School Caning Stories

106,204 results
Orientation
Length
Source
Infinite Scroll

Cunt Caning Carnival Ch. 02

by AlphaBeatHer on Sep 12, 2017
BDSM

Henry's head was swirling from a mixture of champagne and the heady delights of cumming twice into Sheila's throat with Serva's tongue up his ass. Tom called to him to throw the dice for Richard. Taking the dice from Tom, Henry threw them onto his side table. A four and a three. Richard looked a little disappointed as Tom called out. "Seven minutes." He wa...

Assessment by Archana

by cyrusbharucha on Jul 13, 2020
BDSM

Tarekh was always very nervous when he reported to Miss Archana for his college tuition. A caning was inevitable. After all, that's why he went. But he had no reason to be any more nervous as he pressed the doorbell this time, apart from that the strange craving inside him seemed stronger than usual. Little was he to know that Miss Archana was also in an unu...

Clara Bow's Academy for Ladies

by Sputnik57 on Sep 15, 2017
Transsexuals & Crossdressers

Peter had had no choice in the matter from an early age. As he car drew up to the huge ivy clad castle-like building, having entered through electronic gates in a ten foot wall, he felt doomed yet excited. His cock was erect in the tight panties his Stepmother has chosen for his introduction, his anus tingled and gripped the soft rubber plug she'd also chose...

Owned by my Mother-in-Law Ch. 07

by Sputnik57 on Sep 13, 2017
BDSM

I was released from the haven of my mistress' crotch and she stood by me in a central position, flexing her cane in readiness for my punishment as we watched the gimp's misery. The wickedly pencil-skirted headmistress that was Arabella, placed the black dish from earlier at her feet, and ordered the gimp down to it in full view of the eager crowd of women. A...

The Party's Ripe for Caning Ch. 04

by lesliejones on Sep 19, 2017
Fetish

This story does involve bodily functions and humiliations so those offended by these topics should read no further. All characters are 18 or over. ***** Linda Crawford noticed that student behavior in her classes—both the majority, which were all boys, and the one all-girls class—seemed much improved of late with all pupils very careful to avoid being seen...

Twelve Days a Slave Ch. 12

by The_Technician on Sep 14, 2017
BDSM

This is the story of a young woman's conviction as a terrorist and what happens to her when she is sentenced to penal slavery. Penal slavery is not impossible. The Thirteenth and Fourteenth Amendments to the Constitution of the United States of America do NOT prohibit slavery. They only LIMIT slavery to punishment for crimes. In other words, the Constitution...

Class Monitor Gets to Cane

by lesliejones on Sep 12, 2017
Fetish

Anne Smithers, who had taught English for a few years, was slightly surprised when the young principal at St Kendras Finishing School called her in to discuss a new idea Miss Crawford had. Anne liked Penny Crawford, who shared Anne's own ideas on maintaining as strict discipline as possible without being able to touch the pupils. Penny told her that she th...

Twelve Days a Slave Ch. 06

by The_Technician on Sep 14, 2017
BDSM

This is the story of a young woman's conviction as a terrorist and what happens to her when she is sentenced to penal slavery. Penal slavery is not impossible. The Thirteenth and Fourteenth Amendments to the Constitution of the United States of America do NOT prohibit slavery. They only LIMIT slavery to punishment for crimes. In other words, the Constitution...

The Domme's Boyfriend

by lesliejones on Sep 12, 2017
BDSM

[This is a story in a series that chronicles Karen's development as a domme. All characters and recollections of events involve characters who are 18 years of age or older. Some bodily functions are involved, so those who dislike that should stop here.] * Karen's boyfriend Rod had been extra attentive to all of her desires ever since she had disciplined h...

Jessica at the Finishing School Pt. 04

by MALIBUMAN666 on Sep 25, 2017
Fetish

This story was written in 2000, annoyingly I am having to transcribe it from a physical copy since that is all I have available. I hope you enjoy it and you think it worth my efforts. This is part four of five, since the feedback has been largely positive I am cracking on with the rewriting/transcribing and the last part should be done very soon. I'm postin...