Sort by
Relevancy

Free Stories

50%
I am Baaack! Part 5
Joan hung up the phone. One of what she liked to think of as "Dr. Adkin's Rules for Having It All.And Keeping It" was, "Always expect the unexpected", but this had thrown even her for somewhat of a loop. Rose was still alive! Not only alive, but here in Chicago and wanting to mee... Read full Story
shemale lover 2011-12-15 3,155 crossdressing erotic encounters fantastic
50%
Judi's Fantasy
When I got home I could hardly stop thinking about the wild night with Judi. I didn't even care if my wallet was empty. I was going to work plenty of overtime that next month to make up for it. Judi gave me specific orders not to call her but she would call me whenever she was not busy. About two da... Read full Story
shemale lover 2012-01-02 5,926 anal sex dildo orgasm
100%
Emily and Steve Part 8
I didn't even see it coming. I should have. I should have known that life just can't work out exactly like you would expect. Instead it has to throw you curve balls, put you back on your heels, and then put the next one on your chin. The first few months after Emily moved in, things were going gr... Read full Story
shemale lover 2012-04-07 3,160 Crossdresser Fetish blonde
91%
A New Year's Resolution
I'm not gay (laughing), with that said, I have seen some very good looking, uh, guys. Okay, go ahead and laugh. You see, toward the end of this past summer (August 2011), my wife and I visited an old friend of mine in Pattaya, Chon Buri, Thailand. He's a former Navy Seal. I'm a former Army Ranger as... Read full Story
shemale lover 2012-04-16 7,682 anal sex cum oral sex
100%
European Vacation
I was 18 when I first went to Europe. That month would change my life. My parents had died when I was five, and I was raised by family friends; they also controlled my trust fund. It's not a coincidence that I went to Europe just as I came into control of the money. I loved my foster-parents, but... Read full Story
shemale lover 2012-04-21 3,818 anal sex cum oral sex sissy
87%
The Neighbour
I made my way up the driveway, after having a few with the guys to end off the week. I was in no hurry to get home because I knew there wasn't anything going on tonight. The wife was out of town for the weekend and the other guys had stuff of their own going on. So I made my way up the rest of the d... Read full Story
shemale lover 2012-12-21 9,806 Teen (18+) Crossdresser sucking Sex Toys handjob
95%
How I became a cute femboy CD part 2
The game of husband and wife Kevin and I played went on for a little over 2 more weeks before we decided to go even further, I say we but it was Kevin who seduced me into it. We got together in our game as much as we could and it was a lot. I would always dress for him in various outfits and my ... Read full Story
Cute_Femboy 2016-04-05 12,245 first time oral sex nipples crossdressing cd sissy
94%
SISSY RULES!!!
There are a few things a sissy must understand in order to attract, and then keep, her man. Let’s look at them, these Sissy Rules. (✿◠‿◠) 1. Men are superior to you. This is rule number one for good reason: it is a simple statement of fact. It is so important that many questions that a potent... Read full Story
KittyHot 2021-06-18 8,245 Crossdresser Amateur Fetish submissive feminization sissy submission femboy hypno beta obedient
57%
Ambers torment
It seem to be the typical day for Amber as she entered the home of Master. The usual early wake up and long drive down to his house seemed nearly routine though, the last visit was a few months past and the girl was anxious for what was to come. Although, her expectations were not different from any... Read full Story
shemale lover 2014-04-19 7,272 shemales Fetish bdsm
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 21,314 suck Creampie ass licking
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 16,437 asshole shemale jerking off
80%
Summer Fun
Living with your parents is exceptionally annoying, especially when you're 26 and have a fetish for crossdressing. It kind of hampers your "need" for putting on slutty outfits and parade yourself in front of a webcam with a pink-glass buttplug up your ass and a giant rubber cock vibrating ... Read full Story
shemale lover 2011-08-20 5,157 anal sex ass licking crossdressing
75%
Rebound
My story is nothing new, like most girls who used to be boys I knew from an early age that I was different to all my school friends. My dad was a thug of a man, who enjoyed the physical battle of the rugby pitch as much as the post match booze up, but I took after the mother who died giving birth to... Read full Story
shemale lover 2011-11-25 6,220 anal Creampie oral
100%
Becoming Marie
