Melissa's Sissy Boifriend free porn video

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The week before my state college's winter break I was eating in our lunch hall reading one of my magazines when a loud and commanding female voice asked, "Is anyone sitting here?" I quickly looked up and my heart rate skyrocketed upwards when I realized that it was Melissa the meanest girl from my high school. To say that this girl is mean is in my mind at least, an understatement. I can still remember the first week she came to our small Northern Virginia high school from NY, she beat up any guy or girl who got in her way. During one very bad fight several of the resident mean girls jumped her after school, Melissa not only beat the crap out of the other ice princesses, but also the first couple of teachers who tried to break up the fight. No one messed with her after that! Not long after she had exerted her dominance at our high school, we quickly learned that she could hit you with her words, just as hard as she could with her fists. I have been interested in femdom since high school so she was in many of my high school fantasies. "Hello?! I am talking to your dumbass!" She barked and handed me a napkin and told me to wipe her a clean area on the table. "I would like for you to help me with my stupid calculus class, you somehow understand that crap." Melissa said as she sat down. "My last class is at 4pm today and I can be at your place soon after," I stammered. "Come over around 6pm, and what the hell are you eating?! You are not in good enough shape for pizza, god men are such morons!" She picked up my entire tray and threw my food in the trash. "Go get a salad, and do not use any other dressing other than oil and vinegar." Right at six o clock I was at her door. We studied late into the night. The next day she came over to my dorm room, and started to look around. "Uh yah, this needs to go," she said as she started to rip my Sports Illustrated swimsuit model posters off the wall. "Don't worry I will bring over some tasteful posters." She then started to go through my drawers and my heart rate leapt into my throat as she pulled out my pairs of flowery panties. She glared at me, "What are you gay or something?" I explained that I wasn't gay and just liked to wear panties sometimes to get a thrill from knowing that other students didn't know what naughty undergarments I was wearing under my trousers. "Interesting, very interesting," was all she said as she went back to digging through my drawers finding more panties, bras, and pantyhose. "Um," I said not wanting to interrupt, "I, I have to go to my history class." "Great, I can't make that class today, this room needs some serious work. Take very good notes for me or I will beat the crap out of you," she barked. I instantly started to get a stiffy from her verbal abuse. Melissa looked at my crotch and laughed, "Yup, I figured you liked that stuff, otherwise you would have run the other way the second you saw me, correct?! You better get to class now!!" she said with even more authority than before. All through history class I struggled to pay attention. I couldn't help thinking about what could be my greatest dream come true. I just hoped that I could handle actually being a subservient in a dominant relationship. Would I chicken out, would it be too much? The bell rang and it was time for me to go back to my room. When I entered my dorm room, my jaw fell open. Melissa was not there, but all of my bikini posters had been replaced by pictures of hot guys in tight thong speedos. A small package with a note attached sat on my bed. As my eyes moved to the package, I notice that she had replaced my plain white comforter, to a white comforter with small flowers all over it, pretty much in the same pattern as my Victoria's Secret panties Melissa found earlier in the day. I read her note, she wanted me to take a shower, wash my hair and body with a strong flowery scent, then dry off, moisturize my body from head to foot with the enclosed nice smelling moisturizer, put on my new pair of matching panties and a bra (both pink with little hearts on them), a dress with a floral print from Victoria's Secret, and to finish up my new outfit with makeup and a blond wig with pigtails, each pigtail tied with a bright pink ribbon. Melissa also had found one of my many pictures of me in drag, she circled the picture and stated that she had no idea how I created the cleavage in the picture, but wanted me to duplicate whatever I did for tonight's meeting. The last thing the note said, was to spray myself with the enclosed bottle of Beautiful perfume and then to head over to Melissa's dorm room ASAP. After preparing for our date, I peered out my door. I have a small frame, but my current outfit was going to get a lot of attention. My floral dress wasn't very long and let a lot of my fake cleavage show. I figured I would just have to suck it up and go. I counted to ten and pushed myself to go outside. I quickly headed out toward Melissa's dorm almost on the opposite side of our