Sort by
Relevancy

Free Stories

94%
New Girl in Town
Margo sat next to me in the coffee shop late that Saturday afternoon. His real name was Mark, but he was one of the loveliest Drag Queens in New York City. I had been dressing secretly at home in my mother’s and sister’s clothes for just over three years, but at 18 years old, I had never... Read full Story
shemale lover 2019-06-04 10,034 anal shemale oral sex
38%
From Gloryhole Peegasm to Shemale
I was in a porn video booth. I young guy stepped into the next one. I was already jerking my small dick, but he didn't even pull his pants down. He asked me if I wanted my dick sucked. Actually I think he said something like, "hey, let me suck your dick." Recently I had let some weird, ... Read full Story
shemale lover 2011-08-18 16,425 asshole shemale jerking off
75%
by a Shemale Part 3
I woke up the next morning not sure what just happened was real or if I just dreamed it than I looked around. I was laying naked in this mammoth canopy bed the bed spread and canopy were both pink and feminine and I realized it wasn't a dream I couldn't believe I was begging to be fucked. ... Read full Story
shemale lover 2011-08-29 4,427 Cumshot asshole fingering
100%
Tgirl Van Sex
Pulling up to the curb near the bookstore one recent night, I happened to notice a nice looking custom van drive by very slowly. Looking intently at the driver as it passed by, I noticed that the driver was a very sexy looking woman, and she gazed at me intently as she passed by. The van pulled up t... Read full Story
shemale lover 2011-09-10 4,881 asshole oral massage
60%
Susan's First Time Part 4
The shadows of late afternoon crept across the city when Susan paid the cabbie off. Why had 'he' wanted her to come down to this neighborhood? She looked around with apprehension at the garish lights of bars and adult bookstores flashing in the growing darkness. One or two streetlights flickered on ... Read full Story
shemale lover 2011-10-14 3,086 Small Tits shemale massage
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 5,388 anal asshole shemale
75%
Old Folks Part 2
It had been eleven months since that day when I arrived at Honey and Frank's house. It was about 1am at night as I stood in a quiet street waiting for Frank to pick me up. I had just finished with my last client for the night a good blowjob with him ending up cumming on my face. I was touching up my... Read full Story
shemale lover 2012-01-10 6,858 transsexuals erotica romance crossdressers
91%
Panty Town
Chapter One -- Jamie Jamie Sanders did not think he was a sissy. Growing up, he played with trucks and showed his innate male aggression though soldiers games with the other boys. He climbed trees and watched baseball with his Dad and brother. Unfortunately, by the time he was in eighth grad... Read full Story
shemale lover 2012-01-29 19,359 Big Tits sucking ass licking fucking
100%
A Butterfly Emerges
It wasn’t my fault that my parents were small people and passed their genes on to me. However, it was a curse that I was forced to live with during my formative years. Sports like basketball, football and baseball were out of the question and I felt alienated from other children my age. My ... Read full Story
shemale lover 2012-02-09 3,301 Stockings sucking cum facial
100%
A Night Out To Remember
A night out with Liz and Sue I had known Sue for almost five years but had known Liz for a lot longer. We had met while she was still at school although I was four years older we still became good friends. After she left school I helped her with her college work and more importantly when she need... Read full Story
shemale lover 2012-04-20 4,045 Cumshot oral sex crossdressing
100%
Gregs Girl
The woman walked throught the theater casually, her long black hair swingin behind her. Tall and slender, she looked like an exotic model. Even inthe darkness, Greg could make-out a very pretty face, olive skin and bright red lipstick. She walked passed Greg's row and his head followed as he c... Read full Story
shemale lover 2012-05-10 2,772 deepthroating huge cock rimjob
100%
Danielle's First Meeting
Daniel stood on the front porch and waited for his date to arrive. Well, Daniel at this particular time was actually Danielle. You see, Daniel was a crossdresser. Danielle was his female alter ego. He was 37 years old, medium build, average you might say and stood 5-feet-10-inches tall, weighing in ... Read full Story
