Gay Chastity Shrinking Stories

741 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 SmutMD.com

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...

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...

Nephew's Readjustment Pt. 03

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, mind fucking and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. Comments, ideas and feedback are welcomed, and remind me to keep writing! *** She set everything in motion over the next two days. Her excuse about...

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...

Progression Ch. 14: Befriended

by klapperz on Jul 3, 2018
Gay Male

Nathan woke up earlier than usual the next morning after a night of arousing dreams. He was eager to start work and see what the guys had in store for him. After his daily inspection with Kevin, they both made their way to Ryan and Jacks house. Once they arrived, Nathan stripped and made his way to the basement to begin his daily show. When he reached the...

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...

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...

Discovered by a Black Guy

by chastity_sissy on Sep 14, 2017
Gay Male

I should preface this story by saying I've never identified myself as homosexual, but sometimes after being locked up in chastity for a long time combined with crossdressing, I must admit to some fantasies involving other men. I never expected anything to ever actually happen, and it's my own fault really. I had been paying a beautiful, very sexually fetis...

Progression Ch. 02: Regret

by klapperz on Mar 6, 2018
Gay Male

The next few weeks Nathan went back to normal. Wake up, Work, Wank, Sleep. Almost forgetting about his encounter with Ryan. It wasn't until a month later that his urges to lock up his cock would come back. He started to remember Nathan and his offer. "He did say I didn't have to show my face" he thought to himself trying to ease his shyness. He pulled open...