campus. Luckily the path is quite dark until I got near my destination. So far so good, I thought to myself, I pushed myself to walk as fast as I could without falling over. Just before I reached Melissa's room two large basketball players passed by me. "Good evening Miss, I hope you don't mind if I say your outfit is wonderful. It's nice to see that there are a few women still out there that don't dress like a bunch of femi-nazi dykes in loose black jeans and shit." It was Jeb, our most popular player, of course he was a hit with all of the ladies. "Thank you," I said quickly, "but I am late to meet my boyfriend." "Shit," he replied, "I should have known a chick like you would be already spoken for, ha, ha, well you know where to find me if something falls through." I thanked him and hurried on. Finally I reached Melissa's door. When the door opened, Melissa was standing there in the doorway. "Get inside now bitch, fucking whore. I saw you flirting with those two guys." She pulled me inside and pushed my face into her bed, so my butt was sticking up in the air. She started whipping my butt with a belt. After about twenty or so hard hits to my now tender rear end she stopped. Tears were now streaming down my face as Melissa sat down beside me on her bed. "God dammit, now your mascara is running down your face," she growled. Melissa rested a bit and I basically just whimpered and rubbed my sore butt. "So you really want a bitchy dominant girlfriend, right?!" Melissa asked, already knowing the likely answer. I looked into her beautiful crystal blue eyes and had to admit that femdom was about the only thing that excited me. "Well," she said, "I used to think that I was a lesbian, but now I know that I want a sissy boy." She leaned over and whispered and gently blew in my ear, "You want to be my little sissy girl don't you, admit it bitch." "Oh god yes, please let me worship you mistress," I pleaded. Melissa smiled and said, "Do you like your pretty pink panties, slut?" As she said this she started to pull my panties down. "You wanted to suck those hot guys on the walkway didn't you, you little faggot sissy slut." I stammered that she was wrong, I wasn't gay. "No!" she yelled as she started pulling my panties back up. "Let me make this clear to you sissy, admit you are a cock sucking slut and panties slip off and I will let you put your little clit inside me, or be an idiot and deny it, then your panties go up and you can walk home with blueballs. Got it bitch!? Admit you are a sissy faggot and panties go down, or be a damn pain in the ass liar and it is blueball city, simple enough for you dumbass?!" Melissa shouted. My horniness took over and so I said that I wanted to suck the jocks hard dicks. "Umm, yes I thought so," she laughed. "Will you drink their cum for me, please lil' sissy girl, right kitten?!" Again my reason was overcome by my growing need to get off. "YES!!" I proclaimed loudly in a pleading voice yeaning for Mistress Melissa's attention. She pulled my panties off and quickly removed both of our clothes. Melissa smiled as she got on top of me and guided my cock into her love channel. At first my penis missed its mark and slid past her opening and instead when up along her leg. "Oh, you know you want this, right kitten?" Melissa teased. I gave her a confused look, then quickly said, "Uhhh, yes!" "Uh, you don't' know if you want pussy, you sound unsure there little girl. Oh my god, are you a virgin? I mean it is OK if you are I just want the truth." Melissa continued her tormenting. I again looked into her eyes and admitted that I was still a virgin after all these years. "Wow, cool!" she laughed. Then in a mocking voice she stared to sing the Red Hot Chili Peppers song, "Breaking the girl" just to humiliate me further. My new mistress reached back and grabbed my little sissy dick, then grinned like a Chester cat as she guided my cock inside of her. It was amazing to feel my cock push through her opening and slide into her hot wet cunt. Melissa slid up and down on my cock a few times then slowly leaned forward so we were face to face with her fucking me. "So what kind of nasty fantasies does my little sissy kitten stroke herself to when you have your little girly hand wrapped around your tiny dick, humm bitch, and you better not fucking lie to me, tell me bitch! Don't hold back and don't you dare lie. As a matter of fact, I fucking command you to tell me your secrets, I know you don't want to reveal some things, but it will come out eventually and I will be very fucking pissed if you lie to me, got it you fucking little shit!" She grabbed my hair under my wig and said, "Come on, speak, tell me what I want to know, you know you have to confess to mistress Melissa, right whore?!" In a moment of amazing horniness with her warm wet cunt gripping my cock and her warm juices dripping onto my balls I lost all resistence and told Melissa that I masturbated primarily to cuckolding, humiliation, and also got off on latex fetish pictures and stories. Melissa smiled, "God, we were made for each other." Tears