Crowd Sourced Sissy free porn video

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Crowd Sourced Sissy If you were to ask my friends a year ago, they probably would have told you that I had a pretty sweet life. As an account manager for a high-end hotel chain, not only was I making a pretty good salary, but I also got to travel the world and stay in any of our fabulous hotels. I was a single guy with a healthy libido and money to burn who was known for taking several vacations a year. Some of them were business trips, but most of them were just for fun. That changed a year ago, just before the world shut down. I had been partying with my friends in New York City for a few days, but one night I decided to head out by myself and hit a late-night cabaret that had a reputation as a pick up spot for kinky people. I was looking for an adventure. I had only been sitting at the bar for a few minutes when a gorgeous redhead plopped down on the stool next to me. She gave me a seductive smile and told me that her name was Sophia. "Sophia the escort," I thought to myself. She was far too pretty to be a normal Nancy hitting on a guy in a bar. So I smiled and gave her a fake name. "Hi, I'm Michael," I lied. "Lovely to meet you." After a couple of drinks and a little chitchat, Sophia leaned over and whispered that we should go somewhere private. Now I'm not opposed to taking a prostitute back to my hotel, especially one who looked as good as Sophia, but I wanted to know how much a night with her was going to cost me? I didn't have to ask. She brazenly reached over and gave my crotch a squeeze. "I'm not an escort," she said with another squeeze. "Well, not in the usual sense. I have a website where subscribers pay me to make sexy videos and you look like you might be down for some fun." I asked her what type of videos and she explained, for example, that tonight's entertainment might involve her going out and seducing some random guy, taking him home, turning on the web cameras and fucking him like a bitch in heat. "There will hundreds of people watching me give you the best fuck of your life," she said with a seductive grin. "If you're into really kinky games, maybe even thousands." I was a little worried about showing my face, but Sophia pulled a little black mask out or her purse and explained that she could protect my identity. That's all I needed to hear. I closed my tab and took Sophia back to my hotel. I was so excited that I barely noticed the doorman give Sophia a wink as we entered the hotel lobby. We were alone on the elevator, so Sophia guided my hands to her tits and backed up to rub her fabulous ass over my crotch. She was moaning out loud by the time the elevator reached the 28th floor. I swear you could smell the pure sex coming out of her pores by the time the door opened. I couldn't get her into my room fast enough! She handed me her phone and told me to record everything as she dropped to her knees in front of me. "Hi guys," she said with a wicked gleam in her eyes, "as promised, I went out and found somebody new to play with." I had trouble holding the phone steady as she unzipped my fly. She giggled like a little girl at Christmas as she pulled my hard cock out of my pants. "Yum," she purred. "I love a big cock full of delicious cum." She devoured my cock, swallowing me to the hilt with one practiced motion and used her tongue to get me fully hard. Then she began bobbing up and down, effortlessly taking me to the point of no return. She stopped only long enough to take back her phone from me. Keeping it trained on her face she said, "My fans love it when I get face-fucked! The harder the better!" Sensing my confusion, she explained, "My favorite was this one time where a guy fucked me so hard that he split my lip--do you think you could do something like that for me?" She pouted her lips for me (and the phone) and said "pwease." I didn't want to disappoint the poor girl. Bunching her hair into pigtails, I began ramming into her mouth with all my strength. Sophia moaned in appreciation, so I took her to the ground and let gravity help out with my thrusts. I was too consumed with lust to care if I was hurting her or not, although she continued to keep her phone pointed at her face, so I deduced that this is what she wanted. I gave it to her as hard as I could, which sadly meant that I didn't last very long. I stiffened and shot my first load of the night straight down her throat. When I watched the video later, I'm ashamed to say that I had only lasted 78 seconds. Sophia didn't care. I had ruined her makeup and given her a bloody nose, but she still had a look of sheer lust in her eyes. "One load down," she said to the camera as she blew her fans an air kiss. "Let me know what you want to see for round two." She stopped recording and uploaded the video. "Thanks," she chirped as she suddenly popped up and went into the bathroom. "Think you can go again in 30 minutes?" I said yes, but I don't know if she heard it as her attention was now focused on her phone. After a few minutes it started beeping and buzzing non-stop. "You're a hit, babe," she called out from the toilet. "Ooh," she giggled, "some of my fans have some sick ideas about what you should do to me next." She came out into the room a few minutes later wearing nothing but a bra and panties, stocking and heels. My eyes immediately went to the bulge in her panties. She laughed as she saw me, open mouthed and unable to talk. "Oh yeah," she shrugged. "I used to be a guy. I hope you're okay with that." She cocked her hip and added," nobody thinks I'm a guy now." She was right. Sophia was as hot as any porn star, and I told her so, but I did have a few questions. Sophia took me into bed and told me her story; all while she ground her ass into me and had me play with her nipples. Once upon a time, it turns out, Sophia had been Sean, an out of work actor who was bisexual and so he would occasionally make his rent by dressing up like a girl and meeting businessmen on Craigslist who were interested in meeting a no holds barred sissy whore. She giggled and explained, "In my case, it was no 'holes' barred." She eventually caught the attention of a hotel manager who threatened to call the police. "Unless," he'd explained, "you want to join