Sort by
Relevancy

Free Stories

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 3,881 sucking Fetish Ladyboy rimjob
100%
An Invitation
"Oh come on,Sarah. There has to be a way." An innocuous enough statement, but that's how it all started. I'd just received an invite to Cressida's annual Christmas party which, maybe not on the Hollywood A list, was within the cognoscenti an occasion not to be missed. The soirees of ... Read full Story
shemale lover 2012-11-16 4,606 Fetish oral sissy
100%
Lady In The House Ch. 08
A story by MicheleNylons (Crossdresser must comply with jailhouse heavy.) "You!!!" Eddie screamed through the bars, then laughed. "Well done girls, quite a show, I really enjoyed that; and so did Michele obviously," he said snickering and pointing at the tent in the front of my skirt caused by... Read full Story
✘Transensual✘ 2019-02-25 5,746 Crossdresser domination PRISON PUNK prison sex Prison Bitch
95%
First time
Hi, my name is Sandra. In fact, I'm not exactly a girl, but a CD. Even as a child, I felt different and I used every opportunity when I was left alone in the apartment to dress up, to put on women's clothes, to put on make-up. In time, I started watching porn, as did all my friends. But, unlike them... Read full Story
cd Sandra 2021-10-13 5,702 Stockings Teen (18+) Small Tits Crossdresser blonde Guy Fucks Shemale
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 4,336 Crossdresser Blowjob blonde Big Cock domination Mature cum in mouth
100%
First Time I Experienced Eating a Tgirl Out
So this is likely going to seem tabboo for some and if this is not your thing, I respect that but everyone is different. Eating pussy came natural to me like it does for most guys once they start having sex with girls. Other than one time 69ing with a female and having what I would call "incidental ... Read full Story
AllenB 2022-10-21 5,126 Amateur Big Tits Cumshot Latina Creampie Fetish Blowjob rimming Homemade cum in mouth latina ts
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 7,906 asshole licking sucking
50%
Old Folks
I had been cross-dressing for some years, but I had never been with another man. I had been talking on a gay chat site for some months when I found someone who I got on with well. We exchanged photos I was happy with his and he was happy with mine. Deciding to get together, we arranged a date and ti... Read full Story
shemale lover 2012-01-10 7,981 transsexuals romance crossdressers
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 6,871 transsexuals erotica romance crossdressers
66%
Chinese Extremes Part 4
The ride to Master's residence was completely uneventful for Lien. The whole way she lay in the trunk of his limousine, hooded and gagged, with her legs strapped together and her arms secured with the armbinder. The trip may have been uneventful, but Lien wasn't bored. She spent the whole trip fanta... Read full Story
shemale lover 2012-01-17 4,596 torture extreme bondage and discipline
72%
First Time Sissy Maid
I had been fantasizing for many years about serving a dominant Mistress, watching lots of movies online, and generally lusting over the doms I saw posting ads. At the age of 28 I finally found the courage to answer a rather intriguing post by an older woman and her trans partner who were looking for... Read full Story
shemale lover 2012-10-27 16,921 first time Fetish Big Cock domination sissy
100%
Fixing The Car
I had been cross dressing since I was about 10 years old, I'm now in my thirties and this story is about my first encounter with another man. It all started one day when my wife would be out for the day and I had settled down to surf the net looking for transgender sites, I was only dressed in a bla... Read full Story
shemale lover 2012-11-08 4,046 first time Fetish crossdressing sucking off
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 10,228 Big Cock cumming sperm ebony cock
100%
The Next Level
Nitromethane It's been a couple of weeks now since I sucked my last shemale cock and swallowed her load, and with enough distractions, it hasn't been too difficult keeping myself preoccupied and my mind off of satiating my new fixation. Still though, I do have my moments when I sit back and imagi... Read full Story
Gwapo67 2022-02-01 5,769 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock gangbang domination cum in mouth
100%
Whoops, I fucked my bosses son! Real story, written by a tgirl
Normally I never would have entertained the idea of sleeping with a co-worker but when I saw my boss’s son for the first time, that idea quickly went out the window. It wasn't like I didn't think about fucking my co-workers, I did… in fact, I would leave work some days leaking with precum from the v... Read full Story
