Sissy Roommate Stories

20,331 results
Orientation
Length
Source
Infinite Scroll

Jesse's Journey Down a Rabbit Hole Ch. 09

by Rebeccasm on Sep 25, 2017
Illustrated

Julie sat in the library trying to study. The photo shoot was still foremost in her mind. She made a lot of money, but the pictures were not what she wanted or expected. Julie made up her mind; she wouldn't go back. No matter how good the money, she wasn't going to whore herself out.. Julie opened her notebook and a picture fell out. It was from the photo s...

Slut for All Pt. 07

by Knightofround on Sep 26, 2017
BDSM

It has been over a month since the night I crossdressed and got fucked by Anthony, a large black man with a massive cock. Vikki and I have gone back to our normal sex routine. The rules of wearing my collar and panties are still there, but she hasn't used a strap on or any toys in my ass for the first two weeks. I guess she wanted to make sure I recovered ni...

Letter from New Piedmont

by justincbenedict on Feb 7, 2018
BDSM

Dear Shoeblossom, I can still remember Rebecca's first comment: "You sure you want to do this, kid?" A full-figured ash blonde with brightly glossed lips...pure Jersey girl. "You really want to move in with me...the sessions aren't enough?" Sometimes the sessions were way too much, but I was lost without Mistress Rebecca. 46 to my twenty-three, she'd bee...

The Challenge - Wear a Thong

by taraterry on Oct 11, 2017
Transsexuals & Crossdressers

There is something deliciously naughty about a boy wearing women's thong panties for a day, after all, the first time you wear a thong all day long, especially on a week day, you will be going about your normal routine. Whether it be to class, to work, or whatever you normally do, you will have it on all day, even when you're not fully sexually aroused. Why...

A Band of Brigands Ch. 1

by All by myself on Sep 17, 2017
Non-Erotic

I hope you like it. I've worked on this project for a long time. Feedback is appreciated. Chapter 1. Jimmy Roberts stood in a line fifteen people deep to punch his timecard in a steamy hellhole known to the locals, and everyone else for that matter, as Katz Industries. He hated his job, but was grateful for it. Here lately there had been a hell of a lot of...

Simply Friends

by puzziboi on Mar 30, 2020
Transgender & Crossdressers

"Hey, Eli," the common law wife and mother of two spoke into her cell phone. She paused a moment then said, "We're around the corner for your place." Valencia Williams ended the call. She looked at her husband, Durrell, who was driving the cash rental car. It was a metallic white gold 2010 Volkswagen Passat station wagon. Durrell, at 34 years of age, was a...

College Crossdressing Confessions Ch. 04

by wifetoy on Sep 11, 2017
Transsexuals & Crossdressers

My wife's control over me insures that I have no secrets from her no matter how depraved my hidden desires. This is the fourth in a series in which I confess my past experiences as a panty thieving college cross dresser. I have changed some of the names, but the rest of the confessions are, sadly, true. Please read the first three installments for context....

How Nathan became Natalie Ch. 01

by saintlycd on Nov 22, 2017
Transsexuals & Crossdressers

My name is Natalie but that was not the name I was born with; rather it's the name my wife gave me when she made me her "sister" and her cuckold sissy not long after we were married. My real name is Nathan but that's a name I would prefer never to use again because I enjoy being Natalie much more than I ever enjoyed being Nathan. This is a story of how my wi...

Super Heroes Ed. 01

by grgy56 on Feb 3, 2020
Transgender & Crossdressers

"Uh..." I stammered. "I can explain!" No I couldn't. On my back and on my roommate's bed, dressed in her sexy undies with my spurting cock in my hand. Let me go back a bit... About six months ago... I said to my work mate, Kara. "My rent is really killing me. I'm going to have to find a new place to live." Kara's eyes light up. "Well... Let me check with...

Discovering Amber Ch. 05

by Ms_Allison on Dec 24, 2018
Transgender & Crossdressers

Mistress notes: To say both amber and Jenn were surprised when Jenn entered my condo would be an understatement. I had given Jenn "some" warning as to what she might find, but she was expecting me to be dressed up for her not amber. Poor amber had the biggest crush and attraction toward Jenn as well, it was hard not to though, Jenn is gorgeous! It was time...