shemale lover 2012-06-18 4,259 Stockings Crossdresser Cumshot shemale oral sex
100%
Caught by Neighbour Chapter 2
- 1 - The next day I woke to the sound of birds outside, and sun streaming through the windows. It was Sunday, and normally I'd have been up and about early with Sam. But with her still away, I'd slept in late. I lay in bed, unmoving, stunned by the previous day's bizarre events. I scarcely belie... Read full Story
shemale lover 2012-06-20 4,012 Stockings Crossdresser anal sex Cumshot
90%
Caught by the Lodger
Having split up with my girlfriend about six months before, I was getting a little bored of living on my own. I'm a 29 year old guy living in South London and I thought it would be a good idea to get a lodger. I had a spare room that was empty, the company would be good and the extra money would com... Read full Story
shemale lover 2012-06-22 5,607 shemale oral sex Sex Toys strapon
100%
Ellen's Candy
Sometimes I get in the mood to suck a dick but I’ve never considered myself gay. I’m @ the very least bisexual but I don’t like to limit myself to that either because I think it restricts my sexuality. I get turned on watching all types of sexual situations that you could think of;... Read full Story
shemale lover 2012-06-23 4,584 Cumshot shemale cum swallowing mouth fucking rimjob
100%
A Special Friend
I met Charlene in my freshman year of college, about eight years ago. Back then she wasn't what I would consider very attractive. She was kind of tall and had very little curves to her body. Her hair was straight and un-styled; she had a flat chest, wore black rimmed glasses and had very oily skin. ... Read full Story
shemale lover 2012-06-27 3,174 anal Cumshot shemale oral
87%
Uncles Lessons
In '91' during my senior year of high school my folks split up. The whole thing was a mess, with me being sent off to relatives while my mom took my younger siblings to the gulf coast to stay with her parents. They sold the house and Dad moved to be with his new future 'ex-wife' outside of Dallas. ... Read full Story
shemale lover 2012-09-07 6,139 big dick Blowjob fingering ass fuck
100%
Angel of Mercy
Angel stood at her kitchen counter flipping through a massive amount of what was quickly appearing to be no more than junk mail. She was just about the toss the whole lot into the trash can when one envelope caught her eye. The envelope was made of an off white paper that had an unusual texture to i... Read full Story
shemale lover 2012-12-03 5,126 sucking shemale orgasm
100%
The Society
I met her during the summer. I was only nineteen and working to save some money for college. I had been raised by my grandparents who had both passed away over the past year. After the burial costs I was far from wealthy. My parents weren't around so I was on my own at a young age. I had moved a cou... Read full Story
shemale lover 2013-01-10 17,279 Crossdresser sucking Big Cock ass licking big boobs
90%
The Perfect Choice
Andrew had moved in with Hannah a few short months ago and so far everything was going just the way she wanted. She was an endless tease; wearing short skirts and dresses when they were out during the day or tiny shorts and vest tops when they were at home together. She did everything she could to t... Read full Story
shemale lover 2013-01-10 6,508 hardcore Shemale Fucks Guy Blowjob ass fucking domination
100%
Clara Bow's Academy for Ladies
Peter had had no choice in the matter from an early age. As he car drew up to the huge ivy clad castle-like building, having entered through electronic gates in a ten foot wall, he felt doomed yet excited. His cock was erect in the tight panties his Stepmother has chosen for his introduction, his an... Read full Story
shemale lover 2013-03-27 5,025 Teen (18+) Small Tits shemale public softcore
94%
My Shemale Fantasy
Allow me to introduce myself, i’m a young European man, in my early twenties, writing my first erotic story. This has been a fantasy all my life, it probably will remain a fantasy, but that doesnt mean i cant write about it. Ever since i was old enough to realize my raising sexual interest and... Read full Story
Jakester 2013-04-10 31,674 first time Creampie Shemale Fucks Guy ass licking virgin
88%
Making love on the beach
