Chastity Roommate Stories

20,671 results
Orientation
Length
Source
Infinite Scroll

Sun Hee Ch. 05

by metalimbic on Sep 18, 2017
Fetish

NOTE: Expert-level readers should ask themselves whether Sun Hee would want them to cum or whether she would expect them to cum only if and how she allows her chastity boy to cum. ***** After Sun Hee fucked my face that afternoon, she fell exhausted into my arms, and we had a long and very frank talk about everything that had been happening over the last s...

The Roommate Pt. 13 - Miranda

by ValoryG on Sep 19, 2017
Transsexuals & Crossdressers

Lori left the bed before Leigh Ann woke up from her nap, and Lori again wished she wasn't wearing chastity. If only she could defeat it like before! But having to laboriously dial through 999 combinations on the tiny lock didn't appeal to her (although a hacksaw would probably do the job in a crude way). And so, still horny after the session with her new r...

The Roommate Pt. 08 - Miranda

by ValoryG on Sep 16, 2017
Transsexuals & Crossdressers

Lori became used to the chastity regimen, the occasional Nair, the wig (Miranda estimated only a month more with it), and continued dutifully teaching Josh/Lori's college classes on into the spring semester. She began to wish she could dress as Lori all the time, and when at college or researching in a library, sometimes ached to be feminine, and to look a...

Her Butler Pt. 03

by patannon on Sep 14, 2020
BDSM

The next few years were very happy ones for him. His job meaningless, his great passion Miss Kendall's home. She set goals for his health, sending him to a personal trainer three evenings a week. He took additional cooking classes, especially baking and pastry. His whole life revolved around hers. Every evening he looked forward to the moment she walked thro...

Summer in Chastity

by denny_micum on Aug 26, 2019
BDSM

Summer laid on her bed. She was only three days past her high school graduation but already feeling the boredom from summer creep in. It was a rainy day, and none of her friends were around to hang out. Her parents were gone, and no one else was in the house. As she laid in bed, her skirt gently slid down her legs. Suddenly the mood struck her. As one hand...

His Black Master Ch. 07

by NickJBella on Sep 19, 2017
Interracial Love

Kevin was naked on his knees, his cock encased in a steel chastity device. Ty's hard black cock was sticking straight out, inches from Kevin's mouth as if it were a microphone. Kevin cleared his throat. "Permission to speak, Sir?" he asked "You may speak," Ty replied in an authoritative voice. Kevin began to speak. His voice was quiet and steady. "Kathlee...

The Roommate Pt. 06 - Miranda

by ValoryG on Sep 16, 2017
Transsexuals & Crossdressers

Josh/Lori continued to endure a burning ass throughout most of the following day, but by the time he returned from teaching, the sting was more of a memory. He helped prepare the evening meal just as Miranda directed, reveling in his/Lori's long skirt, breasts, hairdo, earrings and bracelets, and slip-on sandals with heels. She had even applied a little li...

Beauty and the Bully Ch. 02

by xaitonnar22 on Sep 13, 2017
Transsexuals & Crossdressers

To all outside appearances, the young woman standing somewhat impatiently next to the mailbox was just like any other woman. She was slightly above average height at about five foot six and had long, curly brown hair, which, much to her distress, tended to be a mess in the morning. Now, however, it fell gracefully to frame her face in soft curls. Her skin wa...

The Perfect Life for Davey Ch. 07

by PeterOmez on Sep 16, 2017
BDSM

Since I always had to get Tyler's permission for every little thing I did, I asked him, one day in April, if I could call one of the factories in Bellewood to ask about summer work. His reply shocked me. He said, "No, you're not gonna be in Bellewood this summer, Davey, you're comin' home to Keenesburg with me." "What? No. No, I... I can't do that, no... u...

BDSM by the Book

by Stefani on Sep 11, 2017
BDSM

I was rather slow when it came to dating. My love life moved at glacial speed until I met my wife. In high school I was skinny and too short to be any good at sports. At school and in the town I grew up in outside Sioux City, I got pushed around a lot by other boys, all of which translated into a lack of confidence. Particularly around women. When I got to...