Sort by
Relevancy

Free Stories

62%
Floor Crossdressing Whore
Hey i'm 6'0" 160 and it was my first year in college and I turned 19 over the summer.I am living in an all guy dorm, and I was very nervous to be in a new place, but i knew how i could relax. I set up my computer and went to my favorite website. The site had crossdressing men who got fucked by ... Read full Story
shemale lover 2012-04-08 2,970 Crossdresser Creampie blonde cum swallowing
60%
Booty and the Blue Pill
This is my account of the first time I took a Viagra. At 40 years old I have thankfully never had to go that route but you know curiosity killed the cat. Or in this case opened up my ass! After telling the guys at work how I planned on staying in while my wife was out of town visiting her sister,... Read full Story
shemale lover 2012-04-15 4,265 Cumshot sucking jerking gangbang Interracial
100%
Trained by The Tranny
I have always been considered a strong athletic straight black man. I have fucked a plenty of women being an executive in a high profile position. I had everything a man could ask for Power, Property and Plenty of Pussy. Well in life, all things change. I had just landed another two million dolla... Read full Story
shemale lover 2012-04-15 3,176 anal sex cum oral sex 69 position
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 7,686 anal sex cum oral sex
100%
European Vacation
I was 18 when I first went to Europe. That month would change my life. My parents had died when I was five, and I was raised by family friends; they also controlled my trust fund. It's not a coincidence that I went to Europe just as I came into control of the money. I loved my foster-parents, but... Read full Story
shemale lover 2012-04-21 3,821 anal sex cum oral sex sissy
100%
The Boy is A Girl Now
When I turned 16, I decided to go to a gay bar to see what the deal was. I had not been with anyone ever but I was curious and very much feminine. I stole my older brothers ID and caught the Bus to go to the Ballgame, so I told my mom. Then I wound up at the gay bar just as they opened that night at... Read full Story
shemale lover 2012-05-09 3,715 anal Group Sex sucking rimjob
75%
Nikki in the Woods
About four days had past since my last fuck when I heard from the same guy again. I bumped into him at some local shops and we got talking and I could tell by the bulge growing in his jeans that my presence was having an effect on him. He hinted that he could go a quickie and luckily I had what I ne... Read full Story
shemale lover 2012-06-12 3,127 anal Cumshot fingering cum swallowing
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 2012-06-23 4,602 Cumshot shemale cum swallowing mouth fucking rimjob
33%
My shemale GF Part 3
Christy and I are on the couch, we had just woke up, I have a butt plug in and slept with it in cause she was going to fuck me today. She has a Pink G-string on and a Pink bra with her G-string pushed to the side for her cock. Me I'm wearing Metal Mulisha boxers and a Tyler, the creator T-shirt on, ... Read full Story
shemale lover 2012-07-09 3,528 anal shemale cum jerking oral
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 5,375 cum oral sex cum swallowing face fucking
100%
Finishing School for Shemales Chapter 2
Davina hurried down the hallway, her books clasped in front of her heavy breasts to stop them jiggling as she ran. It had been almost two weeks since she had truly given herself to Mistress K in the beautiful, imposing headmistresses study, drinking the transgendered woman's seed from another T-g... Read full Story
shemale lover 2012-08-09 6,349 cum fingering little cock
100%
Deer Hunting with Daddy
Every year, a group of my family members, mostly uncles and male cousins, all pack up our gear and head into the mountains every fall for the yearly deer hunt. I had been going since I was 5. All the younger cousins slept inside an uncle's trailer, while the adult's and older cousins slept outside i... Read full Story
shemale lover 2012-08-20 5,127 cum fingering oral sex rimjob
100%
Transsexual Sisters Chapter 6
