Transvestite

The Bet_(1)

/ Categories: Blowjob, Fiction, Transvestite / Blowjob, Fiction, Transvestite / By

My friend Cristina and I were just sitting around watching porn. It’s something we do for fun now and then. Believe it or not, it has never led to anything. A scene came on where a guy was put in a wig and satin nightgown and fucked by a beautiful blond dominatrix with a strap on. We laughed at what an ugly girl he made and somehow it came up that I had a girlish look to me. She said that I would look much more like a girl in the wig and nightgown than the guy from the movie. I just smiled. Later that day out of nowhere, she told me that she’d like to test that theory. She wondered if I’d let her dress me up. Though about it for a moment and …

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Jessy

/ Categories: Coercion, Fiction, Transvestite / Coercion, Fiction, Transvestite / By

I was in my attic looking for lamp that I had stored for my sister.  It was getting hot so I decided to open a couple of dormer windows to let some air flow.  When I opened the last of the thee windows which was on the back of the house I could hear music coming from my neighbors back yard.  I knew that they had just left for a 2 week trip to Europe and only their 19 year old son, Jessy, was home so I was a bit surprised to see a sexy young lady laying on her stomach sunning by the pool in a pink thong.   I used my camera and snapped a few pics,  I zoomed in and was able to get some pretty good ones.  She raised up on …

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The Sex Book

/ Categories: Bi-sexual, Fiction, Pegging, Role-playing, Transvestite / Bi-sexual, Fiction, Pegging, Role-playing, Transvestite / By

It all started on my birthday, the year I turned thirty. My wife Anna and I had been going through a bit of a slowdown in our sex life recently. Nothing too extreme… after five years of marriage, and with our first child, Christine, barely old enough to finally be sleeping through the night, I imagine we weren’t any worse off than any number of couples in similar situations. But the lack of sex, at least relative to the frequency with which we used to have it, was certainly one more source of stress for both of us. That situation, and Anna’s desire to do something special for me on my birthday, was what prompted her to buy us the book. It was one of those ‘bring spice back into your relationship’ deals, filled with …

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MY NEW OLDER LOVER AND HER FRIENDS

/ Categories: Ass to mouth, Bi-sexual, Blowjob, Boy, Cuckold, Erotica, Exhibitionism, Girls / Female, Group Sex, Lesbian, Male / Females, Older Female / Males, Oral Sex, Teen, Transvestite, True Story, Voyeurism / Ass to mouth, Bi-sexual, Blowjob, Boy, Cuckold, Erotica, Exhibitionism, Girls / Female, Group Sex, Lesbian, Male / Females, Older Female / Males, Oral Sex, Teen, Transvestite, True Story, Voyeurism / By

We made love on our second date, fucking long into the night. Quickly realising Charlene was far more sexually sophisticated than me. Fucking me in positions and situations that were completely new to me. The mirrors in the room she used for sex were a new level of sexual sophistication for me, mirrors on four walls and the ceiling. Looking at Charlene’s big ass while she was fucking me while on top of me was a huge new turn on for me. The first time Charlene gave me fellatio, a head job, she reinforced just how sexually sophisticated she was, talking to me as she teased and edged me to an incredible orgasm. When Charlene asked me to worship her big ass for the first time, I realised just how sexually naive I was. Her …

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Working ‘Girl’_(0)

/ Categories: Blowjob, Boy, Fantasy, Gay, Prostitution, Transvestite, Young / Blowjob, Boy, Fantasy, Gay, Prostitution, Transvestite, Young / By

Brian sat impatiently on the park bench, fidgeting in anticipation and excitement. He quickly checked his phone for the time yet again, seeing it was just after 1AM. It was the perfect time for meeting a customer. He reached over to run his fingers along the signature red bracelet over his left wrist, which let men in the area know he was ‘working’. His ears perked up when he heard some noises off in the distance, a gentle rustling in the bushes. Brian smiled slightly, knowing someone else must be doing just what he was about to do now. He thought about that video game he wanted, the one all the other kids at school were talking about. But at 14, he was too young to have a job, and too old to convince his …

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Horny Holiday

/ Categories: Fiction, Teen Male / Teen Male, Transvestite / Fiction, Teen Male / Teen Male, Transvestite / By