Madison Heights 2022-10-27 6,885 Bareback Blowjob shemale Big Cock Uniform Lingerie tgirl office sex cum in mouth coworker creampied workplace
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 5,333 Crossdresser Cumshot Fetish Blowjob Latex
33%
Duel With the Devil, Chapter 20 of The Greatest Liar
Duel With The Devil This is a work of fiction. All characters (including the narrator), celebrities, places, residences, neighborhoods, restaurants, legal agreements and proceedings, events and incidents are either the products of the author's imagination or used in a fictitious manner. Any r... Read full Story
the greatest liar 2023-07-19 4,115 anal Bareback Creampie Ebony Guy Fucks Shemale post-op celebrity post op sex
33%
Being Barbi's Bitch
After ten wasted years of foolishly trusting in love to 'cure' me of my femininity, I had only just begun to re-embrace the sissy inside me when something made me reach out to an old friend. What made me do it, I really don't know. Although I was once again revelling in even the smallest aspects of ... Read full Story
shemale lover 2011-10-01 8,997 Stockings sucking domination
100%
Headmistress' Favorite Sport Part 10
When Denise came to she was lying in bed. She had been washed and she could no longer feel the annoying diaper rash. In fact she felt fine, clean and well rested. On her feet were what turned out to be black Oxfords with seven-inch heels. Her ankles were in steel cuffs and connected by a eight-inch ... Read full Story
shemale lover 2011-12-13 4,665 torture toys bondage and discipline chastity belt
100%
Permanent Stay in Mastersville Part 1
I had just turned eighteen, finished high school and was ready to take on the world. My parents were long dead and I hated my foster family and they hated me, so when I turned eighteen and finished high school our ways parted. I left the small town I had grown up in never to return. I had no real fr... Read full Story
shemale lover 2012-01-07 4,706 toys bondage and discipline heavy reluctant
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 14,934 cum oral jerking off crossdressing
100%
Denial: Third Comes Conversion
It had been a few weeks since Mark had became Miranda full time. He no longer had any of his own clothing and had taken a place as servant in the home. Janine had been slowly beginning to work Mark over by using 'creative discipline' and during the last day few weeks had began altering his behavior ... Read full Story
shemale lover 2012-08-16 3,618 jerking oral sex sissy
76%
Open Wide
"Turn your head slightly to the right," she told me. I turned and my face bumped up against her left breast. "Oops, don't you bite that now," she said. "I wouldn't do that," I replied. "You better not 'cause you'd make a hole and I'd fly backward ar... Read full Story
shemale lover 2012-09-01 10,375 Cumshot Blowjob Big Cock Uniform cum swallowing
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 5,939 tranny Stockings suck Creampie ass fucking doggy style Latex
80%
Are my Tranny Orgasms Unique?
There have been some changes, some dramatic changes, in my sex life since before when I started out acting the heterosexual male role. Rather than being the hard cocked male entering whatever female partner it happened to be this time, now I am more commonly the trans partner being entered. Previous... Read full Story
⭐TransGurl⭐ 2017-02-17 11,913 tranny shemale trans ts gusher g-spot
100%
Police House Call
My heart was beating a mile a minute when I heard the knock on my door. I was hoping that it might be Beau, or Larry, or if I’m lucky it would be Tom Cobb. He asked me to call him Tommy. I had been thinking about him recently. Bo and I had banged the night before, but I was as horny as ever. Larry w... Read full Story
Regina10 2024-04-19 3,518 Crossdresser Big Tits Bareback Blowjob Big Cock Ebony Guy Fucks Shemale big ass femboy cum in mouth
87%
Headmistress' Favorite Sport Part 3
There was no more time for Denise and Susanna to get over their chemically induced bout of incestuous activity as Denise was being sent to school. This was of course part of the plan. Slaves should always feel guilty about something and once their slave training was over, neither would be able to ma... Read full Story
shemale lover 2011-12-12 6,261 toys bondage and discipline chastity belt
36%
A First Time for Hannah
At age 24 and after years of dressing in private, I finally decided I needed to get out. I had been scouring online personals for some time but never got further than exchanging a few emails and trading pics. I had been in touch with other CDs from all over the country and had even considered travel... Read full Story
