Sort by
Relevancy

Free Stories

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 7,764 Teen (18+) Small Tits Amateur Group Sex Latina Blowjob gangbang Guy Fucks Shemale cum in mouth
91%
Masturbation fantasies: Amanda, queen of the peep show
A guy visits a peep show with unexpected results. As he gets to watch a girl with something special, he discovers his hidden desires. This story contains: peep show – voyeur – gloryhole - fake tits – group masturbation – male masturbation – shemale – frottage - titfucking When William finall... Read full Story
ThatEroticWriter 2019-07-24 8,569 Big Tits Cumshot Masturbation Uniform Frottage
83%
Epic weekend with stepbrother
Ok so me and step brother both graduated and where ready to celebrate we decided we are going to Vegas. We where both virgins so we couldn’t think of a better place to loose it. How where supposed to loose it was supposed to be a much different story. His was supposed to be like any young handsome ... Read full Story
Wet boy kitty 2021-01-29 4,510 Small Tits Crossdresser Amateur Masturbation Bareback Creampie blonde Lingerie cum in mouth
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 4,999 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade pov cum in mouth webcams
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 3,573 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking pov cum in mouth webcams
100%
tiffanylondontv becomes a captive slave prisoner and whored out
I had connected with Master X on a BDSM Fetish contact site. He was the owner of a fetish store and he said that he had been on the BDSM for several years. He had carefully studied my own profile and had seen that I had an immense interest in being used like a slut, being covered head to toe in... Read full Story
__tiffanylondontv__ 2022-09-20 4,597 Crossdresser Amateur Group Sex Fetish Latex Mature
100%
I fucked my personal trainers ass for the first time
I greeted him on my bed in my sheer black lingerie. I knew he’d be nervous, and truly I was as well. We’d spend so much time in the gym together and I knew he wanted me, but taking that next step was sometimes difficult, especially when our relationship was always professional. Posing for him, I r... Read full Story
Madison Heights 2023-05-18 7,113 anal Shemale Fucks Guy Big Cock Frottage
50%
lust of a sex-agenarian nana-pops
Frenzied lust of a sex-agenarian nana-pops; between dream and reality I had never fantasized of a manly man, even after offering my virginity; to a fabulous sissy. Before my new Era, my fantasy preferences were always with glabrous he-she’s, same about my relationships after… BUT BUT BUT… My last t... Read full Story
hippocampus_171 2023-07-09 4,822 anal Small Tits Amateur Group Sex Masturbation Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy
100%
Lola Chapter 5
Lola chapter 5 Summer vacation was coming to an end. Most of the time we had been to ourselves, mostly at home but also a couple of shorter trips. Beer tasting in Stockholm's archipelago, a trip to the west coast, overnight stays in hotels, everywhere we were received like any other couple. A fam... Read full Story
BellaBeau 2023-10-30 5,877 anal Cumshot Latina Bareback Creampie threesome Shemale and Girl Lola
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 2,376 anal Amateur Creampie Blowjob Sex Toys Mature small cock big ass cum in mouth
100%
GRANNY TRANNY'S HOUSE of SIN
It all began after my husband died and I was living alone. I decided to adopt a family and corrupt their minds. You see, I'm an ex SHEMALE PORN STAR and I like to live a wild life and I figured after my husband died I should relive my wild life and be happy. I reached over for my GOLD METAL MESH CIG... Read full Story
BITCHGURLvr 2024-09-01 4,599 shemale cum sex Cigarettes
86%
Passionate Sex with a Beautiful Shemale
a man and his shemale lover get down to business Will led Sarah by the hand into his bedroom. He closed the door as they entered and pulled her towards him. He placed his hands around her, caressing her toned stomach as he slightly nibbled on her earlobe. He could feel her trembling in his arms. Sa... Read full Story
shemale lover 2014-03-23 6,710 anal Blowjob shemale 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 10,764 Big Cock cunt anus
81%
Rebecca's Secret
