Sort by
Relevancy

Free Stories

100%
Revenge is Sweet
Henry Stewart was thirty five years old, married to a very attractive woman who'd given him three kids, he owned and ran his own very successful computing company in San Diego, "Stewart Computing", meanwhile he owned a large house in the wealthy small town of River Falls. All in all, Henry... Read full Story
shemale lover 2012-09-01 7,842 Crossdresser Cumshot Masturbation Lingerie heels
100%
Pretty Woman
Tyler was as nervous as anyone could be. Hazel eyes darted for the door as silky black stockings slid up smooth white legs to meet garter straps attached near lacy white panties. Next came the bra, straps catching on skin slightly sticky with perspiration. Heart pounding as the black pencil skirt gl... Read full Story
shemale lover 2012-12-22 8,845 Stockings Teen (18+) Crossdresser sucking heels
84%
Shool teen crossdresser first time sex
I was just a young boy then, senior in high school, horny as hell and dreaming of my first gay experience since sitting in my new red lace thong and white lacy bra and discovering the one porno in the house everyone kept hiding from me. I guess they thought my s****rs panty drawer held no interest f... Read full Story
shemale lover 2014-11-21 19,131 first time suck fingering Lingerie ass fucking cd
92%
Showing my femininity
When I was still little guy, my stepfather always told me I wasn't a real boy, but I was his little girl. One day, he was drinking beer with his friends, so he grabbed me by the arm, pulled my shorts down and showed off my teeny cock to them. I remember that all of them laughed at me. They made fun ... Read full Story
Shemale Dill 2020-04-27 8,075 Crossdresser Amateur Group Sex Blowjob Big Cock gangbang Lingerie
100%
sissygurl
Sissygurl development A true sissy always wants to always look as sexy and desirable as possible and with a body that looks fabulous in your sexy sissy outfits so you will be super motivated to stay sleek and slim. Now let’s talk make-up. Besides the essential stuff to have in your make-up kit... Read full Story
amberdoll 2023-02-16 6,240 Small Tits Crossdresser Amateur Homemade
50%
a diary piece - my next date
A diary piece - my next date I hadn't forgotten how to please a man and I had decided to be a little whore for him. Yes I enjoyed it very much and wanted to be fucked again the next day. When I start having sex I want it all the time. HiltonP had said he wanted a date again on 21st and 28th ... Read full Story
amberdoll 2020-09-16 2,750 Stockings Small Tits Crossdresser Amateur Bareback blonde Lingerie Homemade
100%
A Different Kind Of Lust
This woman he is with is not really a woman, but he still feels the urge to give her the best sex ever. She is pretty, long blond flowing hair, long sexy legs that she can wrap her legs around him. Her hands are soft and gentle, like a woman's hands should be. Her body is slender and petite. Her ass... Read full Story
shemale lover 2011-09-11 2,304 anal sex licking cum
85%
Crossdresser At XXX Movie
It was hot and the sun felt like it was going to melt me. I was walking home from work. I never drive that much and I just got off the bus for a fast beer. I walked past this XXX Movie house and thought what the fuck, it has air and it is so hot. So in I go. I should say that I'm somewhat Bi. Tha... Read full Story
shemale lover 2012-03-30 4,099 anal sex Creampie handjob rimjob
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 3,287 tranny Crossdresser Masturbation
100%
Sabbatical or Continuous Gang Bang?
