Sort by
Relevancy

Free Stories

100%
My shemale GF Part 5
If you read my last story, you know that Ashley said she was going to dominate me, well that's exactly what she did. So today after work I went back to Christy's place not actually thinking she was going to fuck me. Christy was home before me and asked me to clean up, which is the universal sign ... Read full Story
shemale lover 2012-07-22 3,172 anal sex facial cum swallowing sissy
84%
Alex to Alice Chapter 1
Everything had started off simple enough for Alex. He had met Elena at a bookstore while he was researching for a college paper. She was quite the vision at 29. She stood a respectable 5' 8" with a voluptuous body. While slightly plump, she maintained her hourglass figure and filled out quite n... Read full Story
shemale lover 2012-09-25 4,865 Cumshot domination oral sex
78%
Transsexual Son / Daughter
Now I’m a 51 year old mother of one and watching my Daughter who’d been once my son putting on that very nice silk blue bra from Harrods department store and lift up her huge breast in to them made me so wet. Now seeing my son all now transformed and transitioned in to a beautiful woman ... Read full Story
shemale lover 2012-10-16 5,880 Fetish fingering Sex Toys
100%
Who's The Sissy Now?
Like many people, I was bullied in school. I was small, slender and effeminate and, as a result, was often called gay, queer, fag and sissy by school bullies. The fact that what they said was sort of true just made it closer to the bone and more painful to hear. Like many teenage boys, I was going t... Read full Story
shemale lover 2012-11-14 7,173 shemale facial oral sex
75%
From Husband to Castrated Sissy
"Oh my god!" My wife looked up over the muscular shoulder of the huge black guy nailing her on our bed. Her long tanned legs wrapped around v-shaped torso. "Hi honey. What are you doing home early?" "Kelli what the fuck's going on here?!" At that, the black guy... Read full Story
shemale lover 2012-12-02 43,584 Fetish sissy
87%
Encounter with a dominant shemale
One night I was feeling really horny. I just came back from the gym and I wanted to release and relax. I then began my search for some fun on the personal ads section. I have always been into shemales especially verse aggressive ones. I found this one particular post about Asian bottoms. I was c... Read full Story
SecretAznMan 2013-06-28 48,478 Cumshot Shemale Fucks Guy Big Cock Lingerie ass fucking ass licking big boobs
93%
CD Jinn College Experience
So being a secretive cross dresser is very difficult to do with roommates. I only dress when I know that no one will be around for hours I check class schedules and ask what everyone is doing all the time so I know when my chances to dress are. I was planning on dressing over the weekend. It was p... Read full Story
Jinn.V23 2014-03-27 6,181 Crossdresser Cumshot ass fucking domination cd
88%
Tipping Point -- Chapter 1: Blow by Blow
Chapter 1: Blow by Blow October 12th Thursday evening. Tick, tick tick... the minutes pass by while Nick lies on his back, staring at the white ceiling fan that hovers above. He raises his head, bats his eye lashes, and yawns. His long, wavy, auburn hair falls down his back with small curls. ... Read full Story
Danielle Pillory 2015-11-24 5,586 anal shemale domination spanking submission
56%
Big cock shemale from Pune, India
I just saw her profile on Planet Romeo, her name is ID is Kaynat / Muskan. I saw her photos and got attracted to her. I am always a big fan and lover of Shemales or TS. I called her and fixed appointment by negotiating with her for 2500 INR. I went to meet her, she stays in a condominium in ... Read full Story
Stud4Shemale 2017-05-22 96,534 Big Cock Asian Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
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 4,477 Amateur Bareback Big Cock cum in mouth
100%
Maid in waiting.
