Sort by
Relevancy

Free Stories

100%
Caught Cheating Chapter 2
By this time, Hailey had taken the bus home and was punching in the code to her apartment building when her phone rang. Removing it from her purse, she answered it. Her friend Samantha was asking if she could go to the mall tomorrow. Hailey said sure but told her that she had to be back before 6 o'c... Read full Story
shemale lover 2012-10-07 4,223 Fetish oral sex cum swallowing jacking
100%
Ana in Action
I had fantasized about him for months. I just wanted to know what it was luck to have him pulsing inside me, to feel his body pressed against mine in sheer lust. I just had no idea that it would actually come about and that my wife would be the hook up. You see, Jim has been one of my wife's drinkin... Read full Story
shemale lover 2012-11-23 3,022 threesome cum fuck oral
66%
Anal Queen
Amanda fell to her knees in the darkened theater and slowly unzipped my pants. My cock throbbed. As she pulled down my underwear, I felt my manhood spring forth. Amanda took the whole sausage into her warm, soft mouth. I could barely see her face in the darkness, but I could feel her between my l... Read full Story
shemale lover 2012-11-24 6,165 tranny anal sex Cumshot cum swallowing
100%
Proud To Be A Sissy Chapter 4
As usual, Mr. Clark was sitting in his recliner when I went into his house. "Good morning daddy," I beamed kneeling before him. "Morning," he grumbled but smiled and said, "more like afternoon." But you do look sweet." "Thank you daddy," I rep... Read full Story
shemale lover 2012-12-24 8,155 Cumshot sucking Big Cock gangbang bukkake
86%
Hotel Heaven or Nightmare
You've enjoyed a relaxing bubble bath, you're smooth skinned and perfumed. You dress with your new purchases, Gio seamed stockings, leather mini skirt and Carvela heels with sexy peep toes. You take time to apply your make up while you contemplate what the evening will hold for you. There's nothing ... Read full Story
shemale lover 2013-03-12 5,986 sex toy Crossdresser Cumshot Big Cock Lingerie
92%
First time being dressed as a woman
I'm a 42 year old married bisexual guy, slim built, average height and shaved below. Ive had a few encounters with other men but none dressed as a Woman. Ive had fantasies for years about wearing women's clothes and make up. Unfortunately I haven't had much opportunity for either, that was until a... Read full Story
shemale lover 2013-04-15 6,957 Crossdresser suck facial ass licking cd
84%
Young sissy goes for a little shopping... caught
May be first a little introduction? My name is Sylvia and I love women's clothes! I like panties, stockings but most of all, I adore high heels! just love them! That feeling when it becomes higher and I feel so sexy and feminine! And you know what? I'm a total slut, I love to be humiliated,... Read full Story
shemale lover 2013-08-14 17,575 Stockings suck oral Lingerie public cd
85%
Business trip
A few months ago I had to go on a business trip for some additional training for my job. I had to go fly to Georgia for the training. I flew in and got my rental car and was headed to the hotel. On the way in I passed an ABC store. I decided to get a bottle of whiskey since I was going to be in... Read full Story
Play1802 2014-07-08 5,943 tranny anal sex suck ass fucking
92%
My Life as a Shemale Part10
Suzi and I started spending more time together as the weeks past by. I think she might have fallen in love with me but I knew little of these things. My focus was on my studies, I found that I excelled in school and it pleased me to do good. She had heard about me possibly liking sexual arousal thro... Read full Story
shemale lover 2015-02-27 3,173 tranny Creampie cum ass fucking spanking whipping
52%
My neighbor
Peter invited me up to his place to show me the lady I saw through my window. She was a beauty with very sexy lingerie and silk stockings. Her tits were large And I could see them under her transparent top. It didn't take long before I realized she was Peter, only beautiful and sexy. Sit and... Read full Story
warmcream 2016-04-05 5,450 Big Cock cock sucking crossdressing cum sucking ass sucking
63%
A Slice of Life - Ch. 1
Written by Nobody Home. All comments and feedback welcome! 1. It is dark out, night descending upon a wintery, snowcapped city backdrop. Cold against the windowpane, I feel my head shoved into it and my hand makes a streak against the glass. My would-be attacker tears my panties off of my slen... Read full Story
Nobody Home 2016-12-20 5,196 ass fucking cumming Guy Fucks Shemale cd sissy
85%
The Gang
I had always thought of myself as female in spite of the fact that I was born with male genitlia. Even in my earliest memories where I had witness sex, I identified with the female in the relationship. As a small young child, I had always longed for womanhood each time I heard a woman sing or especi... Read full Story
Regina10 2020-06-29 8,911 Group Sex Cumshot Blowjob Big Cock Ebony gangbang double anal
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 5,207 Stockings Crossdresser solo Amateur Cumshot Masturbation Fetish Lingerie Sex Toys Homemade
100%
A true first time.
