Sort by
Relevancy

Free Stories

50%
My friend Barbara,
My friend Barbara, I look forward to welcoming Barbara. She is a lovely brunette with blue eyes who likes to make love without taboos. She knows how to bring our fantasies to life by imagining exciting role-playing games. - You're going to fall in love when you discover my underwear, she assur... Read full Story
sandratvtg 2024-07-04 830 Stockings Bareback Fetish transsexual Lingerie Sex Toys travesti Vintage rosebud plug gonflable gode xxl
96%
Family Frolic
FRIDAY My sister and her husband wanted to take a few weeks off in the sun and asked me to look after their kids for a while. I'd move out of my tiny apartment and into their house for the duration. As I was still living off my severance and they had a nice spread with an indoor pool and a h... Read full Story
shemale lover 2012-01-14 30,963 strapon porn
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 4,581 Cumshot oral sex Sex Toys
50%
Hard Decisions by Elaine © 2020
Hard Decisions by Elaine © 2020 No one in this story is based on anyone alive or dead. It is a work of fiction and should not be read by minors. I appreciate the kind efforts of many of my friends who cast a welcoming glance over the initial writings. I owe you all a big debt of thanks. Prolog... Read full Story
Elainetguk 2023-09-06 4,818 Stockings Big Tits Creampie Lingerie Guy Fucks Shemale Mature
100%
Best Ride Share of My Life
It was a random Friday night. I was feeling a little frisky but didn’t have anything specific in mindA friend of mine works at a gay bar not too far from my house. Knowing my friend worked there I figured I could head over around midnight and see if there was something worth getting up to and if not... Read full Story
baldbeardbottom 2024-01-16 6,160 anal Amateur Cumshot Bareback Lingerie Guy Fucks Shemale Homemade
50%
Transgender Art: A Sampler
It's not often that transgender art offers viewers a glimpse of a female-to-male transsexual. Usually, the transformation is in the other direction, with the loss of the vagina in favor of male genitals and the acquisition of female breasts. However, one image does reverse this trend, showing a fema... Read full Story
shemale lover 2011-09-06 3,591 shemale transsexual transgender
100%
Ticket To Paradise
Oh, no! Toni Matthews thought as she saw the red, blue, and amber emergency lights flashing in her rear-view mirror and heard the shrill siren of the police car shrieking like a banshee. She was being pulled over by a California Highway Patrol officer. She’d been speeding, she knew, but maybe,... Read full Story
shemale lover 2011-12-19 3,204 hardcore erotica romance
37%
My Deviant Tgirl
I guess it was one of those tranny surprise moments she was a sexy shemale, I was a horny guy, nothing more... However, it is one of these transexual stories you simply must hear. You may think it's just transgender fiction, but I assure you: It's all true. I always found transgender fiction and ... Read full Story
shemale lover 2012-03-26 5,778 huge cock big boobs tgirl
100%
Hot Trannys & Ebony Shemale Cum
I've always considered myself as a huge fan of heshe cum & porn vids. You tell me what else a man needs besides a tgirl's cock, a nice portion of shemales fucking and sucking & loads of transgender stories to tell the guys... Forget about the usual trans sexual pictures & pre-op transsex... Read full Story
shemale lover 2012-03-27 5,109 big dick blonde cum fingering huge tits
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 10,078 Big Tits Cumshot Bareback Creampie Blowjob Ladyboy Guy Fucks Shemale cum in mouth
95%
Late night park visit
It was 11pm on a Friday night, I was driving my car back from a failed meetup with a guy I met online a couple of days prior. I thought it was going to be an amazing night, so I spent close to two hours getting my makeup and hair sorted to look pretty for him when we met. I was wearing a short black... Read full Story
Natalie Bishop 2018-10-08 7,190 Amateur Cumshot Bareback Creampie Big Cock Ladyboy domination Guy Fucks Shemale public Park
33%
Kimberly Wilder: An Assessment
Pull up a chair. Oh. That's right. If you're reading this article, you're most likely at your computer monitor, which means that you've already pulled up a chair. Okay, good. In this article, I'm going to review the splendid art of a magnificent (and very beautiful, too, by the way) transgende... Read full Story
shemale lover 2011-09-19 7,625 transsexual tgirl cock sucker
40%
Redux
Today, Stormy Danielson was re-creating the late Renaissance's Antonio Allegri da Correggio's Jupiter and Io. Danielson's re-creation was to remain true to the original in every way but one--the same detail, if one could call such a feature a mere "detail"--that his anonymous billionaire p... Read full Story
shemale lover 2011-10-04 3,395 anal sex asshole cum deep penetration