This is my version of an incident that happened to me a few years ago. I live in a remote area of Scotland but I attended University in Edinburgh, the country's capital. I made friends then with a couple who were Bi and into swinging. They had arranged a sex party and I was invited. I was helping th... Read full Story
Missy47 2020-08-17 4,586 Amateur Cumshot cum in mouth Crossdressing bukkake
100%
Gemini Sluts and Gang
My good friend Renee and I had set up a double date gang bang for tonight now that she was finally out of the closet and ready. She has decided that life is too short to remain in the closet and miss out on all the fun. Renee and I have so much in common. Besides loving sex, we both have a fetish f... Read full Story
Regina10 2021-04-09 4,709 Group Sex Big Tits Cumshot Bareback Fetish Blowjob blonde gangbang Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth
94%
Very Clean Bad Boys
This weekend, I got myself set up with a little garden in the courtyard-style patio of my new apartment. And while I was getting everything repotted and boxed and hung, I learned to my chagrin that it’s quite possible to work up a sweat even in a 4 x 4 space. So by the time I was even halfw... Read full Story
shemale lover 2015-07-15 5,421 ass shemale oral
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 19,379 tranny Big Cock jerking off
66%
Charisma & Tiffany Part 4
While bathing her in the shower stall, before pissing on her and making her drink the warm, golden beverage she’d poured from her bladder, Charisma had planned to fuck Tiffany in the ass with the aluminum Little League baseball bat she’d brought into the shower stall with her for that ve... Read full Story
shemale lover 2011-09-02 3,302 shemale domination
100%
A Fairy Tale Part 2
=-=-Chapter Six-=-= I woke up sometime later and I was feeling better, even a little hungry actually, and I wanted a shower and I needed to pee and...I cocked my head as I heard the unmistakable sounds of Mistress Stacy's bed moving. She had a large one, king sized, with old springs or somethi... Read full Story
shemale lover 2011-12-06 6,958 Creampie Big Cock ass fucking
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 4,104 Shemale Fucks Guy orgy cum swallowing
80%
Becoming Her Bitch Chapter 2
I can feel the toe of her high heels sliding under my balls. I'm on all fours positioned right over it. The big black cock is lubed up and pressing against my back door. I try to relax. I try to let it in without clenching up. It'll hurt if I clench before he's in all the way. "Don't worry a... Read full Story
shemale lover 2012-03-17 3,221 sucking Big Cock cum domination
75%
Shemale gang-bang
I have been surgically modified by my mistress I have a small 6 inch penis (functional) I have no body hair except for my ‘pussy’ My anus had been surgically loosened for better sexual performance (can now tightly accomodate penises 2.3 inch diameter and 9 inches long) I have large... Read full Story
shemale lover 2012-03-26 4,895 Creampie gangbang domination
70%
SissyRayG at the Roadside Reststop......
Last year I was traveling by car on business between Saskatoon and Regina, Canada. I was looking for a roadside rest area to use the washroom. I had all my sexy lingerie with me and hadn't had a chance to wear it for days as had been way to busy at work. I saw the roadside rest area I was looking... Read full Story
shemale lover 2012-07-03 5,649 anal Bareback sissy gloryhole
100%
A Tranny Virgin No More
Fantasy became reality for my gal, Tranny G. She has finally started to come into her feminine persona. She has more confidence, is buying more outfits, and when she leaves HIM at work, she comes home and dresses. She starts with wearing short skirts and cami's, then sexy lingerie at night. She bega... Read full Story
shemale lover 2012-07-10 3,400 Cumshot oral sex sissy
87%
Feminized By My Mother Chapter 2
My mom was staying in as were Jen's parents so we parked on a dark road and made out while I fingered her. Her panties were absolutely drenched when I was finished, and she rubbed her hand inside them and used her pussy juice to jerk me off, I spurted all over my pants and she laughed. "I ho... Read full Story
shemale lover 2012-07-24 13,421 sucking Fetish fucking sissy
0%
A Working Sissy Girl
