Shemale Stories

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Shemale Fun

by orangemaestro on Sep 26, 2017
Transsexual

You are a good-looking man in your mid-twenties. You are 5'10, 170 lbs., and in good shape, with some muscle definition. You have always considered yourself a man's man, but lately you have developed a curiosity about women with...something more. When you fantasize, you sometimes find yourself imagining a cock between the girl's legs. Pretty soon, that's the...

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Shemale Stories: A MILF Fucked

by silkstockingslover on Sep 25, 2017
Illustrated

Summary: Lonely MILF walks in on teen girl masturbating and.... Note 1: Thanks to Hernandez for doing the photos for this story as well as the plot bunny that led to the final story. Note 2: This is a 2017 April Fool's Day Contest story so please vote. Note 3: Thanks Tex Beethoven, Robert, goamz, With my daughter Simone away at band camp as a counsello...

Shemale Surprise Ch. 02

by luckybaldrik on Sep 16, 2017
Transsexuals & Crossdressers

I woke up to find myself staring at a nice ass hanging over my head. That ass belonged to heather, an extremely attractive shemale who tricked me into letting myself get gangbanged by a group of shemales. She then let me stay in her apartment, as my clothes had been stolen a long time ago. I then realized that I was being sucked off by heather. She had gotte...

Shemale Surprise

by luckybaldrik on Sep 12, 2017
Transsexuals & Crossdressers

It was a Saturday night and I was chatting up this girl at my favorite bar. Her name was Heather and she had short light brown hair. She was cute, big in general, big boobs and a big ass, but she wasn’t pudgy, and in fact she had a very athletic body. She wore a short white miniskirt with a dark tank top and pink fishnet type top over it. We had really hit...

Shemale Shock

by standingstones on Sep 12, 2017
Transsexuals & Crossdressers

My sister Louise was always trying to set me up with women she knew. Somehow she felt as if she were responsible for my love life. Louise's latest scheme was to throw a party and invite me and all her women friends that she could. I arrived at my sister's party and to her credit there were other men there besides myself. Unfortunately most of the women the...

Shemale Shock Continues

by standingstones on Sep 12, 2017
Transsexuals & Crossdressers

I met Cheryl at a party thrown by my sister. I asked Cheryl to come to my place afterwards and she agreed. That was where I discovered Cheryl was a shemale. I did something I had never done before. I sucked on Cheryl's cock and I took her load down my throat. After that I ended up fucking Cheryl's tight ass and giving her my own load of cum. We had now been...

SheMale Sirens

by WhiskeyIsGood on Sep 25, 2017
Transsexuals & Crossdressers

Of the many mythological creatures invented in the mind of man over time. Some are believable, while others are known to be simple stories created to scare people with weak constitutions or to frighten children at bedtime. Werewolves, vampires, demons... all such creatures are what I am referring to. But the one myth that I had never heard of as a child was...

SheMale Sirens Ch. 04

by WhiskeyIsGood on Sep 25, 2017
Transsexuals & Crossdressers

I never thought I would wind up in what many would have thought was just some fantasy world. I would have considered myself one of those people who thought it was just someone's fantasy. I happened to stumble upon Anthemusa by total accident, which I would later learn was really how the majority of the men on the Island came across it. I had been heading t...

SheMale Sirens Ch. 03

by WhiskeyIsGood on Sep 25, 2017
Transsexuals & Crossdressers

Chapters 1 and 2 seem to have done great, so here is number 3. This will probably be the last one. In the future though, I plan on doing a longer series based off of this, but it will focus on one main character and him adjusting to life in Anthemusa. I don't intend to start that right away, as I have a few other ideas in mind before the end of the year, but...

SheMale Sirens Ch. 02

by WhiskeyIsGood on Sep 18, 2017
Transsexuals & Crossdressers

Chapter 1 has received good reviews, so here is part 2. Part 3 is still being written, but it is going to have more back round info on the Siren's, and a few more characters as well. Should be up soon after this one. Whiskey ***** The day I first decided I had to leave my home in New York was the day I turned eighteen years old. I was tired of everything,...