Sort by
Relevancy

Free Stories

96%
A New TS Slut is born
There I was, one week before the end of high school. Going to college in the fall. Nice car, good f****y, friends. I had it all. So, what was I doing on my hands and knees in a video booth on the wrong side of town, dressed as a cheerleader with a cock in each hand, one in my ass and one buried i... Read full Story
shemale lover 2014-01-29 9,133 Cumshot suck ass fucking oral sex Guy Fucks Shemale
100%
CD new sex friend
Tyrone is a tall skinny black guy 22 years old and his Mel is short and pudgy. I am an older white sissy. I wear female clothing under my regular clothes all the time. Saturday morning I went to the small house they rent and brought an overnight bag. Tyrone opened the door and I walked in. I s... Read full Story
shemale lover 2014-07-31 4,926 Creampie ass fucking ass licking Interracial cd
87%
My 1st time with a shemale
I always had the fantasy to be with a shemale, and today i gained the guts to go to a shemale. I saw the add in the newspaper and called, she was a brazilian (ussually the best ones are brazilian :) ) When i arrived to her apartement, she had a beautifull lingeri, and i noticed her big tits, my co... Read full Story
zongf2008 2014-09-02 4,854 first time ass suck shemale dildo
100%
Double Anal With a shemale
....He answered the door and there she was beautiful as ever. He had just paid 500 dollars to have a transsexual e****t come directly to his door and greet him. She had on a long pea coat and thigh high boots. When she took the pea coat off all she had on was a one piece swimsuit. Her tits were a 36... Read full Story
shemale lover 2015-04-29 5,393 tranny suck Big Cock ass fucking dp precum
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 9,456 sucking Big Cock ass fucking deep throat butt plug
87%
My First Crossdresser
Only a few years back in my young 20's i discovered Craigslist. I had no idea something like that existed and was immediately drawn to it. After building up the courage to meet up with a few guys a couple times i found an add in the T4M section. I got instantly hard when i seen this girls pictu... Read full Story
IrishJames 2016-09-09 10,800 first time ass Crossdresser cd sissy deepthroat
91%
My wife found out I also love cock
Even though I've been a tranny lover since I was 18 I ended up marrying Barb she had a set of tits and an ass built for speed. I never told her about my past nor did I pump her for her past. We had been married for a couple of months when I got that need for big black cock again so while Barb slept ... Read full Story
In Need Of Some Huge Black Cock 2019-04-30 9,256 Stockings Big Tits Creampie Big Cock cum in mouth double anal
50%
There is love, but war
All characters in this story are eighteen years of age or older.* *The following story is inspired by Miss Evie Hyde's "Slut-Box Challenge" story. The following is written with permission from her to use her premise with my own characters and situation* Billy checked his phone when he got th... Read full Story
ASSEaster5678 2019-07-04 3,484 Guy Fucks Shemale bullies
100%
Aquick encounter with an Escort
Two years ago my wife and I were downtown, so I picked up a paper. While scanning the escort adds I noticed a picture of a beautiful long haired girl kneeling in such a pose as to cover up all her private areas. Reading the caption, I was shocked to learn that I was looking at a shemale. I c... Read full Story
Hunter043 2022-04-12 3,046 Amateur Latina Asian cum in mouth
100%
Used in a hotel room
This is a recurring fantasy I have about being used in a hotel room. I’m working on making this a reality but for now this will have to do. I travel a lot for work and end up in many cities across the world. Usually I am out and exploring bars and restaurants. Always ends with me jerking off alo... Read full Story
slvr2291 2023-01-11 4,664 anal first time Big Cock fantasy Surprise
100%
How I sucked my first shemale cock
It was the beginning of the year 2023, in January, three days after New Year's Eve. I was driving home in the morning from a party 100 miles away from my hometown. On the highway, after going half the distance, I received a notification from my dating app, and I was like, "Oh, a new match", I'll che... Read full Story
cock&heels69 2023-05-25 8,716 Stockings cock Masturbation sucking Blowjob shemale orgasm oral sex porn high heels cum shot first experience
100%
mushrooms in all shapes and forms
