Sort by
Relevancy

Free Stories

73%
How did i get here?
I’m a thin, pretty good looking 30 years old guy, living with the girl of his dreams. But a girl without a cock is no longer enough now. All my life I considered myself as a straight guy, even if sometimes duchbags at school called me a fag. I only dated girls, prefered long love stories over on... Read full Story
slavetocock 2015-09-25 6,302 sex toy Crossdresser feminization slave sissy
80%
Blowing Strangers
I was headed back into town from a couple weeks on the road and decided to stop for the night at a particular hotel, because it a had a small bar attached. After getting a room, I went upstairs to change. As usual, my outfit was right on the border of sexy and slutty. The five inch heels might have ... Read full Story
pennypenny 2017-07-05 7,840 Crossdresser Blowjob Guy Fucks Shemale cum in mouth
50%
Domination of Bjarne
Dear Diary. At the behalf of my lover Bjarne alias Cigar54, I will ease the curtain of my bodouir and invite the curious reader inside to a little piquant seance that we had together during his recent visit over here. Bjarnes visites always begins with kissing deeply, while my hands find the way to... Read full Story
Louice 2018-03-02 3,337 Amateur Shemale Fucks Guy domination Ass to Mouth
88%
Seattle Weekend
Saturday morning and such a beautiful day nice and cool morning I went for a run. I consider myself in fairly good shape for my age but I try and make it to the top of a hill in our neighborhood. I get winded fairly quickly. Coming down the hill I ran into a nice looking athletic girl, maybe 38 year... Read full Story
Jon Paul 2018-08-09 10,087 Big Tits Cumshot Bareback Creampie Blowjob Ladyboy Guy Fucks Shemale cum in mouth
94%
My first Shemale
“Curious? Bi?” Well, yes, but only with a shemale. Beyond that I’m a firmly planted heterosexual. For many years I longed to have sex with a shemale but never did anything about it. (I’m not much of an initiator). The community I live in has lots of shemale beauts; maybe that started my intere... Read full Story
SachinJoy 2018-10-04 32,631 Cumshot Shemale Fucks Guy Blowjob Big Cock Ladyboy cum in mouth
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 8,702 anal tranny Stockings Crossdresser Group Sex gangbang oral domination Guy Fucks Shemale transvestite schoolgirl School uniform maid uniform
100%
Getting Fucked By Jeff
Getting Fucked By Jeff I was sitting at the bar one night having a drink and wanting some dick when a man sat next to me and said “Hi, I am Jeff.” Smiling at him, I said” Hi, I am Penny.” Jeff and I chatted and he bought me another drink. After a while, Jeff said” In all honesty, I only boug... Read full Story
pennypenny 2019-02-25 6,370 Crossdresser Amateur Cumshot Bareback Creampie Fetish Blowjob Big Cock redhead Guy Fucks Shemale Ass to Mouth cum in mouth
75%
My Buddy the Crossdreser
I hadn't seen my buddy in a while. I called him up and he was game. We usually fuck outside his front door, I get to his new house and the flood lights come on. I'm thinking what is he planning. I stay in the car and he come by and says he's getting in. he tells me to drive up the road. we got to t... Read full Story
horny.hiker 2019-03-04 4,208 Crossdresser Bareback Big Cock Ass to Mouth outdoor sex breeding swallow cum
85%
Transgender orphan meets new kid in town
I stared at the wall of my room. My family had moved over the summer. Tomorrow morning I would start school, in a new town, and all my friends were back East. "California is a great place to live, and Sacramento is a fantastic city! It's the capitol of the state!" My dad had gotten a new job, so ... Read full Story
ASSEaster5678 2019-03-18 6,256 Shemale Fucks Guy
100%
My anonymous shemale
She walked into my apt. She was beautiful. We kissed passionately. I stripped her clothes off and let them fall to the floor. I sucked her titties and held her hardening cock. I dropped to my knees and took her dick into my mouth. As I sucked it got hard as a rock. She grabbed the back of my head an... Read full Story
shedawg 2019-04-15 4,306 Amateur Bareback Big Cock cum in mouth
100%
Incubator
For lack of a better term, I will call him my Lover. I call him Grae, which sounds like "gray" if you are doing a rather poor impersonation of a Scotsman. Not that I have anything against the Scots; that's just as close as I have been able to come to pronouncing his real name. You would think that s... Read full Story
ASSEaster5678 2019-04-23 4,578 Big Tits Bareback Shemale Fucks Guy Big Cock Guy Fucks Shemale monster
84%
Chambermaid
