Transvestite

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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Rachel’s Shaved Pussy F

/ Categories: Authoritarian, Bi-sexual, Coercion, Consensual Sex, Cruelty, Cum Swallowing, Diary, Domination/submission, Erotica, Exhibitionism, Female Domination, Female exhibitionist, Female/Female, Girls domination, Group Sex, Hardcore, Humiliation, Incest, Lesbian, Male Solo, Oral Sex, Reluctance, Stockholm Syndrome, Teen, Teen Female/Teen Female, Teen Male/Teen Female, Threesome, Transvestite, Voyeurism, Young / Authoritarian, Bi-sexual, Coercion, Consensual Sex, Cruelty, Cum Swallowing, Diary, Domination/submission, Erotica, Exhibitionism, Female Domination, Female exhibitionist, Female/Female, Girls domination, Group Sex, Hardcore, Humiliation, Incest, Lesbian, Male Solo, Oral Sex, Reluctance, Stockholm Syndrome, Teen, Teen Female/Teen Female, Teen Male/Teen Female, Threesome, Transvestite, Voyeurism, Young / By

Of course, getting regularly showered with my head-teacher’s jizz didn’t stop my other sexual activities. I was having far too much fun. I cast my net far and wide, finding eager partners of both genders to discreetly share erotic experiences with. Through all of it, Kirsty – beautiful blonde Kirsty – was my confidant. We met regularly to share exciting stories of our latest conquests, stories so exciting that they usually led to our own frantic copulation. I was still a little dependent on her for the use of her shaver, and although she never truly exploited the relationship, the difference in status added a little frisson to our interactions. I got very used to the tangy taste of her juicy pussy. Experimentation was always on the agenda too. Lovers – usually men – would …

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Frank’s Inner Woman

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

Frank’s nuts ached; he had been in and out of at least ten porn parlors around Times Square and had spent upward of $40 on the video peeps. Now he was sitting in a nice cool bar with a martini in front of him deciding if he wanted to do it or not. ‘What the hell.’ He thought and turned the copy of the underground newspaper he had bought to the Transexual/Shemale section and began to read the ads, trying to decide which one to call first. Frank had taken the opportunity of his wife being out of town to visit Manhattan and the porno parlors, telling himself that he wouldn’t visit a shemale prostitute again. But the fever was in him and the martini was lowering his resistance. ‘Of course I was going to …

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2 she males 1 lucky male

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

They didn’t waste anytime. As soon as the 3 of us were through the door they went to work. They were eager. One in front of me and the other behind. This is how it would be all night, me the filling to their sandwich. The one in front had her hands caressing my lower back and butt cheeks. The one behind had her arms around me and her hands over my lower abdomen. Her palms brushed over my abbs and her finger tips gently pressing into my navel. She kissed my neck and jaw line from behind. I loved that. The one in front was kissing me hard. We were mashing our lips and tongues together. The one behind was pulling my mid section back into her. She pushed her crotch into me. I …

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Growing Up Chapter 11

/ Categories: Anal, BDSM, Bi-sexual, Diary, First Time, Male / Female Teens, Teen Male / Female, Threesome, Transvestite / Anal, BDSM, Bi-sexual, Diary, First Time, Male / Female Teens, Teen Male / Female, Threesome, Transvestite / By

Sophomore year. I move back into a shared room with the same roomate. His regular absence on weekends is convenient. Alexa stays in the apartment with Chelsea and another girl but Shelby comes back to campus and the dorms… and the trysting room. I am Cool Joe Sophomore on campus. I get lots of hugs and attention from the sorority sisters. People look at me like I’m some kind of stud! I’m updated on what everyone did over the summer. . . . . . Shannon sees me. “well hello beautiful boy. Did you have a good summer?” “I surely did. Are you still a virgin?” “Of course sir! And I’m engaged!” She shows me a huge ring. “Wedding is in June, you’ll get a save the date notice.” “You think that’s appropriate? Inviting me?” …

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My little secret 2

/ Categories: Anal, Bi-sexual, Enema, Fantasy, Transgendered, Transsexual, Transvestite / Anal, Bi-sexual, Enema, Fantasy, Transgendered, Transsexual, Transvestite / By

