Sort by
Relevancy

Free Stories

100%
My TV Sex Adventures Hot time in the Gurl&#
After sucking off the custodian of the offices next door I went back to the club. I was seriously disappointed. I loved how big and hard his dick was and I really wanted a serious cock like his to fuck. I got back into the club with only a knowing grin and a chuckle from the guy at the door. He was... Read full Story
shemale lover 2012-07-05 4,068 Group Sex Cumshot sucking Interracial
100%
Bookstore Bound
My Master, ever the gentleman, held the car door open for me. I smiled at him as I turned to get out of the car. I made sure to spread my legs in a very unladylike manner, giving him a good peek up my short dress. He simply shook his head and took my arm. We made our way over to the entrance to the ... Read full Story
shemale lover 2012-08-02 5,532 cum oral sex cum swallowing face fucking
80%
Brazilian Discovery Chapter 4
John, the husband of Susan (see Susan and John series) has travelled to Brazil for a one year training session. Mr Gupta has sent him as the pretty little Joan, in the hope he would lose any interest for Susan and leave him totally free to deal with his senior accountant! The corset maker had bee... Read full Story
shemale lover 2012-08-25 4,305 cum oral huge cock brazilian
100%
Brazilian Heat
At twenty-six I did something I had been trying to do since I was eighteen. I finally took the vacation I wanted. Ever since my freshman year of college I had been trying to get to Brazil for spring break. Spring Breaks came and went and never once did I make it to Brazil. All I knew was that I was ... Read full Story
shemale lover 2012-08-26 7,053 anal sex Big Tits Blowjob ass licking
100%
Voodoo
I was walking though a neighborhood, looking for a house to brake into, I came up on to this house it was small, I think about a three bed roomed house, I walked up the path, then I walk around it to find a open window or door and I found an open window leading into the cellar. Yeah, I am Alex Ha... Read full Story
shemale lover 2012-09-09 4,096 Cumshot Blowjob Big Cock Ebony domination
50%
Al Fresco: An Erotic Sci Fi Tale
"Thank goodness for modern science," Ali said as she smoothed her tight black skirt across her shapely hips. The tall brunette turned this way and that in front of her mirror, admiring her taut, toned, and trim figure. Her hands moved up from her hips to cup the twin handfuls at her chest,... Read full Story
shemale lover 2012-09-19 7,354 Cumshot ass fucking oral sex cum swallowing
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 5,810 first time Fetish cum oral crossdressing nylon
100%
Alexis Chapter 4
Thursday rolls around, and Mr. Hughes tells me to stay after class. As usual, he walks into the supply closet when all of the students have left, and I diligently follow him. I suck his cock for a little bit, and then he says that he wants to fuck me. I nod my head and stand up, looking him in the e... Read full Story
shemale lover 2012-10-06 3,807 Creampie ass fucking oral sex
57%
Futa's Are Real
I am writing this letter as my account of truth in the legend of Futa girls. Now I should write a little about me first. I am 26 now but when it started I was twenty-two. A college jock and loved women. I would go to all the parties and college bars and hang outs. I was good looking guy 6'3, 276lbs.... Read full Story
shemale lover 2012-12-14 5,552 Big Tits Cumshot sucking jerking
50%
Gangbang: Daddy's Girl
"Oh yeah...that's daddy's girl," my dad moaned as he massaged my enormous round sticky ass. I'm 18 and my sister was about 5 years older than me, so who knew how long this had been going on for, I thought to myself. At least I tried to think as I slowly closed my eyes and bit my bottom ... Read full Story
shemale lover 2012-12-16 9,565 sucking cum gangbang
93%
I Am My Wife's Best Girlfriend
