Gay Chastity School Stories

7,745 results
Orientation
Length
Source
Infinite Scroll

A Chastity Story Pt. 01

by Fromthetap on Oct 15, 2017
Gay Male

I arrived at the street and pulled up just after the entrance to the cul-de-sac he lived on. Getting out of the car, I pulled the zip on my jacket up to the top to hide the collar I was wearing. It was 2:30am but even so a car drove past as I walked down the street, pretending to cough so that I could cover my neck with my arm, not wanting the headlights to...

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...

Chase's Dive into Chastity Ch. 01

by Ohshidwhatup on May 15, 2019
Gay Male

I awoke to the harsh wailing of my morning alarm. With groggy annoyance I rolled over and switched it off. I had the urge to just cover my head with my pillow and go back to sleep but something kept nagging at the back of my mind as i lay there eyes closed. Whatever. Just ten more minutes. Have you ever had that feeling of worry even when you are asleep? T...

Trained as a Urinal

by Cumpup39 on Feb 11, 2019
Gay Male

Sir is a beautiful man! He is in his mid 40's, 6' tall and has a beautiful hard body. His short dark hair and blue eyes make me weak. He has a perfect cock, just under 7" but thick and I can't keep my mouth off of it! I was his regular cocksucker for a while, coming over whenever he needed to get off. Sir works hard and doesn't have time to date, so I got a...

A Night at the Movie turned me Gay

by jamtby on Oct 6, 2020
Gay Male

During my senior year in college I was a busy, serious student. I had a girl friend and we enjoyed time together and an active sex life. All in all I was a typical 20 year old male. Then an unexpected movie changed everything. My girl was out of town on a field trip for a psychology course she was taking. It was Friday night and I was horny. I made the dec...

Progression Ch. 12: Duties

by klapperz on Jun 18, 2018
Gay Male

The next morning Nathan slept in, glad he didn't have to get up for work as usual. He lay in bed, wondering what he would do during the day. He thought about the tasks Kevin might make him perform, and if he would get to taste his cum again. At 9.15am Kevin entered the bedroom, saying "Excuse me? Is there any reason you are late?" "Late? Kevin, I got fired...

Bathhouse Chastity Bitch

by Cumpup39 on Feb 11, 2019
Gay Male

I'm a married man in my early 40's, I'm 5' 7" in good shape and have a great wife and two kids. I also have a secret, I'm an absolute cum whore! I love everything about being used by men! I love being manhandled, degraded, covered in cum, piss and spit. My favorite kink is being sexually humiliated in public, in front of strangers. My wife would never beli...

A Soldier's Journey Ch. 02

by FenFenScreeScree on Apr 13, 2020
Gay Male

When I woke up that Saturday morning, I made a bowl of cereal and opened up Grindr. The moment I did I was yet again bombarded with messages and taps from several different guys who were clearly all soldiers. Half of the guys that messaged me sent dick pics (of course), and the other half acted like they just wanted to chat. Yeah right. Well, I figured I'd...

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...

No Backup Plan Ch. 01: Sick Day

by klapperz on Aug 22, 2018
Gay Male

Max made a final fake cough as he phoned in sick for the day. It was never his plan to do this so soon after taking the job, but the excitement was too intense for him to wait any longer. Lying in bed, he felt his cock throb. But it wasn't time yet. Footsteps, loud bangs and chatter continued throughout the walls as his housemates rushed to get ready for wo...