our special concierge program." There were twenty or so hotels in the city where the staff would look the other way, and even help hook a sissy whore up with their preferred clients. Sean would be safe and protected if he agreed to work for the hotel, but he would have to share his "tips" and serve the hotel staff on occasion. Desperate to make his rent yet again, Sean had agreed. The hotel had him officially apply for a job as one of the housekeeping staff. He would receive a full salary and benefits, and would only be expected to show up a few times each week and "clean" a few cocks. But there was a dress code, so Sean was instructed to go to a beauty shop in the Bronx for his first day of training. Sean went into the shop as a nervous young man, but came out as a very pretty woman. He was given a drink to help him relax. It was drugged, and Sean was barely conscious when he was put into the beauty chair. Headphones were placed on his head and Sean began his first of many hypnotic-training sessions. When he awoke several hours later, the girls at the shop had given him long blonde hair extensions and a full set of fire engine red fingernails. They did his makeup with semi-permanent cosmetics and started teaching him how to make himself pretty on his own. They glued on a set of D cup breast forms and used latex to hide the seams. He was then locked into a severe corset that took his figure down to something far more womanly. Sean was proud that he now had a 33" waist, but the ladies explained that he still needed to lose at least 10". The final step happened so quickly that Sean didn't know what was happening until it was too late to stop it. He suddenly found his cock surrounded by a hard steel cage. It was a tiny chastity device that only allowed his cock to poke out ?" at the most--ensuring that he would never mess up his new work uniforms with an unsightly bulge. A steal cable belt was added to keep everything nice and tight. Sean tried to protest, but found out that the hotel manager held the only key to his cage. "If you're a good girl," one of the women explained, "I'm sure he'll let you out on occasion for a sissygasm." When he still protested, the stylist said something discreetly into his ear and Sean was suddenly filled with the need to obey her. It was the first of her sissy triggers. It wasn't very strong yet, but it was enough to make Sean desperate to do whatever these women commanded. Sophia guided my hand down into her panties at this point in her story so I could finger the tiny cage that surrounded what was left of her manhood. There wasn't much left. Sophia took me back to the beauty shop with her story. Seamed stocking and a garter came next, followed by 4" beginner heels that were locked in place. The ladies helped Sean over to a mirror and smiled at their new creation. "Chica, you're going to be beautiful," they gushed. A van came to collect Sean and deliver him to the hotel. The hypnotic suggestions were still active. He was given some employment papers to sign, one of which was an official petition for a name change. And thus Sean the struggling actor ceased to exist. She was now "Sophia Cunningham," a maid working for the hotel. Sophia found that she was expected to clean hotel rooms each day, but also found that the guests frequently returned while she was doing her "job." Predictably, she would quickly find herself thrown across the bed and being fucked by the guest. Sophia would moan like the appreciative whore that she was becoming, although she would pout when she had to make the bed all over again after the guests had used her. The hotel took a substantial cut of her earnings, but even so, Sophia was thrilled to find her bank account growing. What's more, the hotel kept an "advancement account" for her, which was eventually used to pay for breast and hip augmentation as well as facial feminization surgeries. Within the year, thanks to continual hypnosis training sessions and non- stop corset training and all of those surgeries, Sophia had become one of the most requested features of the concierge program. "Those were the days," she mused. "I would get fucked eight or nine times a day." I felt Sophia's little cage twitch at the memory. Her story was interrupted by a loud knock at the door. "Sir," a deep voice called out. "Hotel staff. Please open up." Sophia gave me a quick squeeze to tell me that it was okay. I opened the door to find the doorman standing there, along with one of the hotel guests. They didn't wait for my invitation, barging into the room as if it was their own. I was a little shocked until Sophia popped up and gave the doorman a big kiss. "Hey girl," he said. "I saw your video and thought you might like a little help making a new one." Sophia clapped her hands in approval. "I was reading those comments," the doorman continued. "You've got some pretty sick fans, but I'm game." A shudder ran through her body and she all but begged him to do anything her wanted to do to her. The hotel guest got a strange look on his face. I was a little concerned, but Sophia started trembling in anticipation of what was to come. Sophia handed me her phone and gave me a deep kiss. She asked me to please film everything, and to not stop recording no matter what happened. I was a little overwhelmed by what was happening, but I agreed. The doorman and the hotel guest put on masks, and then he leaned in and whispered something into Sophia's ear. A physical change rippled through her body. She fell to the ground, and when she next looked up, she was something feral. She whimpered in her need to be fucked. I recorded everything. I recorded as the doorman dragged Sophia across the room by her hair and threw her across the bed. I recorded as he fucked her mouth while the other man took the desk lamp and proceeded to fuck her sissy hole. I was worried that the light bulb that was now being shoved in and out or her ass would break, but Sophia was moaning in so much pleasure so I kept recording. What's more, I was turned on and wanted to join in the action. I had a close up on Sophia's face when the doorman filled her mouth with his cum. The other man was next, although he pulled out and shot his load directly into her nostrils, so Sophia had to snort down his cum. They looked