Stories Of Schoolboy Caned Naked By Headmistress Stories

368,932 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

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...

Appointment by Card Only Ch. 05

by Sputnik57 on Sep 17, 2017
BDSM

Madam Clara did not just have Lucy attend her 'classroom' that day; the soft ginger girl was made to stand in the corner facing the walls while other 'pupils' were brought to attend. Such was the wealthy woman's lust for her kink as the domineering schoolmistress, she had also paid for three males to attend her 'class' that day; each deeply submissive male h...

A Sissy Saga Ch. 18

by Snurge on Sep 15, 2017
Novels and Novellas

Miriam observed the assessor from the Historic Buildings Commission with a measure of disapproval. When he'd first arrived she'd believed her luck had changed and he was about to reverse a previous decision and tell her that financial help was about to arrive by way of a grant. That was not what had happened. "I was on my way to Chance Hall," rumbled Mr Cra...

A Visit to the Headmistress

by adoration on Sep 14, 2017
BDSM

I was 25 and randy, but I was also curious. Well, they say curiosity killed the cat, but in my case curiosity got me the cat. I'd better explain. It was about five years ago and I was just coming off a torrid affair with a lovely colleague, who had dumped me for a much older man, the bastard! The older man, not the lovely colleague. Sandra said that while...

Mrs. Shepherd Learns To Dominate

by harryflashman1970 on Sep 14, 2017
Group Sex

This is another sequel to and Observed Threesome and Foursome. This tale just about stands alone, but I think it'd be more instructive (and would be more arousing) to read the earlier stories. This story picks up immediately from An Observed Foursome before going off in another direction. Thanks again, for the comments, messages and ratings. It's very nice...

Naughty Naomi Ch. 04

by toocold on Sep 19, 2017
Fetish

This has been much-delayed and is only half complete so is shorter than previous chapters but positive feedback for part 3 wanted more and wanted dirty, so toilet action follows - you're warned if that's not your thing. I hope to get back into the swing with this, if I have time. Everyone's legal age and consenting and in my imagination anyways... All thre...

Twelve Days a Slave Ch. 05

by The_Technician on Sep 14, 2017
BDSM

= = = = = = = = = = = = = = = = = = = = Slave missy learns there is more than one kind of spanking. 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 NO...

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...

A Sissy Saga Ch. 16

by Snurge on Sep 15, 2017
Novels and Novellas

It was after supper, but the evening sun still shone through the lofty windows of the gymnasium to catch dust particles floated weightlessly in its slanting streams of light. A naked young man who promoted the delicate aura of a fragile girl stood fumbling over his words before the seated figure of Miss Twist, groping helplessly for an excuse to explain the...

Mother Knows Best Ch. 01

by Sputnik57 on Sep 12, 2017
BDSM

Once again he had arrived at mother-in-law's house; the sneering 60 year old woman, plump and still very attractive, assertive and supremely confident, laughed as she accepted the key to his cock cage from her equally dominant daughter, who left with her lover for Vegas for a week. Rex's cock stirred in its tight confinement as it always did when he was lef...