83%
More Than a Lady
Doctor Carter surveyed the gathering of ladies before him. Something wasn't quite right, but he just couldn't put his finger on what it was. He had been invited to speak on Female Reproductive Health but the women before him were neither the charity-driven older matrons nor eager young housewives th... Read full Story
shemale lover 2011-11-24 4,376 pissing Ladyboy Mature
50%
Memory Master
“I can remember whatever I want, whenever I want?” Amanda asked. The salesman nodded, patting the dome of the Memory Master. “Whatever you program.” He’d already explained the procedure twice, but he’d explain it a hundred more times if need be, to make a sale.... Read full Story
shemale lover 2012-01-02 2,944 Cumshot ass fucking deep penetration
87%
It does not get any better than this
15 years ago, I went into my older b*****r's room to grab a porno mag. He had stacks of them all over the place. I wasn't too choosy. I picked the magazine off of the top of the pile that was closest to his bed and went into the bathroom. My usual routine was to open the mag, find a babe, pull out m... Read full Story
shemale lover 2012-01-03 4,511 shemales taboo Fetish
57%
It doesn't get any better than this!
15 years ago, I went into my older brother's room to grab a porno mag. He had stacks of them all over the place. I wasn't too choosy. I picked the magazine off of the top of the pile that was closest to his bed and went into the bathroom. My usual routine was to open the mag, find a babe, pull out m... Read full Story
shemale lover 2012-05-17 3,424 shemales Fetish jerking off tgirls
100%
Hits, Misses: G
Ok, what follows are some accounts of hookups and almost hookups I've had with transwomen in the late 2000s, early 2010s. Some I think about a lot. Others I've forgotten completely and am attempting to interrogate my memories. Things have changed a lot in the culture, mostly for the better. Visibili... Read full Story
bybaking 2024-02-06 4,823 anal Amateur Cumshot Bareback Big Cock Ebony Guy Fucks Shemale Interracial black Tgirl
100%
Khwaish Pune fucked me hard
I am a shemale trans lover. Me 6 ft tall, muscular, handsome , fair man 52 resides at pune. I use tobe top but last two years I am living being bottom too. I love sucking shecocks and hv sucked quite few in pune. Story begins when I was looking for some trans partner on Planet Romeo I came acro... Read full Story
Stud4Shemale 2024-04-14 3,139 cum in mouth Indian Shemale Pune Shemale Shemale Fuck Man hard-core shenale fuck
78%
First Time Having Sex With A Shemale
Ok let's begin so I was walking down the street going to the store one day I saw a woman and her daughter moving into a house they had some heavy boxes that they need help with. At first I thought she was white girl but when I got closer to them they we're Asian becuase i only saw the back and they ... Read full Story
bigtranslover 2011-05-21 14,988 first time shemales interracial sex
100%
The Scenic Route
Ahead, the desert highway was flooded. But for Rose's own car, a cherry red 2008 Ford Mustang, the route had been empty for the past half hour. It was no surprise that the road had been nicknamed "The Loneliest Highway in America." The loneliness was fine with Rose, though. In fact, she pr... Read full Story
shemale lover 2011-10-31 3,397 blonde shemale
100%
Joey Says
My sister Beth had phoned to say she was in the neighbourhood, and could she call in. In fact she had a few days and could I put her up. It had been ages since I had last seen her but of course she was very welcome. I am Mat, 28 and recently separated from Kate. Beth is a year younger and as far ... Read full Story
shemale lover 2011-11-05 5,506 shemale oral Sex Toys
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 4,597 sucking cum fingering
66%
Candy Pink Part 2
Chapter 4 My parents had a letter shortly after from the headmaster Mr. James Allen. I was to head out to CA before the start of winter term to get settled into the dorms and go through orientation. The letter said I should be there no later than December 1st and that they would arrange for me to... Read full Story
shemale lover 2011-12-08 4,435 taboo Fetish crossdressing
100%
Anastasia's Life So Far
Chapter 1: Humbling Beginnings My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barbi... Read full Story
shemale lover 2012-11-27 11,007 Fetish crossdressing feminization
87%
Why you should never cam
* Sorry for the poor writing but since it is the summer and I am taking sometime off to reflect before starting school next year I thought I would write up about what had happened to me the summer before. It is currently a work in progress and if spot any spelling mistakes or errors feel free to cor... Read full Story
jennychen 2014-09-02 5,226 cock shemale Big Cock Asian
100%
Two CD's the first time we meet.....
