Schoolgirl Caning Stories

8,898 results
Orientation
Length
Source
Infinite Scroll

Wishes Can Be Dangerous

by Too-Kay on Sep 13, 2017
BDSM

A Cautionary Fantasy Having finished my latest erotic novel, I put the book down and sighed, "I wonder what it would be like to be fucked and whipped or beaten and fucked again and again - all the while being strapped so I couldn't get away. I wish it could happen to me like in that book." Although I was naked, I wasn't cold, and I rubbed my pussy as I p...

The Roommate Pt. 12 - Miranda

by ValoryG on Sep 19, 2017
Transsexuals & Crossdressers

Chastened, Josh/Lori nursed her wounds for days, and little was said between her and Miranda, except when the dominant asked how Lori had opened her chastity when with Cassie. "I bought a master key on the Internet," answered Lori brightly. "Actually, my penis is getting a little irritated by the plastic over such a long time." "Give me the key. It obvious...

A Very Shameful Punishment Ch. 03

by lesliejones on Sep 12, 2017
BDSM

This story will benefit from prior reading of two previous chapters. It amplifies events that occurred in Chapter 02. * Eleanor's punishment and the hearing that was held in the District Court of the Women's Republic when she was scheduled to complete her sentence did attract some public attention. There had been few cases of adultery in the republic in re...

My Story Ch. 03

by thehotness on Sep 17, 2017
Exhibitionist & Voyeur

(The last part of this story is based on real life. In 2001, a schoolgirl was held 17 days in a small flat and sexually tortured by her supposed friends. Inept torturing led to more pain then pleasure and the girl ended up with severe 2nd and 3rd degree burns that required reconstructive surgery. It was a horrific thing, and I sincerely hope that this never...

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...

Jolene's Momma Pt. 02

by ValoryG on Oct 6, 2020
Transgender & Crossdressers

After Brandi left, after I had willingly signed my privileged life away, I also had some nagging fears. Like, would Jolene be able to carry out her role, since she was usually so sweet and caring, and she usually gave in to what I wanted? Or would she take after her mom and become a merciless taskmaster and sadist whom I would hardly recognize? After we ha...

Twelve Days a Slave Ch. 10

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...

First Interlude

by tovesslithy on Sep 14, 2017
BDSM

24 First Interlude Helen Shagton was forty-two years old. Despite this very adult age, she was nursing a very recently and well-caned bottom. She was just returning home by car. However, she had felt, as she so often did, that she really needed a good, hard, school caning style punishment herself. The Headmaster, had, naturally, been very happy to oblige h...

The Cane, Thank You Mistress

by thomstevens on Nov 30, 2017
BDSM

I make my way down 28th Street in Midtown Manhattan, weaving though the lunchtime crowds that flow in streams and eddies along the sidewalks. The street is jammed with taxis, cars, and delivery trucks. I walk slower than I usually would, not wanting to be either late or early for my appointment. Just beyond 6th Avenue, I stop before an unmarked gray door, ch...

Owned by my Mother-in-Law Ch. 03

by Sputnik57 on Sep 13, 2017
BDSM

Despite having emptied my balls, my cock was soon stiff once more as I duly licked Blanche's sticky, and now a little stinky, pussy clean; she made me do such a thorough job, I was not released until she had achieved a second orgasm at my expense. The realisation that she was going to receive this service for at least a fortnight, and she was to start by can...