Sort by
Relevancy

Free Stories

100%
The Big Mature Shemale Next Door
The Big Mature Shemale Next Door SugarandSalt "Please can I just wear my old swimming trunks?" Warren begged. "No!" his mom yelled back from the other room. "Barbara purchased that for you. It was expensive so you better remember to thank her." Warren looked at himself in the full length mir... Read full Story
Gwapo67 2022-05-03 7,641 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
100%
Shemale Adventure
You: early 20's, tall boyish good looks with a lean and muscular body. Dressed in tight leather pants, from behind your tight buns are revealed by the shiny black leather, as are your cock and balls from the front. You are wearing black leather boots and a denim shirt that refuses to hide your stron... Read full Story
shemale lover 2011-09-06 4,219 asshole Lingerie bisexual
100%
Porn Cinemas and GinaG
I really like porn cinemas, there is a certain seediness and sleaziness about them that makes them alluring to me. My problem is that living as I do in the south of the UK, there are no porn cinemas anywhere near me. Fortunately, I travel in my job quite a bit and so can get to cinemas in Birmingham... Read full Story
GinaG 2019-01-08 3,241 Stockings Crossdresser Amateur Cumshot Masturbation Blowjob Lingerie Mature cum in mouth shemale + shemale
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 4,114 Stockings Crossdresser Amateur Group Sex threesome Big Cock domination Mature foursome Homemade cum in mouth shemale + shemale milfs
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 11,139 Teen (18+) Small Tits Crossdresser Fetish Blowjob Lingerie Guy Fucks Shemale cum in mouth
84%
Becoming Zoe
My soon to be wife Annie had taken a job out of town and I only saw her every two weeks or so. I was so missing her. She and I had become long distance lovers. She was scheduled for a flight home on Friday night. I was going to pick up her son Zakk from his dorm and the two of us were going to p... Read full Story
Zöe from Kingston 2018-08-09 9,011 Stockings Teen (18+) Crossdresser Cumshot Bareback Blowjob blonde Big Cock Lingerie Mature cum in mouth
100%
Jesse's Dream Job - The First Day
Jesse didn't want to be late on his first day so he got to the office about 20 minutes early. He was looking sharp in a black suit pinstriped in light blue. The shirt matched the pinstripes and the tie was made up of reds, purples and a little of the light blue to bring it all together. Jesse had ne... Read full Story
shemale lover 2012-12-20 9,420 hardcore Cumshot Shemale Fucks Guy ass fucking handjob
83%
Wife Left Me so I Could be a Girl
I Am The Girl My Wife Did Not Want As the only child of a single mother I grew up around all things feminine. Having lingerie and stockings drying in the bathroom was normal for me and I always loved how pretty the full cut nylon panties and slips with tons of lace looked. I lived at home with... Read full Story
ASSEaster5678 2018-07-09 10,250 Shemale Fucks Guy Ladyboy Mature
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 4,107 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
94%
New Girl in Town
Margo sat next to me in the coffee shop late that Saturday afternoon. His real name was Mark, but he was one of the loveliest Drag Queens in New York City. I had been dressing secretly at home in my mother’s and sister’s clothes for just over three years, but at 18 years old, I had never... Read full Story
shemale lover 2019-06-04 9,870 anal shemale oral sex
85%
Shemale Public Bondage Fantasy
It was a chilly evening, I had arranged to meet him in the city centre. I was wearing a rather skimpy black dress, black lingerie and red high heels. It was my first time dressed in public like this. He was an average looking man, he shook my hand and kissed my cheek, and asked if I was ready. I aff... Read full Story
shemale lover 2013-06-22 4,740 Cumshot Outdoor shemale Lingerie ass fucking domination public
94%
Tortured by the T-Girl Tutor
Duncan didn't quite know how to handle it. He'd planned on a quiet Winter Break. Sleeping til noon, watching too much television and eating tons of junk food. That kind of stuff. He had a whole two weeks off from community college. At school, he was an outcast. They say life gets better after hi... Read full Story
shemale lover 2012-12-18 33,855 Big Tits shemale Big Cock Lingerie domination
100%
The Society
I met her during the summer. I was only nineteen and working to save some money for college. I had been raised by my grandparents who had both passed away over the past year. After the burial costs I was far from wealthy. My parents weren't around so I was on my own at a young age. I had moved a cou... Read full Story
shemale lover 2013-01-10 17,064 Crossdresser sucking Big Cock ass licking big boobs
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 4,081 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale high heel boots
50%
Sadopsychorama