I was standing in our bedroom, my wife was on her way out the door. I was holding her slip up against my naked body. It felt very sensual. I pictured myself, for just a moment, as a real woman, with large breasts, big blonde hair, and smooth, hairless skin. I rubbed the fabric against me, sighing. S... Read full Story
shemale lover 2013-01-18 7,365 Crossdresser Cumshot Creampie Blowjob ass fucking
84%
Lesser of Two Evils
My name is Eric. At 21, I was working as the IT guy at a prominent Caribbean cruise company. My days were usually pretty boring. Fixing computer problems were usually a no brainer for me. People are so stupid when it comes to how they use their machines that I assume there will always be a need for ... Read full Story
shemale lover 2013-03-27 23,035 hardcore Cumshot sucking ass fucking Guy Fucks Shemale
76%
She didn't see it coming
I had seen her at a stop light while driving around looking for a spot to eat. She drove a red Pontiac Sunfire, the convertible kind that no self-respecting man would be caught dead in. She was gorgeous, at least from what I saw from my elevated platform of the SUV I was driving. She was petite, ... Read full Story
shemale lover 2013-07-17 5,287 hardcore oral sex big boobs kissing shemale sex
97%
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 2013-07-22 10,529 transsexual oral sex ass fingering kissing
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 9,317 Cumshot suck ass fucking oral sex Guy Fucks Shemale
93%
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 2015-02-27 5,836 tranny Cumshot Shemale Fucks Guy ass fucking Guy Fucks Shemale
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 7,574 Big Cock ass licking redhead rimming Shemale on Guy
96%
My First Sex with Tgirl
This is story about me......Hope you all enjoy it I was 19 years old and itching to have sex like every normal teenager. Years of jerking off to porn had only expanded my imagination and made me want to fuck a girl even more. I was turned on by just about anything and everything except gay porn. Ev... Read full Story
sach 2016-02-16 13,740 first time tranny ass fucking guy on shemale mutual suck
80%
The Farm
“See you Sunday, baby,” said Marcus Jenkins to his wife, Tasha. “Alright! Have a good day at work,” the wireless phone company retail store manager smiled. “Love you, Kobe! Love you, Tiara,” the wastewater plant operator said to his offspring. “Love you, too, daddy,” the youngsters rang out in un... Read full Story
Faggyboi and Puzziboi 2021-12-08 5,863 Teen (18+) gangbang Guy Fucks Shemale sissy femboy Ass to Mouth
100%
Meeting Amanda
I’m a happily married man. My wife Tess and I have been together since we were teenagers. We were each other’s first real lovers and being in our mid-thirties by now, we still madly in love with each other. Tess and I always are very honest and open to each other. Both in normal life and sexual... Read full Story
rforasht 2022-07-20 7,776 Big Tits Cumshot Shemale Fucks Guy threesome blonde Big Cock Lingerie Shemale and Girl redhead Homemade Shemale fucks couple
100%
I was a Top before this experience
She was tall, 6 feet probably, a white colombian beauty, green eyes. Pretty gym body, strong but feminine, don't know how that works, but this was a work of art. Sweet but commanding voice, you know, similar to that voice that tells you that it's recalculating your GPS route or to turn left right no... Read full Story
Mizty 2022-11-03 6,778 Amateur Cumshot Shemale Fucks Guy Blowjob Big Cock Homemade
94%
New Girl in Town
Margo sat next to me in the coffee shop late that Saturday afternoon. His real name was Mark, but he was one of the loveliest Drag Queens in New York City. I had been dressing secretly at home in my mother’s and sister’s clothes for just over three years, but at 18 years old, I had never... Read full Story
shemale lover 2019-06-04 10,239 anal shemale oral sex
100%
Who actually likes English class?
