Sort by
Relevancy

Free Stories

100%
The Fabulous Alessia Travestita
Alessia is a real transexual. Several of her porn videos are on this site. She collaborated with me in this story. Alessia is a natural blonde haired, brown eyed, mature fifty -five year old Transsexual woman from England. She is tall, very fit, stands 5'11," 36B-26-30 and a slender 133... Read full Story
darrell 2021-12-14 4,323 Crossdresser Blowjob blonde Big Cock domination Mature cum in mouth
80%
TG Girlfriend moves in (part 2)
My wife Lydia and I have been married about 9 months, we have a very close TG friend, Joanne, that lives next door and every once in a while, we get together, and all go out and enjoy. We have had sex together, and when Lydia is away Joanne, and I are together at every opportunity. Joanne and I work... Read full Story
Jon Paul 2022-01-21 3,460 Big Tits Cumshot Bareback Creampie threesome Blowjob Shemale and Girl Guy Fucks Shemale
100%
How it began (1/x)
About two years ago I was in a relationship with a woman that I'd always considered to be out of my league. She was a tall, tattooed lady with black hair, who used to wear incredibly saucy dresses, knee-length boots and flamboyant make-up. Me, on the other hand, I have always been a quite unrema... Read full Story
sissylennie 2022-09-07 4,111 Crossdresser threesome domination mistress Cuckolding Cuckold Sissy
100%
Used in a hotel room
This is a recurring fantasy I have about being used in a hotel room. I’m working on making this a reality but for now this will have to do. I travel a lot for work and end up in many cities across the world. Usually I am out and exploring bars and restaurants. Always ends with me jerking off alo... Read full Story
slvr2291 2023-01-11 4,649 anal first time Big Cock fantasy Surprise
100%
Buffy the Shemale Vampire Slayer Part 5
By the time that Buffy arrived at Rupert Giles' apartment, the former librarian, her ex-Watcher, had just finished reading a new volume of what Edgar Allan Poe, in The Raven, had referred to as a "curious and quaint volume of forgotten lore." He'd just settled the large, leather-bound volu... Read full Story
shemale lover 2011-08-19 3,670 hardcore celebrities shemale
0%
The Surprise Call
"Thanks for the wonder full time we had together last night Army Bear, it was awesome! I hope, we keep in touch as we both agreed," I sent my toy boy an email the day after our Valentines date. I was still thinking about of our hot night/morning together, I couldn't keep him out of my mind... Read full Story
HotVersatileTs 2011-10-04 4,131 sucking domination ts foreplay
66%
Showing Off For My Wife's Pleasure
There I was lying on my back, on the floor of a cheap adult bookstore. All I was wearing were 5" heels, black thighhighs, and a nipple chain. In one hand, I was jerking my throbbing shaved shaft while I was using my other hand to fuck my ass with a double headed dong. Cum was glistening on my f... Read full Story
shemale lover 2011-10-25 5,394 anal asshole shemale
50%
Trying It On For Size
I was twenty minutes early for my one o'clock appointment so I found a shady spot in the parking lot of the upscale chain motel, kept the engine running to power the air-conditioner on the warm Sunday afternoon, took a few deep breaths and tried to relax. My mind wondered back over the series of eve... Read full Story
shemale lover 2011-10-26 7,893 asshole licking sucking
71%
Headmistress' Favorite Sport Part 2
Over the next week the twins trained him further. He was taught how to apply make-up and how to behave in a properly feminine and submissive manner and they trained his movements to be properly feminine. So as not to wear the skin of his ass, the twins introduced a new punishment tool for these trai... Read full Story
shemale lover 2011-12-12 4,890 torture toys bondage and discipline heavy
0%
Headmistress' Favorite Sport Part 7
At the academy Denise and the others immediately resumed their old routines. The training for the second year slaves had started a few weeks before the new batch of sissies arrived at the academy. Not many new elements were introduced in the training as the second year was mostly about perfecting th... Read full Story
shemale lover 2011-12-13 4,613 torture toys bondage and discipline chastity belt
50%
The Greatest Lie Part 6