Part 6: A Party to Remember MICHELLE AND NICOLE MAKE A CAREER CHOICE After their tormentors were jailed, Michelle and Nicole felt relieved and happy for the first time in weeks. Whether from curiosity, respect or sympathy for their ordeal they became very popular around the USC campus. They we... Read full Story
shemale lover 2012-09-08 4,148 Cumshot sucking threesome Shemale and Girl deep throat
100%
Dinner with Honey
Meeting people online can be quite a feat sometimes. One never knows if the person is really who they claim to be through their words. So, when the time came to meet in person, she hadn't set any great expectations. "It'll be in a public setting. It's a group meeting, so if it doesn't work o... Read full Story
shemale lover 2012-09-21 3,392 anal sucking transformation orgasm stroking spanking
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 5,590 first time Fetish cum oral crossdressing nylon
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 5,430 cum domination oral sex feminization
55%
First Time Buttslut
I just got home from the adult bookstore, let me tell you what happened to me. Arriving at the abs I went inside and purchased a debit card from the clerk and went into the arcade. Inside the arcade there are eleven booths, two are side by side, I saw that one was occupied so I entered the one besid... Read full Story
shemale lover 2012-10-10 5,291 first time Fetish cum oral sex cd jacking
100%
Doggy Style
"OK, which exit is it?" Trish was driving with Penelope in the passenger seat up front. Meredith sat in the back behind Trish's seat with Angela behind Penelope. The quarter were sisters in a sorority attending an annual Alpha Phi event together. Every year different chapters across Sou... Read full Story
shemale lover 2012-10-17 5,145 swallowing crossdressing sucking off
100%
First Time Out
I'm so excited and want to relate this 100% true story quickly while it's still fresh. Please forgive any typos. [My background: Age 48. Closet dressing in earnest for 15 years. Began with slips stockings and nighties but have collected extensive full wardrobe and accessories over time. Boobs, wi... Read full Story
shemale lover 2012-10-23 3,351 sucking cum Sex Toys
100%
Whore For Two Mexicans
One night I came home from work and saw a old beat up truck from Texas parked in in spot next to my room. As I walk to my room I looked in truck and the back was full of tools and junk, then looking in the cab I could sdee it was a mess with trash everywhere. I thought who ever it belonged to must b... Read full Story
shemale lover 2012-10-27 2,393 Cumshot sucking fingering
92%
The strange day that left me beging for more
I was at work it a friday so I get to have a break from work after i go home anyways i was on my pc at in my offices and i called my secatary in for my papes it was late so there wasnt meny people there when she cam in i notesed that shewasnt my usal secatary she was beautayfull she had big tits dou... Read full Story
shemale lover 2012-10-31 2,801 Cumshot sucking pissing swallowing
100%
Anastasia's Life
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, Barb... Read full Story
shemale lover 2012-11-26 7,200 Fetish cock sucking crossdressing
100%
And The End
In the beginning my initial impression was that she seemed out of place, slightly off balance, perhaps a bit tipsy as she stumbled in her heels up to the microphone. After tugging a bit at her blouse and then adjusting the front so her black lace bra was discreetly hidden beneath the deep cut ruffle... Read full Story
shemale lover 2012-11-27 2,915 sucking cum stroking kissing
100%
When the Balls Drop; A New Years Tale Chapter 5
Chapter Five- Mason's First Taste When Veronica awoke on New Year's Day she was delighted to see that Mason had stayed through the night. In fact she could hear him—what was he up to she wondered— Is that pots and pans I hear—is he—making breakfast? "Wow this one'... Read full Story
shemale lover 2012-12-05 2,357 Cumshot sucking cum swallowing
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 8,663 anal shemales cum
100%
Fun With Friends Chapter 5
When I got home, I spent the rest of the evening thinking about how in a few hours I had gone from a closet cross dresser to a full on cock sucking, bend over and take it up the ass slut who was then shown to a group of strangers as a latex and high heel-wearing sissy. I'm not sure when I fell as... Read full Story