Denise loved the weekend morning shifts, especially when guests had left ‘breakfast in bed’ signs outside their doors. She wore her usual indecently short lacy black uniform, with a lacy white apron, black matching undies, stockings and black high heels; and with her hair and make-up immaculate she... Read full Story
Emma W 2019-10-29 6,125 blonde Uniform Guy Fucks Shemale
85%
Loving Strangers
In the past I had never failed to disclose my sexuality to a new male prospect. I looked good in my tight dress that showcased my woman's ass, and the spike heels that made me look so fuckable. I knew from past experience that guys could get really pissed and violent when they found out you weren't... Read full Story
Regina10 2020-06-23 4,692 Cumshot Bareback Fetish Blowjob Big Cock Guy Fucks Shemale Ass to Mouth
88%
Trip to Portimão
It is about a 3 hour drive depending on traffic to the Tivoli Marina Portimão in the Algarve from where I was staying at the Hotel Mundial. Oliva came to pick me up. She had one of those Toyota SUV things. I put my bag in the car and I noticed Olivia had rather a collection of luggage. I smiled to m... Read full Story
Rusty12 2020-09-18 4,090 Amateur Cumshot Masturbation Shemale Fucks Guy Blowjob domination old-and-young
87%
My first bi encounter
As a young catholic boy I always prayed I would have a women’s body. I would wear my sister’s clothes and masturbate in my bedroom. I have been a closet cross-dresser for a long time. In my early twenties I rented my own apartment. I would buy from Fredericks of Hollywood catalogue for my outfits, ... Read full Story
Palba 2020-11-12 6,622 Amateur Bareback Creampie Ass to Mouth guy fucks shemales
94%
Sissy Slut: Gang Favored
I confess I am a nymphomaniac shemale slut who loves being the object of a man’s desires. That's why I was out here with these hookers trying to hook up with somebody to have sex. I'm either having sex or I'm thinking about having sex most of the time I like being a honey. I love having sex with men... Read full Story
Regina10 2021-03-02 7,506 Stockings Big Tits Cumshot Bareback Fetish Blowjob Big Cock Ladyboy gangbang Guy Fucks Shemale cum in mouth double anal
100%
Regina and Tommy
I was getting fucked hard and aggressively by a certified bad boy named Tommy. I've never been the kind of girl who liked bad boys until I met Tommy. Tommy like doing all kinds of wild crazy things to me and I was under a spell and couldn’t object. Tommy was like the asspussy whisperer and he gave m... Read full Story
Regina10 2022-03-02 2,978 Stockings Big Tits Cumshot Bareback Creampie Fetish Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth
100%
My Sugar Daddy Fucked My Girlfriend...And I Joined In
I am a shaved-smooth, boyish bisexual male slut. At 43, I still look and feel young, and I enjoy the feel of and attention from older men, the older the better, 55 and up, with gray hair, wrinkles, and very hairy chests and bods. My Daddy, a 70-year-old White man that fits this description, "owns" m... Read full Story
Chrissy Tunnell 2022-04-12 2,729 Crossdresser Amateur Shemale Fucks Guy Fetish Blowjob Ladyboy Shemale and Girl Guy Fucks Shemale Mature cum in mouth double anal
100%
Surprise Ending (The End)
Karla struggled a bit to get the huge, bulbous head of her cock inside of me. It was like my ass had licked a battery. A charge went through my body that while painful, was exhilarating and exciting. "Ahhh," from my lips was all the encouragement I could offer and Karla took it. She steadily push... Read full Story
Chantel13 2022-08-23 5,535 Amateur Outdoor Shemale Fucks Guy Big Cock Shemale and Girl Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Crossdresser gets dick for first time
I was so tired of just watching porn. So tired of the sissy hypno threads that made me crave men, crave cock, crave being weak, crave being the bitch...only to cum and do nothing about it. But the desire to transition from fantasy to reality was growing stronger and stronger. I decided it was ti... Read full Story
Sissy Ava 2022-10-11 7,856 Stockings Crossdresser Amateur Bareback Big Cock Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Fuck Room
I'll be honest with anyone reading this. I have been very slutty since I began putting a lot more time into my dressing up and going out. I met plenty of guys off of Grndr and Tinder, and some very hot experiences took place on some of those..."dates". I actually liked the feeling of being used. Kno... Read full Story
Sissy Ava 2022-10-24 4,467 Stockings Crossdresser Blowjob Big Cock Guy Fucks Shemale Interracial public sex
100%
Groped on the Bus!
