Headmistress Spanking Stories

23,089 results
Orientation
Length
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Infinite Scroll

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...

A Song for Lara Ch. 02

by dan57 on Sep 19, 2017
Loving Wives

By Dan57 and Lara Lara shut down her computer and thought back to her email exchanges with Dan57. He had liked the pictures she had sent him but wanted her to send more explicit ones. She had cupped her breasts in her hands as he had told her but she had turned sideways so the light had been dimmed and her nipples were hard to delineate. Dan had promised...

Spanking For A Schoolgirl

by tralaw on Sep 4, 2010
Fetish

Melanie knew she had been naughty. As she sat in the Headmistress's office, she played with the hem of her skirt and listened. From behind the door, she could hear the sound of a very bad girl crying and the rythmic fall of something heavy falling onto soft skin. Her butt tingled. She knew that she and Lauren shouldn't have done it. I mean really, who in the...

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Managing Melanie

by kinkqueen on Sep 15, 2017
BDSM

Janet was 43. She'd been a widow for more than two years, and for all of that time she realized how hopelessly incapable she was of controlling the misbehavior of her only child, her daughter Melanie. Janet's late husband had tried to discipline the girl, by grounding her and cutting off her allowance, but he'd had little success. And then Janet, on her own,...

A sissy visits the Headmistress

by maturesubmale_for_F on May 12, 2020
Transgender & Crossdressers

1. Miss Stern delivers both punishment and pleasure I knocked timidly on the heavy door and heard Miss Stern's voice from within, commanding me to enter. I slowly opened the door and walked into the presence of my Headmistress. She was in her mid-fifties and sat behind her massive oaken desk as I came in, studying a heavy file. I stood still just inside the...

Long Term Nudity Project 2035

by zoejoey on Sep 14, 2017
BDSM

Hi folks, Zoe here. I recently submitted a story in Exhibitionist/Voyeur called the 'Long Term Nudity Project' right here on Lit and I haven't yet decided whether I will continue with it. However, the scenario has opened my eyes to other interesting possibilities that I would like to explore a little before I make my final decision on continuing with the lad...

The Petworthy Finishing School

by Farinholt777 on Sep 16, 2017
Novels and Novellas

Chapter One Where Mitten is interviewed and examined by the Headmistress. It was a very long trip so Mitten had a long time to think about it. Her Daddy told her that the school she was going to was far away and very strict compared to the little school house in Lincoln. For people in Nebraska, they were very well off. It was the only way that she would b...

Return to "Weekend School" Ch. 06

by cynthiablaine7 on Sep 14, 2017
Fetish

[This story involves principal bodily functions and those offended by them should read no further. It also does feature spanking and other forms of discipline. All charcters are over 18.] Deirdre Carmody took the speed up on the Honda NSX sports car she was driving down to her niece Laura's weekend school. Deirdre had more or less brought Laura up and s...

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...

#4's Auction Pt. 02

by LiseKLord on Sep 19, 2017
BDSM

As the Headmistress had promised the former #4 was prepared for travel the next day. But as she had also promised, the night after her auction had been one of unending pleasure. It began upon entering the Mistress' sumptuous suite. Still in her red catsuit the woman who had owned #4's life during training and now sold her to the highest bidder poured two fl...