Gay Chastity Stories

271 results
Orientation
Length
Source
Infinite Scroll

What Do You Want Me to Do?

by Cyanlot on Oct 15, 2017
Gay Male

Dear Ted, I hope you're having a nice weekend with Wendy. No ... I don't, really. I just said that to sound nice. But I'm not feeling nice. So why should I try. Honestly, I don't know what more you want from me. If you wanted to end the whole thing because you thought it was wrong or because it threatened your sense of masculinity, at least I'd understan...

Versatility on the Court

by puzziboi on Mar 18, 2020
Gay Male

Matt Wenzel was awakened by the sound of his live-in girlfriend rustling through her drawer. "Babe," he yawned. "Just turn on the light." He rolled back over and pulled the covers over his head. He desperately wanted a couple more hours of sleep. The 32 year-old corporate budget analyst had stayed up later than he'd intended last night fucking the petite chi...

Rory and Sebastian

by sebastiando on Sep 14, 2017
Gay Male

- Everyone in this story is over the age of eighteen at the time it begins - I wish I could say it was love at first sight. But it wasn't. And it wasn't one of those instant hatreds either. The kind where a weird tingle shoots straight to your balls and you want to pound the fuck out of the person -- whether it's with your fist or your dick, you don't quite...

Good Lovin' Cum Again

by Ciceri on Aug 17, 2017
Gay Male

As so many of you know, giving up a fetish or secret desire is not easy. As a straight man in a committed relationship, I was, for the most part, sexually content. However, my mind wandered to a time when I had my needs met by an older gentleman who administered punishment and saw to my sexual release. Walking into his house was a feeling unlike any other....

Buster and Me Ch. 02

by seattledon on Aug 18, 2017
Gay Male

Last month Master surprised me by saying that we were going on a trip for the weekend. It had been a year since I had moved in with Master to care for His house, His dog, and to serve as His dog as well. During that year, the only time I left the house was when walking Buster, His dog, and going with Master and Buster to His friend's place for training. I am...

Influencer to Sex Slave Ch. 05

by dreamymark9 on Jul 30, 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. Today was Jack's first day as a sex slave when his master was at work, and it was pretty eventful. He got a ton of embarras...

Master Jakob and Seth Ch. 13

by and9993 on Sep 11, 2018
Gay Male

Chapter 13 - Day at the park Training Day 7 - Friday I woke up the next to the vibration of my alarm at 7:00. I was extremely excited to get a break from training. I could see Master sleeping peacefully in his bed. I began my usual morning routine. The first thing I did was shower. I took special care to clean the area around my penis and chastity device....

Collateral Ch. 08

by laurasfox on Jun 5, 2018
Gay Male

Jake flipped nervously through the magazine left on the nightstand. It was all in German, and he could not understand squat. He sighed and buried his head in the crook of his elbows. Then he stretched, enjoying the fluffiness of the sheets. "Nice view," he heard Klaus calling from behind and straightened up immediately. "Who's childish now?" he went for a...

Rubber Puppy

by RbbrAndy on Sep 14, 2017
Gay Male

After a busy day at work I eventually left the office later than normal, I headed to the local train station to catch a train home. Things were clearly not going in my favour as I soon discovered that all trains had either been delayed or cancelled due to an earlier incident at another station nearby. I decided that instead of waiting for a train that I woul...

Snowball Effect

by sr71plt on Aug 18, 2017
Gay Male

I couldn't resist Michael Dabney's proposition in the Checkers Lounge at the LA Hilton Checkers hotel during the Entertainment Industry Advertisers' Association convention—well either of his propositions, really. I'd never done it with a black man before, and that had become somewhat of a special fantasy of mine. I was attending the EIAA convention, because...