Sort by
Relevancy

Free Stories

87%
THE ATTIC NOVEMBER 7
THE ATTIC NOVEMBER 7 – PART 1 THE JOURNEY AND GETTING READY. Susan had not had the opportunity to make the journey to the Attic dolled up to the nines so she made do with just wearing her black and pink lingerie under the hideous drab stuff (yuck). Having arrived early and parked up, she relaxed ... Read full Story
sexysusang 2018-03-09 5,691 Amateur Group Sex Bareback Blowjob Guy Fucks Shemale cum in mouth
100%
All Woman and More
It was one of those soft southern nights you hear about in movies and old soft rock songs. I could smell the long leaf pines and the moon was nearly full. I had been on my own for so long that it rarely bothered me as it did in my youth. That lonely feeling that never quite goes away. Now it came on... Read full Story
Windmillchaser 2018-09-20 10,433 Bareback Shemale Fucks Guy Big Cock sensual romantic encounters Erotic Fiction
92%
Dani & Paulie - 2
Devon, it turned out, was a complete gentleman. The accent i couldn’t place was a hybred of south London in the UK and the Caribbean. He’d been in the states for a few years after being spotted as a student, modelling for some extra cash. He’d greeted me on the veranda like an old friend, a hug an... Read full Story
SissyDani31 2018-10-09 3,311 Crossdresser Big Cock Interracial
66%
Oh Samantha
Meeting Samantha for the very first time at the busy theatre restaurant was the best thing that could ever happen to me. She was performing with about 20 other ladies or sort of ladies, I found out later that they were hot shemales, transsexuals and even a few transvestites. Their performanc... Read full Story
iluvgurls 2018-11-12 4,305 Cumshot Shemale Fucks Guy Blowjob Lingerie
92%
MY Party Favor Fantasy
My Party Favor Fantasy A fictional story built around an old fantasy of mine I ran a notice on one of those sex sites that said” Help me fulfill my fantasy and I bet we take care of some of yours also. Hi there, I am Penny and I am a total bottom trans w... Read full Story
pennypenny 2019-01-08 6,999 Stockings Crossdresser Group Sex Cumshot Masturbation Bareback Creampie Fetish threesome Blowjob Big Cock gangbang Lingerie redhead domination Guy Fucks Shemale Sex Toys Ass to Mouth cum in mouth double anal
66%
dinner
3/11/2008 I traveled to the Adult Store about 20 miles away. We have stores that are closer, but this one has more of a selection of lingerie. I picked out a black fishnet mini dress. I went home to prepare. I entered the shower to clean up and to shave very close for my man. I start to use Na... Read full Story
cd4fun715 2019-01-08 1,964 Amateur
100%
Tom Didn't Get A Choice
Tom Didn’t Get A Choice This was Tom and I’s first date. We had met online, so he already knew that I was a very femme sissy crossdresser. Tom eventually asked me on a date. I happily said yes, knowing that I turned him on a great deal. On the evening of our date I wore a black dress that wa... Read full Story
pennypenny 2019-02-18 6,052 Crossdresser Cumshot Bareback Creampie Blowjob redhead Guy Fucks Shemale cum in mouth
87%
First time crossdress with a friend
My lovely new Malaysian friend emerged from the bathroom, shyly in the low light. He was wearing thigh-high stockings, cute little panties and a matching top that was tied at the front. My heart leaped at this gorgeous site. He had advertised that he wanted to hook up with someone who appreciated... Read full Story
AsianCDLover 2019-05-27 4,586 Crossdresser Masturbation Asian Interracial
100%
Masturbation fantasies 2: Looking for Amanda
Previously: William, a young lawyer who has no luck with women, decide he needs some relief from a live girl. Scared of going with a prostitute, he decides to try out a peep show first. Without knowing that the stripper he chose is kind of special, he ends up in a show with a shemale called Amanda w... Read full Story
ThatEroticWriter 2019-07-24 8,687 Big Tits Cumshot Masturbation threesome Frottage
60%
Winsome Morgan
I’m not generally one for parties, but my very good friend Josie invited me to her open house to celebrate her new home. It’s quite lovely, and has a nice veranda to a deck to an in ground swimming pool. From the living room there are sliding doors that take you out to the pool. To the right is th... Read full Story
lissomlover 2020-09-02 3,802 Small Tits lesbian skinny
95%
