Sort by
Relevancy

Free Stories

87%
My 1st time with a shemale
I always had the fantasy to be with a shemale, and today i gained the guts to go to a shemale. I saw the add in the newspaper and called, she was a brazilian (ussually the best ones are brazilian :) ) When i arrived to her apartement, she had a beautifull lingeri, and i noticed her big tits, my co... Read full Story
zongf2008 2014-09-02 4,850 first time ass suck shemale dildo
100%
BBC DOMINATION SISSY BLANC
Mon nom est Tim. Je suis un homme blanc de 23 ans. Il y a environ 6 mois, j'ai déménagé à Los Angeles pour essayer de devenir acteur, mais comme vous vous en doutez, je n'ai pas eu beaucoup de chance dans ce département. C'était début novembre, quand je suis allé dans le bureau de mon... Read full Story
Femboy 2021 2023-02-04 1,159 Stockings Big Cock Lingerie domination Guy Fucks Shemale Interracial Sex Toys
78%
A Little Girl Forever
Since I was a little girl I dressed in my sister's clothes, she knew it and she kept clothes for me and sometimes she bought clothes thinking about me. She was my accomplice and still is. When I was alone I dressed totally as a woman and I felt totally satisfied and realized as such, this included m... Read full Story
Mabel Cecilia 2019-05-06 8,025 Small Tits Crossdresser Amateur Cumshot Latina Masturbation Creampie Blowjob blonde Lingerie Shemale and Girl Guy Fucks Shemale Sex Toys Mature self sucking Solo Shemale cum in mouth double anal shemale + shemale
50%
Pa-mie sex-agénaire
Luxure frénétique d’une pa-mie sex-agénaire; entre rêve et réalité Je n’avais jamais fantasmé de mec viril, même après avoir offert ma virginité; mais à une fabuleuse sissy. Avant mon Ѐre, mes préférences de fantasmes étaient toujours avec des lui-femme glabres, idem concernant mes relations d’aprè... Read full Story
hippocampus_171 2023-07-09 840 anal Amateur Group Sex Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy Ass to Mouth
85%
Becoming a Shemale's Bitch
I just got into town and spent the whole day moving in and cleaning my new apartment. I didn't have much furniture but the place needed a lot of cleaning. I saw their was a bar a few blocks away from my apartment and decided to go out for something to eat. It was around five o'clock when I walk... Read full Story
metamafia 2012-12-21 118,753 hardcore Cumshot sucking bdsm domination
60%
A real cd explains what cd on cd sex is like
A lot of "strait" guys love shemale porn.I was one of them.Pre-internet I discovered shemale porn but it was hard to find.I had girlfriends but the sex was never great.like many i was more concerned with cumming to soon than actually enjoying myself.Plus,as a porn watcher my fav was anal.M... Read full Story
shemale lover 2012-09-11 3,973 Sex Toys cd shemale porn
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 34,023 Big Tits shemale Big Cock Lingerie domination
90%
DISCOVERING BLACK COCK
To the greater Boston general public it was simply a small little known quite private night club located in the back part of Roxbury called The Black Rooster Bar. While in local Gay Community circles, insiders called this private by membership only pub, THE BLACK COCK CASTLE! When first learning... Read full Story
CD DIXIE IN NH 2016-05-10 10,220 Big Cock cumming sperm ebony cock
50%
lust of a sex-agenarian nana-pops
Frenzied lust of a sex-agenarian nana-pops; between dream and reality I had never fantasized of a manly man, even after offering my virginity; to a fabulous sissy. Before my new Era, my fantasy preferences were always with glabrous he-she’s, same about my relationships after… BUT BUT BUT… My last t... Read full Story
hippocampus_171 2023-07-09 4,698 anal Small Tits Amateur Group Sex Masturbation Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy
80%
My Lesbian Shemale Experience
Me and my friend Sarah was driving to Calfornia , for Summer Vacation. SO we packed our bags , and sat them at the door , and we were ready to go , and then my friend Sarah had to go pee, man was i mad , when she said that, because i just wanted to hit the road. so i waite until she was done, and th... Read full Story
shemale lover 2011-08-16 3,484 pussy shemale fingering
0%
The orgy with a shemale