I look up at my boots. Cute! Received delivery just day before yesterday, my boy friend hasn't even seen them yet. He'll like them, know he will. 3" spike heel ankle boots, very shiny patent leather, I look up at the one on my right foot. I run my hand down the thigh-high lace top seamed nylon ... Read full Story
shemale lover 2012-07-29 3,994 Cumshot oral sex sissy
75%
Intro to a Dream Made Real
Jim had known growing up that he enjoyed bi-sexuality. But he had never found a man attractive the way women were to him. For example, he never found himself wanting to kiss a man, but he liked holding a hard cock as much as he enjoyed touching a wet pussy. He really enjoyed sucking a dick as much a... Read full Story
shemale lover 2013-01-22 5,933 hardcore sucking domination bondage foot fetish
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 32,176 first time Creampie Shemale Fucks Guy ass licking virgin
76%
Sissy Ghetto bitch part 1
-The Guys 4 ghetto guys was inside a porn site looking at random sissy babe pictures when they accidently found a picture of someone they know. Like every album they clicked it that specific one with a tranny dressed so girly with mouth open. The guys had such a stone hard erection by watching al... Read full Story
shemale lover 2013-06-01 6,386 suck Big Cock cum jerking gangbang doggy style Interracial cd
89%
Bookstore sissy slut
My name is dollie I love to be a girl and being very petite and pretty long black haired its easy for me too feminize. And until now I wouldn't go out, dressed up, sometimes a quick walk around or a short drive but nothing real. And one time in college I walked around the campus. Anyway I ignored al... Read full Story
shemale lover 2013-06-10 8,306 Crossdresser anal sex suck ass licking rimming cd
93%
First time
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... Read full Story
shemale lover 2013-07-20 5,164 first time Cumshot oral sex Guy Fucks Shemale kissing
88%
Best booty i ever had
there is a certain part of the big city where the community partys everyday of the week called boys town i worked in the area and never knew but what i did know is i had a fetish for an extremly large ass i love big bootys and desired a tranny after watching shemale videos this didnt happen until i ... Read full Story
jrryder 2013-12-08 4,700 tranny Bareback Blowjob Ebony doggy style Guy Fucks Shemale
96%
Shemale fun
Recently I've been chatting with a very feminine and beautiful shemale named Lisa. We've been trading photos and dirty talk over chat lines and emails. I've always fanatsized about a cick with a dick and unexpectedly the opportunity came that we could potentially meet. Being married I had to conc... Read full Story
shemale lover 2014-11-25 10,363 tranny suck Creampie Shemale Fucks Guy ass fucking 69
80%
Shemale fun
Recently I've been chatting with a very feminine and beautiful shemale named Lisa. We've been trading photos and dirty talk over chat lines and emails. I've always fanatsized about a cick with a dick and unexpectedly the opportunity came that we could potentially meet. Being married I had to conc... Read full Story
shemale lover 2014-12-03 6,669 tranny suck Creampie Shemale Fucks Guy ass fucking 69
87%
Making of a new Sissy
I became a Sissy at the hands of a friend of my parents. When they worked long hours they would normally ask a friend to check in on me to see if I was OK, despite the fact I was at this point 18. One time it was Tom who came over. He was mid 40's, an old friend of my dad's. A guy who ... Read full Story
sissychloe 2016-05-09 10,010 suck Blowjob crossdressing cd sissy
81%
My First Sissy Meet Up
I had posted an add on craigslist asking people to let me suck them off at my place. After sorting out all the answers that I got I found a guy, John, that was incredibly eager, we agreed a time and date. The day came and I woke up so nervously. But I was determined to not let it show so I got... Read full Story
Felicia Smith 2016-06-08 12,335 Crossdresser Big Cock cumming cd sissy
73%
I love Pocahontas First encounter
I love Pocahontas First encounter You seen the video of her wearing white with her huge ass bouncing around on daytona beach,guys are stopping her and at the end of the video a couple guys have her and her friend in their room dancing,i was in Daytona celebrating my birthday that same weeken... Read full Story
