Sissy Bully Story Stories

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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...

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...

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...

A Bully in Frillies

by Cdslavejessie on Apr 22, 2025

Hey yall!!!! So I know I already have two stories going but I decided to add a third to the mix!! This is a commissioned story for Giratuno, who has a love for frilly sissies in ultra girly girl wear, sausage curls, and being totally and permanently emasculated! A bully who bonks their head and loses their memory? Hopefully the bully’s girl victim is nice an...

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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...

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...

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...

A Tale of Two Sissies Ch. 01

by SatinSlip on Mar 26, 2019
Transgender & Crossdressers

Author's Note- this story is a work of fiction. All the characters are eighteen or older unless noted otherwise. This story contains scenes of non-consensual sex, incest, interracial sex, gay sex, forced feminization, abuse, and rough sex. I hope you enjoy reading it as much as I enjoyed writing it. - ***** SMACK! My cheek stings from the big black te...

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...