I had to move to Japan back in the fall of 2004 and lived in Tokyo in a 3 room apartment.I could not pay all of the rent so I lived with a female school teacher age 27 years of age and japanese.Her name was Miki.There was a one more girl who was friends with Miki ,I never seen much of her.Her name w... Read full Story
shemale lover 2011-08-29 5,163 Big Tits asshole Big Cock
92%
All Night Forced Sex Part 4
When I woke up all I had on was very small running shorts that had a slit up each side and a t-shirt. The shorts were unable to contain my hard-on so I let it stick out the bottom. No one was around and it felt nasty hot. I snapped out of my daze and began to panic just as she opened the door. &q... Read full Story
shemale lover 2011-10-10 14,431 asshole shemale cum
92%
The Girl Next Door Ch. 02 by derezzed ©
Chapter 2 – Taking the Next Step Into Depravity Michael hardly got any sleep that night. When he did his dreams were filled with images of Jenny and her large penis. He tossed and turned in frustration. As he rolled over for what felt like the thousandth time he was blinded by the sunlight that h... Read full Story
StevelovesTgirls 2019-06-11 12,538 Amateur Big Tits Blowjob Big Cock Guy Fucks Shemale
100%
Being Shemale Part II
After sometime the driver left. Night Two I was again ready by 10 Pm as usual wearing make up and sexy night outfit. My push up bra helped my breast look very attractive looked perfect with my slim body I was standing as usual in the balcony around 11 PM and the driver stopped by again.... Read full Story
babydriver 2024-06-04 2,353 Amateur Shemale Fucks Guy Big Cock Asian Ladyboy Lingerie domination small cock big ass Frottage sissy femboy
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 10,513 orgasm facial oral sex
50%
Spy Girl
Vicki stood in the dark doorway as she watched her mark, Ivan Patrinkov, approach up the empty street. There was no way he would be able to see her where she stood in the shadows. She wore a skin tight leather jumpsuit with black low-heel boots. She would have preferred to have on a pair of stiletto... Read full Story
shemale lover 2011-11-09 4,714 anal sex shemale Frottage
66%
A Girl's Best Friend
The party was in full swing when Ryanna and her friends arrived. Of course, they were an hour late, since Glenys had gotten lost on the way. The house was out in the back woods; the owners didn't exactly go out of their way to make it easy to find. Their fellow townspeople probably would have frowne... Read full Story
shemale lover 2012-03-06 5,481 Crossdresser Shemale and Girl oral sex condom sex
100%
Shemale on wheels tour
Being a sexy naughty city girl like myself…I get allot of attention from the boys. I always enjoy getting the attention of the small town boys that are not used to seeing a sexy bitch like me roll though town. They jerk off to girls like me online all the time. But having me right in front of... Read full Story
shemale lover 2012-05-17 3,564 anal sex fingering domination oral sex facefucking
94%
Fem Firm: Character Intro
Coxson & Dicster is a law firm made up of nothing but she males They are: Debra Coxson- 37 Debra has been a lawyer for 12 years and started the firm with her college roommate Angela Dicster 5 years ago. She's a leggy ash blond with 38D tits a great ass and a 9 inch cock. She loves to ... Read full Story
bennyx709 2015-07-29 5,325 Cumshot suck shemale oral
57%
Sucking cock, a curiosity. Part 1
I've been a straight man since forever. I've also been into sex and porn since I was young. And my fetishes always involved tits and big asses. Any kind of tit play turned me on. Still does. When I was 14, I saw a porno and watched tittyfucking for the first time. It turned me on so much, ... Read full Story
bigdickthug 2017-05-22 5,088 Fetish Big Cock Sex Toys
85%
My Erotic Free Shemale Porn Movies Sex Scene In The Air
My job as an airline stewardess always keeps me on the move. The fact that I am a shemale limits me to hanging out with a certain group whenever I go to certain cities. Well, one particular night flight, there was a handsome man that pinched me on my ass as I walked by. Normally, I would complain... Read full Story
shemale lover 2015-12-11 8,807 anal shemale porno
69%
Shemale Video Galleries And A Cock To Bang
I arrived in Bangkok one early afternoon and I was ready to experience the thing the place was famous for. As soon as I checked in my hotel and got in my hotel room, I started searching for some hot encounter through shemale video galleries. They were all really pretty and promised a lot of fun. ... Read full Story
