Sort by
Relevancy

Free Stories

72%
ACROSS THE STREET AND TWO DOORS DOWN by Spanky de Bautumn
Jamie knew he was different. He didn’t fit in with the other boys, but he didn’t feel like he fit in with the girls either, he just knew he was different. He wasn’t into dolls or balls. He was the smallest boy in his class and more than half the girls outweighed him. But the one thing he had going f... Read full Story
SpankydeBautumn 2021-01-29 11,897 Teen (18+) Small Tits Crossdresser Fetish Blowjob Lingerie Guy Fucks Shemale cum in mouth
100%
Hung Trans Lesbians Fuck Two Ladyboys
Note 1: If you like Transsexuals, Trans Lesbians, Asian Ladyboys, Big Cocks, Extreme Cock Sucking, Anal Fucking, Anal Fisting, Semen Swallowing, Role Play, Orgies, BDSM, Cock Sounding and Foot Fetish this story is for you. Note 2: All the characters are over 21. The names are fictitious, but some... Read full Story
darrell 2022-01-03 4,952 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
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 9,472 Small Tits Amateur Cumshot Masturbation Creampie Shemale Fucks Guy Blowjob blonde Lingerie Guy Fucks Shemale Homemade pov cum in mouth
90%
Camming Down the Rabbit Hole Ch. 08
A familiar sensation greeted me as my eyes opened and a yawn escaped my mouth, that oh so delicious feeling of my morning wood straining against my silk night ware. It was becoming an ever occurring pattern that no matter how large the orgasm the night before I would wake with the hardest of cocks, ... Read full Story
Dani_does_Dallas 2021-11-15 4,367 Stockings Small Tits Crossdresser Amateur Cumshot Masturbation Fetish Uniform Lingerie Homemade self sucking pov cum in mouth
100%
Camming Down the Rabbit Hole Ch. 07
Opening my eyes I struggled a little as the residual cum on my face from last night’s show hadn’t been fully wiped off, I felt the dry and crusty leftovers crinkle on my skin, but couldn’t help but smile to myself as I remembered how it had got there. The intensity of that orgasm had been on another... Read full Story
Dani_does_Dallas 2021-10-22 6,791 Stockings Small Tits Crossdresser Amateur Cumshot Masturbation Fetish Lingerie Sex Toys Homemade self sucking pov cum in mouth
95%
First time
Hi, my name is Sandra. In fact, I'm not exactly a girl, but a CD. Even as a child, I felt different and I used every opportunity when I was left alone in the apartment to dress up, to put on women's clothes, to put on make-up. In time, I started watching porn, as did all my friends. But, unlike them... Read full Story
cd Sandra 2021-10-13 6,172 Stockings Teen (18+) Small Tits Crossdresser blonde Guy Fucks Shemale
80%
Karen, My School Teacher Part 1
The Meet By FoxyHosed It all started when we got a new class teacher. Her name was Karen. She was a mature lady and had dark red hair to her shoulders. That first day she wore some short dark blue jeans and a brown blouse. My other classmates started whispering about her. “He-he! Have you seen t... Read full Story
FoxyHosed 2021-01-29 9,458 Crossdresser Fetish redhead pantyhose Mature pantyhose cd
85%
My Awkward Phase
My Awkward Phase ©Alexandra Rios 2019 The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne ... Read full Story
the greatest liar 2019-06-14 12,500 Small Tits anal sex Latina Masturbation Bareback Creampie Blowjob Big Cock transformation gangbang Shemale and Girl Guy Fucks Shemale Sex Toys Ass to Mouth cosplay hormones high school real life situations
100%
Sissy Boy’s Secret Desire – Part 5
The relentless rhythm of her thrusts left him gasping for air, his body trembling uncontrollably beneath her. His mind was drowning in a sea of pure, raw sensation—each brutal movement sending shockwaves of pleasure mixed with pain through him. He couldn’t stop himself from crying out, the sounds of... Read full Story
shemale_club 2024-10-03 1,464 Stockings Small Tits Crossdresser Fetish Ladyboy Uniform domination pantyhose Sex Toys sissy femboy teen (18+)
100%
TO BE OR NOT TO BE – PART 2
TO BE OR NOT TO BE – PART 2 by Spanky de Bautumn Part 1. Sunny, Mel, and Shari learn they are going to New York to perform a play off Broadway and are really excited about it. Being a small troupe, we unseen members had to wear many hats. Unfortunately, there was just the two of us, Joe Donn... Read full Story
SpankydeBautumn 2021-02-22 4,146 Small Tits Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
100%
TO BE OR NOT TO BE - PART 4
