Sissy Roommate Stories

20,331 results
Orientation
Length
Source
Infinite Scroll

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...

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...

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...

Boredom and Therapy

by oldhippie1949 on Aug 31, 2017
Group Sex

The following is a true story. Naturally, all the names have been changed but all the events described took place just as I have written. If a bi-sexual threesome is not to your tastes then move on. If you are too young to be reading this, then move on. ***** I was so bored. Even my dog couldn't shake me out of it and. believe me, he tried. I didn't care t...

Caught!

by centrum1000 on Sep 18, 2017
Transsexuals & Crossdressers

It all happened so quickly that I can barely remember the details. It was a Saturday afternoon and I was doing my laundry in the dorm laundry room when she came in. I've seen her around campus before and regularly pictured her naked body pressed against mine while I pleasured myself. Her name is Carrie. She is almost as tall as I am at about 5'7" with bleach...

A New Roommate

by BigBoySkeletor on Nov 18, 2020
Transsexual

Hello! I'm BigBoySkeletor, and this is more or less going to be my first story to stretch my creative muscles and see if I enjoy the CYOA life over here. So, a few things about the story to begin with; This is going to include furry/anthro content, if you haven't guessed already from the tags or the picture I've used. There's likely going to be multiple bra...

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