Sort by
Relevancy

Free Stories

81%
First time with ladyboy / bottom
Hi everyone! now it is my turn to share my experience in Thailand. We were on a Christmas vacation on an island, and I didn’t even know ladyboy existed then. At a Christmas beach party I chatted and danced with a woman and we ended up in my bungalow. We kissed a lot and I knew that now I was g... Read full Story
FoxyLover'ts 2020-10-06 15,739 Cumshot Blowjob Big Cock domination Interracial Homemade cum in mouth ladyboy ts thailand ladyboy shemale fuck guys virgin ass bottom boy bottom virgin
100%
Joe gets to the bottom of things
She kept it tucked away, uncomfortable, squeezed between her legs held in place by the tight rubbery panties that really weren't her style, but they punctuated the "surprise". Joe was aroused by her femininity, as she slipped off the spaghetti straps of her little white dress revealing the... Read full Story
keeponst 2012-10-08 2,737 sucking Ladyboy virgin
100%
I Love To Love You
I Love To Love You Baby By Sabrina G. Langton Author's note: I have published this story on two other sites. I always said it was slightly aurobiographical, but reading it back it is a pretty accurate account of my summer of '88. There are only 3 things that I changed. 2 are itsy bitsy tiny deta... Read full Story
Brina Giselle 2023-09-24 4,720 anal Crossdresser Blowjob kissing transgender virgin romantic earrings
100%
Shemale Solo Tube And Practical Jokes
"Dude, you know I mean you good", my friend John was saying while he was dragging me out of bed, "You're spending way too much time inside and I have a treat for you!" I hated John's surprised - he had all sorts of crazy, stupid ideas, like painting my dorm room in black while... Read full Story
shemale lover 2016-02-22 3,518 tranny tit fucking
92%
My Brother's Panties
My brother and I are twins, fraternal not identical. Throughout our lives, no one ever confused us, and furthermore, no one ever thought we were siblings. Growing up I would often get the question, "Kevin, why do you hang out with Jamie so much?" People were always surprised when they lear... Read full Story
shemale lover 2013-01-12 13,476 solo sucking jerking Sex Toys swallowing
100%
Continua mi mundo Tv
Como les decía a mis 20 años ya era otro mundo, ya compraba mi propia ropa intima femenina mas que todo ropita muy chica, pues siempre he sido muy delgad@, a esta edad aun era virgen pero con hombres ya que aproximadamente a los 17 le robe un consolador a una tía, "les admito que ha sido uno de ... Read full Story
Carla Travesti 2018-12-10 2,416 Small Tits solo Amateur Latina Masturbation Fetish Ebony Sex Toys morena flaca venezolana deportista morbosa
100%
From a 50's virgin to a Mature good for all
***Prologue - Confessions: Every day since I offered my virginity, I put myself in the shoes of a woman. The little town where I live forbids me to show myself socially. However I made myself an accomplice, my epilator who receives me after closing. Since my new beginning, male masturbations are not... Read full Story
hippocampus_171 2023-01-11 4,029 Stockings Crossdresser Amateur Group Sex threesome Big Cock domination Mature foursome Homemade cum in mouth shemale + shemale milfs
100%
Deflowered by my First Man
It is morning. Sunlight steams through the window. I wait. I feel beautiful. A soft flower to be opened gently, petal-by-petal. My scent a dawn mist over fresh primrose. You open my bedroom door and your gaze meets my own. I am dressed all in white - pure and untouched. Freshly bathed, with perfect... Read full Story
ohjaney 2019-04-01 6,957 anal Lingerie Guy Fucks Shemale virgin romantic Defloration first time with a man gentle
100%
Camming down the rabbit hole Ch6
In the morning I decided to give the running a miss and do a long session with the DVD, my legs had become a little sore and tight so some extra stretches and yoga would really help. I once again surprised myself with how much more flexible I had become, the plug still in my ass giving me occasional... Read full Story
Dani_does_Dallas 2021-10-11 4,568 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade 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 3,153 Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking cum in mouth webcams
100%
My First Blowjob
Fuck! I'm so jealous! Back in my teens I could self suck! I'd lock myself in the bathroom, lay on my back and bring my legs over top. I was able to not only get the head of my.cock in my mouth, but half of my length as well. The first time I nutted in my own mouth, I wasn't prepared for the big lo... Read full Story
