Sort by
Relevancy

Free Stories

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 2,840 anal shemale oral cum swallowing
100%
Amanda and Me Chapter 2
I rolled over after reading Amanda's note with a big smile on my face. I couldn't believe that after all the time I had spent masterbating to shemales and fantasizing about meeting one it had actually happened. Not only had it happened but it had been the most amazing sexual experience of my life. ... Read full Story
shemale lover 2012-10-21 8,607 anal Cumshot shemale oral
100%
How I Became Vanessa Chapter 1
PART I: I was a man before becoming Vanessa, and my name was Mike. I was heterosexual and I was going out with my first "serious" girl friend for two years when all this started. I was still living with my mother who had been divorced for a decade before getting remarried. Her new husba... Read full Story
shemale lover 2012-10-31 3,796 anal Cumshot Masturbation Sex Toys
75%
The dark elavator
I was working on a inportent computer tech. when this women send me a pc to pc message with a picture of a women say want to tast me baby. i look up and she says well how about it and winks i goto get lunch so i goto the elevator but it full. i dont want to take the red elevator its lights fliker... Read full Story
shemale lover 2012-11-18 2,907 anal sex sucking Creampie rimming
100%
Hi, My Name Is Hollie Chapter 2
Hi, everybody! It's me again. Hollie. You remember, the 19-year-old herm-girl with a buxom older sister? It's been a while since I last wrote, but wow. Things are moving right along. And in some fun, unexpected directions! Emillie and I have been spending more quality time together, playing around a... Read full Story
shemale lover 2012-12-19 4,288 Cumshot Masturbation shemale and shemale jerking ass fingering
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 3,786 hardcore sucking Big Cock Shemale and Girl big boobs
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 22,713 hardcore Cumshot sucking ass fucking Guy Fucks Shemale
83%
Cindy She Thong
Dialogue from Cindy’s point of View: Her name is Cindy and she is a shemale. Cindy is a beautiful woman is every way except one. She does not like the term tranny and prefers being referred to as a shemale. She is truly happy living as a woman. She began taking light doses of hormones at 19 she had... Read full Story
mrstanley 2015-07-29 5,109 Big Cock ass fucking deep throat piercing
81%
That night....
I was extremely nervous when I pulled out my phone and dialed the number. Never before, in my wildest dreams, had I thought I would act on one of my strongest fantasies. I knew I would be nervous when I first met her, but after exchanging pictures and seeing that big, fat cock of hers, I knew I ha... Read full Story
bigTHICKY 2017-05-08 9,244 Big Tits Cumshot Latina Big Cock Ladyboy cum in mouth
100%
Incubator
For lack of a better term, I will call him my Lover. I call him Grae, which sounds like "gray" if you are doing a rather poor impersonation of a Scotsman. Not that I have anything against the Scots; that's just as close as I have been able to come to pronouncing his real name. You would think that s... Read full Story
ASSEaster5678 2019-04-23 4,513 Big Tits Bareback Shemale Fucks Guy Big Cock Guy Fucks Shemale monster
50%
There is love, but war
All characters in this story are eighteen years of age or older.* *The following story is inspired by Miss Evie Hyde's "Slut-Box Challenge" story. The following is written with permission from her to use her premise with my own characters and situation* Billy checked his phone when he got th... Read full Story
ASSEaster5678 2019-07-04 3,417 Guy Fucks Shemale bullies
60%
The Greatest Liar, Date With The Devil
The Greatest Liar, Trans Erotica With A Purpose © Alexandra Rios 2019, all rights reserved Disclaimer This is a work of fiction. All characters (including the narrator), firms, business entities, organizations, teams, products, medical providers, medicines, governments, government officials, c... Read full Story
the greatest liar 2019-08-20 4,053 Big Tits Bareback Creampie Guy Fucks Shemale
93%
Virgin Slut Cravings.