NastyopenmindedDick 2017-08-03 8,496 Ebony transsexual Guy Fucks Shemale big ass booty
71%
Alleyway Adventure
I was on my way home from school and this girl in those tight yoga pants and a shirt that showed off her huge boobs taps me on the shoulder as I walk past her. "Want to have some fun?" She asked smiling. Nodding I said "Yes I would love to." Taking my hand she lead me down the st... Read full Story
HornyCummer2344 2017-09-12 4,545 Big Tits Cumshot Blowjob Big Cock Lingerie Guy Fucks Shemale
83%
Uncles Ranch
My Uncles Ranch Its late May and school is getting out for summer break finally next year marks the start of college but who cares about that. I’m excited to do the basic summer fun like hangout with my friends go to movies and of course get in touch with my shemale side. When I get home my parents... Read full Story
cdsissy18 2018-03-02 2,416 sissyboy sissy slut sissy crossdresser
100%
Shawshank affair
Courtrooms can be a scary place. They smell like older leather, the wood paneling has been polished with oil and each sound penetrates your body like a loud smack from a cap pistol, which echoes in the forest, especially the gavel smacking on a block from the Judge. I felt strongly that I would be f... Read full Story
Jon Paul 2018-08-20 6,827 Stockings Crossdresser Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Ladyboy 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 7,906 Shemale Fucks Guy redhead Guy Fucks Shemale cum in mouth
95%
Best session with a T Girl
I like T-Girls. Recently had a chance to go to Costa Rica for work. While I was there I decided to see what Costa Rica had to offer in this department. There is quite a good amount of girls to select from. I started texting this Tgirl and we set a time. I got ready and headed over. It was a Hotel th... Read full Story
horny.hiker 2019-04-30 15,041 Stockings Masturbation Creampie Shemale Fucks Guy Lingerie rimming Ass to Mouth escort ts no lube anal fuck just saliva
95%
First time
Hi, my name is Sandra. In fact, I'm not exactly a girl, but a CD. Even as a child, I felt different and I used every opportunity when I was left alone in the apartment to dress up, to put on women's clothes, to put on make-up. In time, I started watching porn, as did all my friends. But, unlike them... Read full Story
cd Sandra 2021-10-13 5,954 Stockings Teen (18+) Small Tits Crossdresser blonde Guy Fucks Shemale
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 4,707 Stockings Crossdresser Blowjob Big Cock Guy Fucks Shemale Interracial public sex
100%
Train adventure
A new story from me and be patient with my english ;). You can read my other stories here: https://www.ashemaletube.com/profiles/176291/stories/ It's late in the evening, I'm standing at the train station and like every Sunday I take the last train back to t... Read full Story
Marten1201 2023-03-21 5,858 Cumshot Shemale Fucks Guy Blowjob Big Cock Guy Fucks Shemale Ass to Mouth cum in mouth
100%
The Three of Us
Imagine you are a lonely person on the inside, and just wanting all your life to be loved for who you are. Holli Artigas, was just that person. Wondering whether her obsession with Jon Silva, a football star, was from a casual encounter, or was she truly fond of him? Growing up in the Sao Paulo, ... Read full Story
Jon Paul 2024-04-28 3,764 anal Creampie Shemale Fucks Guy threesome Shemale and Girl cum in mouth double anal shemale fucks female
100%
Becoming a Chrissy - Chapter 2
I had always felt like I had a hot body for a girl. I was naturally blonde and smooth; I guess I had been blessed by my parents’ Scandinavian genetics. My pubes were always just a small fuzz—easy to shave and keep a clean bikini line. Same thing with my armpit hair. And my ass? Completely smooth and... Read full Story
mindlessrobot45 2024-05-13 4,175 Crossdresser gangbang Shemale and Girl cum in mouth shemale fucks female teen (18+)
40%
See Me At Shemale Cam Tube
I was dressing when I heard a new e-mail arriving. "You're hot as hell on Shemale Cam Tube", he wrote, "Wanna meet me 4 lunch? Promise to be a gentleman!" It was cute, especially coming from such a skinny guy. I'm a big girl - over six feet, with strong legs and huge breasts whic... Read full Story
shemale lover 2011-08-09 6,676 asshole Blowjob shemale
75%
by a Shemale Part 3
