Gay School Caning Stories

7,585 results
Orientation
Length
Source
Infinite Scroll

It's Too Cliché...Right? Ch. 01

by musicfreak on Sep 13, 2017
Gay Male

Note: This story doesn't revolve solely around sex, so if a quick hot sex scene is what you're looking for, this story isn't for you. A/N: Hi guys, I'm back with a new story for you. I'm really happy with how this story turned out and I hope you guys enjoy it. A huge shoutout to Y0rite for volunteering her time to help me as my editor. Her insight has helpe...

Shoelaces Ch. 01

by kaysea on Aug 17, 2017
Gay Male

This is my first story submission, so please leave lots of feedback but please play nice. There's kind of a innocent sex scene, but no hardcore stuff. I'm working on that for later chapters. So if you don't want to wait, skip this, or at least don't flame me for it. These characters and stories are mine. Any resemblance to actual people or events is incide...

Bio of a Bully

by ozeboi69 on Sep 14, 2017
Gay Male

I am so fuckin’ hot. I mean it, no kidding. It’s not vanity or nothin’ like that. It’s true. Plain and simple. I am fuckin’ a-grade hot. It’s like at school, everyone wants a piece of me, you know. The chicks giggle and gawk when I walk by and all the blokes – they all wanna be just like me. Even some of the teachers - no bullshit! It’s great being lik...

Fuck My Teacher

by gayandhorny4u on Jul 24, 2018
Gay Male

On the morning of the first day of his senior year, Nick awoke in a pissed off mood. It was 6:30 a.m. and it was way too early for him. However, after realizing it was his senior year and he would soon be out of his hell-hole of a high school, his mood lifted. Nick slowly got himself out of bed, took off his Tommy Hilfiger boxer-briefs and hopped into the sh...

The School's Fuck Toy

by Nasties on Sep 14, 2020
Gay Male

***This is 'one of them schools' where everyone is 18 years or older.*** I am an 18-year-old boy and I attend a catholic school. It is one of the best schools in the state. Most local political leaders, successful businessmen and other famous people actually attended this school. It is a well-funded school that does tend to focus the most on its sports faci...

David Gill Ch. 01

by StackShotBilly on Sep 14, 2017
Gay Male

I suppose I should start at the beginning of my story. My name is David Gill, I'm eighteen, and a senior in high school. At five feet, ten inches and about 150 pounds, I'm not a big guy, but it's not like I'm a wuss. I'm striker on the soccer team at my school and I did karate for about five years, I was pretty good at it too, so I know how to handle myself....

Alice, My Uncle, & Me Ch. 04e

by John Hill on Sep 14, 2017
Gay Male

This continues the account of the five days and nights that studly 18 year old Mikey spends together with Mike, the 24-year old uncle he idolizes, and Mike's fascinating and beautiful 22-year old fiancée Alice. The beginning of their story is told in "Cross-Country with My Uncle," and continued by "Alice, My Uncle, and Me," day 1 and day 2, and Day 3, parts...

Old School, New Lessons

by LeathermanCraig on Aug 18, 2017
Gay Male

My stomach was churning and a headache was starting to form just above my eyes. Nearly 20 years later, that building still gave me fits of trepidation: Bradford James High School; home of the Fighting Navajos. Of course, here's a tip for the people that name schools and figure out the mascot names: think like a high school kid. Going to school at Bradford...

Best Friends Of The Same Sex

by Samuelx on Aug 18, 2017
Gay Male

They say that opposites attract. I think that this saying is true and not just in romantic situations. My name is Ronald Brown and I have a story to share with you. It's about me and somebody who kind of, sort of matters to me a lot. First and foremost I have to let you know something. I'm a guy who gets wild and does all manners of things so if you're faint...

Two Southern Gentlemen Ch. 15

by htausten on May 11, 2020
Gay Male

Content/trigger warning: This series contains bullying, homophobic language, and non-consensual sexual acts, but they are integral to the plot and character development so please take them in context. JESSE It's the first day back at school, and I never knew that a summer could crawl by so slowly. Despite myself I went back to the cove whenever I could fo...