Gay Chastity Bet Stories

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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. 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...

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...

Trained as a Urinal

by Cumpup39 on Feb 11, 2019
Gay Male

Sir is a beautiful man! He is in his mid 40's, 6' tall and has a beautiful hard body. His short dark hair and blue eyes make me weak. He has a perfect cock, just under 7" but thick and I can't keep my mouth off of it! I was his regular cocksucker for a while, coming over whenever he needed to get off. Sir works hard and doesn't have time to date, so I got a...

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...

Progression Ch. 04: A Real Fitting

by klapperz on Mar 6, 2018
Gay Male

Nathan hung out with Jeff and his other flatmates for the day. He had been so focused on Ryan and Jack that it was nice to have a break and be normal for the day. They went to the pub for lunch and then watched some films. Before he knew it, the day was over and everyone was heading for bed. The next morning Nathan woke up for work. He panicked, remembering...

Guys' Retreat Pt. 05

by Cyanlot on Apr 21, 2020
Gay Male

Part 5: Brianna's Training "Vince had a terrific idea, Brianna," Kent said. "It's really going to make this easier for you." "Yeah," I said, noncommittally, knowing full well that whatever Vince had come up with wasn't going to be to my benefit, though I was sure it would benefit them. "Yeah. We've been downloading some videos for you to watch. You're goi...

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...

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...

Top Becomes a Daddy Bear's Boy Pt. 03

by DaddyBearChaser on Jul 6, 2020
Gay Male

Just as I opened the bathroom door, I heard Mike say, "Boy, make sure you sit down to take a piss. The last thing I need is you making a mess in there" before he began laughing to himself. "Fuck, I have to sit down like a girl to pee. At least Mike won't be watching the humiliating act," I thought to myself as I made my way to the toilet, bladder full of mo...