Chastity Roommate Stories

20,671 results
Orientation
Length
Source
Infinite Scroll

Aunt Carla Ch. 05

by moterhead74 on Sep 12, 2017
BDSM

This is part of a short story, if you haven't read the previous chapters, I would encourage you to start with chapter 1 and read them all in order. Chpt 5 I went on my date with Amy. She was wearing tight jeans with what I'm guessing was ankle high, high heeled boots. She had a leather jacket on; she was very attractive. We went out for a nice supper, and...

Miles's Conundrums Ch. 09

by justincbenedict on Sep 16, 2017
BDSM

Gretchen completely stubbed out her cigarette on my tortured glans, and then held the butt up to my face. "Swallow it!" she demanded. I shook my head, and she punched me in the stomach. I buckled over, straining at my hands cuffed behind my back, and as my mouth opened, Gretchen shoved the disgusting butt in, and held my nose until I swallowed it, retching....

The Roommate Pt. 04 - Miranda

by ValoryG on Sep 16, 2017
Transsexuals & Crossdressers

There really was no choice to be made. Josh was hooked, and hooked good; Lori beckoned, and Miranda was breathing life into her. So a wardrobe was to be purchased. Fortunately, Josh had some money from an inheritance, but he usually kept that money aside for the day when he might need to return to college or make a down payment on a house. That weekend,...

Night Out

by fantasycuck on Sep 17, 2017
Fetish

Tonight was the night that we had been thinking about for a while now. Your roommate was going home for the weekend and we would have the apartment to ourselves. Friday started off great. I awoke to you stroking my morning wood, working my shaft with one hand and tickling my balls with the other. You whisper to me "Guess what is going on this after you cum?"...

Lydia Ch. 05

by femmed on Sep 25, 2017
BDSM

With all my senses occupied, I had no idea how long I was tied to the bed. Jen's recorded orgasm could have been anywhere from five minutes to half an hour long, for all I knew. I didn't hear Lydia come in; I'd briefly worried that Jen might have forgotten the keys, and that I'd be trapped here until my roommate got back on Sunday, but sure enough, the musi...

Delving into Femdom Ch. 01

by readytokneel2907 on Jun 1, 2020
BDSM

**Chapter 1. Growing up Oh my where to begin, I imagine it is best to start at the beginning (or as close to it as I can remember). I grew up in a relatively medium sized east coast city living what some may call a normal life with two sisters and both my parents. Growing up I was always into sports and when I entered middle school I had begun to focus on b...

Awakenings Ch. 29

by Goodhusband on Sep 25, 2017
Loving Wives

Wednesday January 15th, two full weeks had now passed since I took Jeanne, the girls and Paul to the San Antonio airport. While the previous few days had been filled with excitement and I now had Maureen Styles as a friend, I missed my wife, my daughters and Paul. I also missed my friends Ruth and David and Amy and Mel. I wanted to go home, but it wasn't yet...

Pantied and Cucked By My Wife

by TammyPanty on Jul 27, 2020
Transgender & Crossdressers

I met the woman who became my wife through a former college roommate. My ex-roommate had known about my history of wearing women's lingerie and my enjoyment of dressing as a girl. He told me he had met a female fertility doctor who had told him she was really turned on by males who liked to dress and act as females. My roommate gave me her phone number and...

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...

Bag-Face's Debut

by justincbenedict on Sep 17, 2017
BDSM

Kyleen boredly turned "Antiques Road Show" off. Ky felt her phone beeping with texts from her former submissive... Maripat--the poor idiot back in Smeaton. Maripat who had been affectionately called "Livermush" by Mistress Kyleen was really going through withdrawal... Offering Ky money or a trip to Paris... Maripat could afford it--she was the vocalist...