a group of boys sat in my section. One of them placed his arm around my waist and played with my nipples while another put a hand on my bottom. At first I shrank away in fear, but he held me tight and soon I relaxed and let it happen. What else could I do? It was a public place, so I knew they'd have to behave themselves. They seemed nice enough, joking and talking about school. But then, as their groping continued, my peenie started to get hard! One of them reached out and grasped it. "Four minutes, thirty seconds," he said, consulting his heads-up. "You'll never be a man if you can't make a Sissy hard faster than that," the friends teased the boy who was playing with my nipples. "This one's too nervous," he replied. "It's not a good test." "See if you can make her spurt!" I was panting with desire when they finally reached their stop. But thank god, at least I hadn't spurted. The seats around me filled up as I tried to get my emotions under control. It had been close, very close. I looked up to see an older gentleman approaching my seat. "Get up," he said. "I want your seat. All the others are taken." I stood up and reached for the hand hold, but he pulled me into his lap where I felt his hard cock press into my bottom. "How's my little girl?" He asked, one hand around my waist while the other stroked my legs. "Tell me about your day." I squirmed. It would be a long ride home. * * * "Hi Charlie! My name's 'Helpful Hailey'!" I screamed. "Sorry!" she said, quickly. "I didn't meant to scare you! Your wife Cindy hired me to help you prepare for tonight!" I had just opened the front door to my home when Helpful Hailey had called out to me." "You are so lucky to have her for a wife," she continued. "When I was a Sissy In Training, all I had was virtual assistants and a shock collar. You're so lucky your wife is so thoughtful to hire me for you!" I stood in the foyer of my home not knowing what to do. It felt like my safe space had been invaded. Here I was expecting to come home and have some quiet 'me' time while I prepared a nice relaxing dinner for Cindy. But now there was a sissy in my house. Hailey was wearing a short flared skirt in pastel green with a cream colored blouse. Underneath the skirt she wore ruffled petticoats with stockings and high heels. Her makeup was done simply and her long hair was pulled into a ponytail with a matching light green bow. "Here, let me help you with those," she said, taking the groceries from me. I followed her to the kitchen where she unpacked the meal. "I think we should get this started as much as we can before we get you dressed for dinner." "Oh. Okay," I said, still struggling with what to do. Should I order her to leave the house? Should I call the police? But she had said that Cindy had hired her. We washed our hands and cooked dinner together and I began to relax. It was nice to have help. I'd heard from other husbands that their wives would actually help with dinner just because they loved to cook. But that was not the case with Cindy. I was always cooking dinner alone. Hailey was a bubbly fountain of chatter. "I so love chicken cordon bleu," she gushed. "And this service is excellent. Very high quality from what I hear. Of course, me and my roommates don't get this kind of food. You house sissies don't know how lucky you are." "D-did you say, shock collar?" I asked, hesitantly, referring to our earlier conversation. "You said that when you were learning to be a sissy, all you had was virtual assistants and a shock collar?" "Oh yes, of course!" Hailey said. "All sissy collars can deliver an obedience shock. Yours too." I reached up and fingered my collar, hearing this. Missy Chambermaid had made me leave it on after my 3pm milking. "Really?" "Yes. It's not as bad as it sounds. It's like a sharp sting to the back of the neck. Just enough to let you know that you've disappointed your owner. But don't worry, Charlie, you won't get any shocks from me!" Hailey rushed to assure me, seeing my worried face. "I'm just here to make sure that you're buffed and polished as a pretty little sissy for your wife and her guest." "Her guest?? She didn't tell me about a guest. Are you sure?" Helpful Hailey shrugged. "Cindy told me herself," she replied, "when I received her instructions." I frowned. "Charlie, please don't worry." Hailey wrapped her arms around me for a hug and a kiss. "We Sissies look out for each other," she whispered into my ear. "I'll make this as painless as I can." While I finished the sauce and the vegetables, Cindy set the table, adding candles and a small table display of ferns and flowers she had brought with her. "It's always good to dress up the table to show a little extra initiative!" She said, in a teacherly voice. She reached out and held my hand. "Now repeat what I just said, Charlie." "Okay," I stammered. "Uh, it's always good to dress up the table to show a little extra initiative." "That's my good girl," Hailey said, jumping and clapping in delight. "It makes your owner... your wife... feel so special and appreciated. Now Cindy told me she'd be home at 7:30. That's about an hour away. We'll put the dinner in the oven on a timer so it will be ready when she gets home. That should give us just enough time to get you ready." "But... my bedroom is that way," I pointed as Hailey led me down the hall. "Cindy said I should set everything up in the guest bedroom," Hailey explained. "I think she wants to turn it into your own Sissy room." "M-my sissy room?" I asked as we entered the guest room. I didn't like the sound of that. "Yes. Now let's both strip." "What? Both of us?" I was dumbfounded as Hailey started unbuttoning her blouse and taking off her shoes and stockings. "Of course, sissy! I need to help get you all showered and petty and soft and smelling sweet for your wife tonight. Do you need my help to undress?" Before I could protest, Hailey was unbuttoning my blouse and undoing my belt and pants. "Oh, *cute* sissy panties!" she said, admiringly. "Oh, how I wish I had such a cute pair!" Soon the floor was a mass of discarded clothing and Hailey was pulling me by the wrist to bathroom where the shower was already running. The warm water cascaded over our bodies as we stepped into the stall. Feeling something brush against my leg, I looked down and saw Hailey's stiff peenie bobbing. She reached for a bar of soap and a wash cloth and pulled our bodies together. "Is this your first sissy shower?" she asked. Her body was warm and wet and slippery against mine as she soaped me up. "Y-Yes," I said. "I'm so honored to be your first. And it looks like someone is enjoying the experience!" Hailey said, boldly reaching down and grasping my hard and aching little member with her soapy fingers. I groaned, putting a hand against the wall for support. "Sissies have more fun in the shower than men or women," she said, scrubbing of my body and then returning to my crotch which she soaped up. "You never know where probing slippery fingers will end up!" "Oh Hailey!!!" I cried out as she turned me to face away from her and removed the jewel from my bottom. "Just making sure you're clean inside and out," Hailey grinned, thrusting first one the two then *three* fingers deep into my anus and wriggling them, making me gasp and yip, my hand on the shower wall for support. "It's too bad that you're not allowed to cream. Spurties in the shower are the *best*. Now *that's* my obedient sissy," she said as I sank to my knees on the tub floor, too weak to stay standing. "Maybe next time I'll be allowed to penetrate you," Hailey said as her finger continued to work in and out of my bottom massaging me from the inside. My arms gave out and I found my face pressed against the tub floor, panting with desire, my bottom pointing up with my ass cheeks spread, unable to resist Hailey's assault, my peenie hard and throbbing. "Enough play!" Hailey said, giving everything one last swipe with the soap before rinsing us off and turning off the shower. "Up and at em!" She gave my bottom a few stinging wet spanks. Next Hailey watched as I shaved and depilated, both legs and underarms, making helpful comments on how to improve my technique. I was then rinsed a second time and then we stepped out of the shower into soft, fluffy towels. Once we were both nice and dry, Hailey reached into a box and extracted two soft, squishy mounds. "Sissy breasts!" she said, grinning. "These are going to be such delightful torture!" "No!" I gasped, crossing my arms over my chest. "I won't!" I looked at them in horror. They were two enormously large breast forms, Double-D at least. Breasts. I would have breasts. There would be no way that Cindy... or anyone for that matter... could ever see me as a man ever again. This was the last straw. The was no way that I was going to be forced to use breast forms, no matter who or what was-- "Ow, ow, ow!!!" I cried. Hailey grasped one of my wrists and twisted it so hard I was forced to my knees. God, she was strong! "I was hoping it wouldn't come to this, Charlie, but we just don't have time." Hailey pulled my arms behind my back and fastened them together with a strap. Grasping my sissy collar, she roughly pulled my head back and then stepped over my shoulders wrapping her legs around my head and holding me fast. I was now kneeling and bent backwards with my head pressed directly into her crotch, her legs wrapped around my neck and her peenie (now hard and dripping) pressed right into my face. "It just takes a second to prepare," she said, taking each breast form from the bathroom countertop and smearing a fixative over the inner surface. Turned on a heat gun and warmed it up (where had that come from?). "Okay, ready to get some nice Sissy Boobies?" Hailey grasped my hair and then stepped off me, turned around and now stepped back into place. Now my face was pressed into her hard little bottom which squeezed and tensed around my nose and lips, grasping at my face with her buns. I struggled and squirmed as I felt her spray something tingly on my chest. "Now hold still," she giggled, tightening her legs so I could barely breathe. I felt her her place first one then the other breast form on my chest, holding them in place and then, once the glue had set, smoothing them out, pressing the edges into my skin. "Now we'll just give this a minute or two, I'm sure you won't mind..." she said, wickedly grasping my hair and pulling me even deeper into her soft ass cheeks. The intimate contact and the lack of air were making me swoon. When I was finally released, I collapsed to the floor causing my new beasts to bounce painfully. "Sorry I had to be so rude," Hailey apologized, helping me to my feet. "But there just wasn't enough time for a softer approach." I looked into the mirror at my new breasts, astonished. The color and texture of the forms had changed to mimic exactly my own skin. The match was so perfect that you couldn't even see the line where the breast ended and my skin started. I reached up to feel them. They were soft and felt exactly like skin. I gasped. I could feel them! "It's the latest sensoskin technology," Hailey explained. "But that's not the best part. Feel this!" she grasped a breast and pinched the nipple. "Ow, Hey!" I felt the pinch! "Oh my god!" I put my hands over my breasts, instinctively protecting them. "But there's more," Hailey grinned. "I want you to say, 'I like my sissy titties.' " "What?" "You heard me!" Hailey smacked my bare bottom with the palm of her hand. "Say it!" "I-I like... my sissy titties." As I completed the sentence, little mouths inside the forms started ardently sucking at my nipples. I couldn't help but to moan out loud. "Sweet, isn't it?" Hailey squealed with delight. "Every time you say that phrase, you'll get your nipple pleasure. And the more... um... enthusiastic you are, the more enthusiastic your bobbies will be!" My god. I have breasts. I have breasts! I felt a sinking feeling as if sliding down a slippery slope and being unable to do anything about it. Hailey sat me down at the dressing room table and I stared at my new breasts in the mirror as they bobbed and swayed. Hailey quickly and expertly did up my hair using a curling iron to give me feminine curls that dangled down my face. Turning me to the side, she did my makeup, slapping my hands away if I tried to help or push her away. Makeup complete (full sissy style), she re-inserted the jewel into my bottom (god, it was so big! It thumped and thrummed being back in its warm spot) and walked me back to the bedroom where we both got dressed in panties and bras. I wore my original sissy panties but now Hailey had a new bra for me. It was a pink lacy push up which held my breasts up high and together, giving me enormous cleavage. The straps tugged at my shoulders holding up the weight of the forms and the band hugged my chest tightly, intimately. "Sissy maid cleavage," Hailey giggled. "Which is just what we want because..." With a flourish, Hailey pulled a sissy maid's costume from the closet. It was shiny pink with white lace trim and layers and layers of flouncy tulle and satin nylon petticoats. "No!" I shouted. "I am not wearing a sissy maid costume! I am not a sissy! I am not a sissy!" "Methinks the lady dost protest too much," Hailey laughed. "Now hurry, step into the skirts, we don't have much time." "No... no... I won't," I whined, backing away into the corner, finally resolved to stop the madness. Everything was happening too fast, too quickly. This morning I was an ordinary man (yes, wearing slippery nylon sissy bra and panties with lace ruffles, garters and stockings with pink satin bows, and makeup... but still a man!) but now I was wearing makeup with curly sissy hair brushing against my cheek, wearing breast forms bonded to my chest (when will they come off??!! Can they come off?) with a lacy push up bra, and about to be dressed in a sissy maid's costume. Enough was enough! Hailey held up the mass of pink frothy fabric and approached me with it. "You know what they call this costume, don't you?" she asked, grinning wickedly. Hailey unzipped the back of the dress and opened it up so I could see the label. 'The Sissy Maker' it said. "No,..." I moaned, pressing my body further back into the corner of the guest room. "Oh, but yes," Hailey said, holding the dress open for me to step into it. "Once you feel how delicious this is wrapped around your body, you'll want to become a full time Legal Sissy for sure." "Stop! I won't!" I closed my eyes and hugged my arms to my body. "This can't be what Cindy wants for me. I'm not her maid, I'm her husband! Yes, I'm going through some punishment, but tomorrow is my last day and then it will all be over! OW!" The collar had shocked me! I reached for the back of my neck where I felt a sting. "Charlie, this *is* what Cindy wants for you. She picked out the maid's dress herself. She's having company and she wants you to serve them at table. This is all arranged. I have video proof if you need it." "It can be faked..." "You know that's not true. Now are you going to step into this dress, or am I going to have to take sterner measures?" "No..." I blubbered, turning away, "please no!" "I was afraid it would come to this," Hailey sighed. She tossed the dress over the chaise (the guest room has a chaise?) and grasped me by the ear and dragged me over to the dresser where she pulled me down to my knees and fetched a long pink cane with a black handle. Without preamble she pushed down my panties, expertly blocked my hands blindly reaching behind my back and applied hard swift strokes of the cane to my bottom, each slice raising an angry red welt. It was a beating - pure and simple. And worse, I was being beaten by another sissy. I was on my knees before her as her right arm rose up over and over again, laying burning stripes on my soft bottom, the shock and pain making me sob and scream in pain. Finally it was over and Helpful Hailey pushed me to the ground, breathing hard. "Have we learned our lesson?" she asked, with that far away look which signaled that she was consulting her heads-up displays. "Yes," I wailed, my face pressed against the carpet. "Please... I'll... I'll be good." I felt empty and broken. All fight was gone - Hailey had beaten it out of me. But worse than the pain, worse than the humiliation of submitting - not to a woman - not to a man - but submitting to a *sissy*, even worse than that was the silence. Where was Cindy? In any ordinary circumstance, being harmed by a third party would fire off all sorts of alarms and alerts for her. She must have been in communication with Hailey as it happened, which meant she could have stopped it at any time. She could have called me to soothe me and tell me that it was all a mistake, that it was all over, that this was not what she wanted. But she didn't. There was only silence. No video, no note, no alerts, not a peep. Cindy, where are you?? * * * Hailey helped me to my feet and quickly fixed my makeup. "It's a good thing this new Christeen line of makeup is waterproof," she smiled. "Christeen really understands what it means to be a Sissy." And now for the dress. As before, she held open the 'Sissy Maker' and looked at me. Resigned to my fate, I carefully stepped into the pink Sissy Maid Uniform and let Hailey draw it up. It was lined on the inside with smooth nylon which slipped up my body. I threaded my arms into the sleeves and was surprised that they were long sleeves with loops at the end which went around my thumbs to keep the sleeves in place. Hailey pulled the bodice closed behind me and I discovered that it contained a built-in corset. "Perfectly sized," she said, with satisfaction. "The measurements from that Sissy Store you frequent were perfect." She slowly did up the hooks in back, each one nipping in my waist a bit more, like a large hand slowly closing its grasp on me. As I stood I realized, for the very first time, what it felt like to truly submit. Obedient, I stood meekly as Helpful Hailey (perhaps I should have asked her who she was helping and for what purpose) finished up the hooks and then closed the leather strap around the neckline, fastening it shut with a lock that closed with a *snick*. I was now locked in. I would be unable to remove the uniform without a key. A Sissy Maid. I am a Sissy Maid... My mind was numb, from the pain, the shock and humiliation, and my wife's apparent indifference. This must have been what she wanted... Hailey added white gloves ("always white for a maid" she explained) then had me don white stockings, attaching them to suspenders that hung down from the bodice of the dress, and then added a pair of pink high heel pumps. "I know, not very practical," she apologized. "But they were specifically requested." They had buckles across the top which she closed and then locked shut. The brass locks clinked as I walked. "A bit too fetish-y for me," she shrugged, "but the customer is always right, isn't that correct, Sissy Maid Charlie?" "The... the customer?" "Yes, the customer. Sissy Maids always put the customer first. Whatever the customer wants, no matter how intimate or degrading, you will do it. 'If it is possible to do, then thy will be done.' That's your motto now." "My motto?" I was having a hard time understanding what Helpful Hailey was saying. "Yes, dear, your motto." "Why...?" "Because you're a Sissy Maid now, Charlie." "I'm a... a... Sissy Maid?" "At least for tonight. Oh! I almost forgot! Your name badge." Hailey plucked a plastic engraved name tag from the dresser. It was white with a pink border and pink lettering which said: "Sissy Maid Charlie - It is my pleasure to serve you!" "It is your pleasure to serve," Hailey chuckled. "I bet it is!" "But I... I mean... I can't... I'm not..." "You house sissies think you're all so superior," said Hailey, "looking down on us working sissies." "No! I would never do that! But I'm not... I mean--" "Or are you holding onto that slim hope that you are actually a man? Oh Charlie, I don't know how to break it to you, but you're wearing stockings, panties, a bra, a Sissy Maid Uniform with brand new Sissy Titties. And you know what?" "W-what?" I stammered. "You've been hard this whole time. Even during the caning." My face flushed with shame. It was true. "But I'm not... I mean... I'm married... Cindy wouldn't..." "Listen carefully," Hailey hooked a finger into my collar and pulled me close. "Your wife Ms. Pauline will be here soon. We have a lot of work to do before they get here and you will be very busy after they arrive. I need you to be submissive, humble and eager to please. Do you understand?" "Yes, Hailey," I said, looking at the ground, ashamed. "Promise me." I gulped. "Promise!" She said, more firmly, twisting my collar. "I promise to be submissive, humble and eager to please." "Again, this time like you mean it." "I promise to be submissive, humble and eager to please, Helpful Hailey," I said a second time, this time trying to make it sound honest and heartfelt. "That'll do. Now promise me you'll follow all instructions, immediately and without question." "I promise." I paused, then sensing that Hailey wanted more, I tried again. "I promise that I will follow all instructions, immediately and without question." "Good girl. Nipple reward!" "OH!!" I gasped. My hands jumped up to my breasts, as the forms briefly sucked and nibbled on my nipples synchronized with throbs from the jewel in my bottom. "See? It won't be all bad," Hailey chuckled. "Not for a true sissy like you." * * * We quickly up the final preparations for dinner and I received instructions from Hailey for curtsies (head bowed, skirts held between thumb and forefinger, pinkies up, one foot in front of the other, then bend knees -- "good enough" she said, shrugging, "they know you're new to this") waiting at table ("always serve from the right") and other etiquette tips ("always have a pleasant an interested expression", "always be alert to commands", "stand still and stare ahead"). I checked and fixed up my makeup one last time. "And you are to refer to your wife as 'Ms. Pauline' or 'Ma'am' and her guest as 'Sir'. Do you understand?" "Yes Miss Hailey." "Oh, Sissies never get honorifics," Helpful Hailey laughed. "But I applaud your enthusiasm! Now stand here by the door until they arrive. And good luck!" * * * Chapter 17: Cindy and Her Guest I stood uncomfortably on my high heels waiting for Cindy and her guest to arrive home. The heels stretched my calves and pinched my toes. I could feel the garters pulling at my stockings. The corset around my waist was tight and constricting. My new breasts were heavy on my chest, the straps pulling at my shoulders. But all I could think about was one thing: Her guest is a man! And here, all along, I had assumed her guest would be another woman. But no. My wife was bringing a man home with her and here I am, dressed as a sissy maid and ready to serve them at table. The thought made me queasy. But maybe he would be a sissy too? Or at least somewhat effeminate? Maybe he was one of her paralegals at work or something like that? Or maybe her guest was really a she? There was a new religion where all of the women were referred to as 'Sir'. But