Hardrock51Fifty 2024-03-26 2,370 solo Cumshot Blowjob self sucking cum in mouth teen (18+)
100%
Camming down the rabbit hole Ch4
It was the morning after the night before, and as I stretched under the bedsheets, a smile spread across my face. Remembering last night’s events, I felt myself stir a little and pressure from the panties I had on adding to the arousal. It has been a while since I had morning wood after a big show, ... Read full Story
Dani_does_Dallas 2021-09-06 3,450 Crossdresser solo Amateur Cumshot Lingerie Sex Toys Homemade pov webcams
100%
Nervous Young Man
I heard of a new gay dating app and decided to try it. It took several attempts before I could finally set up my profile but I eventually was ready to make my first contact. The instant my profile was active, at least fifty messages opened a world of choice to me. Many messages had no photo, which I... Read full Story
PetiteSlutKimberley 2023-04-07 4,580 virgin bareback sex cd slut Breeding Slut
94%
My Shemale Fantasy
Allow me to introduce myself, i’m a young European man, in my early twenties, writing my first erotic story. This has been a fantasy all my life, it probably will remain a fantasy, but that doesnt mean i cant write about it. Ever since i was old enough to realize my raising sexual interest and... Read full Story
Jakester 2013-04-10 31,278 first time Creampie Shemale Fucks Guy ass licking virgin
100%
janine 2
After my epiphany, after my fainting, after my two near consecutive, mind melting orgasms, I was ready to meet the world with new resolve. No longer would I keep my true self under wrap. I was ready to become Janine, however I was going to have to be cautious, for the time being anyway. The first th... Read full Story
bunny cat 2019-02-08 3,407 solo Masturbation Sex Toys Mature
100%
Camming down the rabbit hole Ch2
How had I ended up in this situation? Sure I was going to need to make ends meet, but I could find a normal job couldn’t I? was I this desperate? Perhaps desperate wasn’t the right word, just over a month ago I had started out camming as a bit of fun, to maybe make a few pounds while I masturbated, ... Read full Story
Dani_does_Dallas 2021-08-11 3,405 Crossdresser solo Amateur Masturbation Lingerie Homemade webcams
100%
Camming down the rabbit hole Ch3
Slowly stirring from my sleep, I stretched under the covers and a pleasant sensation spread across my torso, remembering what I was wearing when I went to bed I smiled at the caress of the fabric on my skin. It was a strangely comforting feeling, the pressure from the bra, panties and nightie felt l... Read full Story
Dani_does_Dallas 2021-08-18 4,965 Stockings Crossdresser solo Amateur Cumshot Masturbation Fetish Lingerie Sex Toys Homemade
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 4,926 Crossdresser solo Amateur Cumshot Outdoor Masturbation Blowjob Shemale and Girl Sex Toys self sucking pov cum in mouth webcams
100%
How I became addicted to my toys,
How I became addicted to my toys I tell in this story my experiences by showing how I developed my share of femininity and the toys that I use in bed to amplify my pleasures alone or as a couple. For several years now I have discreetly rented a second garage near my home to store my wigs, dres... Read full Story
sandratvtg 2022-09-20 4,503 Stockings solo Lingerie Sex Toys
66%
My girlish desires
My girlish desires, I am happy to spend my weekend at home to live my life as a woman. I apply a depilatory cream to my body, which I leave to act for a few minutes before going in the shower. I take this opportunity to do an enema to avoid unpleasant surprises during my girl games. Then, using ... Read full Story
sandratvtg 2023-01-19 3,694 Stockings solo Cumshot Creampie Fetish Big Cock Lingerie Sex Toys
71%
From Top to Bottom
I have had many encounters with shemales over the last eight years. I first discovery that such beautiful creatures existed was when I lived in Tucson, Arizona. I had gone to a adult bookstore and was in a booth watching a little porn when I came across my first Shemale porn movie. I sat back stroki... Read full Story
shemale lover 2011-09-19 7,166 first time asshole rubbing
100%
Tiffany
The first time I met Tiffany I was amazed. She was a gorgeous brunette, about five feet six inches tall, shoulder length hair, nice firm, round tits, and an ass to die for. It was late in the evening when I got off work and uncharacteristically, I decided to stop in at Varsity's for a drink. ... Read full Story
TgirlLover4Life18 2018-05-18 18,265 first time Big Cock virgin woman shecock transgirl
50%
Pati pigtails - new stepdaugter...