My twin sister Laura had already left to go back to college this fall season, but I had decided to take off a semester as I was totally burnt out on school and needed a break. We were twins but not identical though we did look a lot alike and roughly the same size me being a few inches taller. My... Read full Story
shemale lover 2012-08-28 5,631 Crossdresser Cumshot Fetish Blowjob gangbang
100%
Sabbatical or Continuous Gang Bang? Chapter 2
I awoke several hours later still laying on top of Rick his arms holding me tight to him. His cock had gone flaccid as we slept and slipped out of me. I felt like I had run a marathon and my ass pussy felt like it had a marathon run through it. I slipped out of Ricks arms onto the bed and went into ... Read full Story
shemale lover 2012-08-28 3,877 anal Crossdresser Fetish Interracial
93%
I Am My Wife's Best Girlfriend
I was standing in our bedroom, my wife was on her way out the door. I was holding her slip up against my naked body. It felt very sensual. I pictured myself, for just a moment, as a real woman, with large breasts, big blonde hair, and smooth, hairless skin. I rubbed the fabric against me, sighing. S... Read full Story
shemale lover 2013-01-18 7,288 Crossdresser Cumshot Creampie Blowjob ass fucking
96%
My First Time as a Girl
I was hoping to hook up with a straight guy. I have 2 b*****rs and a s****r I’m the youngest and a Freshman in high school. Always been fem preferred to play with my s****r and her dolls. My dad is an ex-marine. Tough guy. My b*****rs are following in dad’s footsteps, military orientated. I‘m a b... Read full Story
shemale lover 2013-12-07 6,681 tranny Crossdresser Creampie ass fucking cd
100%
Daddys Little Slut
I have been living with my dad for the last year after my mum who is Indian, found out that I was doing lots of drugs, and that I was bi and also a cross dresser. We never talked about it as for me, the cross dressing was on and off and usually when i was high. When i turned 25, I tried meth, and fo... Read full Story
aishacox 2023-01-31 5,477 Crossdresser Cumshot Fetish Blowjob Latex
69%
Kits Adventures in the North
**Crossdress Story** It had been about six months since I'd had any chance to dress, any chance to feel sexy and been even longer since I had any kind of sexual contact. Work tends to do that; gets in the way and screws about with "me" time. Luckily, though, it was only a temporary job... Read full Story
shemale lover 2015-08-31 5,635
50%
Clinton
"How many inches?" she asked. "Twelve," he said. "Really?" "Really." "If you're lying, you're just wasting your time." And mine, she thought. "I'm not." "Okay, then. It's a date." Tiffany hoped the jerk was te... Read full Story
shemale lover 2011-09-19 10,769 Big Cock cunt anus
77%
Caramel And Devin
I began crossdressing at 12, but it wasn’t until I was 17 when I dressed up completely for the first time. When my parents went away for the weekend to Atlantic City, I took advantage of the opportunity to explore my feminine side to the fullest. As soon as they left the house that summer morn... Read full Story
shemale lover 2011-11-10 4,367 Cumshot sucking fingering
60%
Booty and the Blue Pill
This is my account of the first time I took a Viagra. At 40 years old I have thankfully never had to go that route but you know curiosity killed the cat. Or in this case opened up my ass! After telling the guys at work how I planned on staying in while my wife was out of town visiting her sister,... Read full Story
shemale lover 2012-04-15 4,326 Cumshot sucking jerking gangbang Interracial
50%
My Clipped Cock
Technically, right now I am an "It." A few weeks ago I was a "He." In another few weeks I will be a "She." The adventure is a celebration for me. I am doing everything right, and sensually documenting and sharing the adventure with my very-supportive and very-erotic fri... Read full Story
shemale lover 2012-04-27 4,714 transformation crossdressing
100%
Abducted and Turned Out Chapter 2
2: Fun time So, after I blew the guy downstairs and told him to come and knock on my door and pay me to blow him again anytime, I went up and took a long hot shower and put on a nighty and went to sleep. I slept surprisingly well considering I had just spent a long night out selling my ass. I tho... Read full Story
shemale lover 2012-08-10 4,650 Crossdresser anal sex sucking Creampie facefucking
100%
Working for a Living Chapter 6
I slid out of the old Ford truck driver's side door. Surprisingly, my legs felt a bit shaky as my feet hit the concrete driveway of the Malibu mansion. I nervously straightened my cut-off shorts as I walked around the truck. She was waiting by the tailgate with a big smile on her face. "Wow Jai... Read full Story
shemale lover 2012-10-05 3,682 Group Sex Creampie threesome
50%
Wife Converts Husband Chapter 2
We end up going to a big lingerie shop and buy several pairs of g-strings, booty shorts, bra's, corsets, suspender belts and stockings of all colours and styles, which Shelley thought would best suit me and a pair of breast forms to give me real looking breasts. We then went to a shoe shop and bough... Read full Story
shemale lover 2012-10-18 3,934 cum fingering oral sex Sex Toys
81%
Forced Entry
Danny sat at the bar of the Holiday Inn nursing his fourth double scotch, espousing to the man beside him the reasons why his company was the best designer and distributor of accounting software in the world. Danny was a large man in his forties and was running to fat. He was dressed in a travel-... Read full Story
shemale lover 2012-11-16 15,870 Big Cock oral transvestite forced sex
100%
One experience with two black men
