Bully Roommate Sissy Stories

23,222 results
Orientation
Length
Source
Infinite Scroll

Grand Opera

by misterJJP on Jul 9, 2018
BDSM

My name is George, and I am an opera lover. Verdi, Puccini, Wagner,... are my musical heroes and I listened to their masterworks more than anything else in my typical Floridian suburban home with swimming pool, BBQ, lanai, etc. I spend most of my time outdoor and sometimes I must be a nuisance to my neighbors with more traditional music tastes, but who can...

Sissy for Mommy's Nipple Cream Ch. 02

by ppeaks42 on Feb 7, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Recap ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ While raising her son Jim as a single mother, Julia developed a special bond with him by never stopping breastfeeding, which had the side effect of growing her breasts to a monstrous H-cup. Once Jim hit puberty, Julia made him start d...

A Sailor's Surprise Ch. 02

by DianeTG on Sep 11, 2018
Transsexuals & Crossdressers

CHAPTER TWO - A Sailor's Journey - becoming the farmer's wife It's been a while since I wrote Chapter One so a quick review might be in order. A young sailor who joined the Navy to escape his fear of becoming a "sissy" because he loved wearing his sister's clothes, gets sent for a special language course at a remote army base. Given an unexpected 7 day leav...

Sutters Hollow Ch. 02

by BlackMadonna on Nov 19, 2018
Sci-Fi & Fantasy

SugarPucker Creek If there was one name in all of Sutter's Hollow that was almost always linked with troublemaking and mischief, it was Bobbi-Jo Butters; just plain BJ to those who knew her well. Bobbi-Jo was a down home southern tom boy with short muss-cut dark brown hair, freckles in all the naughtiest of places, and big beautiful baby-blue doe-eyes that...

Gotta Stop Misbehavin', or Not

by SolidHeartNotCock on Jun 6, 2018
Anal

I've been with Dora over 10 years now, we know each other well. She's solidly built, not fat but not thin either, short, slightly curled inwards black hair, medium large breasts, wide sturdy hips and fairly large bottom, a super-strong sex drive, and a confidence in herself one seldom finds in a man, let alone a woman. I'm thin, not particularly strong but h...

Papa Knows Best

by justincbenedict on Jun 26, 2018
BDSM

Everyone in this story is over 18. ***** Walking up the path to the house, Tippi knew she looked good in her new riding boots. Would Papa understand? Would he respect her finally as a career woman? Tippi had her own staff and was quite the corporate maven in New York. However, Tippi's family had always ridiculed her, the quick temper and childish pompo...

The Matriarch Ch. 01

by AMurphyWriting on Jan 8, 2019
BDSM

*This chapter deals with much of the administration that new pets at The Matriarch must undergo. As a result, it doesn't contain as much of the good stuff as the introduction did. Rather, it lays more solid groundwork for future chapters.* ***** *When last we left off, our young protagonist had just been hired on as a pet by the notorious Violet, owner of...

University Life - First Ch. 01

by ParanormalQueen on Sep 14, 2017
Novels and Novellas

'Mum, Mum...MOTHER!' Kainene screamed the last word. 'Gah! What is it, Child?' Her mother snapped in irritation. She was trying to stuff her daughter's novels into her suitcase and it refused to shut. Her face was red, she was sweaty and her daughter was screeching in her ear. She was not best pleased. 'Don't yell at me mum, I'm trying to tell you not to...

The Love of Panties Ch. 05

by chuckp7860 on Sep 14, 2017
Fetish

I continued to go over to my friend's house. They worked so much and I had the opportunity to go over there during the day that I never really had much fear of anyone showing up. She never was much of a sexy dresser on the outside but after a few visits and several times of going through her drawers I soon learned that underneath her skirts and pants was a...

Pet's Disgrace Pt. 01

by MsCM on Sep 15, 2017
BDSM

It's been ten days and Jordan was dying to come. The arousal was persistent, crawling all over his body, concentrated in his cock which seemed semi-erect most of the time and which became achingly, almost painfully hard with the slightest stimulation. He hadn't been able to focus properly for the last few days, his thoughts veering off towards sexual images...