Mac & his ‘girlfriend’ Lewis had gone on holiday with Mac’s elderly parents to a static caravan near the sea. Both the mid-20’s lads had taken items to dress in, but had found it difficult over the couple of days that they’d been there to have some special time together. Mac’s parents did retire to bed early on the third night, leaving the two frustratedly playing each other up in the lounge area. After an hour or so, Mac got up, & with a sly wink whispered “I’m gonna turn in too, don’t sneak into my room looking for affection all dressed up either” and went into his bedroom. Lewis went to his room, starting to get horny at the naughtiness that was possibly going to play out – if he’d read Mac’s signals correctly! …

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DNA Chapter 4

/ Categories: Fantasy, Pregnant, Transgendered, Transsexual, Transvestite / Fantasy, Pregnant, Transgendered, Transsexual, Transvestite / By

Anne worked way into the afternoon, finally she leaned back and stretched her stiff back. On the screen lay the plans for a simple addition to the DNA viruses running around, that should make the transmission much more difficult, but not impossible. She had to stop the problem now before it spread. Jim wandered into the kitchen, “Finished?” he asked. “Yep, this should stop you, Julie and Paul, passing this on to anyone, if you have any more ‘accidents’. How are Julie and Paul?” “Julie is handling it quite well, but Paul, I don’t know. He is very withdrawn. Perhaps you should talk to him.” “Tonight, today I have to prepare and test this.” She gestured at the screen. “Julie needs to get some more clothes, You live near the institute, don’t you.” “Yeah, you …

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Sister’s Surprise, Chapter 3

/ Categories: Blowjob, Consensual Sex, Female solo, Fiction, Incest, Male Solo, Masturbation, Romance, Teen Male / Female, Toys, Transgendered, Transsexual, Transvestite, Voyeurism, Young / Blowjob, Consensual Sex, Female solo, Fiction, Incest, Male Solo, Masturbation, Romance, Teen Male / Female, Toys, Transgendered, Transsexual, Transvestite, Voyeurism, Young / By

Sister’s Surprise, Chapter 3 It was not a restful sleep. Haunting questions of my own sexuality plagued my dreams. In one such consuming dream, I was Michael again, bigger, stronger, more masculine than I had ever been before, or could imagine myself being. With this physique, I easily brought woman after woman to my bed. Each succumb to my sexual prowess, each removing their clothes as they fall backwards on an oversized bed, then spreading their toned legs to invite my powerful cock inside of their womanhood. Each one thoroughly defiled, filled with my potent cum, before moving on to the next. And as my latest sexual conquest, a dark haired teenage girl no older than myself, lay on the bed before me, her slight, petit body became aroused. Her pink nipples hardened beneath my …

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Mixed Signals

/ Categories: Anal, Blowjob, Cum Swallowing, Domination/submission, Transvestite, True Story / Anal, Blowjob, Cum Swallowing, Domination/submission, Transvestite, True Story / By

Mixed Signals – by I Am Tina To You (c) 2011 Some secrets should be kept to yourself. Some secrets are better explored with others. My secret fascination with being treated like a girl by men and dressing like a girl for men straddles that fine line at times. It is something that’s been with me since I was a young boy, and I am in my mid 30’s now. I have let very few men into that world, out of fear of being outed or hurt, and always do my due diligence when committing to be with a man in that situation. I can’t explain myself very well, other than I know I really enjoy it, and it’s painfully evident how much I enjoy it by the way I treat a man if I …

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Teenage boy blackmailed

/ Categories: Fantasy, Girls domination, Teen Male / Female, Toys, Transgendered, Transsexual, Transvestite / Fantasy, Girls domination, Teen Male / Female, Toys, Transgendered, Transsexual, Transvestite / By

Chris was your average teenage boy. He liked girls, sports, and hanging out with his buddies. Chris was a bit short, around 5’6”, and weighed no more than 130 lbs. He had a nice, flat stomach and lanky arms from soccer, with longer brown hair and nothing but peach fuzz on his face. Despite younger features and a hairless body, Chris had developed nice legs and a bubble butt from all the soccer. His cock was a little below average, only about 5 inches long. Being an only child and a hormonally raging teenage boy, he loved porn. One night, he stumbled across some shemale porn, and man did it turn him on. He was hooked, the only thing that turned him on now was these beautiful women with cocks bigger than his. His attractions …