I'd had always liked dressing in women's undies from an early age. It was usually my older sister's panties and skirts whenever possible. When I finally left home at eighteen and moved into an apartment in the town center, it really took off. I had had a few encounters with a few guys, mainly glory ... Read full Story
shemale lover 2012-03-22 3,506 anal sex sucking Fetish wanking crossdressing
100%
A Very Happy Holiday To Me
I don't know if it was a dream or just something that happened but it was Christmas and I felt sore and achy all over but with a wonderful feeling none the less. I am a crossdresser who is trying now to discover and explore his female personality and can now happily tell of who I was in the past,... Read full Story
shemale lover 2012-04-03 2,962 Creampie oral sex cum swallowing crossdressing
100%
First time out of the closet
I had always been more than a little interested in the world of cross dresser and she males. Since I was a teenager I had experimented with cross dressing. Usually just small stuff. As the years progressed whenever I was out of town on a business trip I would sometimes dress up in my hotel room. I a... Read full Story
shemale lover 2012-04-19 3,307 anal Creampie oral crossdressing glory hole
100%
Eve Quest Part 3
Sometime during the night I was released. That exquisite pain at the point my limbs were release must have dulled my recollection of the events. I'm reasonably sure I was given the Toilet command and I hope I did a good job. In any event, I was still on the bathroom floor when I heard my mistresses ... Read full Story
shemale lover 2012-04-21 4,409 transformation oral sex cum swallowing
50%
A Revenge Fuck
It had been a long day. I had fought the traffic after a miserable week to get home early and surprise my wife for what was to be a romantic weekend. But as I pulled up to the house my heart sank. I saw a bright red motorcycle in the drive way and something inside told me, "This isn't right!&qu... Read full Story
shemale lover 2012-06-03 11,161 shemale oral sex Interracial
100%
A Schoolgirl Story Chapter 2
I must apologise for the amount of time that it has taken for the second chapter of this story to come out. I have to admit that I had kind of abandoned it, but all your lovely feedback comments made me decide that I couldn't leave this one hanging. So thank you to everyone who wanted more of Wendy,... Read full Story
shemale lover 2012-06-05 8,511 Group Sex Cumshot oral sex assfucking
100%
Alex Two: The Next Time
Part Two of ??? (there is another series I'll start too, Hopefully its not too repetitive and my fetishes aren't showing too strongly. heh. That is sort of a prequel to this, I guess. I had forgotten about it till just now when I found it in a misnamed folder.) Alex Two: The Next Time.... Read full Story
AlexShouse 2012-07-12 3,222 tranny Crossdresser Masturbation
75%
Frat Party
It was my first frat party. I had no idea how I wound up there. The liquor was flowing hard, and the rooms were packed. The guys were all football stars, hooting and chugging, and the girls were all skanks. I'm used to thinking of girls as dignified, delicate creatures. But these girls were screamin... Read full Story
shemale lover 2012-11-24 5,101 big dick anal sex Creampie
100%
Anastasia's Life
Chapter 1: Humbling Beginnings My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember, not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barb... Read full Story
shemale lover 2012-11-26 7,197 Fetish cock sucking crossdressing
76%
She didn't see it coming
I had seen her at a stop light while driving around looking for a spot to eat. She drove a red Pontiac Sunfire, the convertible kind that no self-respecting man would be caught dead in. She was gorgeous, at least from what I saw from my elevated platform of the SUV I was driving. She was petite, ... Read full Story
shemale lover 2013-07-17 5,131 hardcore oral sex big boobs kissing shemale sex
33%
Sleazy Walking
I was bored one night, and began to email wanted ads on craigslist to see who was hosting in my area. I lived in spokane, wa at the time in the east central area, sorta behind the fred meyer. This night was boring, my friends had left a while ago with their girl friends, jealousy began to set in. I ... Read full Story
Ville Lohner 2014-05-15 2,922 Stockings Crossdresser Amateur suck Lingerie
94%
Penitentiary Pussy-Butt Boy
Hi: My name is Bobbie. Would you like me to tell you how I became a Penitentiary Pussy-Butt-Boy? Well, it all started with a robbery gone wrong. I wasn’t even in the bank when the guard got shot and I still got almost as much time as the others. So, not long after the trial I was sent to the sta... Read full Story
NaughtyBobbie 2014-04-11 15,046 hardcore suck Big Cock Interracial crossdressing
73%
How did i get here?
