Headmistress Schoolboy Spanking Stories

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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...

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...

Femdom Nihon Date Ch. 1

by chenwanli on Sep 12, 2017
BDSM

I hate setups. Blind dates are the worst. Tom and his wife Yumi had set me up with a couple of her friends and classmates from Japan if they moved or came to San Francisco but none of them were even remotely my type- they all wanted to do whatever I wanted, had no opinions of their own, and giggled ceaselessly. I let my friends know that they really shouldn’...

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...

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...

Return to "Weekend School" Ch. 11

by cynthiablaine7 on May 29, 2018
Fetish

Laura Franklin's weekend school was proving so successful that she was now scheduling weekend sessions twice a month. Laura aimed at middle-aged adults who longed to return to the strict discipline they had likely experienced back in their own school days when caning and spanking were common. She had recruited one of her old teachers, Melody Haynes, who was...

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,...

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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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...