Sort by
Relevancy

Free Stories

50%
Caitlin and Mistress Vicky Chapter 3
I was sitting nervously in front of the mirror in the newly decorated guest room. Chad was set to arrive in half an hour. My wife was getting ready in what was for now our bedroom. She had told me to dress up for the occasion, though I was still to wear my maid's outfit. I opened my jewelry box and ... Read full Story
shemale lover 2012-03-01 3,307 suck Fetish fuck domination
66%
Why did I settle for that?
Just made it back from Miami, was a great visit, but it could have ended after the first night, and that would have been alright. Hated the dirnking and the smoke, but did meet another lovely tranny who did give me the tour and the break from this horrid northern weather. Although the sex with he... Read full Story
shemale lover 2012-03-06 1,972 tranny fuck erotic encounter
100%
A Halloween to Remember
Saturday morning I woke up feeling strangely euphoric. I remember thinking about it for a moment, and then realizing: it was Halloween. Cheryl and I had been invited to a party! The next morning (and for many, many mornings thereafter), I would remember that Saturday as one of the epic erotic encoun... Read full Story
shemale lover 2012-03-08 4,952 cum oral sex long cock
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 23,823 Cumshot Blowjob fuck fingering big boobs
27%
I have been out dune by my little brother by a big difference hi
I am 32 years old and my lady who was 46 and my little brother who was just 14 years old then wanted to have some fun and get my woman who was just the right for him he was just out of his mind about her and I was like I'm all about it and I was thinking that I was going to be the big cock an h... Read full Story
Not long but hard 2017-10-19 5,795 Big Tits gangbang Shemale and Girl Solo Shemale Cartoon shemale + shemale Wow.
100%
Fuck Talk with Melanie Jackson (A talk show transcripy)
THIS IS AN ORIGINAL TRANSCRIPT OF THE PROGRAM “FUCK TALK W/ MELANIE JACKSON” DATED MARCH 10TH 20__ MUSIC CUES ANNOUNCER: Hey everybody! Welcome to “Fuck Talk” with Melanie Jackson”! The show that talks about, you guessed it! FUCKING! Any kind of fucking! Straight fucking! Gay fucking! Any kin... Read full Story
bennyx709 2018-08-28 4,491 Cumshot Blowjob Big Cock Interracial Mature
80%
One night Transtand ;)
One Night Transtand By BalkanMan990 Published on Lush Stories on 05 Oct 2019 I had no idea she was a trans.. I didn't stop kissing or fondling her when I found out. I went out for a drink at one of the many bars at Croatia,where my girlfriend Sabina and I were staying.Sabina and I had been drin... Read full Story
BalkanLoco91Ri 2019-10-24 8,782 Small Tits Amateur Cumshot Masturbation Creampie Shemale Fucks Guy Blowjob blonde Lingerie Guy Fucks Shemale Homemade pov cum in mouth
84%
She never saw it coming
When I was 19/20 I used to frequent LGBT bars roughly twice every month. Most nights not much would happen but I found myself going to the trans nights more often. Until I eventually had some experience with trans girls. It was mostly fairly soft fun. Me getting oral and occasionally topping th... Read full Story
chris1989r 2022-02-01 4,986 shemale gangbang facial
0%
The Greatest Lie Part 13
Does Life Imitate Art? I love technology, in spite of the stereotype about girls. Although I was a guy, at least outwardly, until a year ago, I think I was always inwardly a girl. According to the stereotype, we girls are supposed to be indifferent to anything more technical than the designer cov... Read full Story
shemale lover 2012-01-20 4,685 femdom erotic encounters consensual
80%
Femme Fatale
Derek sighed heavily, his eyes scanning the bank of security monitors, each of which showed a different view of Femme Fatale. A month ago, he'd taken the job as a security guard for the woman's clothing store because he needed the money and because he supposed that watching the store - or, more spec... Read full Story
shemale lover 2011-11-18 3,204 hardcore cum shemale sex
100%
The Greatest Lie Part 4
Don’t get me wrong, I don’t hate being around people. Actually, I hate being alone: it brings out the weird self-critic inside me. But god, do I hate crowds. Fall registration brought mobs to the campus. The half-empty dormitory that I had shared with a few Asian engineering students was... Read full Story
shemale lover 2012-01-19 4,614 taboo femdom crossdressing
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 4,409 shemales taboo Fetish
50%
The Greatest Lie Part 15
I think that if you could get honest answers, a lot of heterosexual guys would probably admit to having had at least a passing desire to be a girl. If they were honest, they would probably admit they thought of it "when I first noticed a girl's breasts" or "when I first felt a girl or... Read full Story
shemale lover 2012-01-20 6,084 anal hardcore erotic encounters fantastic
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 3,331 shemales Fetish jerking off tgirls