In real life I do not crossdress in public, I am not yet comfortable being my true transgirl self, I wear normal men's clothes and I look like a guy. So I look very different from my persona here. So...there I was standing among dozens of strangers at a bus stop. I kept looking up from my phone ... Read full Story
Chrissy Tunnell 2023-03-22 5,081 Small Tits Masturbation Fetish Big Cock Ladyboy Guy Fucks Shemale Frottage
100%
A Series of Perverse Dreams, Part 1
My relationship with Hannah had always been mutual in the idea that neither one of us was ever truly the dominant one. It was an equal, balanced relationship of mutual fucking and sucking. However, I had REALLY enjoyed being made into a submissive sissy slut by Nikki. Something changed in me after o... Read full Story
KaceyKlarissa 2024-02-24 5,462 anal Small Tits Crossdresser Group Sex Big Tits Outdoor Big Cock gangbang domination sissy femboy Ass to Mouth cum in mouth
100%
Bimbo Bombshell - Chapters 1-2-3
Bimbo Bombshell - Chapter One: Singled Out! Even though it was Friday, the bar wasn't particularly crowded that night. I never knew what hit me. This Gorgeous Blonde bombshell, starts flirting with me right a my table. I found myself wondering why this glamorous beauty, had chosen me. I was... Read full Story
Hardrock51Fifty 2024-06-23 4,889 Stockings Big Tits Shemale Fucks Guy Fetish Blowjob blonde domination Guy Fucks Shemale blonde shemale PDA Public Displays of Affection
86%
9 ladyboys gangbang me and force me to suck their cocks in my fa
Our forum member, Dutchboi, had this fantasy of being dominated, sissified and humiliated by nine Asian ladyboys, with Mint and Nancy being two of them. For some of You this story may sound too cruel, others will find it really hot. My fantasy is to be at a ladyboy's apartment and fall alseep aft... Read full Story
shemale lover 2015-03-03 10,718 anal Blowjob Asian
100%
Buffy the Shemale Vampire Slayer Part 11
Darkness had fallen upon the demon world. In the intermittent flashes of lightning that resulted from Willow's weather spell, the landscape was illuminated, and the horrible phallus-plants were revealed, writhing and thrashing. The cock-stalks within Buffy's mouth, cunt, and ass, and the hollow tubu... Read full Story
shemale lover 2011-08-21 4,248 asshole shemale Big Cock
100%
Adventures of Shemale Sandra Part 1
His name was Phillip. Or at least it had been. Honestly, he wasn't sure who he was; all he knew was that what he had done two years ago was what he thought was right. This was the lifestyle he wanted. It should be said that Phillip has always had strong female influences throughout his life. He a... Read full Story
shemale lover 2011-09-02 3,761 anal sex asshole cum
94%
She was a he
I was recently divorced, 39 years of age and living in an apartment in Sydney's inner eastern suburbs not far from the famous red light district of Kings Cross. After two failed marriages, I was footloose and fiance free and as lusty as a rampant bull on speed. I chased after anything wearin... Read full Story
shemale lover 2012-01-24 6,926 Cumshot Guy Fucks Shemale Frottage
100%
Dottie's Back Chapter 2
After tossing my purse onto the kitchen counter, I nearly ran across the backyard toward Kim's house. Stopping a few feet short of the fence, I kicked my heels over it, pausing to be sure they landed in Kim's yard. On a previous occasion, one of my heels flew into the yard next to Kim's. This forced... Read full Story
shemale lover 2013-01-29 3,136 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
95%
An itch that finally got scratched
Hey all! New to the site, but have been a major fan of TS/CD etc since I was a teen. I remember always fantasizing about what it would be like if I was to ever get an opportunity to make the fantasy a reality. Well, I finally got that chance and took full advantage of the situation and I wanted ... Read full Story