I want to preface this reiterating that this is a real story about my first ever experience with a shemale. It's a memory I will hold forever as it was everything I could have hoped for and, as I may share in the future, lead to other experiences, too. A little history of before the first meet ac... Read full Story
Gtaaddict3 2023-11-21 8,576 first time cock suck Blowjob shemale Big Cock trans oral fantasy virgin escort big first time
89%
He caught me in his wife's cloths
I do odd job's and I was about to do one for my wife's best friend Tina and her Husband Phillip. I went over and looked at the job. I told her it would take several days and that I could do the work while her and her husband were at work. That way I wouldn't be in anyones way. Well the first day of ... Read full Story
shemale lover 2014-06-15 10,077 sucking shemale pounding
86%
Two hot CD lesbian sluts share an intimate moment
Her name was Kelly, we had met online in one of the gay chat rooms I like to frequent and for the next couple of weeks we had developed a friendship, exchanged pics and fantasies and I was really, really into her. we had a lot in common, more than just the mere fact that we were both gay CD’s ... Read full Story
shemale lover 2014-06-21 4,576 shemale cum oral
85%
Unforgettable First Time
I am in my late thirties and have known for a while that I have a sexy body. I'm 5'11", slim and athletic with little cherry butt and shapely legs. A lot of women have told me my body is sexy. A few men have mentioned it too. Sometimes I get photo-snapped at the pool or the beach. I've been luc... Read full Story
shemale lover 2016-05-06 10,171 cum oral deepthroating
89%
Being my Master’s Panty Slave
I was standing where he had ordered me to, with my legs spread slightly, bent over with my hands on the bed. I could hear him moving behind me but I kept facing forward. He had already told me he had something to plug up my ass with so I knew what was coming but had no idea what he planned to stic... Read full Story
shemale lover 2018-02-18 8,790 asshole shemale cum
100%
A Different Kind Of Lust
This woman he is with is not really a woman, but he still feels the urge to give her the best sex ever. She is pretty, long blond flowing hair, long sexy legs that she can wrap her legs around him. Her hands are soft and gentle, like a woman's hands should be. Her body is slender and petite. Her ass... Read full Story
shemale lover 2011-09-11 2,254 anal sex licking cum
50%
The Unkindest Cut of All
Darren's cock was huge, bigger, longer, thicker, harder than it had ever been, a living testament to Lindsay's beauty. The actress was even lovelier in person than she was on film, and Darren had seen a lot of her films. In fact, he'd been in two of them himself, the leading man to her leading lady.... Read full Story
shemale lover 2011-09-28 2,870 Big Cock orgasm anus
100%
Connie at an Adult Bookstore Part 2
Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. * In the previous c... Read full Story
shemale lover 2011-09-30 8,591 Big Tits Blowjob deepthroating
50%
Healthy Behavior
"Uhh…is Mr. Stanford around?" "One moment dear…ooh, damn heels. Makes it impossible to walk through doorways. Here I am ma'am. So, did the maid get you here alright? Hello? Earth to…" "I can't believe this…" "Oh, the heels? Yeah... Read full Story
shemale lover 2011-10-19 3,956 Big Tits transsexual oral
100%
Mel - Sexy Olderman
Mel is 66 years old and is in my musical orchestra. he is handsome with a great personality. he is married but his wife is ailing ,so i dont think he gets much action!he is a horn player an i in the percussion section.mel an i joke a welot an he sometimes jokingly says i have a nice ass! he has beco... Read full Story
shemale lover 2011-10-25 2,694 Cumshot Big Cock oral
100%
How I Became a Tranny Whore
When I was 30 with children at home I would get dressed in the bedroom. When it was time to leave the wife would take the children off for ice cream and as soon as they were out of the drive way I would head for my car. Of course when I returned home the children would be a sleep. The plan worked fo... Read full Story