sprang to my eyes I was so happy she liked what I wanted and wanted my fantasies to come true. At the same time I was a bit worried that I wouldn't be able to handle one of my stroke stories from jumping from a harmless story online to reality, but it was a little late to put the cat back in the back in the bag if it was too much. Melissa started moaning and started chanting, "My own little cuckold sissy slut, oh god yes, yes!" I could feel her vaginal muscles tightening around my cock as I felt my own orgasm building. My cock swelled inside of Melissa as I climaxed inside of my mistress. Jets of sperm shooting inside of her sent her over the edge and she started screaming as she climaxed at almost the same time. During the winter break from classes, Melissa and I spent the days talking and having sex many times each day. I was amazed at how sexual she was. She constantly told me about her previous boyfriends and compared my dick to theirs. I couldn't get enough of her humiliating me on my inadequate pecker. On the Friday of our first week off, we were in the lunch hall again, this time Melissa's long term friend Jenni joined us. I sat down with my new usual meal of a salad, ice tea with no sweetener, and some vitamins Melissa wanted me to take. "So," Jenni started, "Melissa tells me that you are her sex slave and you like to be dominated by a beautiful bossy women." I couldn't believe that Melissa had told her about our situation. My reddening face told her that what Melissa had told her was indeed true. As Melissa sat down at the table, she commanded, "Well answer my friend slut!" I admitted that I loved Melissa's humiliation and I was totally in love with my mistress. Jenni laughed and added that Melissa told her about my small cock and how I liked to wear panties. My face was bright red and mistress commanded me to show Jenni my panties. Jenni broke out laughing when she saw my pink panties. "Well, Ok, Jenni said, "Whatever makes you happy." She continued to debase me by adding, "Melissa is right, all I can see is a tiny bump in your panties, without that tiny bump no one would mistake you for a man." Melissa turned to Jenni and they talked about how they loved to dress up in provocative outfits and drive guys nuts. "We should do that tonight, Jenni and added, "I would love to tease boys plus if I find a real man." Melissa turned to look me right in the face and added, "I could fuck his brains out." Still looking at me my mistress added, "You want me to have real dick, right, plus if you are good I could let you watch, you know you might learn something." I was totally humiliated, but I wanted to see my princess happy even if it hurt me. I was jealous but excited by the idea of Melissa making love to another man. The idea made me very excited, but for some reason my cock remained soft. After our dinner we want to Melissa's dorm room and prepared for our night out on the town. Melissa had me wear the same outfit I had originally met her in on our first "date" except now she added a white garter belt and white fishnet stocking. "Ouch" I said as my bra rubbed past my nipple, "Man my chest is sensitive all of a sudden." Jenni spoke up, "That is probably a side effect of the female hormones." Melissa shot a pissed off look at Jenni, and said, "I was going to tell him about that later." "Oh crap, I am so sorry Melissa!" Jenni pleaded. "Well, we better let this little bitch on to what is really gong on. I have been giving you female hormones telling you that they are vitamins and the moisturizer you have been rubbing into your body from head to foot is from a transformation website and is packed with the maximum amount of estrogen possible. I figured that you wouldn't mind being a bit more feminine plus, it might make what I have to tell you a bit less jealous if you don't have all that nasty testosterone going through your veins. This week my old boyfriend called me. He is an older gentleman but, he has a nice big fat cock and is very experienced. I love fucking him and we are going to meet him tonight." It was almost too much to process at one time. I was angry, jealous, nervous about the effects of the female hormones, and horny all mixed together, basically a cocktail of emotions. I kept thing about Melissa with her old boyfriend the entire way to the clubs around D.C. At a bar in Georgetown we met up with the infamous Bill. He was an older guy, and I could tell why Melissa liked him, he was clean cut, sophisticated, and very confident. You know, basically everything I wasn't. I noticed that the bar we were in, was a mixed bar with straight and gay sections. Jenni grabbed my hand as Bill and Melissa went to a booth and stared making out. "Come on!! Let's leave them alone, plus I want to check out all the hot gay guys, maybe I can convert one of them," she laughed. We sat down at the bar and Jenni told me to turn sideways and push my chest out. As I did, she mentioned how my breasts were already starting to grow. Your breasts should be about one cup smaller than your sisters's. I gave her a panicked