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AuntSammy

/ Categories: Anal, Blowjob, Cum Swallowing, Transgendered, Transsexual, Transvestite, True Story / Anal, Blowjob, Cum Swallowing, Transgendered, Transsexual, Transvestite, True Story / By

i was about 13 years old. i went to jr.high like everyone else but things for me were a bit different. I had a10’inch Cock and when i was little, i was always embarest about it because when i was young(About 6 years old, it was like 7’inches at the time) i would always get an erection and all the kids would make jokes about it. this is a true story. My dad passed away when i was 5 so it was just me and my mom. My mom, considered to other guys, was extremly hot. She was about 5’10 and weighed 130 pounds. she had Blonde hair and Blue eyes and had C-cup breasts. i even admited she was hot but of course i wasent into my own mom. she once worked as a …

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Velma and Daphne

/ Categories: Consensual Sex, Fiction, Teen Female/Teen Female, Transgendered, Transsexual, Transvestite / Consensual Sex, Fiction, Teen Female/Teen Female, Transgendered, Transsexual, Transvestite / By

My name is Velma Dinkley. I could have never expected to happen while solving a mystery a few days ago. It was my last one before I got out of the mystery solving business. August 16, 2005 16th Century Castle Austria When the gang all split up I decided to go with Daphne. I was a closeted lesbian at the time and I had a burning desire to taste the sweetness that Daphne had between her goddess like legs. Daphne, sexiest woman I have ever known. She had perfect 36 DD breasts and a figure that rivaled the great Aphrodite. Oh my God just talking about her body is turning me on. While were walking down a long hallway Daphne saw a strange light. “Hey Velma did you see that?” said Daphne. “Yea, lets go …

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Camming Down the Rabbit Hole Ch.11

/ Categories: Anal, Bi-sexual, Body modification, Bondage and restriction, Coercion, Erotica, Exhibitionism, Fiction, Male Solo, Masturbation, Prostitution, Role-playing, Toys, Transgendered, Transsexual, Transvestite / Anal, Bi-sexual, Body modification, Bondage and restriction, Coercion, Erotica, Exhibitionism, Fiction, Male Solo, Masturbation, Prostitution, Role-playing, Toys, Transgendered, Transsexual, Transvestite / By

I sat there for some time, my phone still in hand. I couldn’t fully comprehend the situation and where I was. All this started when I was put on furlough and thought I would be losing my job, an idea born out of boredom, hornieness and desperation. What started as a regular cam show with a guy hoping to earn a little money, before being subtly coerced into dressing in lingerie, and taking small step after small step before I tumbled well and truly down the rabbit hole ending up wearing more female clothes and then using toys and other things. And now I was sitting here some months later, hours of dedicated and specific exercise had sculptured my form with a slim waist and upper body, but curvy legs and a decidedly juicy ass …

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family changed ron to rose

/ Categories: Anal, Cum Swallowing, Fiction, Transgendered, Transsexual, Transvestite / Anal, Cum Swallowing, Fiction, Transgendered, Transsexual, Transvestite / By

hi i am Rose this story is about how I was turned into rose from Ron by my family. I am a 20 with 34D boobs. My family consists of 3 members my sis julie of age 25 and 36d, aunt susan of age 35 and 38d and mom of age 42 and 40d . My story started when I was 18, all the three ladies loved me a lot . they took lot of care of me.my sister used to make me bath some times.one day my sis was making me bath so playfully I splashed water on her and she was completely wet so I asked her to remove her dress and have bath with me at that time I don’t know about sex . so sis opened her dress completely I saw …

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Sister’s Surprise_(0)

/ Categories: Consensual Sex, Fiction, Incest, Romance, Teen Male / Female, Transvestite / Consensual Sex, Fiction, Incest, Romance, Teen Male / Female, Transvestite / By

This is my first story, and I apprieciate any constructive critism. A closet cross-dresser is caught and exposed, but gets an even bigger surprise from his sister. Sister’s Surprise My parents would never understand. How could they? They raised my to be a good little boy, and that was all they knew. They had no idea about my cross-dressing fantasies. It was a life I kept secret from everybody. And until three days ago, it was secret I kept even from my girlfriend April. A business meeting that ended early also ended our relationship. I was always small growing up, but that didn’t stop me from being active. In Junior High, I had wrestled and was on the track team. In high school, I joined the swim team, but it was my track career that …

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Sam’s sister’s black bf’s cock.