In my rare moments of leisure in the weeks following my close encounter with death, I had had little opportunity to talk about it. Of course, the police had asked perfunctory questions, and I had testified at the coroner’s inquest, but until my next appointment with Dr. Erika Wright, I had not... Read full Story
shemale lover 2012-01-19 4,550 hardcore erotic encounters fantastic
0%
The Greatest Lie Part 16
As soon as we were safely back in our hooch, I retrieved the iBook from its hiding place under the floor and opened up Spartan's main Excel spreadsheet. I re-sorted the list against the data from the last three weeks of our frustrating field work, by district, language group, age, and every other ca... Read full Story
shemale lover 2012-01-20 5,003 first time femdom crossdressing
50%
The Greatest Lie Part 17
They say that life is about making choices. But we humans don't get to choose the two most important factors in our lives. We don't get to choose our genes, so I got stuck with XY chromosomes. And we don't get to choose our natal families, so I got stuck with my mother and father. My father, Edua... Read full Story
shemale lover 2012-01-20 4,504 erotic encounters fantastic consensual
100%
Case of the Jealous Transsexual Chapter 2
Dee-Dee was becoming a little possessive after the 2 times that we had seen each other. She began calling me everyday, emailing me, wanting to know when will we see each other again and so on. To tell you the truth I had moved on. I had done everything with Dee-Dee that I felt could be done on a phy... Read full Story
shemale lover 2012-03-19 3,321 Group Sex Big Tits Cumshot
100%
A New Girl
Still half-asleep, I purred happily when I heard the curtains being drawn. I could hear the sound of rain beating against the outside of the window, but the poor weather was the last thing on my mind. Still barely able to believe my luck, I slid my hand down the side of my smooth thigh, delighting i... Read full Story
shemale lover 2012-04-05 4,487 fingering oral sex small breasts cum swallowing
100%
Danielle Works a Saturday
It had been a few months since his wife left him. Well "ex-wife" as the divorce had been recently finalized. It was her choice; she walked out on *him*. She said she got tired of "Danielle", even though she was entirely responsible for Danielle's "birth" to begin with. ... Read full Story
shemale lover 2012-06-18 5,634 anal sex Creampie oral sex cum swallowing
85%
A Surprise Stripper for My Birthday
My wife and I have always been a little on the kinky side. We have been swingers for seven years and have done many wild things during this time. Every Friday night we have a thing called dirty night where we go up to our room and watch two of our favorite shows Bliss and Kink. Bliss is a weekly ... Read full Story
shemale lover 2012-07-06 5,153 threesome oral sex cum swallowing pre-op transsexual
80%
Becoming Alanna Part 2
Walking into room number one, she told me kindly to strip nude and climb into the chair. I did as I was told and hopped in to the chair. I fit my feet and legs into the stirrups and she spread them apart exposing my cock balls and asshole. She looked me up and down and smiled "not much work wit... Read full Story
shemale lover 2012-07-12 3,877 sucking Fetish Ladyboy rimjob
100%
A Valentines with a Bang...x
Time had seemingly flown by since meeting the man I was to fall head over heels for on a drunken night in the town centre, the type of guy you would never expect to be dating a transvestite but here I was waking by his side as I had done for the past 6 months or so since we moved in together after m... Read full Story
shemale lover 2012-07-16 3,218 anal sex cum oral sex
72%
For Want of a Heel
"Shit, shit, SHIT." Sally glared at her right foot. The heel of her shoe was broken off, still caught in the chink of the cobblestone walkway she was standing on. She carefully set the bag holding her laptop down and reached down to pull the heel free. "Two hundred dollars," S... Read full Story
shemale lover 2012-11-15 3,485 tranny Cumshot oral sex
93%
Lakeside Awakening
If anyone had told the way I'd meet my soul mate a few years ago, I never would have believed it. It was my senior year of high school and I had recently gotten out of yet another bad relationship with a girl. Lina had been a pretty, chubby blonde with a nice personality but a nasty temper. We ... Read full Story
AlliV 2014-09-02 6,619 tranny ass Teen (18+) Big Cock jerking
45%
Shemale Prostate Orgasmic Bliss!!!!