look and told her that my sister was a double D. "Well you should have some big hooters soon," she stated while laughing. A guy sitting next to us broke in, "I am sorry but I couldn't help but over hear some of your conversation. Are you a she-male?" Before I could say anything Jenni answered for me. "Chrissy is already on female hormones, but isn't sure how far she will take things right now." He exclaimed, "That is so cool, we get a lot of drag queens in Dupont Circle, but not too many people are willing to take the extra step and start getting permanent things like breasts." "Let me buy you girls a drink," he said in a nonchalant tone. He got Jenni and I a Manhattan, then turned to his friends and told them about me. After two drinks he asked me to go out on the dance floor. Jenni wouldn't let me answer no. "Melissa wants you to have some fun too, girl," she grinned wildly as she said this. I went out on the dance floor with a third drink as Melissa joined Jenni at the gay section of the bar. As I danced with my "date" I watched Bill openly fingering Melissa at the bar. I was getting turned on by my "date" constantly telling me how pretty I was and grinding his hard cock into my softening feminine butt. Melissa brought Bill out onto the dance floor and she gave me another drink as she passed by. She then started to passionately french kiss Bill and I could see his hands rooming over her body. I was somewhat jealous, but amazed how aggressive and brazen Bill was in public. Bill looked at me and told Melissa he could see why she still needed him, "You are pretty much a sissy boy aren't you, god you almost look like a woman, ha, ha." He added insult to injury and continued his humiliation of me, "Do you want to see a real man fuck your girlfriend?" My face was burning with humiliation, Melissa spoke up, "Go on sissy slave show Bill your small dick." As she said this, she laughed and pressed Bills pants tight around his impressive cock. "Slave tell him that you have a small girly cock and would like for your mistress to enjoy a real man for a change," she commanded. My face turned several shades of red as I followed my mistress's orders and stated, "I have a small cock and would like for Melissa to enjoy a real man's cock." Melissa smiled as Bill pushed her down to his crotch. She took Bill's cock out and said that I should follow along with my boyfriend. The guy I was dancing with got a huge smile on his face and pushed me down onto my knees. I am not sure if it was the drinks of the humiliation but I didn't want to displease my mistress. I pulled out his cock, and followed Melissa's lead. I watched as Melissa sucked up and down on Bill' hard member, every once in a while she would stop to concentrate on the head of his cock and run her tongue around the head of his fuckstick. My new friend pushed his hard cock down my throat and I felt someone pushing my panties down. I wanted to see who was behind me, but all I could see was the man's cock I was sucking. God what a slut, Melissa said as she decided to take things a bit further with Bill. She stopped sucking his cock and told him to fuck her and to not pull out until he had shot a nice load of cum in her cunt. I felt a cock slipping into my ass as I continued to suck the cock in front of me. Melissa pretty much kept pace with me until Bill started to moan. Melissa turned and laughed at me, "You are so pretty my little cuckold slut." I hope you enjoy watching your girlfriend getting knocked up by a real man. I looked quizzically at her as she said this. "This is your last test, plus you have been the one taking all my birth control pills to femininize you. I could only look on with amazement as I watched Bill cum in my mistress' pussy, shooting his fertile seed deep into my unprotected mistress's uterus. As Bill climaxed my boyfriend shot his load into my mouth, and my apparent second "friend" came in my sissy pussy. I came with my worthless cuckold sperm shooting onto the dance floor. Billed looked over at me and said that my sissy sperm belonged on the floor and not inside of a women. Bill, Jenni, and Melissa all laughed as Jenni added, "No, babies for the sissy faggot, like any women would want sissy faggot genes." After that night Bill let Melissa and myself move into his large vacation house, located on a private beach in Hawaii. Melissa continued my feminization and my new boyfriend introduced me to my new job as a she- male porn star, of course taking all the profits and sharing them with Bill and Melissa. He had videotaped the entire dance floor sex scene with me taking on two men at once, and then he made the video available on all of his numerous gay porn websites. Once word got around that I was a feminzed she-male starring in my own porn video, my old life was pretty much over with. Knowing that there wasn't too much hope of me finding gainful employment outside of the porn industry, I resigned myself to my fate and spent my days starring in she-male porn videos and my nights serving mistress Melissa and her many lovers. Life is good ;)

