Gay Chastity Anal Stories

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Fixing the straights

by cdbaby on Dec 28, 2016
Gay

You wake up and prepare for your day, unaware that this would be the last day you would be considered straight. You shower as you did every morning and felt the water's warm touch as it cascaded over your skin. You could stay here forever if you could. But you need to start your day and the hot water would run out before long. You wash your hair, then the re...

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Nephew's Readjustment Pt. 14

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 week began with a morning session with his new plastic lover. While the bathroom made things easiest if he was willing to work, morning wood wasn'...

Master Jakob and Seth Ch. 10

by and9993 on Aug 22, 2018
Gay Male

Chapter 10 - Dinner I brushed my teeth and got dressed, then took off my collar and put it in my pocket. It felt strange having clothes on over my plug and cage but I was eager to see where Master would take me. We got in the car and drove to a nearby restaurant. It turns out Master wanted just a night out with the two of us. We got seated and he began by...

The Making of a Master

by Littlepoppyhole on Oct 6, 2020
Gay Male

David lay on the dishevelled bed exhausted and still sweating after his recent sexual encounter with a man called Raymond. His hole was leaking semen onto the bed sheets. The sheets also gave off the aroma of anal mucus. This did not perturb David as he was deep in thought about the man he had served. He thought there was room for improvement in his sexual i...

How I Found a Keyholder Ch. 03

by 1077ad on May 12, 2020
Gay Male

3.a: The treadmill Wednesday had come around again. I had gotten a message from Sir to be at his place for one p.m. and I was achingly horny. Besides the fact that I had been locked for a month now, far longer than I ever had been before, I was still feeling the residual excitement from shooting that video in the parking garage on the weekend. So, after doi...

On No He Didn't

by felicia_rene on Sep 21, 2020
Gay Male

Description This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy safely. Rick a tall well-built handsome entertainer catches the eye of his boss as he works at his night club. The man's lust consumes him and he conspires to twist him and make Rick his bottom. Despite the fact that Rick insists that he was a...

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...

From Gay Husband to Slave Pt. 01

by assguzzler on Apr 3, 2019
Gay Male

My husband Winston and I were married when I was twenty two and he was thirty. I told him of my submissive fantasies and he role-played with me some at the beginning of our marriage but for the most part he showed little interest in D&S or Domination. We had a good marriage but we often fought as we both tried to dominate the other when it came to who would...

The Greatest Sin in the Book

by GGandG on Aug 30, 2017
Gay Male

I made the mistake of telling a my friend Mike that I had experimented with anal toys. Next thing I know I'm crouching my naked ass just above his thick, veiny, greased up pickle, wondering whether or not I could actually do it. It started about a month ago. My name is Patrick, Patty to my friends. Just your average slim, freckled, red headed Irish boy. St...