I was sitting in yet another boring as hell English class. Seriously, why do I need to read Chaucer? Is that necessary for anything I will do in my life? As much as I try to convince myself the answer to those questions are yes, I still can't get interested in what he talked about in 1400 a.d. Ho... Read full Story
shemale lover 2011-08-12 7,726 Cumshot deepthroating cum swallowing
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 4,621 first time shemale Big Cock
70%
Shemale Gangbang
I am not your average female. But I guess I am not your average male either. You see, I am a tranny. I make a really hot woman. I am 5'10", am slim and have dark, wavy hair that comes down to tight between my shoulder blades. The only thing I was missing was beautiful tits. So I got those as we... Read full Story
shemale lover 2011-08-27 17,690 anal Blowjob cum swallowing
84%
Page Sixty-Nine
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... Read full Story
shemale lover 2011-10-20 6,211 cum oral deep throat fucking
75%
A Dickgirl
With a start Ginny woke up. Sunlight gleamed through the windows and her alarm clock blared. Wiping sleep from her eyes, Ginny kicked off the covers and rolled out of bed. "Damn," she thought. "Its Monday." She stumbled into the bathroom and surveyed here naked body in the mir... Read full Story
shemale lover 2011-10-28 5,924 big dick cum oral
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 4,906 sucking cum fingering
100%
Amy The Tranny Part 1
I met Amy at an adult theatre in town. She was dressed to nines in a mini skirt, tight halter top, and pumps leading up a pair of fishnet clad legs. I invited her into a private booth and once inside, went over her price for some adult fun. She told me I couldn't fuck her as she was on her per... Read full Story
shemale lover 2011-12-14 4,965 shemales hardcore anal sex Big Cock
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 7,536 Creampie ass fucking mouth fuck
87%
They Were Right
They were my friends, but I'd had sex with both of them. Not at the same time, but I had dated the one for a month and just started dating the other. So, although the thought had never crossed my mind before, I found myself dressed up as a girl for Halloween. After we had partied at a few clubs and ... Read full Story
shemale lover 2011-12-29 6,030 shemale Big Cock porn
100%
Becoming A She-Males Bitch Part 2
After last nights ordeal I was given something to drink and taken to a bedroom upstairs. What I drank must have had some kind of drug in it because I was knocked out. I bet I was asleep in just a couple of minutes. I barely even remember lying down. When I woke up I was naked, sore as hell and fe... Read full Story
shemale lover 2012-01-04 9,045 cum oral domination
100%
And Life Goes On Part 2
So here I sit in my sexy black Miniskirt. The red silk blouse I am wearing shows off my ample sized breasts. Underneath I am wearing a red Satin corset which reduces my waist to a waspy 26 inches. I have on a pair of black satin panties with a matching black lacy bra. The red nylons I am wearing acc... Read full Story
shemale lover 2012-01-10 4,134 Big Tits Fetish feminization
100%
A Change Of Luck Part 2
I froze when I heard the voice, because I knew who it belonged to. "Well, well, well...what have we here? I never thought I would get to see this - my roommate sucking off a girls cock!" I turned around, Lena's cum still splattered on my face, and looked at Gina. I was plastered with... Read full Story
shemale lover 2012-02-18 3,811 cum oral long cock
100%
Ellen's Candy
Sometimes I get in the mood to suck a dick but I’ve never considered myself gay. I’m @ the very least bisexual but I don’t like to limit myself to that either because I think it restricts my sexuality. I get turned on watching all types of sexual situations that you could think of;... Read full Story
shemale lover 2012-04-02 5,445 Cumshot condom sex
90%
Roxy
I’ve been the president of my goys school PTA for the last two years and really enjoy doing it, so when the national conference came around, I went with my husband’s blessings. It was a four day conference in Atlanta, Georgia and as I had no one to room with, I was assigned a roommate. I... Read full Story
