Gay Chastity School Stories

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Power Trip Ch. 04

by Wally_West on Sep 18, 2017
Gay Male

Reader Warning: Over the course of several chapters this story will contain cuckoldry, forced-bi, male chastity, humiliation, and other female domination themes. These kinks are not for everyone; if you do not enjoy FemDom themes you will not enjoy this story. * A week had passed since Colin had sucked his first cock in the glory hole. Veronica had held hi...

One Sub Stud Ch. 01

by tazemebro on Sep 14, 2017
Gay Male

AUTHOR'S NOTE: This story is a continuation of the series about Chris Donaldson and Justin Corvino, who were roommates during their sophomore year of college. While living together, Justin turned Chris into his personal cocksucker and submissive - a fate Chris initially resisted, but eventually came to love. Along the way, Chris had other admirers. He gave u...

Master Jakob and Seth Ch. 10

by and9993 on Aug 22, 2018
Gay Male

Chapter 10 - Dinner I brushed my teeth and got dressed, then took off my collar and put it in my pocket. It felt strange having clothes on over my plug and cage but I was eager to see where Master would take me. We got in the car and drove to a nearby restaurant. It turns out Master wanted just a night out with the two of us. We got seated and he began by...

The Pet Ch. 02

by Gman26 on Aug 18, 2017
Gay Male

Leave real feedback or don't comment at all. Indecent comments will be flagged for the webmaster. ***** I found myself in master's basement with two chairs sitting in front of me. Voices upstairs are definitely my parents. Mom sounds like she's crying. "This isn't how I wanted it to happen!... My baby boy." She doesn't seem to want to come down. Dad sound...

Progression Ch. 13: Unboxed

by klapperz on Jul 3, 2018
Gay Male

Nathan woke up and as usual, removed his t-shirt and briefs then made his way to the bathroom. On his knees, he waited for Kevin to arrive to prepare him for the day. Kevin was frequently late, and today was no exception. Nathan waited patiently for twenty minutes until Kevin finally opened the door and with his phone angled to take a picture. "Smile for y...

Cherry's Graduation Party

by CherryWood on Aug 30, 2017
Gay Male

I finish applying my lipstick and take one last look at myself in the mirror. I'm almost stunned at the reflection that stares back at me. After months of training and feminization I look like the perfect slutty fuck toy. I feel my little cock begin to get hard and strain against my chastity device as I look over my changed body. The strict exercise regimen...

Progression Ch. 03: The Show

by klapperz on Mar 6, 2018
Gay Male

Nathan turned and looked at his clock. It was barely 3am and he was just lying there looking at the ceiling. No matter how hard he tried he couldn't stop thinking about his session with Ryan and Jack. He put his hands under the blanket to feel his cocks prison and attempt to get some relief, but it was useless. When he tried to play with himself his cock jus...

Nephew's Readjustment Pt. 14

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. ***** Nicholas week began with a morning session with his new plastic lover. While the bathroom made things easiest if he was willing to work, morning wood wasn'...

Nephew's Readjustment Pt. 15

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. ***** Nicholas was able to refrain from masturbating that night and the next morning, but only because of the tenderness of his ass. Without access to his genita...

Enslaved by Myself Ch. 03

by Lausunaht on Sep 14, 2020
Gay Male

I was dreading what was about to happen. My master was going to hurt me badly to ensure I would never rebel. I knew this for certain because I would do exactly the same if the roles were reversed. I could only hope that my affection for myself was strong enough to limit the pain. He left me tied up alone for hours, I was thirsty as I didn't drink the whole n...