Forever Her Sissy - Chapter 6 free porn video

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. I Absolutely love reading the reviews that you wonderful readers have been leaving, please, please, please continue to write and post them. You are the inspiration that makes writing so much fun! Forever Her Sissy - Chapter 6 I awoke to an insane buzzing noise, shit it was my alarm. It could not already be Monday morning. After Karen and I had returned home she had set me to work cleaning house, doing laundry, and then had me pleasure her before taking a shower and going to sleep. How could it be five in the morning. Quickly I shut off the despicable buzzer to keep it from waking up my wife. Slithering out of bed to ensure I did not disturb her I tip toed out of the bedroom. Deciding it was best to leave on the night clothes that Mrs. Karen had put me in before bed I began to get the coffee ready while still wearing a short pink camisole, matching pink panties, pink four strap garters, and sheer pink hose. I wasn’t sure I would ever get use to the hose and garters, the feeling of them laying against my skin in such and intimate way was unlike any article of clothing I had ever worn. It kept me in a state of constant erotic stimulation. With the coffee ground, the water in the kettle ready to heat, and the filter in the Chemex pour over I could shift my focus to getting Mrs. Karen's clothes ready for work. As always she had laid out her outfit. Today it was a grey wrap skirt and a dark red blouse with a jewel neckline. I loved her in both, the skirt was snug and stopped above her knees leaving her sexy legs exposed with a slit where the skirts wrap met. I imagined that she would be wearing dark hose with this outfit. My mind drifted to a picture of her dressed in the pretty clothes with black high heel pumps, and a no nonsense black Kelly bag or maybe a black Coach Messenger bag. ‘Oh no!’ I thought, I need to be ready to change out her purse for her, the colorful Dooney would not look right with such a professional skirt and blouse. I was making a quick mental note to do that as soon as she awoke and I could get permission to switch out her bags. Soon I was absorbed in my morning ritual of getting her clothes ready for the day. I started by taking a lint roller over her skirt, then giving it a nice press with the iron. Her blouse was very delicate and I was extremely careful while ironing it. The bodice had pleats which I meticulously ironed around. I was so absorbed in my work, humming a nameless tune to myself, that I did not hear Mrs. Karen come up behind me. "Good morning sissy, you seem happy this morning," she said in a sleepy voice. I almost jumped out of my skin from the surprise! Karen put her hand up to her mouth to hide a giggle. "I’m sorry honey, I didn’t mean to frighten you. You were just so cute in your pretty lingerie, humming your pretty little tune while working so diligently on the ironing," she followed up with a lovely good morning kiss. "I hope I didn’t wake you Mrs. Karen, you are up a little early this morning," I replied while glancing at the clock and noting that it was only quarter till six, she usually woke up around seven or so. "No sweetie, you didn’t wake me, I wanted to get up early this morning to help my sissy get ready for her first day dressing pretty for her new boss. This is very important so I wanted to be here to support you. I took off a few hours this morning so I could help you and even drive you to work." "Oh, thank you ma’am but I will be okay," I said trying to sound brave. "I’m sure that you will be fine honey, but I can also picture my little sissy getting cold feet and missing her first day at her new position. We don’t want to disappoint your new boss now do we? Just to make sure that you get there on time and properly attired I am going to walk you all the way through the door. Besides, I can’t imagine how humiliating it is going to be for you on the very first day of this important new job, with a demanding female boss and such pretty co-workers for you to show up dressed all girly! Mmmmm, little sissy, this is going to be so embarrassing for you," Karen was telling me, whispering it in my ear, her breath hot against the side of my face. Glancing down I saw that she was rubbing herself while she was talking to me. "Yes ma’am, thank you," I replied quietly. If I was going to be honest with myself she was right, I could have easily gotten spooked and missed work. I was so afraid of showing up at the office as a sissy. This was work, showing up in women’s clothes would mean that my sissyness would be exposed to the whole world, there would be no putting this cat back in the bag. "Mrs. Karen, I’m scared. All of the ladies at the office are going to laugh at me and make fun of me," I told her, my hands beginning to shake a little. "Honey, you are right to be scared. This is going to be horrific for you," Karen replied while continuing to rub herself through her panties. "Brie, Kneel down in front of me now, I want you to watch me." Following her command I lowered myself to my knees with my face inches from her temple. The smell of her sex was overwhelming and the dark spot from her dampness was growing as her fingers rubbed slowly, grinding the light purple panties into her folds. "Sissy, you have no idea. I spoke with Penny yesterday while you were busy twittering around with your chores. She is a remarkable woman and we are becoming good friends. Lucky for you she has more courage than I do, I think you will find she will be more creative and far more strict that I am," As she spoke I watched her fingers begin to speed up, turning in a circular motion, grinding harder into her folds. "Mmmmmmm, goooooddddddd!" Karen began to shudder, her hips bucking back and forth. "I have given her full permission to do anything with you sheeeeeeeee, oooooohhhhhoooo! Anything she sees fit!" With those last words I watched as fluid began to squirt out, soaking her panties. "Mrs. Karen ma’am! May I please use my mouth to clean you?" I cried out. "No, stay quiet and watch Brie!" she corrected me sharply. With her rebuke fresh on my mind I focused all of my attention on her as she lowered her panties, reaching over she lifted up a huge, tan flesh colored cock with a thick veined shaft and even realistic looking balls. This dildo was at least nine inches long and its girth was enormous. "Open your mouth Brie," she commanded, immediately I complied. With a dreamy smile she held the bulbous head of the cock in front of me. "Lick the head slut!" she demanded, placing the tip into my mouth before I could react or turn away. Instinctively obeying her I began to lick the head, moving my tongue across the slit at the tip and around the gland. Pulling it away from my mouth she pointed the huge missile into her folds and began slowly working it in. I was watching, in near disbelief as she opened to take the massive size, stretching to accommodate the thickness, the bulging veins rubbing against her lips as she began to slowly pump it in and out of her. Mesmerized I stared at her, watching her folds engulf the monstrous cock until she pushed it in so far that the balls touched her. Pushing it in and out with greater urgency she began to moan and then yell at me. "Look at this cock sissy! See how it is filling me, ummmmmmmmmm, see how he is fucking me, making me oooohhhoohhhh, making me cum!" she was pumping the dildo harder and faster, pushing it deep in herself. "Ohhhhhmmmmm, sissy he is so much bigger than you and ummmmmmmm, he won’t fall short and squirt ten-seconds into our love making. Look at him sissy! Aren’t you ashamed of yourself, your woman, your wife having to find another cock to satisfy her?" I could not turn my attention from her. I could see that her hands were trembling now and her movements were becoming jerky. With a final thrust she drove him deeply in her and did not withdraw, instead she twitched it from side to side. Karen was moaning, a sound that was deep and drawn out, her body was shaking and I saw tears at her eyes, her head thrown back, mouth gaped open. Her legs begin to buckle as her body started collapsing. Jumping up and wrapping my arms around her, slowing her decent we sank slowly to our knees together. With a ragged breath she slid the monstrous dildo out of her, as the head slid free she let out a quiet sigh. "Mrs. Karen, are you okay? Can I help you?" I asked, concerned that she had hurt herself while in the grasp of her passion. With a drunk sounding giggle Karen pushed off on my shoulders, getting back to her feet. "No sissy, you are much too small and locked up tight. I don’t think you are the right ‘man’ for the job." Looking down at the floor, so hurt by her comment because I knew it was the truth. "Mrs. Karen ma’am?" I asked in a pleading voice. "I’m sorry that I am so worthless and can’t do these things for you." My heart was being ripped out of my chest, this hurt so much. I knew that sexually I hadn’t been able to satisfy my wife but this made it so real. Never had I seen such an orgasm from her before, why would she want to stay with someone like me who could never hope to please her. Karen must have know my thoughts because she was standing over me. "Sissy, does it make you sad, what just happened?" she asked me, standing over me, naked from her waist down, her temple glistening with juices from her recent orgasm. Looking away, unable to meet the intensity of her gaze, unable to even look at her folds because I knew I was unworthy of that honor, I found my eyes staring at her pretty toes. Today they had a soft silver polish. Her voice broke through my rambling thoughts, "Sissy, I asked you a question?" This time her words did not sound as harsh, there was a softer tone. Bending down to one knee Karen forced me to look up. "Are you sad about what just happened?" "Yes ma’am, it hurts me so bad," I told her, shifting my eyes down in shame. "Sissy, why would you be sad about something that felt so good to your mistress?" she asked in a soft voice. I was confused, Karen had asked me if what happened made me sad and it had because I was unable to please her like that but now she clarified her question, why would I be sad about her having such a wonderful orgasm. I was trying to think but she was so much smarter than me, I didn’t want to disappoint her again. "Mrs. Karen, No ma’am I am not sad that you had such a wonderful orgasm, you deserve all the pleasure in the world. I am sad that I am unable to do that for you, give you such an incredible feeling ma’am," I whispered. Wrapping her arms around my shoulders she gave me a tight squeeze. "You are such a smart little sissy, I am so proud of you for understanding what I was asking you but you are not totally correct." I looked up at her with questioning eyes but remained silent in hopes she would explain it all to me. My mind was just not working right lately and I needed her help. "You do give me pleasure like that honey, with your love, your kindness, and that wicked little tongue of yours. It is just as incredible but different. You are so soft and so timid, a gentle love that last forever. What happened earlier was harsh, abrupt, but so powerful. Many women understand that type of pleasure, the feeling of a massive cock driving into them, filling them, fulfilling our lustful desires. In contrast very few women will ever get to experience the love that we have, the love you give me. It is the most beautiful love in the world, partially because you have willingly given up everything to me, complete and total devotion, but not out of fear or force but because you love me that much. Do you have any idea how special that makes you to me. That is why I constantly tell you how much I love you, we are one and can never be separated my darling." "Yes ma’am," I whispered, not completely understanding what she was telling me but afraid to admit it. "You don’t understand do you? Let me make it simple for you honey, I know that you have been undergoing a lot of change and there is a lot of stress for you right now. I love you more than words can describe, I love you for what you are, my soft dove and always will till the end of time. We are inseparable. But, every now and then a woman wants something more primal and alpha," she told me while lifting me up. "Now let's get your silly sissy self dressed for your first big day at the new position, you know this came with a promotion, and a pay increase. I am so proud of you honey!" Karen continued talking while walking back towards the bedroom. "I am going to get a super quick shower while you finish making my coffee honey, bring it into the bedroom when it’s ready. I have laid out your lingerie on the bed, be a doll and get dressed while I am cleaning up." As she left the room I went to the kitchen to start the kettle and make her coffee. Such a simple task yet I loved doing it. I found solace in the simple things that I knew made her happy. I carefully poured the hot water over the fresh grounds in small circular motions, relishing the wonderful smell of fresh coffee. As I poured the aromatic liquid into her oversized but pretty floral cup the dark coffee blended with the sweet cream into little chocolate colored swirls. I was a bit surprised to hear the shower turn off in such a short time and stopped my daydreaming to rush to the bedroom and to begin getting dressed. Quickly setting her coffee down on her nightstand I saw the clothes that had been placed on the bed for me. Gently I lifted up the pale pink bra, the material was a shimmering satin with stiff underwires and thick padded cups. Sliding my arms through the straps and twisting behind me to fasten the three little hooks I shuddered at the feeling, how sexy it was having the firm pressure of the silky material around my chest. After adding in the breast forms and adjusting them to sit properly I gave a little jump and watched in amazement