Sort by
Relevancy

Free Stories

100%
His Perfect Shemale Partner Part 1
I am in senior year of school and anyone who has been to school at 18 will know it is not a pleasant time to be working when your friends are all out drinking and enjoying themselves but I needed to go back to school to go the university I wanted to go to. I am a tall fairly muscular straight guy wh... Read full Story
shemale lover 2011-08-28 5,292 anal Cumshot sucking
100%
My Surprise
Here I was in another strange town; the hotel was as usual just one of Those places you sleep in and I was bored and fed up with travelling A drink I thought I need something to relieve the boredom. An hour later I was in a bar in now what was the name of this town ?, Drinking alone in the corn... Read full Story
shemale lover 2011-08-31 5,673 Small Tits sucking pussy
100%
Adventures of Shemale Sandra Part 1
His name was Phillip. Or at least it had been. Honestly, he wasn't sure who he was; all he knew was that what he had done two years ago was what he thought was right. This was the lifestyle he wanted. It should be said that Phillip has always had strong female influences throughout his life. He a... Read full Story
shemale lover 2011-09-02 3,822 anal sex asshole cum
87%
My first time
I was nervous, and had never even gotten laid before. I had jacked off a lot, but I thought about real women when I shot my load. But Dani sure looked and seemed like a real woman, and she had brought me back to her place. When she started kissing me, I didn't even have to think about it - I slipped... Read full Story
shemale lover 2011-10-30 3,704 anal first time oral extreme
100%
The Client
Meeting the client and selling your firm's abilities to the client's firm is about the toughest part of the business of being in the contract evidence collection business. Invariably you want a lot more for the work than the client thinks it's worth. This is partly a function of time estimates, or m... Read full Story
shemale lover 2011-11-13 4,300 anal sex asshole shemale
83%
Jesse’s Dream Job
****This a fantasy scenario i have dreamed of ever after i became interested in beautiful Ts women. Even though this is my fantasy alot of credit goes to author Ruwild (which some of u may have read his stories) who was nice enough to write the story for me. Enjoy!!!***** Jesse's Dream Job ... Read full Story
AlcatrazNYC 2011-11-19 8,045 Shemale Fucks Guy cum swallowing
57%
Debbie Part 9
It soon turned out that Debbie wasn't destined to spend the rest of her life as a whore. As she returned to the apartment one night one of Mistress' men was waiting for her. She had only just opened the door, when without a word he cuffed her hands behind her back, gagged her and put a collar and le... Read full Story
shemale lover 2011-12-23 6,492 transgender toys bondage and discipline heavy
94%
She was a he
I was recently divorced, 39 years of age and living in an apartment in Sydney's inner eastern suburbs not far from the famous red light district of Kings Cross. After two failed marriages, I was footloose and fiance free and as lusty as a rampant bull on speed. I chased after anything wearin... Read full Story
shemale lover 2012-01-24 7,021 Cumshot Guy Fucks Shemale Frottage
50%
Devastating and dominating
Tracy drove the black SUV with her friend Miss K in the passenger side, both of them struggling not to be bored to sleep with the monotonous countryside I-64, the scenery broken up only by the occasional road sign or truck stop. The Madonna CD thumping in the stereo helped matters though, the t... Read full Story
shemale lover 2012-01-29 5,189 Masturbation sucking Creampie Latex fucking
100%
Silk Scarf
Michael sat at the table playing with his drink. He’d gotten his first real paycheck today and decided he deserved a dinner in the best restaurant he could afford. Of course which what they were paying entry level trainees at Donaldson & Rhobes, his choices quickly narrowed to a few. So he... Read full Story
shemale lover 2012-02-05 4,593 ass fucking oral sex Guy Fucks Shemale
100%
The Triple X cocktail - Wife Shares Shemale With H
"Where are you?" Tara asked in a high pitched voice as if she was either excited or freaked out. "I'm at the boutique" I replied. "Ok I am coming by, something very important. I am so freaked out now and I will tell you all about it when I meet you. Will be there in half an ... Read full Story
shemale lover 2012-02-21 3,762 Group Sex Creampie face fucking tit licking
100%
I've always wanted to meet a gurl!