TO BE OR NOT TO BE - PART 4 by Spanky de Bautumn Part 3. Everybody was working hard for opening night when tragedy strikes and Sunny has to make a decision. Walking back to the hotel, I was lost in thought. I was excited but at the same time scared to death, confused and clear of mind, think... Read full Story
SpankydeBautumn 2021-02-23 2,905 Small Tits Crossdresser Outdoor Fetish Lingerie Mature pov
100%
SissY Piss faggot Facts Lena Scarlett sissy
Well, hi :) I just want to let you know that I won't post stuff here chronologically as I wanted :) HARD WORK xD Instead I will post all the quick thoughts about me and my sissy faggot experiences, OK? Now, today I just wanted to say that I've just realised that I'm beggining to like stuf... Read full Story
Lena Scarlett 2024-11-06 3,107 Small Tits Crossdresser Fetish Uniform Guy Fucks Shemale Sex Toys sissy piss Solo Shemale Compilation Ass to Mouth teen (18+)
92%
My Seductive Secret (True Story)
During my childhood, me and my brother used to play with two other boys who were our neighbors every weekend. One day we decided to wrestle, and I took on the youngest one, (he was about 2 years younger than me, like my brother) and we wrestled in the shed while my bro and his bro (who was my age) w... Read full Story
LovelyLeo97 2019-06-18 14,665 Stockings Teen (18+) Small Tits Crossdresser Cumshot Outdoor Masturbation Bareback Fetish Blowjob Big Cock Lingerie domination Sex Toys Homemade cum in mouth
100%
Camming Down the Rabbit Hole Ch. 12
We woke up many hours later, still intertwined, my morning wood throbbing as Ellie slid inside my panties and wrapped her hand around it. This was a much better way to wake up than usual, and we proceeded to have a really relaxed slow fuck. She reached a much more low key orgasm but I knew I wouldn’... Read full Story
Dani_does_Dallas 2022-05-09 5,847 Crossdresser solo Amateur Cumshot Outdoor Masturbation Blowjob Shemale and Girl Sex Toys self sucking pov cum in mouth webcams
85%
BANGING AROUND BANGKOK
BANGING AROUND BANGKOK: THE AMOROUS ADVENTURES OF CAITLIN "MEOW" MORRISON after living and working in Thailand/SE Asia for many years i decided to write an erotic story based on some of the people i have known, venues and places i have been, and the P4P night-scene where i spent way too much... Read full Story
bkkldby 2019-06-17 14,736 first time Teen (18+) Amateur Group Sex Big Tits Cumshot Outdoor Bareback Blowjob Big Cock Asian lesbian public place
100%
Camming down the rabbit hole Ch1
Back in January 2020 I guess I was lucky, I did have a regular job although the pay was miserable and I did have my own place. On my wage all I could afford was a miserable bedsit in a neglected part of town, but on the upside I didn’t have to flat share and it worked well enough for me. The west... Read full Story
Dani_does_Dallas 2021-08-11 5,881 Crossdresser solo Amateur Masturbation Lingerie Homemade webcams
100%
A Perfect Pandemic: A Transsexual Transition in a Troubled Time
A Perfect Pandemic A Transsexual Transition in a Troubled Time A Novelette by Alexandra Rios Text Copyright Reserved © August, 2021 Dedication Transgender Day of Remembrance is a solemn occasion. I am offering “A Perfect Pandemic” for free as an antidote to the fear, phobia, discrimination, d... Read full Story
the greatest liar 2021-11-16 6,610 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
100%
The Mole
Police work is a paramilitary occupation. Uniforms, rank, weapons, discipline…It can be exciting and interesting for some and boring for others. Some officers seem to find lots of action during their career (or maybe it finds them) while others never use their sidearm except for target practi... Read full Story
shemale lover 2012-01-26 6,984 brunette Crossdresser Fetish
50%
An alumni gathering like no other; 2/2
... I opened my eyes, sobered up from the alcohol and my lust. Simo had already left. I had to get ready for the party, and I had to do it like a man! BUT, slut that I am, to make my breasts more prominent under my dark purple tank top, I tightened a transparent strap around my waist. You never kno... Read full Story
hippocampus_171 2024-06-16 2,897 anal Amateur Creampie Blowjob Sex Toys Mature small cock big ass cum in mouth
100%
Camming Down the Rabbit Hole Ch. 09
As per my previous mornings recently, I stirred and rubbed the sleep from my eyes, that delicious feeling of my silk night ware stretching over my taught nipples and my morning wood throbbing in its lace enclosure. The urge to touch myself was palpable, it seemed no matter how hard I came the night ... Read full Story
Dani_does_Dallas 2022-03-22 4,009 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking pov cum in mouth webcams