-1- The hour was growing late as I looked around the cozy living room. Six of my friends were sitting in various places, in various positions, all watching some late night horror movie on the television. There was a feeling of general contentment. We had arrived at the house several hours earlier... Read full Story
shemale lover 2011-10-19 5,297 Cumshot shemale oral sex
66%
Showing Off For My Wife's Pleasure
There I was lying on my back, on the floor of a cheap adult bookstore. All I was wearing were 5" heels, black thighhighs, and a nipple chain. In one hand, I was jerking my throbbing shaved shaft while I was using my other hand to fuck my ass with a double headed dong. Cum was glistening on my f... Read full Story
shemale lover 2011-10-25 5,473 anal asshole shemale
100%
My Beautiful Surprise
Mark Holloway groaned as he sat up in bed and reached behind him to touch Madison. It was six o'clock on Saturday morning in Birmingham, Alabama. His hand met only a cool pillow and undisturbed sheets. Then he recalled with an increase in his heartbeat that she was due to arrive at the Birmingham In... Read full Story
shemale lover 2011-11-01 5,979 sucking shemale cum
77%
Caramel And Devin
I began crossdressing at 12, but it wasn’t until I was 17 when I dressed up completely for the first time. When my parents went away for the weekend to Atlantic City, I took advantage of the opportunity to explore my feminine side to the fullest. As soon as they left the house that summer morn... Read full Story
shemale lover 2011-11-10 4,360 Cumshot sucking fingering
62%
Naples
I had been at sea about a month when my ship pulled into Naples, Italy. The only action I had seen had been slipping away to my hiding place on the ship to jack my dick on a regular basis. I was ready to find some Italian pussy. I was slim about 6' with blonde hair and a fat 7" cock that ... Read full Story
shemale lover 2011-12-16 6,554 Teen (18+) shemale gay
50%
Debbie Part 6
Debbie was awakened by someone holding a hand over her nose and mouth, so that she couldn't breathe. She struggled, weakly tossing her head before opening her eyes. She looked straight into the eyes of Dr. Jacobsen, smiling evilly down at her. He continued to hold her head so that she couldn't breat... Read full Story
shemale lover 2011-12-23 4,481 transgender toys bondage and discipline heavy
80%
Debbie Part 7
As Debbie was led into Dr. Jacobsen's office, she saw that Mistress was already there waiting for her. "Your property Miss Chamberlain", the doctor proclaimed, indicating Debbie. Debbie's heart began to flutter with love and submissive fantasies as she saw Mistress. Mistress was dressed in... Read full Story
shemale lover 2011-12-23 9,683 transgender toys bondage and discipline heavy
100%
Blossoming Shemale
My name was James. It was, before everything that happened, anyway. I'd come from pretty good stock, as the snooty, upper class would likely say. I guess I still did, although it would take a DNA test to prove it now, and to be honest, I didn't really have the desire. That was all before. I have to ... Read full Story
shemale lover 2012-08-01 5,091 Cumshot shemale Big Cock oral sex
94%
Adam Picks Up a Transgender
Sitting along the short L stretch of the bar, Adam admired the pretty girl sitting most the way down the longer length of the bar. Her blonde hair was long and curly. Her tight dress had a swoop front that showed plenty of cleavage. He knew the rumors. She wasn't completely a "she." She wa... Read full Story
shemale lover 2013-02-12 7,287 sucking Shemale Fucks Guy Lingerie ass fucking handjob
56%
Blow Job
My e-mail is: My rusted, green Toyota Tercel pulls into the mall parking lot. I pick a spot at the back, beyond where even employees park. The next car is a blue pickup 20 spots away. No one parks here, except at Christmas. But I know that I'll soon need the privacy. I'm a freak, a cross-dresser... Read full Story
shemale lover 2013-08-09 7,012 Crossdresser Masturbation Lingerie stripping party
83%
Milking Time Jordan's Arrival
These stories involves a group of shemales who live on an island that exists in our world, but they chose to remain mostly isolated. That's part of the reason I also call them amazons. The shemales in my stories have genitalia that start at John Holmes' size, and then get much bigger. (This is a... Read full Story
