Free Shemale Stories

First time with a trans escort

I've thought about seeing a t-girl escort many times and a few weeks ago I finally made a date with a local girl named Carol. She´s a lovely Colombian girl with long dark hair and a slim, sexy body. She welcomed me into her home wearing a sexy black dress and high heels and after pouring a d... read more

Gracemel121 March 28, 2017 82%

Karen, My School Teacher Part 4

Meeting my other teacher By FoxyHosed Next morning as I woke up, I jumped in my clothes and got myself a coffee, and went to school. I got in 15 minutes early because I didn't want to run into Karen. As I entered the door to the school, I saw some of my classmates. I thought the coast was clea... read more

FoxyHosed February 17, 2021 100%

Loosing my virginity to Shemale Preet

This story is of may be 2017. When a shemale escort took my virginity n fucked me. I am not new to shemales. I hv been attracted to shemales since 1999 when first time I got internet at home. Suddenly while browsing i saw shemale website n instantly i was hooked to it. Well how I met my first ... read more

Stud4Shemale February 20, 2021 100%

Bareback fuck by Lysa Shemale

Well I am devoted shemale lover and have met many shemales in my life. This incident is of probably December. I called my shemale escort Amy to meet and some how she was not picking call. Then around 4.30 pm she picked n told me that she is having hangover due to party so was sleeping, so I sh... read more

Stud4Shemale February 20, 2021 100%

My First Encounter With A Shemale Escort Part 1

I was feeling extra horny as I walked up the stairs to the apartment. Knocking on the door I heard a voice from within say "come in". The door was unlocked, so I walked into the hallway which led to the lounge. Seeing no-one around I called out "hello", to which a reply came &quo... read more

shemale lover August 16, 2011 80%

I and the old man's story 后面中文

I am from Chongqing, a boy who loves his father. When I was young, my neighbor aunt always said I looked like my sister, like a beautiful girl. At that time, my family was relatively poor. My Sister, my parents, and my family of four lived in public rental housing of less than 30 square meters. Star... read more

Oldslut Sissy April 15, 2024 50%

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 more

Jon Paul May 26, 2023 100%

Fun time with russian shemales in Moscow

The first day, I was with my Russian friend, who introduced to me the Russian shemale escort. Since I know he is a big fan of shemales, so I wasn't shy of asking him about shemale escorts in Russia. He called in a shemale escort for me rightaway. I was staying in a hotel in downtown Moscow. Since my... read more

shemale lover March 9, 2015 75%

A Not-So-Small Piece of Heaven

I'd never really been one for going out to bars to pick up women, but tonight was a bit different. It was my buddy's birthday, and he decided to invite me and a couple of other friends out to go bar hopping with him. Living in Miami, there was always something going on after the sun went down, so th... read more

shemale lover April 28, 2012 100%

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 more

shemale lover August 23, 2011 80%

Man Is Humiliated By Escort

I am a very adventurous, open minded married guy. I am 6'2", 150lbs and I have a 5" cock. My wife (Mary) is great but she is very straight laced and doesn't like to have sex but twice a year so I decided to look elsewhere to fulfill a few fantasies. I am sure my size and stamina have a lot... read more

shemale lover September 30, 2011 62%

MY Party Favor Fantasy

My Party Favor Fantasy A fictional story built around an old fantasy of mine I ran a notice on one of those sex sites that said” Help me fulfill my fantasy and I bet we take care of some of yours also. Hi there, I am Penny and I am a total bottom trans w... read more

pennypenny January 8, 2019 92%

Buffy the Shemale Vampire Slayer Part 13

Buffy's cock slipped out of Baubo's mouth, and she licked the smooth skin of the stiff, elongated shaft with her tongue. Baubo had no hands, but, even so, she was a superb cock sucker. More than once, she brought the Slayer to the brink of orgasm, then backed off, letting Buffy's sexual passion abat... read more

shemale lover August 23, 2011 80%

Getting Fucked by Sasquatch

Bill was about to show up, I had known him from a chat room for years now. I was in his town for work and we had set up this date so we could finally meet each other. I heard a hard knock at the door and when I swung it open, I just stood there in awe. It wasn’t the big beard or really long hair tha... read more

pennypenny August 21, 2020 80%

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 more

pennypenny February 25, 2019 100%

Regina’s Double threat.

Hello guys, I recently ran into a former hater who was no longer the hater I had met years earlier. In fact, he had only treated me so horribly because of his own inner dark desires. When we met a few years ago at one of the clubs, he had been very abusive to me. He went out of his way to say hurtfu... read more

Regina10 February 8, 2022 100%

Fender Bender Chapter 8

My name is Robert, but when I am dressed I call myself Vicki. I am 5'9" 160 pounds, blonde hair and blue eyes. I turned 18 a few months ago. The last two weeks of summer vacation was a wild time for me, I knew that things would settle down once school started. Gary, my best friend for years,... read more

shemale lover July 27, 2012 100%

Down the Path Part 5

I force myself to walk down the corridor and to the elevators. When the door opens there is an older couple in the elevator and I get on and move to the other back corner. The man's wife is standing a little in front of him and I see him look over at me briefly. Then he looks again, giving me the on... read more

shemale lover September 17, 2012 100%

Satan Shemale Bimbo Sissy Doll Chapter 1

At just 22 years of age Johnny was bored and disgusted with his life. He would spend his nights in satin and leather with his face made up in a long blonde wig. He would become Sindra, a creature of the night. Sindra would pull on her long black kid gloves and masturbate to photos and fetish cart... read more

shemale lover August 28, 2011 50%

Beefy Buns

It's hard to get good help. Probably, that's true in any business, but it's especially difficult to find decent employees in the fast food racket. Believe me; I've tried. I manage the local Beefy Buns franchise--burgers, fries, and shakes is our mainstay, but the menu also features fish and chick... read more

shemale lover April 22, 2012 100%