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Sissy Farm Chapter Sixteen

Sissy Farm - Chapter 16 By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

2 years ago
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Sissy School Part 4

SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

2 years ago
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My Daily Sissy Schedule Part 1

My Daily Sissy Schedule I met Daddy online a little more than a year ago. He lives about five hours away from me, but promised that despite the distance, he could help me become the perfect sissy slut if only I would agree to follow his schedule for me. I readily agreed, and started down the path to becoming his perfect sissy whore. Here's a peak at my sissy schedule, just in case there are any other sissies out there looking to add a regimen to their life. I wake up every morning...

4 years ago
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Forever Her Sissy Chapter 5

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. Forever Her Sissy - Chapter 5 The ride home was wonderfully uneventful. So many things had happened today, It had been confusing and...

1 year ago
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My Sissy Calling

My Sissy Calling Like many recent college graduates, I found it hard to get a job after I received my super-impressive English degree. Sure, the job market was tough and my degree wasn't going to open any doors, but part of the problem was that I still didn't have any idea about what I wanted to do with the rest of my life. I was looking for a calling--something to give my life meaning. I thought that I would find it in college, but it never came. Well, that's not exactly true. I...

1 year ago
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Sissy Farm Chapter Eleven

Sissy Farm - Chapter Eleven By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA. Auntie...

1 year ago
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Sissy Emma is turned

Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

3 years ago
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My Sissy Schedule

Author's Note: Another reader request, this one from a fellow sissy who enjoys when I write about a daily routine that helps keep me in a sissy headspace all day long. She requested that it be detailed enough to seem plausible, should somebody want to start following the schedule. And of course, it should spiral out of control so that her sissy stick throbs in her panties. I'm always happy to oblige. I'm left wondering if I could actually follow such a sissy schedule. It would sure be...

1 year ago
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Forever Her Sissy Chapter 4 of 6

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. Forever Her Sissy - Chapter 4 More shopping? I thought to myself. How much more of this could I take. "Mrs. Karen?" I spoke...

2 years ago
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The Sissy Contest

Author's Note: This is a quick one off story written from a reader request. I was especially motivated to write this as a genuine sissy training fantasy, with the hopes that somebody would read it and use it as a blueprint IRL. That certainly got my clittly interested! Enjoy! And as always, please feel free to comment here or contact me directly at [email protected] xoxox Emshoninque The Sissy Contest My phone rang just after 3am-caller unknown. I normally don't answer...

1 year ago
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Crowd Sourced Sissy 3

PREVIOUSLY ON CROWD SOURCED SISSY: In part 1, a man met a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. In part 2, the man decides to become a sissy as well. He travels to New York with visions of sissy in his head, but the anonymous Master who is controlling his fate has other plans for our poor sissy. Crowd Sourced...

3 years ago
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Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

2 years ago
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Sissy Hypnosis Fun

Sissy Hypnosis Bet I have always been something of a night owl, which means that I take a while to get up and going in the morning. My alarm generally goes off at 7am, I hit snooze two or three times, then I finally get up and hop in the shower while my coffee pot starts to percolate. I grab my coffee and try to head out the door by 7:45, which is just barely enough time to get me into the office by my 8am start time. Needless to say, I frequently arrive with my hair still wet and...

2 years ago
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Sandys Sissy Maid

Sandy's Sissy Maid By maidboy275 Mistress Sandy had given me a simple order, "When you get up Monday morning get dressed into your pink domestic maid uniform." I knew I needed to do it, I even planed on doing it. Sunday night I had added a new coat of polish to my always polished toenails and then used the deep pink nail polish on my fingernails. I had let it dry in order to be ready first thing Monday morning. I had gone over my body with a razor in the shower and made sure I...

2 years ago
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Online Sissy Training

Online Sissy Training I must admit that I was surprised, but also thrilled to get the email. "Hello Sissy Michelle;" it read. "Please excuse my impertinence in reaching out to you, but I have seen several of your posts on Craigslist, Fetlife and Adult Friend Finder. You always say that you are a sissy seeking dominant men who will train you to become a sissy cum slut. I am guessing that you have not found that man as of yet, because I keep seeing variations on the same ad week...