My biggest dream.... I live with an older couple - as their 'daughter', in a big, nice house... I come, we talk, I go to sleep. I wake up in the morning and see only girls' clothes and underwear next to my bed. High-heeled sandals, cosmetics... 'Mom' comes into the room and says: - Pati, don't loo... Read full Story
patisx 2024-04-10 1,438 couple fucks stepdad pigtails slut stepdaughter pati innocent tranny pigtails whore patisx pati sut virgin tgirl innocent pigtails
65%
Craigslist ad
You lay face down on the bed and her hands knowingly massage your body sending warm tingling feelings up and down your spine. Her hands soon also begin to massage your bottom. First one bun and then the other receives deep strokes that both relax and stimulate you at the same time. You begin to feel... Read full Story
Curious_billy 2017-03-22 4,762 virgin erotic sexy Craigslist desire
66%
Joe gets to the bottom of it
She kept it tucked away, it was uncomfortable squeezed between her legs held in place by the tight rubbery panties that really weren't her style, but they punctuated the "surprise". Joe was aroused by her femininity, as she slipped off the spaghetti straps of her little white dress reveali... Read full Story
keeponst 2012-10-04 2,936 tranny Cumshot Blowjob
33%
Bottom Kim
Kim was tied down and helpless. She was stretched out on her back on the bed, with her hands tied over her head to the headboard, and her legs secured with a spreader bar. She was blindfolded, and had a phallic ball gag in place in her mouth. The lights were low in the room, not that she could re... Read full Story
shemale lover 2012-08-13 3,284 anal sex Masturbation fingering
100%
From Virgin to Fuckslut
I had finally decided to take the plunge. I posted an online ad, saying that I had long had gay fantasies, and had finally decided to explore them. I wrote that I wasn't exactly sure what I was looking for, that I was open to suggestions and I'd never done anything with a man before. Most of the men... Read full Story
shemale lover 2012-12-03 3,973 first time oral swallowing
60%
The Creators: Book One by
Chapter One: The Life Giver BRANDON My twin sister is dead, but she’s not gone. Death is a tragedy in the remote village of Towerhead, but it’s not a rarity. Farming accidents, disease, famine, natural disasters, you name it, it kills people in Towerhead. So, six years ago, when the oxen-pul... Read full Story
sagga 2018-09-18 30,037 Teen (18+)
100%
All Hallow's Eve
I was sharing an apartment with sister just off campus and had been racking my brains for a week now, pondering what I was going to do for Halloween. It had been three years now since I followed through on a pact I had made with myself to not let my favorite holiday go by without taking full advanta... Read full Story
shemale lover 2012-10-09 5,802 caressing stroking condom sex
0%
Latex succubus
The lights of the city obscured the supposedly brilliant starlight in the night sky, leaving only dim and scattered scattered stars adorning the gloomy night sky half-covered by dark clouds, and the crescent-like crescent moon guarding it in the distance makes the night seem less empty Lonely. Mayb... Read full Story
Alicexiao 2023-01-06 3,983 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale high heel boots
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 10,728 Fetish crossdressing feminization
100%
I Give Up
The following story is the first of four parts of a tale that explores the theme of transformation. It is thematically similar others that I have submitted but has a larger narrative arc. I hope you enjoy reading the first portion, Act One & Two. I continue to work on better editing and someone h... Read full Story
ASSEaster5678 2018-09-14 8,772 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
100%
Anastasia's Life
Chapter 1: Humbling Beginnings My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember, not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barb... Read full Story
shemale lover 2012-11-26 6,941 Fetish cock sucking crossdressing
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 3,621 hardcore erotic encounters fantastic
0%
Tara's Adventures
Part 1 I had met them on line. Marla 1st then her owner Mistress Olivia. We chatted for well over a year and had met for drinks. They knew of my submissive fem side and we had planned meetings on several occasions but things always developed that upset them. Then a period of time developed whe... Read full Story
shemale lover 2012-08-11 4,998 anal Group Sex oral domination sissy
100%
A Flash of Lace
The insistent ringing of the phone broke my concentration and with great annoyance, I climbed off the bed and picked up the receiver. "Hey little brother!" My sister's sparkling voice filled my ear. "Di, Is that you?" I exclaimed happily "Got any more sisters I don'... Read full Story
shemale lover 2012-03-03 5,871 Stockings Fetish dressing
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 4,712 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
100%
Womanhood for Jenny
The muted alarm-clock brought jenny awake instantly. She reached over to shut it off. Being ever so careful not to disturb Master, she slipped out of bed and gazed lovingly at the sleeping man. From their earliest intimacy, He had accepted her completely as a woman, His woman, not a trans-gendered m... Read full Story
shemale lover 2012-10-07 5,621 hardcore Sex Toys tg
90%
Panty Town
Chapter One -- Jamie Jamie Sanders did not think he was a sissy. Growing up, he played with trucks and showed his innate male aggression though soldiers games with the other boys. He climbed trees and watched baseball with his Dad and brother. Unfortunately, by the time he was in eighth grad... Read full Story