= First = My name is Lely Bella Calistia, I'm an Asian shemale, I'm 27 years old, and I now live on a very beautiful island in Southeast Asia, I have only been here for 2 years and have a nice new life. I have a friend when I was a child, and we are good friends until now, but unfortunately wh... Read full Story
Bella Calis 2018-10-22 6,167 Blowjob Asian gangbang Guy Fucks Shemale
100%
Lady In The House Ch. 07
A story by MicheleNylons (Carmel and Charlotte want theirs.) From Part VI "You look gorgeous Michele," Carmel whispers through the bars. I wondered if she had read my mind when I was standing in front of the mirror admiring myself. "Well, I have to say you girls are looking something spe... Read full Story
✘Transensual✘ 2019-02-25 3,345 Crossdresser domination prisoner shemale lesbians Prison Bitch
100%
Doctor's Orders
Ever since he was a small boy, James had hated going to the doctor’s office. As he walked through the doors towards the reception desk he felt his stomach tightening, and as he stood there waiting for someone to check him in, he shuffled nervously on his feet. A pretty blonde receptionist walked ... Read full Story
reasonman 2019-08-02 22,597 first time Blowjob ass licking Guy Fucks Shemale foot fetish doctor cum in mouth
100%
ROBERTO’S SECRET by Spanky De Bautumn
Cody Daniels was only trying to help her country; she never dreamed things would come to this. She was patriotic and felt compelled to do whatever asked of her to aid in the capture of the terrorist known only as "Roberto". But lying in his bed, bound and gagged, Cody wondered why she let herself go... Read full Story
SpankydeBautumn 2021-01-22 4,879 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale
100%
First Encounter (Mexican Travesti)
I grew up near the U.S.-Mexico border and am ½ Mexican Hispanic and ½ Anglo (white). I visited Nogales Senora on the Mexican side on and off during my teen years. As a young adult, I was fearless and sometimes went across alone to visit the strip clubs, get a cheap lunch, or look for Mexican sweetie... Read full Story
AllenB 2022-09-07 6,821 anal sex Shemale Fucks Guy Blowjob mexicana cum in ass first time with a tranny
100%
New Game by Jordan Skythe
New Game Alan tossed his game controller, then reclined on the bed and sighed. “I’m bored.” He nodded in agreement. “So am I.” He wasn’t, but wanted to see where the declaration could lead. “We need to do something new.” He felt his breathing increase, wondering if this was the moment he could... Read full Story
AuthorJordanSkythe 2022-01-24 2,112 first time Stockings Crossdresser Bareback Uniform seduction Lap dance
100%
The 10 in Bay 10
On the USS Corinth, there were 10 bays - the first bay was for the captains and their personnel, the second bay for first class, the third bay for business, and so on. The back bays were reserved for the ship’s workers. All the way back in bay 10 was the engineering bay. Those in bay 10 rarely inter... Read full Story
sevon 2022-10-03 4,757 Cumshot Bareback Big Cock Futanari shemale + shemale
100%
Alessia and the Twins
Alessia and the Twins When the politician David Smallwood awoke that morning his thoughts immediately turned to Alessia, and he started to daydream about her, as he was wont to do now. He had several meetings scheduled for that day, including a rally promoting restrictions on gay and trans-gender... Read full Story
Alessia Travestita 2023-07-21 5,259 Crossdresser Blowjob Big Cock Shemale and Girl shemale fucks female
100%
Bimbo Bombshell - Chapters 1-2-3
Bimbo Bombshell - Chapter One: Singled Out! Even though it was Friday, the bar wasn't particularly crowded that night. I never knew what hit me. This Gorgeous Blonde bombshell, starts flirting with me right a my table. I found myself wondering why this glamorous beauty, had chosen me. I was... Read full Story
Hardrock51Fifty 2024-06-23 4,641 Stockings Big Tits Shemale Fucks Guy Fetish Blowjob blonde domination Guy Fucks Shemale blonde shemale PDA Public Displays of Affection
82%
My beautiful tranny!
This guy picks up a girl and takes her to his place. Can you imagine his surprise when he finds out that this girl has a dong? Hi! My name is Andrew! I’m a 5.4 feet tall, with some cute beer belly, crew cut light brown haired guy, blue eyes. My friends say I have a big noseJ but it’s ... Read full Story
shemale lover 2014-04-27 7,203 sucking shemale cumming
92%
A new girl around!