sizeman 2013-04-10 8,190 Shemale Fucks Guy doggy style Guy Fucks Shemale cum swallowing riding cock
86%
My TS experience in India, Pune
Im 6 ft tall fair with handsome looks and regular exercise keeps me fit and healthy. Im also blessed with quite big and thick cock with indian standards. Im total shemale fan and I watch shemale porn crazily every day. I was in search of TS or Shemale in pune since long then one day I was searchin... Read full Story
daynightfun7 2013-07-10 13,195 suck shemale fingering ass fucking Guy Fucks Shemale condom sex
90%
My first shemale sex
I had developed a strong desire to be with a hot looking shemale for a long time. I really did not know how to make contact with anyone in the small city I lived in, and figured it would likely never happen to me. One day at work at my computer support job, I was informed that another branch of our ... Read full Story
shemale lover 2013-08-14 94,501 tranny sex toy anal sex suck Shemale Fucks Guy dildo
82%
Dick And Ass
I don't have this kind of sex often, I feel like it's wrong to want this, wrong to crave this so badly. I am by no means a sissy or a gay man. I have a wife a family.... I just need it the domination the surrender of all my will and being, the first thrust that hurts so fucking bad when it... Read full Story
JustaSwitch1 2016-06-15 11,537 Shemale Fucks Guy oral domination bbw
84%
When I Knew I Was A Crossdressing Sissy Slut
I remember the fun I had taking selfies with sexy little outfits and make up on. I loved the dirty,sexy feeling of taking pics of me exposing my asshole and sliding back onto a suction cup dildo stuck to the wall. Hearing from a guy just how much he wanted to eat my ass or fuck me always got me ting... Read full Story
pennypenny 2018-09-05 7,091 Crossdresser Cumshot Bareback Blowjob Guy Fucks Shemale Ass to Mouth cum in mouth
92%
My wife Gwen
My wife, what can I say she is tall and leggy with thick, natural wavy orange-red hair with beautiful porceline skin and just enough freckles to tell you she is a true ginger. Add to that smokey green eyes and thin sexy lips and you can see why people refer to her as Gorgeous Gwen. From the time we... Read full Story
Zöe from Kingston 2019-01-08 7,647 Shemale Fucks Guy redhead Guy Fucks Shemale cum in mouth
100%
Leslie
Where do I start? How about at the beginning. My name is Cal I am divorced and living alone. I am not a bad catch I am five foot eleven, short black hair, green eyes and no visible scars. I am a regular at the gym so I am in shape but not ripped. A seven inch uncut cock that I can use well. I... Read full Story
Zöe from Kingston 2019-02-04 9,240 Cumshot Bareback Blowjob Guy Fucks Shemale Bra and Panties
95%
She Wood in the Wood
"Alright, juniors and seniors to the white bus please." Mr Jacob's voice cut above the rabble of the moving crowd. All 50 of us filed into the large vehicle, talking loudly, a mixture of excited comments and loud complaints. It was field day, which meant the whole school was going to take up an e... Read full Story
ASSEaster5678 2019-03-18 7,177 Shemale Fucks Guy public natural
80%
Wrong Vampire
I consider myself a fairly tolerant person. I judge each person on their merits, not their skin color, gender or even sexual orientation. I'm even in favor of the Vampire Rights Amendment, but I must admit, unlike other groups people discriminate against, they make me uneasy. They claim that all the... Read full Story
ASSEaster5678 2019-04-23 6,557 Cumshot Shemale Fucks Guy Guy Fucks Shemale cum in mouth vampire
75%
Honeymoon Suite 2
