Headmistress Stories

651 results
Orientation
Length
Source
Infinite Scroll

Return to "Weekend School" Ch. 05

by cynthiablaine7 on Sep 14, 2017
BDSM

[This story involves bodily functions as well as discipline, so anyone offended by either should read no further. All characters are over 18.] * It was time for the final assembly at the weekend school. As Melody Haynes and Anne Smithers supervised the pupils, they filed into the large hall where Laura Franklin stood at the lectern on the stage. Laura was...

Infernal

by Sabledrake on Sep 13, 2017
Novels and Novellas

Chapter One – Abigail did not quite run, knowing that if she did one of the other girls might see and wonder what was the matter. She did not run, but she hurried at as fast a walk as she dared, her pulse hammering and a hot flush awash on her face. A repulsive, slippery-warm feeling had taken up residence inside of her, making her skin tingle and her n...

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...

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...

Madame Jenoix

by Candour on Sep 26, 2017
Transsexuals & Crossdressers

Chapter 1 --------- A young looking and slight 18-year-old boy sits outside the Headmistress's room, obviously feeling anxious. His legs kick back and forth under the chair and he keeps looking up at the door. His uniform looks unkempt, like he has just thrown it on after Games. After some long, countless minutes elapse, he hears a loud, slow "Come!" from...

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...