that seemed like a long shot. I nervously smoothed out my dress for the 100th time. No matter how often I did it, it always sprang right back up. The skirts were so short that my panties would be exposed every time I took a step. They would flounce about and my stockings and garters would be clearly visible. A short little white tea apron, trimmed in lace, was tied around my waist. It was the only part of the costume made of cotton, a nod, I expect to the fact that I would actually be serving food and doing cleanup. I looked down at my new titties. They were so large! The cleavage which showed at the neckline of the uniform was positively indecent. Slutty. I could feel their weight pulling my forward. I had to pull my shoulders back and stand up straight to compensate. This caused me to thrust my chest out. "I'm a slutty little maid," I grumbled to myself. "Oh... Damn it!" I jumped and squealed as the breasts nipped my nipples and the bottom jewel thrummed. Shit! My peenie in the sissy panty sleeve, which I had just gotten to settle down, was now hard again! It thrust up into the skirts. I ruffled the petticoats as best I could to try and hide it. * * * "I'm home!" Cindy called out, opening the door. A huge smile lit up her face as she saw me standing in the foyer. I curtseyed. Cindy handed me her briefcase and then stepped aside and let in her guest. Shit. "Hey, nice little apartment you got here," he said. Without a glance, he tossed his brown leather jacket to me which, surprised, I caught at the last second before it hit the floor. It smelled well worn and embedded with manly musk. "It's only a starter." I helped Cindy with her coat. "I should be able to move into something larger in a few months, once I've passed the bar and the MPRE." "The bar exam, huh?" He was tall and lanky but with thick, muscular arms. His hair was tousled in a way that looked too purposefully mussed up to be an accident. "Well, they don't actually have bar exams anymore," Cindy explained, showing him into the living room. "My boss says that it's pro forma for a woman with my degree." I hung up the coats in the hall closet and put Cindy's briefcase in her study. "It's all based on big data these days," Cindy was woman-splaining when I returned. "It just takes a few months of office work for the algorithms to gather enough data and then I'll be an official lawyer. Sissy? Go fetch me a glass of wine." I froze. Did she just call me... Sissy? "Sissy?" Cindy said again, looking me straight in the eye. "Uh... yes, uh..." Cindy frowned at me, her eyes narrowing. I knew what I had to do, but the words stuck in my throat. "Yes... Ms. Pauline," I said, finally, adding an awkward little curtsy almost as an afterthought. Cindy's face broke out into a radiant, approving smile. I felt the jewel hum. "Ed?" Ed. His name was Ed. Suddenly I realized that this must be the construction worker from her office. "Oh, a beer, thanks. Anything." I tottered out on my heels, the clack-clack sounding like nails being pounded into the coffin of what little was left of my masculinity. I returned with a silver tray holding a glass of wine for Cindy and a glass and a bottle of beer for Ed. They were sitting together on the couch talking, Cindy with her arms around Ed. "You didn't tell me you had a Sissy," Ed said, watching me pour the beer into the glass and then accepting it from me. "I don't. That's my husband." "Husband?" Ed burst out laughing. "Seriously? That Sissy is your husband?" "Yes, he most certainly is. Isn't that right... Sissy Charlie?" "Yes, Ma'am," I said, feeling my face flush with shame. "Well, I doubt he'll be your husband for much longer, not from what I see" "I know. I never expected him to last this long. But he's not applied yet." "Maybe he just needs a little encouragement?" Uh oh. "What do you mean, encouragement?" Cindy giggled, her eyes lighting up. "You know, encouragement from a real man. Would you like me to show you?" "Oh yes," Cindy said, looking at me. "Put that tray down, Sissy, and come over here." "Y-yes, Sir," I stammered. I placed the tray on the end-table and stood before Ed. "You forgot to curtsy, Sissy," Ed grabbed my arm and roughly pulled me down. With a squeal, I fell into his lap, my legs kicking up into the air. My new breasts bounced painfully as I landed. "They're always forgetting to curtsy," he explained to Cindy, adjusting me in his lap. I could feel his hard penis pressing against my side. My god, it was a monster. "It's so typical Sissy. It's because they secretly want spankings, so they make minor mistakes on purpose." Ed pushed up my skirts and held them in place with one arm, and then pulled down my panties. Cold air washed over my naked bottom. "She's been striped recently," Ed observed, seeing the red markes on my bottom from the pink sissy cane. "Probably the Sissy Helper I hired." Cindy reached over and ran a finger over the red marks from Helpful Hailey's caning from earlier. The light touch of her cool finger gave me goosebumps. "Hey, nice Jewel," Ed said. I could hear the smirk in his voice. "I hear those new sissy trainers are real effective." "Only the best for my Sissy Charlie," Cindy said, stroking my head which was now pressed into the sofa cushions. Curly hair fell over my face, cascading over my cheeks. "I was able to split the cost with his boss at work. And she also gave me a five-year no-interest loan." "The Old-Girl's network," Ed observed, his hand stroking and squeezing my bottom, making me gasp and shiver. "She works?" "Yes, as a data processor." "Figures," Ed snorted. "They're all sissies." "If not, they soon will be," Cindy said, cryptically. Without warning, Ed delivered his first spank. Shit that hurt!! I yelped and reached out to try and ward off his next blow, but he easily captured my wrists and pinned them together to the small of my back, forcing my arms to bend up painfully. Oh god, he was strong. It was clear he worked with his hands for a living. Ed gave me a second spank, making me scream before I could stifle it. "Your spanks are so hard," Cindy said with admiration. "Yeah, only a good hard spanking will teach them their place," Ed explained. "Otherwise, they get lazy and uppity and not focused enough on our needs. Isn't that right, Sissy?" Ed gave me two more hard spanks. The caning from earlier, amplified the pain 10-fold. My buns felt like hot coals. I wouldn't be able to sit comfortably for days. "I asked you a question!" Ed barked, spanking me again. "Don't you Sissies need a good hard spanking now and then?" "Yes!" I shouted, bursting into tears, just wanting the whole painful, humiliating experience to be over. "Yes, we do!" "That's right you do," Ed said, with two more spanks, both the hardest I'd ever felt. "There, now you're done. You won't be forgetting to curtsy, now will you, Sissy?" "No!" I blubbered. "I promise!" "Very good. And you'll be a good, obedient Sissy?" "Yes, Sir! I promise to be a good obedient Sissy!" "Oh Ed! That's amazing! You know, until this very minute, I wasn't entirely certain that Charlie would end up as a Legal Sissy, but now I have no doubts. She's sissy to the core." "Do you have any moisturizer?" "Moisturizer?" "Yeah. It's a good idea to moisturize their bottom after a spanking. Sissy spanking cream is best. It helps with the healing so you can spank them harder and more often." Harder and more often?? Hearing the words brought fresh sobs to my lips. "Maybe the helper left some in the Sissy room," Cindy hopped up. "Found it!" she called out a moment later. I shivered as Cindy squirted the cold cream onto my hot bottom and then moaned as Ed used his rough hands to rub it in. His fingers occasionally slipped into the crack of my ass, jostling the jewel, making me squirm. "All done!" Ed gave me one more wet spank and pushed me off his lap. I scrambled to my feet, panties around my knees, desperately trying to pull them up. "Did I say you could pull up your, panties sissy?" "No, Sir!" I immediately let go and hung my head, trying to cover my crotch. "Hands to your side!" "Yes sir!" With my hands to the side, my little peenie, still caught in the panty sleeve, was exposed, pointing straight out, hard and glistening. I felt a blush of embarrassment wash over me. "See, this is how you know they're a real Sissy," Ed said, tweaking my peenie with a flick of his fingers. "Real men would have lost it by now, but she's still nice and hard." He reached out and grasped my peenie, rolling his fingers to squeeze out some precum which he rubbed over my little head with his thumb. "I've noticed," Cindy grinned. "It *never* seems to go down, it didn't use to be that way." It's because you no longer have sex with me! I wanted to cry out, but I held my tongue. "I know, let's play a game!" Ed grinned. "But first, aren't you forgetting something, Sissy?" "F-forgetting something? Sir?" I racked my brains for what I might be forgetting, but none of my training had prepared me for being spanked by my wife's lover. Also it was hard to think, with his fingers still pinching and manipulating the tip of my peenie. "Wow, she really is new! Sissy, you need to curtsy and thank me for your spanking, admit that it was right to be spanked for what you did was wrong, and promise to do better in the future." I looked at this man who was sitting on *my* couch, sitting next to *my* wife, and enjoying *her* hand around *his* waist. The gall of him! This... this.. construction worker, telling me what to do! I flushed with shame. "She blushes very prettily," Cindy observed. "Now, Sissy," Ed's voice had a hint of warning, as if he wouldn't hesitate to spank me a second time. "Th-thank you, S-Sir," I quickly said. "Thank you for - for - for my spanking." I held my maid's uniform skirts out, put one leg in front of the other, bowed my head, and curtseyed. "You were right to spank me because I forgot to curtsy, and I will sincerely try to remember to curtsy in the future." "Very good Sissy. Now that wasn't so hard, was it?" "No sir." For good measure, I curtsied again. "And look, now you're learning to curtsy. Ha! Look, Cindy, she' really leaking now." "Charlie, look," Cindy said, holding Ed's fingers up where I saw a drop of precum squeezed out between them. "Even you must admit that you were born to be a sissy. You do seem to enjoy it." "N-no... ma'am." "Let's play a game," Ed suggested. He continued to pinch and stroke the head of my penis as it stuck out from the lace collar of the sissy panties. "I'm going to take *intimate* advantage of your body," he said, "like what I'm doing right now. Any man who was being fondled by another man would hate this, would be sickened by it. But a sissy will naturally like it." "What's the game?" asked Cindy. "If she can stay still and not moan or involuntarily thrust her hips or show some other sign of pleasure for five minutes, then she wins and she can return to being Charles and can put on her male clothes and we'll enjoy a nice evening together like equals." "Only five minutes?" Cindy gasped. "That's much too short!" "It'll be more than enough time, believe me." I thought about it. His fingers were already torturing my hard little peenie. What more could he do? "And if I lose?" I asked, my voice coming out in an embarrassingly high squeak. "Then you must admit you are a sissy in every way, to your wife and to me, and you must perform all of your intimate sissy chores for the evening, eagerly and without complaint, like a true sissy would." "I'll do it," I agreed. After all, what would I have to lose? I was already wearing a sissy maid's costume standing in front of my wife and her... her... her lover. Why were such thoughts always making my peenie get harder? "Okay, I have the timer ready," Cindy announced. She looked at me and I could tell from here eyes that this was my last chance to prove I was a man to her. I gritted my teeth for whatever Ed would do. "Ready," I said. "Go." Ed reached down and grabbed my sissy sac, rolling my num-nums in his hands, and then at the same time reached around me and placed his massive, strong hand on my bottom. He then pulled me forward, into his lap. His fingers slipped between my buns pressing against the jewel and quickly stroked it back and forth. "Ohhhhmmmm!" I gasped, wriggling my hips from his invading digits. "Oh, Charlie! You've already lost!" Cindy said. "It's only been 5 seconds!" "I told you it wouldn't take long," Ed chuckled. "But let's make sure it's real obvious to this sissy her true place in life." "What are you doing?" I gasped, as Ed pulled me closer. "What? No!" Ed put a hand around my neck and turned my head to face him (my god his hands were strong!), tilted my head and placed a kiss on my lips. "No.... mmmmph!" I squirmed and wriggled trying to get away. But Ed held me close, his lips firm and demanding, breaking down my barriers. "Open up, sissy, you know you want to" he breathed, before returning to the kiss. "Maybe I can help," Cindy said, excited, watching us. "I just got a note from Helpful Hailey. Oh! Nipple reward!" "Unnnhhh!!" I cried out as the breast forms began nibbling and sucking my on defenseless nipples. Ed immediately took advantage and thrust his tongue in my mouth. My willpower battered from all the stimulation, I couldn't help myself. I moaned. I moaned and let it happen. I felt taken and used. "Nipple reward," Cindy said again, the huskiness of her voice betraying her excitement. This time, both the breast forms activated and my jewel throbbed, aided by Ed's fingers which pressed against the jewel, pushing it deep, invading new territory, before relaxing and then letting it slip out a bit before doing it again, And again. And again. "Please.... no... stop..." I moaned, as our kissing continued. "Oh!!!" Ed had grasped my peenie, his thumb and fingers wrapped around my little cockie, pinching and stroking my baby helmet. "Please..." I moaned again, this time, my hips thrusting up all on their own. My peenie was hard and aching for his touch. "Nipple reward," Cindy said again with her evil voice, as my body thrust and jerked with unwanted, forced pleasure. "Please.... why?" I sobbed. I didn't want this to happen! I struggled again, but Ed held me fast, one hand with fingers thrust between my buns, and his other hand grasping and manipulating my peenie. "She's primed," he said, a tone of satisfaction and conquest in his voice. "Do you want to measure how high?" "How high?" Cindy asked, with a giggle. "What do you mean? "Get a ruler and I'll show you. I'll keep her on edge until you're ready." Cindy rushed out of the room. While she was gone, Ed slowed his manipulations on my peenie. "You are a pretty one," he whispered in my ear. "And you're so sensitive. I like that. If Cindy makes me her live-in stud, you and I are going to have lots of fun together." Live in stud?? Cindy returned with the ruler. "Only twelve inches?" Ed chuckled. "Well, we'll see!" Ed leaned me back so I was looking up into his eyes. "Place it here," he indicated. "Nipple reward," Cindy said, holding up the ruler to my peenie which was now sticking straight up in the air. "From three," said Ed. "One. Give in, Sissy. You're going to cream in front of your wife and her lover whether you want to or not. You've already lost the bet, so you might as well enjoy your humiliation." He leaned over, captured my mouth with his and gave me another kiss. "Two. Let yourself go, Sissy, you know you can't help it." His manipulations on my peenie increased. He gave me another kiss, this time with his tongue in my mouth. "Nipple reward," Cindy said. I couldn't help myself. My hips involuntarily thrust upwards, and I moaned into the kiss. "Three. And now..." He then did something strange with his fingers, rubbing directly under the little helmet of my peenie with short, intense strokes. "Spurt." And, unable to do anything about it, I arched my back and squealed, my peenie jerking and pulsing and my sissy cream shooting straight up into the air. "Oh Sissy Charlie!!!" Cindy exclaimed. "It's so high! You spurted higher than the ruler!" "I thought she might," Ed grinned. "She's an excitable one. The ones in denial, they love humiliation, so when you get them to shoot against their will, it's always the best. Isn't it, Sissy?" Ed pulled me into another kiss. I was still squirming and spurting, but not as hard, coming slowly down from the release of my Sissy passions. "Ugh. Do you have a spurties towel?" Ed asked. "I saw a stack of them in the Sissy room," Cindy ran off. Ed continued to manipulate my peenie while she was gone, making sure I was fully milked. "Had you already been milked today?" He asked. "Yes," I admitted. "Twice." "Twice? Impressive." * * * Cindy returned with a stack of terry cloth spurties towels and they both wiped up my cream as best they could. My sissy panties were soaked, of course, and there were splotches all over. On my skirts, on my bodice on Ed, and on the sofa. Ed gently lifted me and placed me on the floor, where I lay for a second, dazed, before getting to my knees. "Stay there," he commanded. I looked up. Ed was standing before me. "You lost the bet," Ed said. "So now you have to pay up." "Admit you're a sissy," added Cindy. "I... I admit that --" "Look your wife in the eyes while you say it," Ed commanded. I lifted my head and looked Cindy in the eyes. Oh god, this was it... She was my wife. She was the one I approached in the library all those years ago when I screwed up the courage to start a conversation. She was the one I asked out to movies. That movie where we spent all of our time necking so that we didn't remember what the movie was about at all later when we were quizzed by her parents. She was my soulmate, my best friend, my protector, my... wife. My Cindy. I pleaded with my eyes not to make me do this, but she looked back without mercy. In her eyes was love, but it was a tough love. The sort of love a parent has for a child who needs to be taught a lesson. It was a look which said: 'we both know what just happened and now you have to do your duty.' Cindy and I looked at each other for several seconds. "Sissy?" Ed asked. "I... I admit that..." I gulped. Cindy's eyes told me I had to continue. That I must continue. Suddenly I keenly felt what I was wearing. The pink sissy maid uniform with the built in corset and the long pink sleeves which looped around my thumbs, the tight neckline, and my white gloves with lace around the edges. The garter straps attached to my stockings and my white heels, locked on. My hair and makeup (now severely in need of repair) were full and completely sissyfied. I could smell my delicate sissy perfume along with my sissy spurties cream which had soaked into the uniform. And my new breasts, heavy and pulling on my chest, showing their deep cleavage, pulling on the straps of the bra, swaying with every motion. It all came together, right at that moment, and there was only one thing I could say. Only one thing which was the truth. "I am a sissy," I said. The look that passed between Cindy and me made it clear that she and I both understood what had just happened. She now knew, fully and without doubt, that I was truly a sissy, and that I knew it too. "So, now, *Sissy*, do we understand each other?" Ed asked. "Yes, Sir," I said, staring at the ground, my face burning. "Excellent. Now for your first sissy duty. I need to be pre-drained before I can fuck your wife." "What? But if Charlie drains you," Cindy complained, "then you'll have nothing left for me!" "Oh don't worry about that," Ed was smug. "I have plenty. This is a Sissy's purpose. It's like, her job #1. She pre-drains the man so he can last longer when he is used for sex by the lady of the manor." "But you never have a problem with endurance when we fuck over lunch." "That's because I'm careful to stop at the Sissy Store for a pre- drain before seeing you." "Ohhhh..." Cindy's face showed a dawning realization. "Well, that explains the stains on your briefs. Well, okay then. Sissy? You heard him. Time for his pre-draining." Pre-draining? I looked from Ed to Cindy. What the hell was that? Surely he couldn't mean that I needed to... I looked over at Ed who glanced down and then thrust his crotch out at me. Oh, fuck. That was *exactly* what he meant. I reached out with my gloved hands, hesitant, and unbuckled his belt, unzipped his jeans (the sound of the zipper gave me shivers) and then slowly, awkwardly, pushed down his pants. Oh fuck, the bulge in his briefs was enormous. Slowly, with my gloved fingers, I reached into the waist band of his briefs and pulled them down, exposing his cock which bobbed out, swinging in the air, getting harder and harder like a steam dial on an old-fashioned boiler. I looked over at Cindy, praying that she would intervene, but it was not to be. She settled down on a chair to watch and spread her legs, a hand in her crotch, slowly pleasuring herself. Looking at Ed's penis, I was flooded with memories of my training with Robert, the robot cocksucking trainer at the milking salon. All of the steps that had been drilled into me by Nurse Hamilton came back to me. Was this what all that training had been leading towards? It must have been. After all, I am a sissy. This is my place in life, on my knees, before a man, helping him to... ... to better fuck my wife. I closed my eyes and shuddered. "Charlie!" Cindy barked out, seeing my hesitation. "Give her a minute," Ed counseled. Oh my god, even with my eyes closed, I could smell him. I could feel the heat of his cock through my gloved fingers. I didn't want to do this! In private, in the milking salon, with only Nurse Hamilton -- that was one thing. But here, with a real man... with Cindy watching. This was something else entirely. This was truly submitting. But what else could I do? What avenue of protest remained open to me? Dressed as a sissy maid, having just been hard-spanked and milked and having lost the bet. There was nothing. There was no way out. I placed my lips on the tip of his penis. Oh my god, the taste... the texture... the warmth... The robot that I practiced on was good. One of the best and most anatomically correct fellatio training robots available. And its penis was soft like skin, senso-skin. But as soon as I put my lips on Edward's hard cock, I understood the difference between man and robot, between the living and the artificial. As I sucked the head of his cock into my mouth (being careful to work the underside with my tongue and keeping my teeth out of the way with my mouth in a perfect 'O' like my training) this living, human, manly rod of flesh, Ed's most private body part, the part which urinates and shoots sperm and fucks women... was in my mouth. 