Headmaster Caning Stories

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The Caring Headmaster...

by JOHNKEY2222 on Mar 13, 2018
BDSM

"Oh Alan, this stuffy old school gives me the creeps." said Dorothy to her handsome Husband, the new school master of the dreaded upper sixth. Alan agreed with his beautiful young Wife, "it is a bit old fashioned Dorothy, rigidly maintaining the 'traditional' school values, as everyone keeps endlessly repeating." They were alone now in the school master's...

Painful School Reunion

by djt_one on Sep 19, 2017
BDSM

It had been over 6 months since John and Sue had first been introduced to the painful pleasures of caning by the fraudulent Dr Hay. Whilst they realised that his methods would not help their chances of conceiving their first child, they had found another dimension to their sex life. John very much enjoyed caning his wife, and Sue enjoyed the sex afterwards!...

A Visit to the Gym

by djt_one on Sep 17, 2017
BDSM

It took two weeks for the cane marks on Sue's behind to fade. This was not surprising after what had taken place in the headmasters study at the school reunion. Not only had Sue been soundly thrashed, she had also been thoroughly fucked by her old headmaster. All of which had happened while John, her husband had looked on, and at some stages taken part. Ther...

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...

Taught a Lesson

by goodnight_sweetheart on Sep 12, 2017
BDSM

The cold December rain was beating hard on the classroom windows. Amber watched it run down the glass; she liked the rain but wished it wasn't accompanied by the chilling wind. The school's heating wasn't working again, so all the halls and classrooms were freezing. Amber glanced over at Dru, her best friend whom she also shared a room with, Dru smiled sligh...

Schooling

by VGracen on Sep 12, 2017
BDSM

She sat angrily in the hard chair outside the office, glaring at the two aides who had apparently been assigned to watch her. “SO WHAT if I tried to run away last night...! I didn’t ASK to be sent to this STUPID school. It’s not my FAULT that my mother died and that my stepfather “just can’t handle me” any more! SO WHAT if the drinking and drugs and parties...

The Headmaster's Room Ch. 02

by Mag58 on Sep 12, 2017
Fetish

When the bell rang for the end of the morning lessons at 12.30; I was strangely disappointed at not having been called back to Mr Skinners' office for him to finish my punishment in his study. I ate lunch with some girlfriends then hung around the gym buildings smoking cigarettes and talking about a party that we were going to on the Saturday night. As the b...

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...

Earning those stripes

by JOHNKEY2222 on Jan 6, 2020
Loving Wives

I just found out old Bill Brown is mad about my sexy young wife Brianna. Well that's what she's telling me and she has my swollen manhood nestled in her soft warm hand, as she slowly strokes it. So it's just a lovely little tease but it's making my todger tingle like crazy. It's a good tale too, Bill Brown is a handsome older man, think of Christopher Lee i...

First Interlude

by tovesslithy on Sep 14, 2017
BDSM

24 First Interlude Helen Shagton was forty-two years old. Despite this very adult age, she was nursing a very recently and well-caned bottom. She was just returning home by car. However, she had felt, as she so often did, that she really needed a good, hard, school caning style punishment herself. The Headmaster, had, naturally, been very happy to oblige h...