shemale lover 2011-11-07 4,633 anal Cumshot cum swallowing
100%
Mistress Jasmine made me a slave forever
I should have been honest. I mean I should have known that lies have short legs and now they had caught up with me. The worst was I had not only lost my place in my bed but had also lost my place with my wife. Somebody else occupied these places now. Let me tell you how everything went. More ... Read full Story
shemale lover 2011-11-26 11,441 Big Cock orgasm domination
100%
Becoming a Cock Worshipper Chapter 2
After sucking Ray he let me use his shower to clean up. He led me upstairs to a rather luxurious master bath, with an enormous marble tub, with expensive looking twin shower heads. Before showering I paused to admire myself in the mirror: I was stunned by my appearance, my lipstick and eyeshadow wer... Read full Story
shemale lover 2012-02-29 2,597 Fetish cum domination throatfucking
100%
Becoming Marie Chapter 2
After my encounter with Kevin at his office I knew that I wanted more. I had my own place and had started to build up a nice collection of lingerie which I would often wear while wanking to my slowly built up collection of porn. This was before the age of internet so it was sometimes hard to get por... Read full Story
shemale lover 2012-03-22 3,203 anal sex Creampie cum oral Lingerie
85%
First Time with she-male
For as long as I can remember, I've preferred my chicks with dicks. There's something about a sexy babe with perfect makeup and hair and a cock that just turns me on. Maybe that makes me a pervert - I don't care! I remember I was just out of high school, 18, the first time I made it with a tranny. S... Read full Story
shemale lover 2012-04-29 4,686 first time Cumshot shemale small cock
87%
Caught by my Sister Chapter 4
I woke up late on Sunday with the distinct taste of cum still in my mouth from the night before. For the life of me I couldn't even remember how many cocks I sucked at the party. I slowly got myself out of bed and took a long hot shower. It took me a long time to scrub all of the dried cum from m... Read full Story
shemale lover 2012-06-18 6,796 Cumshot Fetish Blowjob Lingerie
100%
Danielle Works a Saturday
It had been a few months since his wife left him. Well "ex-wife" as the divorce had been recently finalized. It was her choice; she walked out on *him*. She said she got tired of "Danielle", even though she was entirely responsible for Danielle's "birth" to begin with. ... Read full Story
shemale lover 2012-06-18 5,657 anal sex Creampie oral sex cum swallowing
100%
Birthday Surprise
My girlfriend and I have the same fetishes and interests for the most part. We both find latex irresistible. We love the site of a tranny with a big cock. Robbie knew everything about me. For my birthday she went well out of her way to make me happy. The date rolled around. I figured it was jus... Read full Story
shemale lover 2012-06-19 4,068 tranny anal sex Cumshot Big Cock
100%
Demoted Chapter 1
Monday I had been working in this office for a couple years, I was a floor supervisor had my own office and a few people under me. It was very easy and never had any trouble at all. I am also a cross dresser and I didn't know it but my story starts with a page I had on the Internet. I checked my ... Read full Story
shemale lover 2012-08-13 5,478 Crossdresser Fetish Lingerie
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 7,751 Crossdresser Cumshot Masturbation Lingerie heels
60%
The Pre-Nup Agreement
Several years ago one of Kellys' friends had a brother who was getting married in Reno and a bunch of us girls decided we would all get together for a wild weekend reunion. I unfortunately had several of my regular clients to see on Thursday and Friday afternoon and wouldn't be able to depart for ... Read full Story
shemale lover 2012-09-14 3,323 anal sex cum fingering oral sex deepthroating