shemale lover 2012-12-12 3,240 Stockings sucking Sex Toys crossdressing heels
90%
First Outdoor Fuck
Sat in my office with nothing to do was making me tired there was no customers to serve which was slowly driving me mad, what was worse was the hot weather outside which always makes me horny, knowing I had all my girly clothes in the boot of my car was making my cock twitch in my cheap nylon work t... Read full Story
shemale lover 2012-12-19 6,298 Crossdresser Outdoor ass fucking pantyhose heels
100%
I Really Don't Know Chapter 1
My girlfriend of 5 years, the woman I love dearly, it's like she's a different person now. Well ... she sort of is. This all started about a week ago, she happened across an ancient artifact. And somehow, against all reality, it had a genie in it – a magical creature whose purpose is to grant ... Read full Story
shemale lover 2013-01-09 3,698 Cumshot sucking Blowjob oral sex big boobs
92%
My Brother's Panties
My brother and I are twins, fraternal not identical. Throughout our lives, no one ever confused us, and furthermore, no one ever thought we were siblings. Growing up I would often get the question, "Kevin, why do you hang out with Jamie so much?" People were always surprised when they lear... Read full Story
shemale lover 2013-01-12 13,728 solo sucking jerking Sex Toys swallowing
100%
Late for Work
She was dressed only in her plain white cotton bra and a skirt when he called her for breakfast. She was frustrated she could not find her favorite blouse and rubbed at the dark circles under her eyes. Picking through the massive pile of clothing she found a gray tank top with a stain on one sid... Read full Story
shemale lover 2013-02-06 6,003 sucking jerking domination Guy Fucks Shemale big boobs
100%
Find That Guy: Porn TV's TG Gameshow Round 02
"Welcome back, ladies and gentlemen, for round 2 of FIND THAT GUY" said the host, giving the camera his cheesiest smile. "We left off with our couple Sue and Winnifred holding only 7 points, and one of their opponents, Vince, having been disqualified. Their remaining opponents are Ric... Read full Story
shemale lover 2013-03-04 3,476 hardcore Cumshot sucking Lingerie ass fucking
100%
A "Girl" for Kelly
Kelly was sort of a loner throughout her life. She had very few friends throughout high school and college, and if she weren't around them, she would spend her time alone. Her love life was just the same. She did have a few boyfriends, and only ever managed to get one to have sex with her. It wasn't... Read full Story
shemale lover 2013-03-27 3,837 hardcore sucking Big Cock Shemale and Girl big boobs
94%
My Shemale Fantasy
Allow me to introduce myself, i’m a young European man, in my early twenties, writing my first erotic story. This has been a fantasy all my life, it probably will remain a fantasy, but that doesnt mean i cant write about it. Ever since i was old enough to realize my raising sexual interest and... Read full Story
Jakester 2013-04-10 31,705 first time Creampie Shemale Fucks Guy ass licking virgin
100%
For my Tgal Mistress
If one night You don't feel sl**py, that's the kind of thing i could do to help You with that: You'd be laying on Your bed, in pyjamas, ready for bed, but not sl**p. i would take Your pants off. First i'd put Your still soft cock in my mouth, feeling it grow bigger on my tongue and sucking it deep... Read full Story
shemale lover 2013-04-30 3,472 Cumshot sucking dildo ass fucking stroking
66%
Franks Friend
Frank is a buddy of mine. We grew up and went to college together. While we were in college Frank and I went on a road trip from Lubbock to Dallas. We got to Dallas went to a few strip clubs and then finally found ourselves on Harry Hines Blvd. It was about 1 in the morning we were both horny and a ... Read full Story
shemale lover 2013-06-05 4,896 Cumshot suck threesome ass licking Guy Fucks Shemale fishnet
75%
For my Tgal Mistress
If one night You don't feel sl**py, that's the kind of thing i could do to help You with that: You'd be laying on Your bed, in pyjamas, ready for bed, but not sl**p. i would take Your pants off. First i'd put Your still soft cock in my mouth, feeling it grow bigger on my tongue and sucking it deep... Read full Story