shemale lover 2012-04-10 5,072 Big Cock orgasm fingering oral sex
100%
Being Curious Has Big Rewards
I was brought up believing that men were not supposed to have sex together. The thought of this taboo type of sex was always made me curious. When I was 18 or 19, I visited an adult book store, just because I was horny and wanted to get a magazine that showed people getting fucked so I would have... Read full Story
shemale lover 2012-04-26 5,929 first time Cumshot oral sex cum swallowing
100%
Bend That Gender
Shannon's Shocking Discovery Shannon leaned against Marilyn. She was definitely light-headed from her last drink. Marilyn's hand resting on her left hip pulled her closer, a move at once comforting and unsettling. She slid her arm around her new friend's waist, resting her head on the silk covere... Read full Story
shemale lover 2012-04-27 7,138 orgasm oral sex cum swallowing
100%
Porshe's Escapade Chapter 5
I'm walking through the crowded hotel lobby looking like a slutty school girl hooker, everyone's eyes are on me, and I'm being led by Jeff who is slightly in front of me holding my hand. We head to the elevator and step in just the two of us. I'm a little relieved yet now I start to get nervous of w... Read full Story
shemale lover 2012-09-06 2,796 Cumshot Masturbation Blowjob Big Cock fingering
100%
Brian and Bree, and Mitch Chapter 2
"What ever I want?" Mitch looked deep into Bree's eyes, she sheepishly nods up at him, "I've always wanted to please a man, I'm just glad it could also be my best friend." She replied, her voice trembling with nervous excitement, "Just give me ten minutes, and meet me in ... Read full Story
shemale lover 2012-09-20 3,555 anal cum fingering oral sex
60%
Brotherly Love, Sisterly Love Chapter 2
"RACHEL" My twin sister, and sometime brother, and I had been experimenting sexually with each other and crossdressing together for around a month, growing to love and to perfect our new feminine personas until they became the ones we thought of as our true selves. Whenever our parents ... Read full Story
shemale lover 2012-09-28 6,776 Cumshot Fetish oral sex cum swallowing
66%
Discovering Mistress Sarah's World Part 2
Chapter 4 : Introducing Miss May! Miss May's arrival seemed sudden and quick to Joe. He heard the door close downstairs. Then there was the sound of somebody running up the steps. The bedroom door flung open and before Joe could look up to see anything, he heard an excited voice exclaim, "ki... Read full Story
shemale lover 2012-10-03 5,915 cum domination Sex Toys sissy
100%
Working for a Living Chapter 4
The buzzing of her cellphone on vibrate was barely noticeable over the hum of the vibrator between her thighs. Normally Jamie would have just ignored it but Chris had told her he might call if his meeting finished early. Her hand felt for the phone on the nightstand beside the bed. She looked at the... Read full Story
shemale lover 2012-10-05 3,009 anal shemale oral cum swallowing
100%
Francis Meets a Black Stud Part 5
I finally came upon a plan that I thought would make everyone happy. I would keep on playing this game with my man. I figured that as long as I was dressed like a girl, it didn't matter who he showed those videos too. I mean no one would know it was me and after all, he would be finish his vacation ... Read full Story
shemale lover 2012-11-20 3,052 cum oral sex Interracial
100%
Fucking and Getting Ass Fucked
Playing with Lisa. I have been seeing Lisa for a few years. We have what I call a "Role Play" game that we both love to do when we meet. It almost always starts the same. But it does have a different ending most of the time. It was early March and the weather was cold. I was driving ... Read full Story
shemale lover 2012-12-04 4,739 tranny fingering oral sex
100%
When Curiosity Fills
I sat in alone in my office at 11:00 p.m. on a Thursday night in April, preparing an important motion in a multi-million dollar malpractice suit. After editing the final draft I sat back and took a deep breath. I was exhausted, and, oddly enough, pretty horny. The wife was out of town and somehow I ... Read full Story
shemale lover 2012-12-08 8,815 anal shemales cum
100%
Jesse's Dream Job - The First Day
