Chastity Stories

6,852 results
Orientation
Length
Source
Infinite Scroll

A Fat BlackOldWomanLove Story Ch. 04

by BlackOldWomanLove on Sep 15, 2017
Mature

Elevator Dreams I'm flattered by the many nice and inspiring responses of the stories I wrote so far. Many are from men, some of women. I've received one from a woman of my own age. She is, just like me, a fat black old woman. We've started a chat session and she told me about a young white man, who lives in the same apartment building. I encouraged her to...

The Best Gift Ever Ch. 05

by Katiekatsman on Sep 15, 2017
Fetish

For the next twenty four hours Mistress Debra ordered Bobby to lay low. She even ordered out for Chinese and made coffee for the two of them the following morning. Following Layla's orders she started the hormone injections the day after surgery and by noon Bobby could already feel a pronounced heaviness growing in his balls. The thought of them rapidly expa...

Flight to Submission Ch. 10

by Cyberdiva68 on Sep 13, 2017
BDSM

Stephanie awoke as a shaft of sunlight speared its way through the curtains, bathing her face in warmth. As she opened her eyes she realised she had not slept so deeply or so well in a long time. All tension seemed to have left her body. She stretched languidly but was recalled to her circumstances by the tugging this elicited from her wrist and ankle cuffs...

Husband Figures It Out

by lover1953 on May 7, 2019
Loving Wives

This is a work of fiction. I hope you enjoy. So, the news of my wife's pregnancy was not what I was expecting. She and her new 'husband' Markus were proudly announcing that he had successfully filled her fertile womb with his baby seed and that she was knocked-up with his black baby. It gave me pause to think carefully about what I had done. I had screwed...

Jennifer Monroe & the Ladies Ch. 01

by corduroysissy on Dec 31, 2017
Transsexuals & Crossdressers

Jennifer Monroe & the Ladies -- Chapter one Jennifer held Debbie's hand as she led him down the stairs and into the finished basement. It was a large single room with a sofa, a few comfy chairs and a queen-sized bed at the far end. Seated on the sofa and chairs were five ladies, all of them dressed in corduroy outfits. Jennifer ignored them as she whisk...

Mom Sent Back to School Ch. 14

by StoryTeller07 on Jan 13, 2018
Fetish

A new boyfriend Janice's stepmother was wearing her school uniform, having just come home from school. There was obviously something wrong. Her mother was hanging around in the kitchen rather than going to her room. She had homework as usual, and getting just the one book out wasn't doing much good, and the woman was getting in the way. *** Some months a...

Neighbourhood Terror to Sissy Pt. 04

by Fibaro on Mar 25, 2019
Transgender & Crossdressers

The next morning Mark was woken up by a loud mechanical voice. "Wakey wakey sissy, time to start your day, and what better way to start it than with another wank." Mark groaned loudly but he did as the voice said anyway. With a sigh he grabbed the boxers of his night stand and Pulled them over his head once more. Since this had started he had spent countle...

Dolled Up To Rock 'n' Roll

by shawnavinyltv on Oct 12, 2017
Transsexuals & Crossdressers

I've always been a rocker, not that I don't love other types of music, too, but there was always something about going to a rock concert that had a special air. A kind of vibe that was hard to describe. Almost like an energy in the crowd connecting them to the band. Of course, I'd been to a number of shows over the years, saw some big bands, some unknowns an...

The Freshman

by Ann Douglas on Oct 10, 2017
Mature

Whitney Pennington paused outside the classroom and took a deep breath. Like so many other college freshman, the short haired blonde found her first day of classes at Northern California State a rushing kaleidoscope of sights and sounds. One that, at times, seemed overwhelming. She didn't think it possible, but her heart was racing even faster than it had...

Katelyn's New Sissy Pt. 01

by bluesbirds on Dec 25, 2018
Transgender & Crossdressers

I remember she made me try the Sissy Peni-Pacifier in the store. It was a humiliating day outing, meant as "my" Christmas gift. Dressed up in a tiny bright red sexy elf costume with marabou trim around the edges that ended at my sissy clit, black fishnet stockings and 4" black heels, with a ridiculously large shiny red bow in my hair, surrounded by mirrors a...