shemale lover 2013-06-21 2,944 anal ass sex toy Cumshot dildo stroking
94%
A NIGHT WITH A TRANSEXUAL
Since my passionate weekend with a shemale and just getting my ass fucked for three days almost by a beautiful black transexual with a 13" she meat,my fantasy for tranny cock was finally fulfilled,a couple of weeks after that weekend i went to a local gay bar called Crusing 7,it`s was sunday ni... Read full Story
shemale lover 2013-06-22 5,880 suck Creampie Shemale Fucks Guy ass fucking 69
95%
Me dressed as a Gurl
this happened about 25 years ago when i could half way pass i went to this night club for crossdresser, transexuals and transvestites west of balboa park one thursday night it wasn't has busy has on a friday or week end but there was a nice crowd mustly crossdressers a few trannys it was not to late... Read full Story
shemale lover 2013-07-02 5,444 Crossdresser hardcore Creampie ass fucking cd
95%
Dana becomes a woman
All her life, Dana had felt different. Born a boy, she always preferred dressing in girl clothes and playing girl games. She was mistaken for a girl from the time she was toddling - her feminine face and manner always convinced people. By the time she graduated high school, Dana discovered her ma... Read full Story
shemale lover 2013-07-20 4,685 Crossdresser Cumshot Masturbation oral sex ass fingering
93%
Loving TS Sex
living in a medium size city 30 years ago, it was necessary to stay into the closet. That way of live is really still the reason why I never outed myself, even after years living in different bigger cities and several countries. I had acquired a taste for transsexuals, considering them the best o... Read full Story
shemale lover 2013-12-08 4,856 tranny sucking Shemale Fucks Guy ass fucking condom sex
100%
My weekend with Kelly part 9
My weekend with Kelly part 9 6/12/2013 I rolled off of Kelly, pulling her on top of me.She placed her head on my chest as my hands went down to her sweet tight ass. We layed like this for so long we actually fell asleep for about an hour or so. I was awakened to my cock being sucked... Read full Story
Biguynoc 2014-07-08 3,695 anal Creampie shemale ass fucking ass licking
66%
New Black Friends
I go to a small discount store near my house once a week to buy candy. One sales clerk is obviously gay. He is nice to me and we have short conversations when I pay. He is a tall skinny black guy 22 years old and his roommate is short and pudgy. Over the past few months I have often thought to just... Read full Story
FunFemMan 2014-07-08 4,331 Cumshot Big Cock ass fucking Interracial cd
88%
The Bunny Way
I walk over, dressed in a black bunny suit, with fishnet pantyhose, black high heels and little bunny ears. I start rubbing my cock through the bunny suit as I stare at your pole. I start feeling the familiar feelings... I get weak in the knees... I start slowly kneeling, while staring a... Read full Story
lea1234 2014-10-07 3,570 Crossdresser sucking Big Cock jerking sissy
96%
Shemale fun
Recently I've been chatting with a very feminine and beautiful shemale named Lisa. We've been trading photos and dirty talk over chat lines and emails. I've always fanatsized about a cick with a dick and unexpectedly the opportunity came that we could potentially meet. Being married I had to conc... Read full Story
shemale lover 2014-11-25 10,066 tranny suck Creampie Shemale Fucks Guy ass fucking 69
80%
Shemale fun
Recently I've been chatting with a very feminine and beautiful shemale named Lisa. We've been trading photos and dirty talk over chat lines and emails. I've always fanatsized about a cick with a dick and unexpectedly the opportunity came that we could potentially meet. Being married I had to conc... Read full Story
shemale lover 2014-12-03 6,389 tranny suck Creampie Shemale Fucks Guy ass fucking 69
80%
My Shemale experiences
I have had experiences with Shemales. All in Hawaii. Three different ones. I met them all through yahoo chat when it was still fairly popular. In the 1998-2000 time frame. The first one I met up with was doing video shows in some back area part of Honolulu. She agreed to meet me as long as we only h... Read full Story