We are meeting for the first time since talking online. I want to dress for you gurl, I want to feel as you do, I want to be your slut, your slave of desire. My panties are a sheer white, my hard cock can be seen ever so pressing against them, I rub myself for you as you watch, drooling now. Hand... Read full Story
kelliecdgirl 2024-04-10 3,877 Stockings Crossdresser Cumshot Masturbation Fetish blonde Big Cock Lingerie pantyhose Frottage sissy femboy shemale + shemale
71%
Blind Date
"Hello, I'm supposed to be meeting a Mr. James here." The receptionist looked up from her desk and glared at Zil, seriously not smiling. "I believe you'll find him in his suite, on the first floor. The River Suite." She snapped, returning to her bookwork without giving so m... Read full Story
shemale lover 2011-10-30 7,055 suck shemale cum
33%
A Certain Perception
Kyra was not the girl of my dreams. I never DARED dream a woman that good would just walk into my life. She was smart, sassy, vivacious, intuitive, resourceful, and a real 'people person'. We met in an Internet chat room called "Working Girls". We're not talking about the kind you find in ... Read full Story
shemale lover 2012-02-23 8,239 Fetish transformation dildo
40%
Kiara's Xtra large treat
I have developed an interest in t girls with the XXL tag, black and Latino girls especially seem gifted in that department, so when I seen this horney bunny on an escort page I knew I'd have to check her stats. A dark Latino Kiara boasted an impressive ten inches, I pondered on my way to meet her... Read full Story
Kinky Dee 2019-05-27 3,573 Small Tits Big Cock Lingerie domination Guy Fucks Shemale Interracial
57%
Nicks Shemale Experience
Nick had discovered he had a thing for shemales 4 months ago after stumbling across some pictures on the Internet of a really hot ladyboy from a porn link site. This sort of thing had never turned nick on before but looking at pictures of the small-breasted brunette really made his dick hard. It did... Read full Story
shemale lover 2011-08-22 3,880 anal Fetish oral
50%
Lust and Love with Leona
This is a work of fiction. * The days after I fucked with Leona I spent alone. She has told me that she was going for shoot in the Bahamas for a week. I was a man who had everything in terms of material comforts, and there was not a girl I couldn't pull in a bar. But I found that I could not s... Read full Story
shemale lover 2011-10-07 4,580 hardcore celebrities oral extreme
100%
Once Upon a Tranny
Bob was having a time with the winter traffic. It had snowed last night, the roads were slick, and all too many people were driving like they had never seen the stuff before. He had started out early in what turned out to be a vain attempt to get to the office on time. Conditions were worse than he ... Read full Story
shemale lover 2011-10-30 5,221 asshole Creampie shemale
100%
TV television
My girlfriend Gloria and I had just moved into an apartment together, having gone out for six months or so, before making the committment. We moved in furniture from each of our apartments, after deciding what would go best in the new place. With the exception of a television, we really had everythi... Read full Story
shemale lover 2011-12-11 5,256 Fetish trans tv
80%
Wrong Vampire
I consider myself a fairly tolerant person. I judge each person on their merits, not their skin color, gender or even sexual orientation. I'm even in favor of the Vampire Rights Amendment, but I must admit, unlike other groups people discriminate against, they make me uneasy. They claim that all the... Read full Story
ASSEaster5678 2019-04-23 6,548 Cumshot Shemale Fucks Guy Guy Fucks Shemale cum in mouth vampire
100%
Masturbation fantasies 2: Looking for Amanda
Previously: William, a young lawyer who has no luck with women, decide he needs some relief from a live girl. Scared of going with a prostitute, he decides to try out a peep show first. Without knowing that the stripper he chose is kind of special, he ends up in a show with a shemale called Amanda w... Read full Story
ThatEroticWriter 2019-07-24 8,894 Big Tits Cumshot Masturbation threesome Frottage
100%
Dominated sissy goodgurl34
Mmmm ty Sir Deitrich --I'm standing in your open doorway wearing black latex stockings and garter and some hott red lace panties over top -I have a black corset on and a very sheer dress on ,wig and gurl mask ---my wrists are cuffed to a circle hook one on each side of the doorway door jam about 6... Read full Story
goodgurl34 2022-03-15 2,348 Crossdresser threesome redhead domination Guy Fucks Shemale Sex Toys Homemade shemale + shemale
100%
A true first time.
