Gay Chastity Chubby Stories

828 results
Orientation
Length
Source
Infinite Scroll

Bobby's First Suit

by timmywells on Aug 18, 2017
Gay Male

"I thought it would be a good idea to buy Bobby a suit," Gladys Bradley told the little Italian tailor whose shop was down the road from their apartment. "Not only for the dance, but with Bobby going to college in a couple of months he'll probably need a suit for other things." "A college boy now huh?" Tony Caruso asked as he rubbed the dense 5 o'clock shad...

Blue Goes Bi

by FriendlyStranger on Aug 18, 2017
Gay Male

This took place in the early 1970's- a few years after I was discharged from the army, I worked mainly on harvest crews in those years, hard work and long hours. We would start down south in early summer and follow the harvest north until fall. I would then go back to my home in the hills with enough cash to last until the next year. I was in my early 20's,...

Rex's Horny Halloween Pt. 01

by TeamCravings on Nov 27, 2018
Gay Male

(This new story carries on from, The Wonderful World of Rex) *** Lorna snapped one more photo as the train doors opened. The old frumpy, very tipsy businessman's balding head slid up and down Rex's cock with a gurgling sound. It almost sounded like choking really to Lorna's mind as the buzz of the very large crowd began to fill the carriage. Lorna made a q...

Jack & Junebug Go To Prison Ch. 01

by KenUnknown on Aug 18, 2017
Gay Male

This story is a fictional story. This story takes place in prison. Jack was arrested for arm robbery and sentenced to 2-Years and Half in Prison. Jack had a good lawyer, and that's why he got less time. With good behavior, Jack could get out with in 21 months. Jack needed help and protection. So enters Junebug! Junebug is a career criminal. You name it, he...

Hell slave

by Pantherking on Mar 4, 2019
Gay

You are a slave in hell. A lowly toy for Master Asmodeus to use. Your pathetic cock locked forever in Chastity, and constantly edged. You'll never know release. You'll live your eternal existence serving your master, and loving every second. Right now we will decide what species of slave you are.What's next? Rat What's next? Rat...

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College Boys Curse Ch. 01

by Mysteryman66 on Nov 19, 2018
Gay Male

Erik and Javi had been best buds since they were in their early teens, throughout high school and now into college. They were excited about starting college together and the fact they managed to score being roommates. 2 best bros rooming together through college, they were sure it'd be a blast start to finish. Non-stop partying, drinking, smoking, and bangin...

Influencer to Sex Slave Ch. 02

by dreamymark9 on May 15, 2019
Gay Male

Author's note: This is erotic fantasy and completely fictional. The main character, Jack, is a fictional, generic social media star / influencer, and is not a real person. As always, would love to get feedback in comments and messages. ***** Jack wakes up naked in bed, being spooned by his master, in his Airbnb in LA. Recent events still kind of feel like...

Progression Ch. 11: Goodbye

by klapperz on Jun 18, 2018
Gay Male

"Welcome home," said Kevin as Nathan pulled the car into the driveway of his home. "It feels like I've been away longer than a week," said Nathan. Nathan opened the door and let Kevin into the house. "Welcome back, how was the holiday?" said Jeff calling out from the living room. "Oh yeah, I told Jeff we went away for a week holiday. Just play along. Or...

Oliver's Balls Ch. 03

by newbitime on Sep 15, 2017
Gay Male

It had been just over a year since Oliver had taken control over my life. And control it he did. I went from being a promising young salesman, to an assistant, who handled all of my boss' accounts, and also served as his cock slave. Oliver had moved into a much larger penthouse apartment, while I was struggling to feed myself on a weekly basis. Not only was...

Turning Myself Gay Pt. 03

by bart_allen on May 29, 2018
Gay Male

To my mutual humiliation and arousal, the next morning at work, Marie could instantly tell. Truth was, I could see why: Nathan had fucked me three god damn times, and I my ass was sore as hell. Sure, he'd been tender as well at times, but one look at me and she knew. She just rolled her eyes at me, causing me to blush. She wanted to know what he looked like,...