My best friend turned trans.....so I fucked him - Part 1
Theres a bit of history to this one so strap in! I started hanging out with this group of kids in my area when I was 12 years old, we did all the typical stuff you can imagine young kids getting up to (played football, chased girls etc...) over the years I became really good friends with one of the ... Read full Story
iconicirish 2023-05-11 8,407 Stockings Amateur cock Masturbation sucking Blowjob Big Cock Lingerie Latex transgender sissy
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 6,453 Crossdresser Lingerie domination Sex Toys femboy forced webcams
83%
Natural Born Bottom Boy
All my life I imagined how much I'd love sucking tranny cock. Never thought "if" I'd enjoy it, it was how much would I enjoy it. At the start of puberty I always liked women, but pussy seemed gross. Thought I'd suck some dick but I'm not attracted to men at all. Then I stumbled on my first tranny po... Read full Story
KendraK 2023-11-03 6,428 Amateur
100%
The Massage
The Massage One afternoon I decided to get myself a massage, a deep tissue one as really needed it. I had asked a friend of mine to recommend a masseuse and she said she would make an appointment with her friend, Pat who was a masseuse. I arrived for my appointment and was greeted by a very cute ... Read full Story
Lacetoface 2024-05-13 1,239 anal Shemale Fucks Guy
100%
And I Love Cis Girls Too
This is a fantasy I wrote for a cis-gendered woman I met in a chatroom who simply asked me what kind of titties I like. My hope is that reading it might make someone as horny as it made me while writing it. Enjoy. I like your tits. I'll make this as clear as possible. Your breasts are ex... Read full Story
Hardrock51Fifty 2024-05-15 463 Amateur Big Tits Cumshot Masturbation Big Cock
77%
A Night i will Remember 4 Ever
About six months ago I went to a transvestite bar and dance club in the centre of the city where I live. I was dressed in my sexiest all-leather shift minidress, sheer stockings and 4-inch stilettos, and my favourite blonde wig. I was fully made up with long false eyelashes and blue shadow, painted ... Read full Story
bigtranslover 2013-12-19 7,327 anal shemales Group Sex
73%
How I got started dressing
I was a sophomore in high school and like any teenage boy I was extremely horny. I masturbated atleast once a day usually 2 or even 3 times because I had so much time on my hands. I started off watching plain straight porn but I watched so much of it daily that I started to get bored of it. I just u... Read full Story
bigtranslover 2014-02-09 7,359 first time shemales Masturbation
77%
Changes
A story about a mysterious change and how it changed the life of two people forever. The sunlight practically burned my eyes as I slowly woke up. I blinked several times and closed them again for a moment. I felt like crap, way worse than I should have. Last night the guys and I had gone to the bar... Read full Story
bigtranslover 2014-02-11 5,834 female transformation
52%
An Office Party I'll never forget
I've worked for a large insurance firm for twelve years.I`m their top salesman, every year -salesman of the year. Am I cocky... you bet.I`m the best salesman, and everyone in the office is lucky to have me there. Now the ladies there always look so fine, and I get my share of skirt with most of them... Read full Story
bigtranslover 2014-02-15 7,173 transsexual sex change
100%
Stacy
I had known Stacy for about three years, but I had never known about her little secret. That day when it was revealed changed everything for me, and for Stacy too. We were the greatest of friends, spending almost all our time together. We had come as close to each other as lovers but as two women, n... Read full Story
shemale lover 2014-03-25 6,078 shemales taboo
100%
More Dirty Sex with Tania. Part Two
Luckily most of the guests at the Premier Inn had now checked in so when we both went down through the reception area it was again deserted except for the receptionist who only acknowledged the door key being placed on the counter. There were a couple of people in the car park but most were only int... Read full Story
shemale lover 2014-04-09 4,824 anal shemales Masturbation
94%
Shock and Awe
My name is Frank and I’m a decent looking Irishman in my mid 40’s. Every now and then my work takes me to London for a few days and I like to let my hair down if I can. I try and find a hotel in the Earls Court area so if the mood takes me I can visit one of the many hookers that has apa... Read full Story
