Gay Chastity Chubby Stories

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The Show

by Luckylucy1 on Aug 18, 2017
Gay Male

I am a 49 year old bi female. My husband is 51 and also bi. About 10 year ago we were watching an adult movie and it had the girl/girl scene when my husband asked if I ever thought of doing that. I admitted I had. Then he asked if I would do it if I had the chance. I told him yes. Then it was my turn, I asked if he ever thought of doing it with a guy. He tol...

Progression Ch. 13: Unboxed

by klapperz on Jul 3, 2018
Gay Male

Nathan woke up and as usual, removed his t-shirt and briefs then made his way to the bathroom. On his knees, he waited for Kevin to arrive to prepare him for the day. Kevin was frequently late, and today was no exception. Nathan waited patiently for twenty minutes until Kevin finally opened the door and with his phone angled to take a picture. "Smile for y...

The Male Room

by WatchingAndWaiting on Aug 18, 2017
Gay Male

This is the story of my first time with a man. And my last time... So far. I was always curious, even when I was very young. Looking at men in magazines, especially if they were in revealing underwear and had big, well-defined bulges. I had messed around a little as a kid, but nothing more serious than 'you show me yours and I'll show you mine'. But as the y...

Cherry's Graduation Party

by CherryWood on Aug 30, 2017
Gay Male

I finish applying my lipstick and take one last look at myself in the mirror. I'm almost stunned at the reflection that stares back at me. After months of training and feminization I look like the perfect slutty fuck toy. I feel my little cock begin to get hard and strain against my chastity device as I look over my changed body. The strict exercise regimen...

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...

Jason's Trip to Mexico Ch. 06

by beefylatn on Sep 25, 2017
Gay Male

Jason and Carlos entered the cell to find Martinez struggling against the handcuffs that held his wrists over his head and attached to the frame of the cot. When Martinez saw them coming in the cell, he began to twist and plead in Spanish while Carlos explained what they were going to do to him. Jason got up on the cot, straddling Martinez facing towards the...

Hotel Room with View

by ddhavnfun on Aug 18, 2017
Gay Male

I spent a week at a training class in Miami last October. I love that area; it is so full of beautiful people living the highlife. Then there is me, a 59 year old chubby guy who does not fit in with them at all, but I still like to watch them. The classes were in the morning which left the afternoons free so I thought I would go lay on the beach to colorize...

Chubby Exhibitionist Let Him Watch

by ddhavnfun on Aug 18, 2017
Gay Male

Over the past few years I have become aware of my bi-sexual side and the pleasures of exhibitionism, especially for guys. My only outlet for this for a long time was the webcam; I am more than a little apprehensive about the "park bathroom". Besides they smell. Most guys I have cammed for love the show and I really enjoy having them in my room. I drive for m...

Enslaved by Myself Ch. 03

by Lausunaht on Sep 14, 2020
Gay Male

I was dreading what was about to happen. My master was going to hurt me badly to ensure I would never rebel. I knew this for certain because I would do exactly the same if the roles were reversed. I could only hope that my affection for myself was strong enough to limit the pain. He left me tied up alone for hours, I was thirsty as I didn't drink the whole n...

Progression Ch. 07: Decision

by klapperz on Mar 28, 2018
Gay Male

The next few days went pretty slow as Nathan counted the minutes until he could see Jack and Ryan again. It didn't help his frustration than Kevin, who was now sleeping in his bed, had quite a high sex drive. He was always demanding handjobs and blowjobs, which kept Nathan in a constant state of arousal. "I'm off to see the guy I told you about," said Natha...