Headmistress Spanking Stories

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Orientation
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Infinite Scroll

Teacher in a Private School

by mixermix on Mar 11, 2013
Romance

"Mr Doe I'd like to offer you the job." The young headmistress tells you. "Brilliant thanks a lot." You answer standing up from the chair. You stand up to shake your new bosses hand and you can already admire her beauty. Her name is Miss Roberts and she is the headmistress of an all Girls Private School. It also has all women teachers. Yo...

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The Sorority

by dgharis on Sep 17, 2017
BDSM

THE SORORITY Naturally she was apprehensive. The sorority had a certain reputation; strict, unforgiving. Still, their girls had the best grade averages on campus, and she wanted the best. If she had to give up some of her personal freedoms, so be it; to have the best job prospects was worth a little sacrifice. She steeled herself and knocked on the door. "...

A Corrections Officer's Tale

by adoration on Sep 13, 2017
BDSM

It all came about because my husband, Roger, and I took in a lodger. She was a lovely young thing, a tall blonde, beautifully built if slightly on the muscular side, and the local girls school's new physical education mistress. I say "school", it was more of a home for wayward girls aged between 18 and 20 years – a place they would be sent to avoid going to...

David's Tall Girls' School Ch. 10

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...

Finishing School For Ladies Ch. 09

by MicheleNylons on Oct 9, 2017
Transsexuals & Crossdressers

Chapter Nine - Teacher Knows Best "Well its back to the grind I suppose," Valerie said sitting down to breakfast with Sally in their Soho flat on the last day of her holiday. "I know you told me that you're effectively still in hiding but I don't know why you have to stay at fucking Saint Trinian's," Sally sounded a little exasperated. "You know its Chelm...

When Angels Cum Ch. 10

by CapDragon121 on Nov 27, 2018
Sci-Fi & Fantasy

Author's Note: Sorry guys, I've been sick for two weeks. Food Poisoning turned into a stomach infection which caused excruciating stomach spasms every ten minutes and lasted for 3 days. 'Twas hell. I think I got a glimpse of how it is to be pregnant. Guess its punishment for messing around with angels? Lol. However, this chapter is extra long so that should...

Innocence Lost Ch. 16

by bradley_stoke on Sep 14, 2017
Novels and Novellas

In Which Gryphon teaches Innocence and Chastity in a college of Further Education; and develops a particular affection for the attractions of Chastity. Gryphon had enjoyed her work as a school-teacher and it was a great disappointment for her when it became clear that she would have to seriously consider a move to another institution - and as there was suc...

Headmistress Oatlash

by The Mutt on Sep 17, 2017
BDSM

Being that it was the last class of the day, and Poetry at that, it was a given that the young gentlemen of the Oatlash Academy would be a bit unruly. Therefore, Headmistress Natasha Oatlash thought it best to teach the class herself. After all, many of her teachers were little older than the 18 year-old boys they taught. Though she felt quite youthful herse...

David's Tall Girls' School Ch. 16

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...

A School for Spanking

by lovethosepanties on Apr 18, 2018
BDSM

As a teacher of 15 years' experience, I suppose I thought I had the right to believe I had seen it all? Well, I certainly thought I had, until, at a crossroads in my life and wondering whether to have a change of career, I saw an advert requiring an English teacher at an all girls finishing school in Switzerland. I nearly didn't read past the headline assumi...