'He pees with this,' the thought ran through my head as I sucked it deeper, my tongue probing the tip before I pulled out (per my training) and sucked it in again, this time a bit deeper. I moaned in pleasure through my nose to make sure he understood that it was my pleasure to be used by him. "That's my sissy," Ed said. "She's really well trained," he said to Cindy, putting a hand on my head and running his fingers through my hair as I bobbed up and down on his penis, getting deeper and more passionate with each motion. "The analytics from the milking salon recommended the advanced classes. They said it would put Charlie into an especially sissy frame of mind. I had no idea it would be such a useful skill in real life." "Oh, Sissies *have* to be the *best* cocksuckers," Ed said, grunting as I pushed his cock to the back of my mouth and give it an especially intense, full-shaft suck. "Cock sucking and pussy licking are practically their whole purpose for existing. And you! You little minx!" Ed pulled my head to his crotch, his hard shaft filling my mouth, the head of his cock pressing at the back of my throat, "claiming you're not a sissy but all the time taking cock sucking classes! Had I known, I would have just slapped you a couple of times and fucked your face! 'I'm not a Sissy.' Ha! Give me a... unh!! A fucking break! No one who's not a sissy is that good at sucking cock!" I pulled his cock out of my mouth, stroking it instead with a gloved hand, leaving me free to lick and suck on his balls. They were hairier than Robert's balls, and apparently more sensitive. I hummed and worked the balls through my tongue and lips, smelling Ed's musky smell, until he was gasping and clenching. But I must have judged Ed's excitement wrong, because he pushed my head away, his balls coming out of my mouth with a wet plop. Grasping my head in his hands, he thrust his hard rod deep into my mouth, the soft skin over my lips and tongue, my hands flailing uselessly in the air, until it bumped against the back of my throat. Oh god. I knew what was coming next. I took a deep breath through my nose. As if I were no more than a pleasuring device, Ed tilt-probed the back of my throat with his cock, until with a nudge, he found the right angle and pushed down my throat. "On my goddess!" Cindy screamed, seeing Ed's cock now thrust all the way in, my neck bulging with his manhood. "Oh, yeah, Sissy! That's what I need!" Ed shouted. I gagged and flailed, trying to get away, but Ed held firm. I had only recently begun deep-throat training, but Ed didn't seem to care. Perhaps my gagging was turning him on, as my throat spammed around his cock head. At one point, Ed pushed all the way in and held it there, my face mashed into his crotch, his pubic hair pressed against my nose. Tears streamed down my face. Unable to breath, I desperately worked to control my gag reflex. Once I was able to settle down, I submissively stroked his hip and he slowly pulled out, giving me a chance to breath. Then he looked at me. "I told you what I need," he said. Understanding, I took a few deep breaths and then sucked his cock down until it reached the back of my throat, then I paused for a second, and then pushed it home, all the way down, my nose pressing into his pubic hair. "That's my obedient sissy," Ed growled, taking over. "Oh god, it so sexy when you can bend them to your will." "Goddess, yes!" Cindy gasped, watching the display. Her hands were fully inside her panties now, frigging herself. Ed was close. His thrusting increased in tempo and fury, small thrusts, my nose and lips mashed against the root of his cock, his hands entwined in my hair, my own hands now resting on the couch. I did my best to look up at him with dewy, wanting eyes and he looked down with an I-own-you-now look. "OH, YEAH!" he shouted. "Check this out!" The first shot went straight into my mouth as he pulled out, coating my tongue and mouth. Then he pulled all the way out and the next two shots of his man cum were right in my face, big sploogy jets hitting me with force and splattering everywhere. The fourth shot came as the tip of his cock nudged into my lips, his sperm covering my lips and tongue and teeth. The final two shots were pressed right into my face as he painted my face using his cock like a paintbrush with his ejaculation as the paint. "Holy crap! OH GODDESS!!" Cindy screamed, as she came as well, her fingers working furiously and a strong smell of her sex in the air. "OH FUCK, I've never seen anything so HOT in my life! HOLY SHIT." "I thought you might like that," Ed said, clearly proud of his performance. He looked down and stroked my cheek. "I'll release my biometrics so they can evaluate your performance and train you for my pleasure profile," he continued. His cock was softening but he still pressed it into my face, the tip still leaking. "That way, next time you can do even better. They'll tune you to be my perfect cocksucking sissy slave." * * * Chapter 18: Serving My Wife and Her Lover in the Bedroom Cindy and Ed retired to the bedroom and I was instructed to bring them dinner in bed. "And don't you dare clean your face," Cindy said. "I want you to serve us just like that." And so I finished cooking dinner and plated it with my face splattered with Ed's sperm. One of the shots had actually gone up my nose a bit. It was a pungent, musky, jasminy, moist, cummy smell. 'I am a real cocksucker now,' was all I could think. 'A sissy cocksucker.' Cindy had changed into sexy lingerie including a rose-pink bra with black trim and a clingy pair of tap panties. It was lingerie I had purchased for her on our one year anniversary and which she had never worn. And now she was wearing it for another man, in our wedding bed. I placed the trays on the bed and stood to the side while they ate, at their beck and call, waiting obediently to refill a wine glass, fetch a condiment or serve dessert. Every now and then a wet blob of Ed's cum would slowly ooze down my face and drip onto the bodice of my shiny pink satin Sissy maid's uniform making a dark splotch. Cindy and Ed fed each other with their fingers and chatted about the day. I watched jealously as Ed had intimate moments with my wife, stroking her nipples in the bra or running a hand across her bottom in the panties I had bought her. Finally dinner was over and I was able to clear the dishes. "Anything else, Ma'am?" I asked, hoping desperately that I would be excused. The last thing I wanted was to watch what came next. Every time she kissed him, every time she laughed at one of his jokes, every time she reached out and touched his member (it really was huge), was like a dagger in my heart - a dagger in the heart of our marriage. I realized just then how much I still loved Cindy. Through it all, I loved her desperately, fully, and completely. My everything. "Take off your panties." "Please, Cindy," I pleaded with her. "I think you should be calling me 'Ms. Pauline'," Cindy corrected me. "Yes, Ms. Pauline, thank you, Ms. Pauline," I agreed, feeling trapped. I reached under the skirts of my maid's uniform and slipped off my panties, folding them neatly and placing them on the chair by the bed. The petticoats stroked over my naked buns and peenie. "And your jewel," Cindy said, obviously reading some instructions from her heads-up. "Take that out as well." 'Why would I need to remove my jewel?' I wondered. With some difficulty, I extracted the silver butt plug (it had just today been upgraded to "maximum" at the milking salon), cleaned it with some wipes and placed it on the dresser. "Very good. Now Charlie, I have something very special for you. It was very expensive, but you, my darling sissy, are worth it." Cindy smiled a predatory smile, making me nervous. "See the pole in the corner?" I looked over, and with shock, noticed a chrome pole sticking up from the floor, with a black rubber seat on top. Where had that come from?? "Oh hey, you got a sissy pole," Ed said. "Cool." "It was installed this morning," Cindy's eyes glittered. "Now Sissy, go over to the pole and see? It has a place for your feet." The pole was about two and a half feet high. The seat on top looked perverted and uncomfortable. Oh god. The 'place for my feet' was two pink-leather ankle cuffs, rigidly fixed to the pole, about five inches off the ground. "Ms. Pauline?" I asked, hesitantly. Surely, I wasn't expected to...? But Cindy just looked at me with arched eyes. Still wearing my white high-heels, I carefully stepped into the cuffs, first one foot and then the other. The leather was soft, well padded, and rich-feeling. The pole was now between my legs, the seat about as high as my knees. *click* "Shit!" I gasped. The cuffs cinched had closed on their own using some hidden mechanism, drawing snug and then ratcheting soft and tight around my ankles. I looked up at Cindy, freaking out. "It's the latest design," she said, grinning like the cat which caught the canary. "I spared no expense." "Th-th-thank you... Ma'am," I stammered, starting to shake. Ed was lying on his back with Cindy at his side, gently running her fingers over his chest. *thunk* I felt the soft vibration of motors running. As I had feared, the seat slowly began to rise (the ankle cuffs didn't move). My heart raced, realizing too late that I should have objected more and fought harder before allowing myself to be trapped like this. I pulled against the ankle cuffs, but it was hopeless. What had I done? I watched in horror as the seat slowly slid up and into my crotch, coming into contact with my naked bottom underneath the skirts of the sissy maid uniform, which were too short to provide any sort of barrier. Down the center of the seat was a rounded, soft rubber fin which slid smoothly up between my cheeks, parting them and exposing my anus to it's creepy, intimate embrace. I squirmed as the rubber squished and molded itself into my bottom, exactly filling in every curve and crevice and forcing my buns apart as it did so. The seat continued pushing up, pressing more and more firmly into my bottom, stopping just before it became painful. "Look at her," Ed said. "Nice and stretched." It wasn't uncomfortable, just horribly embarrassing and invasive. About half my weight was on the seat, and about half was on my feet. "Slip your hands into the cuffs," Cindy said. More cuffs? Then I saw them. They were attached to a fixed bar extending out from the back of the chair. I looked up at Cindy, then back at the cuffs. Did I really have to do this? Cindy looked at me with an icy glare. I took a couple of deep breaths to build up my courage and then slipped first one, and then the other hand into each cuff reaching behind my back to do so. They were pink and made of a soft, padded leather, and as soon as my hands were fully in place, the cuffs tightened by themselves grasping my wrists in a snug, inescapable embrace. I tugged at my bonds, but there was no give at all. I was trapped. *tunk* Now what?? Something moved inside the mechanism. I heard more motors whirring. Wait... was that... ? Was something leaking out of the seat? Something slippery? Terrified, I felt something in the seat, right on the fin, and right below my anus. Was it...? *click* "OH SHIT!" Something was pushing into my bottom!! Oh, fuck! Oh FUCK!!! It must have been well lubricated, because it pushed up smoothly and into my rectum with almost no resistance. I panicked and squealed, desperately moving and struggling to get off, but it was impossible. With my arms held tight behind my back and the cuffs around my ankles, I wasn't going anywhere. There was nothing I could do but submit to being anally probed by the sissy pole. I whimpered and squirmed like a frightened puppy, uselessly pulling at the soft, padded cuffs, my new breasts forms bouncing and swaying in the new Sissy Maid's Uniform, feeling heavy on my chest. I was grateful for the bra. "She's likes it," Ed observed. "Yes, indeed," Cindy agreed. I looked at her, my eyes full of pleading. 'How can she possibly say that?' I wondered. 'Can't she see how awful this is??' I struggled some more, but all that happened is that my peenie bobbed and rustled inside my skirts and rubber dildo worked its way in a bit deeper. "That is so hot," Cindy moaned, the two of them watching me. "That's a really good sissy pole," Ed said watching my eyes glaze over with lust before I snapped back to the present. "Fuck, I'm so horny I'm dripping. Turn over!" Cindy took off her panties, throwing them to the side, and arranged Ed so that his head was at the foot of the bed. Then she looked me straight in the eye as both her hands wrapped around his hard cock, stroking it. "Look!" she shouted, seeing me turn my face away. But I refused, scrunching my eyes up tight and shaking my head. I was not going to watch my wife get have sex with another man! But then a High-Res video feed of the bedroom was fed directly into my ocular heads-up. It was a closeup of Cindy, her face full of lust, one hand on his cock and now the other playing with his balls. Ed's face was contorted with pleasure and anticipation. "You can't not watch," she said, smugly. "Please Cindy," I begged, the video feed turning off as I opened my eyes. "Excuse me?" "Please... Ms. Pauline!" I pleaded. "Please don't make me watch!" "I'm sorry, sissy, but this is an important lesson for you. You need to learn that you can never, ever satisfy me with that teeny tiny little peenie of yours. Not like Ed can with his man-cock. Now watch." Cindy sat up and placed the tip of Ed's penis at the entrance to her pussy. As she did, I felt the probe in my bottom pull almost all the way out, so that just the tip was pressing against my sphincter. "Oh!!" I cried out. As she probed her vagina with Ed's cock, I felt the dildo probe the my anus. It couldn't be... could it? But it was! In one fluid motion, Cindy thrust Ed's cock deep into her vagina, and I cried out as simultaneously, the sissy pole thrust its lubricated rubber cock straight up my ass. "Yeah, that's what I need!" Ed yelled. He arched his back, pushing deep, each motion of his cock matched exactly with thrusts by the sissy pole into my bottom. I was getting ass fucked as my wife, on our marriage bed, got pussy fucked by her male lover. But there was more. Ed reached up and grasped at Cindy's breasts, and as he did, I felt the breast forms grab at my own breasts! He then pinched her nipples and I yipped with surprise. My nipples were pinched as well! Somehow, the sissy pole was linked to the video feed and everything they did on the bed it did to me! "NOO!!!" I screamed, trying to get away. But it was hopeless. No amount of pulling or flailing about made any difference to the sissy pole. It continued to plunge into my bottom and abuse my breasts, all synchronized with the action on the bed. But then it got worse: the audio clicked on. It was a feed direct from Cindy and Ed's own implants, transmitted directly into my ears. I heard their ragged breathing, their grunting and panting and the wet, squelching sounds of their bodies slapping together as if I were just inches away, up close and personal. "Oh GOD, oh god! OH fuck!!!" Cindy growled, pressing all the way down on Ed's cock and mashing her pussy into his pubic bone. The dildo in the seat did the same to my bottom, thrusting into me impossibly deep and then vibrating and jerking, making me scream along with them. "Hell Yeah, here it comes!" Ed grasped Cindy's hips and pushed back and with a few short jerks he went over the edge, shooting his cum into my wife, flooding her pussy. Cindy shouted "Oh GODDESS!" at the top of her lungs and orgasmed on top of him, her hair flying everywhere, her naked boobs bouncing and sweaty in the sexy lingerie bra that I had bought for her. And I was forced to watch and listen as they gasped and writhed in pleasure against each other, twitching and cumming. I suppose, technically, Cindy was not being unfaithful. As Cindy pointed out, modern marriage contracts let the woman have as much sex with anyone that she wants. But that didn't make it any less painful, watching my wife get such pleasure from another man while I was forced to watch and listen. Cindy and Ed forgot about me as they gradually came down from their high, his cock still hard and still embedded in her pussy, twitching and jerking as the last of his cum spurted deep into my wife's pussy. They lay like that for a long time, kissing and making out like lovers, tongues and lips and soft breathing. Meanwhile, my peenie was hard and aching, bushing lightly against the soft nylon underskirt of the petticoats, leaving me desperate to spurt but unable to get enough friction to actually make it happen. Finally, Cindy sat up and stretched. Noticing that I was still in the room, she looked me straight in the eye as she slowly lifted herself off of Ed's cock. As it slipped out, their combined juices oozed out of her vagina and flowed over his cock, wet globs of sperm and pussy secretions running down Ed's hard shaft and into his pubic hair. Cindy rolled on to her back, laying against the pillows, looking like a goddess. "Come here," she said. Immediately, the dildo disappeared, the restraints opened up, and the chair dropped to its original position. I pulled my hands free and then carefully stepped out of the ankle cuffs. I took a step towards the bed but then immediately fell to the ground, my legs shaky, my breasts bouncing painfully on my chest. "Come here," Cindy repeated, firmly. I struggled back to my feet, unsteady in the high heels, and walked to the bed. "Lick his cock." Ed's grin was a mile wide. I looked at the disgusting mixture coating his member and matted into his pubic hair, and I had to look away. "Sissy..." Cindy warned. "Y-y-yes... Ms. Pauline," I stammered. Slowly, I crawled over to Ed (who was lying on my side of the bed!), my breasts swaying beneath me, and put my head to his crotch. Oh god, the smell! It was the smell of raw sex: rich and wet and organic and it turned my stomach. "Clean him up, Sissy. We don't have all night." "Yes, Ms. Pauline." I stuck out my tongue and touched it to his slimy pole. This earned me a nipple reward. Encouraged, I licked up some more, tasting Ed's sperm and my wife's pussy juices combined together into a heady, cummy mixture. Slowly I went up and down the shaft, lapping at it, swallowing everything I could, their cum sliding down my throat, coating my mouth. Then Cindy made me lick and suck on his balls and all around his crotch, his pubic hair getting in my mouth as I sucked and cleaned up every last drop. "Now me." I nestled between Cindy's legs where I slowly licked her clean, careful to get as much of her juices into my mouth as I could. The pungent smell of her sex filled me up as I licked deep into her pussy, gathering up globs of Ed's sticky sperm which he shot into my wife's sex and swallowing it all down. I licked and sucked on her pussy lips until she was as clean as I could make her. "Back to the pole!" Cindy growled with urgency, pushing me off the bed and roughly to the floor. I got up on unsteady feet, and staggered back to the sissy pole where I stepped back into the cuffs. In seconds I was trapped like before, the chair pressed against my naked bottom, forcing my cheeks apart, the dildo vibrating and sliding in and out of my anus, my hands cuffed behind my back. This time they went slower, taking a romantic and leisurely pace as Ed slowly fucked my wife, this time with her on the bottom and him on top. My god his endurance was incredible. His cock stayed hard and pressed into her deep places, making her toes curl. She cooed, stroked his back and groped his ass. As before, the dildo in my ass matched his motions. Lost in their own world, they kissed and whispered intimate words to each other all of which was transmitted directly into my ears. And I was forced to watch and listen. It seemed to last forever. * * * Late in the evening, Ed walked up to me with a sly grin on his face. "Watch," he said to Cindy. I had been on the seat for several hours by then and I was exhausted, but still desperately horny, having just been fucked in the ass by the vibrating dildo with simultaneous nipple play and occasional 'nipple rewards' from the breast forms all night long. My hair was wet and matted to my face with sweat. My eyes were heavy lidded with lust I was practically catatonic with a desperate need for release. Ed lifted my skirts exposing my peenie and then lightly stroked it right under the head. With a scream I shot into the air, eyes closed and thrusting my bottom wildly into the fin, my breast forms bouncing painfully on my chest as I spurted. "HOLY FUCK!" Cindy shouted, as my spurties shot half way across the room. "Yeah, she's a randy one," Ed chuckled. * * * Chapter 19: The last day of my punishment period The alarm went off at 5:30am, earlier than usual. At first I didn't know where I was. Why was I sleeping in the guest room? And why was it all pink and white with frilly covers. And why did the bed have a pink flowered lace canopy? But then I remembered. This was now the Sissy room. My room. "I'm a sissy." Was the first thought I had as I realized where I was. My wife was in her master bedroom, sleeping with a construction worker stud after having just been fucked three times by him while I watched. I got out of bed and stripped off the pink sheer babydoll nightie I was wearing. When had I put that on? I tried to remember, but failed. I saw the maid's uniform thrown across a chair in the corner. I'd have to get that dry cleaned. I showered. The experience of showering with breast forms was new. I was naked, and I had breasts! I soaped them and rinsed them as carefully as I could, like Hailey taught me and then shaved my legs and underarms. Out of the shower, I put on a fresh pair of sissy panties. Putting on a bra was a new experience. Helpful Hailey had replaced all of my old bras with bigger ones that could hold my new breasts. Worryingly, she had taken away all of my old ones. Did that mean I would only ever need DD bras from now on? It took a lot more adjusting until the bra felt comfortable, but eventually I got it right. But that was not the only change Helpful Hailey had made to my wardrobe. There were no more pants In my closet. Next to my sheer uniform shirt, was a dark-blue, pressed skirt. Oh my god, I thought, looking at the skirt. It was clearly my new uniform skirt for CICI. Pinned to the skirt was a note from Helpful Hailey. ** Don't forget your stockings and garters! ** it said. I found them in the dresser drawers. The garters are cream lace and the stockings were a light, smoky grey. Remembering my instructions from the milking salon, I put them on, and then stepped into the skirt. As a final indignantly, I saw that my regular shoes were gone as well. In their place was a pair of dark blue high heeled pumps to match my uniform skirt. I finished dressing and then did my morning makeup routing. After neatening up my room, I went to the kitchen where I made coffee, finished up the dishes from last night, and set out a light breakfast which I took into the master bedroom. It reeked of sex. Cindy and Ed were sprawled out on the bed. "Thank you, Sissy," Cindy said, gratefully accepting a cup of coffee. "I know you have to leave for work. I'll have fresh sheets and a clean bedroom when I get home tonight?" "Yes, Ms. Pauline," I said, looking at my wife with desperate eyes. "Wake up my stud." Right in front of me, Cindy sought out Ed's mouth and kissed him. "A quickie before work?" he asked, waking up. "You read my mind," Cindy grinned. * * * My breasts were true sissy tits, large and bountiful, and just about everyone on the looper was staring