1 year ago
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A sissy called Jezebel

Part I - Jezebel starts her big day, serving as a sissy maid for the dominant females of hir family. We seen in depth hir morning routine, as sie gets her sisters and hirself ready for school. My alarm goes off at 5:30 in the morning. It is an old fashioned wind up alarm clock with the clapper bell ringer which would wake up the dead, or at least this sissy who had been dreaming sweet dreams of dancing in a full ball gown with hir Prince Charming. I turn on the light on my side...

2 years ago
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Curiosity Spanked the Sissy Finale

You watch Mistress Michele sway towards you provocatively her red lacy worn panties dangling from her finger. Your cock throbs painfully knowing exactly where they are going. Reaching you she takes hold of the dildo and you plead with your eyes for her to remove it. Instead she turns it until the rubber balls are resting against your chin, a wicked smile on her lips. "I never knew what a cock sucker you were..." she smirks and you blush. "I mean ten inches!.You're a pro!..perhaps I...

2 years ago
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Sissy gets a black master

Sissy Gets A Black MasterI got up wearily from my long and exhausting night being fucked andpunished by my new Black Master. As I awoke, I could scarcely believe thatall those depraved things had happened to me. One minute I had been merelyexchanging emails with a man, who could have been anywhere and the nextminute, that very man was at my door, in my home, and then inside mybody. Black Master, a man whose name I didn't even know, a man who lookedto be about ten years my junior, had taken me...

3 years ago
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I Now Own You Sissy

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. "Then a week before the next visit you'll not be allowed to cum, if you do, you'll be punished very firmly. I'll be measuring you cum output and will know if you...

2 years ago
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My Sissy Secret

My Sissy Secret I got the text on Friday afternoon, just as I was heading home for the weekend. I glanced at my phone as I left the building and stopped dead in my tracks. I didn't recognize the number, but the text sure got my attention. "Hello Sean," it read, "or should I say "Sissy Sean." I was standing in the parking lot trying to decide whether to block this guy or just ignore the text when his next message arrived. "I don't know if you remember me," he wrote, "but I...

4 years ago
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Crowd Sourced Sissy 2

PREVIOUSLY ON CROWD SOURCED SISSY: A man meets a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. The guy decides that he wants to/needs to join her as a willing-to-do- anything sissy, so he starts his own website. He will become a perfect sissy by doing whatever his online fans demand. Crowd Sourced Sissy 2 My trip...

3 years ago
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Sissy Training at Last

Sissy Training at Last The email came at 3pm on the Saturday before my birthday. All things considered, I have to admit that His timing was perfect. I'd just returned home, and as I had the rest of the weekend free, I'd decided to have a little fun. For me, "a little fun" meant that I'd indulge in some sissy fantasy play. You see, I've been a closet sissy for years, and even though it's my main sexual kink, I hadn't really found anybody who wanted to make my weekend fantasy into my...

3 years ago
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Sissy Farm 20

20 Sissy farm List of Characters. Me. Michelle A Natural transvestite sissy. Janice My Younger sister Aunty Bev Janice and My mother's Sister. Mistress Janet Headmistress of the young lady's academy Doctor Shirley Williams. My endocrinologist. Miranda. A very effeminate Sissy sales assistant. Miss Stern Miranda's mistress who owns the shop. Peregrine AKA Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James AKA Auntie Jamie Peregrine's...

1 year ago
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Sissy Farm Chapter Fourteen

Sissy Farm - Chapter Fourteen By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty...

2 years ago
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A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told...

1 year ago
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A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told himself,...

2 years ago
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The Sissy Diaries My Two Mistresses

Dear Diary, Things were going so good for me. I got promoted at work, even though I know most people there don't like me because I'm quiet and reclusive. It's just that I can't get too close to anyone there and risk exposing that I'm a closeted crossdressing sissy. Still, I do my work and go home to my apartment and escape into my sissy world. Still, I decided that with my promotion and my increase in salary, I could afford a better apartment in a better neighborhood and that's where...

