Gay Chastity Boy Stories

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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...

Temporarily Dickless

by AssWhisperer on Sep 14, 2017
Gay Male

[Warning: This is a very sexually dark story. Fisting, watersports, medplay, implied body modification, chastity. My thanks to Kenji De Sade for his encouraging me to write this story after a series of conversations about chastity.] How had I come to be here? I wondered as I floated in orgasmic bliss. It had started with my impulsively writing a guy on...

Top Becomes a Daddy Bear's Boy Pt. 02

by DaddyBearChaser on Jul 6, 2020
Gay Male

Mike woke up in the morning and gave his new boy a tight squeeze, nuzzling his beard and nose into his boy's smooth neck. "Boy it's morning, time for you to get up and take care of my needs," he said softly in his deep grizzly voice. I woke up being squeezed and spoken to, not knowing what was going on I tried to get up. I felt big arms wrapped around me an...

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...

A Soldier's Journey Ch. 01

by FenFenScreeScree on Apr 13, 2020
Gay Male

(This story is based on true events. Details have been changed to protect the identity of the characters) Sometimes, I worry if I've gotten too far in over my head... My journey through chastity play is not an easy one, and it's a path that many of my sexual peers would never have had the fortitude to walk down. Allow me to preface this story with what y...

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...

Confessions of a Chastity Slave

by deviator on Aug 31, 2017
Gay Male

It's hard to believe it all started with some talk on a chat room. I was in college then, and always straight in real life, although not very successful with the ladies. But my dirty little secret was that I liked to go online and indulge my fantasy: being enslaved, feminized, and kept in chastity by a man. At first, I'd wander through chat rooms and find a...

Power Trip Ch. 04

by Wally_West on Sep 18, 2017
Gay Male

Reader Warning: Over the course of several chapters this story will contain cuckoldry, forced-bi, male chastity, humiliation, and other female domination themes. These kinks are not for everyone; if you do not enjoy FemDom themes you will not enjoy this story. * A week had passed since Colin had sucked his first cock in the glory hole. Veronica had held hi...

Bathhouse Chastity Bitch

by Cumpup39 on Feb 11, 2019
Gay Male

I'm a married man in my early 40's, I'm 5' 7" in good shape and have a great wife and two kids. I also have a secret, I'm an absolute cum whore! I love everything about being used by men! I love being manhandled, degraded, covered in cum, piss and spit. My favorite kink is being sexually humiliated in public, in front of strangers. My wife would never beli...