Gay School Caning Stories

7,585 results
Orientation
Length
Source
Infinite Scroll

Ben is Bitten by the Big Apple Ch. 03

by verdunsears on Apr 21, 2020
Gay Male

It's New York in 1974 and twenty-four-year old Ben is spending the weekend with Robert and Ian, two vacationing leather tops from England. After starting out by letting him suck their dicks, tying him up and fucking him, they'd moved on and begun loaning him out to others. All three had been invited to a sex party, due to start in the early hours of Sunday....

The Making of a Gay Disciplinarian

by JASONSHOMOEROTICA on Aug 18, 2017
Gay Male

My name is Kevin Pettifer. I am just twenty-five years old. I am a regular sailor in the Royal Navy, which I joined as a cadet when I was eighteen years old and in which I now hold the non-commissioned rank of Petty Officer: Petty Officer Pettifer! I have just been promoted to this rank and posted to what seems like my dream job: chief physical education ins...

Chris Donaldson Ch. 04

by tazemebro on Sep 15, 2017
Gay Male

Chapters 1, 2 and 3 tell the story of Chris and Justin, roommates in their sophomore year in college. Justin is an athletic frat boy with lots of animal charm, and quickly turns the sexually inexperienced Chris into his live-in submissive. Justin's volatile and violent personality, however, eventually frighten Chris into asking his Resident Advisor for new q...

Gentlemen's Club Ch. 03

by Ywashere on Sep 14, 2017
Gay Male

"Whichever of you bitches brings off the man fucking you, gets to double up in the other bitch's cunt." * * * * Eric Talbot had been a member of the Club since he was in his mid-thirties, almost 15 years ago, enjoying the variety of pleasures available at the hands, cocks and asses of its various members of staff. Neither a consummate bottom or top, he co...

A Sultan's Male Harem

by JASONSHOMOEROTICA on Sep 14, 2017
Gay Male

This is a homoerotic story set in an imaginary sultanate called Ras al Shahar located in the south of the Arabian Peninsula. The time is the late ninth century AD and the story starts in the year 870, some three hundred years after the birth of Mohammed, the Prophet of Islam. The place and characters are entirely a figment of the author's imagination whose o...

Pony Boy Ch. 05

by ChestersBoi on Sep 14, 2017
Gay Male

This is the fourth chapter of 'Pony Boy' and, if you haven't read the rest, then please do so first. Quite a bit of the story refers back to events in the earlier parts and it won't make much sense if you read them out of order. And, of course, there are the usual disclaimers; anyone involved in sexual acts is over eighteen and we're all fictional. Enjoy...

Pony Boy Ch. 06

by ChestersBoi on Sep 14, 2017
Gay Male

New readers – don't start here! This is chapter six of Pony Boy. My apologies for the long wait. It won't make too much sense unless you've read the rest so, if you're new to this story then I strongly recommend you find chapter one and start there. Usual stuff – we're all fictional and over eighteen. ******* I didn't move, I couldn't move, nor could I...

Oral Friends Ch. 06

by oralfriend on Oct 13, 2017
Gay Male

Oral Friends Six—Out of Town Adventure Due to a lack of other ideas at the moment I've decided to explore something I introduced in my last story, Rich's submissive desires. I hope you enjoy this story. ********** My friend, Rich, and I had explored his submissive fantasy the other day and we'd both found the experience very exciting. Rich had confessed t...

Oh Daddy - The Beginning Ch. 01

by Dom300022 on Oct 6, 2020
Gay Male

My name is Noah I'm a Senior and I'm currently attending Parker University and have been since the beginning of my College career. This school is filled with the most raggedy bummed kids you'd ever encounter on the streets, and the most prominent rich white kids in the whole county. I'm talking scarfs with polos, perfectly ironed khakis, dress shoes perfectl...

Luke's Early Years

by WittePiet on Aug 18, 2017
Gay Male

[This story can be read on its own, but it continues the story of Jonathan and David into the next generation. All institutions and characters in the story are purely imaginary.] * Chapter 1 Early years One of my earliest memories is when I was about six years old being taken for a walk by Uncle Arthur Rockwell in the wood that he and my cofather had p...