Sissy Roommate Stories

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Connie Goes to College Ch. 06

by cmorehead on Sep 25, 2017
Transsexuals & Crossdressers

Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. * My freshman year in college became quite a year for me in terms of defining my f...

Lulu's Lockdown Diary

by lululuvsblack on Jul 6, 2020
Transgender & Crossdressers

Day 1 So, with this virus we've all been told to stay home and not have any physical contact with people outside, not get together in groups at all, and not even step out of the house if not completely essential. We're locked down. I guess it wasn't a great time to move in with a couple of guys I barely know, but there you go. There's nothing I can do about...

The Bimbug

by Testytesterton on Jun 17, 2020
Science Fiction

The world changed overnight with the first cases of the Sexually Infected Subjects Spreading Infections Exponentially Syndrome, or SISSIES, became known. At first it sounded like some urban legend, men turning into hot, horny, hung shemales and spreading the infection to any man that came in them...or any man they came in. It was only after you saw video evi...

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Connie Goes to College Ch. 03

by cmorehead on Sep 16, 2017
Transsexuals & Crossdressers

Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. In my last chapter, Jeff and I had just made love for the very first time and I w...

My Girlfriend's Sissy Roommate Ch. 02

by SEVERUSMAX on Sep 16, 2017
Loving Wives

"So, buddy, what gives? Or should I say, girlfriend, because, let's face it, we've always acted more like girlfriends in the platonic sense, well, minus your tongue going between my thighs. Other than that, you've been more like a female friend or a gay male one or something like that. Anyway, let's talk, openly now, about what Rain wants out of this relatio...

New Gurl in Town Pt. 01

by GavinIsaNuisance on Jul 6, 2020
Transgender & Crossdressers

This work is entirely fictitious. Any similarities to actual persons living or dead is purely coincidental and entirely unintentional. All characters portrayed in a naked/sexual nature are 18 and up. *** The city of Los Angeles, California. A place once regarded as the focal point for entertainment and movie stardom now reduced to an over-taxed, grimy, dru...

Caught in Panties & Dominated Ch. 05

by Tracy69 on Dec 3, 2019
Transgender & Crossdressers

Cast Trace - me Tracy - me, dressed en Femme Rick - head of security at work, had just caught me masturbating at work, dressed as a woman Ken - my roommate Ok, ok, I hadn't mentioned this before, but my roommate Ken is gay. He would flirt with me from time to time, even hit on me, and I pretended to discourage him, but sometimes, late at night in my roo...

Panty Posers

by EROTICbearscribe on Jun 1, 2020
Transgender & Crossdressers

PRIVATE PANTY SESSIONS Ch. 01 "Wait! What? Say that again." Doug, my roommate of two years, closed his eyes and took a deep breath. Tension hung heavy in the air. I allowed him to take all the time he needed to explain even though my mind was racing the way it does when your entire world has been turned upside down. I could see he was struggling. It look...

My Girlfriend's Sissy Roommate Ch. 03

by SEVERUSMAX on Sep 16, 2017
Transsexuals & Crossdressers

I had to admit to myself that Larissa had never looked as sexy and drop-dead gorgeous as she did right then, bent over as I fucked her from behind and she took me deeper inside her twat. I fucked my new girlfriend so hard that she moaned and pushed back at Rain and me. He could feel the force of her hips and ass as she bumped her crack against his tongue. I...

Tales of Feminization

by AnonWriter on Jun 11, 2014
Fetish

In a seemingly normal town, a new social movement is taking place. White boys are encouraged to act, dress, and be feminine. You are a student at this school, and this is story of how you become a dirty sissy slut. Choose a boy to play as and be feminized. (All characters in this story are of legal age) (I'm only working on Mark's story right now, but feel f...

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