You know, things, I’m gonna tell you about started when I was a teen. I was like every teen guy, I loved web porn, looked at porn on the internet, surfing porn sites through the web space and masturbated a lot. I loved and now love to watch lesbian porn: it was so hot watching girls having sex... Read full Story
shemale lover 2014-05-21 18,555 shemale fingering cumming
97%
The Roommate
I’ve been rooming with Bob for two years now. He and I met about 5 years back, while we both worked at the grocery store to get through college. We were good friends from the moment we met. We had similar interests, were both outgoing, good looking, and hated working at the grocery store. ... Read full Story
shemale lover 2018-02-26 21,305 suck Creampie ass licking
85%
A Girl Called Eddie
Carrie had always treated me like her little sister, even though we were only third cousins. Though she was only two years older than I was and not of exceptional physical stature, I had allowed her to dominate me for as long as I could remember. Not that she was exceptionally cruel or abusive in an... Read full Story
shemale lover 2011-08-14 5,441 anal sex asshole Lingerie
84%
Fucked by a Shemale
My names - and I would like to tell you about a very sexual experience I had recently. First I would like to tell you I’m 30 years old and never had a gay experience, until now. It was a Saturday night, me and my brother were round the local town, after a few too many beers my brother met a bi... Read full Story
shemale lover 2011-08-18 169,203 first time shemale cum
71%
Buffy the Shemale Vampire Slayer Part 2
Buffy waited until twilight, hiding out in her bedroom, as she tried to come to terms with the bizarre fate that had befallen her, thanks to the Feral demon's bite. It wasn't easy, psychologically, physically, or otherwise, to have gone to sleep a girl and to have awakened a hermaphrodite. She wasn'... Read full Story
shemale lover 2011-08-19 4,230 hardcore celebrities shemale
100%
Fancy Dress Erotica
It was Tony's eighteenth birthday and his parents had decided to throw him a fancy dress party. For a laugh, myself and some of the the other guys at the running club decided that we would dress as tarts for the night. My name is Andy by the way. I am 16 and have been running for the SNCC Running... Read full Story
shemale lover 2011-08-24 4,617 shemale crossdressing genderbending
85%
Father In Law Shemale Adventure
My wife's parents were visiting LA from back east. We live in a small one-bedroom apartment in the valley. She wanted them to stay with us but we didn't have room. They got a room in West Hollywood. My wife and her mom had gone shopping for the day. I was supposed to be at work but at the last momen... Read full Story
shemale lover 2011-08-26 5,818 Cumshot asshole fingering
100%
First Time With Shemale
For as long as I can remember, I've preferred my chicks with dicks. There's something about a sexy babe with perfect makeup and hair and a cock that just turns me on. Maybe that makes me a pervert - I don't care! I remember I was just out of high school, 18, the first time I made it with a tranny. S... Read full Story
shemale lover 2011-08-26 3,793 anal Creampie shemale
100%
Sudden Shemale
I woke up from the anaesthetic, still very groggy and uncertain. I couldn't remember anything, and my head and body ached terribly. I glanced around, trying to lift my head off the pillow, but it just didn't work. After a few minutes, I tried again, and this time I managed to stand up. I was ... Read full Story
shemale lover 2011-08-30 5,750 asshole pussy Big Cock
66%
Charisma & Tiffany Part 2
Tiffany's six cocks filled Charisma's six cunts and, although the sorceress was on top and, therefore, able to move faster and with more force and agility than the supine shemale, Tiffany, nevertheless, felt overwhelmed by the welter of sensations that had, as it were, laid siege to her consciousnes... Read full Story
shemale lover 2011-09-02 2,987 asshole shemale domination
100%
Adventures of Shemale Sandra Part 1
His name was Phillip. Or at least it had been. Honestly, he wasn't sure who he was; all he knew was that what he had done two years ago was what he thought was right. This was the lifestyle he wanted. It should be said that Phillip has always had strong female influences throughout his life. He a... Read full Story
shemale lover 2011-09-02 3,748 anal sex asshole cum
100%
Shemale Adventure
You: early 20's, tall boyish good looks with a lean and muscular body. Dressed in tight leather pants, from behind your tight buns are revealed by the shiny black leather, as are your cock and balls from the front. You are wearing black leather boots and a denim shirt that refuses to hide your stron... Read full Story
shemale lover 2011-09-06 4,355 asshole Lingerie bisexual
100%
Allison is Born
