Gay Chastity Master Stories

3,422 results
Orientation
Length
Source
Infinite Scroll

Chase Becomes Chaste Ch. 01

by growing_interest on Aug 22, 2017
Gay Male

Chapter 1 - A Good Deed Is Its Own Reward Disclaimer: This is fantasy. Chapter synopsis: Chase, a narcissistic cheater and sadistic rapist, has a life-changing run-in with a man who has a penchant for mind control, fitting punishments, and long-term chastity. A smartly-dressed, middle-aged woman walked into my office. She seemed familiar, although I did...

Master Jakob and Seth Ch. 14

by and9993 on Sep 18, 2018
Gay Male

Chapter 14 - The anatomy of a blow job Training Day 8 - Saturday I woke up to find Master sitting up in bed and had an immediate panic attack thinking that I overslept again and that he was waiting for me. I checked the clock and found that was not the case. "Good morning Seth," he said. "I want to start the day off with a talking blow job. As you know I...

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...

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....

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...

How I Found a Keyholder Ch. 03

by 1077ad on May 12, 2020
Gay Male

3.a: The treadmill Wednesday had come around again. I had gotten a message from Sir to be at his place for one p.m. and I was achingly horny. Besides the fact that I had been locked for a month now, far longer than I ever had been before, I was still feeling the residual excitement from shooting that video in the parking garage on the weekend. So, after doi...

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...

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....