over at me and I found myself handing over the camera and joining in the fun. I fucked her face once again, and this time I lasted for several minutes before giving Sophia her fourth load if the night. No sooner had I cum than the doorman handed me back the phone and proceeded to start pissing directly into her mouth. She swallowed his entire stream without spilling a drop. The other man had taken the desk lamp out of her ass and replaced it with his own cock, which was now filling her bowels with his own stream of hot piss. Throughout all of this, Sophia moaned and writhed as if it was the most enjoyable sexual experience of her life. I understood that it was the hypnosis training, but I was turned on at the thought of somebody enjoying being degraded so much. Somewhere deep inside I wondered if it was something that I might enjoy as well. I found myself handing over the phone and crawling over to Sophia. I kissed her and licked the residue cum and piss off her face. I wasn't wearing a mask. I knew I was being filmed. I didn't care. We fell into bed, kissing and fondling each other like horny teenagers. The doorman kept filming it all. At one point he handed over the phone and stepped forward, his hard cock jutting out and demanding attention. I'm not sure what possessed me, but I lunged toward him and started sucking his cock while Sophia turned her attention to his balls. I vaguely recall hearing a knock at the door. I was too wrapped up with Sophia to notice anything until I suddenly realized that there were four men in the room. One of the new guys stepped forward and began fucking my face. Even if I had some second thoughts at this point, I was helpless to resist the assault on my throat. Before I knew what was happening, I felt him shoot his hot cum down my throat. The doorman was right there with the camera; What's more, he had fished my driver's license out of my wallet and was holding it up next to my face. I wasn't wearing a mask and I had a mouth full of cum. "I think we found ourselves a new sissy," he narrated for the video. I knew in my heart that this was a transformative moment. I knew in my heart that I didn't care. I looked straight into the camera and licked my lips and said, "Yes, sir. I want to be a sissy cock slut like Sophia." The doorman stopped recording and gave me a look that asked if I really wanted to have him post that video. I was so overwhelmed with desire that I nodded my head and said yes. To prove my point, I crawled forward and started to suck the doorman's cock, knowing full well that it was all being recorded. That's the moment that my life started to change in earnest. Later that we lay in bed languidly pushing dildos in and out of our sissy pussies. As we scrolled through the comments on her website, I was once again overwhelmed by my desire to join Sophia in her life as a sissy whore. I knew that it was my last night in the city, but we were already making plans to take things further the next time I came to town. Unfortunately, everything would change a few days later when the pandemic really took hold and after a month, I was furloughed from my job. Sophia and I kept in touch via my webcam, and she helped me find a beginners sissy outfit, but it wasn't as all consuming an experience as I had hoped. And the truth of the matter was that I had to start worrying about money. That was right up until Sophia came up with a plan that would change my life. She posted a video to her page. It began with a close up of a black rubber dildo mounted to a chair. She stepped into frame and positioned herself above the dildo, blew a kiss to the camera, and then dropped full force down into the seat. "Hi guys!" she said with a bubbly, schoolgirl voice. "I have a friend who needs some help. "Remember that guy I met a couple of months ago? The one who said that he wanted to be a sissy like me? Do you want to help make it come true?" A mischievous look came into her eyes. "She needs a sponsor. Some guys who will be in charge of her transformation from boring office guy to fabulous sissy! She will quit her job and move to New York, and then do whatever you tell her to do!" I saw a shudder run through her body as the words came out of her mouth. "You would get to decide how she gets trained," she continued. "Want to hypnotize her so that she can't eat any food except for cum and piss and poop--that's up to you. What surgeries do you want her to have? Giant tits, ass implants, permanent cocksucker lips? You decide. You paying, so you can make her look and do anything at all." "All you have to do is be her sponsor," she giggled. "We'll put the whole thing here online. You'll get a front row seat for when she is forced to spend the night in jail, or in the kennels. Maybe even a close up when we chop off her ugly sissy balls. It's your call. Sponsor her at the link below and let's see what a crowd-sourced sissy looks like." This was all posted on her page, along with the link to my new page. I noticed that there were a lot of comments on the video. Horny, kinky-as- fuck men and women who said that they would pay to help turn me into the world's biggest sissy whore. I should have been terrified, but I was rock hard. Well, as rock hard as I could be while locked in my little chastity. Sophia kept the only key safe and sound with her, Clicking over to my new page, I saw that the only video was the doorman's video of my first night. I knew that couldn't stand. I pulled out my phone and stripped naked, except for my panties and chastity. "Hi guys," I said in my newest video. "Thank you so much for wanting to help make my sissy dreams come true. If you will be my sponsor, I will obey your every command, no matter how kinky." "Please," I finished, "Make me into a sissy cock slut." I sent the video to Sophia and asked her to post it for me. Then I started dragging my belongings out to the dumpster as I started making plans to throw away my life and move to New York--The city where naughty dreams can come true! AUTHOR'S NOTE. I hope you like this idea--I get deeper into her transformation in part two. Leave a comment if you like where this is going or if you have any ideas you'd like to see in part 2. Or, feel free to email me at [email protected]. xoxox Emshoninque, aka Sissy Michelle

