Sissy Roommate Stories

20,331 results
Orientation
Length
Source
Infinite Scroll

Halloween Party Aftermath

by Sabnock on Oct 19, 2020
Transgender & Crossdressers

Oh my GOD I'm so hungover. I creak my eyes creak open, and immediately regret doing so. Everything hurts. My head is pounding. My mouth tastes like something died in it. I try to sit up, pause, flop back onto the couch. At least I've got blanket. Wait... I'm not in my bed. Where the fuck am I? I rub the back of my hand over my eyes, feeling a weird, heavy...

Slut for All Pt. 05

by Knightofround on Sep 26, 2017
BDSM

It's now been about 3 months since Vikki first sat on my face and had me eat Anthony's cum from her pussy. We have been having amazing sex almost every day since then. She learned about my friends Greg and Maggie's extremely open sex life that is full of threesomes, bisexual encounters and cum covered bondage orgies. Last week Vikki caught me jerking off whi...

Nikki Goes to College Ch. 02

by Latexsissy69 on Sep 25, 2017
Transsexuals & Crossdressers

The next day, I awoke to the sounds of someone screaming, I didn't know what it was at first being disoriented. I looked around the room and quickly began to realize that I was still in Primington Academy. It hadn't been a bad dream. I saw my roommate, Missy, across the room sleeping still. She must have gotten used to the screams because she was still out l...

The Rendezvous Ch. 02

by CassidyCaine on Sep 26, 2017
Transsexuals & Crossdressers

(Author's note: I have tried to get an editor for this story but failing that after over a week of looking I'm publishing it. Please be aware this work has some fictional coercion and other sissification elements.) Nick tried to hold back as tears welled in his eyes but the finally started to stream down his cheeks in black rivers. His make-up was alrea...

Topped from the Bottom Ch. 05

by cutebabysadie on Sep 14, 2017
Fetish

Summary of previous chapters: Chapter 1: Todd, college football quarterback and alpha jock make a bet with his short nerdy vocal music roommate, Mark. The bet was that Mark could fuck Samantha, Todd's girlfriend, better than Todd. To be more specific in just 10 minutes she would be orgasming and screaming Mark's name. It ends with Todd humiliated on his kne...

And He Called It Research

by thornapple on Sep 14, 2017
Novels and Novellas

Philip Johnson Prologue The offer of impressive things for free creates greed. Start by throwing in a generous amount of free vacation with impressive free goodies, and all worth tens of thousands of dollars. Add a few vital ingredients like...well let's throw in a great amount of nudity. Add a lot of passion and lust, and cook the recipe in a hot tropi...

Big U Pride Ch. 02: Going Deeper

by latinarita4 on Jun 2, 2020
Transgender & Crossdressers

Please read Chapter 1 to get the full experience and context! This chapter owes a lot to the SissifyYourself and SissyFactory content. You should check them both out! I also owe a lot to Drogon's hypno videos! ***** The 90-foot yacht cruised down the placid clear blue waters, making its lazy way past sun-specked islands. The Mediterranean waters were par...

Virgin Femboi

by sollilolli on Aug 1, 2018
Transsexuals & Crossdressers

I had finished my schooling and came to New Delhi to join college. I tried to get into the hostel but the seats were all full and the ones left were up for those students with deep pockets who'd 'donate' to the institute. Now I needed a place to stay as I couldn't stay in the hotel forever. So a friend of mine told me about this boy who was also looking for...

Sissy Crissi Ch. 01

by sissycrissi on Sep 11, 2017
Transsexuals & Crossdressers

Chapter 1 -- One Dreamy Night Like most Friday nights, my roommate Erika would be gone tonight. She and her new boyfriend, Leroy, were taking off for a private weekend. Erika and I had met about two years prior, when we were introduced by a mutual friend. Being fresh off a divorce, I was in need of a place to stay, and Erika was in need of someone to help w...

Twist

by Seurat on Sep 12, 2017
BDSM

Once, long ago, I got fed up with the way femdom, forced transgender, and loving wife stories with BDSM basis ended; they had grown very predictable. In fact, a few authors had posted short lists of vignettes which, unintentionally, encompassed all of the common endings which I had grown to abhor. My own list, a response to the predictability of those storie...