Hello again this is EvA…I am a 40 year old tranny. I do not consider myself a cross dresser anymore, because I am doing that for so long that I have been transformed to a very sexy and feminine lady boy. I have been taking also hormones for 4 years, on and off and I already saw many changes&h... Read full Story
shemale lover 2013-05-16 4,526 Stockings anal sex suck threesome Interracial cum swallowing
86%
James's Cum Slut
I had decided to spend the first week of my summer holidays after my AS levels at my friends house down in Hampshire. Both being borders at school we caught the train down to his house after term had finished. The house was a nice county retreat with a medium sized pool and a tennis court set in the... Read full Story
ATC97 2015-04-15 5,413 Crossdresser Blowjob oral bikini riding cd
94%
The Girl Next Door Ch. 01
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. H... Read full Story
Gwapo67 2022-05-13 6,881 Bareback Creampie Big Cock shemale + shemale
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 6,354 Crossdresser Interracial sissy chastity Cuckold Husband
100%
In the shadows of the city park
It is gonna be just one of those nights again. A night where the depraved girl in me won't stay quiet, demanding control and attention. I could feel it during the day already and now that the sun is about to set and the streets are slowly but surely emptying as I find myself in my appartment getti... Read full Story
Anna_Lima 2024-01-13 4,407 crossdressing blowjobs
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 4,231 sucking domination ts foreplay
100%
Barbie Jo Adventures Part 6
Saturday When I woke up, I was alone in Harley's bed. I went to the bathroom for the usual thing when you first wake up in the morning. I looked at myself in the mirror and saw me, a guy. I felt embarrassed being in Harley's house with no makeup on. I had a quick shower, borrowed Harley's razor t... Read full Story
shemale lover 2012-02-18 4,434 cum oral face fucking
25%
Adult Bookstore Dancer
Adult Bookstore Fun At one time there were eight adult books in my city now there is only one. Makes me very sad as I loved dressing up like a twenty-five cent whore and visiting them on the weekends. I think I enjoy all the humiliating comments and condescending looks the customers would make abou... Read full Story
shemale lover 2012-02-26 4,255 sucking Fetish cross dressing
100%
Becoming a Free Spirit
She lay dying in my arms. A brief smile came across her face. She croaked "honey remember that idol I told you about locked away in the safety deposit box?" "Yes dear but save your strength okay, I'm not concerned about some idol" "But I have to tell you about it. I... Read full Story
shemale lover 2012-03-02 3,058 sucking Fetish cum fucking Sex Toys fantasy
100%
Daddies New Girlfriend
Doug suspected his 19 year-old son Jerry was stealing money. Doug worked far too much trying to provide for his son to supervise him properly but drew the line at theft. So he decided to set up a web-cam behind the mirror in his bedroom, he'd used the very same 2 way mirror to film his dead wife Cyn... Read full Story
shemale lover 2012-03-09 12,319 sucking Fetish crossdressing
88%
A Schoolgirl Story
Jason Sheen was eighteen when he moved to River Falls with his mother. Ever since he was a small child Jason had lived with just his mother, Felicity, and he could no longer remember anything about the father who had abandoned the two of them when Jason was just three years old. Fortunately, Felicit... Read full Story
shemale lover 2012-06-05 15,056 cum oral jerking off crossdressing
100%
Demoted Chapter 1
Monday I had been working in this office for a couple years, I was a floor supervisor had my own office and a few people under me. It was very easy and never had any trouble at all. I am also a cross dresser and I didn't know it but my story starts with a page I had on the Internet. I checked my ... Read full Story
shemale lover 2012-08-13 5,555 Crossdresser Fetish Lingerie
50%
Al Fresco: An Erotic Sci Fi Tale
"Thank goodness for modern science," Ali said as she smoothed her tight black skirt across her shapely hips. The tall brunette turned this way and that in front of her mirror, admiring her taut, toned, and trim figure. Her hands moved up from her hips to cup the twin handfuls at her chest,... Read full Story
shemale lover 2012-09-19 7,239 Cumshot ass fucking oral sex cum swallowing
100%
Caught Cheating
Hailey lifted her head, which had been resting on her arm up for the second time that hour. Down at the front of the lecture hall, her chemistry teacher was droning on about the wonders of balancing chemical equations. Sitting up in her chair, Hailey stretched out her arms and yawned softly. As she ... Read full Story
shemale lover 2012-10-07 5,037 cum oral sex deepthroating
75%
Fucking Insatiable
* Draenei futanari, as many of us have become intimately aware, are fucking insatiable. For many of the same reasons, they also have a tendency towards entitlement and ego issues. This is hardly surprising, being a magically-fueled blue-skinned space-babe with positively porn-star T&A and a d... Read full Story
shemale lover 2012-12-07 5,796 sucking gangbang Futanari
100%
Young Sissy Chapter 1
I don't know how long I was under...days, weeks...who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck with needles, filling me with horribly persuasive dreams of a beautiful new body. I tried to imagine myself as a man, just to s... Read full Story
shemale lover 2013-01-04 10,310 sucking Fetish Uniform domination big boobs
92%
A Sissys new start