There have been so many times that I have had to hide how I felt because I lived my life denying who I was. I was a closet queen who was pretending to be normal. Some might have guessed my secret if they were observant. I didn't do things that other boys my age did. I love hanging out at home like a... Read full Story
Regina10 2020-09-29 8,404 Stockings Crossdresser Big Tits Cumshot Bareback Creampie Blowjob blonde Big Cock Lingerie Guy Fucks Shemale pov
100%
TO BE OR NOT TO BE – PART 6
TO BE OR NOT TO BE – PART 6 by Spanky de Bautumn Part 5. Sunny and Antonio got frisky at the bar, Sunny moved in with Mel and Shari, and opening night was a success The only other dress that I brought was one that I hoped I would get a chance to wear but didn't think I would. It was a black ... Read full Story
SpankydeBautumn 2021-02-26 2,366 Stockings Small Tits Crossdresser Cumshot Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
100%
TO BE OR NOT TO BE – FINAL ACT
TO BE OR NOT TO BE – FINAL ACT by Spanky de Bautumn Part 7. Sunny spent the night with Antonio and the next day they went to Mel and Shari’s for some fun. Antonio had school, so he was up and out early on Tuesday. Mel was in the shower and I was laying in bed, my mind wandering and not real... Read full Story
SpankydeBautumn 2021-03-02 2,454 Small Tits Crossdresser Cumshot Bareback Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
100%
The Golf Bet
A couple of years ago I joined a new golf course, I wasn't the best golfer but very keen, I would be at the practice area almost everyday for at least an hour. Over this time I got to know a number of members and it was a good way of meeting people to play with. Over that year I met a number of new... Read full Story
chris1989r 2022-01-03 4,655 Amateur Cumshot Shemale Fucks Guy Guy Fucks Shemale cum in mouth
100%
Swallowing My First Shemale
Nitromethane It's been a couple of years now that I've been intrigued by shemales, and though I've met up with a few I've met online, I've still not gone any further than some stroking or letting them blow me. I'm not sure what my hangup is, since I can't seem to stop watching these gorgeous gir... Read full Story
Gwapo67 2022-01-18 3,838 Latina cum in mouth
100%
Hooked On Shemale Cock
Nitromethane Well, that did it, I finally swallowed my first load of shemale cum, and I haven't been able to get it out of my mind since. It was three years or so that I'd been wanting to have a shemale cum in my mouth, and it was everything I'd dreamed and more, but now what? I'm at work think... Read full Story
Gwapo67 2022-02-01 3,200 cum in mouth
100%
The Next Level
Nitromethane It's been a couple of weeks now since I sucked my last shemale cock and swallowed her load, and with enough distractions, it hasn't been too difficult keeping myself preoccupied and my mind off of satiating my new fixation. Still though, I do have my moments when I sit back and imagi... Read full Story
Gwapo67 2022-02-01 5,678 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock gangbang domination cum in mouth
50%
DATES NUITS
My wife, Denise, and I have been happily married for over 10 years. Over the years, we have enjoyed a vibrant and adventurous sex life. As we've grown in our marriage, we have become very open and honest about our sexual fantasies and desires. Through the years, we have come to realize that my w... Read full Story
Femboy 2021 2023-02-07 1,292 Stockings Lingerie Shemale and Girl Guy Fucks Shemale Interracial Sex Toys cum in mouth
50%
The first requirement of a deal with Dominatrix Persephone.e
There was a number of requirements before I even consider'd fucking that sissy ass, firstly, I expected dedication to be shown and to prove that the sissy could obey my orders, after a trial period, then I consider to force my big dick down the throat of the that sissy, and then fuck brutally and ex... Read full Story
Dominatrix Persephone 2024-06-21 845 anal solo Cumshot Masturbation Shemale Fucks Guy Big Cock Shemale and Girl domination Mature sissy shemale fucks shemale teen (18+)
90%
Italian hoe!