at them. After all, a Sissy commuting to work in a data processing uniform was not that common. I showed up at work and endured the gasps of my colleagues as I walked across the office, everyone muttering about my new tits and the skirt I was wearing. I know now that they all thought I represented their future, and they were right. Work that day was routine. They must know, I thought to myself. Ms. Jensdotter was actually kind to me. She complemented me on my latest analytical product. "You really are a gifted data analyst," she said, looking over the numbers. "You've managed to squeeze another one point two percent of margin when the machines said it was impossible. Impressive." "Thank you, Ms. Jensdotter," I said. For some reason, her praise didn't give me the flow of pleasure it usually did. I felt sad and despondent. "I know you've had a rough time of it recently," Ms. Jensdotter said. "But you'll adjust." A rough time? Did she know? "Yes, Ms. Jensdotter. Thank you, Ms. Jensdotter," I said. "By the way, your milking sessions are cancelled for today." I checked my calendar on my heads-up and realized she was right. Who did that? It must have been Cindy? * * * "You're wearing a skirt," Jamie stated the obvious. "Yes, my wife..." I choked down a sob, "she... is so nice, that... I... she..." I looked at James, trying my best to mask my expression. "She and Ms. Jensdotter decided that I could wear skirts to work now. I am so happy with it." But Jamie could tell from my eyes what I was really feeling. He gave me a hug. "I'm so jealous," he said. "I was promised a skirt too, but they weren't available in my size. You must have gotten the very first one!" "Yes," I agreed. "It is such an honor." I winced, hoping the sarcasm monitor didn't catch that. "And you have such nice big breasts now too," Jamie said. "My wife... she promised she would get them for me, but..." I just shrugged. As I did, my new breasts swayed inside the bra. They were so heavy that I was beginning to feel an ache in the muscles in my back. "Well, enjoy your skirt." Jamie gave me another hug. "Join me," he whispered into my ear. I looked at Jamie, shocked. "I need my friend with me," he said. "I miss you." I just walked away. * * * After work, I left the office building and started walking to the looper. At home I knew I had dinner to prepare and a lot of cleaning up todo. After all, last night's activities... Last night. Last night when I was forced to watch my wife get fucked by another man. Images of her screaming with pleasure as she thrust against him ran through my head, followed by images of them pressed full-length against each other, his cock deep inside her pussy, bodies writhing, kissing deep and lost in each other. At some point I just stopped in the middle of the sidewalk. Commuters heading home streamed around me, annoyed that I was diverting their flow. But I couldn't seem to move. I tried to continue, but I just couldn't. I just couldn't. * * * "Charlie!! Are you a sissy now?" "Creampuff, I'm so glad you're here." We hugged. I had tears in my eyes. "I just want," my voice cracked and had to take a moment to pull myself together. "I was just looking for a new bra, and maybe a sissy casual dress to wear while doing work around the house?" Creampuff looked at me and understood immediately that I was lying. I grasp her hand, and while looking a way, I wrote "HIDE ME" on her hand with my finger. Creampuff's eyes went wide with alarm. "Of course, Sissy Charlie!" Creampuff said with forced enthusiasm. "We've just gotten a brand new line of Victorian Sissy Wear! It's perfect for wearing around the house, and the bra's are just amazing! But have you changed? Are those breasts I see? They look amazing! So big! And your waist. Does it look thinner? Come with me over here where you can strip and I can measure you!" I followed Creampuff behind a curtain into a short hallway. "I'll let you undress here." But then Creampuff wrote FOLLOW ME on my hand, pushing me down to the floor. She then turned and disappeared behind a curtain hanging on the wall. Following her on my knees, she led me through a metal door, a short corridor and then another door. Inside was a utilitarian changing room, obviously for the sissies who worked at the store. Creampuff was facing away from me, her bottom about level with my face, frantically pointing behind her back. I quickly crawled under the countertops where she was pointing. Creampuff disappeared for a few minutes, and then came back. "Maybe I dropped it down here?" she said, loudly, obviously speaking for the cameras. She ducked under the counter counter to my right. "Charlie?" she whispered. "Creampuff? Thank you!" "Sshhhs!" she shushed me. "The counters are metal, so they block the network. Like a Friday cage." "Really?" "Yes, really. You're off the net as long as you stay down here. And the door from the store blocks the camera when it's open, so hopefully no one knows you're here. Don't get out! I need to get back to work. I'll be back in a couple of hours. I've told the girls we have a special guest, okay? Sometimes we get special guests, so it's okay. It's not unusual. But you need to treat them nice. Okay?" "What do you mean, treat them nice?" She shrugged. "You know. Nice. Sissy nice. I have to go!" Creampuff backed out. "Found it!" she trilled, showing her earring. She then went back to the store proper. The counters clearly served as dressing tables for the sissies getting ready for work. I did my best to get comfortable. There was so little room and the counter legs were too narrow for me to move more than a half a foot in either direction. Leaning against the back wall I found a kneeling pillow, like at the milking salon. 'But why would there be a kneeling pillow under a sissy dressing table?' I wondered to myself. 'Who would want that?' Just then, the door from the outside banged open and three sissies entered. "We have a special guest!" one said, excited. "Yes! I got the note from Creampuff!" said another. "Oh! There she is! Me first!" A sissy pulled up a chair and sat down in front of me, scooting up to the counter. Suddenly, I was surrounded by sissy legs and feet inside petticoats, frilly garters and stockings. The legs rubbed against me, the skirts brushed against my face and nose. "She's not doing anything," the sissy complained. "Creampuff said she was a virgin sissy. Maybe she needs some encouragement?" "Okay!" I felt something moving in my lap. It was her feet! She was wearing high-heels (sissy street shoe style - not as high and more durable than fetish style), and it looked like one foot was tapping or pointing to the other? Did she want me to touch her feet? I reached down and grasped a foot. She was wearing sandals and so most of her stocking feet were exposed. I used my fingers to give her a foot massage. "Ohmmm... that feels nice," she sighed. "What's she doing?" "She's massaging my feet. I think we have a foot fetish." "Oh, wonderful!" She pointed with one toe to the buckle of her other foot. I took the hint and unbuckled both her shoes and put them to the side. Now I could massage her feet in earnest. I had done this for Cindy loads of times, so I was pretty much an expert and soon I had the sissy moaning with pleasure. "Sounds like she's good at it!" "Oh, so nice! Such nice soft hands." "My turn!" "Just another minute! She's not done yet!" Her foot raised up, brushed across my breasts and nipples (transmitted by the breast forms to my own breasts and nipples) and then raised up pressed into my face. Because of the low countertop, there was no room to back away. I was filled with the smell of sissy foot sweat, faux leather from the sandals and baby powder as she pressed the foot into me, squirming it around. "Come on, my dear," she said. What does she want? I wondered. Finally, I realized. I lifted my hands and cradled her foot and kissed it. "That's my sweetie pie," she sighed. "Now the other one." Her other foot was pressed into my face. Again, I placed a gently kiss on it, right under the toes. "More kisses!" she squealed, bouncing in her seat, clearly delighted. Oh my gosh, my peenie was hard! I kissed her foot all over, then switched back to the first one and give it a dozen little kisses as well. My face now covered with her sweaty foot smell. "That's enough!" whined the other sissy. "My turn!" "Oh, Pooh. Fine." The first sissy fetched her shoes and disappeared. The next Sissy sat down and scooted the chair under the countertop. She was wearing short satin and lace skirts with petticoats, silky stockings with satin ribbon-bowed garters. She kicked off her shoes and immediately held her feet up to my face. "Ohhhhmmmm..." she sighed as I kissed her feet. Her smell was stronger and more intoxicating, since she had been wearing close-toed pumps. I realized how excited I was. But what did that mean? Was I really a foot fetish? Was I really getting off on kissing Sissy feet, stuck under a dressing table an unable to escape? I moved on to little nibbles and licks, eliciting even more sighs from my Sissy customer. She switched feet and then I did the same thing to her other foot for a while. "Oh dear! Oh DEAR! Oh No!" The sissy squealed. The foot was jerked away and frantically a pair of hands reached under the countertop and grasped me around the head. After some frantic fumbling with her skirts, she pulled my face deep into her Sissy crotch, where a hard naked peenie and pair of num-nums were sticking out of lace hole in the front of her silk and lace panties. Frantically, she pressed her member into my mouth. It all happened so quickly! I had no time to react or resist, and about the only thing I could do was act on instinct and open my mouth and start sucking on her hard peenie. "OH! Oh GOODNESS!" she squealed, as she pulled my head forward, thrusting her little peenie all the way in. In this instant, I'm not quite sure what I felt. First, a Sissy's peenie is so much smaller than a man's cock, like Ed's. It's like sucking on someone's finger. Or a lollypop. My first reaction was "how adorable!" as I wrapped my lipstick lips around her little member. But there I was, nuzzling another Sissy's crotch, enveloped in her slip and poufy petticoats and skirts, my face pressed against her satin panties, the strong smell of her crotch and her num-nums and her baby powder in my nose, with her peenie deep in my mouth! "NOW! OH DARLING!" she said, thrusting forward frantically a couple of times and then I could feel her little peenie spasming and jetting her sissy cream down my throat and filling my mouth. "Are you spurties?" The first sissy gasped. "No fair! I want her to drink my spurties!" I tried to pull away. "Not done yet!" she growled, her hands holding me in place. My mouth was now so full of her sissy cream I was forced to swallow. Some escaped and dripped down my face and onto my breasts in the office blouse. I took a quick breath out of my nose and then swallowed a second time. It was sweet and runny. Like if you mixed egg whites with some cream and sugar. I had heard that Sissy cream was actually sweet and creamy, but that was the first time I had ever tasted any. Apparently Sissies are on some special diet and take some special medicine to make their emissions taste that way. I wondered if my cream might might be sweet and creamy like that some day? The sissy thrust a few more times and had a few more weak spurties which I sucked down and swallowed. When she was done, I took a second to lick and clean her little peenie, including her soft, hair-free num-nums before she finally pushed her chair away from the countertop and got up. "Finally!" The first one said and was just about to sit down when I heard a chime. "Customers!" said a woman's voice over the loudspeaker in a high trill. "Oh, yay!" Both of the sissies jumped up, put on their shoes, arranged their skirts and rushed out to the sales floor, giggling and excited. * * * What followed was a continual stream of sissies coming in and out of the back-room dressing area. There appeared to be no specific "shift change", just sissies called in to work whenever the algorithms predicted an increase in customers, and then they were told to leave as soon as the need went away. This meant that I barely got a minute or two to rest before another sissy would sit down, scoot her chair in, wrap her legs around me and pull my face into her lap. By the time Creampuff was let go, I had nuzzled and sucked on dozens of peenies, licked many pairs of num- nums, and had kissed and fondled dozens of pairs of legs and feet. I was a mess and smelled strongly of sissy cream and sissy feet. Inevitably, with all of those spurting peenies, I ended up getting sissy cream all over my face, in my hair, and splattered all across my sheer work blouse. I tried my best to clean myself up (by gathering as much sissy cream as I could and licking it up, mmm), but there's only so much you can do. But the real problem was how horny I was! The sissies soon learned that I would give them extra special service if they slipped a foot under my work skirts and stroked my peenie in its own sissy panties with their stockinged toes. Since I hadn't had either of my two milkings that day, my need for my own spurties shot through the roof! But there was no time for me to stroke my own peenie. I was kept constantly occupied by work Sissies sitting in my cubby, their delightful satin and silk, ribbon and lace skirts and petticoats surrounding me and enveloping me, their needy peenies begging to be sucked and their poor tired toes aching to be kissed and sucked... it was all I could do to keep up. I had no time for any sort of self pleasure or break from my duties. Until finally Creampuff's shift was over. She first went into a back room, and then returned and quickly dodged under the counters to talk to me. "Sissy Charlie!" she whispered. "Oh! I see *someone's* been having a good time!" I gulped a few times to fully swallow the last load of sissy cream which had shot into my mouth, and ran my tongue around trying to get the slimy, creamy, sweet taste out of my mouth. "I did my best," I said. "You told me to 'be nice'..." "Oh, sweetie! You were more than just nice! You were amazing! The girls all gave you five stars! The want you back anytime! They even put together some sissy credits to give you a little token." "Sissy credits?" "It's a sissy thing," she shrugged. "A sissy-only crypto currency. We're not allowed to have actual money, but we can exchange sissy credits. They're not useful for much out in the real world. But sissies exchange them you know, to swap clothing or services." "So I have my very own sissy credits now?" I asked, my voice trembling. "Yes you do. You're a professional sissy now." I thought about that with a sinking feeling in the pit of my stomach. I couldn't deny that I'd had fun being the plaything of all of the sissies in the sissy store. But it made me wonder why am I running away? Am I already a sissy? What am I willing to do? Where am I going? But I had no answers. All I knew was that I couldn't go home. I just couldn't do that. "She's the one who needs her chip zapped?" A burly, man knelt beside me. I shrank away, terrified. "Hey Jacob!" Creampuff trilled. "It's okay, Sissy Charlie. Jacob's our Sissy Admin. He makes sure we behave, don't you, Jacob?" "It's a full-time job," he growled. Jacob had sloped shoulders with a three day growth of beard and a paunch. "Give me your neck," he reached under the counter and grabbed my arm. "Wh-what?" Frightened, I shrank back under the counters as far as I could. "Charlie, it's okay!" Creampuff assured me. "The only way to get out of here is if we disable your chip. Jacob will zap it for you." Oh god. Jacob showed me the zapper. It looked like a taser, but with a kind of claw-like structure at the tip. I had heard these existed, but that was the first time I had ever seen one. "W-w-w-ill it hurt?" I asked. "Naah," Jacob said. "Just a little sting." Shaking, I exposed the back of my neck. Jacob felt for and found the nodule where my chip was implanted. Placing the claw of the zapper on the chip, he pressed the button. "FUCK!!" I shouted, my body jerking violently of its own accord, my head banging painfully up against the countertop. "Oh, Charlie! Are you okay??" Creampuff asked. "Ohhhh..." I moaned, rocking in pain, both from the zap as well as from the bump on my head. "You said it wouldn't hurt!!" "Yeah, well, I lied. C'mere, gotta check it," Jacob pulled me roughly forward and held the butt end of the zapper to my neck. It glowed green. "You're clear," he said. "Get out. I've shut down the cameras." I crawled out from under the countertop, feeling woozy from the pain, rubbing my neck. "Oh, sweetie, let me help you with that," Creampuff said. She fetched a bright pink faux leather purse decorated on the outside with sparkly rhinestones spelling out "Sissy" and lined on the inside with silky satin. Pulling out a tube, she rubbed some ointment into the scorched spot on my neck. "It will moisturize and help numb the pain," she said. "Thank you, Creampuff," I looked at her, gratefully. "Oh sweetie," she hugged me and kissed me on the lips. "We sissies need to stick together." "AHEM," Jacob cleared is throat. We both looked over. "Oh, ah..." Creampuff held me for a second. "What is it?" I could tell that something was wrong. I hugged her to tell her it was okay. "Jacob, uh, doesn't do these things for free," Creampuff said, looking down at the floor, embarrassed. "I talked him down as best I could, but..." "But Creampuff... I don't have any money of my own. Cindy... my wife... she controls all of the finances." "Oh, I know that, Sissy Charlie. Money is not what Jacob wants." I looked over at Jacob who looked back at me with a predatory smile, his teeth showing. "Then what?" "He wants... you know, what only a sissy can really provide." "Do I need to..." I started to sink to my knees. "No," Jacob pulled me roughly to my feet. "Not here." "I'm so sorry!" Creampuff kept saying, over and over, as I was dragged, stumbling through the narrow back halls of the sissy store, my breasts bouncing painfully. Jacob pulled me into a small room labeled "SPR-3". It was decorated like a Sissy boudoir with pink walls and dark pink trim. It had a small stand-up closet in one corner, a narrow dressing table with a mirror, and a narrow love seat in worn pink vinyl. The floor was covered in a pink patterned linoleum. In the middle there was what looked like a one-person pew, with a place to kneel, and a railing (both made of heavily padded pink faux leather). "Get in position," Jacob said pushing me towards the contraption in the center. "But... what am I..." I looked at it, not knowing what I was supposed to do. I looked over at Creampuff for help and she just mouthed 'sorry' again and dropped to her knees. "Hey!" I shouted and jumped back, as Creampuff reached under my skirts. Jacob smirked. He was enjoying this. "Please, Charlie, I'm so sorry! But you have to start paying your debt to Jacob or he'll turn us both in!" "Turn us both in?" I gasped. "To whom?" But Creampuff just stroked my legs a couple of times and then reached under my skirts and pulled down my panties. Embarrassingly, they got caught up in my hard peenie, and so Creampuff had to reach up and pull the sleeve off, the lace and the satin and her fingers stroking down my member as she did. Then Creampuff led me over to the pew and had me kneel down. The kneeling bench was about a foot higher than a real pew, lifting me up. Oh no... Next, she pushed me forward so that my torso, just under my breasts, was resting on the padded railing. My breasts hung down, over the railing. Please god... no... I looked up at Creampuff as she walked in front of me. She took each of my hands and placed them on dowels sticking out from the front of the pew. "Creampuff!" I gasped, horrified, as she pulled two heavily padded shackles from slots on the from of the pew and wrapped them my wrists, locking them into place. I was so shocked, trying to interpret what she was doing, that I didn't even struggle or move away. I just let her do it. "Charlie, I'm so sorry," she said. "But this is the only way!" "What are you doing? Creampuff??" I cried as she pushed my skirts up to expose my (now naked bottom) with my (still hard!) peenie now pointing straight down at the kneeling bench, hanging in the air. I could feel the garters from my stockings frame my bottom as they stretched taut. Creampuff pushed my legs apart and then shackled each leg with a large padded leather cuff placed just above each knee, fastening the cuffs somewhere to the left and right of the pew so I couldn't pull my legs closed. "Eep!" I squealed, as Creampuff pulled out the jewel from my bottom and replaced it with something cold and wet on my sphincter. It was a thin rubber nozzle attached to a bottle of lubrication which she squirted into my bottom until it dribbled out, falling in wet plops below my crotch on the pink vinyl padding on the kneeling bench. "Oh, how I love to watch 'em squirm," Jacob said. He unbuttoned his belt. "Give her an O-Gag." O-Gag?? Creampuff opened a drawer of the dressing table and fished out a round pink oval with what looked like a big pair of puffy lips attached to it. "Sorry," she whispered, again, as she knelt in front of me. Creampuff grasped my hair, hard, and then roughly pulled back my head. Shocked, I cried out, but as I did, she stuffed the pink oval into my mouth, setting it so that my teeth were caught in channels around the outer edge. I desperately tried to eject it with my tongue, but every time I opened my mouth, it expanded further with some sort of ratchet, until my mouth was wide open and there was nothing I could do to close it. Looking in the mirror, the the front of the gag had ridiculously fat, puffy, cock-sucking lips, inflated and soft like balloons. I looked like something halfway between a sissy and a blow- up sex doll. "Perfect," Jacob dropped his pants to the floor and stood in front of me. He was naked underneath. Bent over the padded railing, my head was about even with his stomach. My eyes were teary and I was breathing hard. "I love breaking in new sissies," Jacob said, grasping my chin and tilting my head up to look him in the eye. I could feel tears leaking out and dripping down my cheek. "Ever been in a Sissy Prayer Room before?" I shook my head, no. I once had heard two guys on the looper mention a Sissy Prayer Room. Is what they were talking about? "A Prayer Room virgin, huh?" Jacob was suddenly more interested. "Excellent." He showed me his arm and pointed to a tattoo with a series of short lines, crossed out in groups of five. "Those are the virgin Sissies I've deflowered in Prayer Rooms," he bragged. From the tattoo, it looked like I would be number 26. He slapped me hard on the cheek. "Ahhhnnn...!" I gasped, shocked at the pain. "What about oral? Ever done oral? Other Sissies don't count." I blushed and nodded. "Oh well. Practically impossible to find a sissy who hasn't done oral. Anal?" I shook my head, 'no'. "Excellent," he grunted. "A Sissy Prayer room deflowering. I'm going to save this video for a long, long time." Video? This was being recorded?? Jacob knocked the dowels to the left and right, spreading my arms and causing my torso to drop down lower. My new breasts bounced heavily from my chest in the bra which strained to contain them. My face was now level with Jacob's naked crotch. I felt the first drops of drool leak out of my gag and drop wetly onto the pink linoleum floor below. With his fingers, Jacob pushed his soft, fat cock past the soft, puffy fat lips of the O gag. It felt like a hot, fat worm filling my mouth. "Suck it." Because of the gag, I couldn't suck it like I'd been taught, but I did my best. I used my tongue to stroke it and play with it, running it all around and over the head and in the tip. Ugh, I could taste his urine and sweat and musk, and old dried lubricant. How often did he use Sissies in these prayer rooms? "Mmmff!" I whimpered. What was that? I squirmed on the bench. Creampuff had grasped my peenie and was stroking. Her hands were slippery and well lubricated. "Her peenie's already nice and hard," Creampuff observed. "Born to be a sissy," Jacob observed with satisfaction. "Sissy to the core." Jacob's cock was getting harder, filling my mouth. He mashed his crotch into my face, pressing my nose and cheeks against his rough, wiry pubic hair. Semi-hard, he gradually worked his member deeper and deeper down my throat, thrusting slowly in and out. 