if she wanted breasts." "Oh no. That's the amazing part. The more I dressed him the more feminine he became. By now I'd moved him her and her clothes into the other bedroom. She wasn't happy with that but we came to an agreement; I'd milk her once a week and she... Read full Story
ProstateMilker 2015-05-01 13,804 Masturbation cum orgasm cumshots prostate
90%
DISCOVERING BLACK COCK
To the greater Boston general public it was simply a small little known quite private night club located in the back part of Roxbury called The Black Rooster Bar. While in local Gay Community circles, insiders called this private by membership only pub, THE BLACK COCK CASTLE! When first learning... Read full Story
CD DIXIE IN NH 2016-05-10 10,216 Big Cock cumming sperm ebony cock
89%
Car Park toilets meet
It was early Sunday Morning , when I had decided to go for a drive into the Lakes , typically soon after setting off I needed the toilets , as luck would have it there was a small village with a car park and toilets not too far off , so quickly stopping I went in , surprisingly as it was quite early... Read full Story
jakuk 2016-10-26 9,483 anal ass fucking cumming casual sex public toilets
100%
The Biology of Music - I fucked my trans substitute teacher
I was never strong in school. I wasn't very interested in what we were being taught, and the teachers liked me enough to not give me too hard a time about it. I attended an all boys school. It was actually quite a religious school which makes this story all the more surprising. I was in the middle c... Read full Story
terrifictim 2022-01-03 3,871 Creampie Guy Fucks Shemale feet licking first time with a tranny teacher student
100%
Chapter 1 - My Cuckold Life
I have a small penis. In fact, I have a very small penis. I’ve been in permanent chastity for over 7 years. My wife and her lovers call it my “caged clitty” and that’s about right as far as it being a useful penis. I suppose I should start at the beginning. I’ve never been much of a man. I’m ... Read full Story
Sissy Annabelle 2022-08-23 6,140 Crossdresser Interracial sissy chastity Cuckold Husband
100%
First work day!
Having just graduated from college in Miami I took up fashion as a career! Impressed? In fact, I managed to land a job as a clerk in ready-made clothes shop. Sounds not as impressive as I’d like to have but that is just a beginning. You think there are no other interesting places in the whole ... Read full Story
shemale lover 2014-05-31 9,107 tranny asshole
89%
He caught me in his wife's cloths
I do odd job's and I was about to do one for my wife's best friend Tina and her Husband Phillip. I went over and looked at the job. I told her it would take several days and that I could do the work while her and her husband were at work. That way I wouldn't be in anyones way. Well the first day of ... Read full Story
shemale lover 2014-06-15 10,067 sucking shemale pounding
100%
Sex Ed Chapter Two
Over another drink, I learnt how David Lawrence had been dressing up as a girl since he was a teenager, always keeping it secret from his family and what few friends he'd had. He was shy around women and sex and had never had a girlfriend, instead he'd buried himself in his studies and dressing as a... Read full Story
shemale lover 2016-03-10 4,890 first time cum fingering
66%
Adventures of Shemale Sandra Part 2
Sandra thought about Jeff all through the next day. He had been her first, and she could still recall their experience as if it had happened only moments ago. She could feel his rough hands on her tender flesh; his sweat falling in beady drops on her soft belly; his stiffled grunts echoing in her ea... Read full Story
shemale lover 2011-09-03 4,388 sucking shemale nipples
97%
Stepdaughter's Transexual Surprise
I've been through two marriages in the past. My first wife died at an early age of 29 from a massive heart attack and my second marriage was a nightmare from hell, that I'm now free of. When I met Jeanie, I knew I had to take it slow and easy. Jeanie was a very nice lady in her early 40's. I myse... Read full Story
shemale lover 2011-12-04 13,560 anal Fetish transexual
100%
TV television
My girlfriend Gloria and I had just moved into an apartment together, having gone out for six months or so, before making the committment. We moved in furniture from each of our apartments, after deciding what would go best in the new place. With the exception of a television, we really had everythi... Read full Story
shemale lover 2011-12-11 5,247 Fetish trans tv
57%
Debbie Part 9
It soon turned out that Debbie wasn't destined to spend the rest of her life as a whore. As she returned to the apartment one night one of Mistress' men was waiting for her. She had only just opened the door, when without a word he cuffed her hands behind her back, gagged her and put a collar and le... Read full Story