as my boobies bounced. Just feeling the weight and the jiggle made my little member try to get hard. Next was a matching pair of shiny pink firm control brief panties that came up high on my waist. There was also a large purple overnight pad lying on top of the panties. Knowing what was expected of me I pulled the panties up my legs, stopping when the waist was at my thighs. Opening the pad and unfolding both ends and pealing back the plastic cover I placed it in the bottom of the panties so that the wings would overlap the crotch area. Carefully I pulled the waxy paper off of the tabs and folded them over to secure them around the outside of the panty gusset. With a sigh I slid the panties up, pulling firmly on the waist, feeling the thick pad between my legs. Sliding my hand down the front, tucking my little chastity cage down and with one last tug pulled the panties and pad fully into place, hiding my smallness and protecting my clothes from the inevitable leakage. The only remaining piece of clothing was a pair of hose, but these only came to my knees. Rolling them up and putting them on I actually felt a little sad, missing the silky feeling of having my legs encased in nylon. I heard a laugh from the other side of the room and looked up to see Karen, towel around her chest, a hand up at her mouth, giggling at me. "Oh sweetie, the look of disappointment on your face was precious, are you upset because I didn’t have stockings and garters laid out for you? We will do that next time if you like, or panty hose, you will love those, but this morning we are a little behind schedule so you’re going to have to suffer with only wearing knee-highs." "Now let's talk about how you will be dressed today honey," Karen told me while sitting down on the edge of the bed and patting the covers next to her. I obediently sat down next to her. "I want something pretty and feminine, but I’m afraid you aren’t quite ready for skirts and dresses just yet," she said as she went to the large walk in closet. She emerged almost immediately with clothes in hand. Placing them on the bed next to me she smiled and asked if I thought they were pretty. Laid out were a pair of bright pink capri pants with decorative little tassels at the leg hems and a pussy bow blouse in white with a pink flower print. The bow at the neck was huge and the long sleeves were bloused out and puffy. These were super feminine! Karen placed a pair of pink block heeled sandals with a single wide strap at the front and a matching wide ankle strap with a three inch heel. I could almost feel bile rise up in my throat as I looked at the outfit I would be wearing. What happened to the navy pants and white button down blouse we bought I thought to myself. Those were feminine but not like this. "Honey, I know you were thinking that you could wear some of the more conservative things we picked out but after seeing how pretty you are in makeup and with your beautiful new hairstyle I just don’t see Brie as being so ‘plain Jane’. Brie is ultra feminine, girly-girl, don’t you agree?" she asked, placing her hand on my knee in an effort to calm me down. "We can take the mundane clothes back for a refund and use that money to buy you some pretty dresses and skirts." "I guess so," was my mumbled response. "Get dressed sissy, I want to watch you put on your pretty clothes then I will help you with your makeup and hair," Karen told me, ignoring my gloomy response. With the same enthusiasm as a death row inmate walking to the gas chamber I began to dress. Pulling the pants on I found that not only were they snug but the material had a little stretch to it and hugged my curves, particularly my butt. As expected there were no pockets, well there were pocket slashes but they were only decorative. Pulling up the zipper and affixing the two small gold buttons through the corresponding button holes in the front I looked down to see that the legs did indeed stop about mid calf and the cute little ball tassels danced merrily about when I moved my leg. Lifting up the blouse I first had to undo to bow and three small white pearl buttons at the high collar. The material did feel wonderful as it slid over my arms and chest, smooth and silky, pretty. Pulling my wrists through the wide elastic cuffs I noted that the base of the blouse flared out a bit and set very nicely outside of my pink capri pants. Buttoning the collar pulled it snugly around my neck and felt very odd. Karen helped me finish by re-tying the huge, almost clown like bow. Looking in the mirror there was no mistaking what I was, a sissy fag. My mood began to get darker as I allowed my resentment for being made to dress like this to grow and fester. Without comment I slid the shoes on and fastened the buckle for the ankle strap, standing up I was surprised to find they were fairly comfortable due to the wide heel and probably also to my practice the day before in the wedges. Still I would not allow myself to acknowledge anything pleasant about this situation. I could hear the strain in her voice as Karen tried to stay pleasant even with my ever souring mood. "‘Brie, be a sweetheart and go grab your purse for me so we can add some of the makeup you will be needing today for touch ups." Without a word I walked over to my side of the bed and picked up my large patent pink bag and brought it over, plopping it down a bit more nonchalantly than intended. Cutting her eyes towards me with a harsh glance she opened the bag. The first thing that I saw was the translucent pink dildo in it’s clear bag. In a deadpan voice, almost trying to sound masculine I told her, "That needs to come out of my purse so no one will see it if I have to open my bag around my co-workers." The words came out more forceful than I intended but mentally I was giving myself a little ‘high five’ for standing up for something! Karen reached into my purse and pulled out the case and set it down on the dressing table. In a tone so cold that it could have frozen water she replied, "Oh yes sissy, I will most definitely take this pink dildo out of your purse." With that she stood up and walked into the bathroom only to return seconds later with a tube of KY jelly, a hand towel and another Always ultra heavy overnight maxi pad. "Take your pants down sissy," she told me. I stood still, looking at her like some sort of idiot, not moving. She reached out, grabbing my bicep and shook me, pulling me towards her. "I said drop your fucking pants sissy, NOW!" she said through clenched teeth. Her face was flush with anger. Oh shit, I had really messed up I thought as I tipped forward, thrown off balance by the force of her tug on my arm. Scrambling I unbuttoned my pants and pushed them down to my ankles. "Panties too bitch!" she told me in a scornful voice. "Now bend over the makeup table and if you move or utter one complaint I swear I will take my hairbrush and beat your tender cheeks until they bleed!" I complied quickly, pulling down my panties but being careful not to wad up the maxi pad, almost toppling over the makeup table in my effort to bend over quickly as possible. I felt her fingers at my crack again, and then the cold, slimy lubricant, but this time was not gentle. This time she had slathered a huge glob onto her fingers and was pushing it into my asshole, then she gathered another huge blob and began working it in. Taking the dildo out of its clear case she coated it completely from tip to where the shaft met the balls with lubricant and then, with no warning I felt it being shoved into my rosebud until the balls seated against my cheeks. It was so slippery that when she released pressure it began to back out. "Hold this in place for me so I can fix your panties," Karen told me. Reaching around I used my fingers to push against the suction cup base that was beneath the balls, keeping the slippery shaft crammed tightly up my ass. I heard her unwrapping the maxi pad and putting it in my panties, then with a huff she went back to the bathroom and returned with a third, unwrapping it and putting it more towards the back. Glancing down I saw the wadded mass of pads in my panties and dreaded the feeling of having to pull them up. "Stand up slowly," was the next curt command from my wife, to which I immediately complied, slowly standing up while continuing to keep pressure on the dildo. I felt her wiping some of the jelly lubricant off of my butt cheeks with the hand towel. When I was upright she grabbed my panties and unceremoniously yanked them up, wedging the mass of pads against the base of the dildo. "Tuck your little prick and turn around," I was told. Cramming my cage down so it was hidden and arranged so my drippings would weep into the first maxi pad I turned around. With every movement I could feel the cock in my rear sliding back and forth. The panties prevented it from coming out more than a few inches but when I moved or shifted they would push it in deeper or let it slide out a bit. The whole time my little caged clittie was trying to swell in the steel cage. "Do you have anything else you would like to demand of me little sissy, as you can see you no longer have a pink dick in your purse so you should be quite happy," Karen huffed, while putting her hands on her hips. "Now pull up your pants and let's get your makeup done, unless you really do want to say something else." I was afraid to speak, pulling up my capris I hastily fastened the buttons and pulled the zipper closed and then sat down in front of the lighted makeup mirror. Without a word Karen draped a towel over my blouse and handed the moisturizer sunscreen to me. Remembering how Tony applied it I did my best to replicate his actions. When I was finished I fastened the lid back on the jar and gently returned it to the table. "Pay attention sissy, I will walk you through this but you must learn quickly how to do your own makeup," Karen told me, with anger still in her voice. Breaking down I turned to her, slid off of the chair and pressed my lips to her toes. "Please don’t hate me. I am so sorry for being bad Mrs Karen, please find it in your heart to forgive me, or punish me more and then forgive me. Please don’t be mad at me." I could see the tops of her feet covered in my freely flowing tears. I was so upset with myself for being so stupid, all morning I had been acting like a jerk. With an exasperated sigh Karen took a step back removing her feet from my reach. "I don’t hate you sissy but I am furious with you at the moment and no amount of begging will change that. You do so good and then for no reason at all something triggers you and you fall back into trying to be a boy or something. It is like two steps forward and one step back with you and it frustrates me to no end. Now get up and sit down so we can get your makeup done." Without a word she began to work on my face, explaining as she went. In a few places I asked questions which Karen answered but without the fun banter that we normally enjoyed. Had I hurt her that much this morning? When my makeup was done she removed the white towel that was protecting my blouse and I was amazed at the effect. Huge brown eyes with medium arched eyebrows and lightly bronzed eyelids, the effect was amazing the way it made my eyes look so large and soft. The bronzing on my jawline defined my face, seeming to lift my cheek bones and Karen had done my lips in a darker liquid mat lipstick then applied a light coat of a pink gloss. The effect was stunning. Stepping behind me she began to work with my hair, pulling up the back into a loose flip and fastening it with bobby pins while working the side part and sweep in the front for a half up, half down look that was soft but very professional looking. When she was done all I could see in the mirror was a beautiful woman. "Mrs. Karen?" I asked in a quiet tentative voice. "Yes," she answered curtly. "Thank you for making me look so pretty ma’am...." With a small ‘huff’ she turned and put some of the items from the table into a small pink makeup bag, placing it in my purse, she paused and then got up and went back into the bathroom. When she returned it was with the realistic, huge dildo that she had used on herself this morning. With a sly smile she opened my purse and stuffed it in, leaving a little bit of the tip protruding out of the top of the large bag. "Any comments or requests concerning this sissy?" she asked with a toothy smile. The only thought going through my mind was that if she decided to put that thing up my rear it would split me into and I would die! "No ma’am Mrs. Karen, thank you for packing my purse for me ma’am!" I blurted out quickly. The urgency of my reply was not lost on her and she met my response with a wide smile and air kissed me on each side of my cheeks. At least she showed me some affection, the first since my blow up earlier so I took it as a positive sign. "Brie, please grab the box on the counter and my purse, we need to go," she told me while walking out the door to the garage. Crap I realized that I had not changed out her bag, she had on her very professional business outfit with that fun Dooney bag. My selfish actions this morning had cost my wife not having a matching purse for her outfit. With this thought weighing heavily on me I picked up her purse, the box, and my bag and carefully walked out to her car. I soon discovered that even the way I approached sitting down in a car was being modified by the new higher heels I was wearing. I found that it was easier to lower myself to the seat, similar to how Karen had taught me to sit more lady like, and then swing my legs into the car. When my tush hit the leather seat it drove the dildo to its full depth, the twisting motion caught me by surprise and I let out a little gasp which made my wife smile just a little. "Ma’am, I am sorry," I told her as I arranged our purses in my lap after clicking the seat belt into place. "Yes honey, I know. You explained that