Gay Boarding School Stories

7,643 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 SmutMD.com

Homeward Bound Ch. 03

by sr71plt on Aug 30, 2017
Gay Male

I quickly found that my mother's "special services" operation paled in the face of what Mrs. Childress was capable of. I wasn't the only one on her staff giving extra attention for extra cash at the Swannanoa Boarding House. In addition to me for the men guests so inclined, she had two serving girls, Sadie and Clare, who did the same for the men who paid for...

Early Boarding School Experiences Ch. 02

by doris1957 on Apr 24, 2018
Gay Male

The story continues ... For the next few days neither of us tried to make contact with each other. I for one was still excited about what had taken place but still confused about what was really happening. It was obvious to me that it was all consensual but it was also something to be kept private between us and low-key. School life continued as before. Sw...

Homeward Bound Ch. 02

by sr71plt on Aug 31, 2017
Gay Male

When the scheme first got started, it seemed to be no big deal, really. By then there wasn't anything to protect and after the first time as part of the boarding house service there wasn't that much to be embarrassed about either. My family came to Asheville when I was just ten. For me, it was an improvement over the dreary coal mining towns of western Penn...

Early Boarding School Experiences Ch. 01

by doris1957 on Apr 24, 2018
Gay Male

I started boarding at an all male school at the age of 11. It was all so different from living at home with brothers and sisters, access to TV and a normal life as a prepubescent boy. After a few weeks the novelty wore off and life started to become harder. There was great emphasis on who was top-dog and a sort of hierarchy amongst our age-group began to f...

First Fumblings

by zaphod40 on Aug 22, 2017
Gay Male

"It's as long as my arm" murmured Steve with satisfaction as he unzipped my fly, inserted his hand into my pants and drew out my eight inches. I had not seen him for over a year, as I had left school just before my 18th birthday and he had stayed on an extra year to try for University entrance. He lived in the countryside about 90 miles from London and I ha...

Secret Cumming

by LilJacks on Aug 18, 2017
Gay Male

Author's note: This is based on a dream I had when I was 16, but decided on a boarding school where the characters in this are 18 (my age) so it isn't underage. Just to clear that up. And this didn't actually happen, but it is based on a person (not their real name). I hope you enjoy this and don't get bored because of this note... * Sitting in the back o...

The Valet Ch. 03

by SapphireBlueMist on Sep 14, 2017
Gay Male

~ Hi everyone! Sorry it's taken so long, but I have finally gotten round to writing the next chapter of Alex and Jason's lives. This chapter is a bit longer than the previous ones, but there is also less action. However, I think it's a necessary step for the story to develop. I hope you enjoy it, and as always, feedback is appreciated! Please note that absol...

Blake Gets Banged

by slutfucker101 on Aug 31, 2017
Gay Male

An 18-year-old public schoolboy gets banged by the servant. Joining the Upper Sixth Form at St Latimer College was challenge enough. Joining in mid-February was a disaster. With A-Levels less than three months away, and revision around the corner, Blake wanted an 18th birthday celebration to remember. Blake lowered himself and sighed as the rubber cock tea...

A Man's World

by Samuelx on Aug 18, 2017
Gay Male

Are you obsessed with gay sex? Come on, tell me the truth. Do you get all worked up at the very mention of it? Does the thought of a man fucking another man turn you on? Ladies and gentlemen, I would like to be the first to admit that I am completely obsessed with doing it with the guys. My name is Roger Stanley and gay sex is my addiction. It's my favorite...

Homeward Bound Ch. 05

by sr71plt on Aug 31, 2017
Gay Male

It was mere happenstance that I received the letter at all—and I remembered later that I had every reason to suspect that there had been other letters sent to me at the boarding house that I never saw. I just happened to be the one standing at the front door when the mailman came by and, although I didn't usually do so, I glanced at the addresses on the enve...