100%
Camming Down the Rabbit Hole Ch. 10
As the sun beamed in through a gap in the curtains my now familiar morning wood strained at the silk of my nightwear. How was it that no matter how hard I came the night before it would wake up eager and ready to go. As had become customary my mind would be filled with the events of the previous nig... Read full Story
Dani_does_Dallas 2022-04-12 3,984 Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking cum in mouth webcams
50%
A Murder Misstery
When I rolled out of bed that fateful morning, I had no way of knowing that it would be my last day as Matt McCoy. After showering and dressing quickly (how I long for those days!) I bolted out the door for my train, looking forward to another manic day on the floor. Although I was one of the younge... Read full Story
shemale lover 2012-03-20 5,414 Fetish crossdressing feminization
85%
Whores and Pimps - Part I
Malcolm was a middle manager in a small business in a large city. Malcolm led a pretty boring life; he in his forties, single, devoted to his work, he liked to keep himself fit, all of his family lived interstate except for his older sister who lived nearby, and he led a quiet social life. Malcolm h... Read full Story
shemale lover 2012-05-13 8,569 Stockings Crossdresser Cumshot Fetish oral sex pantyhose
100%
Camming Down the Rabbit Hole Ch. 11
I sat there for some time, my phone still in hand. I couldn’t fully comprehend the situation and where I was. All this started when I was put on furlough and thought I would be losing my job, an idea born out of boredom, hornieness and desperation. What started as a regular cam show with a guy hopin... Read full Story
Dani_does_Dallas 2022-04-25 4,704 Crossdresser Amateur Cumshot Masturbation Blowjob Uniform Lingerie Shemale and Girl Sex Toys Homemade self sucking pov cum in mouth
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 4,805 taboo Fetish crossdressing
100%
From accidental trans porn addiction to a cum filled booty
One night when I was around 30 or so I was watching some porn, nothing unusual for a guy like me, aka a sex addict. Sex addiction is great if you’re Tiger Woods and swimming in poon, but for guys like me - regular, awkward, slightly handsome in a very boyish way, weirdos — it’s not that fun. We... Read full Story
CDJaneBooty 2022-04-01 10,931 first time Crossdresser Amateur Cumshot Bareback Creampie Blowjob Big Cock gay Homemade Ass to Mouth curious first time with a man
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 5,322 Stockings Big Tits Creampie Lingerie Guy Fucks Shemale Mature
100%
Betrayed Chapter 8
Did I happen to mention everything was moving so fast? People weren't really surprised Lance Layton took his commission and ran for the door as fast as he could. There wasn't an employee in the firm who didn't wish they could produce the same results for themselves. The rumors ran rampant: he had pu... Read full Story
shemale lover 2012-05-30 4,088 pussy Fetish crossdressing
88%
Robbed And
I was in the ensuite off the bathroom applying the last of my make-up to complete my transformation from Martin to ‘Michele’ when I heard the disturbance. My wife Kerry was waiting for me in the bedroom nursing a gin and tonic. We had just returned from a boring party and I had convinced... Read full Story
shemale lover 2012-04-23 8,631 Creampie Fetish crossdressing nylon
100%
Tight Spot
XtinaSmith2017 Cody bit his lip as he looked over towards the shop, a little anxious about their planned endeavor but not wanting to come off as uncool to his friends, "Are you sure this is a good idea?" he asked. His friends grinned and laughed, playfully nudging him as they made their way ... Read full Story
Gwapo67 2022-07-22 6,386 Big Tits Bareback Creampie Shemale Fucks Guy Fetish Blowjob Big Cock Lingerie domination cum in mouth
66%
Your Waitresses
You begin your evening by taking a long luxurious bubble bath followed by taking the time to apply your makeup at a beautiful white makeup table and mirror from the 1920's. You then slide a sheer pair of black stockings up each leg and attach them to your black and red lace garter belt. You then run... Read full Story
shemale lover 2012-08-10 4,113 Fetish cum crossdressing
100%
The Biology of Music - I fucked my trans substitute teacher
I was never strong in school. I wasn't very interested in what we were being taught, and the teachers liked me enough to not give me too hard a time about it. I attended an all boys school. It was actually quite a religious school which makes this story all the more surprising. I was in the middle c... Read full Story