100%
Brian and Bree, and Mitch Chapter 2
"What ever I want?" Mitch looked deep into Bree's eyes, she sheepishly nods up at him, "I've always wanted to please a man, I'm just glad it could also be my best friend." She replied, her voice trembling with nervous excitement, "Just give me ten minutes, and meet me in ... Read full Story
shemale lover 2012-09-20 3,388 anal cum fingering oral sex
83%
Discovering Amber
I have always enjoyed women's lingerie. From looking at catalogs to seeing girlfriends wearing it I have loved the look and feel of sexy, silky lingerie but for me it has always gone deeper. At 18 I tried on my first set of panties, oh my God that was wonderful! It was all downhill from there. Event... Read full Story
shemale lover 2012-09-28 6,190 Cumshot Fetish Lingerie oral sex
100%
Discovering Mistress Sarah's World
Chapter 1: Meeting Mistress Sarah Joe's heart pounded fiercely as he stood at the door to his Mistress's house. He did not expect to be so nervous at his first meeting with her. After all he had known her for over a year. Mistress Sarah had been gracious enough to allow him into her world. He was... Read full Story
shemale lover 2012-10-01 5,879 Fetish domination cum swallowing feminization
100%
Discovering Mistress Sarah's World Part 7
Chapter 18 A Life Changing Decision Sunday morning was not much different than the day before for Josie. He woke-up on the floor outside Mistress Sarah's bedroom, dressed in a silk night-gown and his cock was hard and aroused when he awoke. Just like Saturday morning, he crawled into the bedroom.... Read full Story
shemale lover 2012-10-03 5,433 cum domination oral sex feminization
66%
Discovering Mistress Sarah's World Part 9
Part 9 -- The Final Part Chapter 23 Leaving Work Josie's last week at work and concluding week of his normal life went quick. At work he spent time getting things in order for the next unlucky person to take over his job. Mentally he was already checked out of work. All he cared about was gett... Read full Story
shemale lover 2012-10-04 3,973 Fetish ass licking domination
100%
First time Tranny
Well this all happened about two years ago when i was 18 i always have had fantasies of having a cock in my mouth and ass but i wasnt attratced to men jusst the cock so i decided to find a shemale. i live in a small town and thats hard so i found one about an.hour away in the city. so i talked to he... Read full Story
shemale lover 2012-11-19 3,779 anal cum jerking fingering
94%
Taken Chapter 1
Georgia pulled her Mercedes out of the gas station in Albuquerque back onto interstate 40 heading east. It was a long drive ahead to Chicago. She hated traveling alone, that was for sure, but the move to the office back east made it necessary. It was either drive there or sell her Mercedes and buy a... Read full Story
shemale lover 2013-01-18 7,265 Cumshot Big Cock ass licking big boobs ass fingering
84%
Hypnotized, Maybe?
"You want to what?" "I want to try to hypnotize you. C'mon man, it's nothing worse than some of the other stunts we've done together." This, coming from Cliff. Sure, he's my roommate but sometimes I think he's plain crazy. "Yeah, and how many of them did you start? A... Read full Story
shemale lover 2013-01-23 14,291 Crossdresser sucking Big Cock ass fucking spanking
92%
Sissy schoolgirl and her black daddy
I can't believe this is happening right now. Here I am, a 16 year old white boy dressed in the sluttiest schoolgirl costume and makeup I have ever seen, being barebacked by an older, married black man. How'd I get so lucky?! Let me start at the beginning... It was summer time. As always I spent m... Read full Story
shemale lover 2013-06-22 39,693 Teen (18+) Bareback Creampie Lingerie ass fucking Interracial cd
95%
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 t... Read full Story
shemale lover 2013-07-21 11,760 anal sex ass licking oral sex kissing transexual
92%
The first sex! A dream for a little sissy slut!