I’m a thin, pretty good looking 30 years old guy, living with the girl of his dreams. But a girl without a cock is no longer enough now. All my life I considered myself as a straight guy, even if sometimes duchbags at school called me a fag. I only dated girls, prefered long love stories over on... Read full Story
slavetocock 2015-09-25 6,288 sex toy Crossdresser feminization slave sissy
85%
My dream pt 2
A few hours later I woke up and realized that I had fallen asleep. Sydney must have also fallen asleep as she was still in my arms. I tried to get up with out waking Sydney but that wasn't possible. She woke up and quickly put on her nightie so she could walk me to the door. When we entered ... Read full Story
Sydney Sun Min 2017-12-26 18,078 Shemale Fucks Guy
100%
I Give Up
The following story is the first of four parts of a tale that explores the theme of transformation. It is thematically similar others that I have submitted but has a larger narrative arc. I hope you enjoy reading the first portion, Act One & Two. I continue to work on better editing and someone h... Read full Story
ASSEaster5678 2018-09-14 9,092 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
94%
Southern Hospitality Ch. 01
XtinaSmith2017 Ash gawped at his mother, incredulous as to what she had just said. He understood the basic premise of what had happened, but the reasoning she must have had absolutely baffled him. "Why?! Why would you do that?!" He pleaded, voice light and desperate. She shrugged, looking acr... Read full Story
Gwapo67 2022-05-16 7,093 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature
60%
I've got to make this happen
I've got a sexual fantasy that gets me aroused and makes my dick hard just thinking about it and telling it, here goes, I'm a straight male never been with a man never wanted to be with a man, I don't find myself attracted to men. I love busty curvy women,the scent of a woman the softness of a woman... Read full Story
Huckfinn642 2022-11-15 5,130 anal atm double and triple penetration double triple penetration blowjobs shemales gangbang virgin ass and mouth
100%
First Date With Daddy
My Dream Date. It hasn't happened yet, but a girl can hope, this story is very short story based on my fantasy's. It was Sunday night and I had my first date lined up with daddy. We hadn't met, but we had spoken online at depth and exchanged numbers. I had sent him a couple of pic... Read full Story
SEXYBADGIRL 2023-03-17 5,039 Crossdresser Bareback Creampie domination
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 5,271 Crossdresser Blowjob Big Cock Shemale and Girl shemale fucks female
80%
Buffy the Shemale Vampire Slayer Part 13
Buffy's cock slipped out of Baubo's mouth, and she licked the smooth skin of the stiff, elongated shaft with her tongue. Baubo had no hands, but, even so, she was a superb cock sucker. More than once, she brought the Slayer to the brink of orgasm, then backed off, letting Buffy's sexual passion abat... Read full Story
shemale lover 2011-08-23 3,756 Masturbation pussy shemale
66%
Marla Makes My Wife
I'm kneeling on the edge of the bed, my stocking-clad wife moaning in ecstasy as my shaft moves in and out of her cum-filled pussy. I watch her breasts jiggle in time with our sex. But what's really driving me mad is the feel of a hard shaft of flesh moving in and out of my ass, complimenting my mov... Read full Story
shemale lover 2011-09-18 4,985 asshole Creampie orgasm
40%
Redux
Today, Stormy Danielson was re-creating the late Renaissance's Antonio Allegri da Correggio's Jupiter and Io. Danielson's re-creation was to remain true to the original in every way but one--the same detail, if one could call such a feature a mere "detail"--that his anonymous billionaire p... Read full Story
shemale lover 2011-10-04 3,391 anal sex asshole cum deep penetration
100%
First Time Dressed… at an Electronica Concert
