Headmaster Punishment Stories

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Infinite Scroll

A Very Naughty Girl Indeed!

by Jonathan Phillips on Sep 11, 2017
BDSM

The PE teacher had buzzed ahead telling me to expect you. She had not however, prepared me for exactly what I was to be punishing you. I could easily have lost my job for the punishment I chose for you. Christ, I really should lose my job for the punishment I chose for you. *** There was a knock at the door... "Come!" I shouted. You stepped inside. You...

The Headmaster's Indiscretion Pt. 01

by emeraldangel on Sep 12, 2017
BDSM

Day One -- Journal entry Starting my new undercover assignment today. This one is going to be interesting, I expect. I will be posing as a 18 year old girl at Miss Priscilla's Boarding School. The chief says there have been some disappearances of girls from there and although the girls show up eventually, claiming to have run away...he thinks there is somet...

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...

Melissa's Story Ch. 02

by iraussieguy on Sep 13, 2017
BDSM

Author's note: This is the continuation of "Melissa's Story Ch. 01" - if you have not read it, I suggest you do before reading "The Schoolroom". Many thanks to all my fans, specially M, R & A, for their positive feedback. Melissa's story continues: Chapter 2: The Schoolroom Driving home from Matt's after my first spanking session I felt as if I was in an...

Mercedes Senior Year at St. Vincent

by OTKTop on Sep 17, 2017
BDSM

Mercedes senior year at St. Vincent Boarding school ***** When she was younger, Mercedes went to a very strict boarding school, one that still allowed corporal punishment. Usually the punishment was used sparingly but with a new Headmaster, Dr. Hoffman, more and more of the young women of St. Vincent Boarding School were ending up in the Headmaster's offic...

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...

Morgana's Painful Lesson Ch. 2

by Morganauk on Sep 16, 2017
BDSM

It was Friday afternoon and the last day of the school year. There was an expectant buzz in the air, as everyone's thoughts were concentrated on tonight's leaving party. Morgana was as excited as everyone else – she had big plans for tonight. Headmaster Dave had kindly agreed to hold the yearly event in his large country house. Only the older pupils were in...

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...

Sex School: Induction

by vixenoftheNorth on Sep 17, 2017
BDSM

Tori applied one last coat of bright red lipstick to her lips before stepping out of her parked car and crunching up the gravel pathway towards the imposing stone porch of the old school house. Her 6 inch platform heels sunk slightly with each step, and the gentle breeze sent a shiver round her toned thighs, which were barely covered by the short micro bodyc...

A Headmaster's Lesson Pt. 02

by LittleKay on Nov 20, 2018
BDSM

Sadie sat in the dining hall on Friday morning, thoroughly distracted from her grapefruit. She spent the rest of that Saturday night in Headmaster Davis' bed. After his bath, he'd taken her twice more. He fucked her like it was a punishment, as Headmaster Davis said it should feel, but she secretly reveled in the way he stretched her body. The first time hur...