Gay Chastity Chubby Stories

828 results
Orientation
Length
Source
Infinite Scroll

Nephew's Readjustment Pt. 02

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, chastity, mind fucking and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. Comments are always really appreciated. ***** Nicholas' next day was filled with confusion. He had difficulty focusing on his classes beca...

Time to Pay the Rent

by blueboysf on Apr 17, 2019
Gay Male

I live in South Florida. Moved to a small apartment that was close to work. It is a small apt. building, two stories and ten apts. small one bedrooms. The owner manager lives in the building. He is an older male over 60 years old, not too tall, I stand 5-9 and he is maybe a couple inches taller. On the chubby side and you can tell that at some time he was ve...

Piggy's Corn Hole

by bi3inchpig on Jun 9, 2020
Gay Male

Harry had never had a massage. How could he even consider putting some poor masseur through the torture of massaging his fat body? A guy he chatted with online assured him, "They are professionals; they work with all body types. Your fears are irrational. Just book it and let it happen. You'll be glad you did." His back was killing him. He had put on a bit...

Chase Becomes Chaste Ch. 02

by growing_interest on Aug 22, 2017
Gay Male

Chapter synopsis: While Chase loses his property and his dignity, our narrator takes possession of his new condo and his new boy. *********** The movers arrived bright and early. I had just awoken from a pleasant sleep, dreaming all night of how I could punish Chase next. I felt refreshed and empowered once more. It was that same sense of certainty that ga...

Jim's Hotel Room

by yuyuassen on Aug 18, 2017
Gay Male

This is a contuniation from Jim's Police Ride, 18 Jim keeps finding new and exciting way to occupy his time! Jim was taken aback by the men in the room. He didn't know what to make of it! Corey walked in the room and said "Boys, this here is Jim. He's been having a few hard days." One of the men yelled out "I bet he has!" Corey laughed, "But let me tel...

From Straight to Gay

by jsmjsm on Sep 14, 2017
Gay Male

* I dedicated this story Abbie my best friend * Thanks to maidenrose for editing I have try to keep in line the best i could with the reality sorry if sometimes is not making sense but that's life!! ***** I cannot believe what a journey I am about to write. I define myself now as gay or bisexual because I don't know what the future may hold but let me st...

First Tape

by JimBob44 on Sep 25, 2017
Gay Male

*Author's Notes: Any and all persons engaging in any sexual activities are at least eighteen years of age. Disclaimers: Yes I need an editor. No I do not want an editor. If that bothers you, quit reading. Yes it jumps around too much, yes there's too many people keep track of, yes it's too long, yeas it's too short, yes it's in the wrong category, yet its s...

The Occasional Cocksucker

by SensualIowaDom on Jul 31, 2019
Gay Male

I used to say I was a straight guy who just happens to enjoy cock now and then, but now I'm proud to admit my bisexuality. Well, not openly. Sigh. I'm 42 years old, divorced, and I have a girlfriend who has no idea that from time to time I do what I'm about to tell you. A few days ago I was on a business errand and decided to combine it with my lunch hour...

Jim's Camping Trip

by yuyuassen on Aug 30, 2017
Gay Male

Two months after his 18th Birthday, As Jim laid in bed, his leg were very tired. Jim had just finished his eagle scouts project, building a bridge in the creek. Sounds stupid right? But it worked, so now he was done with scouts forever! Wait, damn, he just said he would help his scoutmaster out with a camping trip! "Fuck, fuck fuck..." he thought as he undr...

The Trio Ch. 01

by Fafantasiz3 on Feb 25, 2019
Gay Male

When The Man returned from work the boys were at play, David thrusting deeply and powerfully into Sasha's perfect round bubble butt, enjoying the sight of his lover's sore ass. He had been whipping it again, and he could see the blonde 20-something who was currently arched and getting thoroughly fucked by his other 20-something lover had been crying, and moa...