shemale lover 2014-05-15 6,231 shemale caressing
95%
A Trip to the Beach
I had known Stacy for about three years, but I had never known about her little secret. That day when it was revealed changed everything for me, and for Stacy too. We were the greatest of friends, spending almost all our time together. We had come as close to each other as lovers but as two women, n... Read full Story
shemale lover 2014-10-19 5,238 shemale oral
85%
The invitation
The envelope was waiting on the mat when Jack and Sally got home from college to the small house they shared in North London. Sally scooped it and what was obviously yet another bill up from the floor and plonked them down on the table in the hall as she shrugged off her coat. The young pair were se... Read full Story
shemale lover 2014-12-15 6,586 shemales Fetish
100%
The Holiday Cottage
I really needed to get away from it all. I guess it was a bit of a cliché but I had been working really hard and having no leisure time. I built up a lot of holiday and My boss insisted that I take some and relax and forget about work for a while. I lived for work and so forgetting it would b... Read full Story
shemale lover 2011-06-18 5,991 ass hole
91%
Lakeside Awakening
If anyone had told the way I’d meet my soul mate a few years ago, I never would have believed it. It was my senior year of high school and I had recently gotten out of yet another bad relationship with a girl. Lina had been a pretty, chubby blonde with a nice personality but a nasty temper. We... Read full Story
shemale lover 2011-06-27 7,277 ass Blowjob shemale
78%
Emily and Jane
I'm very proud and happy to publish another jewel today, a story about two shemales from 26-th century, Emily and Jane. Props for this truly delightful story to our forum member, Ila. Excellent work bro! It is the 26th century. Human genetics has advanced to the point where anyone born male or fe... Read full Story
shemale lover 2015-04-11 4,192 anal licking cock sucking
90%
My Secret Girlfriend
I've been roommates with this weird guy named Casey for several months now. He's pretty quiet and doesn't bug me, but I feel he might be a bit... insecure. Earlier I'd be working on laundry and some girly clothes like panties and bras would get in. At first he said it was his sister's (who had staye... Read full Story
RedCircle 2011-07-18 4,636 tranny Cumshot sucking
76%
How I became a GURL Part III
Now that I was fully versed in being a gurl, I needed to know if I could turn a man on in person, not just looking through a glory hole. I wanted to have a man treat me totally like a woman, take me to a hotel and make love to me, completely as a woman. But where to find the guy? The answer wa... Read full Story
shemale lover 2016-01-24 5,383 first time shemales Cumshot
93%
The Babysitter Chapter Two
Over the next few weeks, I could hardly think of anything but the idea of wearing girly clothes and how sexy it would feel. Every house I babysat at now, I would not just go through the underwear, I would dress up in it. I began to build up quite a collection of soiled panties stolen from the women ... Read full Story
shemale lover 2016-03-06 17,160 tranny Teen (18+) jerking off
94%
Sex Ed Chapter One
My husband and I had quite an open marriage. We were both fairly sexually adventurous and this was reflected in how we both considered it to be ok for us to be going out and sleeping around, provided we were completely honest about it and came home and told the other one all about it. In fact, after... Read full Story
shemale lover 2016-03-08 6,389 pussy orgasm crossdressing
44%
Halloween Disguise
an original story by me. its not true more of a fantasy... this story starts october 14th. first of all i am a 23 year old boy, i just moved to a different state to go to college, i dont have many friends and have only been her a couple of months. today was like any other day, had to wake up e... Read full Story
shemale lover 2011-08-07 4,369 first time shemales gay male
84%
Fucked by a Shemale
My names - and I would like to tell you about a very sexual experience I had recently. First I would like to tell you I’m 30 years old and never had a gay experience, until now. It was a Saturday night, me and my brother were round the local town, after a few too many beers my brother met a bi... Read full Story