to me earlier," Karen told me while waiting for the garage door to fully open. "No ma’am, I mean that because of all the fuss I caused this morning I didn’t get a chance to change out your purse. Your black patent Kate Spade bag with the chain strap would have looked amazing with your outfit today. I’m so sorry." I really felt bad, I took so much pride in making sure that my wife was a beautiful and felt pretty every day and I had let her down. Still in the garage she put the gear shift in park and brought her hands up to her face. I was a little confused and it took a second before I noticed that her shoulders were shaking, she was crying. "Mrs. Karen, is everything OK? I’m sorry I was bad today, I didn’t mean to make you cry." I was frantic, what was wrong. I couldn’t stand to see my wife upset like this. Turning towards me she tried to smile but it seemed so hard for her to do. "Oh Brie, you haven’t done anything wrong. Just now your concern for not changing out my bag, even after I had to correct you for your behavior, you are such a sweet dove. I absolutely abhor having to be mean to you but I know that I also have to be strong and strict to help you in your journey." "Mrs. Karen ma’am, I love being Brie for you," I whispered, looking at her bag in my lap. "Yes, honey, I love you being Brie for me too, it is who you are and who you should be," Karen reassured me. Continuing to fidget as she drove us to my new office I couldn’t find the words to tell her that I wanted to be her tender sissy, someone to love, to play with, but I was afraid of what was going to happen when I got to the office and what Mrs. Penny might do to me. For the rest of the ride I sat quietly hoping that she wouldn’t get upset with me for doing so. As we turned into the parking deck my terror level began to escalate. It seemed like every time I sat in the passenger seat of my wife’s car and we parked somewhere it was the start of a new panic attack for me. I concentrated on closing my eyes and slowing my breathing. My heart was literally coming out of my chest it was beating so hard. I was not as terrified of showing up wearing women’s clothes but of my boss Mrs. Penny. She scared me. Putting the car in park Karen turned to face me after removing her seat belt. "Honey, are you okay? You were very quiet on the ride over here and you are white as a ghost," she asked. I was still trying to get my breathing under control and couldn’t answer her. I was afraid if I tried to speak I would bust out into tears. I tensely nodded my head, working hard to hold back tears. "Remember, whatever happens I love you, keep that in the front of your mind and just concentrate on being obedient, subservient, and getting through the day and evening." "Yes ma’am." With both of our purses and the mystery box I followed my wife to the elevator. When the doors opened on the fifth floor I was very impressed with our new office lobby. Because we were a small team and working on a special project we would not have a receptionist, but the lobby was still beautiful. All chrome and glass with sleek black leather chairs and a dark marble floor. Walking to the frameless glass double doors I badged in and stood to the side while Karen opened the door for me to walk through. With a great deal of anxiety I walked into the new office, for me this seemed to be the point of no return. Once Penny, Anu and Amanda saw me like this there was no more Brian, no more male. What was I suppose to do when they saw me and started laughing. I almost asked my wife but then I remembered. She had already told me what to do if we met a woman that she or I knew, she told me on the trip to get my hair fixed. In my little sissy mind I decided how I could make up for my behavior this morning, this was an all or nothing, no holding back moment. I had to embrace and accept my humiliation. Walking around the wall the first person we saw was Mrs. Penny. Karen gave her a quick wave to get her attention as she was on the other side of a set of cubicles. Turning our way she did a bit of a double take and I swear her jaw actually dropped open a bit. As she approached I tried to clear my mind of everything, all my pride, all my maleness. I kept thinking of what Karen told me in the car, no matter what happened today she would still love me. When Mrs. Penny stopped in front of us I lowered myself to my knees and gently placed my lips down, almost touching the tips of her navy pumps but not quite so as to not get any lip gloss on them. "Mrs. Penny, would you please let this silly sissy hold your purse and serve you in any way ma’am," I begged, with my eyes still locked on the tips of her shoes. I heard a gasp from my wife and out of the corner of my eye I saw her knees go together and flex a bit, dipping down. It may have been my imagination but I thought I could smell her excitement, had I given her another mini-orgasm? "Yes Brian, you may hold my purse all you like but first stand up and let's have a look at you," Mrs. Penny told me. Leaving the box sitting on the floor next to me I stood up, pulling Mrs. Karen’s and my purse straps into place on my shoulder in the process. I averted my eyes, not wanting to meet her gaze. "Karen, he is beautiful....no I can’t even use that pronoun anymore, she is beautiful. I knew you told me that she was going to have her hair and makeup done but...I don’t have words," Mrs. Penny put her fingers under my chin lifting my face up, "look up at me Brian". She told me. I did as commanded but still found it hard to meet her eyes in my humiliation. My wife spoke up. "Thank you Penny, I agree she is beautiful, way to beautiful to ever go back to the ‘he’ that was. I have been calling her Brie, it is a pretty name that a makeup artist gave her, to be honest I think my little sissy was a bit smitten by him." Hearing her tell my boss that I liked a guy made my cheeks turn bright red and both women broke out into giggles. "Well...Brie, your desk is going to be in the first cubicle so why don’t you go get settled in. Your things from the old office are in a box sitting at your desk," Penny told me, dismissing me from standing in front of her. "Oh Brie, if you want to you may go into my office, it is right in front of the cubicle, and get my purse if you would really like to carry it." "Yes ma’am." Karen spoke as I began to walk away, "Honey, the box I had you bring from home has some nice stuff for your new desk and cube. Make sure you put all of that out as well, it will make it feel more personal for you." "Yes ma’am". I replied and then turned to carefully walk away. All the kneeling and getting back up had thrust the dildo in and out of my butt and I was beginning to get excited again. I had only taken a few steps. Swinging my hips as I had been taught, when I heard Mrs. Penny. "Brie, hold up a second, don’t move." "Yes ma’am," I replied while thinking to my self, ‘Oh no, what now?’ "What is going on back here?" she said, pointing to my rear end. Karen burst out into full fledged laughter, even giving a cute little snort or two before she could get calmed down enough to respond. I just stood their wishing that the floor would swallow me up so I could disappear. Karen and Penny walked up behind me, Penny stopping a few feet short and looking directly at the back of my capri’s. Karen came up next to me, I could see her smiling from ear to ear. "You see Penny, this morning little Miss Brie had a temper tantrum because she was afraid someone at the office would look in her pretty pink pocketbook and see her pretty pink dildo she keeps there. In a huff she demanded that I remove it from her bag at once!" Karen said in a mocking, lilting, overly sissy voice. Penny had started to smile now. "Yes, Please continue to explain," she said, while bending a bit to get a closer look. Karen’s hand slipped down below my waist to the back of my pants and I felt her pushing on the maxi pads that were over my dildo. "Well, I took it out of her purse and put that pink cock right up her pretty little cherry hole." As she said this Karen began to roll her hand around, wiggling the base of the dildo. "The panties hold it in but not tightly so as she walks and wiggles that cute ass it is pumping in and out and side to side, I put the extra maxi pads back there for a little added support and in case she leaked any." Penny put her hand up to her mouth, I could see her eyes lighting up with humor and then it started, the soft feminine laughter. She laughed until I saw tears coming out of her eyes. "You mean....wait a second Karen....are you telling me....she has a pink cock shoved up her butt right now?" Penny tried to ask between bouts of laughter. "And when she walks, it wiggles! Could she, I mean, why isn’t she getting a boner?" she asked, taking a step forward and switching her appraisal to the front of my pink capri pants. Karen was still laughing and wiggling the base of the dildo slowly while she tried to respond to Penny’s questions. "Okay, So one thing at a time..." And then another snort of laughter. "So first, she isn’t big, actually she is tiny...we, oh god I can’t breath I am laughing so hard, we call it her ‘sissy clittie’ because it is so tiny and cute, all shaved and bare, it really looks more like a clit than a penis." I was turning beat red and on the verge of tears, I had never been so humiliated in my life, and to make things worse Amanda and Anu had just walked up from the break room and had heard everything my wife had just said! Gaining some composure Karen continued her answer to Penny. "Even with it being soooo small I decide it was best to protect womankind from having to endure anything so insignificant so she is locked up in a very secure but tiny steel chastity cage. That’s why she isn’t sporting any wood!" At that all four women exploded into another round of laughter. All I could do was stand there, purse straps on my sagging shoulders, a cardboard box in my hands, looking down at the floor wishing I would just die. Penny, wiping tears from her eyes put her hand on my butt where the thick pads and dildo base were and pushed it in. Feeling it move she squealed and pushed it again. "Oh shit Karen, you really do have a cock in her ass! I can feel it, oh hell, are those balls too?" "Oh yea, those are balls!" Karen laughed. "But the special thing, something that I didn’t realize before I shoved it up there is.....oh shit, let me get my breath....when she walks or wiggles....when she....oh hell...it gets her excited and I think if she kept it up that she would squirt in her little cage!" Karen blurted out between snorts and fits of laughter. "She can do that, ‘squirt’ from something in her butt, even with a chastity cage on?" Anu asked while stepping to the side and leaning over to get a better view of the protruding lump at the back of my capri pants. With a wicked smile Karen gave the base of the dildo another wiggle and then stood up. "Sissy, why don’t you answer that question for your coworker by telling her about Saturday night?" I was standing there stunned, my mouth hanging open in disbelief, unable to even move. "Sissy, go set your box down on your desk, run to my office and get my purse, come back and greet Anna and Anu properly, like you did me this morning, and then answer the question like your wife instructed you to," Mrs. Penny told me in a very commanding tone, leaving no doubt that I had no choice but to comply. Trying to walk as carefully as possible to keep the wiggling motion of the dildo to a minimum I did as Mrs. Penny instructed. Walking out of her office with a third purse, I placed her large maroon leather coach tote on my left shoulder. When I returned to where the ladies were I saw that they had taken seats either in my chair or on my desk. Kneeling down I placed my lips on Miss Amanda’s toe’s that were exposed in her leather sandals and then as close as I dared to the toe of Miss Anu’s black ankle boot, begging each to allow me to be their purse sissy and letting them know that I was at their beck and call. This elicited another round of laughter. "Oh yes sissy," Anu responded. "You may most definitely be my little slave if that is what you really want." With a giggle Amanda replied, "I warn you sissy, I can be mean when I put my mind to it. Yes, I accept your offer of servitude." "Now, I believe that you are suppose to explain something to us about how a sissy squirts," Mrs. Penny reminded me. It felt like all the blood in my body was rushing to my head, I could hear the pounding of my heart in my ears, this was going to be so humiliating. In a quiet voice, unable to look at anything but the pretty toes and shoes of my tormentors I began telling how my wife had bound me and took my sissy virginity and how I squirted for her. At points in my story Karen would make me add more details, like how it felt when my juice began to just slowly leak out instead of shooting in jets like a man’s would. She even showed some of the photos from her phone and told them about how she had made me suck my seed out of her soiled panties. It took a while for the laughter and the silly questions, which I answered politely, to subside. Karen even emailed some of the photos to them at their request. Finally Miss Amanda gained enough composure to talk. "Sissy Brie, I need you to answer a question but you had better answer it the way that you are expected to as a sissy, do you understand?" she asked, while standing up and straightening the bow on my blouse. "Yes ma’am." "Do you like eating cum sissy?" Amanda asked, with a wicked grin on her face. I noticed that both Mrs. Penny and my wife perked up at this question. I was sweating so hard that I feared my makeup would begin to run. My ears were burning and my knees were trembling. I was biting my lower lip so hard that it hurt. Glancing at my wife I could see that she had gone from a laughing, silly face to one that was dead serious. Thinking back to the other night I remember how insistent she was that I would always eat my seed, any time it leaked. I did not want to eat cum, true it didn’t hurt me when I did it but it was so degrading, such a sissy thing to do. Another nervous glance at Mrs. Karen who now had her arms crossed, her pretty painted nail tapping furiously against her bicep in anticipation told me the answer I was expected to give. The answer that a sissy must always give. The shame and humiliation swelled up in me to the point that I could not stop the tears from coming. "Yes ma’am Miss Amanda, I like eating cum," I said with my head held low, failing to hold back my tears, chewing on my lower lip hoping the sharp pain would wake me up out of this dream. "Well, that is a good thing for a girl to know now isn’t it?" she said with a giggle as I continued to tremble in humiliation, my little penis raging against the confines of the small cage. 