'Was I born to be a sissy?' I wondered. 'Was I really a sissy to the core? Just because my peenie was still hard even though this awful man had shackled me to a Sissy Prayer Pew and was now forcing his cock into my mouth?' Creampuff reached a hand around to the front of the pew and began to play with my breasts. She squeezed them and pinched the nipples, all of which was transmitted by the forms to my actual breasts and nipples, making me squirm. Soon she had me panting in pleasure. Since my milkings had been canceled, had not get had my spurties today, and so it didn't take much. Sensing that I was getting too close tot he edge, Creampuff stopped stroking my peenie. "Need to keep you on simmer," she whispered into my ear, licking it wetly. "Jacob doesn't want you to come. Remember, this is all about *his* pleasure. Sissies exist to serve real men and women in any way we can." Jacob grunted in agreement and grasped my head with his meaty paws. As he thrust in and out, his cock sliding past the fake pink lips of the o-ring gag and to the back of my throat, I worked at his shaft with my tongue as best, also contracting my throat muscles where possible. "She's well trained," Jacob acknowledged. "A natural born cocksucker." Oddly, the o-ring made cocksucking easier. I didn't need to worry about my teeth and I could just focus entirely on his shaft. The only real problem was the stream of drool which was now continuously leaking from the gag creating a pool on the floor. No wonder the floors were made of easy-to-clean linoleum. As Jacob got harder, his thrusts increased in violence and his cock started to bump against the back of my throat. My breasts were now swinging back and forth with each thrust, the forms pulling painfully at my skin despite Creampuff holding and fondling them. Thank god for the bra! It would have been a hundred times worse without it! Finally Jacob was fully hard. Grasping my head, he pressed his dick to the back of my throat, and then probed at it with a series of small jabs before he found the right nudge and thrust it down my throat. "OH YEAH, Now THAT'S what I'm talking about!" he shouted as my neck bulged with his hard member. "That is so hot!" Creampuff squealed. She reached back to stroke my peenie, discovering that I was still hard. She quickly me brought me to the edge, then released it, leaving me whimpering with need. I was now being truly face-fucked by Jacob. He slapped his crotch into my face over and over, his cock sliding down my throat, my breasts jiggling and bouncing. Tears and drool and snot streamed down my face as I gagged and couldn't breathe with this hard manly shaft down my throat. Being used like this, in such a raw and animalistic way... it touched something inside me. It was a level of submission I had never before experienced. Thank God, Jacob didn't last much longer. With a loud scream he came, shooting his first load straight into my stomach before pulling out. His second shot went straight into my mouth covering my tongue with his salty jism and his remaining shots went right into my face hitting it with a force that seemed super-human. "Oh yeah, oh yeah," he chanted as he continued to paint my face with his sperm, using the tip of his penis to rub it all over. But what about me??? Creampuff?? I jerked and thrust my peenie, desperate for spurties, but Creampuff just pulled away from both my peenie and my breasts, leaving me humping air, my ass bouncing up and down trying desperately to cross that threshold. Seeing this, Jacob laughed out loud. "That's a hot sissy bitch!" he taunted as I desperately tried to get off, thrusting and moving back and forth, my peenie wildly swinging back and forth. "Lovin' you the taste of some hot sissy-admin spunky action, ain't that right??" But all I could do is moan and whimper, embarrassed and blushing, my mouth full of sperm and Jacob's cock, and beg Creampuff with my eyes to finish me off, but she refused. Eventually I calmed down and eased down from the brink. Jacob pulled out and a river of slime drooled down my chin and onto the floor. My face was now covered in Jacobs sperm. It had also splattered all over my blouse and had gotten in my hair. The floor in front of me was a wet, slimy mess of sperm and drool and tears. "I'm going to enjoy these pictures for a long, long time," Jacob said, satisfied. "Have you ever been face-fucked with an O-gag before?" I shook my head, no. "Sweet. That's close enough to virgin oral for me. I'm claiming it." It took me a second before I realized he was referring to the tattoo marks on his arm, one for each virgin sissy he had conquered. I would now be immortalized on Jacobs arm, forever. I wondered briefly if he might be done with me. Maybe that was it? "Fluff me up, buttercup," he said to Creampuff, who quickly dropped to her knees and pulled him into her mouth, not hesitating at all. My heart sank. If he was being fluffed, then I knew what would be next. "Mmmm, I so love your taste, Jacob," Creampuff said. "Yeah, you bitches love some real man sperm, don't cha?" "Mmm-mmm, good," she sighed, licking his man-pole clean. But then Creampuff looked over at me and winked. Oh my god, it was all an act! Soon, Jacob was hard again. What is it with these men? Isn't one orgasm enough anymore? Is there something in the water? Some special man-drug they take? Or are they being societally-bred to need to fuck multiple times in a row? Before she let him go, Creampuff pulled a tube of lubricant from her skirts, warmed it up in her hands, and squirt it all over his cock so it was nice and slippery. As Jacob walked behind me, Creampuff removed my O-ring gag by first squeezing it from the outside (so it got even wider) and then pressing some special spot on the inside. I stretched and worked my jaw. With the gag removed, my mouth felt extra large, as if stretched ('To handle extra large cocks', a little voice in my head said). "Time to skewer me an anal virgin!" Jacob crowed, slapping my bottom with his hard penis. "Now you behave, Sissy!" He spanked my bottom a couple times, leaving angry red hand-prints. "OH GOD!" I cried, as he pushed it right in, just like that. "That's it, Sissy!" Jacob shouted, as if he were riding an untamed horse. "Pray to your Sissy God!" "Oh god, oh god OH GOD!" I shouted over and over as he slowly pressed his hard rod deep into my bottom. "Whew," Jacob whistled. "She's a TIGHT one! You really are an anal virgin, aren't you??" "Oh god, oh god--" I kept repeating. Creampuff reached underneath me and grasped my peenie, now harder than ever, and started to stroke it, ever so slowly. With her other hand, she took the bottle of lube and squirted it down my ass crack, where it dripped onto Jacob's thrusting cock, keeping my anus nice and lubricated. I felt so full. He was big, bigger than my largest jewel. Amazingly, I only felt a bit of pain. I felt grateful for the anal training I had to endure at the sissy milking salon. They had prepared me well. I was gasping and out of breath and shouting "oh my god" over and over and over. Jacob was right. I was praying. Praying to the sissy gods. As his cock stroked past my prostate, it sent me into orbit. I felt a glimpse of heaven. I'm being fucked in the ass, I realized. A man is fucking me in the ass. There's a cock up my ass! I felt invaded and used. Taken. Jacob pulled out. As he did, his cock would get more lubrication (thank you, Creampuff!) and then he would push back in again. Eventually, I loosened up a little more and, with a grunt, Jacob started thrusting in and out with more speed. As he did, Creampuff began playing with my tits with her free hand, pinching the nipples and grasping and the breast forms. Her stroking of my penis slowly increased, along with Jacob. Just then, Jacob pulled nearly all the way out, leaving only the head of his penis embedded in my anus. Then he firmly and smoothly thrust it all the way in. "OH FUCK ME! OH MY GOD!" I yelled, feeling truly and thoroughly impaled on his fleshy rod. "That's my sissy bitch!" he crowed. "Pray to your sissy god!" Jacob did it again, pulling almost all the way out, before thrusting all the back in, faster this time, slapping his body against my bottom. "GOD! GOD!" I cried out. "ONE MORE!" Jacob shouted Creampuff put her whole hand on my peenie now, stroking it quickly and grasping it tight around the head, her fingers doing evil magic things. Jacob pulled back one last time and held it there, doing little thrusts, teasing me. "DO IT!" I cried, all pretense abandoned. "FUCK ME! PLEASE FUCK ME!" "THIS IS IT!" Jacob shouted, thrusting all the way in in one swift motion. "OH, PLEASE, GOD, OH YES, OH GOD, OH FUCK! OH PLEASE!" I cried, in tears, catatonic and incoherent as Jacob jackhammered my ass, with small quick thrusting motions, pulling out about an inch before thrusting back in, my body setting up a counter motion, his balls slapping at my little num-nums. "OH, YEAH!!" He shouted, pushing me forward all the way and twitching for a second before he shot his first load into me. "GOD, YES, OH MY GOD!!" I cried out as Creampuff pulled on my member and I spurted, my peenie spraying my sissy cream all over the bench and the back of the Sissy Pew. Jacob pulled back and then thrust in again, shooting his second load deep into my bottom, before pulling back and spraying his third and forth shots of spunk all over my bottom. "Now THAT's what I'm talkin' about!!" Jacob said, shouting with glee. "I broke me in another Sissy! You'll never forget your first, Sissy. And I won't forget you either, because I'll have your mark on my arm forever." Eventually, Jacob's twitching orgasm subsided, and my own spurties finally finished. I lay over the pew and hung my head, wet, sweaty and exhausted. My ass felt sore and abused. Jacob's spunk ran down the insides of my legs, dripping out of my ass as it clenched and unclenched, onto the vinyl padding below. Oh my god, I thought to myself one last time. * * * Chapter 20: Creampuff's Apartment Creampuff unshackled me and the two of us cleaned up the room. First, Creampuff wiped me down and then the two of us wiped down and disinfected the room. "Really Sissy Maid work," Creampuff smiled, shrugging her shoulders. She looked up for a second, staring at her heads-up. "Good news, Jacob says your debt is paid in full." "I should hope so," I said. I was exhausted and fully drained. I felt as if I could sleep for a week. "Oh, I almost forgot!" Creampuff says, as we were about to leave. "Strip!" I stripped off my splattered work clothes down to panties and a bra while Creampuff dashed out of the room, returning a few moments later, her arms full of Sissy clothing. "Cameras," she explained, as she stripped off her sissy work dress. "Video in Sissy Prayer Rooms are privacy protected. Jacob paid for it, so he owns it and no one else can see it without his permission. But now that Jacob's gone home, the cameras in the hallway will be monitored, as well as on the way home. So we need to cover up. Ooo! I've been waiting for a reason to try these!" Creampuff squealed with delight. And no wonder! The outfits she chose for us were the most effeminate, Sissy fantasy fetish outfits I had ever seen. First, I was dressed up in garters with wide satin and lace straps. The garters had elaborate bows at the top, just where they attached to the cream-colored silk stockings. Then Creampuff showed me the two matching dresses, a lemon yellow one for me and a baby blue one for her. "Pink always sells out first," Creampuff explained. "So when these floor samples fell out of season I snapped them up! Aren't they just delicious?" The dresses were high waisted baby party-style. The skirts were very high, starting just under my breasts and flaring out to almost vertical at my hips layers and layers of petticoats. Creampuff opened my dress and I stepped into it, threading my arms into the sleeves and standing patiently as she zipped it up in back. Then I did the same for her. "But... but..." I sputtered, seeing my reflection in the mirror. "My panties will be exposed. And my peenie!" "Don't worry, we have bloomers!" Creampuff said, excited. She held out my pair (yellow, like the dress) and I stepped into them. The bloomers covered my panties with ruffles and satin, but left my garters and stockings fully exposed. My peenie poked against the front of the thin, shiny fabric like a hard little tent pole. Next, Creampuff had me put on a pair of white satin opera gloves, a pair of lemon yellow ruffled socks (over my stockings?), and a pair of black shiny patent-leather high heels that buckled on. Then Creampuff pulled me over to the dressing table and sat me down. "Makeup?" "Part of the disguise," Creampuff explained. She used concealer and foundation over my face, giving me a baby-like complexion. Then she added long eyelashes, making them even longer with mascara, then wide baby-like eyes and deep red lips. She finished it off with bright, blushing cheeks. "Now for the pi?ce de r?sistance," she grinned. Creampuff pulled out a large silk cape with a six inch satin collar! She draped it around me and fastened up the buttons down the front of the cape first and then up the collar. The collar was so wide and so high that I had to stretch my neck up just to see over it. Like the dress, the cape ended just below my waist, which meant my bloomers were still exposed. "I think we need a Goldilocks wig," she said, looking at me critically. Creampuff found one in the dresser and put it on me. She then fussed with the hair, adjusting it and tidying it up until she was satisfied. The tight golden curls cascaded down my head and flounced as I moved my head. On top the wig Creampuff added a large floppy bonnet of satin and eyelet lace which was closed around my head with a wide brim. Now my vision was even more restricted to barely a tunnel between the cowl of the cape and the brim of the bonnet. It was like Sissy blinders had been put on me. "Here's your purse," she said, giving me a light-yellow purse on a long strap. I was required to hold the purse in my right hand, delicately between the thumb and fingers, holding my hand out with an effeminate tilt to my wrist. "Perfect!" Creampuff clapped, delighted. "You are the epitome of the sweet sexy sissy! No one would guess you are runaway Charlie. Now I'll get dressed and we can get out of here." Once Creampuff finished dressing, in an matching, powder-blue outfit to mine, she bundled up all of our old clothes. "I'll just put these into my locker," she said, grinning. "But... but... But those are my work clothes," I said, plaintively. But Creampuff had already disappeared. "What will I wear now?" I wondered. When Creampuff got back, she threaded a yellow leash between the buttons of my collar and fastened it to my sissy collar. With a tug, she led me out of the room, down the hallway (my high heels clicking on the cement floors), and then out the back door into the alley behind the store. * * * I felt simultaneously exposed and covered up. Exposed, because the skirts were so high and flouncy that everyone could see my bloomers and stockings and the skin on my upper thighs above where the garter tabs were fastened. Worse, if they looked closely, they could see my hard peenie tenting out the front of the bloomers and swaying back and forth as I walked. I looked like such a ridiculous yellow Sissy Pouf-ball that I blushed bright red, walking out in public. Fortunately, there was almost nobody around in the back alleyways behind the store. But the few people I did see looked at us with disgust, one Sissy leading another on a leash, both of us mincing home in little steps in our high heels and stockings and garters. I was grateful for the cape and the bonnet because they hid my face. But they also made it practically impossible to see where I was going. The high white satin neckline on the cape was like a high wall around my head, and the bonnet covered me up with a wide brim. I had to practically turn my entire body in order to see to the left or right. More than once I stumbled as I misjudged a step or a curb. It was also weird to be off the 'net. I kept trying to bring up the map, but there was nothing but connection errors and red hardware icons on my heads-up. I looked around, wondering what would happen if someone drove up and kidnapped me. There would be nothing I could do about it, I realized. They could take me to wherever they wanted and have their way with me and no one in the world would ever be able find me. "How much further?" I whined as Creampuff led me deeper into the Sissy ghettos, well known blocks of public apartment housing built by the state and reserved for Sissies. I had driven past them once, but I had never been inside. "Just a few more blocks," Creampuff tugged on my leash, pulling me forward. As we minced and pranced our way to her apartment, me holding my purse up with one hand, wrists bent, my other hand went automatically out on the other side to balance myself, wrist also bent. My skirts and cape flounced around my hips, my peenie bobbed, and my breasts bounced and swayed with every step. We must have made quite a sight, not one but two sissies in our matching sissy party dresses mincing down the street. After what seemed like forever, with my toes starting to get pinched and my calves aching, we finally reached her apartment. "I hope you won't mind," Creampuff apologized. "My apartment is pretty small. I don't have much Sissy Seniority." She pulled me by the leash to a side door and tapped her wrist to the sensor. The door opened and I followed her into a small foyer with an elevator. "Down?" I asked, as the elevator descended. "Yes," I could tell Creampuff was embarrassed. "There's actually more stories underground than there are above ground. I don't mind. At least the temperature is constant." The elevator opened to a narrow hallway lined with doors on both sides, set close together. We click-clacked in our heels almost all the way to the end of the hall before she stopped and pressed her wrist to a keypad. "My humble Sissy lair," she announced, opening the door. "It's cozy," I said, walking to the center of the room. In truth, it was like a walk-in closet than an actual apartment. Shelves and hanging rods covered the entire left hand wall, from the front door all the way to the back of the apartment. Various throw rugs, pink pillows and stuffed animals were strewn around the floor. "I know it's small," she apologized, helping me with my cape and bonnet. "But it's all we're allowed." "We?" "Me and my roommate." "You live here with a roommate?" I gasped, then immediately regretted it as Creampuff blushed with shame and looked away. "It's the life of a working Sissy," she shrugged. "I don't mind, really." "Of course you don't," I said, trying to recover, "not with all of these fabulous clothes!" "Oh, I know!" Creampuff said, excited. "I'm the envy of the entire floor! Working at a Sissy Clothing store has its advantages. I'm always able to sneak away the returned stock or the retired items. We're supposed to send them to carbon storage, but maybe sometimes not all of them are included in the shipment... No one checks." Creampuff took me on a tour, showing me some of her favorites. There were sissy party dresses, sissy baby dolls, pink terry cloth rompers, gauzy see through blouses, fancy bras covered with pink silk flowers, panties with rows and rows of ruffles, an elegant gown from the Christine collection, an even a tight rubber pencil skirt from the Andy collection. "I'm so jealous!" "Thanks." Creampuff smiled and then gave me hug and a kiss on the cheek. "Are you hungry?" Of course I was famished. Creampuff went to the back where there were a couple of kitchen chairs by a built-in desk. Under the desk was a mini fridge and a shelf above held a microwave oven. Creampuff fetched a pitcher of water from the fridge and we both drank. "Oh my god, I hadn't realized how thirsty I was," I said, gulping the water. "It's a well known fact that Sissies get very dehydrated inside Sissy Prayer Rooms," Creampuff explained. "I should have given you a drink while we were there." "No, no. I was happy to leave as quickly as possible!" Creampuff fetched two irradiated dinners in segmented plastic trays from another shelf and popped them in the microwave. * * * We sat at the desk chatted while we ate. Creampuff told me more about her job at the Sissy store. Because it was for clothing, it was one of the most desired Sissy jobs. "Do they have any openings?" I asked. Creampuff shook her head. "But I'm sure they're other jobs available. You can check in with the Sissy placement service down the block. People always want sissies." "Why's that?" Creampuff looked at me for a second, like I was absolutely clueless. "Because we're free," she said, as if it was the most obvious fact, along the lines of 'because the sky is blue.' "Corporations don't have to pay us wages. Or benefits. Why else do you think there's such pressure from the government to turn men into sissies? Companies want free labor." "But but," I gasped shocked. "Why do you work? If you're not getting paid?" "Well for one, it's more fun than sitting around here all day watching Sissy streaming on the heads-up," she shrugged. "But mostly because the more work credits I get, the faster I obtain seniority and eventually I can move up and get a better place with more room and better food. You should see the dorms downstairs! A room like this would hold eight to ten sissies downstairs, and all you get is 18 inches of hanger space, two drawers and those awful protein bars to eat." "Oh Creampuff," I reached out and grasped her hand. "I had no idea." "No one does," she shrugged. "I mean, the Sissy Council does their best, but they have no real power, you know? But it's okay. I chose