Headmaster Punishment Stories

31,842 results
Orientation
Length
Source
Infinite Scroll

St. Mary's 6th Form Sluts Ch. 17

by Celtic_Heart on Sep 14, 2017
Novels and Novellas

Shona and Jane sat nervously outside Mr. Beattie's office. Inside, the Battle-axe, Miss Carlisle was appraising the headmaster of the girls' latest misdemeanour. "What's the bets she tries to have us expelled again?" Shona asked her blonde friend. "Mr. Beattie won't do that, not with the exams starting next week," Jane replied. "The Battle-axe is sure to...

Class Rules Ch. 03

by 0131aj on Sep 17, 2017
Fetish

Shirley thought that the Headmaster would now agree to retaining both her husband, Julian, and herself in their teaching posts at the all girls school. She had allowed him to spank her over his lap, had held his large cock (much larger than Julian's) in her hand and had not tried to escape when he started to shoot his spunk all over her face. Julian had neve...

Spank Me

by Goldeniangel on Apr 3, 2019
Fetish

Authors' Note: This is a rough spanking story involving anal sex. Enjoy! ---------------------------- Hannah shivered as she walked down the hallway to the Headmaster's office. She was a horny little slut and she often got in trouble... ever since the very first day that she'd arrived at the all girl's school at the tender age of 18. That day she'd gotten...

The Headmaster's Room Ch. 01

by Mag58 on Sep 12, 2017
Fetish

This story is in three parts and begins in 1985 when I was 18 and finally ends last year. "Miss Simpson! Go straight to the Headmaster's room now!" Mr. Flanders shouted as he pointed to the Religious Knowledge classroom door. I shrugged my shoulders and slowly made my way to see Mr. Skinner for the third time that week. With hindsight, at that time of my l...

Margaret Visits the Headmaster

by Pimpleia on Feb 6, 2018
BDSM

'You haven't written anything for Literotica for a while.' It was Saturday and we were enjoying a late breakfast after a leisurely bout of summer morning lovemaking. Her face still aglow with post-orgasmic blush, Margaret dipped a finger into the honey jar and licked at the sticky sweetness with delicate dabs of her tongue, before sliding the whole finger i...

A Headmaster's Lesson Pt. 01

by LittleKay on Nov 6, 2018
Fetish

Greetings! Thanks for taking the time to read my story. Feedback and Comments are welcome! Please read the disclaimers at the end before leaving negative comments on the themes or content. This *is* a dark, twisted story. Apologies in advance. _________________ The only thing worse than growing up in a wealthy religious family was being sent to boarding...

Class Rules Ch. 02

by 0131aj on Sep 17, 2017
BDSM

One afternoon during the following week, Mr Gallagher was casually looking out of his window onto the lush green lawns below his study and saw something that took his eye. He rang his bell and his faithful secretary Miss O'Hare entered his room quietly. "You called me Head Master?" The Head nodded. "I have just seen Mrs West crossing the lawn from the gymna...

The Headmaster

by P_V on Sep 13, 2017
Erotic Couplings

Though I must apologize to my wonderful readers who are hungry for more "Orgasm Torture" for not posting any installments lately, I hope that this "early work" of mine will amuse and arouse them. There a hundreds of fantasies that take place in all-female academic settings (and that's just in *my* mind!) but hopefully, you will find this one different enough...

Jessica at the Finishing School Pt. 04

by MALIBUMAN666 on Sep 25, 2017
Fetish

This story was written in 2000, annoyingly I am having to transcribe it from a physical copy since that is all I have available. I hope you enjoy it and you think it worth my efforts. This is part four of five, since the feedback has been largely positive I am cracking on with the rewriting/transcribing and the last part should be done very soon. I'm postin...

Arcadia Castle Ch. 01

by Hal1031 on Jan 8, 2018
BDSM

Chapter 1: THE HEADMASTER The taxi driver checked his odometer, sighed, and cranked the A/C as high as the knob would go. The desert was especially unforgiving this time of year. Sweat trickled down my neck and rolled inside the paper-thin, white tank top they'd so generously provided for my trip. No bra, no panties allowed. Just the tank, a pair of cheeky...