First of all I would like to apologize for my English. Hello there! I live in a small country's biggest city and here people are strange. If they are crossdressers, shemales, trannies, tgirls, gurls (actually we have only 2 words for a shemale, so I don't know which one is NOT offending please excu... Read full Story
shemale lover 2012-03-30 2,619 Small Tits anal sex oral sex cum swallowing
91%
A New Year's Resolution
I'm not gay (laughing), with that said, I have seen some very good looking, uh, guys. Okay, go ahead and laugh. You see, toward the end of this past summer (August 2011), my wife and I visited an old friend of mine in Pattaya, Chon Buri, Thailand. He's a former Navy Seal. I'm a former Army Ranger as... Read full Story
shemale lover 2012-04-16 7,752 anal sex cum oral sex
100%
My Philippine Girl
My name is Angel Smith I am a 23 year old guy with a nice toned fit body, and about a 8 inch dick and for 2 or 3 years I have been fantasying about having sex with a Shemale/Transexual. well T-Girl for short I say. I work as a construction worker and had just recently start going after my fantasy. I... Read full Story
shemale lover 2012-05-14 3,685 anal sex Cumshot Sex Toys rimjob dildo fucking
73%
Black Girls Have Big Dicks
She was like no woman I had ever seen before. She walked into a room and everyone's eyes were on her. She just had that incredible presence that just lit up the room and everyone just wanted to be around her. I was working behind the bar of a trendy club when I first saw her saunter in on her long l... Read full Story
shemale lover 2012-06-27 21,416 anal sex oral sex black cock
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 6,969 anal sex Big Tits Blowjob ass licking
88%
Purple Kiss, part 1
It happened during a week long trip for work. By the third night in a strange city I had grown tired of the hotel bar and broke away from my work colleagues for change of scenery. I told my coworkers that I was going to bed then quickly made my escape. The night was warm so I decided to take my o... Read full Story
Transadmirer 2016-01-02 10,185 Creampie Shemale Fucks Guy Fetish cum domination gangbang sex
91%
The Beginning Of Penny
This story is about how I became Penny, the cock loving, tranny. I remember being a kid and jerking off to dirty mags we stole from my friend’s dad. The pics that always made me hottest were the ones in the ads in the back few pages for phone sex with trannies. Looking at those hot and perfect women... Read full Story
pennypenny 2017-05-29 10,683 Crossdresser Blowjob Guy Fucks Shemale cum in mouth
100%
one of those stories i wish i was in.
Tim stepped into his new college dorm room and breathed in the possibilities. The sun illuminated the simple tile floor and the simple room furnishings. Freshly cleaned desks and wardrobes neatly lined the walls. The beds had thin blue mats and pencil graffiti etched into the legs. He noticed that t... Read full Story
TylerTheLovely 2018-03-02 6,535 Shemale Fucks Guy
85%
Gilding the Lilly
It was a dark and stormy night. Oh, wait, I was taught NEVER to begin a story like that. (Snoopy can get away with it, but he does all his writing with a typewriter balanced on his doghouse). OK, getting back to important things. It was actually early Autumn out in the Desert, cool weather was s... Read full Story
CharlotteSlut 2018-03-02 6,111 Group Sex Shemale Fucks Guy gangbang Shemale and Girl shemale + shemale
87%
My way to shemale sex
It all started with porn. 10 years ago, i was watching porn on my bed, jerking off watching a girl sucking a big cock. I looked at my cock and started wondering what that beautiful peace of meat tasted like. After a few moments of hesitation, my curiosity took over and i put my back against the wall... Read full Story
andre_xp_8 2018-07-24 13,842 anal Blowjob shemale first time
85%
Transgender orphan meets new kid in town
I stared at the wall of my room. My family had moved over the summer. Tomorrow morning I would start school, in a new town, and all my friends were back East. "California is a great place to live, and Sacramento is a fantastic city! It's the capitol of the state!" My dad had gotten a new job, so ... Read full Story
ASSEaster5678 2019-03-18 6,326 Shemale Fucks Guy
92%
Caught Before My Brother and Friends Could Use Me.
