Gay Permanent Chastity Stories

1,087 results
Orientation
Length
Source
Infinite Scroll

Fucked Up Ch. 03

by ruggerjocklad on Sep 14, 2017
Gay Male

The first thing that occurred to me, as the door of the huge master bedroom was locked shut behind me, was how totally fucked I was. Followed shortly thereafter by the realisation that I was almost certainly going to have my arse fucked - for the first time in my entire 37 years on Earth - by some perverse, voyeuristic sadist, in about twenty minutes' time....

Naked Scott Ch. 05

by tattoo_dragon on May 12, 2020
Gay Male

Writer's note: this scenario contains extreme dominance and submission as well as master/slave role play. Just a heads up in case that is not your cup of tea. *** At eleven o'clock on Friday night, there was a knock at my door. My body jumped to attention. My cock started getting hard as I went to let him in. My hand was trembling slightly as I raised it...

A Soldier's Journey Ch. 01

by FenFenScreeScree on Apr 13, 2020
Gay Male

(This story is based on true events. Details have been changed to protect the identity of the characters) Sometimes, I worry if I've gotten too far in over my head... My journey through chastity play is not an easy one, and it's a path that many of my sexual peers would never have had the fortitude to walk down. Allow me to preface this story with what y...

Progression Ch. 14: Befriended

by klapperz on Jul 3, 2018
Gay Male

Nathan woke up earlier than usual the next morning after a night of arousing dreams. He was eager to start work and see what the guys had in store for him. After his daily inspection with Kevin, they both made their way to Ryan and Jacks house. Once they arrived, Nathan stripped and made his way to the basement to begin his daily show. When he reached the...

Eager Boy

by TwistedPanties on Mar 2, 2020
Gay Male

The ping on his phone startled him. "Text when here." He sat nervously in the back of his Uber, en route to meeting a new Dom for the first time. He had been daydreaming about their online conversations online that had started about three weeks prior. He recounted the naughty and perverted things he had shared, and his limits he had discussed, and even ha...

The Chaste Boy and the Locksmith

by fantaseeboy on Oct 31, 2018
Gay Male

A little bell tinkled softly as the door closed behind me. A shiver shot up my spine as I stood there in that little shop waiting to be helped. For a brief moment, I thought about running out the door and living with my current predicament. Just as I was about to act on that impulse, an older man stepped from behind a curtain. He looked to be older than my f...

Progression Ch. 06: Confession

by klapperz on Mar 27, 2018
Gay Male

When Nathan arrived home and entered through the front door, he instantly heard Jeff shout out from the living room "So the lucky boy returns?" Nathan walked into the living room to join Jeff who was sat with Kevin who was playing on his phone. "So who was he? Anyone we know?" asked Kevin who glanced up from his phone. "What, I've stayed out all night bef...

Discovered by a Black Guy

by chastity_sissy on Sep 14, 2017
Gay Male

I should preface this story by saying I've never identified myself as homosexual, but sometimes after being locked up in chastity for a long time combined with crossdressing, I must admit to some fantasies involving other men. I never expected anything to ever actually happen, and it's my own fault really. I had been paying a beautiful, very sexually fetis...

Progression Ch. 02: Regret

by klapperz on Mar 6, 2018
Gay Male

The next few weeks Nathan went back to normal. Wake up, Work, Wank, Sleep. Almost forgetting about his encounter with Ryan. It wasn't until a month later that his urges to lock up his cock would come back. He started to remember Nathan and his offer. "He did say I didn't have to show my face" he thought to himself trying to ease his shyness. He pulled open...

Enslaved Ch. 01

by hasnoalias on Sep 14, 2017
Gay Male

*All characters in this story are above the age of 18 years old* ***** Four men in expensive suits sat around a conference table, as another man made his presentation. The four men were all at the main office of the new and improved United States Male Slave Organization. They had been invited because of their wealth and influence for the possibility of buy...