Jesse didn't want to be late on his first day so he got to the office about 20 minutes early. He was looking sharp in a black suit pinstriped in light blue. The shirt matched the pinstripes and the tie was made up of reds, purples and a little of the light blue to bring it all together. Jesse had ne... Read full Story
shemale lover 2012-12-20 9,753 hardcore Cumshot Shemale Fucks Guy ass fucking handjob
100%
Male or Shemale, Still a Slut
Part 1 My name is Brandon. I'm 18 (still in high school), 5'5", white with black hair, and rather feminine. I'm really slim with barely any body hair. All this has combined so that I'm not so popular with the ladies, which sucks cause I am one horny son of a bitch. Luckily, I'm rather fond ... Read full Story
shemale lover 2012-12-20 9,555 Cumshot sucking blonde ass fucking Guy Fucks Shemale
94%
Pre-Op Roommate
I was a few months away from graduating college with my Theater Arts degree when Mark, my roommate, told me he was going in for the sex change operation. We popped a couple of beers and talked about this thing… he wasn’t sure whether he liked guys or not, he’d never done anyth... Read full Story
shemale lover 2012-12-22 6,733 Crossdresser sucking ass fucking handjob
93%
The Tranny Trucker
A gust of freezing wind blasted across my face. I succumbed to worries of frostbite as I walked aimlessly along the side of the highway.\r\n\r\nThe wind of passing trucks nearly knocked me off my feet. This must have been dangerous. It\'s something I should have considered.\r\n\r\nMy parents separat... Read full Story
shemale lover 2013-07-19 7,111 Cumshot ass fucking ass licking oral sex kissing
83%
MY FIRST TIME WITH A SHEMALE - 2
DEAR READERS I DON’T KNOW IF YOU LIKED MY FIRST STORY AS THERE WERE NO COMMENTS ........ !!! After we finished our late dinner in the very cosy position she whispered “wanna have some wine honey?” I replied “I’d love to”. She got up leaving me sitting on her bed and poured two large glass-full of... Read full Story
Lisawantsu7 2014-09-02 6,789 hardcore Creampie Big Cock ass fucking Shemale and Girl
93%
Interracial Sissy Story
(Some prior notes about me, this story and my writings: If MALE bisexuality, crossdressing or interracial sex bother you, don't even bother reading this further, much less commenting. Many have had secret fantasies about what it would be like to be the opposite sex, during sex. Some of my influences... Read full Story
shemale lover 2015-05-01 15,551 first time ass Cumshot suck cd sissy make up
66%
Trannies in Space
There was no spaceport on Jansen's Planet. There had been, but whatever calamity had befallen the world generations ago had also destroyed its port. It was one of so many planets out in the Barrens that had fallen on hard times. So Dekker set down the Barnabas in a clearing in the forest, a remna... Read full Story
ASSEaster5678 2019-01-25 12,446 Shemale Fucks Guy Guy Fucks Shemale Sex Toys space robots
80%
Transsexual Savage
John had walked for eleven days. He was headed towards Fort Winston at the Hiat River, and he still had about three days ahead of him. The Hiat River was the natural border that separated the civilized world, where he came from, and the savage and brutal wilderness, where the natives lived and pract... Read full Story
Anal Orgasm 2020-07-10 6,485 Big Tits Outdoor Masturbation Bareback Creampie Shemale Fucks Guy Blowjob Guy Fucks Shemale
100%
My Fantasy Story
My first time, Sissy Cuckold for BBC After ten years of marriage, my wife and I wanted more. First we went to some strip clubs together. One night one of the girls my wife liked told us about a swingers club. So we gave it a try. Best decision we'd ever made. We went, at first just wallflowers, ... Read full Story
Mikky666 2020-10-09 10,217 blonde Big Cock Interracial Ass to Mouth
100%
Jennifer
WhiskeyIsGood I woke with a start, startled by a loud banging sound from downstairs. The floor shook from the vibrations, causing me to sit upright in my bed and glance towards my bedroom door. What in the hell, was going on down there? My question was quickly answered, by another loud bang, foll... Read full Story
Gwapo67 2022-09-13 6,302 Big Tits Bareback Shemale Fucks Guy Blowjob blonde Big Cock