Mushroom season is open! Yummy! I love mushrooms, in all shapes and forms. We were about fifteen mushroom lovers who only get together to pick mushrooms, without any other friendly gatherings! For this last outing of the season, our splendid instructor was accompanied by her cousin, who was sup... Read full Story
hippocampus_171 2023-11-24 6,510 Small Tits Amateur Cumshot Mature small cock big ass bisexual cum in mouth bald men glabrous
50%
Larissa blond blown in Frankfurt
Very friendly already on the phone. She was very chatty. Asked when I wanted to come and I said at 12:00. I meant if she squirts and she answered yes, but costs 50 € extra. She then said that at 12:00 maybe her landlord will come, the bed would be broken. If he hadn't been there by then, we would ha... Read full Story
Bigpruegel69 2023-12-17 5,209 Cumshot Masturbation Creampie Blowjob cum in mouth
81%
My first time with a guy
MY FIRST TIME WITH A GUY Another true story it’s kind of long but I think you will enjoy it I lived west of Lake Worth Florida. At that time we were surrounded by 1500 Acres of woods. There were 10 of us and we all had dirt bikes and would go out riding all the time.. On Saturdays we had a game ... Read full Story
Stephanie101 2024-04-26 3,948 anal Crossdresser Outdoor Blowjob cum in mouth teen (18+)
86%
Passionate Sex with a Beautiful Shemale
a man and his shemale lover get down to business Will led Sarah by the hand into his bedroom. He closed the door as they entered and pulled her towards him. He placed his hands around her, caressing her toned stomach as he slightly nibbled on her earlobe. He could feel her trembling in his arms. Sa... Read full Story
shemale lover 2014-03-23 6,625 anal Blowjob shemale orgasm fingering
86%
9 ladyboys gangbang me and force me to suck their cocks in my fa
Our forum member, Dutchboi, had this fantasy of being dominated, sissified and humiliated by nine Asian ladyboys, with Mint and Nancy being two of them. For some of You this story may sound too cruel, others will find it really hot. My fantasy is to be at a ladyboy's apartment and fall alseep aft... Read full Story
shemale lover 2015-03-03 10,719 anal Blowjob Asian
100%
Buffy the Shemale Vampire Slayer Part 12
The demons found exits in the walls or floor, vanishing between chinks of stone or through hidden grates or into holes they'd dug for themselves over the long centuries of their residence-or imprisonment-in Baphomet's palace. Only one remained. "My former consort, Baubo," Baphomet intro... Read full Story
shemale lover 2011-08-21 4,562 hardcore asshole Big Cock
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 9,341 anal facial oral sex
100%
Special Shemale Fun
Everyone in the hallway jumped slightly, turned and quickly looked at the tall girl near the sound of the slamming locker. Satisfied that there was no crisis at hand, the kids at the school mostly went about their business. Of course, there were the few admirers that glanced at the girl at the locke... Read full Story
shemale lover 2012-02-06 5,229 sucking shemale massage
80%
A Drive in the Country
It had been a rare hot dry day and the evening promised to be hot as well. Toni the lovely CD I have met down here in Wales arrived as arranged just before dusk in his car to collect me and take me somewhere secluded he had found for some outdoor fun. We drove about a mile before Toni pulled over... Read full Story
shemale lover 2012-02-29 3,861 Stockings Blowjob huge cock wanking cd
100%
A Job in the Theatre Chapter 8
Sarah smiled at her. "Oh yes dear. I will be happy to teach you. Don't worry about a thing. I will show you how to be the best damn girlfriend he has ever had." Paula was so relieved to hear that. If anyone could teach her how, it was certainly Sarah. "But first...first you need to he... Read full Story
shemale lover 2012-03-13 2,457 shemale cum oral sex
87%
A Job in the Theatre Chapter 11
It was a short flight thanks to Ted's private jet. A limo met them at the airport and drove them to a very exclusive clinic. They entered through a private entrance and were greeted personally by the doctor. Paula felt somewhat foolish wearing her "breasts" but was sure the doctor understo... Read full Story
shemale lover 2012-03-13 2,639 Cumshot shemale stroking
100%
A Not-So-Small Piece of Heaven Chapter 2