shemale lover 2011-12-23 6,396 transgender toys bondage and discipline heavy
100%
Becoming A She-Males Bitch Part 2
After last nights ordeal I was given something to drink and taken to a bedroom upstairs. What I drank must have had some kind of drug in it because I was knocked out. I bet I was asleep in just a couple of minutes. I barely even remember lying down. When I woke up I was naked, sore as hell and fe... Read full Story
shemale lover 2012-01-04 8,828 cum oral domination
85%
The Greatest Lie Part 14
For me, my hometown, L.A., is not the sexy, sweaty night clubs of West Hollywood nor the porn scene of the North Valley. Though I feel more at home there, that side of L.A. is not my home but rather the world into which my transsexual destiny exiled me. Home is the leafy, moneyed boulevards and s... Read full Story
shemale lover 2012-01-20 6,039 cum transsexual fantastic
50%
The Greatest Lie Part 18
They say that prostitution is the oldest profession. I disagree. Some guy must have been a professional hunter to have gotten together the spare change to pay for that first commercial fuck. It's like that chicken and egg conundrum. Eggs definitely came first. Just as mutation precedes evolution, th... Read full Story
shemale lover 2012-01-20 4,193 taboo hardcore femdom
87%
A Picture Perfect Sissy
"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie." Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if what he was doing was okay. He really wanted wh... Read full Story
shemale lover 2012-05-27 10,647 Stockings anal sex Fetish Interracial sissy
100%
Birthday Breaking
I had no idea what my girlfriend had planned for me that day - and if I did, I'd probably still have gone along with it. My birthday wasn't that special an occasion for me. I had no family and having recently moved, I'd no real friends in the city. But Gen was determined to give me a time to reme... Read full Story
shemale lover 2012-06-13 4,451 threesome oral sex strapon
62%
A Sissy's Reward
Every time he does this to me he drives me crazy, keeps me addicted to his hand. I feel my sissy-like penis strain to escape from between my legs. I'm very small, only about 3" when hard. I keep it tucked for him, hold it tight between my legs at all times...except for when he does what he's ab... Read full Story
shemale lover 2012-06-19 5,414 Cumshot oral sex sissy
50%
Alex One: House Sitting for a Friend
Sorry, this is a little rough. I've tried expanding the original version but ... i dunno. Anyways this should be a continuing series of some sort. Alex One: House Sitting for a Friend. By Alex Shouse. My friend Karen had worked her way through a somewhat bitter separati... Read full Story
AlexShouse 2012-07-12 3,895 dildo oral transvestite sissy
85%
A Wonderful Awakening
I woke up feeling groggy, God what a night! I really had to stop drinking so much - it wasn't good forgetting what had happened the night before – particularly when you let your friends take you to the seedier bars in town. Anyway, what on earth did had I drunk? I felt weird as shit and, thoug... Read full Story
shemale lover 2012-07-29 4,889 transformation small breasts kissing
100%
Pleasantly Surprised
It was Friday night and Robert was sitting at home alone. His roommates were both out on dates, and his girlfriend, correct that ex-girlfriend, had moved all of her things out three weeks ago. It had been one of the dullest months in his adult life; four weeks of sitting in front of the television, ... Read full Story
shemale lover 2012-08-31 6,289 Big Tits Cumshot sucking threesome blondie
100%
Transsexual Sisters Chapter 6
Part 6: A Party to Remember MICHELLE AND NICOLE MAKE A CAREER CHOICE After their tormentors were jailed, Michelle and Nicole felt relieved and happy for the first time in weeks. Whether from curiosity, respect or sympathy for their ordeal they became very popular around the USC campus. They we... Read full Story
shemale lover 2012-09-08 4,141 Cumshot sucking threesome Shemale and Girl deep throat
100%
Caught Cheating Chapter 2
By this time, Hailey had taken the bus home and was punching in the code to her apartment building when her phone rang. Removing it from her purse, she answered it. Her friend Samantha was asking if she could go to the mall tomorrow. Hailey said sure but told her that she had to be back before 6 o'c... Read full Story
shemale lover 2012-10-07 4,213 Fetish oral sex cum swallowing jacking
100%
An Empty Hole
"its not working out im breaking up w/ u" The last text he got from his girlfriend that Friday was heavy. It sank, like the hull of a battered battleship, drifting towards the bottomless, cold abyss of his heart. The teen took it hard, harder than most. His emotions flared, rapidly resp... Read full Story