terrifictim 2022-01-03 4,358 Creampie Guy Fucks Shemale feet licking first time with a tranny teacher student
100%
Shemale Fantasy - Suck Fest
This story is completely fictional - in fact it is a fantasy of mine that I will describe in great detail, contact details are at the bottom if you want to make this a reality! I arrive at your house on the evening. You let me in and show me to the spare bedroom. I walk in and close the door behi... Read full Story
shemale lover 2011-09-13 5,728 Cumshot jerking off pantyhose
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 5,651 Fetish trans tv
100%
A Downtown Moment
I had reason to head downtown for a meeting with some industry colleagues and after my meeting I dropped in to see a friend of mine who I used to work with. Loretta and I worked together for about a year on similar project as contract workers, I moved on to other things and she stayed with the compa... Read full Story
shemale lover 2012-02-28 5,270 pantyhose mistress
60%
Brotherly Love, Sisterly Love Chapter 2
"RACHEL" My twin sister, and sometime brother, and I had been experimenting sexually with each other and crossdressing together for around a month, growing to love and to perfect our new feminine personas until they became the ones we thought of as our true selves. Whenever our parents ... Read full Story
shemale lover 2012-09-28 7,008 Cumshot Fetish oral sex cum swallowing
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 3,358 Stockings Bareback Fetish transsexual Lingerie Sex Toys travesti Vintage rosebud plug gonflable gode xxl
57%
Ambers torment
It seem to be the typical day for Amber as she entered the home of Master. The usual early wake up and long drive down to his house seemed nearly routine though, the last visit was a few months past and the girl was anxious for what was to come. Although, her expectations were not different from any... Read full Story
shemale lover 2014-04-19 7,763 shemales Fetish bdsm
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 8,751 Fetish transformation dildo
87%
A Picture Perfect Sissy
"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie." Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if what he was doing was okay. He really wanted wh... Read full Story
shemale lover 2012-05-27 11,228 Stockings anal sex Fetish Interracial sissy
100%
Woman Cross Dresses for Power & Sex
Tucked in the far corner of a dark, dancehall parking lot, Sarah, also known as Robert, was having sex in a car with Joseph, also known as Josephine. Having sex in a car was no big deal. A lot of couples have sex in cars. Yet, if a passerby could see through the steamy windows, a sight to behold, ev... Read full Story
shemale lover 2012-10-09 4,432 sucking Fetish fingering crossdressing
100%
Sweet Encore
I was alone tonight and feeling just a bit paranoid as I listened to the soft music. The soothing sounds put me in a seductive mood, but It seemed that all my lovers were too busy for me, or they had other plans. Uncle Barney and my detective were probably home being dutiful husbands. Bo was under h... Read full Story
Regina10 2024-05-09 3,849 Crossdresser Big Tits Bareback Creampie Blowjob blonde Big Cock Guy Fucks Shemale big ass Ass to Mouth
87%
The Hotel Part 1
I knew when this started it would be like nothing I had ever done before. I drove up to the hotel early friday morning. I was checking in for seven days. Seven Days of non stop pounding of my asshole, Strapons, Crossdressing, fucked fem, huge dildos, and giant buttplugs are just a few of my fetishe... Read full Story
shemale lover 2012-02-11 6,476 Fetish cum domination Sex Toys
100%
Lady in the House
How had it come to this? I was dressed as a woman and standing in the far corner of a darkened cell on E Block of Chelmsford Correction Facility for Men, and waiting for the most dangerous inmate in the jail. How had a mild mannered, and diminutive but highly successful accountant in his 30s ended u... Read full Story
shemale lover 2012-05-12 4,360 Stockings Fetish crossdressing
80%
Becoming Alanna Part 2
Walking into room number one, she told me kindly to strip nude and climb into the chair. I did as I was told and hopped in to the chair. I fit my feet and legs into the stirrups and she spread them apart exposing my cock balls and asshole. She looked me up and down and smiled "not much work wit... Read full Story
shemale lover 2012-07-12 4,215 sucking Fetish Ladyboy rimjob
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 3,253 Fetish crossdressing wig
92%
