Sissy Roommate Stories

20,331 results
Orientation
Length
Source
Infinite Scroll

Roommate Ch. 02

by corsetheelscollar on Sep 17, 2017
BDSM

The week had gone by. My legs were still smooth. I slid my hand inside my dressing gown and felt my hairless balls. I'd loved being forcibly dressed by Stephen and Shellie, but the vengeful man in me wanted to get my own back. How could I find a punishment that Stephen wouldn't enjoy? He was into all sorts of kink. I doubted that there was anything he would...

My First... Turned Me Fabulous!

by BerkeleyJanine on Sep 16, 2017
First Time

I'm lying in the bed of a man who picked me up outside a gay bar a few hours ago, listening to the sounds of his gentle, contented sleep. Contented from my having given him delicious head, contented from having fucked me with my stockinged legs wrapped around his shoulders. I'm lying here, looking at the trail of clothing that marks our evening: my strap-y h...

The Pantysissy Diaries Ch. 02

by JPantyboyVSL on Jun 5, 2018
Transsexuals & Crossdressers

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapter 1 before reading chapter 2. *** The Amtrak train Jaymie was onboard with his new Mistress, Sydney had just pulled into NYC. Jaymie had to get...

Feminizing First Step Ch. 06

by antares34 on Jun 1, 2020
Transgender & Crossdressers

(All characters are age 18+) Today my mom was having her friends over for a pool party in our backyard. They had been here all afternoon --mainly lounging around the secluded swimming pool and patio area. Michelle had been first to arrive. She was my mom's old roommate from university and came wearing a black bikini and floral print sarong. Next was Kendra...

My Girlfriend's Sissy Roommate Ch. 04

by SEVERUSMAX on Nov 21, 2017
First Time

"So, you softened up faster than I expected on the issues of fellatio and vaginal sex, babe. Not that I mind, as it's between you and Rain, and I think that it's rather sexy, anyway, but what prompted that? Just the knowledge that Rain has meekly accepted his lot and will be a loyal husband to you? I wouldn't go so far as to call him a cuckold in the typical...

Slut for All Pt. 04

by Knightofround on Sep 26, 2017
BDSM

Two weeks after Greg and Maggie came over, Vikki had to go away for a few days for a business meeting. I was a little upset because I had gotten used to being around her all the time. I was also going to miss the amazing sex. We both agreed to no self pleasure during the break. It was going to be very tough and I needed some serious distraction so I headed t...

New Gurl in Town Pt. 02

by GavinIsaNuisance on Oct 5, 2020
Transgender & Crossdressers

This story and its contents is entirely fictitious. Any similarities to persons or things living or dead is purely coincidental and entirely unintentional. All persons depicted in a naked/sexual manner are 18 and up. Andy begins his sissy adventures as Bianca, but will he be able to woo his crush Riley, or will he be forced to be Carol's bitch forever? We...

The Exploits of Cockslut Kelly 02

by CSK on Sep 11, 2017
Transsexuals & Crossdressers

Hello again my fellow dirty minded peeps. Welcome back to the second installment of my ongoing series detailing my obsession with the male member and how I use my cute looks, tight tiny body and willing holes to let men fulfill their desires and fantasies. As promised in my first chapter intro, this story is also certified as "pee-free" so no one will be usi...

Reawakening

by magmaman on Aug 19, 2017
Exhibitionist & Voyeur

I married Lee because she was naughty, simple as that. I dated a lot prior to meeting her, never settling solidly on anyone. I don't even know what happened there for sure, I had no plans or even any inclination to hook up with any woman full time. Besides, she wasn't my type. Not my type at all. The first time I saw her she was up on a stage wearing nothi...

The Hardest Kind To Be Ch. 01

by Joe Wordsworth on Sep 16, 2017
First Time

In the offhand chance that you don't find the setting clear on the issue, all characters are eighteen and legal. This is also a madly different story genre than I'm used to writing, so be kind. . . .. ... ..... She hated her. Hated... though strong and dramatic, it was the only word that summed up their relationship. Nobody would have guessed it, but i...