shemale lover 2012-03-01 2,827 first time Fetish crossdressing
100%
A Job in the Theatre Chapter 16
"Ted has invited me to his poker game" Paula let slip. "Oh really? Now that sounds interesting" Sarah said. "It will be if we come up with the right uniform. It's all boys so I am going to dress in some sort of domestic help type uniform. But of course it has to be the... Read full Story
shemale lover 2012-03-15 3,233 shemales anal sex Big Cock
100%
The Shop
I lunged backwards to get more of him in me. I heard him grunt as half of him slipped passed my tight sphincter muscle. The pain was in the back of my mind, somewhere but this unbelievable feeling of lust had taken over me. I looked over my shoulder (what a sight that must of been, a 18 year old ... Read full Story
shemale lover 2012-04-12 3,751 anal sex Fetish crossdressing facefucking rimjob
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 10,657 Stockings anal sex Fetish Interracial sissy
90%
On the Run
“Your first mistake was stealing hundreds of thousands of dollars from me. Your second mistake was thinking you could get away with it.” As I stood trembling before his desk, Mr. Atwater regarded me as if I were a bug on the windshield of his Lexus. “Do you have anything to say for... Read full Story
shemale lover 2012-09-01 11,303 Crossdresser Cumshot Blowjob jerking pantyhose
100%
Lady In The House Ch. 05
A story by MicheleNylons (Crossdressed prisoner is forced into prostitution.) From Part IV Then Eddie looked down at my body and noticed the semen pooled at the front of my panties. My semen! He looked down at his tight belly and saw a slimy stain that was the result of my ejaculate spread th... Read full Story
✘Transensual✘ 2019-02-25 4,525 Crossdresser domination PRISON prison sex
100%
Lady In The House Ch. 06
A story by MicheleNylons (Michele continues to be used by prison inmates.) From Part V Harry leant over me and kissed me full on the lips. "That was worth every penny; you are one hot nurse," he laughed. Harry grabbed a handful of my clean white skirt and wiped his cock on it. The silver... Read full Story
✘Transensual✘ 2019-02-25 3,749 Crossdresser domination prisoner prison sex Prison Bitch
50%
Hard Decisions by Elaine © 2020
Hard Decisions by Elaine © 2020 No one in this story is based on anyone alive or dead. It is a work of fiction and should not be read by minors. I appreciate the kind efforts of many of my friends who cast a welcoming glance over the initial writings. I owe you all a big debt of thanks. Prolog... Read full Story
Elainetguk 2023-09-06 4,818 Stockings Big Tits Creampie Lingerie Guy Fucks Shemale Mature
100%
Lola Chapter 2
Lola Chapter 2: A couple? It wasn't as if we were together. We had jerked off together once, and of course we slept in separate rooms, but I slept restlessly that night. Dreamed something scary that I couldn't remember in the morning. I didn't have work scheduled that day so I took it easy. When ... Read full Story
BellaBeau 2023-10-05 5,413 anal Cumshot Creampie Guy Fucks Shemale Homemade latina Tgirl
100%
Lola Chaper 3
Lola chapter 3 When Lola was on summer break from her law studies, I took the opportunity to take some time off as well. My job as a freelance film photographer gave me good opportunities to manage my time. I was in demand as a filmmaker and had more work than I could handle. Mostly shorter stuff... Read full Story
BellaBeau 2023-10-29 5,294 anal Cumshot Latina Masturbation Bareback Lola
75%
Aunt Susie's Training Part 5
Aunt Susie and I woke up around 1030AM and Aunt Susie said we need to get ready for a surprise appointment in the city. We put on our make up, I pulled a ponytail again and we got dressed in jeans and heels and matching white button down shirts which we left untucked. We drove first to Aunt Susi... Read full Story
BITCHGURLvr 2024-05-16 2,974 cock sissy Cigarettes
100%
My first sexual encounter as a sissy
My sexual sissy encounters Part 1. The first time I met a man was some years ago now. We met online, the usual way. It was my first ever cock as i started my sissy lifestyle. He was a tall black man that was studying psychology at the time. So my first cock was indeed a BBC hehe. I wore a scho... Read full Story
Sissy Kenzie Star 2024-07-08 973 anal Crossdresser Guy Fucks Shemale sissy
100%
The Greatest Lie Part 12
My Own Worst Enemy Let’s face facts. The so-called the "War On Drugs," "Just Say No," and all the other anti-drug campaigns are complete failures because they ignore reality: getting high is fun. College students drink and take drugs to break a boring routine; the poo... Read full Story
shemale lover 2012-01-20 4,285 hardcore crossdressing fantastic bondage and discipline