Caught Before My Brother and Friends Could Use Me. By TVTrinity As a boy, I was fascinated by the petite little girl I saw in the mirror when crossdressed. When I got caught dressing by my uncle. I experienced the effect it had on men firsthand. He looked at me the way a man looks at a girl. I... Read full Story
Tvtrinity 2021-04-07 5,953 Teen (18+) Crossdresser Amateur Bareback shemale Guy Fucks Shemale sissy forced young faggot Trinity uncle Richie Budd
91%
Banana Fetish
I was 27 and single and enjoying being free sort of the ‘sworn to fun loyal to non’ stage in young adulthood. I lived alone in a 1-bedroom apartment and loved working on my motorcycle which I kept in my living room. Most Friday nights for me were jamming out to music, enjoying a few beers and tinker... Read full Story
AllenB 2023-02-16 10,054 Latina Fetish Big Cock Guy Fucks Shemale Interracial rimming Homemade Ass to Mouth Banana ass eating
100%
Blind Date
XtinaSmith2017 Anthony awoke to a piercing buzzing tune, a nice enough melody, but one he had come to despise shortly after he had made the mistake of making it his alarm. The culprit, his smart phone, was plugged in on the nightstand beside him and was in the process of making him gleefully aw... Read full Story
Gwapo67 2022-07-01 5,742 Bareback Creampie Shemale Fucks Guy Blowjob
66%
A Series of Perverse Dreams, Part 3
After my last couple dreams, I began to watch a ton of gangbang and bukkake porn. I had jerked to this kinda stuff before but now I was watching it constantly and this time around, it was to the thought of being the girl in the scene. Something about watching a beautiful woman taking numerous cocks ... Read full Story
KaceyKlarissa 2024-03-08 4,823 anal Big Tits Cumshot Creampie Blowjob blonde gangbang big ass sissy Ass to Mouth cum in mouth bimbo bimbofication
95%
Shemale girlfriend
This true life story was posted at our forum by a new member bigbell609. Although it is a pity that he couldn't be with Kristin anymore, his first experience with his TS GF was very remarkable and romantic. Who of us wouldn't love to be in his place... I've been married for a few years now. My wi... Read full Story
shemale lover 2015-04-05 9,733 anal cum fucking
90%
My Shemale Webcam Tube Date With A Sexy Shemale
I was rushing back home from work because I was suppose to have a date via shemale webcam tube with the sexiest shemale I had ever seen. We met few nights ago and I could just feel the chemistry between us getting stronger. I entered my place, dropped my things on the sofa and turned on the lap-top.... Read full Story
shemale lover 2015-12-29 4,041 anal suck Masturbation
100%
Shemale On Webcam Made Me Cum
It wasn't enough for me - regular porn, regular girls... I felt like I was losing it, not having the only thing I really desired: a shemale. But I was new in that world, not knowing where to go, where to look, so I decided it was better to see shemale on webcam first. I searched the internet and ... Read full Story
shemale lover 2015-12-31 4,042 Big Tits Cumshot shemale
70%
Nude She Male Pics At The Porn Company
I was nervous - the people from porn company haven't called me yet, and it was almost a week since I sent the nude she male pics. I'm a pretty attractive shemale - short girl with big ass, decent tits and long dark hair, and a cock which would make any man green with envy - and I really hoped that s... Read full Story
shemale lover 2016-08-10 8,588 suck shemale Big Cock
85%
Shemale Sex Pics Are My Life's Poetry
My younger days are very hard to explain. All I ever wanted to do is to dress in girl's clothes, imagine playing with Barbies and their houses and watching my mom put on her makeup every day before she took me to school. I knew I wanted to become more girl and less boy, but knew nothing about it. ... Read full Story
shemale lover 2016-11-22 5,073 anal sex asshole shemale
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 10,150 anal shemale oral sex
75%
Shemale Bitch
Hi there, First let me introduce myself. My name is Garry, I am 20 year old white guy with brown hair, and stand 5ft 10. I am British, but I have been living in the US for several years now, and this is a story about myself and a young shemale called Nikki. I first met Nikki when I was... Read full Story