'It is the effect of the dildo in my rear,' I kept telling myself but deep down I knew that was not the complete truth, it was the embarrassment, the attention that Miss Amanda was lavishing on me, and the thought of her making me eat cum! I felt Karen’s arms wrapping around my shoulders in a hug, "Honey, I have to leave you and go to work now. I believe that these wonderful ladies have got you under control." With a kiss on the cheek she lifted her purse from my shoulder and then turned to Mrs. Penny. Penny looked down at me, then spoke to my wife, "Karen honey, you are coming to the house tonight for the team building dinner aren’t you?" Putting her hand lightly on Penny’s forearm Karen replied, "Yes, wouldn’t miss it for the world. Oh by the way, just like we discussed yesterday you have full control over Brie while she is at work, I don’t want to confuse her with whether or not she has to obey you fully, let’s just keep it simple and say that when I’m not with her you are in total control. Have some fun with her," Karen added with a pleasant smile. "Brie, I want you to be a good sissy for everyone, and a good engineer. Work hard and make me proud of you honey," Karen told me, ending with a kiss on the cheek. "Oh Karen," Penny said as my wife was walking towards the door, "Don’t worry about swinging by here, I will take Brie home with me." "Sounds great then, see you at six. Bye ladies, have fun," Karen told everyone as the glass door closed behind her. I stood silently looking at the floor, petrified of what would happen next. "Alright everyone, this has been a tremendous amount of fun but we need to get settled in and make sure that all of the computers and servers are running as well. Get to work everyone!" Penny stated and then walked away, leaving her purse with me. I was still in a state of shock from the intensity of the humiliations that I had just endured and had to do my calm breathing exercise to refocus myself so I could get to work. As I began to calm down I first addressed the boxes from my old office. These were reference books, old design notebooks, and important folders. I filed or placed everything very neatly in it’s proper place. This private cubicle was much more spacious than the one I shared with three others in my old office. It had a large L-Shaped desk, a separate work table with two chairs for small team meetings, and a large locking book case. The cube walls were also much higher. The computer set up went very well, Two large curved monitors and my docking box had already been set up. All I had to do was plug my laptop in, set up the screens the way I wanted them, map to the new servers, and install drivers for the printers in this office. Surprised at how smoothly that went and it being only eleven in the morning I glanced over at the box Karen had me bring in. With some apprehension I opened the box, not knowing what to expect after the events of the past couple of days. With a sigh of relief I noted that it did not contain any bondage gear or huge plastic dicks. The first item was a pink high heel tape dispenser which I sat out on my desk to replace the mundane old tan one that I had. She had also included a pink blotter for the desk top, and an assortment of pink, purple, and pastel gel pins that I put in my top drawer. Next were a three small framed photographs, one of my beautiful wife that was taken on our vacation to Italy the previous year, the other was a detail photo from our wedding of her purse, heels, and jewelry, and the third was one of her and I from our honeymoon. I placed these in areas of my desk that would allow me to see them all the time. That was such a sweet gesture and it made me smile. The last bit was a larger makeup kit that included foundation, a couple of eye pallets, bronzer, blush, powder, eyeliner, mascara, and several lipsticks and glosses. This was in a large, shinny pink makeup bag and I tried to rearrange my top drawer to fit it, and then thinking better of it decided that there was plenty of room on my desk to just keep the bag handy. It was almost noon when I finished with my desk set up and had broken down the boxes. I hadn’t really thought about lunch and did not have a chance to pack one from home with all the chaos this morning. I decided that it would be nice just to hide at my desk, my stomach was still upset from all the events of the day. Well, that was my plan, which was going quite well until I heard Miss Anu. "Hey Brie," Anu said while peeking over the side wall of my cubicle. "You didn’t bring your lunch today did you?" "No ma’am but I don’t think that I am very hungry today. I was going to stay here and try to start with some work," I said, it was a partial lie and partial truth. Deep down I was just hoping everyone would go out and I could have a little quiet time to get my thoughts around everything that had happened today. "I don’t think I like the tone of your voice sissy, I would like to go out to lunch and don’t really want to eat by myself," she said, while walking around to the cube entrance. "Penny is good with us taking a long lunch, I checked with her. She did ask that you return her bag to her office before we leave though." With little recourse and knowing better than to talk back or show any disrespect I took a quick breath, smiled a silly smile and in a cheerful voice replied, "Yes ma’am Miss Anu. I would love to go to lunch with you, may I please touch up my makeup where silly sissy was crying this morning?" Returning my smile and seemingly modified Anu said, "Of course Brie, I would never think of making you go without fixing your face. We are going to have so much fun. When you are done just come by my desk and you can pick my purse up there. Don’t take too long." "Yes ma’am." I returned Mrs. Penny’s purse to her office and at the last second decided to write her a quick note thanking her for allowing me the privilege of being allowed to hold her bag and thanking her for selecting me for the new team and how excited I was to both be working for her and being allowed to serve her. In a moment of sissy inspiration I made a very neat lipstick kiss impression at the bottom of the note. Stopping at my desk for a quick touch up job on my makeup I did the best I could, looking in the mirror I knew it wasn’t as good as my wife or Mr. Tony could have done but it wasn’t bad and I was a little proud of myself. "Hurry sissy," Miss Anu called from the glass exit door, "grab my purse and hustle your little ass over here, turning around and lowering the waist of her black stretch pants and even her panties she continued. "You may kiss my butt and ask me to punish you for dawdling and taking so long." My face was glowing flush for what seemed to be the hundredth time this morning. I rushed to her desk to grab her purse, my dildo madly wiggling and thrusting in the process, combined with the humiliation of what I was going to have to do I nearly had a sissy orgasm by the time I picked up her large silver kiss lock clutch purse. "Run over here sissy and swing those hips while your doing it!" Anu demanded, her pert little tush poked out towards me. Immediately complying to her command, wiggling my hips. Moving with the exaggerated sissy motions had the effect of enhancing the movement of the cock that was pumping and wiggling inside me. I was moaning, my lips pursed in an exaggerated ‘O’ shape. Reaching her I began dropping to my knees but she stopped me. "No sissy, I want you to flex your knees and bend at the waist, holding your hands out like a sissy doll. Give my cheek a kiss and then pop back up to a standing position with your pretty little heels together, then a deep curtsy and tell me ‘Thank you Miss Anu.’" I did as she instructed, the motion of flexing my knees and then bending at the waist thrust the pink, plastic, cock deeply into my ass, standing back up with my feet together allowed it to slide out, and the curtsy delivered a quick series of thrusts. "Again!" she told me. "I want you to repeat this until I tell you to stop sissy!" I repeated the motions and the words for her again, and again. "Faster sissy!" she shouted. I began frantically bending at the waist, kissing her pretty cream colored cheek, then upright feet together, then the quick bobbing curtsy. Over and over, the pink cock pushed in and out, wiggling, until it became too much to bare. "Oooooohhhhhoooo..." I began to moan then, a high pitched little squeal, pausing my motions. Anu turned looking at me. "Sissy I did not tell you to stop! Faster girl, faster!" she demanded. Going as quickly as possible in jerky motions I continued torturing myself with the movements that drove the dildo in and out. "Maaaa’aaaammmm.....oohhhoooooeeeeeeeee....Miss Annnnnnuuuuuuuuuu," I tried to beg her to let me stop. "No sissy! I said faster now!" she shouted. All of our activity had attracted the attention of Mrs. Penny and Amanda who where watching, oh shit they were videoing this with their phones. I went as fast as I could knowing now that a sissy orgasm was inevitable. As it began to overtake me my body began to tremble. If I slowed down any Miss Anu would demand that I speed back up. Finally I felt it washing over my body like before. The feeling of a huge orgasm through my entire body from my toes to the tip of my sissy nose but when it reached my caged little sissy clittie there was just frustrating dribbles and leaking. I needed to cum so bad but I couldn’t, not like a boy. My breath was coming in ragged gasps and I started to slow down only to be yelled at again to speed up. ‘But I have already climaxed I thought to myself,' the women were relentless. With a few more repetitions of the exercise I felt another sissy orgasm begin welling up inside me. Oh no..how could this be, it couldn’t happen again but it was. I had lost control of what I was doing and was no longer kissing Miss Anu, I was just bobbing up and down, wiggling, and bending, driving the dildo in and out of my ass in a sex crazed attempt at some type of relief from the frustrations that had been building up over the past three days. It was approaching, something huge that I began to fear, but there was no way that I could stop now, on the brink of a cliff, just one more step, I could feel the pressure welling up within my swollen balls, then...then.... Whap! Whap! Whap! I felt thin streaks of pain on the back of my thighs as Miss Anu attacked them with a thin metal ruler. "Stop! Don’t move another muscle sissy!" came the command from Miss Anu, I froze immediately and felt myself falling back away from the brink of ecstasy. I was so close and now it was gone. In a cheerful voice she patted my cheek and said, "Come along sissy, let's go get some lunch and have some fun, just you and I." "Yes ma’am," I replied, almost at the brink of tears my frustration was so intense. I could feel heat coursing throughout my body and my rectum was pulsing from the stimulation. How had she know when to make me stop? Was it that evident that I was about to have a real orgasm? As I began walking, following behind her, I could feel the cold slimy wetness of my sissy cream in the maxi pad rubbing against my skin sending a shiver through my body. I was silent in the elevator ride down to the parking garage and once again fell in behind Miss Anu. The sound of our heels clicking across the concrete of the parking garage was surreal. I was still mentally reeling from my sissy cumming and the denial of what felt like the most intense orgasm of my life. To be honest my legs were still a little shaky. She led me to her car, a newer VW bug convertible in a bright yellow color. I saw the flash of the parking lamps as she turned off the alarm, unlocking the car. After doing that she just stood beside the drivers side door. It took a few seconds but then I understood what she wanted. Quickly I rushed over and opened her door, standing to the side while she sat down and then closing it firmly behind her. After I was seated she looked over at me with a smile, "I wanted you to do that so you would know that I don’t think less of you for pampering ladies. I didn’t mean to call you out on Friday night when you pulled your wife’s chair out to help her sit at the restaurant. If you would like you may do all those sweet little things for me today." "Yes ma’am, I would enjoy that," I replied, finally hearing something that I was very comfortable doing. "That is sweet of you, now let's go get a bite to eat," she said, putting the car in gear and backing out of the parking spot. I blinked as she pulled out into the bright sun, making a mental note to put a pair of sunglasses in my purse. We drove about 5 miles to a small, upscale strip mall and she parked in front of a little sushi place which excited me, I liked sushi! I hopped out of the car and rushed over to her side to open the door. "Thank you Brie," she told me. "Is this okay? Do you like sushi?" "Oh yes ma’am Miss Anu, I love sushi, thank you for taking me here!" I stated gleefully. I actually enjoyed my lunch with Miss