Shemale Suprise Stories

1,639 results
Orientation
Length
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Infinite Scroll

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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Brazillian Punsihment

by Ravenarioch on Feb 7, 2018
Transsexuals & Crossdressers

Frank Shepard a private detective who is trying to find his luck in Rio de Janeiro awakes in his bed during the day of Carnival, the sun's rays hitting his eyelids he turns himself over in bed and looks at the sky on this lovely day. His sky blue eyes thinking about what a horrible day to be a private investigator, his case was to find the little brother of...

Your Sister's Tough Times

by One37 on Jun 29, 2016
Amateur

Sarah is Sam's older 21 year old sister. She is 5"4 with long brown hair, skinny with a big ass and 32C cup tits. She lives in her own flat with her boyfriend, while Sam live at home with your parents. Most of your friends always make comments to you about her looks to wind you up. However, he tries to ingore them and get on with things. Speaking of fri...

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Blossoming Shemale Ch. 02

by TheTitLover on Sep 25, 2017
Transsexuals & Crossdressers

This is inspired by:http://www.literotica.com/s/reluctant-shemale tawnysuede's Reluctant Shemale if you enjoyed it, I hope you'll enjoy this series. * * * 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...

When Sara Met Bob Ch. 05

by yellowfrog on Sep 14, 2017
Fetish

Bob remains the love of my life, the fountain of my admiration! Handsome beyond words, virile and composed, sexually insatiable in many ways, Bob has become what every woman wants - in addition to her own husband, of course. In the intimacy of our extra-marital affairs I enjoy massaging his prostate, deeply and slowly, my fingers moving very deliberately to...

Seeing Maisie in Japan

by boltox95 on Feb 6, 2021
Amateur

You can't believe that you see Maisie fucking Williams stand outside the spa you just tired to enter. She is with 2 of her friends which is quiet cute, but you have always had a thing for Maisie. Her petite frame, unconventional face, her bad ass role ass Arya in GOT and her otherwise down to earth approach in real life or at least what we see of her in real...

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A Dream Come True Ch. 01

by severomi on Sep 18, 2017
Transsexuals & Crossdressers

This is a two part story. Part I is reality and true while part II is my Dom's dream. PART I - The truth I'm an American abroad, been in Europe most of my life, now 58 years old and have been married twice with little success. I decided to change what I'm looking for, after having reflected on my previous relationships, where I had also two TG/TS relatio...

Create your own growth story

by Mhossa on Jul 2, 2019
Fantasy

*Welcome to my first interactive story on here* Before we get started, here are a few simple guidelines. Please, try to make an effort to check grammar and punctuation, as I’d like this story to be readable. Next, put some effort in to the writing, it makes the story a little more interesting to read if it looks like you tried :) lastly, but most importantly...

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Futanari World

by styxmaster on Apr 16, 2016
Fetish

You wake up this morning to the sight of your younger sister Sarah pulling your covers off of you. "Get up Doug, you don't want to be late for school." You get dressed for school after Sarah leaves your room. you never mind school that much, you mostly get B's and A's in your classes but given the opportunity you would like to just stay home and wa...

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Pounded Into Submission Ch. 02

by Jamesjones52 on Sep 12, 2017
Transsexuals & Crossdressers

*This is the prologue that leads up to Joe being "Pounded into Submission". Also, I read the comments about this being a repost. It is; I am the lonejackman. I got rid of my yahoo email account and couldn't get my password reset for here. * Two days ago Joseph was checking out porn like he usually did at his favorite site xhamster. A couple of BBW vids here...