Gay Chastity School Stories

7,745 results
Orientation
Length
Source
Infinite Scroll

Becoming a bitch

by Testytesterton on Nov 28, 2019
Gay

(Skip this if you don't like boring behind the scenes stuff. Wow! Over 3000 likes and story of the week for my first story here! Thanks to everyone who has liked, bookmarked or commented. The feedback lets me know what works and what might need work. I would love for this to be the most popular story in its category, so if you like the story, "like&quot...

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Guys' Retreat Pt. 01

by Cyanlot on Jan 20, 2020
Gay Male

Part 1: Going Away with the Guys "No!" Nicole was adamant. "You're not going, and that's final!" "But I have to," I said, trying not to sound like a whining teenager—or, worse, an impotent wimp. "We've been doing this every year since we were in college." "And what happened last year?! ..." She just let that hang in the air and I didn't really have a go...

Fixing the straights

by cdbaby on Dec 28, 2016
Gay

You wake up and prepare for your day, unaware that this would be the last day you would be considered straight. You shower as you did every morning and felt the water's warm touch as it cascaded over your skin. You could stay here forever if you could. But you need to start your day and the hot water would run out before long. You wash your hair, then the re...

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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...

Progression Ch. 01: Finally

by klapperz on Oct 15, 2017
Gay Male

Nathan paced around the shop for a few minutes while building up the courage to purchase the chastity device. This was his first time inside a sex shop, and he was very uncomfortable. He saw shelves full of different toys, each one exiting his mind with sexual thoughts. He noticed the device he wanted was behind the counter, but in order to seem less awkward...