Gay Chastity Cage Milking Stories

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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...

Converted to Gay

by bart_allen on Sep 14, 2017
Gay Male

This story is partly inspired by messages from fans, with slight adjustments. Thank you for reading. ***** I wanted to share with you one of my current projects. A twenty five year old male by the name of Eric. Nothing too special in the looks department, but not too shabby either. He was neither heavy or slim, perhaps a slight softness to him. His eyes we...

Progression Ch. 04: A Real Fitting

by klapperz on Mar 6, 2018
Gay Male

Nathan hung out with Jeff and his other flatmates for the day. He had been so focused on Ryan and Jack that it was nice to have a break and be normal for the day. They went to the pub for lunch and then watched some films. Before he knew it, the day was over and everyone was heading for bed. The next morning Nathan woke up for work. He panicked, remembering...

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. 03: The Show

by klapperz on Mar 6, 2018
Gay Male

Nathan turned and looked at his clock. It was barely 3am and he was just lying there looking at the ceiling. No matter how hard he tried he couldn't stop thinking about his session with Ryan and Jack. He put his hands under the blanket to feel his cocks prison and attempt to get some relief, but it was useless. When he tried to play with himself his cock jus...

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. 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...

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. 01: Finally

by klapperz on Oct 15, 2017
Gay Male

Nathan paced around the shop for a few minutes while building up the courage to purchase the chastity device. This was his first time inside a sex shop, and he was very uncomfortable. He saw shelves full of different toys, each one exiting his mind with sexual thoughts. He noticed the device he wanted was behind the counter, but in order to seem less awkward...

Liam's Submission Tested Pt. 05

by PupTracer on Oct 5, 2020
Gay Male

Marcus brought entirely too much food to be defined as a "snack". He had piled on peanut butter and jelly sandwiches, strawberries, cookies, almonds, even slices of cake. When he attempted to precariously juggle it all on one flimsy paper plate, it didn't end well for him. As he lowered the plate to me his rather large boot tapped the edge of the bedframe an...