Sort by
Relevancy

Free Stories

100%
My First Experience
Preface: A few years ago I was surfing craigslist (back when that WAS a thing) and found a couple looking for a man. I responded to that post and went back and forth until we set up a time to play. I arrived on the night and had a few drinks, We chatted and I noticed that the husband kept touchi... Read full Story
rileystar 2020-04-01 19,183 Crossdresser Amateur Group Sex threesome Lingerie domination
85%
Becoming My Roomate's Wife
Him becoming my master started a year ago when we moved in as roommates – we are both in our mid 20's and had relationships break up at the same time (we were sharing apartments with our girl friends at the time). We have known each other for more than a decade and have no secrets from each ot... Read full Story
shemale lover 2012-04-01 8,755 Crossdresser anal sex domination oral sex
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 14,120 first time Teen (18+) Amateur Group Sex Big Tits Cumshot Outdoor Bareback Blowjob Big Cock Asian lesbian public place
100%
Our special trip
John and I were having a nice relaxing afternoon cuddled up on the couch watching TV. Our relationship was shifting from all about great sex to enjoying the time we spent together just being ourselves, with me dressed up of course, and the sex seemed to me to be more loving. I'd still seduced him at... Read full Story
shemale lover 2012-02-22 3,058 Fetish cum fuck wig dressing
100%
Ana in Action
I had fantasized about him for months. I just wanted to know what it was luck to have him pulsing inside me, to feel his body pressed against mine in sheer lust. I just had no idea that it would actually come about and that my wife would be the hook up. You see, Jim has been one of my wife's drinkin... Read full Story
shemale lover 2012-11-23 3,017 threesome cum fuck oral
100%
bi to sissy caught and turned
It was during a Wednesday nite supper this past April when Penny my wife of seven years, suddenly looked me straight in the eyes while calling me a GAY COCKSUCKER ! Instantly while I swallowed hard and quickly looked away from her, my worse dreaded fears in life had somehow just become reality! So ... Read full Story
redthongthong 2022-08-02 8,910 Crossdresser bisexual sissy crossdresser forced feminization CAUGHT!
100%
Birthday Breaking
I had no idea what my girlfriend had planned for me that day - and if I did, I'd probably still have gone along with it. My birthday wasn't that special an occasion for me. I had no family and having recently moved, I'd no real friends in the city. But Gen was determined to give me a time to reme... Read full Story
shemale lover 2012-06-13 4,461 threesome oral sex strapon
100%
The New Nii
The bedroom door opened and the two lovers walked down the hall into the living room side by side. Deena was wearing her nightshirt that she wore a lot, and Jeffery was nude, and he picked up his clothes that I had put on the chair and began to get dressed. “Jeffery is going to go and get dinner an... Read full Story
Setinkhan 2021-05-28 5,574 Crossdresser Fetish threesome Big Cock Shemale and Girl domination Interracial Sex Toys
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 11,304 Crossdresser Cumshot Blowjob jerking pantyhose
84%
Abi's Virginity taken by Intruders
Abi got very little time to be herself, A closet TV, sharing a small two bedroom flat with a male friend, it was only once every few months or so she got the flat to herself and could dress up sexy and be her proper girly self, and tonight was one of those nights! Although she had no plans to mee... Read full Story
AbiTV 2015-03-18 6,415 Crossdresser threesome sex fantasy virgin
83%
Becoming Missy
It all started back in 1973 in Seattle, Washington. I was 21, living on the south side with a couple of buddies while we were all stationed at area military bases. One Friday night we had a party at our apt. I was standing outside by my car smoking a joint when this guy pulls up in his pick-up. &quo... Read full Story
shemale lover 2012-03-31 3,754 Fetish cum oral sex crossdressing rimjob
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 9,887 Crossdresser Cumshot Masturbation Lingerie heels
96%
CD Jinn Caught
Lately I have been having great times with one of my roommates who found me out and found he really enjoyed being with me when I am dressed. However before any of this happened I had met a guy through a friend on the football team at my college and had a couple great times with him while I was dres... Read full Story
Jinn.V23 2014-05-07 5,496 sex toy Crossdresser Cumshot suck threesome
89%
The Magic of my first Blac Coc