to be a sissy. I knew what I was getting myself into." Creampuff kissed me on the cheek. "Some Sissies even prefer the dorms," she grinned, her eyes mischievous. "Trapped in a room full of Sissies? Panties and boobies and peenies and bottoms everywhere? Constantly rubbing together? Unable to escape?" I looked at her, eyes wide. Now *I* wanted to be in the sissy dorms! Creampuff laughed, seeing the look in my eyes. "I know what you need," she said. "Let's get a shower." Creampuff and I both stripped. "Oh, Creampuff!" I said, pointing to some red scars on her chest. "Oh, it's nothing," she shrugged. "A childhood heart defect. But I think it's why I've never been able to become a house Sissy. They see the scars and decide they want someone else." "I'm so sorry." "Don't be. I've got a wonderful job helping Sissies like you! I love my job. But you! You're young and adorable. Some real boobies and a bit of facial surgery and someone will snap you up in an instant!" "Oh, I don't know..." "Suit yourself," Creampuff shrugged. "But being a house Sissy is the best. A room of your own? Real food made from fresh ingredients? Actual 'net, not the limited Sissy 'net we're forced to watch? I mean, I like sissy porn as much as the next girl, but when that's all you're allowed to watch..." Creampuff gave me a shiny satin robe (gauzy mint green with marabou trim) and then got one for herself. She fetched some towels from off a hook. "So where's the bathroom?" I asked, looking around. "It's a public bathroom," Creampuff said, leading me into the hallway. "No!" I gasped, pulling away from her. "I can't go into a public bathroom!" I tried to retreat back into the apartment, but the door had already locked behind us. "Honey," Creampuff said reasonably, "there is no other choice. We aren't allowed private bathrooms at my level." "But... but..." I stammered, as she reluctantly dragged me down the hall. "But... I'll be naked! They'll all see me...!" "Better get used to it," Creampuff said. I had a feeling she was actually enjoying my discomfort. "Sissies have no privacy." * * * The bathroom was large and a buzz of activity with at least a dozen sissies of all shapes and sizes and ages in varying stages of undress. At first I just pulled my robe tight around me and stared at the floor, trying to be inconspicuous. I was used to male bathrooms, where everyone minds their own business. But Creampuff was having none of that! "Hey Gurls! I have a virgin newbie!" Creampuff called out. She slapped my hands away and stripped me, leaving me naked and shivering. Hanging our robes on a hook, she grasped my hand and pulled me into the showers. "What have we here?" I felt a soapy arm around my waist. It was an older Sissy with a warm expression. "I remember my first Sissy shower like it was yesterday," she sighed, giving me a kiss on the cheek. "It's okay, we won't bite." "Unless you want us too!" said another, with a 'rrrowl' in her voice. "Now girls," Creampuff said, "let's make our newbie feel welcome!" I felt hands on my back, soaping it up. "I call the bunsies!" someone said. Bunsies? I thought, but then went 'eep!' as I felt soapy fingers running between my ass cheeks. And just like that, I was surrounded by a half dozen naked sissies. They pulled me under the shower and I was quickly drenched. "I... I... I'm so e-e-embarrassed...!" I cried, closing my eyes in shame. "Oh, honey, why?" asked the older Sissy. She soaped up a wash cloth and was now washing my shoulders. "B-b-because," I stammered, under the water. I felt more hands on my body. Two Sissies were kneeling and were now soaping my feet and legs. "I'm so scrawny... and my hair is too short, and... and... I'm wearing breast forms!" "These?" the mature sissy said, grasping my breasts in her soapy hands and squeezing them and pinching the nipples. "These are wonderful! And don't worry about the rest of it. We were all just like you when we first became Sissies. Isn't that right, girls?" The entire group shouted their agreement, and I felt even more hands touch me. "And I know what you're really embarrassed about," whispered the older Sissy. "It's this, isn't it?" She grasped my peenie and squeezed it with her slippery fingers. I looked her in the eyes, shocked. "I knew it," she crowed. "Well, there's only one way to get over that! Girls!" she called out. "Our little one here is peenie shy!" No! I looked at her, horrified. NO!! I desperately looked over at Creampuff for help, but she was just grinning from ear to ear. The older sissy pulled my hands behind my back and turned me to face all of the other Sissies in the shower, my bobbing peenie (I was hard?? How could I possibly be hard??) for all to see. There was silence for a second as they all stared at my little member, six naked Sissies all with their own peenies (in various states of hardness) and breasts and long hair. "But it's adorable!" One finally said. "Why would you be shy about it?" And just like that, there were six sets of sissy hands on my peenie and num-nums, stroking them with their soapy fingers and all of them exclaiming how sweet and adorable my peenie was. But that wasn't enough, apparently. To fully 'cure' me of my shyness, all of the sissies pushed forward their own naked peenies and hugged me, all of our peenies together in one mass of naked peenie, all slipping and sliding against each other. A couple of the Sissies even had their spurties, right there, to the riotous (and a bit envious) laughter of the others. This continued for a while longer, all of us a mass of breasts and peenies and hands and fingers and soap, squirming Sissy flesh everywhere, until the shower temperature suddenly flashed colder. "Everyone out!" Creampuff shouted, and just like that, everyone rushed out of the showers pushing and pulling me with them. And we all stood dripping and laughing by the benches, everyone fetching their soft towels and drying off. "When the water temperature drops, it's a warning," Creampuff said. If you spend too much time in the showers they become ice cold, and believe me, you don't want to experience that!" As various Sissies finished drying themselves off, they came over to me in singles and pairs to give me kisses (sometimes right on the lips! With tongue!), hugs and gropes. "Welcome," they all said as a hand would drop down to squeeze my bottom or a leg would brush across my peenie, still hard and bobbing about. "So glad you've joined us." "Thank you, Mamma Marlene," Creampuff said to the older Sissy. "That was just the sort of welcome that Charlie needed." "Anything for my Creampuff," Mamma Marlene said, gathering Creampuff into her arms and giving her a long kiss with tongue. "Oh, Momma!" Creampuff sighed. "You still got it." "I should hope so!" * * * "Momma Marlene is the unofficial Sissy den-mother of the floor," Creampuff explained as we walked back to the apartment. "She looks after us as best she can. She can always be counted on to lend an ear, give us a hug, or provide just the right introduction to a blushing new Sissy. She's also the sissy council representative." "She's amazing." "Oh, I'm so glad you like her," Creampuff said, leading me into the apartment and closing the door. "So what did you think of your first Sissy shower?" Creampuff asked, pulling me into a hug. We were both just in robes, and so our breasts pressed against each other. She placed her hands on my bottom and pulled me close. I could feel her hard peenie through the silk robes. "It was wonderful," I sighed, blushing. "I thought you would like it," Creampuff grinned with satisfaction. "See? Being a Sissy is not all small rooms and having to bend over to sleazy Admins like Jacob. It's the sisterhood. That's the best part." "I'm beginning to understand that." I placed my head on Creampuff's shoulder, enjoying our closeness as she stroked my back. "Time for bed?" she suggested. "Yes," I agreed. It was late, and it had been an exhausting, stressful day. Creampuff looked up and I saw a hammock descend from the ceiling. "What's that?" "Our Sissy Sling," she said. "Sissy Sling?" "It's how Sissies sleep when we're together. Sometimes we just sleep on the floor, but this is so much more delicious." The hammock dropped all the way down to the ground where it rested on some cushions. Creampuff took off our robes, her soft fingers gently stroking my shoulders, hanging them on a nearby hook. After fetching something soft and green from a drawer, she had us both lay down on top of the Sissy Sling. It was made of a black, shiny, slippery and stretchy material. Creampuff and I lay in it side by side, both of us naked, her deliciously soft naked skin against mine. Creampuff showed me what she had fetched from the drawer. It looked like a soft terri-cloth sock with some soft fuzzy laces hanging from the bottom. "It's a double peenie sleeve," she explained. It was puffy and the inside was lined with soft nylon fabric, like a pair of silky panties. Creampuff pushed and pulled our bodies together until our peenies were side by side, hard and pointing up. Creampuff then held our peenies together (root to root and head to head) and slipped the soft terri-cloth sock down them both, holding them deliciously together, side-by-side, trapping them in an intimate embrace. She then took the fuzzy laces and looped them around our num-nums, tying them together. Now any time I moved, I would tug on her num-nums and any time she moved she would tug on mine. Also every little movement would cause our peenies to slip and slide against each other inside the sock. "Up we go!" Creampuff said, and the sling slowly rose up, enclosing us. As we were lifted up, the sling wrapped around us, our weight pulling us close, bodies and naked skin rubbing sensuously together, our peenies caressing each other in the soft peenie sleeve. "Come here," Creampuff said, her hands wrapped around my waist. The sling drew tight around us, pushing our heads together. Creampuff opened her mouth and I opened mine and just like that we were kissing, all tongues and lips, wrapped up in each other's bodies and unable to escape. We were two naked Sissies in a black silken tube, our naked bodies slipping against each other. I got lost in a haze of lips and noses and skin, as Creampuff squirmed against me. Inside the green sock, our peenies slipped back and forth against each other as we squirmed, our num-nums tugging and pulling. The air in the room cooled slightly, so even with our two bodies so close to each other in the Spandex sling, it felt just right. "Oh Charlie," Creampuff sighed. "I'm so glad you came home with me." We continued kissing with wet mouths and squirming, slowly building up our excitement. It was Creampuff who spurted first, her peenie twitching and pulsing with sissy cream inside the soft sock. I came just a minute later, our peenies and the socks now wet with our combined emissions. After that, we settled down into a slower more relaxed pace. The sling held us together so we couldn't separate. We became one Sissy, squirming together with pleasure. * * * I awoke with a start, feeling the sling descending. "Shhhh, it's okay," Creampuff whispered, stroking me. "It's just my roommate." "You're roommate?" I gasped, trying to pull away, but Creampuff held me tight and there was no place to go in the sling anyway. "We have a guest?" I heard another Sissy's voice behind me. "Oh, Creampuff, how wonderful!" As the sling settled on to the floor, I another sissy snuggle in behind me. "She has a jewel," Creampuff said. "No problem!" the new Sissy reached between my bunsies with two delicate fingers and extracted the jewel, putting it aside. Then I felt the same fingers back, but this time with lubricant. "Let's get you all nice and slippery," she whispered, her breath hot on my neck, her fingers slipping between my cheeks. "What?" I gasped. "Why?" I struggled to get up, but Creampuff just held me close, refusing to let me move or flail about. "There," said the Sissy, snuggling up behind me. The Sling started to rise again, but this time, there were three of us. "Oh!" I gasped, feeling a peenie probing my bottom. "Oh goodness!!" As the sling pulled higher, the three of us were wrapped up together, and the new sissy's peenie (it was well lubricated) slipped right into my bottom, and as then sling pulled tight around us, she was forced in deeper and deeper. "Ohmmmm..." I moaned. Her peenie was surprising long and hard for a Sissy! "Butterscotch? This is Charlie." Creampuff introduced us. "Charlie, this is my delicious roommate Butterscotch. As you can tell, there's one part of her which I especially enjoy." "Ohhh... goodness!" I groaned as Butterscotch started to slowly thrust her hard, slippery peenie in and out. "*Very* pleased to meet you, Charlie!" Butterscotch said, giving me a kiss on my cheek from behind. I was now sandwiched between two sissies, the sling holding our bodies tightly together forcing us to be best sissies. Creampuff's peenie had grown hard again (as had mine) and she was back to kissing me on the lips. Butterscotch, clearly a very horny Sissy girl, continued to thrust her peenie into my bottom, the sling swaying back and forth as we squirmed together. We were three wriggling, kissing, fucking, stroking, horny spurting sissies in a sling. We stayed like that all night long. My peenie in the sleeve with Creampuff's, our num-nums looped together. After Butterscotch had her first spurties in my bottom, she settled down and slipped out, but it wasn't long before she got hard again and thrust it back in. Eventually, Creampuff and Butterscotch fell asleep, both of them more used to the sling than I was. I felt their breasts on my body and their lips on my cheek and neck, their warm breath brushing over my face. Every now and then one of them would wriggle and sigh, making my peenie hard again. And I thought, this is heaven, sandwiched between two naked sissies, our soft bodies rubbing together and peenies doing delightful things. I eventually drifted off to sleep. * * * Chapter 21: Caught! "And what have we here?" The light-bar in the room was suddenly turned up to 'sunlight'. Creampuff, Butterscotch, and I shivered in the cold air, blinking in the bright light, our naked bodies still entwined, trying to figure out what the hell was going on. There was someone standing over us, a stern looking matronly woman. What the hell? Butterscotch rolled apart, her hard peenie slipping out of my bottom. "Supervisor Gabriellez?" Creampuff asked. Creampuff frantically reached down and untied our num-nums and pulled off the peenie sleeve. It was sopping wet, saturated with Sissy cream from the multiple spurties we had together during the night. Our peenies came out embarrassingly slick. There was a pungent smell of peenie cream. "Goodness, looks like our little nest of Sissies had quite a passionate night, didn't they?" "Wha--what are you doing here? In our apartment?" Butterscotch asked. "We haven't done anything wrong, have we??" You could hear the fear in her voice. "That, depends, darling Sissies. Did you know that you're harboring a runaway?" Butterscotch looked at me, surprised. Creampuff looked at me with an expression of, 'Well, I tried.' "I'm not a runaway," I said, my voice shaky. I felt a fear in the pit of my stomach. "I'm... I'm a grown adult man." Unfortunately, my voice broke on the word 'man,' and it came out of my mouth with a Sissy-sounding squeak. "Charley?" asked a second voice. She stepped forward. "CINDY??" I cried, immediately bursting into tears. "I-I-I-I'm s-s-s- sorry, I mean 'Ms. Pauline... I-I-I..." "Everyone, could I please have some time alone with my husband?" "Oh! Uh, sure, Ms. Pauline!" Creampuff hopped up and threw on a robe. "Butterscotch, uh, let's go get our showers. We, uh, have a lot to clean up. Take your time." Butterscotch pulled a handkerchief from a shelf and handed it to me and then grasped my hand for a moment. She seemed about to say something, but then she just snatched a robe and left with Creampuff. "You'll be safe here alone?" Supervisor Gabriellez asked. "We'll be fine," Cindy assured her. "Well, okay." The Supervisor looked back and forth between us. "Note me if there's a problem," she added, closing the door behind her. There was a long pause. I dried my tears and blew my nose in Butterscotch's cotton and lace ruffled Sissy handkerchief. "Why did you run away, Charles?" Cindy asked. It had been so long since I had heard 'Charles', I almost didn't recognize it as my name. "Cin-- Ms. Pauline," I started, then stopped. Why had I run away, exactly? "I don't really know," I said, finally. "I just... I just couldn't go home." "And now I find you in a Sissy sling, cocooned and writhing in a Sissy tangle all your own." "But, it's not like that!" I protested. "Oh really?" she looked at me with arched eyes. "Then what is it like? Tell me, Charles, what was it like last night?" I blushed and looked away, tears threatening to leak out again. "I just wanted to get away," I said, plaintively. "I-I-I... I didn't know what it was going to lead to." "Well, now that you've had your little Sissy fling, I think we can drop all of these silly pretenses, now can't we? Come, Charles, it's time you became a Legal Sissy. Get dressed, and I'll take you to the courthouse." "NO!" I shouted. "Mr. Charles Cynthia Pauline! I am your wife! You *will* obey me!" she shouted. "No! You can't make me!" "I can cut you off from everything. Turn you out onto the street. You'll have nothing! I'll mark your record forever! You'll never be able to work as a data processor again!" "You would do that?" I looked into her eyes. "Cindy?" I sobbed. "But... I thought... I thought... I-I-I-I..." Tears began leaking down my cheeks. "What did you think? CHARLES? What exactly did you think?" Cindy said, standing tall in her heels and looking down at me. "I thought you loved me!" I sobbed my heart out. "I thought we-we-we were soul mates. I... I... love you so much! I can't stand... can't stand..." "Can't stand what?" Cindy said, more softly this time, sitting on the floor with a hand on my shoulder. "I can't stand seeing you look at Ed that way!" I sobbed. "Shhhh.... shhh...." Cindy said. "There, there, Charlie. Go ahead and have a good Sissy cry. There you go. That's my darling sissy." "But... but..." I tried to get out. "It's okay. Everything's going to work out just fine." "But how can it?" I wailed. "How can it possible work out?" "Because," she said simply, "I love you too. Just as much... no, more... much more... than I ever did." "But..." "Look at me, Charlie." Cindy held my face between her hands. "What I have with Ed is just physical lust, do you understand? Just animal urges. We women, when it's that time of month, we get horny and we need a big hard cock to satisfy us. That's all it is." "Then you're not...?" "No, I am not in love with Ed. He is merely a convenience. A well- paid convenience, I might add," she rolled her eyes. "He is like a therapist, helping to drain my sex urges so I can concentrate on my work. Do you understand? I certainly don't love him!" "You don't? Are you sure?" "Yes, my darling Sissy. *You* are the one I love. *You* are one I will *always* love. *Forever*. *You* are the one I married. Yes, I realized soon after we were married that I would need some 'extracurricular help' for my biological urges. You know how women can be. But I didn't think you'd ever for once confuse that with love! And then, your boss, Ms. Jensdotter, showed me the psych-model the company had worked up for you. It said you were a latent Sissy. A Sissy In Denial. That all you needed was some positive feedback and some tough love and then you would become a contented Sissy for life." "They did a psych-model?" I gasped. "How did they get the data?" "You really should read your employment contract more carefully. You gave the company approved access to your entire digital profile." "Oh my god..." I stammered, thinking about what exactly that meant. "Yes, indeed. They had plenty of data. Anyway, they ran that through their models and lo-and-behold it said: Charles is a Sissy. So Miriam--" "Miriam?" "Oh, that's your boss's first name. Miriam. Anyway, she asked me what did I want to do? I told her I didn't know. So she suggested a test." "The test." "Yes, the first test. And we both know how that turned out, didn't we? And so then, with my approval, she started to push you into Sissyhood, and although it took longer than expected, well, here we are." I looked down at the ground, confused. "I disappointed you," I said. "I turned out to be... to be a Sissy." "Oh, Charlie, is that what you think? I'm not disappointed at all! To tell you the truth, I am relieved!" "Relieved?" "Yes! The idea of having a husband in this day and age? It's so... old-fashioned. I don't know why I ever let my grandmother talk me into it. When I heard that you might really be a sissy inside, well, to be honest, I was really hoping it would be true. Because then I would be free to be a woman, a truly modern woman, and not tied down to any of those antique notions about monogamous relationships. I could have men like Ed to satisfy my animal needs, and then I would have a Sissy at home to take care of me. A sissy for love." "A sissy for love?" I asked, feeling a ray of hope. "Yes, my darling Sissy. For love." "I love you, Ms. Pauline--" "Oh, that was Ed's idea. I don't really like it. Call me Cindy." "Are you sure?" I asked, my heart leaping for joy. "Yes, but only when we're alone together. In public you should call me Ms. Pauline." "Thank you, Cindy! Thank you! I love you, so much! With all my heart!" "And I love you too, Sissy Charlie. Now shall we make this forever?" * * * I went out to go find Creampuff and Butterscotch, only to find them listening at the door! Those naughty sissies! "I hope Charlie can come spend the night sometime," Creampuff said, giving my bottom a pinch. "She was supper yummy!" "The yummiest!" agreed Butterscotch. "Oh, I think that can be arranged," said Cindy, with a broad smile. "After all, it's only fair." Only fair? What does that mean? I wondered. "So, let's get her dressed and we can go downtown and turn our sissy into a Legal Sissy." "Oh no!" I cried. "My clothes are still at the Sissy store!" "Oh my gosh, that's right," Creampuff realized. "I didn't have enough room in my bag for them. Oh well! I guess you'll have to wear your new Sissy outfit!" "Wait... my... you can't possibly mean...?" But then Creampuff pulled out the lemon yellow dress I had worn the night before, the one with the ridiculous exposed bloomers and wide skirts which left nothing to the imagination. "I'd be too embarrassed to wear that - downtown? What about..." I indicated the entire wall of Sissy clothes. "Sissy Charlie!" Cindy broke in. "Where are your manners? We don't go around asking our guests if we can wear their clothes! If you have a perfectly workable outfit to wear, then let's get you dressed and be on our way. I'd like to get to the new Sissy Registration Bureau before the line gets too long." Creampuff gave me a look which was half sympathetic and half 'I told you so'. The two Sissies had brought warm, wet wash cloths with them from the showers, so they