Chastity Roommate Stories

20,671 results
Orientation
Length
Source
Infinite Scroll

My Master

by SissyKaty on Mar 26, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** I pulled into the driveway to my house and I was disappointed to see my future mother-in-law's car in the driveway. "Oh great" I think sarcastically. I'm not looking forward to interacting with her so soon after getting off work. I had just come from a long day working in IT for...

The Roommate Pt. 05 - Miranda

by ValoryG on Sep 16, 2017
Transsexuals & Crossdressers

Josh/Lori couldn't stop thinking about Miranda's tear as they continued their daily routines. It was the first time he'd seen a chink in her armor -- that owning him was as important to her as his irrational desire to become Lori was to him. Amid mood swings, he told her he'd make his decision by the following weekend. In Josh's classes, he operated mostl...

Black Cop's Stress Relief

by puzziboi on Jan 20, 2020
Transgender & Crossdressers

"We think you're doing a hell of a job, Corporal," the bronze-skinned police lieutenant explained. "But at this time we're going in a different direction." "Alright. Thanks for letting me know, Lew," replied Christopher Patterson with a fake smile. "Is the candidate internal or external?" "External," the supervisor revealed. "Alright. I'm kinda tired," Cp...

Chastity Resort Pt. 03

by handyrandy9 on Sep 25, 2017
Fetish

Anna slept for about an hour, exhausted from her explosive orgasm. I, on the other hand, was wide awake, thinking about my new found arrangement. It was a lot to take in; I still wasn't sure exactly how far Anna wanted to take this. I expected she would break by the end of the week and let me have some relief of my own. Anna showered quickly to freshen up,...

The Little Mermaid

by CopyCat13 on Sep 13, 2017
Fetish

Brittney and Shikha have been best friends since they were in middle school together. It was only natural that when they both moved away to the same college that they become roommates. This got a bit awkward between them at first as they learned to live with each other and learned some new things about each other. But they quickly learned to live together in...

Letter from West Whitacre

by justincbenedict on Dec 2, 2019
BDSM

Dear Shoeblossom One night, some years ago, I came home late from work, and at the time, I had a tenant, Pilcher. Pilcher has always had the hots for me, he was just a friend for the longest time, and then I found out he had two avocations--one was to move out of his parent's basement, and the other was a deep interest in BDSM I had once shared my group...

The Roommate Pt. 11 - Miranda

by ValoryG on Sep 19, 2017
Transsexuals & Crossdressers

Josh/Lori, having lost her virginity to Miranda's penetration, and feeling even more like a woman, settled into teaching again. The rewards of passing on his passion for literature to young students was considerable, and now he could increasingly see characters from male and female perspectives. He was especially interested in learning how his female student...

Laura Learns Her Husband's Secrets Ch. 03

by lesliejones on Sep 13, 2017
Fetish

To J.J., who has stuck with me the longest * When we last left Jack, dutifully licking Elaine's slit under her skirt, he was beginning to panic because he realized that her thin-lipped vulva would limit the air intake for him, especially after the sadistic girl began releasing jets of pee into his mouth. "I know that it must be a bit close for you down t...

The Wedding Present Ch. 02

by je8452 on Sep 14, 2017
BDSM

Dear Loraine, I'm a friend of Natasha's cousin Sandra. Natasha asked her to suggest that I contact you as I live here in The Islands. I'm sure that I can make your time here memorable. You can contact me at ***-***-**** from 8 AM until 5 PM daily. I'll look forward to hearing from you. Leilani The letter was waiting for her when we arrived at the hotel. I...

Laura Learns Her Husband's Secrets Ch. 04

by lesliejones on Aug 29, 2017
Fetish

To J.J., who has stuck with me the longest Jack was dutifully licking Elaine's slit under her skirt and beginning to panic because he realized that her thin-lipped vulva would limit the air intake for him, especially after the sadistic girl began releasing jets of pee into his mouth. "I know that it must be a bit close for you down there," Elaine giggle...