shemale lover 2012-01-29 19,004 Big Tits sucking ass licking fucking
100%
My first dressed meeting Part 2
Today was the greatest day of my life I had already left home in daylight fully dressed and made up, and had driven to my first-ever rendezvous with another person, let alone a man, while in my other persona as Tiffany. When I had met my waiting admirer I had not only had my first-ever male kiss ... Read full Story
shemale lover 2012-02-21 2,452 sucking Fetish cum fingering deep throating
94%
Fooled by the Wrapping
It has been about 8 months now since my husband left me. No big blowup, or much arguing. He admitted he had been having an affair his third. I admitted that I had spent an evening with a young man. He had a long talk, and agreed to move out, we could live our separate lives. I kept the house, he agr... Read full Story
shemale lover 2013-03-28 8,459 hardcore sucking Big Cock Shemale and Girl Interracial
90%
Becoming a Drag Queen
I was thrilled when my boss told me he was sending me to San Francisco for a conference. It was a location on my "Top 10 places I wanted to go". I went online and Googled the major attractions and tourist "must sees in San Francisco. The conference was Wednesday to Friday and I figure... Read full Story
shemale lover 2012-03-01 13,646 first time sucking fuck domination
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 11,145 Bareback cum ass fucking slave
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 11,022 Teen (18+) Small Tits Crossdresser Fetish Blowjob Lingerie Guy Fucks Shemale cum in mouth
72%
Brenda & Bry
I like to write stories that involve kids having sex. And one of my favorite subjects is kids having incestuous sex. One story, about a brother and sister, attracted the attention of a 15-year-old boy when I uploaded it to the adult BBS that I regularly called in Reston. It seems that one of the ... Read full Story
ColonelSaint 2012-03-19 7,829 femboy dildo fucking
100%
Moon Probed at Hen Party Part 1
Honestly I had no idea all these things were going to happen to me. Perhaps I was just innocent but maybe when you read on you will be forming your own opinion about that. I guess it was something I couldn't talk about at school, it's just that I get aroused by my own body. I was kind of aware th... Read full Story
shemale lover 2012-05-23 3,321 hardcore anal sex long dick
68%
Ally
I was at a customers' house doing some yard work as they had paid me in advance for just minor clean up, pulling weeds, mowing, trimming the hedges. I was finishing trimming the hedges in between the neighbors and their house and as I finished up the neighbors' wife came out or so I th... Read full Story
Quib 2017-01-23 11,339 ass fucking crossdressing riding cock high heels anal fingering
95%
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 30,463 strapon porn
58%
My real story
I couldn't believe it. Here I was in bed with an older man – and one that I most wanted as he lay there sated by my ministrations to him. It had all started two weeks earlier when I had posted an ad on Craigslist. Up until this particular posting I had always been pretty bland..."Willi... Read full Story
shemale lover 2012-06-10 6,066 hardcore Cumshot bdsm oral sex
100%
First Night Nerves
My name is Timothy. I live in a large city in the English Midlands with my girlfriend Debbie. We are both 22 years old and have lived very happily together for over 3 years. We both work in a call centre for a large financial organisation. I am not tall – 5' 4" on a good day – and h... Read full Story
shemale lover 2012-09-22 3,830 anal orgasm fingering
50%
Clinton
"How many inches?" she asked. "Twelve," he said. "Really?" "Really." "If you're lying, you're just wasting your time." And mine, she thought. "I'm not." "Okay, then. It's a date." Tiffany hoped the jerk was te... Read full Story
shemale lover 2011-09-19 10,413 Big Cock cunt anus
100%
Serving Waitress
This is the first “didi” story I ever wrote. It’s my deepest (and darkest?) fantasy. It probably needs to be rewritten at some stage because I think it’s been written too much by my male brain and not enough by my female side. The story begins….. My wife, Susan, ... Read full Story
shemale lover 2012-08-28 4,575 anal sex Cumshot Creampie oral sex
100%
Don Juan With A Twist
A Celebration Stephanie thought that Halloween was the most romantically delicious of the holidays. She celebrated every year since her 21st birthday by going to a costume ball, picking up a masked stranger, and letting things happen as they may. Not knowing who was behind the mask was more ex... Read full Story
shemale lover 2012-10-23 2,816 cum oral sex foot fetish
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 13,765 first time Teen (18+) Amateur Group Sex Big Tits Cumshot Outdoor Bareback Blowjob Big Cock Asian lesbian public place
62%
Fifi La Femme: A Pansy at Last
I was quivering and shimmying with excitement dressed in my wife Doreen's black satin 36DD long-line brassiere with a pair of heavy silicone false titties wobbling inside the cups; her gorgeous deep six strap waist clinching suspender belt and flimsy see through panties that I'd bought for her; or r... Read full Story
shemale lover 2012-07-28 5,219 first time cum oral sex
80%
Chapter 2 - Cuckold Cruise
If you read Chapter 1, you know how I’ve been a weak, submissive sissy my whole life. My tiny nub of a penis never fully developed has never been inside a woman. I was fortunate enough to find and marry a strong and beautiful woman who accepted my submissive nature but only learned the full scope ... Read full Story
Sissy Annabelle 2022-10-07 5,053 Interracial crossdressing sissy cuckold chastity