shemale lover 2011-08-18 168,603 first time shemale cum
71%
A Shemale Christmas Carol
I got a job working as a mall Santa at the local mall during the Christmas shopping season one year. It had been a real shitty year for me. My wife of almost twenty years left me for a younger man, I lost my other job due to layoffs and, on top of all that, my doctor diagnosed me with high blood pre... Read full Story
shemale lover 2011-08-28 4,349 asshole sucking Big Cock
100%
by a Shemale Part 2
I was awaken early Monday morning when Felicia lightly kissed me on the cheeks and said it was time to start my hormone regimen. I looked at her and she had her left hand opened and she had a white pill and in her right hand a glass of water. I was no longer fighting or resisting especiall... Read full Story
shemale lover 2011-08-29 5,789 anal sex sucking shemale
100%
Sudden Shemale
I woke up from the anaesthetic, still very groggy and uncertain. I couldn't remember anything, and my head and body ached terribly. I glanced around, trying to lift my head off the pillow, but it just didn't work. After a few minutes, I tried again, and this time I managed to stand up. I was ... Read full Story
shemale lover 2011-08-30 5,551 asshole pussy Big Cock
79%
My Shemale Stepmother Part 1
My parents split up when I was eighteen, I was a little distressed by it but we had never been as close as some. Still, I didn't really see what had driven them apart so quickly and so thoroughly that they never even spoke any more. I guessed maybe one of them must have had an affair and that was re... Read full Story
shemale lover 2011-09-01 18,581 tranny Big Cock jerking off
75%
A Shemale Vacation Part 3
At the French border, it was discovered that we had no passports. We were taken from the train and into a room for questioning. All four of us, Josh, Olly, Harry and myself, were terrified. Sure, we'd been in a sticky situation before on this trip, sticky particularly for me rather than the others, ... Read full Story
shemale lover 2011-09-05 4,054 anal sucking cum
84%
How I became a Transexual
I was driving a different way home after work and noticed a kind of sleazy looking sex shop. Not really wanting to go home yet, I decided to stop, it had been awhile since I'd had sex and was horny. I went in and was browsing around the movies section when I noticed there were doors in the back. I w... Read full Story
shemale lover 2011-09-06 20,618 asshole Masturbation cum
80%
How I Became Vanessa Part 1
I was a man before becoming Vanessa, and my name was Mike. I was heterosexual and I was going out with my first "serious" girl friend for two years when all this started. I was still living with my mother who had been divorced for a decade before getting remarried. Her new husband moved to... Read full Story
shemale lover 2011-09-09 4,211 anal sex shemale dildo
97%
Shemale Runner
This is based on a real life experience and is about consenting adults engaging in sexual activities, if you are offended by such themes as shemales then do not read on any further. I try to stay fit, I run every day after work for an hour. There is an old dirt track walking path that links fa... Read full Story
shemale lover 2011-09-11 9,146 anal facial oral sex
100%
Pearly Whites
"Ms. Gastlon, your 2:00 is here." "Thank you Barb, please just send him on back." My dentist practice, 'Pearly Whites', is a huge office which works more like a business building. Barb is my secretary and Jack is my assistant; but we'll get to him later. I specialize in cosmet... Read full Story
shemale lover 2011-09-13 3,124 sucking Big Cock face fucking
100%
Shemale Fantasy - Suck Fest
This story is completely fictional - in fact it is a fantasy of mine that I will describe in great detail, contact details are at the bottom if you want to make this a reality! I arrive at your house on the evening. You let me in and show me to the spare bedroom. I walk in and close the door behi... Read full Story
shemale lover 2011-09-13 5,062 Cumshot jerking off pantyhose
100%
CD Business
I never enjoy going to business conferences. They so cut into my time and freedom. And I never meet any cool people. I would not have been there if I didn't have to. The first day drug along at a snail's pace. I was ready to commit hara kiri by then end of the day. Luckily the hotel had a well st... Read full Story