Jason is on the phone with room service, while I am about to change out of my wedding gown. I had just got married, and I was now the blushing bride. Yes I got married. I was nervous now and my pussy was burning, because of the crazy bet we had made about not having sex a week before the wedding. We... Read full Story
Regina10 2021-02-22 3,658 Stockings Crossdresser Big Tits Cumshot Bareback Creampie Blowjob blonde Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth
100%
The Golf Bet
A couple of years ago I joined a new golf course, I wasn't the best golfer but very keen, I would be at the practice area almost everyday for at least an hour. Over this time I got to know a number of members and it was a good way of meeting people to play with. Over that year I met a number of new... Read full Story
chris1989r 2022-01-03 4,742 Amateur Cumshot Shemale Fucks Guy Guy Fucks Shemale cum in mouth
80%
TG Girlfriend moves in (part 2)
My wife Lydia and I have been married about 9 months, we have a very close TG friend, Joanne, that lives next door and every once in a while, we get together, and all go out and enjoy. We have had sex together, and when Lydia is away Joanne, and I are together at every opportunity. Joanne and I work... Read full Story
Jon Paul 2022-01-21 3,476 Big Tits Cumshot Bareback Creampie threesome Blowjob Shemale and Girl Guy Fucks Shemale
100%
Gangbanged at the beach
My BBC friend took me to the beach, where people make sex. We arrived in his van. I was in the back of the van, chained blind folded, with my mouth wide open and a huge horse dildo in my sissy pussy. Suddenly I hear the van door opening. I hear many voices of other men. My BBC friend was telling oth... Read full Story
brunasissyslavedolrj 2022-05-09 4,534 Crossdresser Group Sex Outdoor Fetish Big Cock Lingerie domination Guy Fucks Shemale Interracial Sex Toys Ass to Mouth cum in mouth
100%
bi to sissy caught and turned
It was during a Wednesday nite supper this past April when Penny my wife of seven years, suddenly looked me straight in the eyes while calling me a GAY COCKSUCKER ! Instantly while I swallowed hard and quickly looked away from her, my worse dreaded fears in life had somehow just become reality! So ... Read full Story
redthongthong 2022-08-02 8,917 Crossdresser bisexual sissy crossdresser forced feminization CAUGHT!
100%
Amy and the Straight Jocks PT1
Only a couple close friends knew for sure and most others knew it as just a rumor. Amy dressed and lived life as a girl like she had since the start of high school when she moved from a new town. The jocks would laugh and whisper to each other when she walked by debating if the rumors were true. Co... Read full Story
DADDY4sluts 2022-08-09 3,889 Teen (18+) Cumshot Bareback Creampie Blowjob Guy Fucks Shemale cum in mouth
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 4,359 Stockings Crossdresser Amateur Group Sex threesome Big Cock domination Mature foursome Homemade cum in mouth shemale + shemale milfs
100%
The morning after
Part 2 of my Gaby story. Hope you all like it and be patient with my english ;). Part 1 you can find here: https://www.ashemaletube.com/story/first-time-with-big-surprise-6821/ I woke up slowly, the sun shone on my face and I could only open my eyes slightly. "What happe... Read full Story
Marten1201 2023-01-19 4,923 Big Tits Bareback Creampie Shemale Fucks Guy Guy Fucks Shemale
100%
Becoming addicted to her she-cock
"I'm going to make you a very happy woman tonight when I slowly but firmly slide my long, thick, hard she-cock all the way up your tight virgin ass tonight baby" Alma whispered in my ear as we left the bar I had ?mistakenly? stumbled into. I shuddered with both fear & a bit excitement. I don't why ... Read full Story
Curious_billy 2023-05-07 7,350 Teen (18+) Amateur Cumshot Asian Ladyboy domination Homemade cum in mouth
100%
Erotic Dreams come true.