66%
Dirty Business Trip
Chapter 1: The Transsexual Hotel Encounter "Yes, I am checking in," I said, putting my credit card on the desk. The woman behind the desk took the card and looked at the name. She was about 5 feet 10 inches tall with dark black hair and brown eyes. Her skin was beautifully tanned and he... Read full Story
shemale lover 2012-09-26 12,707 Group Sex Cumshot shemale oral
75%
Aunt trip
In 2013, after almost three years of service in Afghanistan, George Madsen, a gay Royal Navy communications petty officer, retired. His experience in the distant deserts had left an indelible mark, the memories of friends lost and challenges faced still burned vividly in his mind. Coming home was n... Read full Story
Rebba 2024-04-25 2,301 Shemale Fucks Guy Blowjob Big Cock Ladyboy Guy Fucks Shemale shemale fucks shemale Fantasy Tale
25%
How To Spot A Shemale
More and more men are taking female hormones, receiving breast implants, and undergoing sex-change operations to become "women." Some start these procedures while they're still teens and more than a few mimic women so well that they can use the ladies' room without raising an eyebrow among... Read full Story
shemale lover 2011-08-18 4,394 shemales transsexuals essays
50%
Trying It On For Size
I was twenty minutes early for my one o'clock appointment so I found a shady spot in the parking lot of the upscale chain motel, kept the engine running to power the air-conditioner on the warm Sunday afternoon, took a few deep breaths and tried to relax. My mind wondered back over the series of eve... Read full Story
shemale lover 2011-10-26 7,774 asshole licking sucking
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 7,218 asshole shemale oral
50%
The Greatest Lie Part 5
Most of my classmates celebrated the first Saturday after the beginning of classes in hedonistic leisure, nursing hangovers and playing Frisbee on the Quad. But I spent the morning plotting my escape from this dangerous, macho dormitory, studying want ads and making appointments to look at studios o... Read full Story
shemale lover 2012-01-19 3,679 hardcore erotic encounters fantastic
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 3,741 hardcore erotic encounters fantastic
50%
The Greatest Lie Part 11
"En Francais", they say "plus ca change, plus c'est la meme chose:" the more things change, the more they stay the same. When Tran and I got back to Minneapolis from our trip to Thailand for our sex change operations, it was every bit as dark, frigid and depressing as it had been... Read full Story
shemale lover 2012-01-20 5,108 cum transformation erotic encounters
50%
The Greatest Lie Part 18
They say that prostitution is the oldest profession. I disagree. Some guy must have been a professional hunter to have gotten together the spare change to pay for that first commercial fuck. It's like that chicken and egg conundrum. Eggs definitely came first. Just as mutation precedes evolution, th... Read full Story
shemale lover 2012-01-20 4,107 taboo hardcore femdom
100%
Bend That Gender
Shannon's Shocking Discovery Shannon leaned against Marilyn. She was definitely light-headed from her last drink. Marilyn's hand resting on her left hip pulled her closer, a move at once comforting and unsettling. She slid her arm around her new friend's waist, resting her head on the silk covere... Read full Story
shemale lover 2012-04-27 6,825 orgasm oral sex cum swallowing
0%
The Shemale As A Figure in Art
The writer of shemale erotic fiction is doubly blessed-and doubly cursed-because he or she has to describe the best of both worlds: both female faces, breasts, legs, buttocks, and anus and penis, testicles, and scrotum. Although, overall, his or her protagonist must be not only feminine but, usu... Read full Story
shemale lover 2011-08-30 3,327 penis scrotum anus
100%
Sanctuary
Old habits die hard. Jamie Lee was reminded of the truth of that aphorism the day that she forgot to use the ladies room. As a transsexual who’d undergone counseling and was presently taking daily doses of estrogen both to repress her testosterone and to maintain her breasts, softened skin, fu... Read full Story
shemale lover 2012-01-12 2,702 hardcore shemale pissing
100%
A Mate's Trans Date
I had been seeing Nikki for about 6months and taking her out as you would any girlfriend, sharing our groups of friends socially of course. One evening we went to a friends place and when Nikki has snoozed off to sleep on the sofa me and my mate called Al got talking, we had been drinking most of th... Read full Story
shemale lover 2012-03-19 4,515 first time Stockings anal sex oral sex
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 4,680 Stockings Big Tits Creampie Lingerie Guy Fucks Shemale Mature
85%
Unforgettable First Time
I am in my late thirties and have known for a while that I have a sexy body. I'm 5'11", slim and athletic with little cherry butt and shapely legs. A lot of women have told me my body is sexy. A few men have mentioned it too. Sometimes I get photo-snapped at the pool or the beach. I've been luc... Read full Story
