Bully Roommate Sissy Stories

23,222 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 SmutMD.com

Caught by My Bully and Exgf Ch. 01

by CindyTightass on Sep 15, 2017
Transsexuals & Crossdressers

Dear readers, this my first erotic story, all of protagonists here are fictional consenting adults, I hope you enjoy reading it! ***** I was 21 year old student with part-time job, living in a small flat in big city when this all happened. I broke up with my girlfriend Michelle, after seven month long relationship with her, because I received a video from...

Sissy en español

by SissyJ on Apr 14, 2021
Transsexual

Hola, hace tiempo que descubrí esta página y no encontré muchos relatos de este tema en español así que escribiré una de mis fantasías aquí, sientanse libre de agregar capitulos ya sea desde cero o ya de alguna historia que tenga comenzada, lo puse público. Esta es mi primer historia que escribo asi que no esperen una obra literaria o algo parecido pero espe...

Open in Reader

Who's The Sissy Now?

by britneyfan on Sep 13, 2017
Transsexuals & Crossdressers

Like many people, I was bullied in school. I was small, slender and effeminate and, as a result, was often called gay, queer, fag and sissy by school bullies. The fact that what they said was sort of true just made it closer to the bone and more painful to hear. Like many teenage boys, I was going through something of an identity crisis surrounding my body a...

Playing the Part

by Sissysdream on Jan 20, 2020
Transgender & Crossdressers

All people in this story are above 18 or older. This is just a fast story I wrote and don't know if I will do any more on this story. *** My name is Tommy, but these days I go by Tammy. A few weeks ago, I was turned out by my high school bully during summer break and now I am a happy cum drinking sissy. I know I'm getting a bit ahead of myself here so let...

Tatum's Friend, the Bully

by justincbenedict on Jul 31, 2019
BDSM

Pearson checked the lip gloss in the mirror. He looked perfect. Pearson knew he really didn't look like a woman, just a pudgy little man, chubbiness poking out of the hideous pink nightgown that he and Tatum had purchased through the tranny site. But he liked this-he would go into the bedroom, and Tatum, gorgeous in her own lingerie, would make him suck her...

Caught by My Bully and Exgf Ch. 02

by CindyTightass on Sep 15, 2017
Transsexuals & Crossdressers

This is second chapter of story about young crossdresser who is discovered by his ex girlfriend and masculine bully from high school. All protagonists of this story are consenting adults. ***** "Your face is a one big mess Cindy," said Michelle giggling, "let's go to the bathroom and clean you up!" She helped me to get up from my shaky knees and led me to...

Jack's Bully Ch. 04

by Alpacawreck on Sep 5, 2018
Fetish

Jack woke up in the morning and was greeted to a beautiful sight. He watched Emily sleeping and was glad the day before wasn't just a dream. He reflected on how things had developed so fast and it was all thanks to Matt and his cock. As he thought of Matt's huge cock he noticed his clit had started to harden. He looked back over at Emily wondering if she wou...

I Get Bullied, My Mom Gets Fucked

by I_Love_MILF on Jan 8, 2019
Mature

My mom, Christina, had been at war with one of her students, Zack, the starting quarterback on the university's football team. The meathead, who was left behind a year, had no trouble getting girls his age...hell, I think half the campus wanted him. Guys were forced to be his friend because if you weren't his friend, he was your bully. Christina was the law...

A New Life: Prelude

by cuckcrossdresser on Sep 16, 2017
Transsexuals & Crossdressers

Note: This is my first time publishing here. I've been meaning to write this story out for a while now, but only recently got the courage to do so. This is the first part of a series and everything in this series is true, I have just changed the names to hide my identity. ***** My name is Joshua and even as a child, I remember wishing I had been born a gir...

Bullied

by Testytesterton on Sep 12, 2020
BDSM

You are an 18 year old boy surrounded by bullies everywhere you turn. Your high school has apparently elected you the mascot of the losers and wimps and selected you to receive the lion's share of attention from the bully boys while simultaneously being ignored at best by the girls you lust after. At home, your family is cruel and controlling or coddling and...

Open in Reader