I awoke the next morning and groggily rubbed my eyes. I tried to remember everything that had happened the night before. It all came flooding back to me. I remembered going to dinner with Vicky, her spraining her ankle, us coming back to her apartment, the initial kiss, the trip to the bedroom, and ... Read full Story
shemale lover 2012-04-28 2,645 anal sex Cumshot oral sex
100%
Shemale on wheels tour
Being a sexy naughty city girl like myself…I get allot of attention from the boys. I always enjoy getting the attention of the small town boys that are not used to seeing a sexy bitch like me roll though town. They jerk off to girls like me online all the time. But having me right in front of... Read full Story
shemale lover 2012-05-17 3,574 anal sex fingering domination oral sex facefucking
75%
The Succubus with a Cock
His cock felt so good between my lips. I savored every inch with such great passion he moaned and fucked my head farther down his shaft. I gagged many times but I was getting better at deepthroating. His balls were coated with my saliva, and soon the couch we were sitting on became wet to. I really ... Read full Story
shemale lover 2012-05-18 8,017 hardcore anal sex Cumshot cum swallowing
87%
Wife fucked by shemale
This is the story of me Rittu married to a guy named Harvinder in 1996. We had 2 kids from our marriage .Harvinder was very fond of girls and even before my marriage he use to fuck prostitutes right from young girls to middle aged women. He used to get his cock sucked and even used to fuck these pro... Read full Story
shemale lover 2012-07-30 7,176 sucking shemale fucking
100%
First Time as a Cum Slut Chapter 2
The next day I was very excited and nervous. I put on black stockings, black lacy panties, matching bra, padded it out, and put on a pale blue top with a short flared pleated grey skirt. As I walked along to the spot, I had butterflies in my stomach and nearly turned to go back home, but he appea... Read full Story
shemale lover 2012-10-05 2,991 anal cum oral crossdressing
66%
An Ass to Die For
It's a very strange thing. We all have our personal quirks. The things that make us unique and stand out from the crowd. I've just never met anyone besides me who has mine before, and to tell you the truth I'm not sure if it's a gift or a curse. You see, I have a girl's ass and not just any old girl... Read full Story
shemale lover 2012-11-13 4,092 big dick sucking porn
93%
Hot Sex in a Blizzard
All flights had been canceled indefinitely because of the blizzard, so I checked in to a hotel close to the airport until the weather cleared. I showered, called my wife, and put on my standard traveling clothes: jeans and a sport coat. The restaurant in the hotel was supposed to be pretty good and ... Read full Story
shemale lover 2013-01-10 5,890 sucking Blowjob ass fucking ass licking handjob
94%
Cum drenched afternoon
I was anticipating Marla's return from her work related trip out of town for a week. She was due to arrive around four in the afternoon. I wanted to make sure I was ready, so I spent the day preparing myself. I took a long hot bubble bath and made sure I was completely shaved. I sprayed on body spra... Read full Story
shemale lover 2013-05-08 7,062 Cumshot sucking ass fucking deep throat stroking
84%
Shemale Gangbanged
Hi........readers.......i am a shemale whose presence looks like an angel.......Due to my physical appearance....boobs,ass....whatever boys use to look at is as soft as cream.My story starts with a mistress ....who fucked me twice....but without any payment...So it was a summer and i called him to p... Read full Story
shemale lover 2013-07-02 6,186 hardcore Cumshot shemale gangbang ass fucking domination 69
92%
Shemale feet
Hi, im a 20 year old european guy with a true great story I wanted to share with you people. It all happened on a warm but rainy day in the summer, was single at that time. I broke up with my girlfriend because we didnt came along anymore. Anyway, I was bored, not to many options and everyone els... Read full Story
Antwerptslover 2014-12-03 8,752 first time ass shemale Big Cock feet
94%
Shemale Ride Along Part 1
I'm going go ahead and get this out of the way. During my freshman year of college, I was confused about my sexuality. It sounds strange saying this right after calling myself confused, but I loved girls. I really did. I loved all of their shapes and curves. I loved tits, pussy and ass. Now... Read full Story
qtball 2016-08-29 12,470 anal tranny Blowjob Big Cock bj asstomouth
50%
She also conquered my soul...