Katelin and I broke our kiss and looked over towards Jim. He was sitting in one of the kitchen table chairs, boxers down to his ankles stroking his cock. “Don’t my girls want their morning milk??” he said again. Katelin led the way as I followed, getting down on our knees we started to pleasure our daddy. Katelin started licking his cock, getting it nice and wet. Taking it in her mouth, and going down about halfway. I started licking and sucking on his balls and ball sack. From time to time I would lick under his ballsack, giving him a quick fluster. “Hey Ashley, come here and kiss me” Katelin said. As I moved my head up she kept his cock inbetween us. We wrapped our lips around the sides of his cock, trying …

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t-girl girlfriend

/ Categories: Bi-sexual, Transgendered, Transsexual, Transvestite, True Story / Bi-sexual, Transgendered, Transsexual, Transvestite, True Story / By

I have stated in the past that I am disabled and unable to dress up anymore because I cant get out and buy new outfits after my ex destroyed everything. well i was able to sneak out and finally after 5 years buy a pair of panties. I was working a temp job at the local mall and wore them to work when i bought them. there was a store close to where my store was that let us use the restroom and i headed over there. I didnt notice they had a new girl working the counter til i got there. asked if i could bathroom and went to the back room. finished and it was time to close up my store. I rushed through closing so I could go talk to the new …

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Sometimes short for Samuel pt. 1

/ Categories: Anal, Bi-sexual, Blowjob, Fiction, School, Teen Male / Teen Male, Transvestite / Anal, Bi-sexual, Blowjob, Fiction, School, Teen Male / Teen Male, Transvestite / By

Sometimes that’s short for Samuel I’m Sam. Sometimes that’s short for Samuel, A slight young man, trim and clean, round soft features and full lips framed with shoulder length brown hair and bright green eyes. I’m a short 5’9” and a bit of a slouch, so I come across as very short. I was never very athletic so I didn’t have much muscle tone, but I keep fit skating and playing hacky sack with my small group of oddball friends. I keep to the skater look mostly, layers of t-shirts and skate gloves, torn up black jeans or tactical cargos, and either skate shoes (I LOVE my Vans but I’m usually rocking DCs or Etnies these days) or combat boots. Punky bracelets, some chains and a bit of eye liner complete something of a look. …

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Camming Down the Rabbit Hole Ch10

/ Categories: Cum Swallowing, Exhibitionism, Fiction, Masturbation, Pegging, Transgendered, Transsexual, Transvestite / Cum Swallowing, Exhibitionism, Fiction, Masturbation, Pegging, Transgendered, Transsexual, Transvestite / By

As the sun beamed in through a gap in the curtains my now familiar morning wood strained at the silk of my nightwear. How was it that no matter how hard I came the night before it would wake up eager and ready to go. As had become customary my mind would be filled with the events of the previous night, which only heightened my state of arousal. One thing which did differ from the previous mornings was my sore throat. No doubt a result of my getting a little carried away although its scratching as I swallowed some fresh water easing slightly, I smiled and remembered with pride what I had achieved and the results of my dedication. Coughing a little I could clearly hear my voice was a little horse, maybe not croaky …

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Realising Our Fantasies Together part 2

/ Categories: Anal, Authoritarian, Discipline, Domination/submission, Fiction, Transvestite, Wife / Anal, Authoritarian, Discipline, Domination/submission, Fiction, Transvestite, Wife / By

“Steve, come in here now!” Two weeks had passed since my first strap-on session with Maria, and since she had fucked me with it a few times, but she had never let me take off the cock-cage in those two weeks. She was gradually taking her dom role more and more seriously, to the point where she had ordered a black vinyl outfit just to push the point home for me, and it was that same outfit I was looking at as I entered the bedroom. She was standing there, her legs akimbo, letting me see her lips hanging down softly, slightly moist. Her tits were spilling out of the top of the outfit, and she had her hair tied into a tight ponytail, a sliver of it hanging loose on her right temple. My …

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Summer vacation changed whole life pt2

/ Categories: Anal, Bi-sexual, Body modification, Cum Swallowing, Transgendered, Transsexual, Transvestite, True Story / Anal, Bi-sexual, Body modification, Cum Swallowing, Transgendered, Transsexual, Transvestite, True Story / By

From that day I felt differently I wanted to be dressed like a girl I dreamt sucking cock and being fucked . It has been a week and I could not resist any more by luck sis has gone out with friends for a week and aunt have gone out to buy some thing in the evening. I dressed up as a girl and hid some of my clothes in the front garden to change when I return home late night, I messaged my aunt that I was going out and will be back late night so do not wait for me and went to pub near by to have some sex. An elder guy offered me drink and asked me for some fun and he took me to a hotel . he locked the …

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