Gay Boarding School Stories

7,643 results
Orientation
Length
Source
Infinite Scroll

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...

My Freshman Roommate

by R10010 on Jan 8, 2019
Gay Male

My name is Jose and I'm a first generation Mexican-American. I'm the first person in my family to go to college and so far, my freshman year hasn't been everything I expected. I thought I'd be going home with a different girl every week. Some guys have a real skill with picking up women, but I don't. My roommate Stephen is even worse, mostly because he's alw...

My Time in the Monastery

by brownmonkk on Aug 18, 2017
Gay Male

Brother / Sister/Slave, ("TML") November 1970 "Good loving & Good Scourging" The story of a MASTER and his slave! 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 always imagined having my "first time" with a sexy gal, but nonetheless my first sex was great! I often fantasize and...

Classroom Adventures

by mmebutterfly on Aug 18, 2017
Gay Male

It was one of the first days back from winter break and 18-year-old Kevin was hiding out from an all school assembly. He hated the exclusive all-boys boarding school his parents sent him too, and was happy to think he only had a few months left before graduation. As a gay man in a school of rich jocks, Kevin hadn't come out to anyone, happy to just be labele...

Tales of a Cock Slave #39

by dprb65 on Sep 14, 2020
Gay Male

One evening at 7:00 pm, about two weeks after I moved into my new apartment, I was hanging paintings in my apartment on the living room wall. I had drilled the holes, but had to use a tack hammer to drive them in. I heard the doorbell ring and I opened the door. It was my neighbor, Matthew, 6', muscular, plainly good looking who often wears sweatpants with...

Seducing the Pizza Boy

by S_Queen on Feb 6, 2018
Gay Male

It had been a somewhat stressful week. I work as an international antiques dealer, you see. My work takes me all over, with a lot of tiring travel. As I near fifty, it is getting noticeably harder. Having said that, I do keep myself in excellent shape with a lot of working out and expensive beauty therapies, and my mind remains sharp and youthful due to my f...

Hot Shower

by CountGustaf on Aug 18, 2017
Gay Male

"So you spent three weeks on horseback getting here? You must be literally both saddle sore and grimy, Graf Cederhielm. Well,we have a good remedy for both: a hot shower," beamed Colonel Riesenheim behind his large oak desk. The colonel was rotund, surprisingly fat for a cavalry officer. I assumed he needed help to get in the saddle. "You have a hot shower...

Homeward Bound Ch. 04

by sr71plt on Aug 31, 2017
Gay Male

And then, one day, there was Stanford Dane—and eventually there was Abraham. With Stanford everything was different, nothing unfolded according to the set plan, and, amazingly enough, Mrs. Childress purred through the whole process. Dane came to Asheville at the height of an arts festival in which the new live drama theater was being launched. He came with...

Taken By My Teacher

by johnjeff on Aug 18, 2017
Gay Male

It was a usual day at my English private school (boarding). I had geography towards the end of the day which I had desperately been looking forward to as I could spend time staring at Mr Stevens (think late 20's, ripped, 5'10, dark hair) as he lectured on tectonics. However, this day would be different. The whole class was handed back their coursework, exce...

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....