/ Categories: Black, Blowjob, Cum Swallowing, Fantasy, Interracial, Transvestite / Black, Blowjob, Cum Swallowing, Fantasy, Interracial, Transvestite / By

Sam woke up on the first day of summer and took a shower before heading downstairs to eat. In the kitchen he noticed a note from his dad saying he’d be home late and one from his sister saying she was at her bf’s. Grinning Sam finished and went upstairs to his sister’s room where he began looking through her old clothes that he had discovered recently. Luckily his sister Liz was 2 years older than him at 15 so her clothes fit him pretty well. He put on a short black shirt and a black blouse with a red thong and bra stuffed with very realistic padding. Next he hurried into his Dad’s room and grabbed one of his Mom’s old wigs before going back to his sister’s room to put on mascara and …

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My Daddy is my Mommy

/ Categories: Incest, Transsexual, Transvestite, True Story, Young / Incest, Transsexual, Transvestite, True Story, Young / By

Hello my name is Sally. I am 12 years old and I love my Daddy to bits. He is so kind and does his best looking after a little girl whose mommy had died a year ago. The trouble is he doesn’t really know how I like to feel feminine – all my nighties are flannel and my panties are white cotton ones, though they do have a rosebud in the front! My skirts are much longer than my friends and my blouses are very plain. He seems not to have noticed that my breasts are growing – they are not very round but are very pointy like volcanoes with large dark brown nipples. They are so sensitive and excite me when I stroke them – so I need to wear a bra to stop …

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When I Take A Chance, It Pays Off, Pt 1_(0)

/ Categories: Anal, Fiction, Transgendered, Transsexual, Transvestite / Anal, Fiction, Transgendered, Transsexual, Transvestite / By

I sat down at a table in the food court of the convention. I was dressed as Emma Frost this particular day. It wasn’t my first cross play. I made a cool $300 of a friend of mine the first time, one who wasn’t convinced that I would do it at a con. My salad in front of me was somewhat unappealing, although I was really only eating it to keep up appearances. Many men had complimented me on the costume, and a few even asked me out that evening. I had denied them, since I wasn’t really interested in going out beyond the convention. A man in a Goku cosplay asked to sit across from me. I didn’t think much of it and pointed at the chair. I, then, noticed the sheer size of …

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Rebecca Chapter 01

/ Categories: Cum Swallowing, Fiction, Transgendered, Transsexual, Transvestite / Cum Swallowing, Fiction, Transgendered, Transsexual, Transvestite / By

My wife Jasmine knew that I was a trannie. She was OK with it when I first told her and even helped me with make-up, clothes, deportment etc. However, as with all these things, I became obsessed with dressing all the time. I even toyed with the idea of changing sex. I guess this all became a bit too much for her and she gradually lost interest in helping me. Our sex life deteriorated to nothing; my fault again as I always wore lingerie to bed and she really wasn’t too keen on touching me, although we were still the best of friends. I began to notice though that she was wearing sexier underwear, not that I minded as I always got a thrill from wearing her used panties, usually with the thought in my …

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Say Hello to Georgette

/ Categories: Bi-sexual, Fiction, Teen Male / Teen Male, Teen Male/Teen Female, Transvestite / Bi-sexual, Fiction, Teen Male / Teen Male, Teen Male/Teen Female, Transvestite / By

My name is George. I’m 15 years old. My parents are divorced. I live with my mother and younger sister. I was painfully shy growing up and I didn’t really have any pals to hang out with so, out of desperation, I started tagging along with my sister Fiona who was two years younger than me but much more outgoing. Fiona didn’t mind because that meant she could stay out later being escorted by her big brother. Fiona liked to meet up with her girlfriends at one of their homes or at the shopping mall. No one else seemed to mind either because I never interfered with their activities. I usually just sat there and listened to them gossip or complain about boyfriends. I liked to imagine I was a sheikh and they were all …

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