shemale lover 2011-08-24 4,410 anal sex suck shemale
85%
Seduced Willingly Part 1
Finally, I moved to a city that was exciting, Miami. I moved to Miami looking for something new and adventurous. I grew up in very conservative town where nothing exciting went on. In Miami I found different languages, gay people, different ethnic persons, art, and culture. However, my job keeps me ... Read full Story
shemale lover 2011-08-31 4,573 asshole shemale fingering
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 19,137 tranny Big Cock jerking off
78%
My Shemale Stepmother Part 2
"Not yet, bitch. You've got to beg for it first," she slapped my face with her semi hard cock, "Now, tell me what you want." "I want your cock, mistress," I said wimpily. "What do you want to do with it, slave," she slapped her cock across my cheek again... Read full Story
shemale lover 2011-09-01 11,441 Cumshot asshole licking sucking
100%
Shemale Fantasy - Suck Fest
This story is completely fictional - in fact it is a fantasy of mine that I will describe in great detail, contact details are at the bottom if you want to make this a reality! I arrive at your house on the evening. You let me in and show me to the spare bedroom. I walk in and close the door behi... Read full Story
shemale lover 2011-09-13 5,385 Cumshot jerking off pantyhose
75%
Tranny whore Samara Rosetti at a Trucker's jo
Last night I got a call from a client. He told me to meet him at a small bar close to Olga Street in Stuttgart. He ordered me to dress as follows: Short black leather mini skirt slit up the side, button down red silk blouse unbuttoned 3 buttons, 16cm spiked heels boots, fishnet body stocking, no br... Read full Story
shemale lover 2011-09-25 7,184 anal shemales hardcore
100%
Sweet Sherri
"The fuck you want," the girl hissed through her teeth. Well, it's hard to say. For one, this was the one night of the week at the particular club that was tranny night. Unless the lucky woman was either a straight freak or had been exposed to the scene, there weren't too many people wa... Read full Story
shemale lover 2011-10-31 5,648 Big Tits transsexual big ass
100%
Tina's Secret
My name is Jordan Conrad. Those of you who read my "Rebecca's Secret" series probably remember me. If you've never read them, I guess I should give you a quick summary, so you're not in the dark about what's been going on in the past few months of my life. Bear with me during the slo... Read full Story
shemale lover 2011-11-02 7,583 asshole shemale oral
100%
Just One of Those Days
Let me start by introducing myself. My name is Amanda, though I sometimes use the shortened version Mandy. I am thirty-three but my sexual awakening didn't really occur until I had turned thirty. Previously I had been a generally shy and quiet girl with a steady and normal relationship. ... Read full Story
shemale lover 2011-12-07 4,854 shemale tattoo shaved
50%
Going Up Part 2
Charlie's cock was as perfect as if it had been sculpted by a consummate artist. The rigid column of flesh rose from the dense thicket of his pubic hair and, lined with blue veins and topped by a once-pink gumdrop-glans that had ripened to a deep purple, looked as inviting as an exotic fruit. The eg... Read full Story
shemale lover 2012-01-01 3,014 Cumshot shemale ass fucking
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 5,079 Fetish shemale Ebony
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 5,305 sucking shemale massage
100%
Rachel and Chris
Part 1 : Rachel and the Ring Yesterday was clear with a light but chilling winter wind present to remind all that the bit of warmth in the sun would only last a couple of hours at best. I struggled between sweating and freezing as I worked to remove the winter street grime from my roadster. Top ... Read full Story
shemale lover 2012-04-10 4,670 Cumshot oral sex Sex Toys
100%
A Nice Surprise
The first time, Alex had been high. Drunk. Stoned. He'd fucked her in the ass and had a great time. She was pale-bodied, slim, long-legged and totally gorgeous. Her ass, after she'd greased it up for him, fit his dick like a hot, slick glove, and he'd ass-fucked her three separate times because of h... Read full Story
