Sort by
Relevancy

Free Stories

88%
Dark Temptation
Ella's body glistened with perspiration as she twirled and spun her lithe body on the dance floor, loving the way the beat of the music thumped around her. The twenty-one year old loved Brighton's laid back, hippy, music generated atmosphere and long ago had fallen into dancing until the sun came up... Read full Story
shemale lover 2012-06-22 6,275 shemale Ebony oral sex
75%
Blue collar Master, white collar slave Part 2
About an hour later I was once again naked except for my chastity pouch and my stilettos and once again I was screaming and crying, my body covered with angry red welts from Master Darren's whip. On my knees crying and begging I held his cock in my hands, trying to give the best handjob ... Read full Story
shemale lover 2012-01-13 11,905 torture extreme fiction bondage and discipline
0%
The Greatest Lie Part 19
The booked me as Alex Rios and handed me an orange jump suit and slip-on boots. I changed in a tiny curtained alcove and relinquished my clothes, shoes and purse, and became Inmate 265743. The booking clerk ignored my pleading eyes, so I begged. "You can't put me into a male population. I... Read full Story
shemale lover 2012-01-21 5,214 hardcore femdom erotic encounters
50%
Black Transsexuals Rock
Yvette Seraphim is the name. I'm a big and tall, dark-skinned and big-bottomed young Black woman of Haitian descent living in the City of Ottawa, Province of Ontario. People often say I resemble Tennis Champion Serena Williams, only taller and curvier, with more booty. I take that as a compliment. I... Read full Story
shemale lover 2012-07-17 3,873 tranny anal sex Cumshot Ebony fingering oral sex
100%
Discovering Mistress Sarah's World Part 7
Chapter 18 A Life Changing Decision Sunday morning was not much different than the day before for Josie. He woke-up on the floor outside Mistress Sarah's bedroom, dressed in a silk night-gown and his cock was hard and aroused when he awoke. Just like Saturday morning, he crawled into the bedroom.... Read full Story
shemale lover 2012-10-03 5,778 cum domination oral sex feminization
88%
Me being a pet
As you all know i am a bitch of my mistress "sissychick". This incident happen recently during my training of being a little slut. So i was sitting right next to my mistress bed, like a loyal dog, still having anal plug inside my ass and my dog collar. It was the mark of me being my mistr... Read full Story
shemale lover 2013-05-07 5,434 sex toy anal sex Shemale Fucks Guy domination cum swallowing
100%
the orgiastic fever of a trans-milf
Simulating a woman, or the orgiastic fever of a trans-milf It's been two months since I moved to the megapolis, where I've discovered several places where the third gender goes. One of my first explorations was a huge lingerie shop in a MALL; I wanted to buy some sexy stuff without being noticed ... Read full Story
hippocampus_171 2024-09-04 2,826 anal Amateur Cumshot Creampie Shemale Fucks Guy Latex Sex Toys Mature small cock
92%
My First Time
****This is not my story but i am uploading on behalf of my friend. Hope you enjoy it.**** My story is 100% true, I have been wanting to touch a big penis for a long time, im addicted to looking and watching guys play with there’s on web cam. One day I decided to search for a nice big cock on Fac... Read full Story
SachinJoy 2018-10-04 10,319 Shemale Fucks Guy Big Cock Ebony
100%
Hung Trans Lesbians Fuck Two Ladyboys
Note 1: If you like Transsexuals, Trans Lesbians, Asian Ladyboys, Big Cocks, Extreme Cock Sucking, Anal Fucking, Anal Fisting, Semen Swallowing, Role Play, Orgies, BDSM, Cock Sounding and Foot Fetish this story is for you. Note 2: All the characters are over 21. The names are fictitious, but some... Read full Story
darrell 2022-01-03 4,958 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
94%
MILF Alessia Travestita finds a bottom boy
I was several days into a cruise to New Zealand and Australia with my wife. This morning my wife went on an excursion that I had no interest in, so I had the cabin to myself. I hadn't had any sex with my wife in the last 3 days due to the activities such as the various jaunts to Auckland and the sur... Read full Story
darrell 2023-08-13 6,785 anal Cumshot Shemale Fucks Guy Fetish blonde Big Cock domination Mature deep throat cum in mouth sandals
62%
Man Is Humiliated By Escort
I am a very adventurous, open minded married guy. I am 6'2", 150lbs and I have a 5" cock. My wife (Mary) is great but she is very straight laced and doesn't like to have sex but twice a year so I decided to look elsewhere to fulfill a few fantasies. I am sure my size and stamina have a lot... Read full Story
shemale lover 2011-09-30 7,644 sucking Big Cock cum domination
