Gay Chastity Boy Stories

10,280 results
Orientation
Length
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Infinite Scroll

Chase's Dive into Chastity Ch. 01

by Ohshidwhatup on May 15, 2019
Gay Male

I awoke to the harsh wailing of my morning alarm. With groggy annoyance I rolled over and switched it off. I had the urge to just cover my head with my pillow and go back to sleep but something kept nagging at the back of my mind as i lay there eyes closed. Whatever. Just ten more minutes. Have you ever had that feeling of worry even when you are asleep? T...

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...

Chase Becomes Chaste Ch. 04

by growing_interest on Aug 22, 2017
Gay Male

Chapter 4: Dogged Determination Synopsis: With his powers seemingly exhausted, our narrator recruits help to keep Chase in his place. **************** I awoke with a throbbing headache. I felt hungover. The sun shining in through the room's many windows strained my eyes. As much as I just wanted to stay in bed, eventually I pulled myself up so that I coul...

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...

The Trio Ch. 01

by Fafantasiz3 on Feb 25, 2019
Gay Male

When The Man returned from work the boys were at play, David thrusting deeply and powerfully into Sasha's perfect round bubble butt, enjoying the sight of his lover's sore ass. He had been whipping it again, and he could see the blonde 20-something who was currently arched and getting thoroughly fucked by his other 20-something lover had been crying, and moa...

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'...

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...

The Master and Slaves Playtime

by LthrBndBy on Jun 9, 2020
Gay Male

As in every single one of my stories, all characters are over 18, and fully consenting adults. This story is purely fictional on all accounts. Enjoy. ————————————————————- Here I am, in all my "glory" so to speak, kneeling on the floor of the closet in our bedroom. My arms stretched out to either side to the walls, my mitts clipped to the rings discreetly...

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...

Influencer to Sex Slave Ch. 02

by dreamymark9 on May 15, 2019
Gay Male

Author's note: This is erotic fantasy and completely fictional. The main character, Jack, is a fictional, generic social media star / influencer, and is not a real person. As always, would love to get feedback in comments and messages. ***** Jack wakes up naked in bed, being spooned by his master, in his Airbnb in LA. Recent events still kind of feel like...