Gay Boarding School Stories

7,643 results
Orientation
Length
Source
Infinite Scroll

The Thirst Within Ch. 01

by tauger on Aug 17, 2017
Gay Male

I have always known I was gay. For years I had tried to hide it. My Name is Oscar I go to a boarding school and am in my last year here. I'm 18 and still haven't found a boy friend how depressing is that. You cannot imagine the shit I have heard people say to the gay people at my school. That is the main reason why I am still in the closet. I'm 6'2...

Parallel True Love

by luvkitten on Aug 18, 2017
Gay Male

Francis took the blame. Francis was cool like that. He just spoke up, said it was all his fault, told the headmaster that I hadn't been any where near him when it had happened. Everyone liked Francis, the headmaster would let him off with some time-consuming but pretty trivial punishment; the new pupil, the new English pupil. Francis would have to practice h...

Cummuters Pt. 02

by shiremantoo on Aug 30, 2017
Gay Male

Part Two: Stephen Stephen and I hadn't known each other for long: His parents had returned from abroad and he had transferred from his boarding school to my day school at the beginning of term. I had been appointed his mentor, to show him around and help him to settle in and over the next few weeks we got to know each other really well. One day, we had fini...

Brother / "Sister"

by brownmonkk on Aug 18, 2017
Gay Male

WOW, "it" finally happened!!! I had had my first sex, and it was with a fellow monk in the monastery. It was great. I was a 20 year old virgin and had fantasized about both woman and men. I distinctly remember "wanting" Sally and Roberta in grade school and Cathy and Bonnie in high school boarding school. Never did anything about those feelings and practice...

Brother/Sister/Slave

by brownmonkk on Aug 18, 2017
Gay Male

Brother / "Sister" " TML", November. 1970 A Monk's monk or two virgins in the monastery; "Good loving & Good Scourging "Sissy" does her magic. WOW, "it" finally happened!!! I had had my first sex, and it was with a fellow brother monk in the monastery. It was great. I was a 20-year-old virgin and had fantasized about lots of women. I distinctly remember...

The School of Freedom and Love

by Jam18 on Aug 18, 2017
Gay Male

Oh, man, it can't be morning already. I rolled around on the bed and checked the time. "SHIT," I said out loud. It was 5:30 a.m. and I only had one hour left to say goodbye to my room, to my house, to my life. Ok, maybe I was being too dramatic, but being sent off to boarding school wasn't my idea of a great eighteenth birthday present. Yep, that's how I was...

A Helping Hand

by MyNameDoesNotMatter on Apr 17, 2019
Gay Male

I'd just turned off the light in my bedsit (a perk the lucky few who were 18 and in their last year at boarding school were entitled to, which meant no more sleeping in communal dorms), and climbed into bed. I was drowsy and while my thoughts wandered, my hand dipped under the bedsheets and idly started playing with myself. I wasn't masturbating but simply...

Homeward Bound Ch. 07

by sr71plt on Aug 30, 2017
Gay Male

Happily Trudeau was not completely serious when he told me there would be more sex than work on my book in his home. He was fully professional in the art of creating first-class novels. What was true, though, was that my work was taken completely apart and put back together again. And, although he was blunt with his critiques and was a hard task master, Trud...

Thierry

by zaphod40 on Aug 18, 2017
Gay Male

During the three years I spent at University some of my most enjoyable time was spent playing for the College rugby football team. Rugby is a tough, physical contact sport requiring courage, fitness and specific talents. It's no wonder that after a game there's a good deal of horseplay in the changing-rooms and a lot of badinage and boasting about sexual con...

A Night in the Pennines

by Timpoo on Oct 24, 2018
Gay Male

This is a simple straightforward tale of two guys who meet and enjoy a night together whilst they walk in the hills by day. It's pretty innocent and won't take long to read. It won't be continued. *** I had enjoyed a few days off from my work and as all my mates were working I packed my rucksack and headed for the hills to walk a few stages of the Pennine...