1 year ago
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Classroom Sissy

Classroom Sissy By Cassandra Morgan I did it! I got in! Me! Geeky Brad Hollins. I'm one of the 10! I'm finally accepted! I'm finally one of the chosen few! I never thought I had a chance. After all, more than 200 students apply for the 10 every year, and 190 of them go away disappointed. Only the finest minds at Calvin Coolidge Community College (CCCC) get a Golden Ticket. And I'm Willie Wonka! Whee! You've heard of the 10, haven't you? It's a secret honor society at CCCC,...

4 years ago
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Sissy Velina

I walk into the living room of my master. I am completely sissified and wear a very frilly sissy maid outfit. My 6" white leather peep too high heels have thick leather straps around my ankles and are closed with medium sized padlocks. I wish I knew where my master holds the keys. On my lightly sun tanned and smoothly shaved legs I wear white sheer seamed stockings and with a nice lace band at the top. At the back the pink seams end with large pink girly satin bows. Just above my...

3 years ago
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A Submissive Sissy

A Submissive SissyMy sissy slave husband, Princess, was in the process of paying his usual obeisance to my feet on a recent morning. It's always good to see Princess applying his tongue to my high heels and on this particular morning he was working extra hard to please me since he was about to beg me to not take him to the beauty parlor. He knew that it was unlikely that I would relent, nevertheless, the outings I arrange are so excruciatingly humiliating for the poor dear that he is ever...

2 years ago
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Americas Next top Sissy part 5

Part 5 So Part 5 of my homage to 'America's Next Top Model' forced fem style lol ... hope you enjoy it and please comment. After a humiliating photo shoot the sissies wake up to another elimination. Jim felt better after a night's sleep, only to face wearing the overly feminine pink sissy dress he and the other sissies are forced to wear for the elimination. 'Getting eliminated, maybe that's the way out? At the very least I would get the satisfaction of denying these sick...

2 years ago
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Dr Cooks Sissy Clinic The Begining Jade and Deans Experience

Dr. Cook's Sissy Clinic: The Beginning and Jade and Dean's Experience. By dirteesissy I gazed at Jade's bottom, as she raped her husband's ass with a 10" strap on cock. Her pounding of her sissy maid's hole, bordered on the extreme, somewhere between love and hate, she punished that sissy ass with long powerful strokes. Jade, dressed in just red thigh high P.V.C. boots and gauntlets of the same material, was making mincemeat of her hubby's derriere and I looked on with pride at my...

1 year ago
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Cuckold Sissys First Meet Fantasy

This fantasy summary was sent to my wife and her prospective boyfriend to let her boyfriend know our fantasies and for me to know which bits got my wife and bf really wet? And feeling very horny? Which bits she really liked? And what they would you like to add to also?The text was sent to the prospective boyfriend's iphone with a picture of me on all fours showing my girlie soft pathetic knickered and caged boi-clit after he sent me a picky of his gorgeous cock which I had previously been lucky...

2 years ago
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I Want To Be A Sissy Part 1

Oh, my goodness! Today is going to be an exciting day. Mistress and I will find out if I can finally fill the C-cup brassiere she desires that I wear. I am so excited! A C-cup means so much to me. I adore my B's, the darling little girls, but a Sissy can be so much more of a Sissy when her cup size says WOMAN! As soon as I finish my morning toilette, Mistress will hook me into the cutest white underwire C-cup bra I have even seen and the moment will be here. I will fill the cups or...

2 years ago
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Andrew The Unsuspecting Sissy Part III

ANDREW THE UNSUSPECTING SISSY PART III [email protected] MAY I SUGGEST THAT YOU READ THE EARLIER CHAPTERS OF ANDREW SO THAT YOU MAY UNDERSTAND WHAT THE POOR DEAR HAS BEEN THROUGH THUSFAR..... ANDREW NOW DREW: SISSY SUPERSTARSOON TO BE HUSBAND TO JIM JIM : BILLIONAIRE INDUSTRIAL WITH A PENCHANT FOR SISSIES AUDREY: DREW'S STEPMOTHER AND OWNER OF THE MANOR SARAH: DREW'S STEPSISTER AND TRAINER VALERIE: DREW'S DOCENT TRAINER DR NEWMAN: MEDICAL DIRECTOR OF THE MANOR PENELOPE...

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