shemale lover 2016-04-20 4,238 first time Big Tits shemale
100%
Bangkok Bar Girl
I recently attended an international trade conference in Bangkok. The manager of our small office there, a big, ruddy-faced 50-something American called Mac, took me under his wing. (I'm 32 by the way, and married.) Before I left for the conference my colleagues in London wound me up mightily about ... Read full Story
shemale lover 2012-02-11 4,510 anal sex Ladyboy Sex Toys
100%
Fulfilling A Girl's Male Fantasy
"Get undressed," the pretty brunette told me, and I obeyed. She was called Jennifer, we'd met the night before at the rock nightclub, and I'd thought that she looked gorgeous in her goth make up so she invited me back to her place. It turned out that she was eighteen and still living at ho... Read full Story
shemale lover 2012-04-04 3,718 orgasm fingering oral sex Sex Toys
92%
T-Girl Meets T-Girl
It was a silent car ride home. He looked at her, she looked out the window. She looked at him, his eyes were on the road. Neither of them broke the silence. It stayed that way until he parked in her mom's driveway. The soft-spoken young man told his girlfriend, "Goodnight Ashley. I'll call y... Read full Story
shemale lover 2012-08-29 6,166 anal sex Cumshot shemale and shemale domination blondie
100%
Big Dick Alessia Visits Dallas
Alessia Hung Mature MILF travels to visit a Big Dicked Man and his Sexy Household If you like Transexuals, big cocks, bondage, BBWs, big clits, deep throat, fisting, 69, ass fucking, sounding, piercing, cum swallowing and big loads this story is for you. If not don't bother reading. If you fav... Read full Story
darrell 2022-04-20 4,336 Group Sex Cumshot Shemale Fucks Guy Blowjob blonde Big Cock Asian Shemale and Girl Sex Toys Mature Ass to Mouth shemale + shemale
100%
Little cock convention
They came from all over the nation to downtown LA convention center. It was the "Little Cock Convention" I watched as men from all races and status came in. Sometimes they came with their wives,friends,Mistresses,lovers, or even their boyfriends. I was on Guard duty and walking the conven... Read full Story
shemale lover 2014-07-07 7,001 shemales hardcore sex humor
100%
Shemale On Webcam Made Me Cum
It wasn't enough for me - regular porn, regular girls... I felt like I was losing it, not having the only thing I really desired: a shemale. But I was new in that world, not knowing where to go, where to look, so I decided it was better to see shemale on webcam first. I searched the internet and ... Read full Story
shemale lover 2015-12-31 3,952 Big Tits Cumshot shemale
0%
Just a Sex Story
I just love to write stories about various types of sex. I love to write and masturbate as I write! The fact is, in fiction I have fucked everybody around and many who are not around. In truth I have even fucked you! And I am going to do it again. First unbutton my shirt and jeans then slip them off... Read full Story
shemale lover 2012-01-15 2,780 anal Big Tits shemale
71%
Choosing From Shemale Pics Gallery
"You into shemales?", asked the man in Amsterdam's Red Light district, "We have everything in De Wallen, just ask", he continued to promote his girls, "Maybe the gentleman would like to watch some shemale pics gallery before making a decision?" And I thought - why not. ... Read full Story
shemale lover 2016-06-30 10,603 anal sex Cumshot oral
100%
How I Used To Cum On Shemale Webcam
I like being a shemale and doing webcam shows. A lot of guys out there would never admit it, but they really like my sort - best of both worlds, so to say: tits, asses and cocks in one convenient package. And shemale webcam was also a lot of fun - I could play with myself as much as I liked and dude... Read full Story
shemale lover 2011-08-10 2,891 anal shemale cum
100%
Shemale Cam Made Me Explode
I really thought it would be just another quick cam session. I logged on to my computer, chose a girl and started talking. But after a while, she told me she's a shemale - then I realized I'm in the shemale cam section. I replied that it's ok - hell, I'm all about trying new things and broadening ho... Read full Story
shemale lover 2011-08-11 3,010 Big Tits cum fingering
75%
A Big thank you to everyone and what's to come next year!
