Headmaster Punishment Bdsm Stories

61,534 results
Orientation
Length
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Infinite Scroll

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...

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...

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...

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...

Schooling

by VGracen on Sep 12, 2017
BDSM

She sat angrily in the hard chair outside the office, glaring at the two aides who had apparently been assigned to watch her. “SO WHAT if I tried to run away last night...! I didn’t ASK to be sent to this STUPID school. It’s not my FAULT that my mother died and that my stepfather “just can’t handle me” any more! SO WHAT if the drinking and drugs and parties...

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...

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...

Lucia Gets Spanked

by jennanips on Sep 12, 2017
BDSM

*This story is a work of fiction. All resemblances to any person are purely coincidental. All rights reserved by author.* * Lucia was really hoping this was going to work. She looked herself over in the mirror. Although Lucia was in her mid-thirties, she looked much younger, especially in the schoolgirl outfit she had donned. The top was a white button-do...

Sean Leaves Karen

by jacksgirl on Sep 17, 2017
BDSM

There was going to be a party. Sean invited several friends and business associates. He told us to be prepared for twenty guests. Jillian and I cleaned and cooked for days. Well, ok, Jillian did most of the cleaning. Since I am an excellent cook, the kitchen was my domain. And I loved it. Of course, Sean insisted Jillian and I remain naked at all times. Whic...

New Punishment System Demonstration

by TUnicornLiterotica on Jun 15, 2020
Transgender & Crossdressers

DISCLAIMER: This story involves the degradation of a trans character, this is not meant to be read as transphobic scripture. The writer, being me, is trans, not that makes it automatically okay, but just understand, this is a fantasy, and it fulfills some of my submissive desires. Characters all 18 years old above etc. * * * * * Carla had just been pulled...