Anu, she was very smart and fun to talk to, though I did remember to stay very subservient and polite during our conversation. We talked about the new job, the incredible sushi we were having, makeup and clothes. She was also intrigued by my fascination with purses. I blushed a bit and sheepishly looked down, "It is a little hard to explain ma’am but since I was a little boy I have always had a thing for purses. I think it is because, to me at least, it is the most feminine thing in the world and I seem to be excited by feminine things. Ladies purses are so special, they are pretty and feminine, and they hold everything that a woman may need for her day, that makes them even more special. Deep down I also think that men have driven female fashion to the point where it is tight fitting and usually without pockets. Throughout the ages women have used cosmetics to entice men, and they needed somewhere to carry all of that stuff. Being a purse holder for a woman, or for women in general is one little thing that I can do to make amends for this. By bearing the weight and burden, with the added humiliation of being a boy carrying a pocketbook I am, at least in my silly sissy brain, apologizing for being male, that sounds stupid doesn’t it?" "I had never thought of purses like that," Anu said, taking a sip of water and dunking a piece of tuna roll lightly in soy sauce, "I think it is very sweet of you no matter what the reasoning but hearing why you love doing it makes it even more special. I think that we will work well together Brie. It first I thought you were weird but I think I have a better understanding of you now, and that show you put on in the office for me was priceless!" "Thank you ma’am, I am glad that it pleased you," I said, blushing again and looking down. Once again my plain toes seemed to stand out as just silly in my pink sandals. I was wiggling them a bit and looking down at them when Anu spoke again. "You want your toes painted don’t you sissy?" she asked with a bit of a giggle. I looked up at her. "Yes ma’am, that is silly of me isn’t it?" "Well, I don’t know a lot of men who long to have their nails done but then again, if I didn’t know who you were I would never, in a million years, think you were a man. Hell, if I saw you out at night I would probably be jealous." Taking a good look at my toes, and then gently lifting up my hand to look at my nails she smiled warmly, "No, what I think is silly is someone as pretty as you having boy nails, let's finish eating and I will help you fix that." "Thank you ma’am, that is nice of you. Do you think that Mrs. Karen will mind if I do this without her permission?" I asked. "No, actually I think that it would be a nice surprise for you to give her. She seems to love it when you take little steps towards being her sissy on your own." After finishing lunch Miss Anu took me to a nice nail salon that was not far from the office. Having me wait in the lobby area she spoke at length with one of the nail technicians. After a few minutes a petite young lady wearing a pink jacket approached me. "Brian, follow me please". She said while turning and walking towards a row of pedicure chairs. I was a little shocked that she had called me Brian but one glance at Miss Anu and I realized that she had done that specifically so that the lady would know I was not a woman. "Have a seat please," she told me indicating a seat between two other ladies already having their feet tended too. I was a nervous wreck, trembling as I sat in the chair which was raised up off the floor with a large basin below the foot rest. Looking at me the young lady put her had on my knee and with a gentle smile said, "Brian, please don’t be afraid, you are going to love the whole process. I promise that there is nothing bad, it is all about being pampered and making you look and feel pretty." "Thank you ma’am, I will try to relax and enjoy it," I replied with a slow deep breath. With that she leaned my chair back a little and shifted my feet into the basin of water which was warm and did feel wonderful. "This is a foot soak, we have some minerals and lotions added to the water to help soften up your feet, I am going to turn on the bubbles now so don’t be shocked," she told me. Looking a couple of chairs over to my left I saw Miss Anu leaned back with her eyes closed enjoying her foot soak. "Yes, ma’am, and you are right this feels great. Thank you so much for not being mean to me...ahmmm...if you would like or don’t mind....well, my friends call me Brie, that is if you’re okay with that ma’am." "Yes, that makes a lot more sense to me than calling you Brian," she said with a smile. "Do you mind if I ask you some questions while I work? I like talking to my clients and I am so curious, but you are a client and that comes first, I don’t want to be rude or make you feel uncomfortable." "No ma’am, I don’t mind if you talk to me or ask me questions. I imagine that I’m a bit of a curiosity," I replied with a genuine laugh, thinking about my appearances as well as the dildo that was secretly up my butt. "Well, I am just having a hard time believing that you are a boy, I have seen guys in drag, they come in here all the time, but you are so different. They are fun to joke with and some of them are really pretty but you are so different." "How am I different ma’am?" I asked timidly. "Bingo! That is exactly what I am talking about. Just then, you are so polite, sweet, and bashful...no, bashful may not be one-hundred percent correct, what is the word I am looking for?" she said excitedly while lifting my feet out of the tub, drying them with a soft towel and setting them up on the footrest, taking a seat on a low rolling stool. Blushing down to my toes because I knew the word she was looking for, I diverted my eyes down to look at my pink Dooney and Miss Anu’s pretty silver clutch sitting in my lap. "Submissive ma’am, is that the word you are thinking of?" "Exactly!" she blurted out as she began to trim and file my toenails. I giggled a little because it tickled to have someone touching my toes. "Sorry about that, I will be a little firmer with my grip, you have ticklish feet I see. So what’s with the submissiveness? It is cute but I have never seen anyone so...so...demure. Why?" "Have you ever heard of a sissy ma’am?" I asked, feeling my body heat up with feelings of shame. Putting her nail file down and lowering my feet back into the warm tub of water she looked back up at me with a quizzical expression, "I’m not sure. I mean I know what a sissy is, like a girly boy or someone who is afraid or something but I’ve never really thought much about it." "I am a sissy ma’am, but there is more to it I guess. I don’t understand everything but I will tell you what I think it is. Deep down all I want is to be controlled by ladies, to serve them, to help make their lives easier, more pleasurable, and more amusing. I didn’t dress like this because I wanted to....I dressed like this because my wife wanted me to, she picked out every piece of clothing. I think that is something that is important about sissies, that we don’t do things because we choose too, but we choose to allow our superiors to decide for us. Mrs. Karen, my wife, says that is why I am embarrassed and ashamed all the time, because sissies are shameful little creatures," I tried to explain, my voice very quiet and halting. Lifting up my feet again she began to work on my cuticles, pushing them back with some type of wooden stick. I winced at first expecting it to hurt but with my feet being so soft from the soaking it wasn’t unpleasant at all. Next she began to work on my heels with a rough pumice stone which also felt much better than I expected it to. Closing my eyes with a sigh I allowed myself to relax a little. "What type of things do you do to serve women Brie? How do you provide for their pleasure, make their lives easier, or amuse them? Is that too personal? She asked me, actually blushing herself a bit. Looking down she began to rub something that felt a little gritty on my feet and calves. "This is an exfoliating scrub, it cleans off all the old dead skin and such, you will love how soft your feet will be. Let me rub this in, then we will rinse your tootsies, and then I will massage in a very pretty lotion, you’re going to love that." "What is your name ma’am? If you don’t mind me asking, I’m sorry if that is too forward, if it is I can ask Miss Anu to have me punished for upsetting you," I asked in a quiet voice. It was just that she was being so nice and I hated not knowing her name. "My name is Kim, but why would I have you punished for asking my name?" Then I saw a smile and a little twinkle in he eyes. "Ohhh, I think I understand now, or have an idea of just how submissive you really are. You aren’t just submissive, you are literally owned by women aren’t you?" "Yes ma’am, I hadn’t thought of it that way but I believe you are right." "Are you okay with that Brie?" "Oh yes ma’am Miss Kim, I am!" I blurted out a little too quickly. Blushing I added, "I am happy with it ma’am, I love serving my wife, she is the most wonderful person in the world. She is always helping me be better. Sometimes I misbehave and she has to punish me for my own good and that makes her sad but I know she does it because I am a sissy and I need her help." With a bit of a giggle Kim picked up a bottle of nail gel and held it up, "This is the color your friend selected for your toes, are you good with it or would you like something less pink?" she asked as I read the label on the bottle of bright pink polish which said, ‘Barbie Pink’. "Yes ma’am, it is fine. I don’t think that I am allowed to change her selection anyway," I told Miss Kim. "That is so cute, so you really don’t have any say in this do you?" "No ma’am." As Kim began to insert a foam strip between my toes to separate them she returned to her original question, "You keep changing the subject Brie, earlier I asked you what type of things you do and now I also have to ask how you are punished. This is just too juicy to let go of." I had hoped to divert the conversation a bit but I could see that Miss Kim was much to smart for me to have any influence over, blushing and stuttering I began my confession to her. "I, well my wife, she likes me to...you know, she enjoys pleasurable things," I stammered. "I don’t understand Brie, everyone enjoys pleasurable things. Why would a woman want to have a sissy?" she asked me. There was no avoiding it, talking as quietly as I could manage so that the people on either side of us could not hear I began, "My wife enjoys having me please her with my tongue and lips." Feeling the heat from my blushing rising up and turning my ears red, and my little sissy clittie swelling inside the tiny cage I continued explaining, "She...my wife....she enjoys relief and incredible orgasms but she also enjoys... well it makes her happy....that, well, that I don’t get to have regular orgasms. She enjoys me staying in chastity while she is free to, you know, feel pleasure whenever she desires." Kim had just finished painting my last toe-nail and was reaching for the UV curing light but her hands came up quickly to her mouth and her eyes were wide with surprise. "You're in a chastity cage!" she blurted out loudly. Looking to either side of me to see if anyone had heard I was devastated to see not only the ladies sitting next to me laughing and looking at me but even Anu who was two seats away had been able to hear Kim’s outburst. There were giggles, glances, and whispers accompanied by pointing and even a camera phone picture or two from the ladies in the pedicure area. "Oops, I’m sorry sissy, I guess I was a little loud wasn’t I?" Miss Kim asked me with a giggle, not seeming that sorry about it at all. "Let me get this lamp over your toes, it will cure the nails. Don’t be worried about the light, the lotion I used has sunscreen so your cute little piggies won’t get burned. Now, tell me about you punishments Brie, what do you do to deserve them and what are they," she demanded. "Do I have to Miss Kim, this is really embarrassing for me ma’am," I pleaded quietly. "You are refusing a direct request from a woman, that sounds like a punishable offense to me Brie, am I right?" she asked, standing up and leaning in towards me. "Yes ma’am, it is. Well to be honest..." I tried to finish my sentence but the words got caught in my throat. "Go ahead, what are you trying to tell me Brie. Is it really that bad?" "No ma’am, it’s just that, well you don’t need a reason to have me punished other than having it done for your enjoyment I guess, or maybe just to have me suffer or something. I don’t think you have to have any reason at all ma’am. I’m just a sissy," I managed to choke out the words, knowing that now there was someone else who had power over me. Laughing softly Kim asked me to get up and follow her. Arranging my purse and Miss Anu’s bag I carefully got up and trailed behind her to a manicure table. She indicated that I should sit in the chair behind the table while she moved to a swivel seat in front of it. "Your friend selected an active length nail which will stick out about 4 millimeters from the tip of your finger but I would like to do something different, you can consider it my little punishment that I am giving you. How does a more glamorous 8 millimeters of nail extending past your fingertip sound? Is that fair?" Kim asked me while arranging her tools and such on the table. I didn’t have any way to refuse her and to be honest I really didn’t understand the difference it was only four more millimeters. "Yes ma’am, thank you Miss Kim, I am sure that you know best," Was my quiet response. "You are so fun sissy! And look at the nail design that your friend selected for you, a pretty pink nail with little pink stones set at the base of the nail on the ring finger of each hand. They are going to look so sissy with the longer nail, and we