He liked Clyrissa. She was a cock-hungry female if there ever was one. At 5'5", she had platinum blonde dyed hair, big tits, and a tight waist. She was a hot lay. But the best thing about her - the thing that stiffened his cock whenever he saw her was the fact that she was 53 years old. Somethi... Read full Story
shemale lover 2011-12-24 3,622 Fetish shemale anus
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 11,587 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
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 4,594 Stockings Big Tits Creampie Lingerie Guy Fucks Shemale Mature
73%
Nightclub Cum Slut
After splitting with my first boyfriend I went through a period of time I call my slut phase. I explored my sexuality in a massive way and did as much cock ass and pussy as I could. I thought that after I had been in a few relationships that my slut phase was over. I still had the odd one night stan... Read full Story
shemale lover 2013-01-10 7,030 Cumshot sucking ass fucking Guy Fucks Shemale ass fingering
50%
HOSPITALITÉ DU SUD
Ash regarda sa mère, incrédule quant à ce qu'elle venait de dire. Il comprenait la prémisse de base de ce qui s'était passé, mais le raisonnement qu'elle avait dû le déconcerter. "Pourquoi ?! Pourquoi ferais-tu ça ?!" Il a plaidé, la voix légère et désespérée. Elle haussa l... Read full Story
Femboy 2021 2023-02-05 991 Stockings Crossdresser Shemale Fucks Guy Big Cock Lingerie Guy Fucks Shemale
88%
LONDON CINEMA LIAISON
When I lived in London back in the 80s and 90s, I would often sneak off to a porn cinema with stockings, suspenders and knickers under my suit. My wife didn’t much like sex, so this was a release for me to get away from home and have some sexy fun. Once I had found a suitable seat I would ease down ... Read full Story
GinaG 2018-12-14 6,901 Stockings Blowjob blonde Lingerie Guy Fucks Shemale Mature Ass to Mouth
50%
Lady Regina
I know that many say that I I’m a coward because I am comfortable living in the closet as a part time female and not expressing my special female side completely. My friends all tell me to go out and have fun and not worry about what people say or think. In spite of that, and because of the prudish... Read full Story
Regina10 2022-07-01 4,795 Crossdresser Big Tits Masturbation Bareback Fetish Blowjob Ladyboy gangbang Lingerie Guy Fucks Shemale Mature pov
100%
Sissy Femboy Chrissy in Drag at the Club
"Can you wear a dress tonight?" "I can't crossdress in public, I'm not 'out' and don't want to be seen that way." "That's okay. We're going to a gay-only club that has a drag queen show tonight, so you'd fit right in." "Cool, but I'll have to change when we get there." "Awesome! See you tonight!... Read full Story
Chrissy Tunnell 2022-02-03 4,763 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
50%
LA VENGEANCE D'UNE SOEUR ⚧️ ⚧️
"Maman, maman," cria Michael. "Aide-moi!" Mary tourna la tête vers les cris de son fils pour ensuite entendre Melissa crier: "Sortez d'ici, espèce de pervers!" Mary se précipita dans le couloir jusqu'à la chambre de sa fille où elle trouva Michael passant devant elle, suivi de près par une bro... Read full Story
Femboy 2021 2023-03-26 877 Stockings Big Cock Lingerie Shemale and Girl Guy Fucks Shemale Sex Toys strapon feminisation du fils SOEUR ET MERE DOMINANTE FILLE ET MERE LESBIENNE
93%
Homework
Daniel was a 15 year old teenager, like any boy his age, he was full of hormones and sexual fantasies for every pretty girl that passed in front of him. In the last weeks of the school year, the history teacher had a child and was absent from school, being replaced by teacher Marlene, a trans woman.... Read full Story
haroldãosanguebom 2024-01-09 6,697 Shemale Fucks Guy Big Cock Mature
87%
Southern Hospitality Ch. 03
XtinaSmith2017 Ash looked himself over in his bedroom mirror critically, finding himself oddly self-conscious about his looks. He had been texting Laura all throughout the day and they had agreed that dressing pretty casual would draw the least suspicion, so he had. He wore a simple patterned ... Read full Story
Gwapo67 2022-05-16 4,594 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
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 3,417 Small Tits Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
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 3,967 Crossdresser Amateur Cumshot Masturbation Blowjob Uniform Lingerie Shemale and Girl Sex Toys Homemade self sucking pov cum in mouth
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 1,949 Shemale Fucks Guy Blowjob Big Cock Ladyboy Guy Fucks Shemale shemale fucks shemale Fantasy Tale
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 4,625 shemale tattoo shaved
72%
The Weekend
The weekend A story inspired by the very sweet and sexy samantha satine and my beautiful wife Part 1 - The preparation samantha packed her suitcase with her usual attention to detail, makeup, lingerie, wigs, but no dresses. Her head was confused by this, Master D had given her instructions... Read full Story
MasterofSissies1 2018-12-04 8,477 anal tranny Stockings Crossdresser Group Sex gangbang oral domination Guy Fucks Shemale transvestite schoolgirl School uniform maid uniform
100%
Meeting Amanda Ch. 2 - The Next Day
