Gay Headmaster Stories

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Teacher's Pet Ch. 08

by Goldeniangel on Sep 14, 2017
Gay Male

Cory followed behind the Headmaster, frightened and anxious about his fate. And Mr. Peterson's fate for that matter... he didn't quite understand what was wrong or why Coach Hamilton should be able to take charge of Mr. Peterson when the Coach had sex with him just the day before. Following the Headmaster into the office, he felt like he was in a daze as th...

The Harrington School for Boys Ch. 02

by AgentK on Oct 15, 2017
Gay Male

After Aidan delivered his file to the smirking headmaster, he quickly made his way to his room, still blushing in embarrassment. His roommate Graham looked up from the bed where he was reading a book. Aidan suddenly noticed something - the bed. There was only one. "Th-there's only one bed?" Graham smiled slightly as he sat up. "Yeah. It's meant to teach us...

Double Punishment

by Guy521 on Oct 8, 2019
Gay Male

Adam and Charlie sat silently outside the headmasters office, contemplating what was about to happen. Both young men had been caught fighting yet again, leaving Adam with a split lip and ripped shirt, and Charlie with a bruised eye. The sound of the headmaster's door opening signalled for the boys to enter. The Headmaster stood behind his desk looking less...

Halloween Party Hollow Weenies

by walterio on Nov 4, 2019
Gay Male

INVITATION Sitting across from Archibald Thompson, the private school's Headmaster, was Stanley Morrison, the school's largest benefactor. Stanley was having a Halloween costume party for his special clients. He needed five students to attend the party. "So, Stan, you are asking me to send five gay students to your home for a Halloween party." "That is c...

Teacher's Pet Ch. 10

by Goldeniangel on Sep 14, 2017
Gay Male

Author's Note: I enjoyed writing this series... I hope that you enjoyed reading it =) ----------------------------------- Sighing happily the Headmaster pulled his limp dick from Mr. Peterson's ass and slapped the firm cheek. Looking up he asked, "Would you like a try Cory?" Cory stared at the pink, slightly gaping hole, his cock buried in Mr. Peterson's...

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...

Exodus

by gaytheist on Aug 18, 2017
Gay Male

One night that spring, a lost tropical wind strummed the valley and hillside campus, but with final exams looming, the dining hall at breakfast remained muted. Then in morning assembly the portly headmaster surprised everyone when out of the blue he announced a school holiday, laughing heartily as we cheered, whistled, clapped and stamped for what seemed lik...

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...

A New Broom Sweeps Clean

by JASONSHOMOEROTICA on Aug 17, 2017
Gay Male

A Homoerotic Story By Jason Land FOREWORD This story covers a two year period in the life of one, Dr. Andrew Waterlow, a brilliant Oxford classist who turns to school teaching as a profession, but who who is finally appointed, aged only thirty, to a research professorship at the University of Oxford. Depending on context, he is variously referred to in t...

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...