shemale lover 2016-05-06 10,038 cum oral deepthroating
50%
Shemale Art and Artists
Several erotic artists specialize in comic books, cartoons, or illustrations that feature buxom hermaphroditic, pre-operative transsexual (shemale), or t-girl characters. Such shemale art ranges in style from three-dimensional, computer-generated images and anime, hentai, or manga comic book-style s... Read full Story
shemale lover 2011-09-22 3,687 shemales essays romance
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 3,296 anal sex asshole cum deep penetration
50%
and Daisies and Lollypops
One of the most intriguing television phenomenons of the past 10 years has been The Jerry Springer Show. From trash talking prostitutes to mother-daughter love affairs, the most shocking underbelly of American culture has been exposed to those who would never suspect. One of the recurring themes tha... Read full Story
shemale lover 2011-10-24 2,916 Fetish transsexuals lesbians
85%
The New Hire
Norman Bancroft wasn't exactly crazy about the job. For one thing, the pay sucked, and there was zero chance for promotions. In addition, fairly long periods of boredom were relieved-if one could call driving several hundred miles per day for several days in a row relief-by trips from one of the rai... Read full Story
shemale lover 2011-10-27 4,193 anal hardcore oral
0%
The Greatest Lie Part 19
The booked me as Alex Rios and handed me an orange jump suit and slip-on boots. I changed in a tiny curtained alcove and relinquished my clothes, shoes and purse, and became Inmate 265743. The booking clerk ignored my pleading eyes, so I begged. "You can't put me into a male population. I... Read full Story
shemale lover 2012-01-21 4,721 hardcore femdom erotic encounters
100%
Trannie in Training
Caught Again Things have been great since I started my new job and secret life as a crossdresser. I have had a lot of experience dressing and actually passing on the street as a woman. Actually a very sexy woman at that. The visits from my supervisor were always memorable and he has taught me ... Read full Story
shemale lover 2012-02-02 2,602 Fetish oral crossdressing
100%
Ellen's Candy
Sometimes I get in the mood to suck a dick but I’ve never considered myself gay. I’m @ the very least bisexual but I don’t like to limit myself to that either because I think it restricts my sexuality. I get turned on watching all types of sexual situations that you could think of;... Read full Story
shemale lover 2012-04-02 5,099 Cumshot condom sex
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 4,477 Cumshot shemale cum swallowing mouth fucking rimjob
80%
Bisexual Black Man's Paradise
The name is T.J. Brown. I'm an engineer working at Walpole, the toughest correctional facility in the state of Massachusetts. My days are spent reading books, exercising and occasionally tussling with other workers. The facility is undergoing some expansion and I'm the lead engineer on this gig, wor... Read full Story
shemale lover 2012-06-24 5,287 big dick tranny anal sex Cumshot orgy facial oral sex
88%
Black Transsexuals
Whenever I'm off duty, I'm liable to get into some type of adventure. Who am I? I am Troy Shane, a sergeant with the Massachusetts State Police. I was walking around the Boston Public Library when I saw this tall, plump jet-black honey with a big butt. She was walking around strutting her stuff. A B... Read full Story
shemale lover 2012-07-14 3,888 anal tranny cum oral black
100%
Black Transsexuals Rock Chapter 2
Hello, there. My name is Sarina Jean. I'm a big and tall, busty and big-bottomed Black Transsexual of Haitian descent living in the City of Ottawa, Ontario. People say I remind them of Hollywood Superstar Queen Latifah, only taller and with a much bigger ass. I'm a Business Administration major at C... Read full Story
shemale lover 2012-07-17 2,453 jerking oral sex assfucking
50%
Butterflies
There were a lot of good reasons to be out this early, but none as wonderful as seeing this first Giant Swallowtail awakening, and John smiled as it moved. Magnificent, he whispered, in awe of this giant as it slowly unfurled it's Forewings against the sun's morning warmth. It was, as they always we... Read full Story
shemale lover 2012-09-30 5,656 taboo transformation sex
100%
Dream Lovers
Chapter 01 (edited) An Accidental meeting Doctor Matt Dillon treated scores of accident victims coming thru the Emergency Room. Cool under pressure, quick and aggressive, his record of successful treatment is impressive. His natural caring heart constantly battled the cool detachment necessary... Read full Story
shemale lover 2012-11-15 3,230 shemale oral orgasm
100%
Dressed for Disaster: The Sequel