100%
Debbie Part 8
Moira sat in her booth at the entrance to the subway station and saw people pass by. She sat there every day selling tickets, and although several thousand people passed her during a shift, she could now recognize many of the regulars and she even knew when to expect them. It was now almost 9 o'cloc... Read full Story
shemale lover 2011-12-23 7,789 transgender toys bondage and discipline heavy
0%
The Greatest Lie Part 13
Does Life Imitate Art? I love technology, in spite of the stereotype about girls. Although I was a guy, at least outwardly, until a year ago, I think I was always inwardly a girl. According to the stereotype, we girls are supposed to be indifferent to anything more technical than the designer cov... Read full Story
shemale lover 2012-01-20 5,246 femdom erotic encounters consensual
96%
Family Frolic
FRIDAY My sister and her husband wanted to take a few weeks off in the sun and asked me to look after their kids for a while. I'd move out of my tiny apartment and into their house for the duration. As I was still living off my severance and they had a nice spread with an indoor pool and a h... Read full Story
shemale lover 2012-01-14 31,732 strapon porn
70%
Anally destroyed by a Peruvian goddess
Browsing around the Transsexual escort ads here in town I found a new girl, something else than the typical manly faces with heavily photoshopped pictures. A Peruvian girl named Isabella had just arrived in town and was open for business. She has a few retouched pictures but also some natural selfie... Read full Story
Gracemel121 2017-08-07 14,217 Amateur Cumshot Bareback Shemale Fucks Guy Lingerie domination
93%
Chasity's white pussyboy
I led Chasity into the apartment. She was looking for a one bedroom, furnished place and had called about my ad in the newspaper. I hoped to rent this place quickly, then I would be full and could devote my time to some maintenance and repairs rather than showing places. I looked at the renta... Read full Story
blakepalmer 2020-06-08 16,378 Cumshot Bareback Blowjob Big Cock Ebony domination Interracial black shemale cum in mouth
60%
Filthy Little Beast Part 2
Chapter 8 The first thing that struck me was pink! More pink satin than I thought existed in the entire world. The walls were covered in baby pink satin curtains, the plush carpet was also baby pink. Like all the other rooms in this house of the bizarre the ceiling as a full mirror. There was a h... Read full Story
shemale lover 2011-12-02 7,784 taboo Fetish crossdressing erotic encounters
100%
Guard Duty
Susan Denton was apprehensive as she approached the airport security station. She didn't like having to set her purse on the black conveyor belt that transported it - and the personal effects it contained - through the X-ray machine that rendered ghost images of her personal effects. On one occasion... Read full Story
shemale lover 2011-12-09 3,910 hardcore chick with dick domination
87%
Finishing School for Shemales
Mistress K looked at the school report and smiled. She wouldn't describe herself as an evil bitch, but plenty had. She was proud of her position. Headmistress of the Finishing School for TGirls. So many beautiful shemale girls had left her careful administration and gone on to happy lives, or ... Read full Story
shemale lover 2012-08-09 10,962 shemales Cumshot domination oral sex
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 27,948 tranny Cumshot suck Shemale Fucks Guy ass fucking wanking
94%
My Night with Luisa Tavares
I flew to Curitiba just to be with Luisa Tavares. She greeted me at the door to her apartment in a bathrobe. She had just taken a shower and invited me to do the same. When I returned from the shower, I found her sitting on the bed completely naked. She is so beautiful, such gorgeous breasts and... Read full Story
hotspur 2019-09-23 12,108 Shemale Fucks Guy domination shemale fucks male big shemale cock Luisa Tavares
92%
My story
"You're gonna make me suck that, aren't you?", I asked her. " Yes" she said. "But you're going to suck it because you want to". " I doubt that", I said. "We'll see", she said with a smile. "You're gonna cum in my mouth, aren't you?", I asked? "Yes baby, Mommy is gonna feed you her sweet nectar... Read full Story
Curious_billy 2022-12-01 7,636 Teen (18+) Cumshot Bareback Shemale Fucks Guy Big Cock domination Homemade cum in mouth
100%
Why I desire transsexual cock
I've thought about what it must feel like to have jus for a bit, a transsexual cock inside you. How ones nervousness is turned into extreme horniness upon seeing her cock for the first time. The thoughts that must race thru your head. How big is her she-cock?. Do I touch it? Do i lick the length of... Read full Story