shemale lover 2011-09-28 3,248 Cumshot oral sex cum swallowing
100%
Connie at an Adult Bookstore Part 2
Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. * In the previous c... Read full Story
shemale lover 2011-09-30 8,343 Big Tits Blowjob deepthroating
50%
Courtney
OK, here's how my recent visit with Courtney went. I wanted to see her around 3:00, so I called to ask if her afternoon was open. She said I could come over, and asked me if I was only interested in oral. I was a little surprised she asked that over the phone, but I said "No, I want anal too... Read full Story
shemale lover 2011-10-05 2,223 asshole sucking shemale
85%
Lilly's Cock
Arriving at Wayne's house just after midday, I could hear voices and music coming from the back of the house, so walked down the side passage and through a gate into the back yard. There were about twenty people there, some in the swimming pool, some standing around the barbecue, others sitting on d... Read full Story
shemale lover 2011-10-08 4,048 shemale oral sex cocksucker
100%
Adult Porn Shops Part 2
Well after the drive home I pretty much just sugar coated everything that had happened at the store in order to not beat myself up mentally. But after receiving a blowjob like that and the experience I had wanted more. It was official, curiosity had killed the cat. Hell it ran the cat over because I... Read full Story
shemale lover 2011-10-09 3,256 anal oral gay porn booth
62%
All Night Forced Sex Part 1
I woke up in the morning at half six had a shower then got dressed. Then I was off to uni I drove to uni as I do every morning. I then had a pretty normal day at uni during our 2 hour break between one of our lectures we all went for a drink and got pretty drunk before going it was a good laugh as e... Read full Story
shemale lover 2011-10-09 9,374 cum dildo domination
92%
All Night Forced Sex Part 4
When I woke up all I had on was very small running shorts that had a slit up each side and a t-shirt. The shorts were unable to contain my hard-on so I let it stick out the bottom. No one was around and it felt nasty hot. I snapped out of my daze and began to panic just as she opened the door. &q... Read full Story
shemale lover 2011-10-10 14,224 asshole shemale cum
100%
All Night Forced Sex Part 9
When I went back for my next therapy session. I was surprised to see that Stacy was not alone she was with a plump strawberry blonde women with enormous breasts and a round pink face. "Hi, today we have a guest that will help me with the hypnosis" The woman said to me "Hi my ... Read full Story
shemale lover 2011-10-10 3,037 dildo orgasm oral sex
50%
Realization vs. Reality
So…here I sit. 40 years old and revisiting the confusion of my youth. I am, and always have been, a first string heterosexual male. From my earliest memories of when I began to notice girls, I have always delighted in the wonders of women. I became sexually active at age 16, and there has nev... Read full Story
shemale lover 2011-10-18 3,405 sucking shemale cumming
93%
The Babysitter's Secret Part 2
Two months had passed since Jenny and I had first made love on that fateful, snowy night. At least once a week, occasionally many more, Jenny and I had found time to be alone and indulge in our secret affair. I had never believed any sexual experience could be greater than our first time together bu... Read full Story
shemale lover 2011-10-24 6,469 Stockings shemale oral sex bisexual
50%
A T-Girl Fairy Tale
Jared tossed the last bit of horse manure onto the highly stacked wheelbarrow. With a heavy sigh he gripped the handles and lifted. His muscular arms strained and bulged as he pushed the unwieldy load out the stable door to the large pile where he would deposit it until it was needed for the gardens... Read full Story
shemale lover 2011-10-26 5,396 anal first time Big Cock oral
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 4,084 Cumshot sucking fingering
100%
Lana: First Encounter
Well, I occasionally surf Craigslist in the Casual Encounters section clicking on the t4m button. More often than not I see the regular posts. No one over 35, big cock, muscular a +, face pic a must, no cock pic, 420 friendly, you must host, etc, etc. I wonder, ‘what are these people thinking?... Read full Story
shemale lover 2011-11-11 3,860 cum oral nylons