Roommate Chastity Stories

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The Perfect Life for Davey Ch. 06

by PeterOmez on Sep 16, 2017
BDSM

In the morning Dale required a quick blow job before he let me go. At about 5:50, I bolted out of the cab of his truck like a bat out of hell, laptop under my arm, and raced to my parents' car to drive home. When spring semester started and we were back at TU, I resumed my hellish existence as Tyler's (and Shelly's) complete and total slave - or, "good frie...

The Roommate Pt. 12 - Miranda

by ValoryG on Sep 19, 2017
Transsexuals & Crossdressers

Chastened, Josh/Lori nursed her wounds for days, and little was said between her and Miranda, except when the dominant asked how Lori had opened her chastity when with Cassie. "I bought a master key on the Internet," answered Lori brightly. "Actually, my penis is getting a little irritated by the plastic over such a long time." "Give me the key. It obvious...

Roommate Beyond Fantasy Ch. 13

by EisAlntheia on Sep 12, 2017
Fetish

This is one of my first fictional works and may not be great in the eyes of others. I’m willing to learn but from the perspective of women and women only. Since I cannot claim to know what lies in the minds women…especially the dominant woman, I cannot effectively provide the best written stories. I seek feedback from ALL women, but greatly encourage opinion...

Her Butler Pt. 04a - Alternative Ending

by patannon on Oct 19, 2020
BDSM

Her Butler Alternative Ending © Pat Annon 2020 [This is an alternative to part 4 of the story series, Her Butler. It is an exploration of consent and non-consent in a long term D/s relationship.] Jennifer was at his bedside when her butler died. "Complications following his stroke." Memories of a life well lived flooded the room as she processed his final...

College Ponygirls Ch. 01-02

by Sarahcheer on Sep 12, 2017
BDSM

Chapter 1: Arrival Sarah sat in the back of her parents' car as they drove down the rural highway towards a college that had accepted her, and given her a full ride scholarship. She thought back on the letter she had gotten from a college up the road they were now driving on. She hadn't applied for it, but the school had heard of her, and sent her an accept...

Her Butler Pt. 04

by patannon on Aug 17, 2020
BDSM

She was at his bedside when her butler died. "Complications following his stroke." Memories of a life well lived filled her heart as she processed his final words. Back a half century, when she was not yet 30, she posted her ad on Craigslist. Jennifer graduated college and law school near the top of her class. She snagged an excellent offer from an interna...

Revealed to My Roommate Ch. 01

by gaildaniels84 on Jan 6, 2020
Transgender & Crossdressers

Paul watched the clock on the office wall with rapt attention. He'd finished his work hours ago, the truth was doing the minimum at this dead-end office clerical job didn't take more than a couple hours of hard work a day, and since then he'd tried everything to distract himself. He'd been to the water cooler a suspicious number of times, taken several bathr...

Master Squirrel

by justincbenedict on Jul 29, 2019
BDSM

Orson looked at Squirrel hopelessly. "I really need to get out of this thing, dude." Orson was standing in the middle of their living room, naked but for his chastity device, and looked really desperate. Squirrel snorted. How strange things had gotten in the past nine months. Squirrel was a bit of a geek, and had been kind of flattered when the most popular...

The Roommate Pt. 10 - Miranda

by ValoryG on Sep 13, 2017
Transsexuals & Crossdressers

True to her word, Miranda made sure Josh/Lori ventured out in public some more before his teaching duties resumed. The butt plug was frequently inserted, and when Lori asked why, Miranda remained mysteriously opaque about it. Lori was becoming more accustomed to the sensations down there - sometimes pleasant, sometimes a turnoff. After the movie (and the w...

Sun Hee Ch. 03

by metalimbic on Sep 18, 2017
BDSM

Try to imagine my walk home that night from Sun Hee's dorm, after having just been caged by her and then unceremoniously dismissed. It was a long walk in the dark across campus, and that gave me a lot of time to think and a lot to think about. But in truth I really only thought about the cage that was now locked around my sex. It felt like some invisible fo...