Sissy Bully Stories Stories

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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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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...

College Stud Takes My Girl

by easyballs on Sep 14, 2017
Fetish

Thanks again go to 'Jill' -a friend - for first requesting my assistance, for her supplying the idea, plot and direction. Also thanking her, for her continued support throughout; If reading pornographic stories offends you go and read some other form of written work! ***** Julie and Tom were both high school students, about to move on to college, having g...

XChange Seminar, X-change, X Change Ch. 02

by Grabenork on Feb 6, 2018
Transsexuals & Crossdressers

"Good morning, everyone! I am Dr. Welcott, and I am very happy to welcome you to X-Change Technologies, Inc. You are all here because you attended one of our X-Change Seminars run by Dr. Brewer at the Comstock Institute. He reports that you all participated in the seminar enthusiastically and then signed a list to volunteer to become future demonstrators at...

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...

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...

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...

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...