shemale lover 2012-04-17 3,710 anal sex Creampie oral sex
50%
The Ultimate Cock Ball Torture
I miss my cock. Sometimes. I had one once - one of my very own, connected right to me - but now it's gone. Never thought I would miss it. I'm sure you've guessed by now that I am a full transexual. I had the boob job and started hormone treatment years ago and felt much better as a shemale th... Read full Story
shemale lover 2012-04-29 3,660 anal sex oral sex
0%
His and Hers Tits - Temptation and Proposition
Canada is a progressive and liberal country. Toronto is its largest city and an incredible place to find state-of-the-art hybrid sexual beauty. Let's talk tits, for example. Young girls with cunts get new and enhanced tits every day. Now it's wonderful to see young girls with cocks get the same high... Read full Story
shemale lover 2012-04-29 3,096 shemale orgasm cock sucking
85%
First Time with she-male
For as long as I can remember, I've preferred my chicks with dicks. There's something about a sexy babe with perfect makeup and hair and a cock that just turns me on. Maybe that makes me a pervert - I don't care! I remember I was just out of high school, 18, the first time I made it with a tranny. S... Read full Story
shemale lover 2012-04-29 4,770 first time Cumshot shemale small cock
100%
Caught and Used
I am a secret, heterosexual panty boy, that loves to dress up in my wife's lingerie when she is not around. My wife and I have two mutual friends named Mike and Mandy. Mike and Mandy had things stored in our garage while they moved. Well my wife had to go away for a day seminar for her company, and ... Read full Story
shemale lover 2012-06-09 5,575 anal shemale Lingerie crossdressing
90%
Darren's Girl?
I'm Darren. I live in downtown Memphis. I head the IT Department in one of the corporate buildings on Second St. I don't consider myself to be the most attractive guy in the world but I don't have any trouble with the ladies. You know, I work out four times a week and run everyday but Sunday. I'm ve... Read full Story
shemale lover 2012-07-20 4,120 anal sex Cumshot transsexual
100%
Shemale Whore and Arab Pimp
Hermaphrodite Whore It had been over a year since Johnny threw that tantrum that ruined me and got him excommunicated from mom. Holding me down when mom walked through the door with her friends, colleagues, whatever and they all gasped and screamed as my big brother finished doing me. We had... Read full Story
shemale lover 2012-07-24 3,104 anal sex Cumshot oral sex hermaphrodite
100%
Blossoming Shemale
My name was James. It was, before everything that happened, anyway. I'd come from pretty good stock, as the snooty, upper class would likely say. I guess I still did, although it would take a DNA test to prove it now, and to be honest, I didn't really have the desire. That was all before. I have to ... Read full Story
shemale lover 2012-08-01 5,095 Cumshot shemale Big Cock oral sex
100%
My Dominate Spanish Mistress Parts two and three
I wasn't going to write anymore for this story but i posted the first part of the story on 99chan's elit board which a recommend going to. Maybe with the help of some of you people writing or encouraging more writers on their stories the board might return to its former glory. After all some guy sa... Read full Story
bruceclark 2012-08-24 4,833 anal Latina domination slut feet
100%
S is for Selena
"His name is Ken," my friend Isabella had told me as she recounted her own encounter and that of her friend. "I got to first base with him that first time he came in the club. Just a quick snog and then he seemed to take fright." "Were you wearing that red dress, the one ... Read full Story
shemale lover 2012-08-27 3,896 anal Cumshot blonde
95%
T-Girl University
Jason was apprehensive about starting college, as any freshman would be. His high school girlfriend, Becky, whom he loved dearly, was going to a different college on the opposite side of the country. They had to promised to stay together but Jason was worried; there would be a lot of temptation for ... Read full Story
shemale lover 2012-09-05 14,903 Cumshot Masturbation Blowjob ass licking redhead