You start having intense erotic dreams — and the faces you see is one you don’t recognize but that feels familiar. Mandy was that girl that Chad had been dreaming of, the kind where to see her made a rush go through you like a hot flash. Chad had just broken off a relationship, and his sister war... Read full Story
Jon Paul 2023-05-26 4,887 anal Stockings Big Tits Cumshot Bareback Fetish Blowjob Guy Fucks Shemale small cock
100%
Linda and Cum on Heels
I was told by a cute guy today they would love to cum in a pair of my strappy heels............this was my answer to him. (I hope you enjoy what happened in what could have been unfortunate circumstances) Actually a person did. I had picked him up from the Lincoln University area and we went off ... Read full Story
Linda Tiffany Vista 2024-05-07 2,165 Stockings Crossdresser Amateur Blowjob blonde
80%
Me And Two Shemale Lovers
The ad in the local “underground” paper said “2 hot she-male lovers looking for inexperienced open-minded male for exciting new encounters….” It added a few brief descriptions etc. I thought to myself. “Why not, you’re open-minded and adventurous?” So... Read full Story
shemale lover 2011-08-09 6,546 anal sex shemale oral
100%
Erin and the Shemale
Erin was up bright and early on Friday, getting a good hour jog into her schedule. She didn't have to be in class until two hours from now. As she was jogging, earlier male joggers had passed her by with their eyes directly on her bouncing melons. Even wearing two sports bras and two regular bras we... Read full Story
shemale lover 2011-08-24 4,747 shemale Big Cock oral
95%
Interesting Suprise
This all happened several years ago when I was in the Navy in San Diego. One payday weekend I was in a partying mood so I thought I would head down to Tijuana for some fun. Being I was about 20 at the time I headed for one of the clubs where a lot of the college kids hung out hoping that I might g... Read full Story
bjw_6 2011-10-23 7,686 suck Bareback Shemale Fucks Guy Guy Fucks Shemale 69
100%
Shemale Seduction - The Surrender
I cannot remember what drove me to it. Cruising bars for sex had become a habit. Success can do that to you, but even steady success make you yearn for something different. I looked at her from across the bar and acknowledged her stare. She definitely looked hot and hungry, with eyes that seemed to ... Read full Story
shemale lover 2012-02-03 4,751 anal cum fingering
100%
Back to School
It all started the day John got a letter in the mail; it was an invitation to his school reunion back home. John was proud of what he had achieved in his life; he had a good job and a house. The only secret John had was that he was a closet cross dresser; he loved to feel feminine from time to time.... Read full Story
shemale lover 2012-02-09 3,927 Shemale Fucks Guy orgy cum swallowing
83%
Tgirl Shemale porn cinema slut
As you know I'm very much a normal living sort of TGirl, cooking, shopping, cleaning, just day to day stuff like everyone else...I haven't started baking cakes for the local Women's Institute or joined a knitting circle yet, but I'm sure you get the general idea!! Sometimes, however, I get the ur... Read full Story
shemale lover 2012-05-07 4,730 shemale oral sex bikini heels
100%
Olderman and mature crossdresser Part 2
We left the park and drove to his house which was very nice.I knew he was wealth when he picked up due to his car was new jag. He fixed me drink and we sat on his couch and kissed and made out an heavy petting.He kissed my neck driveing me nuts as he did I rubbed his cock thru his pants which was ha... Read full Story
shemale lover 2012-05-26 3,983 Crossdresser anal sex Cumshot oral sex Mature cum swallowing