Chastity Pegging Stories

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Made to Obey Ch. 11

by madetoobey on Aug 21, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). I'd been forced into a chastity cage and made to wear panties all the time. Humiliation was now a frequent event. Esther, who had investigated my internet usage on my laptop to see if I'd visited shema...

Family Chastity Story Ch. 02

by antares34 on Jul 3, 2019
BDSM

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. ***** Having grown bored with how things were progressing with my sissy son, I have recently ventured into a new and fun project –filming and distribu...

Pegging for Promotions

by TheDougler80 on Sep 18, 2017
Fetish

Doug was less than five years out of college, only in his late twenties and had already started one of the most successful businesses in his city. It seemed as though he had made every right decision since leaving school. That is, until he decided to hire a personal assistant. There were a number of qualified candidates, but when Melissa walked into his off...

A Virgin released from Chastity

by ronron1818 on Nov 16, 2020
Fetish

It was time to move on... I will be graduating today, 4 years after moving in with Ruth, and tomorrow, I will be moving out to start my life as a grown up. I already found a job in my home town, and rented a small apartment near the new office place. Ruth came with me and my parents to the graduation event. My parents liked her a lot. For them, it was lik...

Black Bulls in Chastity!

by Samuelx on Oct 3, 2018
Interracial Love

Meet Bartholomew "Bart" Jones, a big and tall young Black man living in the City of Ottawa, Ontario. Born in the City of New Orleans, Louisiana, Bart moved to the Canadian Capital to expand his horizons and explore new things. He had a Business Management degree from Louisiana Tech University, and felt like giving life in Canada try. Life in Canada had alway...

Begging for a Pegging Pt. 02

by Cirkle7 on Oct 12, 2020
Fetish

This story is dedicated to the muse who inspired it. I think she would most certainly enjoy taking the reins in the bedroom. In fact, I think she may have pleasured herself while she read the last story. Thanks again I'm speechless, but I love your dirty mind! All characters are above the age of eighteen, please this story may not be for you, but don't read...

Alice and the Looking Glass Ch. 18

by LeopoldNicholas on Sep 14, 2017
Erotic Couplings

Willow tightened the straps holding Jack of Hearts wrists to the pegging horse till the flesh turned first bright crimson then the palest shade of blue. Normally the recipient would be expected to react vocally in some way but the insertion of a pair of her freshly soiled panties before the usual ball gag completely silenced any lamentations from being more...

A Strapon Tale Pt. 02

by damn_thats_me on Mar 2, 2020
Fetish

All the events in this story really happened, only the names have been changed. Warning: contains themes of pegging, femdom, leather & latex, chastity play, and mild cuckolding. *** As mentioned in our last story Alex (29) and I (36) are both switches, and enjoy taking turns dominating each other. We had been dating for about a year now. Yet while we met...

A Strapon Tale Pt. 01

by damn_thats_me on Mar 2, 2020
Fetish

All the events in this story really happened, only the names have been changed. Warning: contains themes of pegging, femdom, leather & latex and chastity play. Alex (29) and I (36) had been seeing each other for about a year now. During our first date I immediately sensed that she had kinky potential. There was simply something about her looks and attitud...

The Facility Ch. 07

by spankmehard1984 on Sep 14, 2017
BDSM

When Miss Kate left The Dungeon, she was feeling quite proud of herself. The first clients to The Dungeon had been locked in chastity for a week, flogged, paddled, and put in predicament bondage. In addition, Miss Kate had Vanessa lick her pussy, followed by Miss Kate pegging Tim and finally some bondage fucking. Miss Kate then locked them back in chastity a...