Verona is a nice city. Here, a motherland of Shakespeare’s “Romeo and Juliet”, there are lots of places of interest to see and enjoy. Verona has much more to offer. The city, also known as Urbs Nobilissima, is the second biggest city in Veneto (after Venice). It is one of the citie... Read full Story
shemale lover 2014-05-11 4,994 ass shemale boobs
100%
My Girl Friend and A Shemale
I walk up to the door of my girlfriend’s apartment. As I start to slide the key into the lock, I can hear slight muffled noises from inside. As the door slowly opens, I am met by the sight of my girlfriend laying with her legs spread wide open on the couch and her super sexy friend Shayla, w... Read full Story
tgirlloverme 2011-09-07 7,508 threesome shemale oral
69%
The Training of Maria Louise
Chapter 1 I’ve decided, since you’ve told me you want to be a little dirty tart, that I should punish you by being a cuckold, someone who’s wife is unfaithful. We will begin by transforming you into Maria, we will apply your make up and dress you in white silk underwear, a nice ... Read full Story
shemale lover 2016-03-20 7,719 shemale Latex
95%
Victoria
I started towards the local theater in my Chevy Corsica to see the midnight showing of some sort of vampire movie. I guess it was a love story where this one girl falls in love with a vampire and vice versa. Oh well... supposedly the books were popular, so might as well see what all of the hype is a... Read full Story
shemale lover 2016-05-08 9,773 anal tranny cum
79%
My Shemale Stepmother Part 1
My parents split up when I was eighteen, I was a little distressed by it but we had never been as close as some. Still, I didn't really see what had driven them apart so quickly and so thoroughly that they never even spoke any more. I guessed maybe one of them must have had an affair and that was re... Read full Story
shemale lover 2011-09-01 18,824 tranny Big Cock jerking off
100%
Allison is Born
What a wonderful day this is. This is the first day of my new life but before that I should give you some history about me. My name is Allison, I am a 24 year old male that lives in a small town in Ohio. My father died when I was very young and I was raised by my mother. I guess you could say I am i... Read full Story
shemale lover 2011-09-24 3,582 Stockings Big Cock cum stroking
92%
All Night Forced Sex Part 4
When I woke up all I had on was very small running shorts that had a slit up each side and a t-shirt. The shorts were unable to contain my hard-on so I let it stick out the bottom. No one was around and it felt nasty hot. I snapped out of my daze and began to panic just as she opened the door. &q... Read full Story
shemale lover 2011-10-10 14,380 asshole shemale cum
95%
Interesting Suprise
This all happened several years ago when I was in the Navy in San Diego. One payday weekend I was in a partying mood so I thought I would head down to Tijuana for some fun. Being I was about 20 at the time I headed for one of the clubs where a lot of the college kids hung out hoping that I might g... Read full Story
bjw_6 2011-10-23 7,624 suck Bareback Shemale Fucks Guy Guy Fucks Shemale 69
93%
The Babysitter's Secret Part 2
Two months had passed since Jenny and I had first made love on that fateful, snowy night. At least once a week, occasionally many more, Jenny and I had found time to be alone and indulge in our secret affair. I had never believed any sexual experience could be greater than our first time together bu... Read full Story
shemale lover 2011-10-24 6,625 Stockings shemale oral sex bisexual
73%
Vegas Baby: Swinging for the Fences
"Hello," Miss K said as she answered the phone. "Where are ya? You're gonna be here in 5? Alright. You got the address for IHOP, right? OK, See ya in a bit. Bye." "So is this girlfriend of yours on her way?" Jennifer chimed in. "I mean if she doesn't exist, this... Read full Story
shemale lover 2011-11-15 5,366 anal oral handjob
97%
Stepdaughter's Transexual Surprise
I've been through two marriages in the past. My first wife died at an early age of 29 from a massive heart attack and my second marriage was a nightmare from hell, that I'm now free of. When I met Jeanie, I knew I had to take it slow and easy. Jeanie was a very nice lady in her early 40's. I myse... Read full Story
shemale lover 2011-12-04 13,526 anal Fetish transexual
80%
A Fairy Tale Part 1