I want to preface this reiterating that this is a real story about my first ever experience with a shemale. It's a memory I will hold forever as it was everything I could have hoped for and, as I may share in the future, lead to other experiences, too. A little history of before the first meet ac... Read full Story
Gtaaddict3 2023-11-21 8,563 first time cock suck Blowjob shemale Big Cock trans oral fantasy virgin escort big first time
75%
by a Shemale Part 3
I woke up the next morning not sure what just happened was real or if I just dreamed it than I looked around. I was laying naked in this mammoth canopy bed the bed spread and canopy were both pink and feminine and I realized it wasn't a dream I couldn't believe I was begging to be fucked. ... Read full Story
shemale lover 2011-08-29 4,434 Cumshot asshole fingering
100%
Additional Thoughts on Sodomy
Although, in the world (or worlds?) of pornography and erotica, it is politically incorrect, perhaps, to suggest that the body, whether male or female, is not built for anal intercourse, the fact is that anyone who has participated in this act (especially on the receiving end) or who has enjoyed wat... Read full Story
shemale lover 2011-10-05 3,999 Creampie sperm anus
58%
Janet Owns Me Now Chapter 5
It was a beautiful summer's day, perfect beach weather. i packed a light lunch and a bottle of chardonnay in the cooler and we headed for the closest beach, about a forty minute drive away. J. Looked beautiful in Her black two-piece bathing suit and floral silky wrap, Her hand light and warm on my l... Read full Story
shemale lover 2013-01-30 3,672 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
86%
My TS experience in India, Pune
Im 6 ft tall fair with handsome looks and regular exercise keeps me fit and healthy. Im also blessed with quite big and thick cock with indian standards. Im total shemale fan and I watch shemale porn crazily every day. I was in search of TS or Shemale in pune since long then one day I was searchin... Read full Story
daynightfun7 2013-07-10 13,184 suck shemale fingering ass fucking Guy Fucks Shemale condom sex
75%
Bambii's New World
My mind was racing the whole time. I couldn't believe where I ended up. But the sensations were running through my body. A 9-inch cock was ramming my boy pussy as hard as it could. Another cock, at least 10 inches, was being forced down my throat as his hands wrapped around my head, forcing me to... Read full Story
shemale lover 2011-10-05 5,163 shemales Blowjob cum
100%
A Maid Family Part 2
Sitting up with a start I felt the cold wet cloth that someone had put onto my brow fall into my lap, and then shortly after that I felt it slide in between my crotch and then onto the seat of the leather sofa where as luck would have it the damn thing then wedged up against me, and after a few ... Read full Story
shemale lover 2012-01-02 3,696 shemale femdom tg
75%
Blue collar Master, white collar slave Part 2
About an hour later I was once again naked except for my chastity pouch and my stilettos and once again I was screaming and crying, my body covered with angry red welts from Master Darren's whip. On my knees crying and begging I held his cock in my hands, trying to give the best handjob ... Read full Story
shemale lover 2012-01-13 11,344 torture extreme fiction bondage and discipline
100%
The Greatest Lie Part 3
My weekend escapade with my first real lover, Jake, convinced me that I was destined to live as a girl, despite having been born a boy. Unfortunately, it was my male persona to whom the University of Minnesota had extended admission and a scholarship, and I wasn’t quite sure how they would rea... Read full Story
shemale lover 2012-01-19 4,324 hardcore crossdressing erotic encounters
