Sissy Roommate Stories

20,331 results
Orientation
Length
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Infinite Scroll

Casey's Submissive Journey Pt. 12

by corduroysissy on Jul 31, 2018
Transsexuals & Crossdressers

Mistress Maxi -- Part 1 Maxine Montgomery was sixty-four years old, five-foot seven-inches tall, and one hundred and forty pounds. She was an attractively handsome woman whose looks and demeanor were very similar to the character Katherine Chancellor on the soap opera The Young and the Restless. "Distinguished" was a very good adjective for Maxine, "arrogan...

The Secret is Out Ch. 01

by erinssilence on Sep 16, 2017
Transsexuals & Crossdressers

This story is not based off a true story. It is about a crossdresser who chooses to go to a conservative christian college only to be found out by their roommate. The story is a bit slow going at first but is necessary to set up the remaining chapters that are to come. **************** My name is Kelsey. Well, actually the name I was born with is Kevin but...

Savannah's Hypnotic Socks Pt. 21

by Fibaro on Dec 24, 2019
BDSM

Chapter 25 After a few intense nerve wrecking minutes of waiting Roxanne felt a rather pleasant feeling much to her surprise. Someone was rubbing some kind of cream right above her pussy in circular motions. It felt rather pleasant yet at the same time it also felt so wrong and embarrassing. To make it worse she couldn't help herself from moaning around the...

Slut for All Pt. 01

by Knightofround on Sep 11, 2017
BDSM

"That's it baby! You are such an amazing cock sucker!" I moan around the cock in my mouth as I bob up and down quickly. I feel hands on the back of head grab my hair to stop me from moving up and down the amazing 10 inch cock. I've been kneeling for almost twenty minutes slowly working this monster. I've only been able to take just over half of the cock so f...

Susan

by FredTR on Apr 17, 2019
Transgender & Crossdressers

It's important to understand that even though I had sucked cock before, it had been many years ago. A few times experimenting when I was younger, over a decade ago, was all I had done. And now... well, I'm getting ahead of myself. Justine (my wife) and I had been married for almost 12 years. We were both in out late 30s, closing fast on 40. We had one son t...

A College Sissy Ch. 02

by nat_rose on Sep 26, 2017
Transsexuals & Crossdressers

When I woke up the next day I was hit with guilt and shame. Bo was gone and I laid on my back, staring at the ceiling. I was dressed in the white silk nightie, and the pink bra and panties from the night before. My ass was sore from the pounding and my face was caked with leftover makeup. I felt bad physically and emotionally and so I started to cry. This i...

My Girlfriend's Sissy Roommate Ch. 06-07

by SEVERUSMAX on Jul 17, 2018
Transsexuals & Crossdressers

Chapter 6 "So, you're the famous, or infamous Jessica, then?" Larissa teased my wife as she stepped inside her house. "And you're ... Larissa, my husband's new mistress or girlfriend or whatever. Who is she? That woman! Wait ... is that ... Rain? My God, you look like a woman! So ladylike, so exquisitely feminine ... wearing a wig, makeup, and lingerie, to...

Lady Esolen

by justincbenedict on Jul 30, 2019
BDSM

Esolen smiled at Claude. She shook her short dark hair. It was a bob, easy to control, but quite thick, and a bit curly. Claude stood in front of her, weeping slightly, and holding the thick leather strap. "Claude, we talked about this." Esolen's soft voice resonated. Esolen never raised her voice. "There are rules and consequences. When I moved in with you...

Eve Quest

by JJ Neal on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 1 My name is, or maybe we better make that was, Andy Moore. Until recently my personal identification was in the name of Jamie Jo Moore and everyone I knew called me Sissy. My parents died in an automobile accident when I was twenty-four years old leaving me an estate of around $3,000,000.00 and an eighteen percent interest in an insurance company...

Steph and Giulia Ch. 06: The Strapon

by BigHand32 on Sep 16, 2017
Fetish

Stephen felt embarrassed. How had he got himself into this? Wearing cutoffs and tights to school? He expected to be mocked and called names, by everyone. Maybe it was more awkward today... sometimes Stephen thought he caught someone looking, in the distance, but by the time they reached him, their head was turned away. Was it his imagination? Sometimes he th...