Gay Chastity Chubby Stories

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Chubby Chaser Ch. 03

by drmweaver705 on Mar 3, 2020
Gay Male

All participants are over 18. ***** When Jeremy moved back to the big city, I was bereft. I would have followed him there but he said ass was cheap in the city. That was all I was to him for as long as we were together. There really was no "we"; I was just a receptacle for him to drop a load in. I couldn't blame Jeremy; he never promised me anything or led...

Cum Over

by sickoboy on Oct 22, 2019
Gay Male

Damian walked out into the sunlight and immediately felt the humidity in the air. The contrast from air conditioning to summer afternoon was like a rolling oven blast. Damian had thrown on a cotton Hawaiian shirt, and a pair of jean shorts, frayed at the cut offs. On his plump feet, he wore a pair of sandals. Today Damian was going commando. As the heat boun...

Becoming Daddy's Girl Ch. 01

by Sungmehetu on Mar 6, 2018
Gay Male

Editor's note: this story contains scenes of incest or incest content. ***** It might have been the death of my mother and my only sister in the car accident. It might have been that I tried to drink away the depression while I was hundreds of miles away from home at college. What I do know is two things. My father would be furious I had failed out, in jus...

A Weekend of Servitude

by HerLittlePiggy on Sep 14, 2017
Gay Male

Thank you Susurrus for the help editing this monster. ***** Richard Michael Quail, Rich to his family and friends, Mr. Quail to his associates and adversaries, sat quietly at the round high top table beside his sexy, buxom wife and sipped on a fine 18 year old single malt scotch. They were both well dressed: she in an expensive blue designer dress which d...

Eternal Oils

by Sigil4258 on Apr 3, 2018
Gay Male

My name is Levi. I'm 22 years old and I live alone in a tiny apartment. I keep to myself because it's easier. I've never really been with a guy before and I've definitely never been with a girl. As you can imagine, this has always been a source of frustration for me. Up until a few days ago, I'd been involved with a much older man over the internet. I met...

I Wanna Be Degraded Ch. 03

by 1077ad on Dec 25, 2019
Gay Male

Author's note: After a near-fatal hard-drive incident I was backing up some old files when I came across this. Somewhat to my surprise, this was abandoned in a nearly-finished state and then forgotten about. I mostly just had to spruce it up a little and give it an edit. I'm not sure that at this point, eight years (!) later, there's anyone looking for a con...

A Plan goes Awry

by HerLittlePiggy on May 29, 2018
Gay Male

I sat beside my wife in the loud, crowded bar. I'd been drinking for most of the day and I had a buzz but I was purposely acting much drunker than I was. My wife giggled nervously beside me as she talked to a young man she had met less than an hour before. He had an athletic build and an attractive face with dark ebony skin and a bright mischievous smile....

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...

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...

Descent into Depravity

by HerLittlePiggy on Sep 14, 2017
Gay Male

Sun streamed into my hotel room, waking me from my alcohol aided slumber. My head ached, my mouth was dry and my memory of the night before was spotty at best. I heard the shower in my room running and confusion set in. I had come to the conference alone and I had no idea who could be showering in my room. I recalled talking to a woman named Janice early at...