After a hot evening together, the story continues https://www.ashemaletube.com/story/meeting-amanda-6595/ ------------------------------------------------------------------------------------------------------------- “I could really use a shower,” Amanda said while she... Read full Story
rforasht 2022-09-07 4,151 Masturbation Shemale and Girl redhead Guy Fucks Shemale cum eating anal creampie couple & shemale
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 8,854 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
100%
Revenge is Sweet
Henry Stewart was thirty five years old, married to a very attractive woman who'd given him three kids, he owned and ran his own very successful computing company in San Diego, "Stewart Computing", meanwhile he owned a large house in the wealthy small town of River Falls. All in all, Henry... Read full Story
shemale lover 2012-09-01 7,555 Crossdresser Cumshot Masturbation Lingerie heels
93%
Miss Bernie
My name is Bernice McDonald and I am the very happy owner/ operator of a couple of children's day-care centers. I love my life and I love this work. I love children and since I have one of my own this helps satisfy my need to nurture. I have not always felt or recognized this need. I was born in... Read full Story
shemale lover 2013-02-22 13,852 hardcore sucking ass fucking Guy Fucks Shemale
70%
Ken and Ayala Part 1 Discovery
I'm working out at the gym, late in the evening on a Friday, lifting weights and working on my upper body to try in vain to get as big as some of these other massive muscle-bound gym rats. I was already sort of mad because my two coworkers, Jim and Tasha, had cancelled on our night out downtown, Jim... Read full Story
shemale lover 2011-11-09 4,474 sucking shemale Lingerie
100%
Just One of Those Days Part 2
Hello again. My name is Amanda, though sometimes I use the shortened version Mandy, when the mood suits me. I'm 33 and have stayed single for three years, since I discovered that Richard, my boyfriend, was not only cheating on me with dozens of women, some my so called friends but was al... Read full Story
shemale lover 2011-12-09 3,104 cum massage shemale sex
100%
Britney Story
Yeah, for those of you that have already read it, this is just my "Oops, I Did It With Britney" story that has previously appeared in four separate parts in the "celebrities" section, but I've put it on here for a couple of reasons. For one thing, I've noticed that the stories in... Read full Story
shemale lover 2012-09-25 8,881 Cumshot sucking Creampie shemale
100%
Santa & Mrs. Claus
In my story called "Santa Likes Fembois" here I explained that I discovered that last Christmas when Santa Claus visited my house then made me suck on his cock before fucking my boypussy. He also gave me an actual present: a winning lottery ticket. Well, with that multi-million dollar winning ticket... Read full Story
Chrissy Tunnell 2022-12-01 3,398 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature cum in mouth
91%
Birth of a New Sissy Part 1 Encounter
I met Jeff one day at the nearby tennis courts. I could never have imagined what the result of that meeting would be. I suppose I should tell you a bit about me. I'm a happily married 34 year old. About average in most respects. A little spare tire trying to form around the middle but in decent ... Read full Story
shemale lover 2011-11-17 5,175 cum Sex Toys crossdressing
92%
My Dream pt 3
Our first invitation arrived at the end of September. Sydney spotted it first and tossed it into the trash with out looking at it. She didn't tell me what it was and I didn't bother asking. The next invitation arrived two weeks later. This one Sydney opened and after reading it she passed ... Read full Story
Sydney Sun Min 2018-01-04 16,292 Group Sex Shemale Fucks Guy Shemale and Girl Sex Toys
84%
SUMMER VACATION by Spanky de Bautumn
In our house, it was a well-known secret that my mother kept her change in the top drawer of her dresser. The same drawer she kept her slips, chemises, panties, and all other satin, nylon, or lacy ladies undergarments. During the summer, my brother and I would run to that wondrous drawer when... Read full Story
SpankydeBautumn 2021-01-22 12,454 Small Tits Crossdresser Cumshot Masturbation Fetish Blowjob Lingerie Shemale and Girl cum in mouth
91%
Southern Hospitality Ch. 02
XtinaSmith2017 Laura felt herself lifted lazily from the arms of sleep, her body relaxed and floating on a small cloud of pleasure, her mind filled with images, sensations, not pulled from whatever dream she had just been having but instead, memories, memories from the night before. Memories of... Read full Story
Gwapo67 2022-05-16 4,432 Bareback Creampie Shemale Fucks Guy Big Cock Mature
66%
Cassandra Chapter 1
Cassandra is a tease, a flirt, a slut, a girl who lives very much for the moment. Unconcerned with propriety or fashion trends, she dresses in clothes that go right for the jugular of a fetishist's libido. Spandex, leather, latex, spike heels, corsets, overdone hair, make-up and fingernails - these ... Read full Story
