Gay Chastity Chubby Stories

271 results
Orientation
Length
Source
Infinite Scroll

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...

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...

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...

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...

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...

Best Friends Become Lovers Ch. 04

by UnderMyKilt on Nov 29, 2017
Gay Male

For those who haven't read them or have forgotten, you may have to read the previous stories to know how we got to this point. I hadn't intended for this to be series, but it turned out that way and this will be the last story under this series title. As we left off at the end of Chapter 3, Wayne and I had just fallen asleep after making love at a remote ca...

Billie's Sore Ass

by erectus123 on Jan 13, 2018
Gay Male

Billie's Sore Ass: Sexual Fraternity Hazing [Readers, be assured all events take place between men who are 18 and older. There are no minors or Appalachian miners depicted here. Most are college guys who range from 18 to 32 years old. A few older men do appear towards the end of the story to add a mature balance. All characters in this story are based on re...

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 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....

Do It for the Money

by vikkihawe000 on Sep 23, 2019
Gay Male

It was no secret things had been hard for Tori and Max and it was no secret the reason why. He had left his lucrative private equity job to start a restaurant. The loss of income (and 75% of their savings) had taken its toll. After several consecutive months of draining money, Tori went to work at a local coffeeshop to make some extra cash. She didn't love t...