Wow! This was my first real experience with Black Cock. it was right after my divorce. I was in my late twenties. I ran my ads as a crossdresser on a few dating sites and on Craigslist. I received a message on my AFF site from a member whose profile name was BBCRicky. My interest was immediately... Read full Story
Tvtrinity 2021-04-07 21,680 Stockings Amateur Bareback Lingerie Interracial transgender sissy bbc сrossdresser tvtrinity
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 7,959 Crossdresser Amateur Group Sex Blowjob Big Cock gangbang Lingerie
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 2,657 Stockings Small Tits Crossdresser Amateur Bareback blonde Lingerie Homemade
100%
Shemale Porn
Nowadays, I masturbate exclusively to shemale porn. Like most guys, I started out reading, then watching, straight pornography. Sure, there was the titillation of happening across a cross-dressing tale in the glossy flesh mags, but they were for a ‘straight’ readership, and didn’t quite scratch that... Read full Story
Daddybear71 2023-05-24 7,616 Crossdresser Amateur Masturbation
84%
The Making of Erica - Sperm Loving Crossdresser
Confessions of a Crossdresser I am a crossdresser. It is an addiction. I’ve tried, but I really can’t stop myself: fantasies, endless looking at pornography, shopping, dressing, masturbation, and inevitably, seeking men to please. I have only sucked cocks, but over a hundred at my las... Read full Story
shemale lover 2015-09-03 16,615 shemales Masturbation Fetish
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 5,917 Crossdresser Masturbation Latex Sex Toys heels
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 15,784 Big Cock oral transvestite forced sex
66%
TO BE OR NOT TO BE – PART 5
TO BE OR NOT TO BE – PART 5 by Spanky de Bautumn Part 4. Sunny made a life changing decision and in the process becomes better acquainted with Mark. On Monday, I met Mel and Shari at the theater at ten to run lines. I was confident that I knew my part for the first act. My concern was with m... Read full Story
SpankydeBautumn 2021-02-24 2,209 Crossdresser Cumshot Masturbation Blowjob Big Cock Lingerie Interracial
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 7,440 Big Tits Cumshot Shemale Fucks Guy threesome blonde Big Cock Lingerie Shemale and Girl redhead Homemade Shemale fucks couple
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 4,282 Stockings Crossdresser Cumshot shemale oral sex
77%
Slut indiscretion
At 17, I had reputation among the people in my world. I had sucked more dicks than the average hooker. I had slept with men of every race creed and color. You can even throw in a mentally challenged lad or and autistic child as well. All because I loved getting sex. I think that a penis is the sexi... Read full Story
Regina10 2020-09-16 5,443 Crossdresser Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Ass to 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 5,290 Crossdresser Blowjob Big Cock Shemale and Girl shemale fucks female
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 3,310 Stockings Crossdresser Cumshot Blowjob Lingerie
88%
Caught Crossdressing by a Real Man
This story is a continuation of night club cum slut. Ever since I first wore panties for a boyfriend, I had built up a collection of lingerie. I gradually worked up from panties to the most erotic lingerie I could find. My fascination with cross dressing went a little further with a new fetish f... Read full Story
shemale lover 2013-01-17 35,505 Crossdresser sucking Lingerie ass fucking ass fingering
100%
A surprise for John
It was a busy day at work when I got a text message from John asking what I was doing that night. I replied that I had no plans. He told me he was leaving work early, if I wanted to stop by for a lil bit I was more than welcome. I told him I would. I did want to talk to him about a small trip I was ... Read full Story
shemale lover 2013-07-21 8,077 Crossdresser anal sex Cumshot oral sex kissing
100%
My suit fantasy fulfilled
I've always had a thing for a man in a suit, a really smart suit. Maybe it's a secretary fantasy or something, but I just think every man looks sexy in a suit. So it was with great delight that upon making contact with a guy on Grindr a few weeks back, is profile pic showed him in a suit. While t... Read full Story
hornywilla 2020-09-14 2,996 Stockings Crossdresser Blowjob trans Lingerie kissing crossdressing bj crossdresser fucks hotel room hotel fun cdtv
100%
Camming down the rabbit hole Ch2
How had I ended up in this situation? Sure I was going to need to make ends meet, but I could find a normal job couldn’t I? was I this desperate? Perhaps desperate wasn’t the right word, just over a month ago I had started out camming as a bit of fun, to maybe make a few pounds while I masturbated, ... Read full Story