What a wonderful day this is. This is the first day of my new life but before that I should give you some history about me. My name is Allison, I am a 24 year old male that lives in a small town in Ohio. My father died when I was very young and I was raised by my mother. I guess you could say I am i... Read full Story
shemale lover 2011-09-24 3,625 Stockings Big Cock cum stroking
93%
The Babysitter's Secret Part 2
Two months had passed since Jenny and I had first made love on that fateful, snowy night. At least once a week, occasionally many more, Jenny and I had found time to be alone and indulge in our secret affair. I had never believed any sexual experience could be greater than our first time together bu... Read full Story
shemale lover 2011-10-24 6,673 Stockings shemale oral sex bisexual
75%
Pleasure in the Park
I'd ridden that ride a thousand times.... But I just kept getting back into that huge queue line. I was at the local theme park riding the newest addition to the ragtag assembly of attractions, the Master Exploder. It was the craziest coaster I'd ever dared step my foot into. Everyone else loved ... Read full Story
shemale lover 2011-10-26 3,317 first time Stockings cum
69%
From Mob to Shemale
Two years ago, I was a member of the Ciccio family in Chicago. I wasn't very high up in the organization, because I wasn't Italian. I had made my way up through the ranks, however, and was making a pretty good living. I had everything I wanted, got all the girls I wanted, and did just about ... Read full Story
shemale lover 2011-10-29 10,507 orgasm facial oral sex
100%
Sweet Sherri
"The fuck you want," the girl hissed through her teeth. Well, it's hard to say. For one, this was the one night of the week at the particular club that was tranny night. Unless the lucky woman was either a straight freak or had been exposed to the scene, there weren't too many people wa... Read full Story
shemale lover 2011-10-31 5,530 Big Tits transsexual big ass
71%
A Night of Makeup, Cock and Cum - froam Annamalice
It was all I could do not to accept. After all, it's been a fantasy of mine for years. When given the opportunity, I had to go for it. I had been surfing the internet for crossdressers, shemales, transvestites and transsexuals. The idea of a hot woman with a cock had always turned me on. Further, I... Read full Story
shemale lover 2011-11-21 5,128 shemales Group Sex Fetish
100%
Mistress Jasmine made me a slave forever
I should have been honest. I mean I should have known that lies have short legs and now they had caught up with me. The worst was I had not only lost my place in my bed but had also lost my place with my wife. Somebody else occupied these places now. Let me tell you how everything went. More ... Read full Story
shemale lover 2011-11-26 11,405 Big Cock orgasm domination
50%
Sadopsychorama
He liked Clyrissa. She was a cock-hungry female if there ever was one. At 5'5", she had platinum blonde dyed hair, big tits, and a tight waist. She was a hot lay. But the best thing about her - the thing that stiffened his cock whenever he saw her was the fact that she was 53 years old. Somethi... Read full Story
shemale lover 2011-12-24 3,768 Fetish shemale anus
87%
They Were Right
They were my friends, but I'd had sex with both of them. Not at the same time, but I had dated the one for a month and just started dating the other. So, although the thought had never crossed my mind before, I found myself dressed up as a girl for Halloween. After we had partied at a few clubs and ... Read full Story
shemale lover 2011-12-29 5,799 shemale Big Cock porn
100%
Marilyn's Family Reunion
The warm humid September air blew through the windows of the speeding silver Nissan Pathfinder as it cruised along the Belt Parkway. With the Marshall Mathers LP blaring out the stereo, Sharilynn whipped her SUV along as the wind whipped her ponytail and her plain white t-shirt. As little Mai lay sl... Read full Story
shemale lover 2012-01-02 4,437 sucking Shemale and Girl cum swallowing
100%
Special Shemale Fun
Everyone in the hallway jumped slightly, turned and quickly looked at the tall girl near the sound of the slamming locker. Satisfied that there was no crisis at hand, the kids at the school mostly went about their business. Of course, there were the few admirers that glanced at the girl at the locke... Read full Story
shemale lover 2012-02-06 5,213 sucking shemale massage
60%
A Trans-Lesbian Montreal Love Affair!
St. Catherine’s Street in downtown Montreal is one of the world’s most vibrant streets and entertainment corridors. Known for its energetic, exciting and often crowded venues, it is lined with quality restaurants, theatres and many popular nightclub establishments. St. Catherine’s ... Read full Story
shemale lover 2012-02-12 4,952 Big Cock oral orgasm lesbian