This book contains the following five fictional stories depicting the corporal punishment of schoolgirls:

The Boarding School Snitch: When Charlotte is sent to the Headmaster for a caning, she decides to make a deal with him: she will snitch on her fellow pupils in exchange for being let off her own punishment. Her spying begins which results in multiple girls being severely caned and she is delighted. That is, until her secret is discovered and payback is due...

Caught Cutting Class: When Amy and Susan go along with their friend Haley's plan to skip class they end up getting caught and sent to the Principal. All three girls soon discover just how painful and effective his paddle can be.

I Have an Appointment for a Caning: After her mother remarries, Susan is quickly bundled off to boarding school, away from her friends, with only rare contact with home. When her mother forgets her birthday she is upset and takes it out on her teacher who sends her to the Headmaster for a caning. It's not all bad news, though, as the Headmaster's elderly secretary takes her for a belated birthday dinner afterwards.

School Essay Revision Session: When Shelby's essay gets a poor grade she must report to Mr Duffy's cottage on campus. Here she is given a chance to resubmit her essay but there's a steep price to pay, with her bare bottom subjected to four strokes of the cane for lateness, followed by several blows from a thick wooden ruler for each mistake she has made.

The Weekend Monitor: Though not the heights of academia that Phillip Caulder had aimed for as a young man, teaching at St. Miriam's Boarding School provides the opportunity to develop his corporal punishment skills. Catching five girls off campus, he administers the strap, but for Dana and Trish the strapping is a battle of wills with their teacher.