Dani_does_Dallas 2021-08-11 3,621 Crossdresser solo Amateur Masturbation Lingerie Homemade webcams
100%
A Win-Win
A Win-Win By Sabrina G. Langton *** Author's Note: Hi, just a quick, crazy story about a wife actively participating in her CrossDresser husbands sex life. Just a bit of fluff, hope YOU like it.) *** We were laying in bed, sex was done, my wife could now relax for the rest of the month ... Read full Story
Brina Giselle 2024-03-31 3,934 anal Stockings Crossdresser Blowjob pantyhose kissing salon
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 3,301 sucking cum Sex Toys cd
100%
Party Surprise - First sex as a Crossdresser
This is a work of Fantasy. I hope you enjoy. Stephanie and I had been married a few years and enjoyed a reasonable sex life. She knew of my dressing and although she didn’t approve she indulged me now and then and we had sex when I was dressed or with me wearing lingerie. I think secretly s... Read full Story
shemale lover 2012-05-21 7,510 first time hardcore anal sex Cumshot oral sex crossdressing
100%
Finally A Real Man
After my divorce I found I had some time to indulge in my many fetishes and fantasies. Those being; cross-dressing, smoking 120s and man to man sex. None of these were a factor in my separation however. It wasn't long before I was on line ordering lingerie and shopping locally. This has been going o... Read full Story
shemale lover 2012-08-06 4,817 anal Crossdresser oral
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 5,475 Crossdresser Fetish Lingerie
100%
T Is for Teresa
Transgender-themed stories which I hope will be of interest to those who like women, or would like to be a woman. Which includes me! It was when I was still living at home, or at least staying there in the college holidays, that Mum came home and found me and Jack Horton lying on the living room ... Read full Story
shemale lover 2012-08-28 6,283 Crossdresser Cumshot Fetish Blowjob
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 7,750 Crossdresser Cumshot Masturbation Lingerie heels
83%
Discovering Amber
I have always enjoyed women's lingerie. From looking at catalogs to seeing girlfriends wearing it I have loved the look and feel of sexy, silky lingerie but for me it has always gone deeper. At 18 I tried on my first set of panties, oh my God that was wonderful! It was all downhill from there. Event... Read full Story
shemale lover 2012-09-28 6,188 Cumshot Fetish Lingerie oral sex
100%
Kelly's first cock
I've been dressing on an off for as far as i can remember, starting when i was at school, coming home early and putting on my mum's lingerie and heels and wanking myself off looking at my reflection in the mirror. However, it wasn't until i went to uni that i started to get into tranny porn, where i... Read full Story
kelly louisa 2012-10-16 4,657 first time Crossdresser Blowjob slut sissy
72%
The Weekend
The weekend A story inspired by the very sweet and sexy samantha satine and my beautiful wife Part 1 - The preparation samantha packed her suitcase with her usual attention to detail, makeup, lingerie, wigs, but no dresses. Her head was confused by this, Master D had given her instructions... Read full Story
MasterofSissies1 2018-12-04 8,697 anal tranny Stockings Crossdresser Group Sex gangbang oral domination Guy Fucks Shemale transvestite schoolgirl School uniform maid uniform
85%
The Sex Club
When I got divorced back in 1987 I was a very horny man that had not had sex in many years. I had always liked to dress up in nylons etc and learned long ago that I was Bi and liked cocks and pussy. When I finally got my own place after the divorce I almost always would lay around the house dressed ... Read full Story
crossdresser55 2019-09-11 9,815 Stockings Crossdresser Lingerie Sex Toys
100%
The Best Valentine's Gift
The Best Valentine's Gift By Sabrina G. Langton *** Author's note: Hi, just a little sexy story... cocktails, a three-way and some role play... the usual, I hope YOU like it... *** Ding dong. "Hello," "Sabrina hi, come on in, you are all dressed up and looking fabulous already... Read full Story
Brina Giselle 2024-05-22 2,528 Crossdresser pantyhose transgender high heels bbc three way
100%
Danielle at the Office
Daniel ended his work day like any other; tired, bored and longing for sexual action as Danielle. It was three months since Danielle's first meeting and many a night she'd dress as sexy as she could and masturbated to magnificent heights, all the while moaning Shawn's name. Just the mere thought of ... Read full Story
shemale lover 2012-06-18 2,562 Crossdresser Cumshot oral sex
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 3,230 tranny Crossdresser Masturbation
55%
Dawn's Diary Chapter 3
