Headmistress Spanking Stories

23,089 results
Orientation
Length
Source
Infinite Scroll

David's Tall Girls' School Ch. 11

by Thorilla on Sep 19, 2017
Fetish

(It was late autumn of 1960 and I, David Shaw, was 20 years old and was following my hobby of bird watching. I had unfortunately been detained by Amelia Wiff-Naseford, headmistress, for being an alleged 'Peeping Tom' in the grounds of 'Dentwood Finishing School for Tall Girls aged 18 to 20 years old'. There were 120 girls registered at the school. Clearly I...

The Boys and Girls are Watching Ch. 07

by Alfamann on Sep 16, 2017
Exhibitionist & Voyeur

Despite the fact I had needed to punish Francesca for having the packet of cigarettes in the house, I was actually feeling very confident she was over the worse of her addictive tendencies, particularly the alcoholism which was by far the greater worry. It had been several weeks without any major issues and I was actually feeling pretty damn smug that my hig...

Escape From Monster Island

by hematoma on Dec 10, 2011
Fantasy

The Paisley School for Extraordinary Girls in London is the finest college for the world's most talented ladies. Some of the young women studying there are great muscians, some are geniuses or athletes. Other girls have peculiar talents and find their way to the Incredible Arts Department. Here, Headmistress Victoria Swift teaches her young pupils the most i...

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Teaching Practice

by LaurelAspen on Jul 25, 2018
BDSM

"I'm very disappointed..." Caroline strides around her office looking accusingly at the flustered figure hovering in the doorway. Mature student Maggie is imprudently late for her teaching practice evaluation. She's yet to discover her tardy timekeeping is, on this occasion, forgivable, at least as far as her headmistress is concerned. Goodness knows it's ha...

David's Tall Girls' School Ch. 06

by Thorilla on Sep 19, 2017
Fetish

(It was late autumn of 1960 and I was 20 years old and was following my hobby of bird watching. I had unfortunately been detained by Amelia Wiff-Naseford, headmistress, for being a Peeping Tom in the grounds of 'Dentwood Finishing School for Tall Girls aged 18 to 20 years old'. There were 120 girls registered at the school. I had decided not to get the pol...

Schoolgirl Visits the Doctor Ch. 03

by brandi_blue on Sep 21, 2020
Group Sex

It had been one week since my initial appointment with Dr. Simmons and it was time for my follow up. After the events of the week, I was a little nervous about what was to come. I arrived at the doctor's office in the same outfit as last time -- schoolgirl slutty with pigtails -- only this time I was wearing a white thong under my skirt instead of the full w...

Sex Academy Ch. 01

by adia_23 on Sep 12, 2017
BDSM

I am shaken awake by the headmistress around noon. My eyes slowly adjust to the light as she says, "Hurry, get up. Your master wants you to be ready to go out tonight at 9:00." Yawning, I slip out of bed and walk fully naked down the hall to the showers, my nipples tautening in the brisk air of the hallway. Ginny, a petite blonde first-year student, is strid...

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...

Across The Water Ch. 01

by HarleyR on Sep 16, 2017
Novels and Novellas

This is a story that came to mind while I was daydreaming at school. The main characters are 17 as the story begins, but will be 18 before anything sexual begins. In a way it's kind of a coming of age type of story. There will be same sex attraction, experimentation, love, lust, and an interesting love triangle that will cause all kinds of angst and conflict...

After the Ball

by barabajagal001 on Sep 13, 2017
Erotic Couplings

Notes: (1) The main male character's name is Caelum, intended to be pronounced "Ky-lum." (2) This is the first time I have tried to write in quite this style, so I apologize in advance if any of it comes off sounding silly instead of sexy. (3) I do take a bit of time coming to the point, but I promise we do get there in the end. ***** A sea of adolescent g...