Sissy Tricked Roomate Stories

10,584 results
Orientation
Length
Source
Infinite Scroll

Sissy RoomMate

by OathkeeperPath on Apr 22, 2025

Story on hiatus until the current released rough drafts are fully finished chapters, I'm also going back to only releasing fully finished chapters, I know alot of you liked how much quicker it moved the story along, but it hurt the overall quality as I tended to take along time to come back and finish them if they were already released. You finally did it, Y...

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sissy healslut

by eagersuckslut on Dec 1, 2017
Fantasy

So i just started the new semester and im kinda broke so i had to get a roomate in a kinda shitty part of town. He's an older black man in his late 40's, he's balding on the top of his head, with greys on the sides and the back, making him look even older than he actually is. He's got dark brown eyes and hes overweight with a giant beer belly, but you can te...

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Tinder Pt. 02

by TwistedPanties on Jan 22, 2020
Transgender & Crossdressers

I appreciate you all asking me for more of the story - It would be hotter if you begged ;) Sissies can be so over-eager... (Keep the feedback coming please, Sweeties) Background: Bryan's roommate Caitlin has just discovered his crossdresser girl Tinder profile, while her friend Allison was swiping for a new girlfriend. Bryan is in the kitchen with a baby...

Sorry Sissy You Lose Pt. 03

by LittleDickSissy on Feb 11, 2019
Fetish

"Mmmm that felt great" George said as she released his thick cock from her mouth. "Thank you". She looked up at him and smiled. She could still taste his cum in her mouth. She'd never had cum in her mouth before let alone swallow it! "Kiss it. Kiss my cock" George instructed her. She did as she was told, she puckered up and kissed the head of his cock a...

You and Heather

by FazeBoi on Feb 12, 2021
Fetish

In this story the characters are: -Sophia(YOU) A blond girl around 5,6 and a nice set of c-cup breasts and a firm ass, -Heather(ROOMATE) A brunette girl around 5,2 and is quite chubby, some fat breasts, jiggly ass and a big belly. The new roomate The taxi dropped me off to my new appartment where I am staying, my room was number 89, so I headed to the 4th f...

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Female Dick Growth

by anonpl4yer on Apr 22, 2025

You're at work and, a notification pops up on your phone. "you received a message"What's next? Your girlfriend Your sister () Your Ex Your Tomboy Friend Your Coworker Your Cousin Your friend with benefits...

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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...

Delilah’s Day Off

by JoshNeeson_007 on Sep 5, 2019
Exhibitionist & Voyeur

When Delilah registered for classes at her university she tried to pick a schedule that was spread out. On one particular Thursday, a day where she only had two classes, both classes were cancelled abruptly the night before. In her Speech class the professor said in the mass email he sent that he had an appointment so that all of his classes were cancelled f...

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Adventures of Josh, Julie and Carol

by I_like_Bottomless_CMNF on Apr 22, 2025

The is the pre-quel, this just tells the characters and their backgrounds. Skip to the next chapter for the actual actions. Consider all characters as legal because the scenario might be misleading, I want to tell my story like an anime. "A Boy in as my roommate? I don't know if I can live with a boy. I wished the warden could see that I would be very u...

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He Changed Me

by Sissyhalo1 on Dec 23, 2019
Transgender & Crossdressers

I know a lot of these stories are about some guy that watched porn or read it and got hooked or were some short femmy guy that got tricked into getting boned but that's not me. I'm Sam and yeah it's Samantha most of the time now. But before that it was just Sam and I was in my last year in college and to save money to fix my car I moved into a rental house...