Gay Gay Chastity Stories

22,838 results
Orientation
Length
Source
Infinite Scroll

Sissy Slave Toy

by slavegurl_veronica on Sep 16, 2017
Gay Male

Where it all began was at gym class in my freshman year of college. Gym was a course requirement for freshmen and I couldn't wait for it be over. I was skinny and weighed only about 130 pounds. I was not at all athletic and one of the smaller guys in the class. Fortunately though there was another guy named Alex, who like me, was also decidedly not jock mate...

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...

Smoking Hot Ch. 11

by Kumquatqueen on Sep 14, 2020
Gay Male

The books Adrian refers to are The Secret Diary of Adrian Mole age 13 ¾, and The Growing Pains of Adrian Mole, by Sue Townsend - brilliantly funny books summing up the early 1980s in Thatcher's Britain. _______________________________________________________ Sunday, I don't get up early, but I slink into my office as soon as I do wake up. Dan prises me ou...

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...

It's A Win

by Svenskaflicka on Aug 18, 2017
Gay Male

Father Jennings frowned as he looked at the young boy sitting on the other side of his desk. Eli was a skinny boy with a chiseled features in his face and hands. The pale face had hollowed-out-checks, and the huge, dark, beautiful eyes had dark rings under them. Eli looked nervously here and there, and kept biting his chewed-down fingernails. You didn't need...

Master Jakob and Seth Ch. 12

by and9993 on Sep 10, 2018
Gay Male

Chapter 12 - Night at the spa I felt the pressure from Master's message. I was looking forward to learning more about his magnificent body and how he likes it serviced, but it was clear from his tone that he expected me to put a lot of effort and thought in and not just guess. I feared that if he had to constantly correct me it would be annoying to him and...

Bobby

by skinnysailor on Jan 28, 2019
Gay Male

Every morning started the same. The harsh bell sounded and the lights came on. Roberto whimpered. It was a beautiful dream. They were in a grassy park. The sky was blue, the clouds fluffy white. He was wearing a pretty pink sundress. Damon was laying on his back wearing only a white dinner jacket. He was kneeling between Damon's knees. Damon's big black coc...

Army Biker Owned

by LthrBndBy on Jun 15, 2020
Gay Male

I've been owned by my Army Biker guy for about two weeks now. We've been playing for a little longer than that, you can go see our other encounters if you want to. Anyway, it's been the best two weeks of my existence. I no longer have to worry about getting to cum, I no longer have to think about anything but his needs. During the work day, I wear a chai...

The New Slave Ch. 05

by martin_x59 on Sep 14, 2017
Gay Male

I would like to start by saying I am new to writing so I hope you don't judge me too hard on my literary naivety. Nor am I experienced in Bondage or Master Slave relationships. This story is pure fantasy from my part and is about what I find erotic and stimulating. Please bear this in mind when reading the story. I hope you find it as stimulating reading as...

The Greatest Sin in the Book

by GGandG on Aug 30, 2017
Gay Male

I made the mistake of telling a my friend Mike that I had experimented with anal toys. Next thing I know I'm crouching my naked ass just above his thick, veiny, greased up pickle, wondering whether or not I could actually do it. It started about a month ago. My name is Patrick, Patty to my friends. Just your average slim, freckled, red headed Irish boy. St...