Sort by
Relevancy

Free Stories

80%
Vicky Part 1
"Dear Sir, We recognize you as a person of discerning taste. We would therefore would like to invite you to a display we believe you would find most enjoyable." What followed was an address and a date, one week away. My name and address were correct, but I didn't have a clue what they w... Read full Story
shemale lover 2011-11-14 4,338 sucking cum fingering
100%
Alexis Season Part 3
Finally, Alexis decided to take off her shirt, followed quickly by her bra. John went back to groping them, but was kissing at a bit of a faster pace now. He was so delighted that he was showing his appreciation through his kisses, and through his hands. John pulled away from her mouth, no matter... Read full Story
shemale lover 2011-11-27 2,201 Masturbation erotica romance
88%
Stepdaughter's Transexual Surprise Part 2
As I ended the first chapter of my love story, my Stepdaughter Dawn and I were returning from loading a Ryder truck with her possessions. We were to spend the night at home, then continue on to her new place in the morning. We had stopped on the way and enjoyed committing acts of sin by Dawn seducin... Read full Story
shemale lover 2011-12-04 6,864 anal cum facefucking jacking off
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 4,146 cum oral face fucking
100%
Salacious Sarah
Joe Dodge walked down bustling Market Street in Philadelphia in awe. Joe and his wife Tammy moved here 4 months ago from a small town in Alabama. The 24 year old man missed his hometown but at the same time he marveled at the sights in the big city. It was Friday evening, he always went straight hom... Read full Story
shemale lover 2012-05-07 4,675 shemale Big Cock oral sex cum licking
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 6,324 Cumshot Fetish oral sex cum swallowing
100%
"The Arrival" The silly little sluts first Freedom of touch
Based upon Khloe Kay, my imagining if I could be her. { Unedited} a habit to arouse my deepest desires. -Araina Sinclair, Sissy Slut to be. Hope you enjoy. He started to pound my ass, quicker and quicker. Deep long strokes. My boi pussy stretched he started to pull out and slap his head . In... Read full Story
Araina 2021-02-15 1,776 anal Cumshot Shemale Fucks Guy Fetish Blowjob cum Lingerie slut sissy femboy handsfree Khloe Kay
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 5,327 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock gangbang domination cum in mouth
100%
HypnoSissy Partie 2
DEVENIR CUM SLUT Une fois habillé et James parti, Rose demanda: "Vous êtes-vous amusé?" Je hochai la tête. "Oui, bien que je me sente un peu gay." Rose secoua la tête. "Brian," gay "est juste un mot, comme" lesbienne ", ou" faggot "ou" gouine ". J'ai mangé la chatte et demandé aux filles... Read full Story
Femboy 2021 2023-01-24 3,691 Stockings Teen (18+) Crossdresser Fetish Blowjob Big Cock Lingerie domination cum in mouth
50%
The Visit
A visit to a hooker, where I describe my bisexual experiences *** It was a weekday, I had bummed off work and had made my way to Ipswich for a visit to Rona, my favorite hooker. She was a lovely woman in her forties, with a fantastic figure, not slim but not fat and with huge tits. She... Read full Story
shemale lover 2012-01-26 7,997 Group Sex licking sucking pissing fucking
83%
Cindy She Thong
Dialogue from Cindy’s point of View: Her name is Cindy and she is a shemale. Cindy is a beautiful woman is every way except one. She does not like the term tranny and prefers being referred to as a shemale. She is truly happy living as a woman. She began taking light doses of hormones at 19 she had... Read full Story
mrstanley 2015-07-29 4,923 Big Cock ass fucking deep throat piercing
64%
Big Cock Heaven
This story is written from the Shemale's point of view. "Jane" is based on a real Transgender woman from California & my friend. She gave me the outline of a meeting she had with "Janardhan." ***** My name is Jane and I am a natural red head blue eyed 34 year old T... Read full Story
sach 2015-11-16 7,022 Big Cock ass licking redhead rimming Shemale on Guy
66%
Dirty Business Trip
Chapter 1: The Transsexual Hotel Encounter "Yes, I am checking in," I said, putting my credit card on the desk. The woman behind the desk took the card and looked at the name. She was about 5 feet 10 inches tall with dark black hair and brown eyes. Her skin was beautifully tanned and he... Read full Story
shemale lover 2012-09-26 12,577 Group Sex Cumshot shemale oral
85%
Francine Hung Shemale