I only ever told my father one lie. That was about the boots. I was about to turn 18, jobless, directionless and pretty screwed up to be honest. There had been rows, fights, shouting matches and long frustated silences about what i was doing with my life, but i had formulated a plan. Kind of. Tw... Read full Story
SissyDani31 2018-10-04 5,552 Teen (18+) Crossdresser Amateur
85%
BANGING AROUND BANGKOK
BANGING AROUND BANGKOK: THE AMOROUS ADVENTURES OF CAITLIN "MEOW" MORRISON after living and working in Thailand/SE Asia for many years i decided to write an erotic story based on some of the people i have known, venues and places i have been, and the P4P night-scene where i spent way too much... Read full Story
bkkldby 2019-06-17 14,264 first time Teen (18+) Amateur Group Sex Big Tits Cumshot Outdoor Bareback Blowjob Big Cock Asian lesbian public place
100%
Meeting Amanda
I’m a happily married man. My wife Tess and I have been together since we were teenagers. We were each other’s first real lovers and being in our mid-thirties by now, we still madly in love with each other. Tess and I always are very honest and open to each other. Both in normal life and sexual... Read full Story
rforasht 2022-07-20 7,605 Big Tits Cumshot Shemale Fucks Guy threesome blonde Big Cock Lingerie Shemale and Girl redhead Homemade Shemale fucks couple
100%
An unexpected kiss under the rain
Army Bear left that morning leaving me horny as hell. I couldn't go back to bed without playing with myself for a while. I opened my Pandora box and I took out my 9 inches, big dildo. I played with it for a few long minutes, burying it all deep in me thinking of him. Doing a few hits of poppers, I f... Read full Story
HotVersatileTs 2011-10-05 4,803 sucking domination foreplay cd
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 7,987 asshole licking sucking
90%
Date With A Mistress
It was a sultry afternoon and I was sitting in my study remembering the events of the past weekend. Never before had I thought that I would endever to fulfill my fantasies until I met Angela. Friday Night: It was late in the afternoon when I decided to check the adds on my computer. I was look... Read full Story
shemale lover 2011-11-04 6,658 taboo Crossdresser hardcore
100%
How I Became a Tranny Whore
When I was 30 with children at home I would get dressed in the bedroom. When it was time to leave the wife would take the children off for ice cream and as soon as they were out of the drive way I would head for my car. Of course when I returned home the children would be a sleep. The plan worked fo... Read full Story
shemale lover 2011-11-07 4,710 anal Cumshot cum swallowing
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 8,925 cum oral domination
30%
CD Delight
The following is an account of a true encounter between consenting adults. The names and places have been altered to protect the individuals. Any resemblance to actual persons is purely coincidental. It is not intended for minors. If you are offended by sexually explicit material or have receive... Read full Story
shemale lover 2012-01-27 3,385 sucking cum Sex Toys cd
100%
Whatever dreams may cum
I just have to share with you an experience that I hope someday becomes real. It was cool Saturday night in August and I was out at the club with some friends. I was wearing a black and blue stripped dressed that went down to my thighs. It wasn't quite a mini, but you could see my sexy black thong u... Read full Story
shemale lover 2012-02-01 3,030 first time shemales hardcore
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 3,378 Stockings sucking cum facial
85%
A Glory Hole for Tranny G
I am reveling in what a difference almost a year has made. I remember meeting Chris online, exchanging a few funny e-mails, two days after my birthday. No more and no less, just a person somewhere who I had no idea what he was like or looked like, but someone who made me laugh with our e-mails each ... Read full Story
shemale lover 2012-03-07 3,499 Group Sex licking sucking cum gagging
0%
P.A. for a Day
The gates swung closed behind Charles as he slowly drove his car up the sweeping driveway. Even though he was looking forward to the erotic delights which were in store for him that day, the cares of the world seemed to weigh heavily on his shoulders. As he drove up to the garage he mused about t... Read full Story
shemale lover 2012-09-05 6,013 Crossdresser Masturbation Latex Sex Toys heels
76%
My Wife's Secret Fantasy Chapter 1
PART ONE: REALIZATION The old saying "you never really ever know some one" is quite true when it comes to my wife Debbie. Debbie has always seemed to come up with new surprises to keep our marriage stimulated and adventuresome. As I've recently found out though she seems to have been ke... Read full Story
shemale lover 2012-09-09 9,977 Crossdresser Cumshot Masturbation Lingerie heels
100%
Force of passion
::The Ebon Hawk hurtled along silently through hyperspace. The Jedi Exile, Shi'la Raan, watched the white stretching stars as they headed towards Korriban. She felt uncomfortable heading to a planet that was a graveyard for Sith. It was like a darkness in the back of her mind; a whisper in the force... Read full Story
shemale lover 2012-09-18 3,297 cum oral kissing
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 7,302 Fetish cock sucking crossdressing
85%
Becoming a Shemale's Bitch
I just got into town and spent the whole day moving in and cleaning my new apartment. I didn't have much furniture but the place needed a lot of cleaning. I saw their was a bar a few blocks away from my apartment and decided to go out for something to eat. It was around five o'clock when I walk... Read full Story
metamafia 2012-12-21 119,144 hardcore Cumshot sucking bdsm domination