Headmaster Punishment Stories

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Alice Manipulated Ch. 08

by BeamMeUp on Sep 19, 2017
Exhibitionist & Voyeur

Alice, the sexy little pretty 21 year-old with a body that looks half her age, is fast being recognised as the star recruit for raunchy business couple Bernard and Lani. Their lucrative Companions' Corner 'hire a fantasy model' service and the weekly nude modelling classes called Artists at Work has Alice the Number 1 pin-up girl of their followers aged from...

Melanie Ch. 03

by StoryTeller07 on Sep 14, 2017
BDSM

Chapter 03 The sex party Working hard all day had the advantage of distracting Melanie from what might happen to her this evening. With the two silent women, Sophia and Sapphire, a banquet was being prepared which meant visitors to the mansion were expected. Who they were and what was expected of her was still a mystery for they were forbidden to talk an...

A Little Bit of Culture

by MarcLuterian on Jan 15, 2019
Fetish

Having turned 18 and in the last few months of Sixth Form I felt quietly confident about life and my future. University beckoned with the freedom and fun (and sex hopefully) that that entailed. Plus, today there were no classes, a trip had been organised to the theatre to see Henry IV Part One. The A level English students were studying it and although I wa...

Jenny's Kinky Desires Ch. 04

by MiloXarts on Oct 8, 2019
BDSM

© MiloXarts 2018 =================================== Dear Reader, thank you for following the story of Jenny! Thank you as well for all the comments I've got for this and all the previous parts! And last but not least, many thanks to WarEagle for editing and proofreading of this story! =================================== Chapter 1 "Mmmh," I moaned...

A Glass of Chablis Ch. 06

by Drmaxc on Mar 2, 2020
Erotic Couplings

George was back late. From seeing Doris he had gone on to make his rounds, seeing various friends, checking on them, sorting matters out. It was what he did. Something of an employment – unpaid of course, but he had his pension. Pensions indeed. It was not a problem. He was back quite late in the day. Ivy had been busy. The house had been cleaned, washing...

School Daze

by Croony on Dec 29, 2017
Fetish

Abbottsford College, situated in the City of London, was a prestigious all boys finishing school that catered for teenagers from the age of sixteen to eighteen. The pupils were mainly from rich and titled families who wanted their sons to experience the strict regime and make them into better adults. David Bryden was the headmaster that dealt with disciplin...

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...

The Punishment

by aaron1944 on Sep 2, 2017
Exhibitionist & Voyeur

Velda stood before the headmaster's desk and looked at him in horror. He had to be kidding, but she knew deep down that she had pushed him a little too far this time. Also, she had to admit that the punishment did fit the crime. Velda was a rebel; she was leader of the pack. She had been up before Mr. Bingham on more than one occasion for school uniform vio...

The Headmaster Ch. 03

by deadeye_76 on Sep 13, 2017
BDSM

Chapter 3. Christy's Punishment. I was trying to get some paperwork done, but couldn't concentrate very well. I kept thinking about what my wife had done to Christy and how that beautiful young thing was going to be coming back at about 3pm. I checked my wife's office at about 2:30 and she wasn't there. I walked all the way through to the other side and a...

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...