Gay Headmaster Stories

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

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...

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...

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 Ingram-Lewis Chronicles Pt. 06

by JASONSHOMOEROTICA on Oct 15, 2017
Gay Male

PART 6 - PATRICK'S FINAL TERM AT RIGBY ***** CHAPTER 1 Patrick Ingram-Lewis, the Head Boy had just returned to Rigby School after the Easter holidays. It was the last time he would be returning to the school at which he had been a pupil since the age of thirteen. At the end of this, his final term, he would be leaving the place for ever to start the next...

Gentlemen's Club Ch. 04

by Ywashere on Sep 14, 2017
Gay Male

This story is a work of fiction. All characters in this story are 18 years of age or older. * The two boys huddled together under the blanket; one, the blond, was apprehensive and shy while the other, dark of hair and eye, was boastfully bold and commanding. Both wore identical pajamas with a crest on the breast pocket -- a uniform of some kind. The room...

Teacher's Pet Ch. 09

by Goldeniangel on Sep 14, 2017
Gay Male

Author's Note: There is a bit of an element of reluctance in this story. Otherwise, just gay sex. Enjoy! =) ---------------------------------------- Mr. Peterson wasn't in class the next day, so Cory couldn't ask him about the room that he was supposed to go to after school. When he mentioned it to Sam, the young man just shrugged his shoulders and kept w...

Gentlemen's Club Ch. 08

by Ywashere on Sep 14, 2017
Gay Male

(All characters are 18 years old or older.) Well, I promised that I'd post a new story as soon as I got 10 responses -- so here it is. Hope you all feel it was worth the wait :-) Note for this story: I have a thing about using fancy language in sex scenes (as you may have noticed in Ch. 4) -- I blame this on the first erotica I ever read, which were "class...

The Head Boy's Fag Ch. 02

by JASONSHOMOEROTICA on Oct 15, 2017
Gay Male

THE HEADBOY'S FAG - CHAPTER 2 THE FAG'S PROGRESS AT OLLERTON COLLEGE A Homoerotic Story In the first episode of this story, our hero, the Honourable Timothy Edward Clive Lattymer-Smith, the second son of the fourth Lord Lattymer of Adel-cum-Eccup in the County of York, had found himself selected by the Head Boy, Sebastian Jeremy Mottram, of Ollerton Schoo...

A Grammar-School Boy Looks Back

by JASONSHOMOEROTICA on Aug 18, 2017
Gay Male

Reminiscences of a Grammar-School Boy By Jason Land These are the reminiscences of a working class, grammar school boy in the years immediately following the end of the Second World War in May 1945 in the industrial north of England. My name is Jonathan David Robertson and I was born in June 1936 so that in 1945 I was eleven years old. For those of my re...

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...