90%
My True-Love Story
My name is Kim Young. I'm a happy and healthy nineteen this year. This is my very first story (but not my first "submission!") My story begins five years ago, when our neighbors moved in next door. I'll always remember that sunny April afternoon in Omaha, when they climbed out of their ... Read full Story
shemale lover 2012-09-10 5,778 Crossdresser Blowjob pissing Lingerie handjob
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 5,761 Teen (18+) Crossdresser Amateur Bareback shemale Guy Fucks Shemale sissy forced young faggot Trinity uncle Richie Budd
100%
Charisma Part 1
Tiffany De Vine wondered whether the ladies’ dressing room in which she was about to try on a brassiere was under surveillance by some fat, obese fucker with a day’s stubble of beard and a cum-stained crotch. Probably, she thought; it would be just her luck. Well, if some slob was drooli... Read full Story
shemale lover 2011-09-03 3,591 Big Tits shemale Lingerie
50%
Domination Island Part 3
At last the shemale came out from the cells. She had a great big smug smirk on her face. Lavina had been as patient as she could be, but now she was so randy beads of pre-come moistened her swollen cock-head. The shemale had gone over her time but it wasn't worth complaining. Most did. It was o... Read full Story
shemale lover 2011-09-24 10,461 bdsm shemale Big Cock
100%
Me & Miss Cocker
A few weeks ago, I moved into the final year of school. Our English teacher had left at the end of the previous school year, and we had a new teacher, Miss Cocker. Now to say Miss Cocker is a babe is an understatement, she is about 6.2' tall and she has long voluptuous legs, which are usually sto... Read full Story
shemale lover 2011-10-30 3,907 Creampie transsexual ass licking oral sex
50%
Twisted
"Baby, are you sure this is the place?" Eve squealed a bit too loudly, her voice both high-pitched and thick from the third Cosmopolitan. "This looks so, I don't know; fancy-shmancy for a full on mix-it-up ladyboy bar. I know, I know, this is South Beach and everything here is la-de-d... Read full Story
shemale lover 2011-10-31 4,881 shemales Big Tits fingering oral sex
100%
Young Hercules: Versatile Stud by The Fan
Prometheus Academy. It sat atop a hill, dominating the vast region of Thessaly, Greece. It was the most prestigious school in the area. The most famous men and women of the world came there to get their education. The sons and daughters of kings and queens, ... Read full Story
shemale lover 2011-12-01 3,355 anal Creampie jacking off
100%
The Greatest Lie Part 9
Two hours after saying goodbye to Rick and Randy, Tran and I left Minneapolis and boarded a plane to LA. I fell asleep at take off, and woke as the plane began its descent. Tran was staring out the window at the city’s lights spread in an endless shimmering galaxy below. "Wow, I love LA a... Read full Story
shemale lover 2012-01-19 3,849 hardcore erotic encounters fantastic
100%
Shemale Mistress
Tony turns 21 and decides to go party with his friends. Tony, with Bob and Chuck, (his college roommates) want to try out a bar on the other side of town - a new bar called "Desires" that they had heard a lot about, but never visited. The bar was known for wild and crazy parties. They also... Read full Story
shemale lover 2012-05-02 4,930 Cumshot domination cum swallowing facefucking huge dick
100%
Date Sex!
I wake up, my head throbbing. "Ugh, what a nightmare." I think to myself as I try to shake the sleep and cobwebs from my mind. My head splitting with a headache, it starts to register that something doesn't feel right. "It was just a dream Mar..." I tell myself as I t... Read full Story
shemale lover 2012-07-24 4,443 shemale domination oral sex