Gay Detention Stories

72 results
Orientation
Length
Source
Infinite Scroll

Prison School Ch. 23

by o2byoung on Sep 14, 2017
Gay Male

Chapter 23 – W4 Monday evening (Just to catch you up – at the very end of Chapter 22, Luke had received this letter) "Mike," Luke said, "I received a very disturbing letter today from Sylvia." "Sylvia? Who is Sylvia?" "She is—was my girlfriend. Mike," Luke sobbed, "I don't know what I should do. She wants to make amends, here, just read it!" Luke handed...

Sedley, Schoolmaster

by justincbenedict on Aug 18, 2017
Gay Male

SEDLEY, SCHOOLMASTER "Who's that fellow in the picture" Submissive Stuart's Master Fenton asked him one day while Stu was licking Fenton's boots in his office. Stuart looked up and noticed Fenton looking at the old painting of Stu's bewigged ancestor. "Oh, that's my great-great-great-great maternal grandfather, Sedley Codrington, Master Fenton. I don't...

Becoming George's Bitch

by TheDarkCloud on Aug 18, 2017
Gay Male

DISCLAIMER: Although this story is under the genre Gay Male please be aware that it also encompasses others. There are BDSM elements to the story and also Fetish elements and if these are likely to be offensive please be aware they are there before reading. Really if there was a genre for 'humiliation' it would be in it. This features the characters Marcia...

Peter the Queer Pt. 01

by ThisGun4Hire on Feb 6, 2018
Gay Male

PART I: BAD BOYS GET PUNISHED "Close the door behind you," he said. He looked like he could have been a fireman in his younger days. That's because he was large with a big body frame. Perhaps he had been in-shape at one point but now he was a decidedly heavyset man. Because firemen, when they reach a certain age and become fire chiefs and sit behind desks i...

Prison School Ch. 21

by o2byoung on Sep 14, 2017
Gay Male

Authors note: This is the 21st chapter of a multi chapter story. If you have not read the first 20 Chapters, I highly recommend you go back and start from the beginning, otherwise you will be completely lost! Chapter 21 – W3 Friday Morning The bus left the main building at 7:00 AM sharp with 22 trainers and trainees on their way to the training site....

Spring Break Oil Wrestling Contest

by WorldOfSize on Jun 8, 2020
Gay Male

Kevin and Todd, best buds through elementary, high school, and their Freshman year of college, were in Orlando for their very first spring break. Everything was going just how they'd imagined. Chicks in skimpy bikinis were everywhere, alcohol was plentiful, everybody was available, DTF, and skin was in the game. They'd hit the gym hard in preparation for sh...

Prom Night

by SWhite1982 on Sep 14, 2017
Gay Male

So much for a senior prom, I mused, watching the flicker of the candle flames on the center piece. They wriggled in the dimly lit ballroom of the Rose Hotel, stretching only to almost drown in the liquid wax only to stretch again. It was supposed to be a platinum night. I had a date with a chick named Kara that had a killer body and a bottle of vodka my ol...

Friendly Welcome to Gleeson Street

by DavidMcAllister on Aug 30, 2017
Gay Male

Chestnut Falls 1953 It was a Friday morning and already I was on my knees blowing Jordan Powers in the hallway of Madison High School. The final bell for third period had just rung so the hallway was empty, and with the students and teachers busy with the morning's lesson, Jordan and I took advantage of the situation and unleashed our primal urges. Jordan...

Watching Him Back Ch. 02

by Acerbicscribbler on Sep 19, 2017
Gay Male

It's Friday and I'm fidgety and in a bad mood. Part of it may be that I haven't had a chance to confirm with Crispin. Saving him from bullying is mostly keeping Jay and them distracted from that crowd, which means a lot of clowning and talking loudly about random shit whenever Crispin or one of his friends walk by. I can't get close to him, but I have this h...

Barriers Ch. 04

by ThingsYouWouldBelieve on Aug 18, 2017
Gay Male

Authors Notes: I'm back after 5 years and i've decided to revamp this story and see it though. If you've read this before please go back and read the first few chapters as i've changed a few important plot points, namely the one about Houston. If you're new welcome, i hope you're enjoying my work. * The doorbell rang about ten times before I realized the...