quickly wiped me down, cleaning up the emissions from last night which were leaking down my my legs and then scrubbed me down generally. I tried to help, but they just slapped my hands away and worked together quickly and efficiently until I was squeaky clean. "Sissy soft and smooth," Butterscotch said, as they finished applying moisturizer from head to toe. I smelled of lilac and rose oil. After re-inserting my jewel, I was quickly dressed in the complete yellow fantasy-sissy dress. This started with my bra (the new one for my DD breast forms) and sissy panties. Then the yellow-ribboned garters, white silk stockings, yellow ruffled socks and black high heels (with the buckle on the front). Then the bloomers and finally the party dress. In the mirror, I realized how ridiculous I looked, with the skirts only going down to my waist, and my hard peenie clearly tenting out the bloomers for all to see. I blushed a bright pink as Cindy smirked. Creampuff expertly did my makeup in sissy-baby-party style, with bright red lipstick and rosy cheeks, and then added the Goldilocks wig. "Oh, how adorable!" Cindy cried, as she saw me with the wig. "Like a little party girl! So wonderful!" Next came the satin opera gloves, then the cape and bonnet. And then finally the leash, which was attached to my Sissy collar, threaded through the high buttoned neckline of the cape and then handed to Cindy, my owner. "I can't thank you dears enough for taking care of my Charlie," Cindy said, as she air-kissed both Creampuff and Butterscotch on both cheeks. "Our pleasure!" Creampuff said. "Come back and visit!" * * * On our way out, we stopped by Supervisor Gabrielez's office. "All set?" she asked, eying me up and down. "Yes, all set," said Cindy. "And thank you so much for your help. I presume the compensation was sufficient?" "Yes, quite sufficient. Let me know if there's anything I can help you with in the future." "Actually, I was hoping you'd be able to reset her chip? It got zapped at the Sissy Store by the Admin there." "Oh, no problem!" Supervisor Gabrielez reached into a desk drawer and pulled out an exact replica of Jacob's zapper. She felt around my neck, through all of the layers of clothing, then flipped a switch on the zapper and pressed it to the chip in my neck. I braced for another electric jolt, but there was nothing! Suddenly, my heads-up snapped on! I was connected back to the 'net! "There," Supervisor Gabrielez said, checking the chip with the device which flashed green. "She should be ready to go." "Yes, her feed is back," Cindy said, checking her heads-up. "Thank you so much!" "But... but..." I stammered. I stumbled after Cindy as we left the building and crossed the sidewalk. "My chip was fried! How can it be back again?" "Oh, it has EMP-protection," Cindy said. "Didn't you know that? A circuit breaker. All you have to do is reset it." "Oh..." I said, frowning. "So now you can see..." "Yes, everything that happened last night," Cindy said. "A Sissy Prayer Room! Well goodness! But no time now. I'll review this later, with Ed. I'm sure he'll be interested to see this! But it certainly looks like Creampuff delivered on her end of the bargain." I stopped so suddenly that the leash came out of Cindy's hands. People walked past, staring at me and my sissy outfit as I stamped my foot in frustration. I felt exposed and humiliated. Tears leaked down my face, ruining my sissy mascara. "Creampuff..." my voice came out as a hurt wail. "She... she was in on it? You and Creampuff were working together the whole time??" "Yes," Cindy admitted. "As soon as you asked for her help, like a good Sissy, Creampuff called your owner to ask what to do.I told her that I thought you were having trouble accepting Sissyhood. So when Creampuff said she had a plan for turning you Sissy once and for all, I agreed." I stood there, shocked and upset. The whole thing had been a ruse. A plan to get me to accept being a legal Sissy. "Oh dear, here, let me help you..." Cindy pulled out a handkerchief and dabbed at my eyes, "your makeup is running." "So, I was never really free," I said. "No, dear. Creampuff was sending me regular reports every step of the way, and video and audio clips too." "And was Jacob in on it too?" "Oh, absolutely. His involvement cost me a pretty penny." I felt stripped bare. Exposed. Violated. But most off all, foolish and naive. A mere child in a world of adults. Unable to even run away for a minute without being caught and manipulated. "It was for your own good," Cindy explained. "I love you too much to let you wander around the city on your own. Creampuff and I both thought that once you had got this little rebellion out of your system, then you'd happily come back into the fold." I looked up at Cindy as she put an arm around my shoulder and dabbed at my eyes with a handkerchief. I felt defeated. Thwarted at every turn. Broken. Trapped. "Come," said Cindy, picking up the leash and leading me towards the waiting car-share. "Let's get you registered." "Yes, ma'am," I said meekly, all fight gone, now and forever. "Yes, Ms. Pauline." * * * Chapter 22: I become a Legal Sissy In the car on the way to the bureau, Cindy reached out to hold my hand. "I know you feel betrayed, Charlie, by Creampuff. And maybe by Jacob and Butterscotch too. But you shouldn't," she said. Her hand drifted down to my peenie, nestled in the bloomers. "They were only thinking of what was best for you," she continued, gently stroking me. "That's all any of us really want for you, Sissy Charlie, is what's best for you. Because you really are a Sissy deep down inside. You realize that now, don't you?" "Yes, ma'am," I said, looking down. "I realize that now. Thank you, Ma'am, for doing what's right for your Sissy Charlie." I felt numb, like all of my layers had been stripped away. 'Who am I?' I wondered. 'Who am I really?' Just then, my mothers words from my childhood came back to me. "It's not what's outside that's important. It's who you are the inside," she had said. Was I a man or a sissy? Who am I on the inside? But as the shock of betrayal began to fade, a core truth emerged. Something I could not deny. 'I really am a Sissy,' I realized. I looked over at Cindy, who was looking at me with concern, and smiled. "I know my place now, Ms. Pauline," I said. "I know who I really am." "That's my girl," Cindy replied, giving me a kiss on my cheek. "That's my darling, darling sissy girl." * * * During the ride, Cindy continued to stroke my peenie, getting me more and more excited and more and more ready to spurt, but keeping me right on the edge, stopping whenever my biometrics on her heads-up told her I was approaching the line of no return. And so, by the time we arrived at the "Sissy Registration Bureau", I was hot and bothered and desperately horny for relief. Unfortunately, there was already a line of Sissies and their owners outside the building on the sidewalk. We waited outside for the office to open, and then filed in and sat down to wait our turn. It was a room full of women and their sissies, and all of the women were strong, confident, beautiful, and 'in-charge'. "She's a pretty one," the owner in front of us said. "And look at her outfit! Oh, so adorable! I need to get one exactly like it for my Sissy Sammy." "Yes, it is so excessively sissy, isn't it?" responded Cindy, her fingers stroking across my peenie trapped in the slippery nylon bloomers, making me pant with need. "It was picked out by one of the Sissies working at our local Sissy Store. And my Sissy Charlie really loves it, don't you, Charlie?" "Oh yes, Ma'am," I said, nodding. "It's wonderful!" Which was true, of course. It was a wonderful Sissy outfit. It was also the most humiliating and embarrassing clothing I had ever worn. But if that weren't bad enough, my hard peenie tented out the front of the bloomers and making it obvious to everyone that I was one horny and excited little Sissy. I felt someone gently squeeze my hand. Looking over the wide collar of the cape and the bonnet, I saw it was Sissy Sammy. I smiled at her and squeezed her hand back. "Oh, look, our Sissies have become friends!" said the new owner. "We should do a play-date sometime!" "That would be lovely," said Cindy, as they exchanged contact information. Finally, it was our turn, and Cindy led me by the leash to the registration officer (also a woman). She opened a contract and slowly went through each term and condition, detailing every right that I would be giving up as a Legal Sissy. ? I, Charles Pauline, forever wave my right to ownership of property ? All of my possessions will be legally and irrevocably transferred to my my owner ? I, Charles Pauline, forever wave my right to compensation for work performed ? Sissies do not earn wages. They work for the simple pleasure of being a Sissy. ? All wages for work performed for third parties will be automatically transferred to my owner. ? I, Charles Pauline, forever wave my right to vote ? My right to vote will transfer to my owner, who will now vote on my behalf. ? I, Charles Pauline, forever wave my right to privacy ? All aspects of my life will now be open to inspection by my owner ? She alone will decide what of my data will be released to others ? I, Charles Pauline, forever wave my right to protest ? I must accept all the directions of my owner and the government immediately and without complaint ? I, Charles Pauline, forever wave my right to freedom of speech ? My owner or the government can limit my speech in any way they feel to be appropriate ? I, Charles Pauline, forever wave my right to freedom of assembly ? All meetings will need to be pre-approved by my owner ? I, Charles Pauline, forever wave my right to freedom of movement ? I will only be allowed to travel wherever and whenever my owner or the government allows me to travel. ? I, Charles Pauline, wave my right to self-determination ? My owner will determine my future in all respects. ? My owner can transfer some or all of her controls over me to any one else at any time, in part or in full, temporarily or permanently as she sees fit ? In situations where communications to my owner might be compromised, I will follow the directions of the oldest, mentally competent non-sissy adult present ? I, Charles Pauline, wave my right to a fair trial ? My owner will hold power of attorney over all my affairs. The authorization of this power of attorney is durable, permanent, and irrevocable. ? Disputes involving my owner will be resolved by arbitration. If necessary, a member of the Sissy council will speak on my behalf. As each item flashed up, I touched my wrist to the clause and then spoke the clause out-loud, looking at the camera. And then I would be required to say, "As allowed by the Supreme Court, Connecticut vs Masterson, I exercise my right to wave this right to my owner and the government in perpetuity." This was followed by Cindy, saying: "As allowed by Supreme Court, Connecticut vs Masterson, as owner, I accept this right in perpetuity." This was followed by the registration officer saying: "As a duly recognized representative of the State of Illinois, I witness and approve this transaction. Further, the State of Illinois recognizes its responsibilities for contingency and oversight for this new legal arrangement between Charles Pauline and Cynthia Pauline." For each item, I was given a throb by my jewel and a nipple reward by my breast forms. And of course Cindy continued to stroke my peenie. As we went through the process, I got closer and closer to spurties, squirming with need. ? I, Charles Pauline, wave my right to marriage ? Sissies are not allowed to marry. My marriage with Cynthia Pauline will be dissolved immediately upon becoming a Legal Sissy with Cynthia Pauline as my owner. I looked up at Cindy, heartbroken. Of course I knew that Sissies couldn't marry. Everyone knows that. But actually having it stated for me, and understanding that I would forever be her Sissy and I could never again be her husband... it was a hard pill to swallow. "It's okay," Cindy said, giving me a light kiss on the cheek. "You'll be my Sissy instead of my husband, that's all. It doesn't mean that I'll love you any less. Quite the opposite. I'll love you more now that you've found your proper place." "Really?" "Yes, absolutely," she said with such certainty that it made me realize what a wonderful, confident person she was. I did retain the "right to be free from repeated physical or mental abuse". The registration officer emphasized that repeated physical or mental abuse would not be tolerated by my owner or anyone. But then there were a long list of items that were considered to be 'standard Sissy maintenance' and 'not indicative of abuse'. This included spankings, canings, anal penetration, oral penetration, bondage, stocks, certain types of inflicted pain during sex play... the list went on and on, and each item had many different types and dimensions and carefully specified thresholds. It was practically a catalog of sadism, all designed to keep a Sissy in her place, under the thumb of the owner, but safe from permanent physical or mental injury. ? I, Charles Pauline, wave my right to my physical body and mental integrity, with the exceptions as stated, to my owner and the government." I touched my wrist to the sensor. Cindy kept me on edge with her evil fingers on my peenie. This had the dual effect of making it more difficult for me to concentrate, as well as simply making me anxious to complete the process. "Now I'm going to ask you a series of questions, to make sure that you understand the full extent of what you are agreeing to," said the registration officer. "Go ahead," said Cindy, as she stroked my peenie. The registration officer smiled at Cindy. The two were getting along great. "Charles Pauline, by signing this agreement, do you understand that you will have no bank account, no savings, and nothing at all which you can legally call your own, not even your clothes?" I looked over at Cindy and gulped. Then I looked back at the registration officer. "Yes, I understand and agree." "Charles Pauline, by signing this agreement, do you understand that you will be required to work, as a Sissy in Sissy-appropriate jobs, every day of your life for no pay and no hope of advancement?" Cindy continued to manipulate my peenie in the bloomers. But even with her distracting touch, I understood exactly what the registration officer was saying. Sissies were not even second class citizens. We were non-citizens. "Yes, I understand and agree." "Charles Pauline, by signing this agreement, do you understand that you will need to accept your place in life, as a Legal Sissy, and that you will have no right to lobby for changes on your behalf or on anyone's behalf without the express consent of your owner and/or the government? And further, do you understand that you will no longer be able to vote in any election and that your vote will forever be held by your owner to cast as she sees fit?" I could feel the steel doors of the trap starting to close. But by this time, I was resigned to my fate. "Yes, I understand and agree." "Charles Pauline, by signing this agreement, do you understand that you will be forever limited in what you read, what 'net you can browse, what flicks you can see, and what entertainment or news content that you are allowed to experience to only what your owner and/or the government allows for you, as a Legal Sissy?" As she explained this, I could feel my world contracting as well. Soon, I would only be able to experience the world as a Sissy - only seeing what a Sissy is allowed to see, only able to read what a Sissy is allowed to read - getting a thoroughly censored and cleansed view of the world. The Sissy's view. "Yes, I understand and agree." "Charles Pauline, by signing this agreement, do you understand that you will become, in the eyes of your owner, the government and society at large, a Legal Sissy? Do you understand that, in the eyes of the law, you will no longer be male or female, but an entirely new and distinct Sissy gender? Do you understand that you will become a distinct class of individual person and that standard protections available to men and women will no longer be available to you? Do you understand that, as a Sissy, you are at the mercy of your owner and what government protections are afforded to Sissies, which are distinct and apart from standard rights and protections afforded to men and women and full citizens of the United States of America?" How much longer was this going to continue? As Cindy continued to stroke my peenie, I began to wonder if I could hold out until the entire legal ceremony was complete. But I did understand the importance of what was happening. I knew that Sissies were an inferior class, and this extended to all sorts of legal rights, privileges and protections. Sissies must know their place, that's all that the registration officer was trying to make me understand before I signed my life away. "Yes, I understand and agree." "Charles Pauline, Do you further understand that rights and privileges accorded to men and women will *always* be held above the legally inferior rights and privileges of Sissies? And that as a Sissy you will be of an inferior class to all men and women? That you may be treated as an inferior by any man or woman?" I felt a shiver run through me. I began to understand fully what it really meant to be a Sissy, looking up at all men and women. "Yes, I understand and agree." "Charles Pauline, do you understand that, as a Legal Sissy, you will no longer be entitled to protection from harassment or discrimination? And that workplace or public harassment can include jokes, comments, embarrassing remarks, intrusive questions, touching, groping, contact for the purposes of administering punishments, and sexual contact of all kinds, as allowed by your owner? Do you further understand that you have no right to place any sorts of limits on these harassing behaviors and that, as a Legal Sissy, you must just accept them as is befitting of your new place within the social and legal framework of this country?" Sexual contact? Groping? Contact for administering punishment? I thought back to how I was treated on the looper. Would that now become routine? And there was nothing whatsoever I could do to do stop it? "Nipple reward," Cindy whispered into my ear, making me squirm. "I understand and agree," I said, finally. "Finally, do you understand that all men and women are now above you and can treat you as an inferior? And that they can take liberties with your person as long as these are allowed by your owner and government law? That you will, in essence, become a servant for all men and all women in the world, to the extent allowed by your owner? Do you understand that your primary place in life is now service? Service first to your owner, and then service to anyone she designates? And finally, service to all men and women?" I took a few deep breaths. I was now at the threshold. The threshold of giving my life to Cindy. To becoming a Legal Sissy. To becoming her owned property. "Yes, I understand and I agree." "Very good," the registration officer said, satisfied. "Now, since you have come to the registration office in person, we will waive the waiting period--" "Waive the waiting period??" I gasped, shocked. "Yes," Cindy said. "That's why we're here, because I want you as my legal Sissy right away. As soon as you e-sign the binding clause, you will be a Legal Sissy. *My* legal sissy." "But... what about the trial period? I... I'll still have a chance to... to... you know, get my rights back, once the trial period is over?" Cindy and the registration exchanged a look. "Yes," said the registration officer. "According to current, in-force law, you will have a single opportunity to opt-out of Legal Sissyhood on the one-year anniversary of the date you become a Legal Sissy." "Oh, okay..." I said, feeling relieved. "So, I can change my mind after a year?" The registration officer looked up at Cindy, who nodded back. "Yes, as I said before, according to current in-force law," she said. "Are you ready for the final binding clause?" I looked back and forth between Cindy and the registration officer. It had been a long journey, but I knew the truth. I knew what I had to do to keep Cindy in my life. "Yes," I said. "Very good. Now, when your owner tells you, please read out-loud the statement on your heads-up and touch your wrist to the sensor." Just then, I felt the jewel in my bottom thrum to life, pulsing with deep vibrating waves. At the same time the breast forms came to life, nibbling and licking on my nipples. And Cindy continued to masturbate my penis through the silky yellow bloomers, with long, toe-curling strokes. Cindy held out a hand, preventing me from signing. Why was she doing that? She waited about 30 seconds as I got closer and closer to orgasm, watching something on her heads-up, before finally saying: "Okay, now." "I, Charles Pauline, willingly waive all of my rights as discussed and give them up to my new owner, Ms. Cynthia Pauline. The Sissy Registration Office has clearly and explained all of the ramifications of my decision. Being of sound mind, I hereby [unh!] renounce my rights as a man and register myself willingly [oh!!], and eagerly... "That's my darling," Cindy whispered, speeding up her hand on my peenie. "... as a Legal Sissy," I finished. But then, another message flashed up! "Read it!" Cindy said, excited. I read the message. "And my Legal name from now on will be... 'Sweet Princess Cherry'." And just as I touched my wrist to the sensor and my heads-up notified me of my new status as a Legal Sissy, and just as I realized that I was now truly and completely trapped as a Legal Sissy [for at least a year]... Ms. Pauline brought me over the edge and I shot my spurties into my bloomers, having a sissy orgasm right there in the registration office, right in front of the registration officer. And then I burst into tears. * * * As we walked out of the building, Ms. Pauline... Cindy... Ms. Pauline... led me by the leash from my sissy outfit. 'How did this happen?' I wondered, astonished at how quickly it all unfolded. 'I'm now a Legal Sissy. In the eyes of the government, I am no longer a man. I am a Sissy.' The whole process with the registration officer had been long and exhausting. I was glad that they were so careful about explaining all of the rights that I would wave, but it felt like a forced march into Sissyhood. I really had no choice but to accept each humiliating condition at every step. 