Hi everyone! This is something of a yearly wrap up that I wanted to write up. First I wanted to thank you all for following me this year ❤️ This was the first year that I decided to start taking this seriously and create content full time. I think I still have a ways to go to improve my content, but... Read full Story
Kate Quinn 2022-12-31 3,290 Amateur Big Tits Big Cock Shemale and Girl Guy Fucks Shemale
68%
Shemale Porn Photo On The Wall Of Her Room
She was a truly hot shemale that I’ve been seeing for a couple of months now, from time to time. She had some really big tits and a dick that didn’t really get in our way much. It really wasn’t all about the sex. I loved talking and even cuddling with that girl. We talked about ... Read full Story
shemale lover 2016-06-12 6,506 asshole shemale Big Cock
62%
Bobbys Preggo Shemale Turn
This is a story about how a 14 year old normal guy became a sexy 16 year old pregnant Shemale. It has many similarities to real events. Bobby was a normal guy. he grew up in a good family and was fairly popular. One day when he was in 9th grade his class recieved a new teacher. Her name was... Read full Story
shemale lover 2011-08-18 4,661 Big Tits shemale submissive
100%
Blossoming Shemale
My name was James. It was, before everything that happened, anyway. I'd come from pretty good stock, as the snooty, upper class would likely say. I guess I still did, although it would take a DNA test to prove it now, and to be honest, I didn't really have the desire. That was all before. I have to ... Read full Story
shemale lover 2012-08-01 5,009 Cumshot shemale Big Cock oral sex
100%
Male or Shemale, Still a Slut
Part 1 My name is Brandon. I'm 18 (still in high school), 5'5", white with black hair, and rather feminine. I'm really slim with barely any body hair. All this has combined so that I'm not so popular with the ladies, which sucks cause I am one horny son of a bitch. Luckily, I'm rather fond ... Read full Story
shemale lover 2012-12-20 9,296 Cumshot sucking blonde ass fucking Guy Fucks Shemale
57%
Amsterdam shemales
This was a few years ago I decided to go to Amsterdam and see if I was gay . Booked A weekend and went drinking,went around the the red light district see what girls and others were around. Went to this beautiful brunnett girl from Bulgaria with big tits, she started sucking me off but I could not ... Read full Story
Saoirse1973 2017-06-28 16,789 Shemale Fucks Guy Blowjob Ebony Interracial
27%
I have been out dune by my little brother by a big difference hi
I am 32 years old and my lady who was 46 and my little brother who was just 14 years old then wanted to have some fun and get my woman who was just the right for him he was just out of his mind about her and I was like I'm all about it and I was thinking that I was going to be the big cock an h... Read full Story
Not long but hard 2017-10-19 5,906 Big Tits gangbang Shemale and Girl Solo Shemale Cartoon shemale + shemale Wow.
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 18,906 tranny Big Cock jerking off
89%
Father-In-Law Shemale Adventure
My wife's parents were visiting LA from back east. We live in a small one-bedroom apartment in the valley. She wanted them to stay with us but we didn't have room. They got a room in West Hollywood. My wife and her mom had gone shopping for the day. I was supposed to be at work but at the last momen... Read full Story
shemale lover 2012-07-04 7,389 shemale oral facial facefucking
100%
T-Girl Rodeo
Howdy folks, we would like to welcome y'all to the finals for the 10th Annual T-girl Rodeo! Now this here being the tenth anniversary and all we're gonna put on one hellva show for ya! Commentating up here in the announcers box with me is the first ever T-girl Grand Champion, Lorna "Tail Buster... Read full Story
shemale lover 2012-09-05 5,168 Masturbation shemale and shemale Big Cock condom sex ass fuck
93%
SHEMALE SEX IS THE BEST
I had been in sex with gays for 1 year, but had always been intrigued by those hot looking chicks who packed more than a pussy between their legs. I had no idea where to find one in Kanpur I was definitely bi-sexual, still seeing whores, and still going to gloryholes for my cocksucking needs. I w... Read full Story
shemale lover 2014-03-07 4,716 tranny Big Cock ass licking doggy style big boobs rimming
93%
My First Girly Cock
It was cold. I was running fast so that I could not get too wet by the falling rain. The streets were quiet, because everyone was inside. It was twenty minutes before midnight. I was nervous. It would be my first time I'd have sex with anyone other than a woman. I love women. I'm in love with them. ... Read full Story
shemale lover 2015-02-27 5,647 tranny Cumshot Shemale Fucks Guy ass fucking Guy Fucks Shemale
83%
Milking Time Jordan's Arrival