=-=-Chapter One-=-= "Heather?" My boyfriend was knocking on the bathroom door. "What's wrong, are you okay? Heather?" "Yeah..." I swallowed thickly and that was a mistake. I threw up some more, kneeling on the floor, feeling like I was dying. "Heather?&q... Read full Story
shemale lover 2011-12-06 11,421 Bareback cum ass fucking slave
50%
Farria
It was hard times for Dre. His business had failed and he had fallen into bankruptcy. His wife left him after he was caught cheating with another male... a male dressed up as a woman. He was financially in the dumps and had to go move in with his little brother Ray. Ray had recently moved o... Read full Story
shemale lover 2012-01-28 2,511 Big Tits sucking cum fucking
100%
His teacher, The transsexual
Greg was late for class. He ran through the hallways. They were very particular about being punctual here. His health teacher especially. She was very focused on such things. Greg had been late twice this week. He couldn't help that his car kept breaking down. Ms. Sin was a real hardass and didn't a... Read full Story
shemale lover 2012-01-31 9,705 shemale Big Cock teacher
50%
Freak House Superstar Come Fest
Kiki and Ty Blaze were doing their thing. They were living on their love and passion, literally. The couple had taken their love, passion and desire to please one another and turned it into their livelihood. They had become stars in the world of underground porn. Their production studio, Nasty Nigga... Read full Story
shemale lover 2012-02-01 6,281 anal shemales Group Sex
100%
Eve Quest Part 4
Chapter 16 Monday morning I was told to wear my red panties, bra and ribbon; my white collar, bracelets and heels and a red sleeveless dress. Sheila and Jenny ate breakfast, got dressed and loaded me in the car. They dropped me off in front of the beauty parlor and Jenny said. "If Hilda f... Read full Story
shemale lover 2012-04-21 4,015 anal sex domination oral sex transvestite
100%
A Real Fantasy
It was a boring Wednesday evening. I was away from home on business. With nobody to talk to and nothing good on the TV I decided to go for a walk. I walked for a few blocks and noticed the neighborhood was changing from hotels and bars to strip clubs and adult bookstores. I had never been to a strip... Read full Story
shemale lover 2012-05-28 5,694 anal sex Cumshot Creampie facial oral sex
100%
Cathy's Friend, Transsexual Mary
I have told you about my daughter Cathy. She is a stripper at a nude club. She has sucked me and I have got to fuck her in her ass. All this in front of her friend Bill and Mary. Bill is Bi, like me and Mary is a transsexual. I'm also a cross dresser. Just two weeks ago I found out that my daught... Read full Story
shemale lover 2012-06-05 3,900 anal sex shemale facefucking jacking off
87%
Feminized By My Mother
Hello. My name is Dan. I'm doing okay, you? I see. Well if you are going to be listening to my thoughts please keep the volume down, I am trying to think. Some things are going on that have got me very mixed up and I have to concentrate. Like most overly complicated things in life, a woman is inv... Read full Story
shemale lover 2012-07-24 67,189 Fetish shemale oral feminization
100%
David to Dee
"Dave," she purred, "you know you can tell me anything. Surely you know you can trust me not to judge you by your fantasies." He was squirming under her touch, his eyes tightly shut, trying to avoid telling her his deepest secrets on the one hand, and on the other, hoping beyo... Read full Story
shemale lover 2012-07-29 12,469 Cumshot Masturbation oral sex
76%
Porn Princess
They say if you are going on a journey of revenge, to dig 2 graves, one for your enemy and one for yourself. I thought I understood the meaning of that saying, but never so much as right now. My name is Dan, and at the age of 21, I had been working for nearly 2 years as a production manager for ... Read full Story
shemale lover 2012-09-02 23,913 Cumshot Blowjob fuck fingering big boobs
100%
Wife Converts Husband Chapter 3
After about a month of being dressed up and acting as a female, trying out all the different outfits we had purchased and Shelley feeding her strap on cock to my willing mouth and ass every chance she got. My ass and mouth was now well and truly broken in. Shelley came home one arvo with a flyer ... Read full Story
shemale lover 2012-10-18 5,438 anal sex sucking cum swallowing
100%
Amanda and Me
