Headmaster Punishment Bdsm Stories

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Orientation
Length
Source
Infinite Scroll

Morgana's Painful Lessons Ch. 4

by Morganauk on Sep 17, 2017
BDSM

Morgana tensed as she thought she heard the rustling sound again, but there was nothing to be seen as she peered around; its probably just my imagination she thought shivering now as the day grew cooler. She reflected upon the morning's events and wondered how it was that she found herself in these predicaments. How many other people ended up tied to a tree...

School Girl Gets Punished

by Promiscousgyrl on Sep 12, 2017
First Time

I was a student at an all girl boarding school and I was in my last year at the school. I was 18 and no longer a virgin. It was taken by the head master of the academy, head master Anton. It happened one day after I was taken to his office for the 20th time that month. I was what all my teachers called a trouble maker, a rebel. This last time I "accidentall...

Academy of Sighs Ch. 01

by barabajagal001 on Sep 16, 2017
BDSM

Note: This story has a rather long build-up to sexual intercourse itself (as in, not in this chapter), just as an FYI for people who aren't into that kind of thing. And yes, all characters are over 18, as always. ----- A warm breeze kicked up as a young man stepped out of the black taxicab that had brought him. He looked up at the formidable building befo...

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...

Another Year at St Cat’s Ch. 01

by nightvoice2 on Sep 25, 2017
Novels and Novellas

Discipline and Dilemmas (1) ----------------------- Wednesday, 18 September ----------------------- Jenny Coombes rolled over and looked at the clock on her bedside table through half-open eyes. It was only half-past-six so she still had another hour before she had to get up to go to work. Her boyfriend, Derek, was still asleep, snoring quietly beside he...

Suzy Matron Ch. 03

by robin35 on Sep 19, 2017
BDSM

Attached to the collar and chain and with her nipple suckers and chastity belt on Matron looked so sexy I could have fucked her there and then but I was now the Master and I had to remain in charge of the situation. I pulled the chain and said. "Off the bed slave." "Yes Sir." She said. I watched as she got off the bed and began to walk out the bedroom. "...

Sex Academy For Young Ladies

by Blucher on Sep 12, 2017
Exhibitionist & Voyeur

Number 37 Rue Cordier, in the Neuilly suburb of Paris, France is a large and elegant house set at the end of a long driveway and screened from the street by tall poplar trees. It houses the offices of the municipal council. From 1891 until 1914 this address was known to many of the wealthy and titled families in Europe. At that time there was a polished bras...

Beat Me Harder, Master

by Tattletale on Sep 25, 2017
BDSM

My Mistresses parted the curtains and we peeked into the sold-out theater. "I've never seen such a big crowd," one said. "Standing room only," said the other. "They have come just to see this slut whipped and raped. I can hardly wait to take a cat to that fine ass of hers." "DRAG THAT WHORE OUT HERE!" The gruff order came from one of the five Masters. The...

Educating Alex Ch. 04

by FluteMaster on Sep 15, 2017
BDSM

By the side of that old tree trunk, in that clearing, using that same rug on which, earlier, Alex had knelt while taking Richard deep into her mouth and drinking his cum, together they shared food, wine and personal stories. Richard talked about his finding and exploring the BDSM scene. Initially, during his marriage it had been theoretical, in that he had...

Owned by my Mother-in-Law Ch. 04

by Sputnik57 on Sep 13, 2017
BDSM

The area by the window had a padded surface; no doubt Blanche's departed husband and many other enslaved men had been made to kneel for hours at this window, whilst they contemplated their fate on just such an evening as this. The padding would not be for their comfort, it would be there to ensure that their knees functioned when the time came to entertain....