These stories involves a group of shemales who live on an island that exists in our world, but they chose to remain mostly isolated. That's part of the reason I also call them amazons. The shemales in my stories have genitalia that start at John Holmes' size, and then get much bigger. (This is a... Read full Story
gman57 2019-09-25 10,599 Big Tits Big Cock shemale + shemale
88%
Girl from Uncle
Tonight, I have to tell it all. It’s no secret that my uncle and I had a very special bond he had been eyeing me with those adventurous eyes from the time that I was 14 years old. And frankly I enjoy his ogling. I could feel my nipples get so hard when he looked through me with those alert and spark... Read full Story
Regina10 2024-02-14 5,187 anal Crossdresser Big Tits Bareback Blowjob Big Cock Ebony Lingerie Guy Fucks Shemale big ass femboy Ass to Mouth cum in mouth
100%
My lesbian shemale adventure
My name's Kimmi and I used to be a stripper. I'm a genetic girl, and I always had a wild streak. Guys liked me 'cause of my long blond hair, slender build, and sense of humor. They also liked my 36C breasts :) I danced at a place on Sunset Blvd in Hollywood (this is a true story, so I won't use the ... Read full Story
shemale lover 2014-08-25 9,436 sucking shemale teasing
93%
My lesbian shemale adventure
My name's Kimmi and I used to be a stripper. I'm a genetic girl, and I always had a wild streak. Guys liked me 'cause of my long blond hair, slender build, and sense of humor. They also liked my 36C breasts :) I danced at a place on Sunset Blvd in Hollywood (this is a true story, so I won't use t... Read full Story
shemale lover 2015-01-19 6,275 blonde Big Cock Shemale and Girl
82%
My shemale weekend
I arrived at Chandra's apartment about 2pm. She greeted me at the door wearing a pair of short gym shorts and a tube top. She kissed me and let me in. My cock grew hard immediately and all I did was walked into the apartment. Chandra led me into the livingroom whenre her roommate Jizelle was sitting... Read full Story
shemale lover 2015-09-05 9,468 shemales Group Sex interracial sex
80%
Buffy the Shemale Vampire Slayer Part 14
"Let's get this over with," Buffy suggested. "The sooner we start, the sooner I kick your demon ass." Baphomet smiled. "You will fuck the witch," he said, "while I fuck you." Buffy shook her head. "Willow's my best friend. I can't-" "Th... Read full Story
shemale lover 2011-08-23 5,067 anal sex asshole Big Cock
93%
My lesbian shemale adventure
My name's Kimmi and I used to be a stripper. I'm a genetic girl, and I always had a wild streak. Guys liked me 'cause of my long blond hair, slender build, and sense of humor. They also liked my 36C breasts. I danced at a place on Sunset Blvd in Hollywood (this is a true story, so I won't use the... Read full Story
shemale lover 2013-07-20 3,843 Cumshot Shemale and Girl big boobs handjob kissing
83%
MY FIRST TIME WITH A SHEMALE - 2
DEAR READERS I DON’T KNOW IF YOU LIKED MY FIRST STORY AS THERE WERE NO COMMENTS ........ !!! After we finished our late dinner in the very cosy position she whispered “wanna have some wine honey?” I replied “I’d love to”. She got up leaving me sitting on her bed and poured two large glass-full of... Read full Story
Lisawantsu7 2014-09-02 6,588 hardcore Creampie Big Cock ass fucking Shemale and Girl
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 10,044 anal shemale oral sex
100%
How I sucked my first shemale cock
It was the beginning of the year 2023, in January, three days after New Year's Eve. I was driving home in the morning from a party 100 miles away from my hometown. On the highway, after going half the distance, I received a notification from my dating app, and I was like, "Oh, a new match", I'll che... Read full Story
cock&heels69 2023-05-25 8,668 Stockings cock Masturbation sucking Blowjob shemale orgasm oral sex porn high heels cum shot first experience
50%
AMANDINE ⚧️ ⚧️
Le lycée n'était pas un endroit amusant pour moi. Étant plus un outsider geek, plus intéressé par la science, les ordinateurs et la culture pop associée à ces intérêts, cela signifiait que j'avais peu d'amis. Cela signifiait aussi que j'étais si loin de l'échelle sociale que je n... Read full Story
Femboy 2021 2023-03-20 1,028 Stockings Crossdresser Shemale Fucks Guy Shemale and Girl domination Sex Toys
50%
Maman se met en colère contre son fils Pussyboy
Histoire d'un fils de pussyboy qui est transformé en putain de bite par sa mère. À 31 ans, je ne devrais pas envisager de retourner vivre avec ma mère, mais j'ai récemment divorcé, mon ex-femme m'a viré et j'ai dû me mettre à genoux pliés vers ma mère pour un toit sur ma tête. C'est avec un sentim... Read full Story
Femboy 2021 2023-01-24 968 Stockings Crossdresser Fetish Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys