Male Chastity Stories

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Infinite Scroll

Santa's Sweatshop

by Varlance on Mar 10, 2021
BDSM

Santa's Sweatshop is an adult-only 18+ game that features fictional characters in various situations of a sexual nature. This includes gay (male on male) sex, non-consensual sex/rape, oral sex, anal sex, bondage, chastity, spanking, pain, body-writing and insertion of toys. You should not play this game if you are not 18 or older, or if you might find the ab...

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Night at Amber's

by simple_jack on Sep 14, 2017
BDSM

Stuck in rush hour traffic, Amber lightly shook her head to ward off the oncoming drowsiness that seemed to follow every major workday. As an investment banker, the slender, red-haired 29-year-old was dedicated to becoming a partner at the firm within the next decade. However, such a goal was not without sacrifice. Luckily, she knew what awaited her when she...

Mistress Treva Wins Again

by justincbenedict on May 29, 2018
BDSM

Dr. Shepherdson Grangerford milled about at the fundraiser, his adoring wife, Treva by him, the ultimate arm candy even after all these years. A balding, chubby fellow came up, grabbing Shep's hand. "Dr. Grangerford, everyone is so pleased that you made the fundraiser, and that you'll be heading up the Ophthalmological Wing. We probably couldn't have gotten...

Chastised, Feminized, Sodomized

by Stefani on Sep 25, 2017
BDSM

My name is Kim Lee. I am half Korean and half Chinese. My first name got me teased quite a bit when I was in school. Nor did it help that I am a bit small and slender. Consequently I grew up rather shy and reserved. I never really had many girlfriends, as most women that I ever met seemed to prefer bigger, more macho guys. So I was not prepared at all when I...

Letter from Coldstream Canyon

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: My cousin Glen is married to a dominant bitch called Jocelyn. When Glen and his brother Gavin, both free-wheeling, bimbo-chasing poker-playing drunkards met Jocelyn in a club, they had no idea that the icy blonde would tempt the two of them, and Glen's boss Monroe, into becoming her slave harem! Now Glen hasn't been out for a poker night...

The Office Boy Ch. 03

by Aussie Worm on Sep 25, 2017
BDSM

In the previous episode slaves Samantha and Steven both earned 3 months locked away in chastity for sharing a bed. However Steven earned another 3 months for running away from home for the day. Katrina who was beginning to like her slave invited Steven to her bedroom for the night, although he had to sleep on the floor. --- "Steven wake up." Katrina said...

Sissy's Decline into a Slut Pt. 04

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Six: Chantel's Decline is Achieved, Owned by a Black Master as his Sissy Maid and Slut. I cannot believe at what is happening to me here. Master named Gage is about to purchase me and place me into slavery as his sissy maid and sissy slut. I am near in panic, I want to run away, get into my car and drive for the safety of my home. But I know this wi...

High Stakes Test Ch. 01

by wild_at_heart on Aug 18, 2017
Fetish

Pete found working for a company whose CEO was a woman to be very much like working for any other company he'd worked for. He was praised and given good promotions when his work merited it, and he was very comfortable with the management culture at the company. He'd advanced to the point that he was now being considered for a top management position. It wou...

Cuckold in Chastity

by at_yur_service on Aug 6, 2019
Loving Wives

Mark and Cynthia were out for a walk near their house when they ran across a young, fit asian woman they'd never met before. She introduced herself as Anna, and said that she and her husband Jason lived nearby. Anna proposed that they get together sometime, and they exchanged numbers. Later that week, Anna invited Mark and Cynthia over for dinner and drinks...

Sissy Girl Forever Pt. 01

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

The call from Mistress Andrea made my day. I hadn't seen her for over a week and was looking forward to playing with her & having my chastity finally removed. You should know that Mistress and I have known each other for many years and have I always enjoyed being her sissy sub. Lately she has been training me to be more feminine in appearance. I have been r...