shemale lover 2012-03-27 5,685 sucking fuck orgasm crossdressing
33%
Sleazy Walking
I was bored one night, and began to email wanted ads on craigslist to see who was hosting in my area. I lived in spokane, wa at the time in the east central area, sorta behind the fred meyer. This night was boring, my friends had left a while ago with their girl friends, jealousy began to set in. I ... Read full Story
Ville Lohner 2014-05-15 2,766 Stockings Crossdresser Amateur suck Lingerie
85%
My dream pt 2
A few hours later I woke up and realized that I had fallen asleep. Sydney must have also fallen asleep as she was still in my arms. I tried to get up with out waking Sydney but that wasn't possible. She woke up and quickly put on her nightie so she could walk me to the door. When we entered ... Read full Story
Sydney Sun Min 2017-12-26 17,863 Shemale Fucks Guy
100%
Seducing the Delivery Man
Angela sat on her couch in her living room sipping on a glass of wine and tried not to cry. What a shitty birthday. Her best friend, Kathy, who happened to be a co-worker of her boyfriend John, sent her an interesting picture of him a couple of days ago. Apparently, their office had thrown a retirem... Read full Story
JohnSorenson 2024-01-12 6,240 anal Amateur Blowjob Guy Fucks Shemale cum in mouth
100%
Slut /W Bad Boy
I was excited as always because I was about to go out in public and hopefully I will meet some horny man with some money and get laid. Now, to make sure that I am a picture of femininity, I double checked my makeup in several mirrors from many angles. My lips were perfect and I made sure my cheeks b... Read full Story
Regina10 2020-12-04 6,851 Stockings Crossdresser Big Tits Cumshot Bareback Fetish Blowjob Big Cock Lingerie Guy Fucks Shemale pov Ass to Mouth
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 4,835 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
100%
FUTA CUCKS LE PETIT AMI ⚧️
Olivia grimaça alors que les sacs de courses s'enfonçaient dans ses paumes. La journée avait été longue, et l'ascenseur en panne ne lui apporta aucune joie alors qu'elle se dirigeait vers le premier des sept étages qu'elle devait gravir. Une collègue de travail avait mentionné la liv... Read full Story
Femboy 2021 2023-02-11 800 Stockings Blowjob Big Cock Lingerie Shemale and Girl domination Futanari
80%
Trance club
It was the worst day in my life. My girlfriend Ally and I had been quarreling and rowing for several weeks, we were on the verge of breaking up. I just wanted her to be happy. I lived my life for her. I guess I stood no chance to make her smile at me again. We broke up. Ally said everything was chan... Read full Story
shemale lover 2014-05-25 7,714 sucking shemale
100%
A Shemale Vacation Part 1
I was eighteen, naïve and horny. After graduating from school a group of us decided to head to Europe for a last trip before having to enter our real adult lives. It was a chance to get completely drunk and have lots of wild sex. At least, that was the idea in our simple teenage minds. As for m... Read full Story
shemale lover 2011-09-05 10,706 Cumshot sucking cum swallowing
100%
The Meeting of Cortney and CiCi p1
Cortney could not keep herself from thinking about the upcoming date with CiCi as she sat in the luxuriant bath water and shaved her legs. She planned to fuck the glam slut whore long and hard. But first, the metamorphosis to turn her into the dome bitch - Cortney. She rose from the bath, patted... Read full Story
shemale lover 2013-04-15 3,476 suck shemale oral Lingerie make up
96%
A Night of Lust
I was out at a night club with a few friends, and we were there for for a while before I noticed this sexy, rather short girl across from me at the bar looking over. I could tell, even from this distance that there was something special about her, I wasn’t sure what that was quite yet though. The mo... Read full Story
JessicaEdwards 2018-08-07 17,932 Stockings Amateur Cumshot Masturbation Bareback Creampie Shemale Fucks Guy Blowjob blonde Big Cock Lingerie deepthroating Guy Fucks Shemale cum swallowing deep throat deep penetration cum swapping pov Ass to Mouth cum in mouth anal fuck sloppy virgin ass
100%
Lady In The House Ch. 07
A story by MicheleNylons (Carmel and Charlotte want theirs.) From Part VI "You look gorgeous Michele," Carmel whispers through the bars. I wondered if she had read my mind when I was standing in front of the mirror admiring myself. "Well, I have to say you girls are looking something spe... Read full Story
✘Transensual✘ 2019-02-25 3,231 Crossdresser domination prisoner shemale lesbians Prison Bitch
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 14,780 first time shemales interracial sex
100%
Happy Birthday Baby
It was early in the evening and the cloud were darkening the sky as a storm was beginning to make its way in. as I pulled into the driveway of my home the wind was blowing the leaves around violently. As I got the groceries out of the car and hurried up the front steps it was very difficult to keep ... Read full Story
shemale lover 2013-01-11 4,736 hardcore sucking Big Cock ass fucking Guy Fucks Shemale