Gay Boarding School Stories

7,643 results
Orientation
Length
Source
Infinite Scroll

The Housewarming (Completed)

by obieblu_tumblr on May 8, 2017
Gay

'At the station. Be there in 30.' You quickly text back to your friend, Chris, as the subway pulls to a stop. You step on and easily take a seat, as you're boarding at a stop at a parking garage outside the city. Driving in the city is still a bit intimidating, and you expect you'd get towed at some point over the weekend as the signs and regulations here ar...

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Bangkok Airport

by SomeOne_84 on Aug 18, 2017
Gay Male

Disclaimer: Read at your own risk. If you get caught by your local law enforcement agencies while doing it, well, you are one unlucky fellow. I was going to Malaysia and had a long stopover at Bangkok's Suvarnabhumi airport so instead of waiting at the airport I went to the city for a while. After I was back at the airport I was waiting for my turn at the...

The Bully Pt. 02

by ryan_devry on May 11, 2020
Gay Male

"Oh... yeah... ahhh!" By now I'd done this often enough to be able to tell from Leander's moans how close he was to shooting his load. He gripped the back of my head — that meant he was very close, and that he wanted me to swallow. I wasn't going to refuse him, but I struggled a bit anyway, tried to pull back. You know, just for show. It worked like a char...

Parting Gifts

by peachmangopie123 on Apr 21, 2020
Gay Male

Disclaimer: All names and events in this story are fictitious. The setting is a fictional college in Cebu, real city in the Philippines. Author's Note: I wrote this story as an outlet for my secret fantasies without any intention of publishing. But with the amount of effort I put into this, I decided to give it a try this once. ***** I never really expec...

Bound to Bait

by sr71plt on Oct 15, 2017
Gay Male

"The offer is tempting, yes," The elegantly clad Guiovani Lucano, president of Unipro, said, "but the French cosmetic firms are eager to have whatever Dragobotania we can produce. There's really no sufficient incentive I can see to change that and sell to the United States instead." He was talking to the American chemical dealer, Nicholas Reynolds, as they...

First Time by Candlelight

by Richard963 on Aug 18, 2017
Gay Male

There is a first time for everything in life. The experience of having sex in one form or another is such enjoyment that one never forgets it. So it was with my sex life. I was born in 1954 to an unmarried mother. She tried to bring me up by herself and I remember her as loving mum but when I had to go to school she could not afford to clothe me so I was fos...

Speech and Debate Pt. 02

by DAMackey on Sep 25, 2017
Gay Male

Continental Breakfast I woke, or to be more accurate, I was awoken, on the morning of my actual birthday by the sound of the chain-tracked hotel curtains being yanked apart. The room lightened to a misty grey, the setting moon bouncing silvery-white light off the snow from the previous evening's blizzard and mixing with the faded yellow street lamps from th...

Aaron's Summer of '77 Ch. 06

by SDR2000 on Sep 12, 2018
Gay Male

Chapter 6 - August 22nd August 22nd arrives and I am waiting at the Voyageur Colonial bus stop on Perth Street in Brockville for the morning bus to take me up to Ottawa for my orientation interview with Camilla Mezaros. Adam has to work today and my Dad as well. So, I am on my own to make this trip to finalize all my courses and pay final tuition for commen...

Jocks of the South Pt. 03

by scottgoulding123 on Sep 14, 2017
Gay Male

The Older Brother Over the next week, Nick gave Francis a blowjob twice and he'd gotten fucked by him another four. The only day they hadn't done something together was when Francis had to go with his parents to drive to the airport in Dallas. Francis' older brother—Matthew—was coming over during Spring Break to visit his folks and he'd flown in from Los An...

The Mile High Club

by emfin on Aug 18, 2017
Gay Male

Tom walked down the passenger terminal with hurried steps. He knew he would be arriving slightly late to the departure gate and hoped that he would catch his transfer flight on time. His last flight from Paris had landed to Chicago late by more than 45 minutes and it had recessed his change time to only 30 minutes. It could be an impossible task, but he hope...