Patrick Summers wandered the streets of lower Manhattan in an aimless fog, the chaos surrounding him a lurid backdrop for the turmoil between his ears. He had just suffered two tremendous shocks: his narrow escape from the collapse of the World Trade Center, and his unmasking as a crossdresser on te... Read full Story
shemale lover 2012-11-21 2,854 Fetish crossdressing wig
50%
The Greatest Lie Part 6
In my rare moments of leisure in the weeks following my close encounter with death, I had had little opportunity to talk about it. Of course, the police had asked perfunctory questions, and I had testified at the coroner’s inquest, but until my next appointment with Dr. Erika Wright, I had not... Read full Story
shemale lover 2012-01-19 4,444 hardcore erotic encounters fantastic
100%
Danielle's First Time
Danielle was born in the winter to 1976, but she was born a male by the name of Daniel. Daniel looked like a normal male child aside from liking girly things. Whenever Daniel would play dress-up he'd always dress in his mother's or his aunt's clothes and his parents thought that was cute until Danie... Read full Story
shemale lover 2012-02-03 5,393 cum dildo fingering
100%
White Mistress & Black Male Slave
Right now, I'm staring into the eyes of my favorite person in the world, a sexy black man named Pierre D'Arnaut, as I slam my member up his tight ass. For I am a sadistic biracial transsexual with dominatrix tendencies who can't get off any other way. My name is Claudia Fils-Aime and I heartily auth... Read full Story
shemale lover 2012-11-21 5,265 Creampie domination Interracial
100%
Exposure, Disclosure
The Greatest Liar, Exposure, Disclosure © Alexandra Rios 2019 Author’s Note: This is a continuation of the narrative which commenced with “My Awkward Phase”, which I posted here previously. Readers may wish to read that before continuing, although I have written them to stand alone. Natives s... Read full Story
the greatest liar 2019-06-18 7,448 Teen (18+) Small Tits Amateur Group Sex Latina Blowjob gangbang Guy Fucks Shemale cum in mouth
94%
Deep Throating Shemale
Yvonne is one of my best friends and we do more than just hang out at the local nightclub. She has long wavy black hair and dark violet eyes. Like me, she is also a pre-op transsexual, which means she has breasts and a penis. In the few years that we have known each other, she has taught me a lot ab... Read full Story
shemale lover 2015-05-29 6,248 cock sucking shemale
0%
Looking-Glass Ladyboy
I was taking a walk to stay--all right; I'll admit it--to get in shape, when I saw the "Going Out of Business" sign in the second-hand furniture store a block north of my condo. I wasn't in the market for anything, new or used, but I can't resist a bargain, and what was better for finding ... Read full Story
shemale lover 2011-10-29 7,511 asshole Fetish Ladyboy
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 3,122 hardcore erotica romance
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 2,834 Cumshot ass fucking deep penetration
100%
The Greatest Lie Part 12
My Own Worst Enemy Let’s face facts. The so-called the "War On Drugs," "Just Say No," and all the other anti-drug campaigns are complete failures because they ignore reality: getting high is fun. College students drink and take drugs to break a boring routine; the poo... Read full Story
shemale lover 2012-01-20 4,207 hardcore crossdressing fantastic bondage and discipline
100%
A Brand New Year
He stood in the center of the party drinking from a bottle of Coors Light. He wore a black t-shirt and pair of faded gray jeans and converse sneakers along with a Flyers cap hat and had a go-T. 25 year old Mike had been invited to this new years party by his best friend Danny who he had known since ... Read full Story
shemale lover 2012-02-08 4,270 Creampie oral sex Guy Fucks Shemale 69 pose
100%
A Love Story
The bisexual lifestyle can be a lot of fun. Let no one tell you otherwise. My name is Lawrence Henderson and I'm a six-foot-tall, good-looking black man living in the town of Boston, Massachusetts. I work as an executive at Anderson & Winston on Boston's Financial District, one of the top invest... Read full Story
shemale lover 2012-03-18 2,771 tranny brunette bisexual
81%
A LadyBoy For My Wife
I have been happily married to my sexy Thai wife Lisa for three years now. My wife is Thai is petite (5'1") with a stunning figure, a tight ass and long waist length black hair. We had met in a bar in Thailand and subsequently we were married back here in the UK. She was very loving with m... Read full Story
shemale lover 2012-06-23 10,566 Group Sex Masturbation shemale Ebony facial
50%
Black Transsexuals Rock
Yvette Seraphim is the name. I'm a big and tall, dark-skinned and big-bottomed young Black woman of Haitian descent living in the City of Ottawa, Province of Ontario. People often say I resemble Tennis Champion Serena Williams, only taller and curvier, with more booty. I take that as a compliment. I... Read full Story
shemale lover 2012-07-17 3,413 tranny anal sex Cumshot Ebony fingering oral sex