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4 years ago
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Sunday Night Football Sissy

Sunday Night Football Sissy It's no surprise that we love football here in Texas. We all head out to watch high school ball on Friday nights, and of course we love to cheer on our college boys on Saturdays. And the grown men dominate our Sundays. Especially if you're a sissy slut like me. I am a sissy cock slut who happily serves a small group of men here in town, and things took an interesting turn a few years back when I learned that Master David was an avid Cowboys fan, while...

2 years ago
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Teaching the Sissy Maid Workshop at the MVP Chapter Three Daisy Begins Her New Life as a Sissy

Teaching the Sissy Maid Workshop at the MVP, Chapter Three Daisy Begins Her New Life as a Sissy Maid She took and held three enema bags before I allowed her to get out of the tub and she was emotionally, sexually, mentally, and physically broken. Not permanently, that takes years to accomplish, but she had given up and began the process of accepting that she was powerless and too weak to resist me. To keep her in the right frame of mind, I grabbed her by her hair and walked her...

2 years ago
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A Happy Sissy

A Happy Sissy Kathleen didn't iron. Janelle wouldn't work past noon. Hannah wanted too much money. Damn, good help was hard to find. Monica, my wife, sat on the bed with the newspaper ads spread around her. She was looking for a maid. The way she tells it, Sharon had been a domestic with her family for a thousand years. As Monica grew up, Sharon was always there to advise her, to steer her toward decency, to make sure she knew that hard work was the key to good results....