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 4,516 erotic encounters fantastic consensual
100%
End of the Beginning
Jamie stood there with her mouth hung open for a moment. She was utterly shocked. How could it be true? Chloe and Josh met at basic, how could they be engaged? It had only been a month since Jamie left. Tears stood in her eyes but refused to fall. This was not at all what she had envisioned. “... Read full Story
shemale lover 2012-04-14 2,548 anal Creampie oral
100%
Darla's Diary: Slutfest 1993
Vacation Day One At last!! Another fantastic two weeks of freedom...the freedom to do as I pleased and dress as I pleased because it was my VACATION TIME!!! This year was better than other years because it was the first time my wife and I had two weeks vacation each. Just like she does every othe... Read full Story
shemale lover 2012-07-14 3,870 oral facial cum swallowing anus
90%
Young Crossdress, Meets His Daddy
Well I am 28 year old male, not in best of shape. I can still run a mile in under 15 minutes, and I work 3 to 4 times a week. I try to stay in shape a little bit. Well that is enough about my physical appearance. I am also married to very beautiful wife, who I love more then the world. We have very ... Read full Story
shemale lover 2012-08-17 4,542 anal Crossdresser Cumshot Fetish oral domination
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 4,219 Fetish oral sex cum swallowing jacking
100%
Amy's Surprise
We had been going to a local restaurant several times a week for a few months. It seemed that almost every time we had the same waitress. We soon found out that her name was Amy. She was thirty something, very pretty, even sexy all while wearing her uniform and very little makeup. She had fairly sho... Read full Story
shemale lover 2012-11-01 4,761 Blowjob cum oral sex
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 6,843 anal sex Shemale Fucks Guy Blowjob mexicana cum in ass first time with a tranny
100%
Finding out my next-door neighbor was a crossdressing beauty que
Finding out my next-door neighbor was a crossdressing beauty queen. I mean fetish is trans women, but I don’t mind blowing a load to a beautiful cross-dresser. I used to live in a small apartment complex in Queens New York. My neighbor was a guy name Luiz from Brazil. A very friendly and fl... Read full Story
My Shemale Attraction 2023-02-12 6,200 Crossdresser Amateur Fetish cum in mouth
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 5,286 Crossdresser Blowjob Big Cock Shemale and Girl shemale fucks female
100%
My First Time Out Part 5
Preface: It is not imperative, but helpful that one reads Parts 1-4 in order to grasp the personalities of characters in this story. WARNING: The following story contains some explicit foul language and IS NOT for reading pleasure of anyone under the age of 18; nor is it permissible to read if yo... Read full Story
shemale lover 2011-10-18 4,272 fingering tgirl handjob
33%
Growing up CD
Peter, Max and I played together like that for the rest of the weekend. We must have sucked each other's cocks at least 10 times over the three days. Peter and I were both physically drained. Max just seemed to be insatiable for our bodies. He didn't want us to go. He kept on saying how much he ... Read full Story
shemale lover 2011-12-04 4,201 sucking Fetish
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 5,255 Fetish trans tv
75%
Debbie Part 1
He had gotten a job with a large company doing odd jobs, mostly filing papers and bringing out mail. It wasn't much, but it was enough to pay for a small one-room apartment on the seedier side of town. Since he was still very shy from his experiences in high school he hadn't made any friends yet, bu... Read full Story
shemale lover 2011-12-22 9,345 transgender toys bondage and discipline heavy
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 6,051 cum transsexual fantastic
83%
A Man's Place
I couldn’t believe my luck, a raise! Finally, after working three years in this stinking company as Marketing Manager, and I finally get a raise. Okay, granted, it took for the company to be bought out, have a number of people sacked, and to squirm like mad to do it, but I got there! 5000 quid... Read full Story
shemale lover 2012-03-18 3,386 Stockings Fetish cum oral feminization
100%
Chaz
I met Chaz online. It was to be the first time I met and dressed for a guy without my wife’s knowledge. She had stopped being into dressing me or letting me dress around her. She felt we needed to get back to “normal” play. Chaz told me he wanted me to come over in the afternoon... Read full Story
shemale lover 2012-03-21 3,323 anal sex Fetish gay