Initiation in a new era... Almost three months since I offered my virginity to a wonderfull he-woman, Selmi... unfortunately I had to cancel the second day we planned to spend together with my LORDESS because I quitted the town where we met the day before. Since, only few summer fling messages...... Read full Story
hippocampus_171 2022-11-22 4,043 Crossdresser Amateur Cumshot Masturbation Creampie Blowjob redhead domination Sex Toys Mature Homemade Ass to Mouth cum in mouth
98%
Shemale on Shemale
We were in the back of a taxi, our tongues deep in each other's mouths, tasting and sucking and swirling. My hand slowly moved up her perfectly toned thigh and under her skirt. I lightly caressed her half hard cock through her thong, barely touching her, just tenderly stroking with my fingertips. Sh... Read full Story
bigtranslover 2014-01-27 6,876 ass cock shemale
100%
My Girl Friend and A Shemale
I walk up to the door of my girlfriend’s apartment. As I start to slide the key into the lock, I can hear slight muffled noises from inside. As the door slowly opens, I am met by the sight of my girlfriend laying with her legs spread wide open on the couch and her super sexy friend Shayla, w... Read full Story
tgirlloverme 2011-09-07 7,572 threesome shemale oral
74%
Sexy Young Shemale
When I was twelve my next door neighbors Sam and Ted trained me in the art of cocksucking and creamy yummy delicious cum eating for hours everyday during my summer vacation and I fucking loved it! I was small framed and wore my long blonde hair in a pony tail and always wore my smallest shorts so I ... Read full Story
shemale lover 2018-09-28 10,584 sucking Big Cock cum swallowing
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 18,938 tranny Big Cock jerking off
100%
A Job in the Theatre Chapter 5
An hour later, with a few drinks behind them, they heard a knock on the door and Paula knew it was show time. Sarah introduced her two friends to Paula and then fixed drinks for everyone. Paula fought back pangs of nervousness and tried to remember all the things he had learned from Sarah to cond... Read full Story
shemale lover 2012-03-12 3,071 suck cum swallowing
100%
A Job in the Theatre Chapter 6
Paula fell back against the couch and closed her eyes. What a marvelous experience it had been! She absolutely loved to suck cock! She loved everything about it. She loved the taste of cum too. She couldn't wait to do it again. She could feel the dried sperm caught in her hair and knew there was ... Read full Story
shemale lover 2012-03-12 3,066 Stockings anal sex oral deepthroating
100%
A Job in the Theatre Chapter 15
Making Gary my bitch Paula got to the theatre early Thursday and got dressed and did her makeup. There was still at least an hour before the curtain went up. She knew Gary would be waiting for her in his dressing room. She knew his cock would be hard too. She could just imagine the thoughts going... Read full Story
shemale lover 2012-03-15 2,252 sucking cum massage kissing slurping
100%
A Job in the Theatre Chapter 19
"Be a dear and get that bag from the car," Paula winked. "Sure," Billy said stuffing his erection back inside his leather pants. He stood, and for just a moment, was right next to Gary, almost touching. Gary could feel the heat waffling off of Billy. He looked so obscene with ... Read full Story
shemale lover 2012-03-15 3,046 anal sex shemale stroking shaving
100%
A Night of Makeup, Cock and Cum
It was all I could do not to accept. After all, it's been a fantasy of mine for years. When given the opportunity, I had to go for it. I had been surfing the internet for crossdressers, shemales, transvestites and transsexuals. The idea of a hot woman with a cock had always turned me on. Further,... Read full Story
shemale lover 2012-04-18 4,745 Cumshot jerking off domination Sex Toys cum swallowing
88%
Mom's girlfriend has a fat cock
When I was a teenager, my mother got remarried...to a woman. At first it was odd, because their roles in the relationship were so clear. My mother was the "bottom", and Jamie was the "top". They're great to each other, and I have grown to love Jamie unconditionally. I'm eigh... Read full Story
TripFontaine 2012-05-14 15,667 anal cock shemale cum tits lesbian
100%
Black Cock & Birthday Presents Chapter 5
"Hi, Baby!" my wife said then ran across the cavernous hotel suite to hug me. "There's cum leaking out of me everywhere I said. I ruined your dress." "Stop it...naughty girl," Angela said. She pushed my hand between her legs to feel her sopping pussy. "You've... Read full Story
shemale lover 2012-06-26 2,610 anal sex facial domination facefucking