Back at home it took nearly a week before I was able to sit comfortably after my encounter with Sam and her huge dildo. My thoughts constantly drifted back to her. I continued to keep my body cleanly shaven and regularly wore the outfit that I had worn that evening with Sam around the house. I bough... Read full Story
shemale lover 2012-07-31 3,027 Crossdresser Cumshot oral sex
60%
Brotherly Love, Sisterly Love Chapter 2
"RACHEL" My twin sister, and sometime brother, and I had been experimenting sexually with each other and crossdressing together for around a month, growing to love and to perfect our new feminine personas until they became the ones we thought of as our true selves. Whenever our parents ... Read full Story
shemale lover 2012-09-28 6,581 Cumshot Fetish oral sex cum swallowing
66%
Spring Morning
First morning of spring After the long winter it was just starting to get brighter and greener, white anemones were blooming and in a few weeks spring would be at it's most beautiful phase, but for now the gloom of night and mist was just retreating back to the sea and sun was rising giving me ... Read full Story
Femboy Emmi 2020-05-11 3,592 Small Tits Crossdresser solo Lingerie
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 6,166 Crossdresser Interracial sissy chastity Cuckold Husband
100%
Glory Hole Memories
The Glory Hole Fun Begins Locking the car I look towards the building. The entrance is open, but from my position it isn’t possible to see inside, the bright sunshine making the entrance look black. My heels click on the tarmac as I approach, my legs beginning to tremble with fear and excitement.... Read full Story
Sexy Michelle 2024-03-13 4,346 Stockings Crossdresser Outdoor Blowjob Big Cock Lingerie
100%
Fender Bender Chapter 5
My name is Robert, but when I am dressed I call myself Vicki. I am 5'9" 160 pounds, blonde hair and blue eyes. I had just turned 18. Mom and my Step Dad were away on vacation leaving me home alone. The past several days I had been very lazy and sleeping almost to noon. So it was no surprise ... Read full Story
shemale lover 2012-07-26 3,172 Crossdresser Cumshot Fetish oral sex cum swallowing
94%
Proud To Be A Sissy Chapter 2
As I reached down to retrieve my clothes that Mr. Clark had thrown at me there was a bright flash of light. Without thinking I turned my head towards him only to be blinded by another flash from his Polaroid camera. "What are you doing?" I asked. "Just wanted to capture the m... Read full Story
shemale lover 2012-12-23 7,941 Crossdresser sucking ass fucking domination ass fingering
88%
Becoming Lisa
From when I was as young as 9, smooth and long blonde hair, I was always dressing in my older sister's panties and bra, panty hose. My breasts were kinda girlish and i had long nipples that would get hard when I played with them. I was older now, but still only had a small 4 inch cock when it was ha... Read full Story
shemale lover 2013-08-09 13,053 Crossdresser Masturbation Fetish Lingerie kissing
69%
Motel Blackout
I always enjoy my sales trips. The trips fit into my crossdressing lifestyle and the thrill of being in a different town and different people. After a long day on the road, I had just checked into a motel just about 30-miles outside of Nashville, TN. For my overnight trips, I always bring my spe... Read full Story
browncherrygurl 2017-05-25 18,148 anal Crossdresser ass fucking sissy forced
80%
A New Spin On Role Playing Games
A New Spin on Role Playing Games By: Shawna Summers shawnavinylltv@gmail.com I've always been something of a geek. I love sci-fi and fantasy books and movies; I can recite countless bits of useless trivia back to you about all kinds of movies. So, it was no real surprise that I took to rol... Read full Story
shawnavinyltv 2018-06-14 10,732 Crossdresser anal sex Blowjob gangbang Lingerie bondage
66%
Samantha sissy TGTF
Theme and genre of the story: The genre is about gender bender, futanari, gay, physical transformations of the body, magic and biology, the kink in particular that must excite in the story is the perversion of the transformation of the body and mind through a magical element that manipulates biol... Read full Story
Samantha sissy world 2022-09-20 4,655 Teen (18+) Crossdresser Big Tits transformation transgender feminization pov sissification Cartoon magic Gender Bender
83%
the start of what to cum
I responded to an ad on Craigslist from some guy asking for help to move some furniture. He was paying pretty well and, after I practically laughed at him for asking if I could lift the furniture, he agreed to have me over to get it done. We moved everything around for what felt like hours, often mo... Read full Story
oliviabecket23 2023-07-04 6,747 Crossdresser Lingerie domination Sex Toys femboy forced webcams