Curious_billy 2023-01-19 7,687 Amateur Cumshot Bareback Creampie Shemale Fucks Guy Blowjob blonde Big Cock domination Homemade cum in mouth
100%
My story
Please don't hurt me, I whimpered softly. Oh no my Lil slut, mommy has no intention of hurting you but making your fantasy become real, she said. But your thing, its kinda big. I'm a bit scared, I said. Mmmmmm, don't worry baby. Mommy wants this to be so good that you become my steady, she said... Read full Story
Curious_billy 2024-02-03 7,067 anal Amateur Big Tits Bareback Creampie Shemale Fucks Guy Blowjob Big Cock domination Mature Homemade cum in mouth
75%
All Night Forced Sex Part 2
When I woke up I was in a darkened room and a woman was standing in front of me she was the most stunningly beautiful woman I'd ever seen before in my life. She's statuesque, about 30ish, with long red hair almost down to her perfectly shaped ass. She's wearing all black - a vest that pushes her bea... Read full Story
shemale lover 2011-10-09 3,697 shemale domination spanking
81%
Husband and wife used by Mr. Big Black Cock
We had decided to take a trip to Vegas and spend some alone time together.. We started off with dinner, then went to hit the tables.. My husband was on a winning streak. He was up at least $1500. I whispered into his ear have fun I'll be in that cute little shop. ok? Then his luck ran out.. and befo... Read full Story
shemale lover 2011-12-18 8,301 shemales gay male interracial sex
100%
Learning
Charlie had always been a curious kid growing up. So naturally when he got his very own computer, he was bound to explore. As Charlie turned 18 and was a senior in high school, he finally found something that really excited him. He saw a woman using a strapon on a man, who seemed to love it. Charlie... Read full Story
shemale lover 2012-01-15 3,816 gay male Sex Toys shemale porn
50%
Baby Face Jack's Biggest Fight
The referee held his gloved hand high in the air. The crowd was hushed as the ring announcer spoke, "Ladies and Gentlemen, the winner of this World Featherweight Championship Boxing Match to unify the title, by technical knockout, and still undefeated; Baby-face Jack Mc Coy." The crowd scr... Read full Story
shemale lover 2012-02-08 7,604 fuck oral
100%
Date Sex!
I wake up, my head throbbing. "Ugh, what a nightmare." I think to myself as I try to shake the sleep and cobwebs from my mind. My head splitting with a headache, it starts to register that something doesn't feel right. "It was just a dream Mar..." I tell myself as I t... Read full Story
shemale lover 2012-07-24 4,773 shemale domination oral sex
100%
Chrissie Learns A Harsh Lesson Part 1
This is a story I've been wanting to write for a while but I only recently got the gentleman involved to tell me it would be okay to write about our encounter. Normally it wouldn't bother me to write about any experience I've had but this gentleman is a special friend and I didn't feel right about... Read full Story
shemale lover 2012-08-21 3,010 oral domination deepthroating
94%
Tortured by the T-Girl Tutor
Duncan didn't quite know how to handle it. He'd planned on a quiet Winter Break. Sleeping til noon, watching too much television and eating tons of junk food. That kind of stuff. He had a whole two weeks off from community college. At school, he was an outcast. They say life gets better after hi... Read full Story
shemale lover 2012-12-18 34,607 Big Tits shemale Big Cock Lingerie domination
96%
The Backdoor
It was only my first time in the club and my hands were shaking beyond control. I almost didn't make it through the front door I was so nervous. I felt so out of place. Everywhere I looked, it felt like people were staring at me, judging me. It was like they knew I had no clue what I was doing. ... Read full Story
shemale lover 2013-01-03 17,133 sucking Shemale Fucks Guy Blowjob Big Cock Interracial
90%
The Perfect Choice
Andrew had moved in with Hannah a few short months ago and so far everything was going just the way she wanted. She was an endless tease; wearing short skirts and dresses when they were out during the day or tiny shorts and vest tops when they were at home together. She did everything she could to t... Read full Story
shemale lover 2013-01-10 6,943 hardcore Shemale Fucks Guy Blowjob ass fucking domination
81%
Ladyboy Switch Story
I am messed up with how I feel about this. I still love looking at women. I love tits and arse. I like the soft feel of women – kissing them and feeling their bodies. I don’t look at men in public and get turned on – men with clothes on do nothing for me. Put me somewhere that I can see those same m... Read full Story
shemale lover 2015-02-27 7,552 Cumshot suck Shemale Fucks Guy Ladyboy ass fucking swallowing
89%
Third times the charm!
