Gay Headmaster Stories

67 results
Orientation
Length
Source
Infinite Scroll

Teacher's Pet Ch. 07

by Goldeniangel on Sep 14, 2017
Gay Male

The next day when Mr. Peterson was back, Cory was relieved. Although he'd enjoyed sucking off Buck in the showers, and then being fucked by Coach Hamilton, he also wanted to get back into his regular routine. And Mr. Peterson was much more gentle and comforting than the other two had been. Walking into the classroom and seeing Mr. Peterson waiting for him w...

The Ingram-Lewis Chronicles Pt. 03

by JASONSHOMOEROTICA on Aug 17, 2017
Gay Male

THE INGRAM-LEWIS CHRONICLES – PART 3 PATRICK'S SCHOOL FORTUNES SOAR – BEATING AND SEX GALORE. A Homoerotic Short Story By Jason Land CHAPTER 1 We left Patrick Ingram-Lewis at the end of his penultimate year at Rigby School, where he had been, much to his surprise, elevated to the level of Senior Prefect. He had revelled in his new role; after a timid...

The Harrington School for Boys Ch. 03

by AgentK on Nov 27, 2017
Gay Male

It was around midnight on a Thursday night, and Graham Ainsley was sleeping soundly when suddenly he was startled awake by his bedroom door opening and a light turning on. He looked up to see the prefect, Reed Burgess, dragging his roommate Aidan by the arm. Aidan appeared to have been crying. Reed pushed him roughly towards the bed, giving him a scornful lo...

The Ingram-Lewis Chronicles Pt. 04

by JASONSHOMOEROTICA on Oct 15, 2017
Gay Male

PATRICK "IN LOCO DOMINI" CANE AND BIRCH REIGN SUPREME AT RIGBY SCHOOL A Homoerotic Short Story By Jason Land CHAPTER 1 In Part 3 of the Ingram-Lewis Chronicles, we had left Patrick Ingram-Lewis on the first day of his final year at Rigby School where he had, much to his surprise, been appointed Head Boy. But his appointment went much further than that...

The Ingram-Lewis Chronicles

by JASONSHOMOEROTICA on Aug 17, 2017
Gay Male

THE INGRAM-LEWIS CHRONICLES OLIVER'S FIRST SCHOOL DAYS A Homoerotic Short Story By Jason Land This is the first of a series of, stand-alone, short stories set in the early part of the twentieth century, concerning the life and times of members of an English upper class family, the Ingram-Lewis's. ***** The cane was tapping gently across a splendid pa...

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...

The Harrington School for Boys Ch. 01

by AgentK on Oct 15, 2017
Gay Male

Dublin, 1926 Aidan was folding his laundry when his roommate Stephen came in. "Hey, Aidan. Matron wants to see you when you're finished with that." Aidan sighed. He had an idea what it was about. He was now eighteen, and could no longer stay at the orphanage. The matron probably wanted to see if he'd found a job and a place to live yet. He hadn't, and was g...

The Ingram-Lewis Chronicles Pt. 02

by JASONSHOMOEROTICA on Oct 15, 2017
Gay Male

PATRICK INGRAM-LEWIS - OLIVER'S FATHER A Homoerotic Short Story By Jason Land FOREWORD Subsequent to publishing the first story in the chronicles of the Ingram-Lewis family, the present Headmaster of Rigby School, having read the first account, kindly gave me access to documents from the school archives which throw a somewhat different light on the scho...

AD 2022: Welcome Back Cane & Birch!

by JASONSHOMOEROTICA on Aug 17, 2017
Gay Male

Foreword My regular readers will all be well aware of the fact that my stories tend to be rather long, This, my latest offering is no exception and runs in total to some 43,000 + words. Set in the near future in post Brexit Britain, it explores how four different establishments react and adapt themselves to the latest law, which once again allows corporal p...

Sebastian Finds Himself

by JASONSHOMOEROTICA on Aug 30, 2017
Gay Male

Prologue My business card is very discrete. It says quite simply Sebastian - Male Escort By appointment only Telephone xxxxxxxx For those unfamiliar with the term 'Male Escort', let me explain. It is a euphemism for a man who is a professional copulator, selling what is usually known as anal stimulation to his exclusively male clientele. Crudely put, a M...