Bully Roommate Sissy Stories

23,222 results
Orientation
Length
Source
Infinite Scroll

The Hardest Kind To Be Ch. 01

by Joe Wordsworth on Sep 16, 2017
First Time

In the offhand chance that you don't find the setting clear on the issue, all characters are eighteen and legal. This is also a madly different story genre than I'm used to writing, so be kind. . . .. ... ..... She hated her. Hated... though strong and dramatic, it was the only word that summed up their relationship. Nobody would have guessed it, but i...

Being My Roommate's Sissy Pt. 03

by SubTessa on Feb 6, 2018
Transsexuals & Crossdressers

SubTessa (Author): Sorry for the wait guys, University sort of made me forget about this entire thing. If you're new to this series and start here, I think it'll be ok. The last two are just the lead up to this day. I hope you enjoy it! You should also read these with a healthy level of self-esteem! ~~~~~~~~~~~~~~~~~~ I wake up, quickly forgetting what I...

Brad's Return Ch. 01

by grizzley123 on Sep 29, 2020
Loving Wives

Brad's Return, Chapter 1 ****************************************************** This is a continuation of the "Brad's Suggestion" stories I wrote a while back. It has similar cuckold and bisexuality themes, along with some lesbian and light BDSM fun thrown in. It emerged from my never-ending desire to put off the real work I should be doing. I hope you enj...

On the Hunt Ch. 03

by Lisa2506 on Jul 31, 2019
Exhibitionist & Voyeur

Hi, Madam Lisa again. This is day three of the ongoing story of my real life sub and myself. I have changed only the names of those involved. I do not mention any locations by name, but I will assume some of you will be able to figure them out. Please read P1 and 2 as doing so will help you follow along. *** Recap. Yesterday I found my subs ex-girlfriend,...

Mom's Big Black Hobby Ch. 06

by MiddleKoala on Jul 13, 2020
Transgender & Crossdressers

This story has with incestuous and homoerotic themes as well as non-consensual sex. If you are offended by such, do not read. This level of depravity is not to be taken lightly and the deeper down the rabbit hole you go the more you will find that may offend you. You have been warned! All characters in this story are over the age of 18. The entire story is...

Becky's Video

by purekink on Sep 13, 2017
Transsexuals & Crossdressers

I suppose I was the one that first mentioned porn to Nikki. We'd been chatting on a girls' night out and laughed abut how I'd never found any porn in the house. She giggled and said I was bound to find some sooner or later -- all men had some, somewhere. A few days later, I'd completely forgotten our drunken conversation and so when Nikki showed up at mine...

A Sissy Saga Ch. 17

by Snurge on Sep 15, 2017
Novels and Novellas

Titled people were a weakness with Miriam Hancock. She frequently spoke of them with harsh condescension, but the snob in her heart secretly rated them higher than wealthy businessmen, and so it was with some delight she agreed to the visit of the ennobled Marchioness of Wiggleswick. The delight had doubled when she discovered that in both Debrett's Distingu...

Being My Roommate's Sissy Pt. 01

by SubTessa on Sep 19, 2017
Transsexuals & Crossdressers

We approach the door to my dorm, walking slowly with our hands in our pockets. Glancing over at her she seems sort of detached from the conversation, maybe thinking of what she's going to say when we reach my door? I feel kind of nervous as we step our way through the dim-lit corridor, it must be at least 11 at night now; all the dorms are so quiet - making...

Keith's Caught in a Costume Pt. 03

by gaildaniels84 on Dec 24, 2019
Transgender & Crossdressers

Keith's alarm went off and he silently reached out a hand and silenced it. He'd hardly been able to sleep at all, tossing and turning with worries about what school would be like today. It had been less than a day since his life had turned into a nightmare - his incredible teacher had caught him rubbing himself in a cheer uniform and then he'd had to buy pan...

Beta Male Slave Academy Ch. 02

by Tazokm on Jul 13, 2020
BDSM

After being blown and locked, Miss Carly explained to me that the compound we were at had over a hundred rooms and approximately 50 current residents. She began walking me to a room where I was to keep myself preoccupied until they had prepared my sleeping arrangement. I walked butt naked behind Miss Carly down a high-ceilinged hallway. Her ass was absolutel...