After my first 2 times with a ts it basically just became an urge that I had to have a need I had to satisfy! Just like regular sex the more I thought about it the more I wanted it. I finally asked Liz if she knew anymore from around where we were. Luckily for me she did and set me up with her frie... Read full Story
Duke04 2017-04-04 9,048 big dick hardcore suck ass fucking kiss Shemale on Guy
100%
How could I forget my first time .......
"Ok, ok, ok stop. No more. It hurts a bit" I said. "Just relax your ass baby. Push out like you have to go poo", my date said. How did I end up like this? A straight A college student, a devout Christian with a nice gf like me ends up in bed with this sexy woman ...... Ok wait, I thought she wa... Read full Story
Curious_billy 2023-10-29 9,807 anal Amateur Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Big Cock domination Homemade cum in mouth teen (18+)
50%
Transvestite father异装癖的父亲和儿子被农民工虐待
'migrant worker S, good at foul language and humiliation, SP, heavy hands, is it acceptable?' On the SM dating software, a message popped up. Migrant worker S. What the hell? I casually click on his information, 39Get 186 and 76, dynamic is full of handsome muscles, muddy shoes, a glimpse of gar... Read full Story
Oldslut Sissy 2024-08-21 2,374 Amateur Big Cock Asian Sex Toys Mature sissy chinese
33%
Being Barbi's Bitch
After ten wasted years of foolishly trusting in love to 'cure' me of my femininity, I had only just begun to re-embrace the sissy inside me when something made me reach out to an old friend. What made me do it, I really don't know. Although I was once again revelling in even the smallest aspects of ... Read full Story
shemale lover 2011-10-01 9,431 Stockings sucking domination
100%
The Terrace View Apartments Part 7
My new life had settled into a wonderful routine. I would wake very early in the morning, usually still wrapped securely in Mistress Kendra’s arms. I would spend an hour or so working on my figure maintenance exercises, enjoy a cleansing enema, a refreshing bath and body shave, then I would la... Read full Story
shemale lover 2011-11-19 4,348 Creampie Blowjob domination
60%
Aunt Cindy's Bizarre World
My name was Jim Rogers Jr. at one time. I was born and raised in a small town in a rural county in Oklahoma. My father James had been the pastor of the local Pentecostal Assembly of Jesus. Dad was what was known an ultra conservative hell fire and brimstone preacher. My mother's name was Allison. Sh... Read full Story
shemale lover 2011-12-02 10,612 taboo Fetish crossdressing sentimental erotic
85%
TV Cum Slut
As we sit on the couch watching Shemale porn, my friend Bob turns and asks. "Do you still wanna be my buttslut?" "Yeah, Hell Yeah! We've been talking about it for a long time." He smiles "Did you bring some stuff to get dressed up? You keep talking about it, and I'... Read full Story
shemale lover 2012-01-27 5,110 sucking cum domination crossdressing
100%
THE WONDERFUL ADVENTURES OF MISS K: QUEEN OF THE ROAD
Miss K drove the car through the Midwestern countryside, enjoying the early spring breeze that leaked through the SUV's window as it blew through her platinum blonde hair. Her tits were held up by the tight, white, midriff-baring top she wore that stopped just below the lower curve of her tits... Read full Story
shemale lover 2012-01-28 4,380 licking sucking fucking Sex Toys
40%
First Sexual Crossdress Experience
How my secretary found out I'm a bi TV and how me and my TV friend educate her into some of the more zany aspects of TV sex. *** As I laid back against the wall of the toilet with my nylon-clad thighs spread wide and my erect cock jutting up lewdly from between them, the wooden door in front o... Read full Story
shemale lover 2012-09-27 6,080 first time Fetish cum oral crossdressing nylon
100%
Discovering Mistress Sarah's World Part 4
Chapter 11 Discovering the Girl in Him For the first time since he arrived at Mistress Sarah's house, Josie was left alone in silence. His cock was still throbbing from all the attention from the girls. It continued to throb as he thought about his exciting assignments for the night. He picked up... Read full Story
shemale lover 2012-10-03 4,738 domination Sex Toys feminization
100%
Anastasia's Life So Far
Chapter 1: Humbling Beginnings My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barbi... Read full Story
shemale lover 2012-11-27 11,493 Fetish crossdressing feminization
45%
Shemale Prostate Orgasmic Bliss!!!!