I walked in the door of my one bedroom apartment and headed straight for the computer. Lately it seemed like I had the same boring routine everyday: get up early, work all day at my stressful IT job, go straight to the computer when I get home to look at porn and masterbate, then eat dinner and go t... Read full Story
shemale lover 2012-10-21 7,268 Cumshot sucking shemale
100%
Amazon Adventures
My name is Bartleby Adams. Most people call me Bart. I have always been a sexually adventurous guy. Always. Fortunately for me, I've got the means to explore the kind of life that most people dream of. I was born into it, you see. My mother, Stacy Mendoza married a man named Paul Adams. He was fabul... Read full Story
shemale lover 2012-10-23 4,248 shemale oral sex kissing
95%
Fitting Room
Several years ago when I was just starting collage I had just gotten my grant money and like a good responsible young man I decided to spend it on some new clothes to try to be more attractive to women. I went to a clothing store that had both men's and women's clothing. While browsing around the me... Read full Story
shemale lover 2012-11-03 4,772 anal cum oral deepthroating
100%
Westward bound cum slut Chapter 2
Again I'm on the big bird headed out west for another fling. This time is going to be way different though, the players have increased, not to mention both sexes. The tale unwinds in the same fashion as the last trip out this way, the plane flight was long and boring, and being very nervous didn'... Read full Story
shemale lover 2012-12-16 3,528 anal Group Sex sucking Creampie cum domination
100%
Young Sissy Chapter 1
I don't know how long I was under...days, weeks...who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck with needles, filling me with horribly persuasive dreams of a beautiful new body. I tried to imagine myself as a man, just to s... Read full Story
shemale lover 2013-01-04 10,131 sucking Fetish Uniform domination big boobs
93%
Miss Bernie
My name is Bernice McDonald and I am the very happy owner/ operator of a couple of children's day-care centers. I love my life and I love this work. I love children and since I have one of my own this helps satisfy my need to nurture. I have not always felt or recognized this need. I was born in... Read full Story
shemale lover 2013-02-22 14,013 hardcore sucking ass fucking Guy Fucks Shemale
98%
Fantasy cums true
I was on a business trip staying in a nice Hotel. After a business meeting in my room I called down for room service. The maid came up a few minutes later and I let her in. She was stunning, 5' tall with black hair and the bluest eyes I have ever seen. Under her uniform you could tell she was very w... Read full Story
shemale lover 2013-07-11 8,447 anal sex Cumshot suck Creampie Shemale Fucks Guy fingering
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 5,082 hardcore oral sex big boobs kissing shemale sex
100%
Salacious Sarah
Joe Dodge walked down bustling Market Street in Philadelphia in awe. Joe and his wife Tammy moved here 4 months ago from a small town in Alabama. The 24 year old man missed his hometown but at the same time he marveled at the sights in the big city. It was Friday evening, he always went straight hom... Read full Story
shemale lover 2013-07-18 8,394 anal sex Ebony oral sex Interracial kissing
94%
Renting out a room
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 a l... Read full Story
Alic91lovesporn 2015-07-29 21,277 suck shemale jerking orgasm domination
85%
THE WEATHERGIRL BY B-MAN
PART 1: A COURTESY CLIENT BLOWJOB Three weeks into my gig at Coxon & Dicster had been a blast. At first, a few of the girls had some reservations about me working there because I wasn't transgendered myself but I guess I won them over with my naturally cheerful personality. At least,... Read full Story
bennyx709 2015-07-29 7,426 Crossdresser hardcore ass fucking cd
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 13,446 first time tranny ass fucking guy on shemale mutual suck
69%
Motel Blackout
I always enjoy my sales trips. The trips fit into my crossdressing lifestyle and the thrill of being in a different town and different people. After a long day on the road, I had just checked into a motel just about 30-miles outside of Nashville, TN. For my overnight trips, I always bring my spe... Read full Story
browncherrygurl 2017-05-25 18,087 anal Crossdresser ass fucking sissy forced