2 years ago
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The Blushing Sissy

The Blushing Sissy by StateRowdy [email protected] ? She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties down...

2 years ago
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Degraded Sissy

fondamaid asked: Hi. Sorry it's been a while. I haven't dressed and I felt a little odd sending you a note while in men's clothing. Today I'm dresses, corseted, and locked up. I'm just not sure how long I'll keep myself locked up. I did finally get baby oil to use though and the cage is more comfortable because of it. I thought lube would work fine, but I was wrong. Now I'm all sissied up and wondering what I should do. Part of me thinks I should practice pleasing real men.I hope that, when you...

2 years ago
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How to Build a Better Sissy

How to Build a Better Sissy Or My Evolution by: Missy Satinpanties I was a small, skinny child, with a rather normal family. My father worked for the electric company as an auditor, and my mother ran a yoga studio in the converted garage of our home. When I was young, this was where I played, watching women contort themselves into the various yoga poses. I was about 6 when I asked my mother...

4 years ago
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Checkerboard Sissy

Checkerboard Sissy By Cassandra Morgan A guy never wants to meet his girlfriend's parents for the first time. There are always years to negotiate, and beliefs, and backgrounds. As nice as the parents may be, there are always judgments to make, and old boyfriends and girlfriends to reference, and finances to be probed. It is natural to be suspicious of someone who loves your child. For Keisha and I, this was more challenging than for most couples. As an interracial couple, Keisha...

4 years ago
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Trucker Daddy Gets A Sissy

It could easily be the lowest point in Denny life, sitting in an old Ford Escort that wouldn't start, the temperature outside well below freezing and him not having the cash for a hotel or to have the car fixed. He had no idea what to do next. Completely out of ideas, he had been sitting in for hours watching the normal people with money coming in and out of the Flying J Truckstop. He almost jumped out of his skin when someone knocked on the window. Denny cautiously rolled the...

2 years ago
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Saturday Night Sissy

SATURDAY NIGHT SISSY by Throne I spend all week, every week, dreading Saturday. My wife Alana met Dutch several months ago. I knew my bride had a past as a party girl, and that she still flirted with men. Male eyes always went to her, a tall girl with a stunning figure -- big bust, tapering waist, flaring hips, full thighs and, most of all, a plus-size bottom that sticks way out and moves like it's on springs. Dutch was the kind of guy she used to date -- big, rough, uncouth. The...

3 years ago
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The Blushing Sissy

Story writing contest 10 [email protected] She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties...

3 years ago
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Home Alone Sissy

What is it they say, "It all began like any normal day." Well since I was wearing a sissy maids uniform it was not going to be a normal day! I had on black patent leather Mary Jane shoes, with four inch heels. I love higher because it forces me to walk more daintily but I had a full list of chores and would be on my feet all day, so practical is better. My legs are encased in shear black stockings, of course they have to be stockings, tights just do not do it for me. They have a...

4 years ago
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Be a Sissy

forced to be a Sissy IThe young man stood facing a very large woman sitting in an upholsteredarmchair. There was no other way to describe her. She was fat, perhaps,pushing 300 pounds he thought. The way she was staring at his punyframe suggested that maybe he was going to be her next meal. She wasn'tsaying anything as she visually appraised him for the first time...Jacob had been brought to this woman by his step-grandmother earlierthat morning. He had been given over to his step-grandmother by...

3 years ago
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Sissy On Sissy

SISSY ON SISSY by Throne Bob stood there feeling beyond foolish. His body had been denuded of hair and his skin, after weeks of using an imported emollient, was satiny. All he had on was a pair of bikini-cut panties and a training bra. He was wearing the latter because his wife, Tessa, had taken him to a specialist two weeks before and gotten him a lovely set of breasts. They were small implants and his nipples rode high on their feminine curvature. It didn't provide any modesty...

2 years ago
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Mrs Grant and her new Sissy

New Little Sissy"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was...

3 years ago
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New Little Sissy

"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was attracted to...

