Gay Cuckold Chastity Stories

356 results
Orientation
Length
Source
Infinite Scroll

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...

It Could Be Worse Ch. 07

by eviltwin52 on Sep 14, 2017
Gay Male

We've been in service to blacks for 6 months now. Mom, my wife Cindy, and I have completely devoted ourselves to the pleasures of the Superior African race and Leon. The club where Leon has us working is a nice dinner club on the waterfront in S.W. Washington, DC. We work as greeters and servers with a few other white couples and single white women. All of...

Power Trip Ch. 05

by Wally_West on Sep 26, 2017
Gay Male

Colin stood in front of the toilet relieving himself through the opening at the tip of his chastity cage. He was growing used to its weight and presence, finding less discomfort from the device every day. He was happy it was Saturday and he didn't have to go to school; Colin wondered what his step-mother had in store for him, as their sexual activities were...

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'...

Nephew's Readjustment Pt. 13

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. * The next weekend, Cynthia called her nephew over in the afternoon. It was time to start preparing him for the next phase in her ever growing plans. She knew th...

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...

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...