I woke up the next morning not sure what just happened was real or if I just dreamed it than I looked around. I was laying naked in this mammoth canopy bed the bed spread and canopy were both pink and feminine and I realized it wasn't a dream I couldn't believe I was begging to be fucked. ... Read full Story
shemale lover 2011-08-29 4,621 Cumshot asshole fingering
66%
Charisma & Tiffany Part 2
Tiffany's six cocks filled Charisma's six cunts and, although the sorceress was on top and, therefore, able to move faster and with more force and agility than the supine shemale, Tiffany, nevertheless, felt overwhelmed by the welter of sensations that had, as it were, laid siege to her consciousnes... Read full Story
shemale lover 2011-09-02 3,151 asshole shemale domination
100%
Charisma & Tiffany Part 3
Tiffany didn't hate Charisma, not exactly, although, the more she thought of how the sorceress had treated her, how she'd abused her, the more the shemale fumed. Not only had Charisma changed her sex, from shemale to female (and back again, thank God), but she had also equipped her with a half dozen... Read full Story
shemale lover 2011-09-02 2,791 shemales pissing domination
69%
From Mob to Shemale
Two years ago, I was a member of the Ciccio family in Chicago. I wasn't very high up in the organization, because I wasn't Italian. I had made my way up through the ranks, however, and was making a pretty good living. I had everything I wanted, got all the girls I wanted, and did just about ... Read full Story
shemale lover 2011-10-29 10,728 orgasm facial oral sex
100%
Jeremy's School Bully
Author's Note: Jeremy is an actual person that requested that I write this fantasy down for him. He was specific about the situation, but left the rest up to me. This is a story with a very strong 'dominance' scene and should only be read by person's who find those situations erotic. Nothing new to ... Read full Story
shemale lover 2011-11-15 12,837 anal big dick shemale
0%
Mike and Chris Together
Mike's sex life had taken a definite series of turns for the worse. When he called one of his favorite partners, Stella, she apologized for not returning his earlier calls, and told him she had been very busy lately. "I'm really sorry, Mike. I've had some great times with you, and I will alw... Read full Story
shemale lover 2012-02-07 5,393 anal sex Creampie Shemale Fucks Guy Guy Fucks Shemale
94%
SheMale Encounter
“Promise not to fall in love while you’re away?” Lana asked as she wrapped her arms around me. “I’ve told you several times already,” I snapped at her. I had begun to get more than frustrated with her. “This is just a business trip and nothing more, besid... Read full Story
shemale lover 2012-02-20 9,581 first time Shemale Fucks Guy cum squirting
100%
A Night to Remember
I have always had a strong fetish for stockings, garters, sheer panties, heels and other sexy lingerie. I've always required my women to dress this way for me. Even when I walk through the lingerie section in a department store or Fredrick's and I can't help but want to look at the panties and stock... Read full Story
shemale lover 2012-04-26 4,330 anal Fetish oral fingering domination Sex Toys
100%
Fantasy to Reality
I faded in and out of consciousness. My body was numb and I waded through a sea of words and images that filled my mind, struggling to focus on anything specific. Slowly I began to wake but my eyes did not open and my body remained numb. I searched for my memory, I knew it was there but I couldn'... Read full Story
shemale lover 2012-07-02 4,319 Cumshot Fetish deepthroating crossdressing
88%
Feminized By My Mother
Hello. My name is Dan. I'm doing okay, you? I see. Well if you are going to be listening to my thoughts please keep the volume down, I am trying to think. Some things are going on that have got me very mixed up and I have to concentrate. Like most overly complicated things in life, a woman is inv... Read full Story
shemale lover 2012-07-24 67,901 Fetish shemale oral feminization
100%
Property To Be Pimped
It had been weeks since I'd brought to light my idea of my wife, Suzie, strapping on a big dildo and taking me dressed as Desiree, the Hot to Trot Transvestite. While at first she teased me with possible participation, it never came to be, despite me bringing it up on several occasions. She really d... Read full Story
shemale lover 2013-01-17 7,540 Stockings Crossdresser sucking dildo Interracial