We decided to meet at your place, I enter quickly and immediately go into the bathroom to get ready for our spicy evening. I'm already shaved and wearing stockings, leopard print panties matching bra. In the rush I'm doing makeup, I get dressed in little black dress, barely covering my bum! I put a ... Read full Story
shemale lover 2013-08-09 5,601 Stockings hardcore Cumshot Lingerie domination spanking
97%
Never Wanted To Be Your Girlfriend Ch. 02
So, after being made up like a slut, left glued to a pair of silicon breast forms, and caught sucking-off my best friend, I was pretty sure my day couldn't get any worse, but I had come nowhere near the end of my torment, as Michelle now had something else planned that I was probably not going to li... Read full Story
shemale lover 2014-07-21 9,492 hardcore Cumshot suck Lingerie ass fucking
84%
Shool teen crossdresser first time sex
I was just a young boy then, senior in high school, horny as hell and dreaming of my first gay experience since sitting in my new red lace thong and white lacy bra and discovering the one porno in the house everyone kept hiding from me. I guess they thought my s****rs panty drawer held no interest f... Read full Story
shemale lover 2014-11-21 18,754 first time suck fingering Lingerie ass fucking cd
95%
James's Cum Slut Part 4; Back to Boarding School
It was back to school time and I was back in the boarding house with James. We hadn’t seen each other all summer and were eager to relight the fire. But it was going to be hard. While we shared a dorm together, it would be hard maintaining the privacy. We had both packed items from my secondary ward... Read full Story
ATC97 2015-10-08 6,980 Crossdresser teen cd (18+) cum slut latex ts gangbang sex
90%
Lost Island
Bright light hit my eyes when I opened them after a long time. My mouth was full of sand, my toung dry and the taste of salt overwhelmed me. I was stranded. My boat sank in a terrible storm and my body was washed on this lonely beach of a tropical island. The sea was calm and there were almost no w... Read full Story
xgandalf 2016-05-04 6,342 sucking gangbang domination ass fuking Shemale on Guy
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 11,870 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
85%
The Sex Club
When I got divorced back in 1987 I was a very horny man that had not had sex in many years. I had always liked to dress up in nylons etc and learned long ago that I was Bi and liked cocks and pussy. When I finally got my own place after the divorce I almost always would lay around the house dressed ... Read full Story
crossdresser55 2019-09-11 9,817 Stockings Crossdresser Lingerie Sex Toys
100%
Liberty in Lisbon Part 3
After Olivia had so perfectly taken my anal virginity, we laid in bed cuddling, touching, kissing and her cum leaking from me. I had not been so lovingly caressed for such a long time. It was just perfect. She asked me how I was feeling. I think I said before that I don’t do deep and meaningful very... Read full Story
Rusty12 2020-09-16 3,362 Masturbation Shemale Fucks Guy Blowjob old-and-young 69 sucking
100%
Sissy Femboy Chrissy in Drag 2: At the Apartment
This is Part 2 to the article I wrote called "Sissy Femboy Chrissy in Drag at the Club." In that story I explained how I am 41 but look, feel and sound younger, that I shave myself smooth and like dressing in gurly panties and other female clothes to be a sissy femboy for older guys. A guy I met on ... Read full Story
Chrissy Tunnell 2022-02-03 3,613 Crossdresser Amateur Bareback Creampie Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature
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 2,979 Stockings Big Tits Cumshot Bareback Creampie Fetish Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth
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 4,313 Masturbation Shemale and Girl redhead Guy Fucks Shemale cum eating anal creampie couple & shemale
100%
Got my ass pounded in Miami by a tranny escort
Got my ass pounded in Miami by a beautiful tranny escort with a 10 inch thick cock. Years ago I was in Miami for a business trip. Four days just me in my hotel room. I decided to treat myself to some of the X rated channels that my hotel provided. As usual I went straight to the tranny porn.... Read full Story
My Shemale Attraction 2023-01-03 6,787 Amateur Big Tits Masturbation Creampie Shemale Fucks Guy Blowjob