School Punishment Stories

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The Party's Ripe for Caning Ch. 03

by lesliejones on Sep 19, 2017
BDSM

[This story takes place in a prep school which prepares pupils for three years after high school for university, from ages 18-20. Previous chapters explored Miss Crawford's introduction to the strict disciplinary regimen as the first female teacher of the boys' school.] Linda Crawford now had completed her second full year as an English teacher at Hamilto...

Trinity Finishing School Ch. 01

by ProfRighteous on Sep 19, 2017
BDSM

I was sitting in the baggage claim area of the airport waiting for my niece's plane to arrive, wondering if I had been a sucker to agree to this. Three days ago, I had been just sitting down to dinner when my phone started buzzing. Figures, people always call me at the most inconvenient times. I fished it out of my pocket and saw it was my brother Matt. "He...

The Feared '57' Ch. 01

by lesliejones on Sep 12, 2017
BDSM

For Kathy—whose presence has inspired me and added joy to the world Note: This story about a private girls' school features only characters who are 18 or over. Janet Sanders had been teaching for several years when she was recruited by an old colleague to join the faculty of a new experimental private school—they preferred to be called "independent," of...

The Party's Ripe for Caning Ch. 05

by lesliejones on Sep 19, 2017
Fetish

This is a series of stories about the impact of the new female teachers at the traditional school for boys 18 and over, Hamilton Hall, dedicated to preparing them for college but insistent on retaining corporal punishment. The school first hired Linda Crawford and now has both enrolled girls over 18 and brought on two more female teachers. There is some refe...

The Feared '57' Ch. 05

by lesliejones on Sep 13, 2017
Fetish

This story will make more sense if you read the previous instalments. All of the characters are 18 or over--the school is a college preparatory institution that only accepts students who are age 18 or over. Much to her pleasure, things had finally settled down at school for Janet Saunders. The thirtyish English teacher had endured a disastrous introducti...

E.N.F. School

by ittybittyht on Apr 22, 2025

Welcome, you are the new headmistress of ENF School. This school is dedicated to correcting female behavior. It neighbors the male corrective school ENM School, but the girls are forbidden from communicating with the boys school. The rules of the school are as follows: Uniform Rules Girls must wear full uniforms Monday - Friday. They are subject to uniform...

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The Caring Headmaster...

by JOHNKEY2222 on Mar 13, 2018
BDSM

"Oh Alan, this stuffy old school gives me the creeps." said Dorothy to her handsome Husband, the new school master of the dreaded upper sixth. Alan agreed with his beautiful young Wife, "it is a bit old fashioned Dorothy, rigidly maintaining the 'traditional' school values, as everyone keeps endlessly repeating." They were alone now in the school master's...

Four Words Ch. 02

by tom6432 on Sep 11, 2017
Fetish

Elizabeth, my 41 year old wife, sat at her desk in her punishment PJ's. The PJ's consisted of a one piece Dr. Denton footed sleeper complete with a drop seat. The zipper ran down the front all the way to her drop seat flap for easy access. It fit her snugly accenting her fantastic figure. It was a white outfit trimmed with pink and Disney characters on the f...

Maragana Girl Ch. 08

by caligula97236 on Sep 14, 2017
Novels and Novellas

Chapter 8 – Eloisa The weather quickly changed a couple of days after Kim's birthday. Cold rain and sleet constantly bombarded the dreary streets of Danube City, with the promise that there would be no let-up until next spring. The pavement was covered with cold water and the last of the bicyclists were driven off the streets and into the city's trolleys. T...

Return to "Weekend School" Ch. 14

by cynthiablaine7 on Oct 26, 2020
Transgender & Crossdressers

[This story involves bodily functions and sometimes severe disciplining, including caning and spanking, as well as crossdressing. If reading about those offends you, read no further. These stories may be read separately but do gain from being read in sequence.] Laura Franklin wasn't sure what kind of response she would receive when she sent out notices by m...