I had been dressing as a girl to get off for some time now. For some reason there is nothing that turns me on more than a tight little cotton thong stretched across the bud of my asshole, holding my tiny little boy toy down where it should be. Over the years I’ve slipped into my mom and sister... Read full Story
shemale lover 2011-10-21 3,377 anal first time shemales Creampie fingering
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 10,513 orgasm facial oral sex
100%
Secrets
Jon had invited me to spend another weekend at his place with another of his friends. I always find his friends to be interesting so I accepted. Jon had given me a garage door opener and a key to his home after my first visit. He met me as I parked my car in the garage. He was wearing his usual skim... Read full Story
shemale lover 2011-11-01 6,051 anal Blowjob transvestite
66%
Candy Pink Part 2
Chapter 4 My parents had a letter shortly after from the headmaster Mr. James Allen. I was to head out to CA before the start of winter term to get settled into the dorms and go through orientation. The letter said I should be there no later than December 1st and that they would arrange for me to... Read full Story
shemale lover 2011-12-08 4,432 taboo Fetish crossdressing
50%
Mommy Adriana, I Will Obey You
Finally we were on our way home. Interestingly neither Mommy Adriana nor Mistress Andrea had cuffed or gagged me. So I just sat in the back of our car. During the short drive I had some time to think about what had happened in the past two days since my wife, err Mistress Andrea, and I had picked up... Read full Story
shemale lover 2011-12-18 5,664 anal hardcore erotic encounters
100%
The Greatest Lie Part 3
My weekend escapade with my first real lover, Jake, convinced me that I was destined to live as a girl, despite having been born a boy. Unfortunately, it was my male persona to whom the University of Minnesota had extended admission and a scholarship, and I wasn’t quite sure how they would rea... Read full Story
shemale lover 2012-01-19 4,321 hardcore crossdressing erotic encounters
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 6,043 cum transsexual fantastic
100%
A New Experience
I had been sat in the hotel lobby for a couple of hours, bored, just watching people come and go. I hated these business trips. There I was in a strange city, knowing nobody, hanging around waiting for business meetings. Out of all the people I had seen there were such a variety of people. Pensioner... Read full Story
shemale lover 2012-04-01 2,563 Cumshot Creampie Big Cock
100%
A Quickie For Jemima
I checked my make-up and adjusted my brunette, bob cut, wig in the bathroom mirror. Pleased with the results I then ensured that my clothing was right. I was a vision of darkness: black G-string under black thin denier tights, 3 inch heels, black satin vest top and black mini skirt. I was sure Simon... Read full Story
shemale lover 2012-04-02 2,332 Crossdresser anal sex Cumshot oral sex
100%
Fantasies Fulfilled
I enjoy crossdressing and do so when ever I can. About the only time I dress as a man is to go to work. I have been doing this since I was eleven years old. I love to have sex with a man as if I was a woman and really think I should have been born a girl. I think like a girl and naturally act like a... Read full Story
shemale lover 2012-05-26 4,320 anal sex Creampie Blowjob crossdressing
100%
A Reluctant Gang Bang
Hi all! I have been cross dressing and playing with men for many years now. One of My first experiences was being gang fucked by about 9 guys at an adult arcade. I was 18 at the time and it kind of traumatized me as it was pretty much a gang rape at an adult arcade. I was dressed up in a white flowe... Read full Story
shemale lover 2012-05-28 8,542 anal sex Creampie Fetish gangbang crossdressing
100%
Birthday Present
