Headmaster Caning Naughty Girls, Erotic Sexy Stories 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...

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...

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...

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!...

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...

View From a Window Ch. 04

by Drmaxc on Sep 28, 2020
Exhibitionist & Voyeur

Three people in a car, travelling down little sun-drenched roads in search of a local beach. Graeme driving with Jill beside him and Mandy in the back. The air-conditioning on. "You all right there in the back, not too hot?" A day for the beach rather than sightseeing. The villa had a swimming pool so the sea was not essential for a cooling dip and they di...

Ultimate Humiliation Ch. 03

by DAVES4000 on Sep 19, 2017
Fetish

Cara is so looking forward to her third visit to The Dungeon Room. She spends all week planning her schedule so that she knows there will be no interruptions come next Saturday. She has selected the school uniform shop where she needs to be the school clothes, and is really looking forward to doing that this afternoon. She wants to pick out the nicest unifo...

Sex Academy For Young Ladies Ch. 04

by Blucher on Sep 12, 2017
Exhibitionist & Voyeur

The following story has been compiled from the diaries kept by a teacher at the Rotenberg Academy For Young Ladies in Paris. The diaries are now in the National Archives. As explained in the previous stories, the school was founded by Professor Alphonse Rotenberg in 1891 to instruct the daughters of rich and titled families in the finer arts of sex. It was w...

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...