Roommate Chastity Stories

1,000 results
Orientation
Length
Source
Infinite Scroll

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...

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...

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...

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...

Roommate Beyond Fantasy Ch. 09

by EisAlntheia on Sep 16, 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...

Roommate Beyond Fantasy Ch. 10

by EisAlntheia on Sep 16, 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 opini...

The Roommate Pt. 15 - Miranda

by ValoryG on Sep 19, 2017
Transsexuals & Crossdressers

Note: For those who may be jumping into the story only in these advanced chapters, know that Lori is Josh. At home and often around town, he's a woman. When Lori is teaching college, and with family and so on, he's Josh. ***** Lori had obtained his chastity device's combination from Miranda before she departed, and the impediment was quickly removed. Now,...

My roommate new sissy maid

by Carterdruzba on Dec 29, 2020
Interracial

I been living with Gina who happens to be muscular and stronger than me I haven’t paying my rent for 2 months so one day when I meet her in the living room “you been not paying for months so I have idea for you to repay me so I got this” it was a pair of pink panties heels and black stockings and a maid dress “I decided to should be my maid until you paid me...

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Roommate From Hell Ch. 01

by billboy90 on Sep 13, 2017
BDSM

'It is a rather weird morning' I thought as I was waking up. At that time I didn't know why I thought that but there was a certain feeling to me that things would unfold quite quickly. I stood up and rushed into the bathroom. I certainly should have thought better as by entering I was for a big surprise. I caught Catherine as she was exiting the shower with...

Roommate Beyond Fantasy Ch. 08

by EisAlntheia on Sep 16, 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 opini...