will do what is called a ballet or coffin shape for the nail, so elegant," she told me while showing me an image on her phone. I was learning much more about nails that I had planned on. I had been thinking my toes looked silly in the pretty shoes that Mrs. Karen had me wearing without nail polish but I hadn’t put much thought into my finger nails. Painted toes were something that could be hidden but I guess none of that mattered now. Mrs. Karen had decided that I was going to be her sissy, publicly, and having long pink nails was no worse than being made to wear women’s clothes. With a soft sigh of resignation I relaxed and allowed Miss Kim to do her work. We chatted back and forth about things, and nothing in particular. I had been day dreaming just a bit when I heard Miss Kim’s voice, "Well Brie, what do you think?" Looking down at my hands I was in a bit of shock. Where before I could focus on them and still see a boys hands, fingers with short plain nails and a man’s wedding band, there were now long elegant fingers with shiny long pink nails. The effect was stunning, slimming, making my fingers and hands look completely feminine. I let out a little gasp of shock that got a huge smile from Miss Kim. "Sissy, what have you done?" Miss Anu asked me, standing behind me looking at my long nails. "Ma’am?" I asked questioningly, not fully understanding that I had done anything. "Your nails, why are they so long sweetie? I didn’t tell the nail technician to make them this long. I thought it would be too difficult for you to adjust to all at once." It sounded like I was being reprimanded. I looked at Miss Kim who returned my questioning looks with a stern glare. Defeated, knowing that Miss Kim was not going to take responsibility for choosing the longer nails I stared at my hands. "I am sorry Miss Anu, I said that longer nails would be nice and Miss Kim was kind enough to do them for me like this. It is my fault ma’am." "Well you are going to have to suffer until you learn to function with those talons little lady. Penny and your wife will not accept any excuses from you." Looking more closely at my hands and with a softer voice Anu added, "But I must say, on most women nails that long look a little garish, maybe even trashy, but on you they look elegant and feminine." In a lower voice so only her, Miss Kim and I could hear Anu said, "Can you imagine looking down and seeing those fingers wrapped around your little dick, if it was free of its prison, slowly stroking it up and down. The long pink nails, on your pretty little slender fingers rubbing in little circles, spreading your sissy pre-cum, getting you so close to exploding." "Ooohhhhhhhoooooo," I moaned, twitching my hips, my poor penis suffering inside the cage, trying to swell, the dildo shifting with every little pump of my hips. I could see the exact image that Miss Anu was describing and it was driving me wild. Now every time I looked at my nails all I would be able to think about would be watching those pretty nails wrapped around my little clittie. I began to pump my hips harder, trying to force the dildo in and out with more speed until I heard Anu shout. "Stop sissy, stop right now!" she scolded me. Blushing I stopped and glanced around, there were several ladies staring at me. I tried to get up and run out but Miss Anu stopped me and told me to sit down. Kim was staring at me, her mouth agape in shock. "What the hell was that all about?" she asked incredulously. Anu responded with a quite giggle and a smirk, "Oh, nothing much. It just seems that our sweet little sissy was a bad girl this morning and upset her mistress who had to punish her." "That's right Brie, you never did explain your punishment after I asked you. Instead you just continued changing the subject," Kim said, while pushing her finger against my chest. Glancing around I realized that there was quite an audience to our conversation since my ‘air humping’ episode. Mentally I just collapsed into myself, shrinking down into the manicure chair and staring at my new fingernails. I could hear Miss Anu’s voice but I did not have the courage to look up. In my mind I could see all of the women laughing at me, I could hear them laughing at me. "So evidently sweet sissy here threw a hissy fit this morning because her mistress had a pink jelly cock in sissy’s purse and she was embarrassed that anyone would see it. I can almost picture it now, maybe she even stomped her little feet to emphasize how serious she was but sissy demanded that the horrid pink penis be removed from her bag!" Anu told the ladies, her voice theatrical and full of energy. I could hear a few gasps and ‘oh my’ comments from the audience. Softly I began to weep, the shame too much to bear. "Please ma’am, please don’t do this to me," I whispered, but Anu continued with her narration. "So out of kindness and respect for her dear husband she removed it from sissy’s purse..." There was a dramatic pause while Anu let everyone think that this was the anti-climatic end to her story of my humiliation. "And she lubed it up and stuck it in sissy’s ass!" she finished with a flourish, eliciting gasps of astonishment and even a few applause from the women gathered around listening. "In fact, she still has it in as we speak. Her mistress was very clever, the way she has it held in allows the dong to slide and wiggle when sissy moves, that is why she started putting on her little show for you a few moments ago." I could almost feel Anu’s smile as she finished the story of my humiliation. I could feel my shoulders shaking as my crying intensified with the added humiliation, a couple of the women spoke out saying, ‘Work that shaft sissy!’ To be honest I didn’t care anymore. This was worse than the ladies at the mall making me wear lipstick. Everyone in the salon knew I was a sissy with a pink jelly cock up her butt and they had seen me try to get off using it. I was so ashamed because this had happened because I could not control my urges, I was the one who made a spectacle of humping and twerking in the salon for everyone to see. The rest of the salon visit, which thankfully was very short, I never looked up or took my face out of my hands. I felt Anu leading me out of the shop by my elbow as I stumbled blindly in my shame next to her. "Come along sissy, we need to get back to the office," she said while standing next to her car door waiting for me to open it. Which I did blindly, streaming tears. After sitting down and fastening the seat belt I just closed my eyes and tried to calm down. It was only a short drive before I felt her car slowing and turning, we couldn’t be back at the office yet, ‘to hell with it’ I thought to myself as I pressed my eyes shut even harder. "Brie, we are here honey, lets go," she told me, turning off the car and sitting patiently waiting for me to come around and open her door. I followed her in to the office, my head hung low, mascara a mess with red eyes from my uncontrolled sobbing at the salon. Walking Anu to her desk I thanked her for allow me to hold her purse, for lunch, and for my pretty new nails and knelt down, touching my forehead to her boots. With a pat to the top of my head and a little wiggle of my hair that was bobby pinned up she smiled. "You’re welcome sissy, we can do it again soon." I hastily returned to my desk, wanting to repair my makeup before anyone noticed and asked any questions. I was reaching for the large pink makeup bag when I heard footsteps come up behind me. "Brie, can you step into my office now please," Mrs. Penny asked. Then I heard her footsteps retreating as she walked back to her office. Setting the makeup bag back down with a sigh I turned and followed her back to her office. Entering I tried to keep looking down in a vain attempt to hide my disheveled appearance. Mrs. Penny sat down in her high back leather office chair and reclined back a bit, turning her attention to me. "Close the door and come over here please," she told me, indicating the chair directly in front of her large C-Shaped office desk. "Yes ma’am," I replied while softly closing the door to her office and rushing to sit as I had been told. Keeping my head down and my hands folded in my lap I waited in nervous silence. "What’s wrong Brie?" Penny asked, dipping her head to see my face. "Have you been crying?" "Yes ma’am, I’m sorry. It’s all my fault Mrs. Penny," I replied, trying not to get emotional again. "Okay, do you want to talk about it honey?" she asked in a warm voice, leaning forward, resting her arms on her desk. "No ma’am," I answered in a whisper. Pushing up against her desk and standing I watched in astonishment as she hiked her skirt up a bit and wiggled out of her panties, pulling them down and then stepping out of them as they slid to the floor. "Well sissy, as long as your makeup is a mess I suppose it won’t matter if you get it a bit more smudged," she told me while pointing to the cubby beneath her desk. I wasn’t sure what she wanted me to do so I remained seated, with a very confused look on my face. "Sissy, I want you under my desk right now. Mrs. Penny needs a little relief, it has been a stressful day and your darling wife has told me that you are very skilled in helping women relax." I was sitting in the chair with my mouth agape, totally shocked by what I had just heard. I couldn’t do that with another woman, that would be unfaithful to my wife. In a panic I dropped to my knees and brought my hands up in a begging position. "Please Mrs. Penny. I can’t be unfaithful to my wife, she is my entire world, everything to me. I could never do anything with another woman. Please ma’am!" I answered in a high pitched voice while in the process of freaking out. I couldn’t do this. Calmly penny lifted her phone off of her desk and dialed a number, putting it on speaker and placing it on the top of her desk. "Hello," I heard my wife’s beautiful voice coming through the phone speaker. "Hey Karen, this is Penny. Is this a good time to talk for you?" "Yea, sure, what’s up?" she asked. "First I want to complement your sweet husbands dedication to you and his absolute devotion," Penny spoke into the phone while twisting a lock of her hair around her fingers. I heard Mrs. Karen chuckle a bit. "Well thank you, and thank you sweetie for being so loyal and devoted. I think I know where this conversation is going though." "Yes, to be blunt I want this little tongue between my legs and she is begging me not to make her be unfaithful to you and I was hoping we could clear this up," Penny explained. I was shocked at the bluntness that she was telling Karen this. With a giggle Karen responded, "I don’t see any harm in that as long as Brie’s little cage is locked on nice and tight, you and the girls at the office have fun!" There was a slight pause and she continued, "Sweetie, don’t think of it as being unfaithful to me, think of it as living your dream to give pleasure and serve. I know that your heart and love is mine, it would be a shame to have such a pretty and talented sissy and not share her a little with my friends." Stunned to silence I lowered my begging hands and hung my head in shame, looking down at the long pink nails on my hands, the huge bow on my white and pink blouse, and the pink capris that encased my legs. Last Friday I was going out to a team work dinner with my wife and co- workers, three days later I found myself feminized, in chastity, on my knees in my bosses office being told by my wife that I have to service her orally. I could not even grasp how all of this had happened so quickly. Wordlessly I crawled under Mrs. Penny’s desk and turned to face her. She was still chatting on the phone with my wife when I gently began to work my face into her skirt. It was a snug fit and fairly dark so I could not see much, which made me feel a little better. As I got closer to her my lips and nose found her very hairy temple, unlike Mrs. Karen's neatly trimmed one. I had to wiggle my face to push past the mound of stiff, curly hair. The next thing that struck me as different was her smell. It was not unpleasant but it was much stronger, with a musky element that my wife did not have. Slowly I began to lick at her slit which was already very moist, almost soaking wet. I could hear some of the muffled conversation between her and my wife, this was so surreal. Penny tapped my gently on my back. "Go slow darling, we have all afternoon for this." Not lifting my mouth from her I mumbled, "Yes ma’am, thank you ma’am." And returned to my task. Locked in the dark folds of her skirt I continued to slowly nuzzle and lick at the outer folds of her lips, occasionally drifting up to lick or kiss at her clitoris. Throughout this time she took several phone calls and even had Anu walk in and ask a quick question while I continued to serve her in silence. As I continued she was becoming wetter, her feminine juices mingling with my sweat, makeup, and saliva creating a wondrous mess. With sore knees from prolonged kneeling, I began to wonder how long I had been down here? I had never done this for so long before but every time I would try to speed up or intensify her pleasure she would smack my back with a ruler and tell me that I did not have permission to change pace. I was so confused to be experiencing physical pain from my knees and back, emotional pain from orally servicing someone other than my wife, but also intense arousal and sexual pleasure. My mind was so scattered that I could not even begin to think straight, my wife would have told me ‘silly sissy, just concentrate on what you are doing,' so I closed my eyes and focused on the slow gentle pleasure I was giving Mrs. Penny. I began to try to slowly increase the level of stimulation without speeding up, concentrating on the inside edges of her lips. Soft tentative probes with my tongue to the inner folds, and sweet little sucking kisses to her clitoris. I began to be rewarded by the first soft