This is the story of "Francine" a Transgender woman from California. She and Jonathan meet in a Tucson resort two weeks after their first weekend together. Note from Francine-Thank you Mrstanley for writing and submitting my story. In real life I live and work in California and Mexico as ... Read full Story
darrell 2015-11-16 9,155 sucking Big Cock ass fucking deep throat butt plug
100%
Big Dick Alessia Visits Dallas
Alessia Hung Mature MILF travels to visit a Big Dicked Man and his Sexy Household If you like Transexuals, big cocks, bondage, BBWs, big clits, deep throat, fisting, 69, ass fucking, sounding, piercing, cum swallowing and big loads this story is for you. If not don't bother reading. If you fav... Read full Story
darrell 2022-04-20 4,016 Group Sex Cumshot Shemale Fucks Guy Blowjob blonde Big Cock Asian Shemale and Girl Sex Toys Mature Ass to Mouth shemale + shemale
100%
Trying It On For Size Part 2
I looked up and saw the low slung scrotum swaying above my eyes, the long, thick, curved shaft pointing upward just in front of it. I heard a quiet tearing sound,"schshhhtt," looked further up and saw Tanya opening another one of her black foil Magnum condom wrappers. She placed the large,... Read full Story
shemale lover 2011-10-26 5,514 domination bondage anus
100%
Caught by the Past Chapter 3
After sucking his cock you sit on the sofa supported by a fluffy white cushion, shoes kicked off, legs curled under your lap. Dressed like a sissy whore you relax as best as you can, your arse muscle stretched wide open by the butt plug. But you've become accustomed to all the strange feelings... Yo... Read full Story
shemale lover 2012-06-28 3,046 Fetish oral sex crossdressing
100%
Whoring for freedom
It is four o'clock on a Friday afternoon and I have been driving for almost two hours on my way to a cabin in the middle of nowhere. According to the instructions my Mistress gave me, I still have about an hour to go. I have the air conditioner on because it is a very hot day and I have to make sure... Read full Story
shemale lover 2012-11-07 3,939 Cumshot teasing sucking off
100%
Charisma Part 4
Tiffany held one high-heeled shoe to her foot. It wouldn‘t fit, she knew, since the shoe was several times smaller than her foot. Nevertheless, aware of Charisma, who was seated beside her, waiting for her to don the shoe, she pivoted her foot downward, inserted her toes into the front part of... Read full Story
shemale lover 2011-09-04 2,748 Big Tits licking swallowing
95%
My Girlfriend's Mother Has a Secret
A young man, 18, is caught spying on his girlfriends mother in her bedroom, and is taught a hard lesson. Characters: Tim, 18, Student; Susan, Tim's Girlfriend; and Julie, 44, Susan's Mother ;-). Julie sat at her dressing table, preparing for bed; she brushed her long dark, which was one of the pr... Read full Story
shemale lover 2011-10-30 33,583 anal shemale oral
77%
How I Became a Tranny Whore Part 2
After my first night working for Mama T, I was hooked. At least once a week I was a worthless whore at her trailer. I would be at her trailer, ready to serve her cliental. Of course most the Johns picked one of the real girls over me, but there were the occasional guys that wanted some thing differe... Read full Story
shemale lover 2011-11-08 4,140 tranny suck asshole
40%
Lost bet
It all began as a bit of a joke really. We'd all been out clubbing in some raunchy nightspots and were still high on the atmosphere. As the night wore on and morning was quickly rearing its bright and beautiful head, the group began to dwindle until only three of us were left. My husband Phil, my be... Read full Story
shemale lover 2012-04-04 23,819 Stockings Fetish domination crossdressing
40%
Betrayed by Her
I am surprised when Her husband answers the door and mumble hello awkwardly as He smirks at my discomfort. "Come on in," He offers expansively letting me in the door. He stands close while I shut the door steadily forcing me into the corner. "She told me about you," He whispers. ... Read full Story
shemale lover 2012-05-25 3,403 Cumshot domination oral sex sissy
100%
Chrissie Goes Job Hunting
I was fresh out of college and needed to make some real money if I wanted to get my own place and start my business. The job with the limo service was OK but I had to come up with something to supplement that income. Living with Kelly was great but i knew that soon she'd want to move in with her l... Read full Story
shemale lover 2012-06-29 2,940 anal sex Cumshot dildo
98%
My Girlfriend's Mother Has a Secret
A young man, 18, is caught spying on his girlfriends mother in her bedroom, and is taught a hard lesson. Characters: Tim, 18, Student; Susan, Tim's Girlfriend; and Julie, 44, Susan's Mother ;-). Julie sat at her dressing table, preparing for bed; she brushed her long dark, which was one of the pr... Read full Story