2 years ago
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Its Hard For This Sissy

IT'S HARD FOR THIS SISSY by Throne Pete had just gotten home from work and he immediately noticed a look of mischief in his wife Andi's pale blue eyes. He seen that all too often in the past. She must have spotted the concern on his face because she wanted to know, "Is something the matter, Petey?" She was calling him by the diminutive of his name. The switch from Pete to Petey was another bad sign. "It's just..." he extemporized, "that you seem... distracted." "Well,...

4 years ago
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stepson becomes moms sissy

Mark Peters let out a low moan that couldn’t be heard above the organ as it played "Here Comes the Bride." Although every other head in the church turned to glimpse the tall, dark-haired beauty imperiously making her way down the aisle, Mark kept his eyes fixed on his feet. Had anyone been paying attention, they would have seen a small tear escape Mark’s eye.It seemed like only yesterday that Mark’s mother and father had split up. Mark’s dad, Mark Senior, was a partner in one of the city’s...

1 year ago
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My Sisters Sissy

My Sister's Sissy By: Missy Satinpanties Note: This isn't one of my usual stories of sexual degradation, but what I think of as "my autobiography that should-have-been." The make- up of my family is the same as it was, my sister's names are the same, but that's about it. This is how I wish things would have gone when my little secret got "out of the bag." I guess I've always been a sissy. I remember playing dress-up with my sister when I was very young, and can vividly remember...

3 years ago
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A Nasty Daddy gets a Naughty Sissy

I came out of the bedroom dressed in my too-short pantyshowing Pink Shorty dress, pretty anklets, black MJ's, pink panties, red lipsticked lips and with my cute cuff and collar set on, awaiting Daddy's padlock, which would begin the playtime for real. This Daddy I had run across on a website was one who loved forcing sissies to literally mess their panties while they were in bondage so he could then go on to the diapering and teasing them for being such bad baby girlie sissies. Me,...

4 years ago
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Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

4 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

1 year ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy.Sissies are...

2 years ago
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Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

3 years ago
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Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

1 year ago
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Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

2 years ago
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The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

2 years ago
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First time Sissy

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any stretch of the imagination but cannot talk about it because of "rules". I had become a "male cheerleader" but was finer than some of the bitches there and had the...

Transsexual
3 years ago
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Im Not A Sissy

I'M NOT A SISSY by Throne My name is Joe and not Jodie. I'm an adult and not a kid. And I'm a man and not a simpering sissy. I keep telling myself that. But my wife Arianna thinks differently. I mean, ever since we got married two years ago she had been running my life more and more. Talking down to me. Turning me into her sex slave in the bedroom, demanding oral attentions and giving almost nothing in return. She mocked my small penis and made me masturbate while she watched....

2 years ago
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Richard the Sissy

Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a...

3 years ago
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The Lingerie Salesman Sissy

I had a career change a few years ago. Admittedly a door to door salesman did not sound good but the money was OK as long as I made plenty of commission but the fringe benefits were amazing. For me it was not household cleaners or insurance but sexy lingerie. Not only did the ladies on my round like to try on the lingerie but as soon as they felt super sexy I would get my “extra” commission. Yes I had all shapes, sizes and ages, even a mother and her daughter were regular customers and I had...

4 years ago
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son turned into moms sissy

My name is Barbie. Everyone calls me Barbie because I am small and I have long blond hair. I am the smallest in my class. My real name is Ashley. Before you ask, I do not like Barbie's. I never played with them. I suppose when you have hair down to your shoulders, then people think you look like a girl and call you Barbie. I am eleven years old.I got this diary today. So I might as well write in it. It is a purple one with a bear and heart on the cover. It has a lock on it. I might as well use...

3 years ago
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Cum Craved Sissy

Taking a quick look at the clock, I noticed that the delivery had run late, and I was immediately stressed at the fact that Mistress would be home shortly. I knew I didn't have time to shower, and there was certainly no time for much cleanup either. I just pealed the skin-tight jeans down, crumpled them up and buried them at the bottom of the hamper.I carefully pulled the bright yellow panties down my legs, trying not to make any more mess. I washed the creamy jism away in the sink, squeezed...

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