moans from her and the slow pumping of her hips, very subtle but I could feel the shifting of her pelvis and I could taste the increasing wetness. In fact she was beginning to almost leak her nectar, which I greedily consumed to try and keep her dress and chair from becoming soaked. Even my own little caged clittie was beginning to leak and twerk in the confines of its prison. "Mmmmmm sissy, I was beginning to think that your wife was not a good judge of talent but now I see that she is right about you when you put your heart into your work. Keep that speed but see how much more you can do. Can you make your mean boss cum without going faster? I’m going to train you for your wife, when we are done you will be the most desired little tongue in this town," Mrs. Penny told me in-between soft moans, and little gasps. As stupid as it seems, hearing that lifted my spirits, she would help train me so I could be more pleasing to my darling Mrs. Karen! Now I began to concentrate, remembering the little things that I was doing with my mouth and tongue that would illicit a twitch or little gasp. I began stringing those movements together, gently weaving them into a tapestry of female pleasure. The aches in my knees and back disappeared and I began holding my breath for longer, my tongue, lips and teeth softly playing back and forth touching each erogenous spot in the special way that made her begin to quiver. "Ummmmm....fuuuuuukkkkkkk......it, it is so hard not to....to make you speed.....oh sppeeeedd up and finish.....almost agony but sssooooooo, mmmmm, sooooo good. Good ggirrllll ssisssyyyy," Penny stuttered. In my softest and most demure voice I spoke between licks to her I replied, "Thank you ma’am for letting a silly little sissy make you happy." As I spoke these words I began to press deeply, my face, nose and lips pushing gently but firmly deeper into her folds. Pushing my tongue in tight circles with ever depending precision, occasionally sucking in the excess juices we were making, then it began. Slowly at first I felt her monument begin to tremble, echoed by the tremors running through her hips and moving up and down her body. "Ooooouuuuuuuuuuuuuu!" The noise that I heard coming from above me was so primal and raw. Her voice raspy and deep. In shock I began swallowing what felt like waves of fluid, slightly musky, a bit salty but gushes and gushes of it. As I lapped and sucked Mrs. Penny’s gyrations became sharper and jerky. With a surprising suddenness if felt legs clamping against either side of my head with the force of a vice, unable to move I could only continue to swallow the endless torrent of liquid while also lapping at her soaked slit. The pressure from her thighs was incredible, between that, the dampness, and how deeply I had driven my face into her it was becoming impossible to get even a small breath. Feeling faint I began to panic but to no avail. My arms and hands were useless, if I tried lifting them I fell deeper into her, and I could not cry out. Slowly the feeling of sleepiness began to creep over me until at the last second Mrs. Penny relaxed. Sliding down, my face still inside her skirt, my lips touching a soaking wet tangle of hair, I sucked in a huge breath and collapsed into her lap. Not wanting to anger her I stayed still, knowing that she could tell me to continue. My breathing began to become more normal and I felt the tremors in Mrs. Penny’s thighs begin to subside. "Oh shit sissy, Let me be very clear," Mrs. Penny said, while continuing to breath heavily, "If Karen didn’t own you I would claim you for my own right now, and probably chain your pretty little ass under my desk every day." "Yes ma’am, thank you ma’am," I responded softly, still not moving. "Okay honey, you may come out from under my skirt after you have licked up any fluids from my thighs, but please don’t go near my cochie right now, she is too sensitive at the moment." Gently I took a few seconds to clean her and then slowly emerged from the tunnel of her skirt. The fresh air was wonderful. Looking up at Mrs. Penny I could see that her face was very flush but she was smiling. "Oh honey, you are a mess, I’m sorry," Mrs. Penny told me, reaching down to help me up from my knees, which was difficult because my thighs were cramping. "You were down there for quite a while but it just felt too lovely for me to let you stop." "It is fine Mrs. Penny, I don’t mind at all. I hope that my performance was okay for you ma’am," I whispered, looking up, my eyes bleary from sweat and her juices. With a broad smile Penny responded, "Oh you were more than just okay Brie, you were incredible. Between all of us in the office I am sure that you will get many opportunities to hone your skills too. Now what are we going to do about this?" she said pointing at my smeared face, wet hair, and disheveled blouse. "I can’t have you looking like this at the office or at dinner tonight." "I am sorry ma’am," I whispered, looking down at my crinkled, stained blouse. "I hope Mrs. Karen isn’t mad at me for messing up my clothes." "No...well, at least let me take care of that for you. I should have had you remove your blouse before beginning but to be honest, that has never happened like that to me before sweetie." "Mrs. Penny?" I asked, looking down in shame for what I was about to say. "I am sorry but I think I need to go to the restroom." She smiled. "That’s fine Brie, wash up a bit while you are there and by then I will have figured out something." Still looking down at the floor I whispered, "Ma’am I have to do something, but I can’t because I can’t take out something....I mean, I need to go poopie and I can’t. I don’t know what to do ma’am," I was blushing with embarrassment. I was having to ask my boss if I could pull the dildo out of my rear because I needed to do number two. Penny broke out with a short burst of laughter. "Well, I suppose that would be a problem wouldn’t it? You are right, I don’t think that your wife would approve of you removing that," she said while getting up out of her chair, straightening her skirt and reaching down for her silky tan panties. "Step closer sissy," she told me. I moved until I was standing in front of her. Reaching out Mrs. Penny took her panties and stuffed them down the front of my pants. "It wouldn’t be lady like for me to be walking around the office with my panties in my hands now would it? Be a lamb and grab my purse and let's go to the ladies room," she told me as I watched her walk out of her office and turn left towards the bathrooms. Following her into the bathroom I was nervous, this was the ladies room. I was confused, which bathroom should I use? I was a boy, kind of at least, but I was caged so I couldn’t do anything and I had to sit to pee. I looked like a woman, what was I? I was a sissy, what was a sissy? "Hold my purse open for me sissy," Mrs. Penny told me, breaking my chain of thought. As I held her purse out with the top open, she stirred around a bit and came out with a pair of latex gloves which she snapped onto her hands with a rather amused look. "Drop your pants and bend over," she said with a huge smile. "You know, that sounded pretty funny didn’t it sissy?" "Ma’am?" I asked in a bit of shock. "Take off your pants and bend over sissy. You are not allowed to remove things that have been placed there by a superior and that dick isn’t going to wish itself out of your ass. If you have to use the bathroom it is unhealthy to suppress that so bend over. Aunt Penny is going to pull it out of your bottom for you, isn’t that sweet?" Humiliated once again today I lowered my capri’s and then my panties, bending at the waist. I could feel the dildo slide out a couple of inches but then it stopped. Next I felt Penny’s gloved hand on my butt cheek and then the feeling of her ever so slowly pulling on the pink dildo. The sensation of it sliding out felt so good. Unconsciously I began to push back against her to get it to go back in so she could repeat the process. "Sissy! Stop that this instant!" Mrs. Penny scolded me. What I thought, then I realized that I was moving my hips, pumping the dong in and out of my butt. "I am sorry ma’am, I didn’t know I was doing that," I blurted out while focusing on staying absolutely still for her. Little beads of sweat were popping out on my forehead as the dildo was ever so slowly pulled from my butt, until with a little ‘pop’ it exited completely leaving me feeling a bit empty and almost sad. "All right, I am going to leave your butt toy in the sink, when you are done with your business I want you to wash that little pink dick very thoroughly and dry it with paper towels. You can fold your pants and blouse up and set them on the counter, leave your bra, panties, hose and shoes on. When your all done just hold my purse and stand with your nose in the corner and I will come by for you in a little bit. I need to find you something to wear." I did as told, stripping to my underwear and neatly folding my messed up clothing, placing it on the bathroom sink counter and then walked into one of the stalls. As I started to close the door Penny spoke up. "Leave the door open honey, sissy’s don’t get privacy, it encourages naughty behavior." Nodding my understanding I gingerly sat down to do my business, then got up, did the required cleaning at the sink, washed my hands and face, removing all of my messed up makeup and walked over to stand with my nose in the corner. Standing, staring at the white and pink tile, I began to get a bit upset, maybe a little mad. I hadn’t done anything wrong so why was I being punished I thought and punctuated my silent thought with a little stamp of my pretty pink sandal. For a brief moment I almost had the courage worked up to go confront Mrs. Penny but then I began thinking of why today had been so difficult and humiliating. It was because of the tantrum I threw this morning with my wife. With this thought in mind I calmed down, realizing the best thing to do was to be patient and wait for Mrs. Penny or another adult to come tell me what to do, and to obey them when they did. In retrospect I don’t think I waited that long before Anu came in and told me to gather my clothes and my now clean pink dong and follow her. I was nervous about walking out in only my panties and bra but had no choice. Thankfully she took me straight to Mrs. Penny’s office. Turning to leave Anu smiled, leaning over to give me a little kiss on the lips. "Brie, you know, you are even pretty without makeup." Sliding her hand across my abdomen to my panties she pulled them down allowing my little cage to pop out from behind my soiled maxi-pad. "Sorry honey, I just had to look because if I didn’t know better I would swear you were a girl and not a boy." Summoning up my courage I tore my eyes away from her hand near my little cage and looked up at her, meeting her gaze then quickly dropping my eyes a little, "I am not a boy Miss Anu, I am just a sissy," The words stung a little because I knew that they were true. "You are a sissy aren’t you, that makes things much simpler for me," she told me while pulling my panties back up and tucking my little prisoner away so there was no bulge. Then she wrapped her arms around me in a warm hug. "Don’t be sad Brie, you are the best sissy in the world and your job is to make people happy, that’s not so bad is it." Her voice was happy and light. She was right! I thought about how happy I had made Mrs. Penny, and how much fun Miss Kim had at the nail salon, and how I pleased my wife. It made me feel good that I had been able to make those ladies smile, laugh, or feel pleasure. With a timid smile, looking down at my pretty toes, hands clasped in front of me, I felt good for the first time today. "Thank you Miss Anu, thank you so much for not hating me or seeing me as a freak, you are such a wonderful person." The sound of someone clearing their throat came from behind us at the doorway of the office. Turning I saw Mrs. Penny. "Everything that Anu just told you is true Brie, you are a sweet person and I am happy to have you, not Brian, on my team," she said, holding out what looked to be a shiny black robe towards me. "This is all I could find here but it will cover you for the trip home. We are going to make one stop by my daughters house, you and her are about the same size so we should be able to find something for you to wear there. Oh, grab your big makeup bag so we can fix your face when we get to my house. I don’t think your wife would be happy with you like this, with no makeup." "Yes, ma’am, thank you." And I rushed out to grab my purse and makeup bag from my desk. The ride was very uneventful and Mrs. Penny even allowed me to wait in the car while she was at her sisters house. Reflecting on the day I began to realize that I had been the cause of all of my humiliation, that my mistress was forced to punish me for being so rude and insolent this morning. The funny thing about thinking back to each specific event was that as I did I would become excited, sexually. The knowledge that all of the ladies, people I had no idea who they were, knew of my secret was thrilling. Even the punishment of having to kiss Miss Anu’s pretty cheek while making the dildo pump in and out of me was something I could look back on and giggle about, but at the time both of these events were crushing to me emotionally. Sitting alone in Mrs. Penny’s car I vowed to be the best and most obedient sissy that I could be and to thank my wife and tell her how much I loved her as soon as I saw her tonight. I saw Mrs. Penny walking down the sidewalk from her daughters apartment building, she was carrying a fairly large bag that I assumed had some clothes for me to try on. I remained quiet, lost in my thoughts, for the rest of our trip to her house, which was a large brick home in a very nice neighborhood. I quickly hopped out of the car with my purse, makeup, Mrs. Penny’s purse, and the bag of clothes. Looking at the large wall clock it was just after four, so we had left work a bit early. I was amazed at the beautiful interior of Mrs. Penny’s home. It was so bright and airy, and immaculately clean. "Your home is beautiful," I told Mrs. Penny while looking around in wide eyed amazement. "Thank you Brie. Now follow me, you need to get cleaned up, made-up, and changed before your wife arrives. I have caterers coming any second now, if I show you to the bath can you manage on your own. I will come to help you select clothes and get dressed. I think this is going to be a very special evening for you sweetie," she told me while ushering me further into her home. She took me to one of her guest bathrooms, which was attached to a bedroom as part of a guest suite. "Okay Brie, you will find towels, soap, shampoo, and conditioner in there, I will lay out your undies and come back later with some clothes for you," she said while pushing me into the bathroom and closing the doors behind as she departed. ‘Special evening?’ What did she mean by that I thought. It made me nervous because here lately anything special seemed to involve me being punished or humiliated. This thought continued to run through my mind as I bathed. Drying off as I emerged from the walk in shower stall I saw that underclothes had been left for me. Wrapping the larger towel around my chest and then the smaller one around my hair I lifted up the bra first. It was a very pretty semi-longline baby pink underwire bra with demi cups and beautiful embroidery covering it and five hooks in the back. The straps were thin and dainty and the material was so smooth and silky, like nothing I had ever worn before. The g-string panties were matching in the same color with the same beautiful embroidery. How could I put my maxi-pad in these, there was hardly any gusset area. Sliding them on did make me feel incredibly sexy and they were stout enough to hold my little cage tucked so the bump was minimal. The next piece was a matching garter belt, the silky material sliding up to rest above the low waist line of my panties. This garter had two delicate suspenders per side, little more than slender pink ribbons. Rolling the light, dusky grey hose up my legs felt incredible, maybe even better than the hose my wife had put on me last Saturday night. These felt totally different and did not have a seam along the back at all. As I connected the delicate suspenders to the top of the hose I was amazed at the overall look and feel. Carefully I ran my hands down the length of my body feeling the pretty fabric that encased my skin. There was a knock at the door, I was so absorbed in my lingerie that I jumped and let out a little squeal as Mrs. Penny peeked around the door jam. With a smile she walked in. "Sorry if I scared you...ohhh my sissy! You look, delicious," she said, licking her lips and letting her eyes roam across my scantily clad body. "Thank you ma’am, these are the most beautiful and pretty feeling things I have ever worn or even touched. I can’t explain it but they are different," I told her, glancing down and seeing my long pink nails against my pin garter. Her finger tracing a line along the bottom of my bra Penny smiled. "I am very proud of you for noticing the difference Brie, these are handmade from a French boutique, the stockings are real silk too. You do them justice I must say." Blushing, but with a humble pride instead of humiliation I smiled, my cheeks rosy even without makeup, "Thank you Mrs. Penny, these are the most beautiful clothes, thank you so much for letting me borrow them ma’am." "No honey, not borrow, they are yours but every time you wear them I want you to remember tonight. Now, let's get you a little more dressed shall we. The caterers have everything under control so I can spend a bit of time with you if that’s okay." "Yes ma’am, thank you." "Have a seat, let's see what I can do with that hair," Penny told me as I sat on the small stool. She began running a brush through my damp hair, lifting it and then with a sigh she pulled out a set of hot curlers from beneath the counter. "Lets have some fun with this okay, you trust me don’t you Brie?" she asked sporting a very natural smile while fiddling with one of the rollers. "Yes ma’am, of course I trust you," I told her. Out came the curlers. After they had reached the correct temperature Penny used a round brush to select swaths of hair to wind tightly around the bristled rollers and then a clam-shell clamp was placed to keep everything together. I noticed that she worked from about one-third the way from my scalp down. As she continued working with my hair we chatted about fairly mundane things. I told her how much I was looking forward to working for her and promised that even thought I was a sissy I would still be the best engineer I could be for her. Reaching behind her I saw Mrs. Penny produce a large hair bow that was a perfect match for my lingerie set. With the rollers out now I felt her pulling the hair on the sides of my head back and then the click of the bows barrette, followed by her pulling out the curls and teasing them downward. "Mmmm, that looks very nice, now will you let me do your makeup too?" she asked, while opening up my large pink cosmetics bag. "Yes ma’am, you don’t have to spend all this time on me though, I can manage if you have something more important to do," I told her, worried that she needed to take care of other things. "Nonsense, now look up at me." And with that she began working on my face. When she was done I was forced to walk to be bedroom without looking in a mirror. Waiting on the bed for me was a linen dress in a light, dusty pink color, more subdued than baby pink. Mrs. Penny pulled it over my head and adjusted the scooped neckline which was made of layers of broad ruffles. The hem was quite high, stopping at mid thigh or a little above, barely hiding where my garters attached to the reinforced silk hose tops. On the bed were a pair of four inch stiletto heeled sandals in a tan color with small stones set on the narrow band that formed the vamp of the shoe and a delicate ankle strap. As I stood in my first pair of stiletto heeled shoes I felt wondrously feminine and for some reason even more submissive than normal. As Penny approached me I naturally bowed my head, averting my eyes. There was a tingle as I felt her fingers touch my neck. "Hold still, let me get this fixed," she whispered in my ear as she affixed a triple strand of pearls that fit tightly against my throat and added a gorgeous David Yurman white gold cuff to my wrist. With a gasp I reached up to my throat and then marbled at the beautiful white gold cuff bracelet. I had never, even as a man, owned any real jewelry. "Now, those are just on loan sissy so don’t get any ideas," Penny told me with a laugh. "You can look now," she said, turning me to face a full length dressing mirror. "I think that you will be the most beautiful person here tonight sissy." Pulling in a sharp breath I was stunned at the reflection that greeted me in the mirror. Bringing my hands up to smooth out my dress a bit I turned to Penny. "I don’t know how to thank you ma’am. I think that my wife is going to be very pleased, at least I hope so." "Brie, I don’t see how she could be anything other than enchanted with you, please be on your best sissy behavior tonight. Don’t mess up what could be one of the best, most memorable nights of your life," she told me while making a minor adjustment to my hair. There was that warning again, Penny had told me it would be a ‘special evening’ and just now I had been warned it would be ‘one of the most memorable moments of my life.’ I had butterflies in my stomach just thinking about it. "Mrs. Penny ma’am, can I ask you a question?" I queried tentatively. "Sure Brie, what is your question?" "I am scared, what is going to happen to me tonight?" My voice was shaking and so were my knees. Penny sat down on the edge of the bed and patted the spot next to her with her hand, moving slowly, feeling the sway of my hips over my new heels, I made my way to her and, as ladylike as possible, sat where she had indicated. "Sweet Brie, just for tonight don’t be afraid, just relax and let yourself go with the evening. If you continue to be your submissive, demure self you have nothing to worry about. I guess what I am trying to say is, I can’t tell you more about what could happen tonight but I can promise that if you will be your sissy self and not do anything silly, that everything will be just fine," To emphasize her point she put her hand on my thigh in a reassuring gesture. It had been a while since Mrs. Penny had left me in the bedroom, telling me to stay put until she sent for me. I could hear distant voices and looking at my phone I saw that it was almost seven so the dinner party would have already started. Had she forgotten about me, should I text her or Mrs. Karen? I was getting more nervous as time passed and the butterflies in my stomach continued to flutter around, maybe I was just a little hungry. As I became more unsettled I recalled the last words that Mrs. Penny spoke to me, ‘continue to be your submissive, demure self’. I used this as a mantra to calm my beating heart, which seemed to be working until I literally jumped off the bed when someone knocked on the bedroom door. "Yes, who is it," I called out in a meek voice. The door knob began to turn, and then the door slowly swung open, it was Mrs. Penny. "Brie, are you ready to join us?" she asked. "Yes ma’am," I said, raising off the bed and reaching for my large Dooney bag. "No, honey, it’s okay tonight, just leave your bag in here." I followed her down the hall towards the sound of voices, laughter and clinking glasses. As we rounded the corner I saw Miss Anu, Miss Amber, another woman I had never met, and a tall dark haired man I had never seen before. There was also a waiter with a tray of champagne crossing the room and at the far end I saw my beautiful wife. Mrs. Karen was wearing a simple black sheath dress with a square neck line that showed the beginning cleft of her breast, a single strand of pearls dipping towards her plunging part. Black stiletto pumps with the ever-present ankle chain that held my chastity key graced her sexy legs. Seeing her took my breath away. It seemed like I had been apart from her for an eternity even thought it had only been a day. Fighting the urge to run to her I remembered Mrs. Penny’s words and tried to remain calm as I walked across the floor towards her. As I strode forward it seemed that all of the noise died down. My face flush with embarrassment as I glanced around seeing that everyone was watching me. What had I done, was something wrong, did they know I was a sissy? Karen had glanced up casually in my direction but then in a flash of recognition I saw her expression change from one of mild curiosity to one of what appeared to be shock. ‘Shit!’ I thought to myself, ‘she thinks I am a freak with my long pink nails, she didn’t give me approval for that, I have gone too far.’ In an effort to not break down from the pressure of everyone looking at me and the disapproving looks of my wife I purposely unfocused my eyes and continued my slow walk towards her. She had told me that no matter what she would still love me, I had to believe in that. When I reached her she still regarded me with an awkward and wordless stare. Slowly sinking to my knees in front of her I lowered my head to her beautiful feet and placed a gentle kiss on the exposed toe of each of her feet. "Mrs. Karen, I am so sorry for my behavior this morning but most of all I am sorry that I upset you. Can you please forgive a stupid sissy who is just trying to learn how to be better for her mistress?" I think the words all came out and I hope that I had not been so quiet that she couldn’t hear me. I could feel the blood rushing to my head, my heart beat pounding in my ears. I knew that there were others watching and with a flash of terror I thought, ‘did I just embarrass my wife with that display?’ But it was too late to worry about that now. I just stayed on my knees, my eyes focused on her pretty silver nails. In my blurred vision I could see her knees bending down and I felt her hand on my cheek, lifting my face gently up. The vision that I was graced with was my beautiful wife, her eyes glistening with the moisture from fresh tears and a sweet smile, looking down at me. "Brie, yes. Yes I forgive you, I forgave you the instant that it happened my love. There was never anything to forgive," she said while holding out a small black box. I was trying not to cry, I didn’t want to mess up all the work Mrs. Penny did for my makeup but it was hard to hold back the tears. "I love you ma’am." Where the only words I could muster without breaking apart. Silently, like a magician revealing the secret of her greatest trick, Karen opened the small box. Sitting nestled on a dark purple bed of velvet was a ring, a white gold band that twisted to hold a single diamond in the center with a smaller diamond on either side. This was an engagement ring. There was a rustle of fabric as Karen lowered herself down onto her knees, even with me. Looking me straight in the eyes she smiled, pulling the ring out of its velvet bed. "Brie, thought I know we are already husband and wife we are so much more now. You have given everything to me, without regrets I hope, I want to give you this...this symbol of my commitment to our love which is forever. I want us to renew our vows, but this time as mistress and sissy, a bond that can never be torn apart." I was crying and trying to say yes but the words just wouldn’t come out so instead I wrapped my arms around her in the biggest hug ever while nodding and bobbing my head like an idiot. Taking my hand in hers I watched as she slid the beautiful engagement ring past my long pink nail onto my finger. "Brie, will you forever be my sissy?"