shemale lover 2015-02-27 27,039 tranny Cumshot suck Shemale Fucks Guy ass fucking wanking
92%
CD. vacation fantacy
My boss was going on vacation and asked me if I would house sit for a couple of weeks. Since there was no work during that time I readily agreed. He had a real nice place in the Hollywood hills and I get a vacation too. Friday was my first day there and it was big 4 bedroom, 2.5 baths, swimming pool... Read full Story
cdlishmis 2018-06-07 9,379 Crossdresser crossdressing
100%
The Developing of Emma Part 3
She awoke to the sickly smell of a woman’s perfume; the silky stockings were still there, but Emma was now naked apart from a chiffon negligee, her hands bound behind her back. The voice of the woman broke the silence. “Hello again ‘Emma’; that’s a very pretty name y... Read full Story
shemale lover 2012-08-26 2,617 Cumshot oral sex sissy
61%
Uncle's slutboy: the attack of the black men
On the way home from Grandpa would I through a park. Or I would not. but the road outside was sooo long and I felt frankly a bit sore and spent in the ass after being violated by gramps. so I shortcut through the park. After all it was not that bad. Not like those dank places without light and a lot... Read full Story
worshipbbc 2015-12-25 6,472 Creampie interracial sex ass fucking sissy
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 7,708 transsexuals romance crossdressers
58%
My real story
I couldn't believe it. Here I was in bed with an older man – and one that I most wanted as he lay there sated by my ministrations to him. It had all started two weeks earlier when I had posted an ad on Craigslist. Up until this particular posting I had always been pretty bland..."Willi... Read full Story
shemale lover 2012-06-10 6,061 hardcore Cumshot bdsm oral sex
50%
Alex One: House Sitting for a Friend
Sorry, this is a little rough. I've tried expanding the original version but ... i dunno. Anyways this should be a continuing series of some sort. Alex One: House Sitting for a Friend. By Alex Shouse. My friend Karen had worked her way through a somewhat bitter separati... Read full Story
AlexShouse 2012-07-12 3,657 dildo oral transvestite sissy
69%
Sissy School
I arrived at the school at 8AM for the start of my new life. The school had promised a lot when I saw their website but I wasn’t quite sure what I was in for. I had arrived dressed in male clothes with none of my belongings as I had been instructed to on the website. I walked through the gates into ... Read full Story
Sissysophie780 2019-07-04 18,831 humiliation schoolgirl sissy slut punishment School uniform
90%
Becoming a Drag Queen
I was thrilled when my boss told me he was sending me to San Francisco for a conference. It was a location on my "Top 10 places I wanted to go". I went online and Googled the major attractions and tourist "must sees in San Francisco. The conference was Wednesday to Friday and I figure... Read full Story
shemale lover 2012-03-01 13,640 first time sucking fuck domination
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 5,362 Crossdresser Cumshot Fetish Blowjob gangbang
100%
Dottie's Back
Four weeks had passed since my first blowjob party. In that time, I had become obsessed with getting implants. The concept of being tit-fucked and wearing deep-cut tops without being concerned about the distinct line between my flesh and the fake boobs had become a constant fantasy of mine. After be... Read full Story
shemale lover 2012-11-02 3,644 Group Sex Cumshot facial oral sex
84%
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 2012-12-21 118,079 hardcore Cumshot sucking bdsm domination
90%
I am a sissy maid
Part 1 Around the end of my last high school year, my curiosity for crossdressing had just emerged, but I didn’t explore the fantasies too much as I thought it was just a phase. The following fantasy is something I have dreamed about for years… A friend of mine, Peter, was into the same video ... Read full Story
lea1234 2014-03-27 9,370 Stockings suck Uniform stroking cd
94%
Renting out a room
When my wife suggested that we rent out the guest rooms above the garage to a college student it sounded like a good idea. It was very much like a small apartment, with a bedroom, bathroom, and small living room. No kitchen of course, but we could share ours and it seemed like a good way to make a l... Read full Story
Alic91lovesporn 2015-07-29 21,029 suck shemale jerking orgasm domination
75%
My one and only wish...