100%
Black Cock & Birthday Presents Chapter 6
We went back to our suite. I had no idea what time it was. I'd forgotten how many cocks I'd fucked. It was comforting to see an empty bed when she put me down. When I awoke, I was being spooned, my head under the chin of the black man holding me. His skin seemed familiar but I didn't recall anyon... Read full Story
shemale lover 2012-06-26 2,773 anal sex Cumshot domination
71%
TGirl Initiation by 3 BIG BLACK 12
In my teen years I was often told that I was quite feminine.The high school punks always told me that I filled out the back of my jeans in a girly way. After taking a shower one day I did notice that they were right, I had a nice white bubble butt. Not to mention that my lips were also quite girly. ... Read full Story
TgirlJill4BBC 2013-06-04 9,070 Stockings Cumshot suck Big Cock Lingerie Interracial Latex
88%
Shemale Ride Along (Part 3)
It was the last day of classes. All of the finals were finished, and everyone was celebrating. My finals had been particularly rough. It was the last semester of my freshman year and I didn't study as much as I should have. The problem was that I lived next door to a girl that I had been having... Read full Story
qtball 2016-09-26 21,467 anal tranny Blowjob Big Cock bj Ass to Mouth
100%
I met a guy in the nightclub and I didn't tell him I was Trans
I’d worn an absolutely killer dress just to make sure I got what I was looking for that night. Dancing under the lights I could feel eyes all over me, and as the evening progressed men became bolder and bolder about approaching. This one was athletic, sexy and had all the right dance moves, at least... Read full Story
Madison Heights 2023-03-25 6,696 Cumshot Outdoor Blowjob Big Cock cum in mouth club outfit Surprise Cock Partying surprised
92%
My First Girly Cock
It was cold. I was running fast so that I could not get too wet by the falling rain. The streets were quiet, because everyone was inside. It was twenty minutes before midnight. I was nervous. It would be my first time I'd have sex with anyone other than a woman. I love women. I'm in love with them. ... Read full Story
shemale lover 2014-03-29 18,734 anal first time shemales
100%
Shemale Pussy
My wife Carol loves to bring she-males home for me to suck and fuck while she watches and masturbates. She works at a club that has she-male entertainers and there's nothing like having a hot she male straddling your lap so you can oil her smoothly shaven body down with baby oil. It's even better... Read full Story
shemale lover 2011-08-25 4,443 first time shemale Big Cock
0%
The orgy with a shemale
I had to move to Japan back in the fall of 2004 and lived in Tokyo in a 3 room apartment.I could not pay all of the rent so I lived with a female school teacher age 27 years of age and japanese.Her name was Miki.There was a one more girl who was friends with Miki ,I never seen much of her.Her name w... Read full Story
shemale lover 2011-08-29 5,181 Big Tits asshole Big Cock
88%
A happening in the bar
I was tired. I was tired with daily boring routine. I really needed to change something. My life had become boring and my sex life was expressionless. All women I knew proved to be untrustworthy, light-headed and superficial. I really wanted to take a break from the world. I just wanted to live my l... Read full Story
shemale lover 2011-12-05 3,491 first time big dick oral sex cum swallowing
100%
SheMale Pussy and Cock
I once had a friend who always said "never fuck anything you can't bench-press". He was right, the biggest benefit of having sex with someone smaller and lighter than you is you can lift them easily ! On a recent trip to Thailand I couldn't take my eye's off a stunning, short, tiny but ... Read full Story
shemale lover 2012-01-24 4,243 anal shemales gay male
100%
A Job in the Theatre Chapter 7
The next day Paula woke late in the day. She lay in bed feeling the glow from her bottom. It was totally erotic and the most satisfying sexual experiences she had ever had. The more she thought about it the hornier she became. She grabbed her cock immediately focused on how much smaller it was th... Read full Story
shemale lover 2012-03-13 2,688 Stockings cum oral sex
100%
Thai Ladyboy goddes in Tokyo and a cheap love hotel
This is a real account of my meeting last week with a beautiful Thai ladyboy working at a flashy show at a night club in Tokyo. Written as a not to her. Hope you like it. You sexy ladyboy goddess, I must say you have the most beautiful body. When we first started drinking wine and talking ... Read full Story
lblover77 2012-10-09 9,816 anal Ladyboy oral