shemale lover 2012-11-13 5,464 tranny Cumshot oral
81%
Bimbo Barbiex
Ooh hiya boys, I'm Barbie Leigh, a naughty little bimbo tranny, 19 yr old, 5'7" tall, blond, blue eyes, slim and tanned with a hot curvy ass. I have been dressing as Barbie since I was probs about 16 and I'm very well versed when it comes to horny guys and how to please them.lolz... Read full Story
Barbie Leigh 2013-12-08 4,328 tranny ass Teen (18+) sucking rimming
86%
My first time as a Femboy CD
My name is Nick aka. Nicole. I am a 20 year old gay femboy crossdresser and this is a little story of how I started dressing to become Nicole and my first sexual experience besides masturbation. I grew up living in an apartment complex with my mother and sister, who was 2 years older than me. M... Read full Story
Nicole_femboyCD 2014-12-03 190,682 first time Crossdresser suck Blowjob oral cd
100%
Claudia Coming out adventure part 1
*Author's Note: This story starts off being told in First person and after awhile the story shifts to third person* Hello everyone, my name is Claudia I am a Cross dresser who one day hopes to be transgendered, although I do not want the surgery, I am looking to eventually live my life full... Read full Story
MissClaudia 2015-01-04 5,931 tranny Stockings suck Creampie ass fucking doggy style Latex
84%
Abi's Virginity taken by Intruders
Abi got very little time to be herself, A closet TV, sharing a small two bedroom flat with a male friend, it was only once every few months or so she got the flat to herself and could dress up sexy and be her proper girly self, and tonight was one of those nights! Although she had no plans to mee... Read full Story
AbiTV 2015-03-18 6,406 Crossdresser threesome sex fantasy virgin
86%
Goth Trans Girl Confession pt1
This is true confession. A journal entry of sorts. Sep. 2009 Anyway, I would say that my family is pretty open, at least compared to most of the families of trans people that I personally know. That doesn't mean that I didn't have a difficult time as far as there understanding when I my... Read full Story
Gothtransgirl41 2017-11-10 14,494 first time Bareback Creampie Blowjob
86%
The Girl Next Door Ch. 01 by derezzed ©
Michael was your average 21-year-old college student. He was on his way home from college for summer break after finishing his finals and looking forward to a few months of relaxation. Driving home Michael reflected on his past three years of college. It had been a great junior year. He met a lot of... Read full Story
StevelovesTgirls 2019-05-27 18,065 Amateur threesome Big Cock shemale + shemale
90%
My first Theesome
I'd been flirting with Clare for a while in work. I always thought she would be one of the girls that would play around in work, but never actually go through with anything. It was a slow day in work and as usual the subject came round to sex. We were having a cheeky conversation about fetishes a... Read full Story
cdleesa 2020-06-01 14,377 anal threesome bisexual forced bi
93%
Virgin Slut Cravings.
There have been so many times that I have had to hide how I felt because I lived my life denying who I was. I was a closet queen who was pretending to be normal. Some might have guessed my secret if they were observant. I didn't do things that other boys my age did. I love hanging out at home like a... Read full Story
Regina10 2020-09-29 8,455 Stockings Crossdresser Big Tits Cumshot Bareback Creampie Blowjob blonde Big Cock Lingerie Guy Fucks Shemale pov
100%
I fucked my personal trainers ass for the first time
I greeted him on my bed in my sheer black lingerie. I knew he’d be nervous, and truly I was as well. We’d spend so much time in the gym together and I knew he wanted me, but taking that next step was sometimes difficult, especially when our relationship was always professional. Posing for him, I r... Read full Story
Madison Heights 2023-05-18 6,960 anal Shemale Fucks Guy Big Cock Frottage
100%
CORRECTION ASSERTIVE WENCH
ASSERTIVE WENCH I caught my live-in partner in an affair and things went awfully as her and her supervisor went into overdrive trying to make every mutual acquaintance believe something perfectly fine and wholesome had led to their affair and my misery. We parted and for a time I stayed to mysel... Read full Story
DRILLMASTER 2023-10-27 5,065 threesome
68%
Extra credit for me
After failing my mid-term exam my day was ruined. I headed back to the dorm crying. Through lunch my friend consoled me and suggested I make an appointment with my professor for extra credit. I called the office of Dr. Writt and was told to show up at 2:00 sharp. At 2:00 I knocked on the office d... Read full Story
shemale lover 2015-06-27 6,540 tranny Cumshot threesome