Chapter 1 "What would you like for your birthday?" my wife asked. "An unforgettable sex session" I answered, jesting. "Is that right? Well, we'll see" came the reply. I forgot all about the exchange and nothing else was said about my birthday. The day arrive... Read full Story
shemale lover 2012-06-16 14,157 Cumshot Fetish orgasm oral sex
60%
A Ski Bunny is Born Chapter 3
Kim and I are thrilled that so many people are enjoying reading about our adventures. We have received so many really nice e-mails from lots of lovely people, its good to know you girls and guys out there are enjoying them! We had promised each other a trip to Europe but hadn't really made any fi... Read full Story
shemale lover 2012-06-22 8,284 Cumshot Sex Toys 69 position handjob
66%
Bitch Maker
Alex was a rather short fellow, timid, and obedient, Sammie's type exactly. Sammie lay on her back with Alex's face between her thighs, his mouth working on her balls, her legs on his shoulders. She moaned and arched her back, reaching down to wrap her fingers in Alex's hair and grind his face into ... Read full Story
shemale lover 2012-06-24 3,882 anal Creampie shemale oral fingering
100%
Fantasy Reversal Chapter 4
I looked each way as I exited the room. Thankfully, the elevator was only about four doors down and the hall was quiet. With my bag in tow I walked to the elevator pushing the button, my reflection in full view in the polished elevator door. I stood there, for a few moments as if in a trance as I... Read full Story
shemale lover 2012-06-29 2,692 anal sex Creampie crossdressing
100%
Fantastic Weekend - First Touch
It finally worked! After a year of posting ads on Craigslist, and what I'd decided was my last attempt, I got results. It was short and to the point, "Panty Sub Seeks Oral Top." As is normally the case, I got a lot of one-line responses and picture requests, but buried in there were two gu... Read full Story
shemale lover 2012-08-31 3,303 Stockings Crossdresser Cumshot Blowjob Lingerie
100%
First Night Nerves
My name is Timothy. I live in a large city in the English Midlands with my girlfriend Debbie. We are both 22 years old and have lived very happily together for over 3 years. We both work in a call centre for a large financial organisation. I am not tall – 5' 4" on a good day – and h... Read full Story
shemale lover 2012-09-22 4,052 anal orgasm fingering
85%
I Told You
“No, please…” I barely audibly whispered. “Shut up you little cum whore!” “So... ohh god, no... Fuuuuuuuck,” the words leaked through my painted lips. “You want that hole filled too, you little cocksucking bitch?” “No, please! ... Read full Story
shemale lover 2012-09-29 6,067 anal Cumshot oral domination crossdressing
100%
The Coach's Chance Encounter
Eddy McCants rolled the rack of basketballs back into the athletic storage room at Liddell County High School. After coaching the varsity boys to the final four in the state tournament last season, he had a good feeling that his team would make it at least as far this time around because he had thre... Read full Story
shemale lover 2012-10-26 3,079 anal shemales hardcore
71%
Birthday Present Part 1
Birthday Present or (I've Looked at Love from Both Sides Now) Chapter 1 "What would you like for your birthday?" my wife asked. "An unforgettable sex session" I answered, jesting. "Is that right? Well, we'll see" came the reply. I forgot all abo... Read full Story
shemale lover 2013-01-18 11,323 hardcore sucking Blowjob Lingerie ass fucking
82%
First time dressing up
I was always interested in women's clothing. I don't know what it was but it just made me wonder what it was like to be a girl. When i was 15 i finally gave into my curiosity and wanted to browse my s****rs clothes. I went into my s****rs room when the house was empty and opened up her closet. I saw... Read full Story
shemale lover 2014-07-27 6,790 anal ass sex toy Crossdresser cd