Lady In The House Chapter. 01
A story by MicheleNylons ( Man in jail is transformed to prison slut.) How had it come to this? I was dressed as a woman and standing in the far corner of a darkened cell on E Block of Chelmsford Correction Facility for Men, and waiting for the most dangerous inmate in the jail. How had a mild... Read full Story
✘Transensual✘ 2019-01-11 9,935 Crossdresser Bareback Creampie Fetish blonde Big Cock Lingerie domination Guy Fucks Shemale transvestite slut PRISON FUCKBOY prison sex Prison Bitch
75%
Kidnapped (Adult Fiction)
Kidnapped I remember being normal. I was a young man in my 20's living in my parent's house struggling to get by. I was online more than I probably should have, but it was an escape from the harsh reality of my life. I didn't feel fulfilled or like a success, I felt like a failure on many differe... Read full Story
Vennom 2019-06-17 25,381 Fetish transformation fiction pov mind control drug interaction mind mindfuck change
100%
First Time I Experienced Eating a Tgirl Out
So this is likely going to seem tabboo for some and if this is not your thing, I respect that but everyone is different. Eating pussy came natural to me like it does for most guys once they start having sex with girls. Other than one time 69ing with a female and having what I would call "incidental ... Read full Story
AllenB 2022-10-21 5,657 Amateur Big Tits Cumshot Latina Creampie Fetish Blowjob rimming Homemade cum in mouth latina ts
100%
Daddys Little Slut
I have been living with my dad for the last year after my mum who is Indian, found out that I was doing lots of drugs, and that I was bi and also a cross dresser. We never talked about it as for me, the cross dressing was on and off and usually when i was high. When i turned 25, I tried meth, and fo... Read full Story
aishacox 2023-01-31 5,956 Crossdresser Cumshot Fetish Blowjob Latex
100%
Headmistress' Favorite Sport Part 10
When Denise came to she was lying in bed. She had been washed and she could no longer feel the annoying diaper rash. In fact she felt fine, clean and well rested. On her feet were what turned out to be black Oxfords with seven-inch heels. Her ankles were in steel cuffs and connected by a eight-inch ... Read full Story
shemale lover 2011-12-13 4,994 torture toys bondage and discipline chastity belt
100%
The WearFemme
The times between his fantasies have begun to shorten and he knew it wouldn't be long now. One chance glance at an outline in gym shorts as a guys walking in the wind, or seeing a girl with similar features wearing revealing clothing. The thought of it is almost overwhelming now and he has to focus ... Read full Story
Jayde Love 2022-12-01 3,932 Small Tits Crossdresser solo Amateur Outdoor Masturbation Fetish Homemade pov
100%
I was backstage giving blowjobs at a transsexual beauty pageant
I was backstage giving blowjobs at a transsexual beauty pageant I had this neighbor, who cross-dressers on weekends for a LGBT club. She invited me to an annual transsexual beauty pageant. Beautiful slutty shemales competing to be the official beauty queen for the club. She happens to be hosti... Read full Story
My Shemale Attraction 2024-08-07 4,452 Crossdresser Group Sex Big Tits Cumshot Blowjob blonde Big Cock Ebony gangbang domination pantyhose
75%
A Woman's Wager
A man who lost a bet must dress as a woman and discovers he likes it. "Pardon me, Madam," said Ed trying to hustle his shopping cart down the aisle by a very large woman. With her carriage blocking one side of the aisle, she was hunched over a shelf with her big ass blocking the other s... Read full Story
shemale lover 2012-07-28 3,691 Fetish transvestite crossdressing
100%
Yellow Polka Dot Bikini(s)
"She was afraid to come out of the locker. She was as nervous as she could be. She was afraid to come out of the locker. She was afraid that somebody would see. Two, three, four, tell the people what she wore. It was an itsy, bitsy, teenie, weenie, yellow polka-dot bikini that she wore for the ... Read full Story
shemale lover 2012-08-22 4,167 Fetish bikini crossdressing sissy
100%
Sissy Boy’s Secret Desire || Part 4
The sensation was overwhelming—his body writhed beneath her as she took him deeper with each thrust, pushing him beyond anything he'd ever imagined. The strap-on filled him completely, stretching him, making him gasp for air. Each movement sent ripples of pleasure coursing through him, blending with... Read full Story
shemale_club 2024-10-01 1,407 Stockings Small Tits Crossdresser Ladyboy Uniform domination pantyhose Sex Toys sissy femboy teen (18+)