Headmaster Punishment Bdsm Stories

61,534 results
Orientation
Length
Source
Infinite Scroll

The Headmaster Ch. 04

by deadeye_76 on Sep 16, 2017
BDSM

Chapter 4. Christy's Back... with a friend! We hadn't had any action of any kind, which was surprising and I kept mulling over different ways for my wife to get her share of attention. I was thinking about something to do with the Halloween party that was coming up while my wife and I sat in the closet one day when something very interesting happened in the...

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...

Alice Ch. 01

by Daddys_Touch on Sep 14, 2017
BDSM

Alice is an 18 year old girl studying at a 6th form college which is part of an all-girls boarding school. This story contains scenes of sex, violence and gunplay. If you are not comfortable with this: do not read on. * Alice left registration, pushing open the door that lead outside and turned in the direction of her English class. She heard someone calli...

The Party's Ripe for Caning

by lesliejones on Sep 19, 2017
BDSM

It was a most unusual change for the boys in the senior class at Hamilton Hall, an elite high school, when the Headmaster, Mr. Henderson, appeared in their class to introduce them to their new home-room teacher, Miss Linda Crawford. First of all, there had never even been a woman teacher at Hamilton Hall, much less one so young as Miss Crawford, nor did it s...

Mercedes Senior Year at St. Vincent Ch. 02-03

by OTKTop on Aug 28, 2018
BDSM

Chapter 2: Mercedes is aroused from her spanking. (This is more of a story I have written for a submissive friend of mine. She likes to imagine what it could have been like to be spanked at her boarding school. It's only real in that this is what she imagines happening.) Mercedes walked quickly back to her dorm room, her mind clouded with a variety of thou...

The Headmaster's Room Ch. 03

by Mag58 on Sep 12, 2017
Fetish

My story jumps forward 20 years to May of this year. In the intervening years I've been married twice, lived with two other guys and never had any children. My career, as it is, has consisted of a succession of dead-end shop and restaurant work; moving from town to town across the UK and a Summer in Ibiza. "Well, well, well...some people never change. Do t...

Schoolgirl's Punishment

by mybaby on Sep 16, 2017
Novels and Novellas

Sandy was having a bad day, could it get worse? Simple answer? Yes! Much worse, much, much worse. Sandy was in the top form in her final year, A level study was going OK, and all things being equal University next year should be on the cards. On the other hand, her love life was just the opposite. Sandy had convinced herself she had not reached the age yet w...

Six of the Best Ch. 03

by KinoKe on Sep 17, 2017
BDSM

'NO RUNNING IN THE CORRIDOOR.' The Headmaster's voice rang out loud and clear. For a brief moment the three miscreants halted in their tracks and cast a guilty glance in the direction from which the edict had come. 'How many times do you boys need to be told?' The ringleader muttered something appropriately apologetic, and then all three walked, cautiousl...

Six of the Best

by KinoKe on Sep 17, 2017
BDSM

'Ah. Mrs Preston. Do come in.' The Headmaster rose slightly from behind his large desk but the late-afternoon light flooding in through the windows behind him made it difficult for Mrs Preston to see him properly. There was, however, no mistaking his rich authoritative voice. 'It's Dale, isn't it?' 'Delia,' Mrs Preston said. The Headmaster turned his he...

Bringing Her Along Ch. 06

by honourableboy on May 30, 2018
BDSM

- well my dear. We should get dressed and get going. And then to us - You two. Chauffeur uniform. Slave. Just as you are. - And boy, go get the cage in the back of the truck. Tamara and I dashed to our rooms to get into our Chauffeur uniforms. Something we could be seen in the outside world. For me it was shiny black shoes, pressed and tight dress slack...