Gay Chastity School Stories

7,745 results
Orientation
Length
Source
Infinite Scroll

Progression Ch. 10: Prison

by klapperz on May 1, 2018
Gay Male

Nathan looked around the room for something to do, but it was empty. There was only the bed, which was just a mattress laid out on the floor and a door leading to the toilet. The was a dim light that allowed him to see, but no windows or view from the door as he was in the basement after all. He thought about what he could do to entertain himself, and quick...

Blink: Five

by KenjiDeSade on Aug 18, 2017
Gay Male

The following story is a fictional account. The characters are entirely unreal and so are their situations. Thus no direct attention was paid to probability or safety for the characters. Such practices should not transfer over to real life situations. Practice safe, sane and consensual sex. For your own damn good. If you have problems or issues with queer po...

Blink: Four

by KenjiDeSade on Aug 18, 2017
Gay Male

The following story is a fictional account. The characters are entirely unreal and so are their situations. Thus no direct attention was paid to probability or safety for the characters. Such practices should not transfer over to real life situations. Practice safe, sane and consensual sex. For your own damn good. If you have problems or issues with queer po...

How I Found a Keyholder

by 1077ad on Aug 18, 2017
Gay Male

Author's note: This story was written while I was self-locked in chastity, and the locations are loosely inspired by real locations that I have been to with friends. This is otherwise a work of fiction which involves accounts of some things I haven't done (yet!) so hopefully it mostly rings true. Your comments and constructive criticism are more than welcome...

Puppified

by catastropheofcats on Jan 13, 2018
Gay Male

Editor's note: this story contains scenes of non-consentual or reluctant sex. * I was lead into a room where I saw him - on all fours, panting, collared, chastised, and a dumb smile across his face. I bent over, and ruffled my hand through his hair as he pressed against my hand, eyes closed, panting increasing. "What's his breed?" I asked, examining hi...

Gay Lovin' Gone Bad

by Ciceri on Aug 18, 2017
Gay Male

I have always been turned on by the lash or whip. Even when I was a teenager I wasn't so repelled by the idea of slavery merely because the whip was often used. Of course, slavery is bad. I knew there was an occasions when two or more consenting adults got together and used a whip. I just did not know when. I grew older and became aware of such occasions thr...

Master Jakob and Seth Ch. 16

by and9993 on Oct 9, 2018
Gay Male

Chapter 16 - Date night After breakfast, Master went to the living room and got on his laptop to prepare a schedule for his crew at work. I picked a spot on the floor by his feet and sat down there. On occasion he'd reach down and run his hand through my hair but was mostly focused on getting the schedule done. At one point he stopped, looked down at me a...

The Ones Who Come to Homolas

by Varlance on Jan 22, 2020
Gay Male

With apologies to the late, great Ursula K. LeGuin. The following story is a work of fiction. It contains explicit descriptions of sexual situations and explicit and crude language. It is not intended for children. The situations it describes may be unsafe in real life - use good judgement and play safe, sane and consensual. Feedback is very welcome! Email...

The New Slave Ch. 10

by martin_x59 on Sep 14, 2017
Gay Male

Here is the final chapter in Daniels journey of becoming a slave. Warning, this chapter depicts rape and may not be to every one's liking. I hope you have all enjoyed reading this story as I have had writing it. I will be writing more in the future so please do keep checking back. *** It's friday and I haven't heard from Sir all week, I hate it when I don'...

Human Blowjob Machine

by Subkoksukr4u on Jul 17, 2019
Gay Male

"How many cocks you sucked off before this one?" she asked. Like I could talk right now. "Mmmmmmphhhh", I managed between gagging. "I betcha lost count long time ago, huh?" She laughed, knowing full well I had. Lisa had turned me into a human blowjob fucking machine. I was literally strapped down, head in a harness with a rod attached to a variable speed...