if she wanted breasts." "Oh no. That's the amazing part. The more I dressed him the more feminine he became. By now I'd moved him her and her clothes into the other bedroom. She wasn't happy with that but we came to an agreement; I'd milk her once a week and she... Read full Story
ProstateMilker 2015-05-01 14,439 Masturbation cum orgasm cumshots prostate
97%
FEM FIRM 4-POP SECRET
Fem Firm 4: Pop Secret by: B-Man View Story Details Rating: XXXAdd Review Added: 11/20/2016 Complete:no Synopsis: Ruby learns a family secret which will change her life forever. Categories:Bimbo Workplace Situations Keywords:Long Finger Na... Read full Story
bennyx709 2016-11-22 10,496 anal sex cocksucking workplace situations
100%
A Boy and Laura
Jonas was in a hotel enjoying the last days of his vacation in Cabo Frio, Rio de Janeiro. Sitting at the bar drinking an orange juice and watching the landscape, he saw a woman approaching, wearing a purple bikini that made up her breasts well, but kept her waist covered by a flowered thong that als... Read full Story
haroldãosanguebom 2021-08-17 7,836 Shemale Fucks Guy Blowjob domination Mature
100%
MILF Alessia Travestita finds a bottom boy pt 2
Several days ago, Alessia a beautiful Transsexual with a huge cock seduced Stan on their cruise ship. He willingly and enthusiastically sucked her cock and gave her his ass. She brutally throat fucked his mouth before pounding his ass. They spent over two hours together until they were interrupted b... Read full Story
darrell 2023-08-13 6,763 anal Shemale Fucks Guy Fetish Blowjob blonde Big Cock domination Mature deep throat cum in mouth sandals toe sucking
100%
Being taught a lesson .......... I think!
How did I end up on my back in my own bed, legs straight up with my ankles over her shoulders, ready to have my ass fucked from a lost bet? A bet that Alma clearly cheated at as we discover. I was off to Thailand for a 16 week course in Thai massage at a school recommended highly by a friend I ha... Read full Story
Curious_billy 2023-11-12 9,104 anal Amateur Group Sex Bareback Creampie Shemale Fucks Guy threesome Big Cock domination Homemade Vintage cum in mouth
80%
Adult Porn Shops
Around my senior year in high school I became more enamored with sex as all teenagers do. I loved lesbian sex and was addicted to shemale's as well. Nothing turned me on about gay sex. I was only curious about being with a shemale. So being underage the only porn you can get is via internet or throu... Read full Story
shemale lover 2011-10-09 5,412 domination gay porn booth
100%
The Conference Part 2
I was in an excited mood all day after the previous evenings surprise and events, and was anticipating another evening of fun. At last the time to meet in the bar came and I arrived to find Cleo in there with girl. I went over and said "Hi" and sat down. She introduced me to her friend ... Read full Story
shemale lover 2011-12-24 4,225 Fetish crossdressing erotic encounters
87%
Beaches
A couple of things you should know about me: I'm not gay; I've always had this thing for dark-skinned women. I graduated from the army at age 21 and headed home to the Bronx. Me and a buddy of mine started up a livery car service. We started with four cars. 15 years later, we had 100 cars and alm... Read full Story
shemale lover 2012-01-03 5,346 Fetish shemale Ebony
33%
A Certain Perception
Kyra was not the girl of my dreams. I never DARED dream a woman that good would just walk into my life. She was smart, sassy, vivacious, intuitive, resourceful, and a real 'people person'. We met in an Internet chat room called "Working Girls". We're not talking about the kind you find in ... Read full Story
shemale lover 2012-02-23 8,763 Fetish transformation dildo
100%
Bar trap Part 2
I was supposed to put on heavy makeup. Starting with the foundation, I applied a generous layer of a brand especially designed for the use on stage, that did a very good job covering up any dark shadows. After I was satisfied with the effect, I used a brush to put on powder and make it all smoot... Read full Story
shemale lover 2012-02-26 3,565 Fetish crossdressing whore
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 4,246 dildo oral transvestite sissy