gman57 2019-09-25 10,700 Big Tits Big Cock shemale + shemale
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 3,587 Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking cum in mouth webcams
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 15,103 first time shemales interracial sex
74%
Sexy Young Shemale
When I was twelve my next door neighbors Sam and Ted trained me in the art of cocksucking and creamy yummy delicious cum eating for hours everyday during my summer vacation and I fucking loved it! I was small framed and wore my long blonde hair in a pony tail and always wore my smallest shorts so I ... Read full Story
shemale lover 2018-09-28 10,667 sucking Big Cock cum swallowing
100%
Buffy the Shemale Vampire Slayer Part 5
By the time that Buffy arrived at Rupert Giles' apartment, the former librarian, her ex-Watcher, had just finished reading a new volume of what Edgar Allan Poe, in The Raven, had referred to as a "curious and quaint volume of forgotten lore." He'd just settled the large, leather-bound volu... Read full Story
shemale lover 2011-08-19 3,740 hardcore celebrities shemale
100%
Buffy the Shemale Vampire Slayer Part 12
The demons found exits in the walls or floor, vanishing between chinks of stone or through hidden grates or into holes they'd dug for themselves over the long centuries of their residence-or imprisonment-in Baphomet's palace. Only one remained. "My former consort, Baubo," Baphomet intro... Read full Story
shemale lover 2011-08-21 4,621 hardcore asshole Big Cock
87%
Shemale First Time
First time Sex with a shemale. Intro. I have read several stories of first time sex with Transexuals and none relate to my experience. So for those who are truly curious about how to go about it and what it is like this is my tale. I have always been a straight guy as far as I know. Married... Read full Story
shemale lover 2011-08-24 9,330 first time asshole shemale
79%
My Shemale Stepmother Part 1
My parents split up when I was eighteen, I was a little distressed by it but we had never been as close as some. Still, I didn't really see what had driven them apart so quickly and so thoroughly that they never even spoke any more. I guessed maybe one of them must have had an affair and that was re... Read full Story
shemale lover 2011-09-01 19,125 tranny Big Cock jerking off
100%
Allison is Born
What a wonderful day this is. This is the first day of my new life but before that I should give you some history about me. My name is Allison, I am a 24 year old male that lives in a small town in Ohio. My father died when I was very young and I was raised by my mother. I guess you could say I am i... Read full Story
shemale lover 2011-09-24 3,689 Stockings Big Cock cum stroking
100%
An unexpected kiss under the rain
Army Bear left that morning leaving me horny as hell. I couldn't go back to bed without playing with myself for a while. I opened my Pandora box and I took out my 9 inches, big dildo. I played with it for a few long minutes, burying it all deep in me thinking of him. Doing a few hits of poppers, I f... Read full Story
HotVersatileTs 2011-10-05 4,797 sucking domination foreplay cd
60%
The Ultimate Cock Ball Torture
I miss my cock. Sometimes. I had one once - one of my very own, connected right to me - but now it's gone. Never thought I would miss it. I'm sure you've guessed by now that I am a full transexual. I had the boob job and started hormone treatment years ago and felt much better as a shemale th... Read full Story
shemale lover 2011-11-12 7,155 shemale transformation
100%
Just One of Those Days
Let me start by introducing myself. My name is Amanda, though I sometimes use the shortened version Mandy. I am thirty-three but my sexual awakening didn't really occur until I had turned thirty. Previously I had been a generally shy and quiet girl with a steady and normal relationship. ... Read full Story
shemale lover 2011-12-07 4,849 shemale tattoo shaved
100%
Debbie Part 5
Debbie didn't wake up until her gag was wrenched from her jaws. Her hood, collar and earplugs had already been removed. "Wake up, shit-head," Mistress spat and slapped her face hard. Debbie came awake and noticed that all the straps holing her to the couch had also been removed. She felt a... Read full Story
shemale lover 2011-12-22 5,502 transgender toys bondage and discipline heavy