Gay Fisting Chastity Stories

743 results
Orientation
Length
Source
Infinite Scroll

Blink: Four

by KenjiDeSade on Aug 18, 2017
Gay Male

The following story is a fictional account. The characters are entirely unreal and so are their situations. Thus no direct attention was paid to probability or safety for the characters. Such practices should not transfer over to real life situations. Practice safe, sane and consensual sex. For your own damn good. If you have problems or issues with queer po...

The Hanky Code Pt. 02

by His_fag_wife on Sep 14, 2017
Gay Male

The Hanky Code Chapter 2 - The agreement pt 1 I followed him down a black painted and dimly lit hallway which lead to one large steel door that seemed rather imposing. A nameplate on the door read, 'Master S.' I gulped standing there. Maybe saying yes was not the best of ideas. Though I was having second thoughts they evaporated quickly. Who was I trying...

One Sub Stud Ch. 01

by tazemebro on Sep 14, 2017
Gay Male

AUTHOR'S NOTE: This story is a continuation of the series about Chris Donaldson and Justin Corvino, who were roommates during their sophomore year of college. While living together, Justin turned Chris into his personal cocksucker and submissive - a fate Chris initially resisted, but eventually came to love. Along the way, Chris had other admirers. He gave u...

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...

Tramp Steaming Ch. 02: Christophe

by sr71plt on Nov 27, 2017
Gay Male

I pulled a pair of low-rise shorts and a sports shirt out of the closet, put them on, leaving the sports shirt open and not tucked into the shorts, and padded down to the hotel reception desk to start the process of reporting I'd been ripped off, was temporarily destitute, and needed help to start the process of canceling cards and replenishing my funds. I w...

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'...