I can't really explain it, but I love big, fat, juicy cock on a girl. Nothing in this world makes my dick harder than a rock hard cock bulging out of a girl's cum-filled panties. My only problem is, I've never been with a transsexual, but I've always been curious, very curious. ... Read full Story
ColeHD 2015-10-08 4,437 Big Cock cumming swallowing stroking latina ts
57%
Ambers torment
It seem to be the typical day for Amber as she entered the home of Master. The usual early wake up and long drive down to his house seemed nearly routine though, the last visit was a few months past and the girl was anxious for what was to come. Although, her expectations were not different from any... Read full Story
shemale lover 2014-04-19 7,002 shemales Fetish bdsm
100%
Jamie is taken Part 2
Jamie came to on the cold dungeon floor retching and coughing, his mind paralyzed by a mixture of pleasure and panic. He had loved the orgasm he had just experienced. His experience with breathplay was less than half a day old and already he knew that he loved it almost as much as finally ... Read full Story
shemale lover 2011-11-30 3,750 Fetish bdsm fiction
100%
Jennie
Several of the transsexuals who call me Master are, indeed, slutty subs. This is the story of my first meeting with one of them. Having gotten to know her well before our meeting was essential to a satisfying experience for both of us. She came into the room as I opened the door, dressed in sweat... Read full Story
shemale lover 2012-02-15 2,929 suck small breasts toys
100%
Birthday Present Chapter 4
Chapter 13 [We have been busy with our summer schedule and have not had the time to continue this narrative. However, due to the many emails we have received urging us to continue the story, we have decided to return to the task. And task it is. In our effort to accurately relate what happened an... Read full Story
shemale lover 2012-06-17 2,424 Cumshot Blowjob feminization
100%
First Time Being a Woman
My heels clicked on the concrete path as I made my way toward the secluded toilet block in the southern parklands. Tonight would be my first experience being with a man whilst I would be dressed as a woman. I had been dressing now for some time and had fantasised about what it would be like. I didn'... Read full Story
shemale lover 2012-10-08 4,434 first time Creampie Fetish crossdressing
94%
Fooled by the Wrapping
It has been about 8 months now since my husband left me. No big blowup, or much arguing. He admitted he had been having an affair his third. I admitted that I had spent an evening with a young man. He had a long talk, and agreed to move out, we could live our separate lives. I kept the house, he agr... Read full Story
shemale lover 2013-03-28 8,456 hardcore sucking Big Cock Shemale and Girl Interracial
86%
Cindy and Juanita Kinky Shemales
Her name was Cindy and she had been born a male. Cindy was a beautiful woman is every way except one. She didn't like the term tranny and preferred being referred to as a shemale. She was truly happy living as a woman. She began taking light doses of hormones at 19 she had stopped hormones beca... Read full Story
darrell 2016-11-30 10,915 anal Big Cock deep throat swallowing foot fetish piercing
84%
She never saw it coming
When I was 19/20 I used to frequent LGBT bars roughly twice every month. Most nights not much would happen but I found myself going to the trans nights more often. Until I eventually had some experience with trans girls. It was mostly fairly soft fun. Me getting oral and occasionally topping th... Read full Story
chris1989r 2022-02-01 4,827 shemale gangbang facial
100%
Something For Everyone
Josh pulled slowly into the driveway and parked the car. He made as little sound as possible as he closed the car door, and took the same care as he entered the house. He was more excited than he had ever been, but didn't want to spook the people inside. His wife Penny had called him before he left ... Read full Story
shemale lover 2011-10-20 4,317 anal sex Creampie threesome
100%
Secrets
Jon had invited me to spend another weekend at his place with another of his friends. I always find his friends to be interesting so I accepted. Jon had given me a garage door opener and a key to his home after my first visit. He met me as I parked my car in the garage. He was wearing his usual skim... Read full Story
shemale lover 2011-11-01 5,725 anal Blowjob transvestite
71%
Glory Hole Girlfriend
My boyfriend likes to take me to the local adult bookstore, into the back where the video arcade is. There's always a lot of men there, strangers that we don't know, and I feel funny when they look at me. They wonder why a pretty young woman would be back there. It smells too. A rich sweaty sc... Read full Story
shemale lover 2011-12-18 7,067 Creampie ass fucking mouth fuck
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 8,438 Crossdresser anal sex domination oral sex
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 4,578 anal Crossdresser oral
100%
Doggy Style
"OK, which exit is it?" Trish was driving with Penelope in the passenger seat up front. Meredith sat in the back behind Trish's seat with Angela behind Penelope. The quarter were sisters in a sorority attending an annual Alpha Phi event together. Every year different chapters across Sou... Read full Story
shemale lover 2012-10-17 4,952 swallowing crossdressing sucking off
100%
Amethyst: The Girl with a Penis
I stand and look at myself in the mirror. To my eyes I appear to be just an average every day female university student. I have on a pair of blue lacy panties with a matching bra and my mahogany hair is pulled back in a blue ribbon. Hazel eyes stare back at me from a fair complexion as smooth as a b... Read full Story
shemale lover 2012-10-28 4,996 Cumshot Blowjob kissing
100%
Downsizing Chapter 3
Work was going quite well. The company started to grow again, and some new personnel had been hired. Even unknown to me, there had been a couple of males hired in the last few months. Ms. Stanton had informed them when she got to the dress code that the makeup was a requirement, and that the one mal... Read full Story
shemale lover 2012-11-10 2,864 anal sex Cumshot Creampie oral sex
100%
Angel Chapter 4
On Friday morning, Angel Jones woke up smiling. She was happy because it was the last day of the work week, and because there would be a dance at the Gay, Lesbian, Bisexual and Transgendered Association that evening. She had been anticipating the event ever since her first night there, seeing it as ... Read full Story
shemale lover 2012-12-01 3,991 Blowjob condom sex