trisex69 2015-05-20 6,340 anal Shemale Fucks Guy cum oral
82%
My wife made me a bi-sexual
One night me and the wife were out drinking at a lounge on Maine Street it was getting late so we headed back to the car. As we were walking down the street, we walked by this adult bookstore called A-1 Adult Books joking around I said we should go in and look around (They had sex toys, books, and m... Read full Story
JamieLeeCD 2016-04-27 30,884 anal Blowjob cum glory hole bi-sexual
73%
Tabitha at 19
Tabitha’s home from her freshman year of college. She’s gone off to California to a screamingly liberal school and I’m sure she’s been making new friends, learning new things, opening her horizons and fucking safely. After I popped her cherry and we had a very discreet summer of me teaching her a lo... Read full Story
Giantsquid 2017-05-16 6,670 Small Tits Amateur Cumshot Blowjob Guy Fucks Shemale cum in mouth
75%
Morning Head Becomes All Day Affair
I just woke up, super horny, and reach down with my hand, take out your soft cock and slowly work it while your still sleeping. Making it harder...and...harder til it's rock hard, I slip under our silk sheets and wrap my hot mouth around you stiff rod. Licking and caressing it up....a... Read full Story
Go Balls Deep or Go Home 2017-09-12 6,509 Blowjob Big Cock domination Ass to Mouth cum in mouth
88%
Seattle Weekend
Saturday morning and such a beautiful day nice and cool morning I went for a run. I consider myself in fairly good shape for my age but I try and make it to the top of a hill in our neighborhood. I get winded fairly quickly. Coming down the hill I ran into a nice looking athletic girl, maybe 38 year... Read full Story
Jon Paul 2018-08-09 10,080 Big Tits Cumshot Bareback Creampie Blowjob Ladyboy Guy Fucks Shemale cum in mouth
90%
My Recent Holiday Treat
I've come to accept that I am a bit of a dirty girl sometimes. Most of the time I think that I could easily fall into be labeled a nerdy, quiet goth girl, book worm and not at all up of current trends. A misfit as I was called in high school. But there's another side of me. A side that craves sexual... Read full Story
Gothtransgirl41 2018-12-04 6,595 Group Sex Bareback Big Cock Ass to Mouth cum in mouth shemale + shemale
92%
My wife Gwen
My wife, what can I say she is tall and leggy with thick, natural wavy orange-red hair with beautiful porceline skin and just enough freckles to tell you she is a true ginger. Add to that smokey green eyes and thin sexy lips and you can see why people refer to her as Gorgeous Gwen. From the time we... Read full Story
Zöe from Kingston 2019-01-08 7,642 Shemale Fucks Guy redhead Guy Fucks Shemale cum in mouth
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 12,189 Shemale Fucks Guy Guy Fucks Shemale Sex Toys space robots
100%
Getting Fucked By Jeff
Getting Fucked By Jeff I was sitting at the bar one night having a drink and wanting some dick when a man sat next to me and said “Hi, I am Jeff.” Smiling at him, I said” Hi, I am Penny.” Jeff and I chatted and he bought me another drink. After a while, Jeff said” In all honesty, I only boug... Read full Story
pennypenny 2019-02-25 6,362 Crossdresser Amateur Cumshot Bareback Creampie Fetish Blowjob Big Cock redhead Guy Fucks Shemale Ass to Mouth cum in mouth
86%
My adventure at the adult bookstore
I was horny as fuck the other afternoon. I had some time to kill so I hit squirt.org and fetlife seeing if there were any dudes needing a free blo-n-go. Nobody took me up. Sad face. I drove to the local adult book store that has video booths. I was sitting in the parking lot watching people go in... Read full Story
shedawg 2019-04-15 6,294 Amateur Outdoor Blowjob cum in mouth
95%
Best session with a T Girl
I like T-Girls. Recently had a chance to go to Costa Rica for work. While I was there I decided to see what Costa Rica had to offer in this department. There is quite a good amount of girls to select from. I started texting this Tgirl and we set a time. I got ready and headed over. It was a Hotel th... Read full Story
horny.hiker 2019-04-30 14,796 Stockings Masturbation Creampie Shemale Fucks Guy Lingerie rimming Ass to Mouth escort ts no lube anal fuck just saliva