Shemale Girlfriend 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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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...

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...

Birth of a New Sissy Ch. 01

by AltErik on Sep 18, 2017
Transsexuals & Crossdressers

Usual disclaimers, though if you are already browsing stories on this site, you must have an idea what you're getting into by now. ;-) This story contains male to male sex, Crossdressing and Dominant/Submissive themes, so if this is a problem . . . wave off! This story is fictional story based on a fantasy of mine. While it is fiction, I did use myself an...

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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Black Cop in Canada: It's My Life

by Samuelx on Sep 17, 2017
Non-Erotic

Standing in front of his locker, Ottawa Police Service constable Stephen Jean Guillot read the words "No Negro Faggots On The Ottawa Police Force" and sighed. Squaring his massive shoulders, the young Black man turned to look at the other police officers in the locker room, white men one and all. Glaring at them, he spoke loud and clear as he demanded to kno...

A Sissy Surprise "The House Warming"

by Simply_Sissy on Feb 6, 2018
Transsexuals & Crossdressers

My girlfriend Vicki had been really pushing me to go to her friend Mary's house warming party on Saturday night. Mary had been quite the bitch lately not like the two of us ever really hit it off. To make things even worse she is aware of my panty wearing secret. Vicki had shared this bit of information with her when she first discovered my little fetish abo...

Bethany's Secret Ch. 2

by Wannabe Chick on Sep 18, 2017
Transsexuals & Crossdressers

-3- Before beginning my story about what happened to me the week before Christmas, I should explain what had happened during the past few months. Early in my senior year of high school, I had met a gorgeous girl named Bethany who became my girlfriend. On the day of our four month anniversary, we had sex for the first time. What I didn’t expect, however, wa...

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...

My First Shemale encounter.

by luv2getnaked on Apr 20, 2020
Transgender & Crossdressers

Only recently I had developed a strong desire to be with a hot looking shemale. I really did not know how to make contact with anyone in the small city I lived in, and figured it would likely never happen to me. One day at work at my computer support job, I was informed that another branch of our firm in Las Vegas had experienced a server failure, and I was...