'It's only until the trial period is over,' I kept telling myself, over and over, using that as a slim ray of hope for a last line of escape. I was lead past all of the Sissies and the owners in the waiting room. Tears streamed down my face which caused my mascara and makeup to run, making my face a mess. But worse was the large wet spot on the front of my bloomers, completely on display for all to see. The flouncing skirts and tulle petticoats were so high that my bloomers were fully exposed. The spot which was now cold and clammy. Everyone could tell that I had just had my spurties during registration. It was so embarrassing! People were staring and owners were pointing and nudging each other. And my peenie was still hard! It was poking my bloomers forward, making an obvious little tent in front which bobbed merrily to and fro as I minced behind Ms. Pauline on my high heels. My face burned with shame as Ms. Pauline lead me from the building, across the busy sidewalk (more stares, more pointing) and into a waiting car. "Where are we going, Cin--" I halted. "I mean... Ma'am?" "No, no, no... Sissies are not to ask questions," my owner said, waiving a finger at me. "Sissies are only to speak when spoken to. They should be seen and not heard. But I understand, Sweet Princess Cherry." Here use of my new sissy name was like a blow to my ego. How many times a day would I be called "Sweet Princess Cherry" from now on? And what would that do to me? Would I start dreaming it? Would I forget that my name had ever been Charles? "You understand... Ma'am?" "Yes! After all you've only been a Sissy for, what, oh just 7 minutes! Of course you have a lot to learn. And I am here to help." My owner pulled out a spurties towel from her purse, unfolded it and placed it on her lap. "Now, take down your bloomers and lay over my lap for a spanking!" Now? I looked at her, shocked. Right here in the car-share? But Cindy just looked back at me, her eye arched, and then nodded down to her lap. I knelt on the seat, pulled down my bloomers and then lay myself over her lap, careful to keep my wet peenie on her towel. She pulled up my panties so they wedged themselves up into my bottom, exposing my bunnies. Then she reached into her leather 'sissy care bag' and pulled out a hefty-looking spanking ruler. And then with gleeful 'oh, how wonderful!' my owner proceeded to spank my bottom. And hard! Soon I was 'yip'ing and 'yelp'ing! My owner even had to hold my hands to the small of my back because they kept getting in the way. Soon my bottom was fiery red and I was crying my heart out. And if that weren't bad enough, the car pulled up at its destination and the door automatically opened exposing my bare red bottom to the street. People walked by and stared and pointed. A couple even stopped to watch as My owner continued her enthusiastic spanking and I uselessly kicked my feet and cried. As if the embarrassment of being spanked wasn't enough all by itself! "You Sissies," Ms. Pauline said, finally stopping. "So soft and sensitive." She was breathing hard, but had clearly enjoyed herself. She reached into her sissy-care-bag again and pulled out some lotion which she spread on my bottom. The lotion soothed my bunnies and I squirmed some as she felt up my bottom (and the in-between) with her slick fingers. "Now let's go. I am in need of your services," she said, a husky tone in her voice. I crawled out of the car after her and stood unsteadily on my legs. "Leave them," Ms. Pauline said, as I reached down to pull up my bloomers. LEAVE THEM? A whimper escaped from my lips, which only served to make my owner smile. She pulled on the leash, and I was forced to follow her, taking small steps as the bloomers at my knees limited my motion, really mincing now in my high heels as we clacked-clacked across the sidewalk, my peenie bouncing now in full view, my breasts swaying, as we crossed the sidewalk and stepped into the hotel lobby. "Ms. Pauline," said the receptionist, a man, who smirked at me. This was a fancy hotel which still had actual human staff at the front desk. "You room is ready. I'll escort you up." I was forced to walk through the lobby, crowded with some sort of business convention, through business people (almost all women) in business suits, as they all stared at me, a sissy in a ridiculous fantasy-Sissy costume with cape and bonnet and little-girl's party dress in lemon yellow with skirts and ruffled petticoats at my hips, my bloomers now bunched up around my knees, my peenie in the sleeve of the panties with the exposed head and the wet tip bouncing around (still hard!) for all to see, and my panties pulled up in back, rubbing uncomfortably between my bottom cheeks, exposing my bottom with the bright-red spanks. The complete picture of a shamed, well-spanked, submissive Sissy being led on a leash by her owner. Finally we made it to the elevator, which we entered with another group of business people. In the elevator I heard them giggle and point at me. Oh no! I felt someone put a hand on my bottom! I turn to see who it was, but my owner pulled harshly on the leash. "Sweet Princess Cherry!" she said in a loud voice for everyone in the elevator to hear. "Stand still and don't fidget!" Soon, there were multiple hands, from multiple different people, squeezing my red bottom, making me squirm as I tried desperately to be still and not squirm. Tears squeezed out of my eyes and dripped down onto my breasts, both from the pain in my bottom and the horrible humiliation of it all. Finally, the doors opened, the hands disappeared, and we walked down the corridor to our room. * * * Finally, we were alone. Ms. Pauline looked down on me, regal and imperious. She wants something! I realized, suddenly panicking. What would she want?? "How may I serve you, Ma'am?" I asked, giving her my best Sissy curtesy that Helpful Hailey had taught me. "Very good, Sweet Princess Cherry," said my owner, as she held my head in her hands and kissed me on the forehead. "I know this is difficult for you, but I've been told it's important to make sure that brand-new Sissies really learn and understand their place as quickly as possible. But now, I am desperate for some relief. Prepare the bed for sex - and by that I mean just remove the comforter and plump up the pillows for me - and then prepare me for oral, by which I mean just remove my skirt and panties." I rushed to comply. As I removed Ms. Pauline's panties, I noticed how wet they were. Practically soaked! Was she as excited by my new position in life as I was? The thought gave me hope that maybe she really did want me. Ms. Pauline lay back on the bed and spread her legs. "I need you," she pointed. "Now." I had never been so happy to comply with an order from My Owner. I nestled between her legs and began to lap at her pussy like a good little Sissy. "Yes," she said, reaching down and tousling my hair. "This is where you belong, isn't it, Sweet Princess Cherry?" "Mmm-hmm," I agreed, doing my best to focus on her pleasure. "This is your place in life, isn't it?" "Mmm-hmm". "Good. Because this is where I need your services the most. Because, Sweet Princess Cherry, I am a hot, red-blooded, American, professional woman and I deserve this! I work hard and I have heavy responsibilities and I deserve to have my needs taken care of by an adoring Sissy! Because -- *unh* -- it is -- *oh yeah* -- it is -- *YES, THERE* -- BECAUSE IT IS MY RIGHT AS A WOMAN! MY RIGHT AS YOUR LADY AND OWNER!" Ms. Pauline screamed at the top of her lungs as she came, harder than I had ever seen her orgasm before, even harder than she had with Ed. And I did my best to hang on, kissing and licking her as she bucked and trembled and jerked under my adoring lips. * * * Chapter 23: Election Day "Excellent work, as always, Sweet Princess Cherry," said Ms. Jensdotter, looking over my results. "Thank you, Ma'am," I said, curtseying. I was dressed in my new Sissy Office outfit. It consisted a flouncy navy skirt, lacy crinoline petticoats that peeked out from under the hem, a tight, low-cut shiny satin blouse which showed my breast forms, a pink scarf (since all Sissies must wear pink) with pink lipstick and (only slightly) toned-down office makeup. The office outfit was from the Christeen collection. I'm still wearing breast forms for now. Unfortunately, I can't get real breasts until my probationary period is over. I am using hair-growth formula, but it's going to take a while before it really kicks in. It's a new CRISPR formula which actually rewrites your DNA for hair growth, so once it starts up, I'll have long golden hair forever. But in the mean time, I have to wear curly blonde hair extensions from the Sissy Salon. Ms. Pauline opted for tight sissy curls, which frame my face in child-like ringlets. To be even more Sissy, I've added some light blue and pink bows to my hair. I am still working as a data processor, which is a surprise. I thought I would be asked to be a full-time, at-home Sissy. "Why would I want that?" asked Ms. Pauline, my owner. "Leave you at home all day to get into some sissy trouble or other? Heavens no! Much better to have you earning a paycheck to help fatten my bank accounts! Or are you saying that you'd rather have some other job? Perhaps as a fluffer in a Sissy Prayer Room?" "No Ma'am! Of course not! I like being a data processor!" I shuddered with the memory of what Jacob had done to me. "Of course you wouldn't want to be *just* a fluffer, would you? After all, why be the appetizer when you could be the main course? Why, I bet you'd fetch a pretty penny with your oral and anal skills. And your enthusiasm, of course." My owner grinned a wolfish smile. "Maybe you should take a second job, hmmm... to earn me even more income?" "No, please, Ma'am," I said, back-pedaling and trying to think quickly. "Because, um, then I wouldn't have enough time in the day to take care of your house, your laundry, and to cook for you every night. And I know how much you like my personal service. And it does take ever so much extra time when Ed comes over, which he is doing almost every night now." "That *is* true," said Ms. Pauline, thinking it over. "Oh, Sweet Princess Cherry, I guess you're right. Well then, I guess it's just the boring old data processing job for you then." "Thank you, Ma'am," I said, relieved. As it turned out, having me as a Sissy was financially ideal for both the company and for my owner. Taxes for a Legal Sissy are zero, since we are legally unable to earn wages. All the money just goes directly into Cindy's bank account. So my company reduced my wages accordingly, canceled all of my benefits and just writes a check to Cindy every month. This is because I'm still technically the property of Ms. Pauline, who has sold my services as data processor to the CICI corporation. I found out later that it had all been arranged by Ms. Jensdotter, in collaboration with Ms. Pauline, almost from the first day I started work. Ms. Jensdotter, reached into her desk drawer and pulled out a paddle and a spurties towel. "Does Sweet Princess Cherry want a reward for her good work?" she asked. "Yes, please!" I squirmed with pleasure. I assumed my position, bent over, skirts up and panties down, my hands braced against Ms. Jensdotter's desk. The cold air conditioning on my bare bunny cheeks gave me shivers. After playing with my bunnies, stroking the bare skin with her fingers, Ms. Jensdotter proceeded to apply a series of firm, confident spanks to my bottom. It was clearly a "reward spanking", not nearly as hard or repetitive as a true punishment spanking. I squirmed with pleasure under her firm strokes, and after the first ten, she slipped the towel over my peenie and stroked me to spurties, which I did with a series of high Sissy squeals and delicate gasps. "Thank you, Ma'am," I said, with a curtesy, my naked peenie still exposed since Ms. Jensdotter hadn't yet told me I was allowed to cover up. "Is there anything else you require?" "Yes," she said with a husky voice, pulling off her panties and sitting in her desk chair, her legs spread. She certainly didn't need to tell me what to do! I pulled out my Sissy kneeling pad, to protect my soft Sissy knees, and then nuzzled my lips into her hot wet crotch. Ms. Jensdotter clearly enjoys spanking me, she does it almost every day, and every time when she's done, she's wetter than the floor of the sissy showers. "Backdoor," she said urgently, pushing me aside and bending over her desk, presenting her ass. I moved the kneeling pad, gently spread her cheeks and applied my tongue directly to her crinkled anus which winked and clenched in pleasure. Her taste was bitter and musky, but I'd gotten used to it. To be honest, it made my peenie stiffen. It's the taste of submission. Ms. Jensdotter reached a hand between her legs and quickly finished herself off, screaming a few "OH YES!"s, completely unconcerned about who might hear. I was no longer a minority in the office. Nearly two thirds of the workers had been converted to Legal Sissies. The transformation was astonishing. Talking to Jamie it was clear that the wives of the workers must have gotten together and decided to convert us, en-mass. Jamie and I were just the first test cases. And so we ended up as a mostly Sissy work-force. If you visited our office, you'd see a field of obedient Sissy data processors, all of us in our dark blue and pink office uniforms, all of us with curls and lipstick, fixing our makeup and the seams on our stockings, working on our tablets processing data with Sissy efficiency. With all the sissies in the building, the milking parlor got very busy. It was full of Sissies whenever I showed up for my milking sessions (reduced now to one a day). Sometimes I even had to share a dressing table. Often there was no place to sit in the waiting room. Many times we were milked in groups of two, three or four, sometimes milking or sucking each other in chains. Finally, Ms. Jensdotter was done. I fetched a warm wash cloth from her en-suite bathroom and helped to clean her up. "Today's Election Day," she pointed out. "Have you voted?" I looked down, ashamed. "Sissies don't have the right to vote," I said. But of course Ms. Jensdotter knew this very well. I think she asked just because she wanted to embarrass me. "Oh, that's right," she said, feigning forgetfulness. "Your owner, Ms. Pauline, now controls your vote, isn't that right? Do you know how she voted?" "I'm sure she voted for The New Woman's Party." "Wonderful." Ms. Jensdotter pulled up her panties and went back to sit at her desk. I stood there, awkwardly. I was clearly not dismissed. Ms. Jensdotter did something to her screen. "So, you're two months into your trial period, is that right?" she asked. "Yes, Ma'am." "So, how many days until it's over?" "Two hundred, ninety four days, ten hours and just over twelve minutes," I said, automatically. "Are you going to go back to being a man when it's over?" "I... I don't know." "Harrumph," Ms. Jensdotter snorted. "Well, soon it won't matter." "Wha... what do you mean by that? Uh, Ma'am?" I asked, shocked. Ms. Jensdotter paused for a long time, before looking up with an evil grin. "Bend over," she said, patting the top of the desk. "Y-Yes... Ma'am." I did as instructed, laying my head on my arms, feeling the rich hardwood inlay of her desk. I heard Ms. Jensdotter fetch something from her desk drawer, and then after a second, she moved behind me, pushed down my panties and removed my jewel. "Oh!" I squealed, as the cold tip of a lubricated rubber cock touched my anus. She was using her strap-on, obviously, something she only did very rarely 'as a very special treat'. Soon, Ms. Jensdotter was thrusting deep into my bottom, and I was feeling well and truly fucked by her hard rubber cock. "Since today is Election Day," she said, "I think it's safe to finally tell you who our customer is. I know we go to great lengths to anonymize our data, but I bet you have some idea of what it represents, don't you, Sweet Princess Cherry? You're too good of a data processor not to have figured it out. Tell me, what do you think our data represents?" "Population demographics?" I gasped, grunting as she choose that time to thrust in particularly deep. "Correct! And what about the rows?" "UNH!" I gasped. Wow she was really fucking me hard. "People. Or customers. Individuals of some sort. With... UNH... locations. Administrative districts. Latitude Longitude. Congressional districts, In the United States." Ms. Jensdotter pushed all the way in, so deep it made my toes curl, and then she lay on top of me and spoke directly into my ear. "That's exactly right," she said, her hot breath on my neck, as her weight pressed me into the desk. "You are such a smart data processor. Really, the best I've ever had. Better than the machines, which is astonishing. A true data processor and machine learning savant." She pulled back out, added some more lubricant, and then continued with her slow, long rhythmic strokes. "Our customer is, in fact, The New Woman's Party. Isn't that interesting? Our company, with your help, has been working diligently to get as many New Woman's Party representatives elected throughout the country as possible. It has been an Athenian task, because not only do we want two-thirds control of both houses of Congress, *and* the presidency, but we also want control of over three quarters of all state legislatures. Now, my very smart Sweet Princess Cherry, why would we want that?" Ms. Jensdotter pulled out and then held perfectly still, with just the head of the rubber cock lodged in my bottom. "B-b-because," I stammered, trying to wrap my head around the enormity of the scheme. "Because you want to be able to amend the constitution?" "Correct!" She said thrusting all the way in one deep slippery thrust, making me squeal out loud. "The one blatant flaw in the United States Constitution, is that any party that gets two thirds of both houses of congress and three quarters of all of the state legislatures can remake the United States in any way they want!" "Oh my god!" I shouted, half from her vigorous thrusting and half in horror of what she was saying. "Oh my god!" "That's it, pray to your Sissy god!" she said. "Because we're going to start by writing Legal Sissyhood directly into the constitution! That way it can't be un-done by future laws. Sissy rights will be permanently taken away. Even better, the courts will be able to force men to become Legal Sissies without their consent if they exhibit Sissy tendencies. Won't that be wonderful?" Oh my god! This couldn't be happening! "Oh, but we're not stopping there! Men will no longer be allowed to vote or hold public office of any sort. Husbands will become property and dependents of their wives, who will have sole ownership of the estate. It will be a permanent and lasting shift in power. Inheritance will fall to the oldest female relation. Female- preference primogeniture. Imagine all those daughters now in line to inherit their parent's entire estate! All hail the rise of the Matriarchy of these United States! Land of the free and home of the brave, as long as you're a woman!" "Stop! Please, stop! This is not possible!" "And we're cancelling the trial period," she whispered into my ear. "Which means, once a Sissy, always a Sissy, my Sweet Princess Cherry. Oh yes, that's going to be the very first law we pass. Which means you're stuck. Stuck as Sweet Princess Cherry... for life, my dear." "No! Oh god, no!" Ms. Jensdotter pushed all the way in, pushing me hard into her desk. "And it's all thanks to you, my little princess," she whispered into my ear. "Your data processing made it possible. It was your brilliance which showed us the way. How we could convert ten million men into Sissies, oh yes, you're part of that too, and tilt the scales just enough to take it all. You, my dear, are the hidden, unsung hero of the new, female ascendency, the Sissy who made history possible. Someday you'll have your own Wikipedia page. They will make movies about what you did. It's all thanks to you!" "NOOO!!!" I screamed, and with a huge effort I pushed Ms. Jensdotter away, her cock slipping out of me as she staggered and fell backwards onto the carpet. I pulled up my panties and ran out of the office, screaming. "YOU'RE TOO LATE!" Ms. Jensdotter called after me. "THERE'S NOTHING YOU CAN DO!" I ran down the stairs (not wanting to wait for the elevator) and onto the street. Frantically, I punched up the closest polling station. Running up to the station, I started screaming. "DON'T VOTE FOR THE NEW WOMEN'S PARTY!" I shouted. "THEY'RE GOING TO REWRITE THE CONSTITUTION! THEY'RE GOING TO MAKE MEN A PERMANENT UNDERCLASS!" I ran up to the line waiting to vote, which was, I saw my heart sank, about 75% female. "Please, you must listen to me!" I said to the people first in line! "My boss just told me! It's all a plot! They're going to have control of three quarters of the state legislatures! They can change the constitution to be anything they want! No one should have that much power!!!!" But everyone I talked to, just turned away. And why not? Here I was, a crazy Sissy, spouting crazy conspiracy theories! "I hope they do!" one stern looking woman said. "Men have been in control for thousands of years. It's time women got to be on top for once!" This was greeted with cheers by the other women in line. "New Women's Party!" They started chanting, over and over. "New Women! New Women!" This was followed by "Women Rule! Men Drool! Women Rule! Men Drool!" "NOO!!!" I screamed. "NOOO!!!" "Sweet Princess Cherry?" I heard a soft, feminine voice behind me. "Jamie?" I asked, shocked. "What are you doing here?" "Ms. Marysdau explained everything to me." "Then help me!" I begged. "Talk to them!" "Sweet Princess Cherry," Jamie reached out and grasped my hand. "It's too late. It's Election Day. There is nothing we can do to make a difference." "No... It can't be too late! Jamie... this is all my fault! It was my analysis which made this possible!" "You didn't know," she said. "The data was anonymized. It's not your fault." "But... but it is... I should have known. I should have... I should... Oh, Jamie!" I sank to the ground and burst into tears, clutching at Jamie, my head buried in her shoulder. Ragged, choking, heart-wrenching sobs. "It's okay, it's okay, Sweet Princess Cherry," Jamie soothed, stroking my back. "Shhh... it's okay." "No, it's not okay," I cried. "It's not. What have I done? Oh, Jamie." "Shhh... I understand... shhh..." she said. Jamie fetched out a lace handkerchief from a pocket and wiped away my tears. Then she tilted my head up and kissed me on the lips. "There," she said, as I smiled a sad smile. "That's the Sweet Princess I know and love." She kissed me again and we stayed like that for a while as streams of women and a few men got in line to vote. Finally, Jamie helped me up and we hugged. "Ms. Jensdotter has authorized me to take you to the Sissy Store to buy you a nice new Sissy dress. Won't that be nice?" Jamie said. "Yes," I sniffled, allowing myself to be led away from the polling station. "Thank you, Jamie." "We sissies have to take care of each other Sweet Princess Cherry," she said, hooking our arms together. "We're stuck now," I said, looking at Jamie with sudden realization. "Stuck forever, Jamie." "Yes we are." "Sissies forever." "Ooh! Creampuff says the store is having a Sissy sleepover tonight! Should we ask our wives if we can join them? I bet they'll let us!" "That sounds wonderful, Jamie." "I'm so glad we're sissies together, Sweet Princess Cherry. I love you." "I love you too, Jamie." THE END Thanks to Jamie Simms (no relation to the character in the story) and Ms. Sissy P for their editorial help. All errors which remain are solely the fault of the author.