Headmistress Spanking Stories

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Infinite Scroll

A Sissy in the 22nd Century

by JerkGently on Jul 1, 2020
Transsexual

In a future not too far flung, humanity has progressed to a stage where almost all production and provision of society’s needs is automated. With no need to work, all citizens are instead driven to find lifestyles that fulfil their own and each other’s fundamental desires. This is achieved by the medium of an overruling system of artificial intelligences and...

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Schooling the Stepford Husband Ch. 02

by jane marwood on Sep 25, 2017
Fetish

Constance Marchbank sat behind the large modern desk of the medical office. The room was decorated in a traditional style, rather like an old fashioned doctor's surgery. The Adam fireplace was the centrepiece of the room, giving it an easy and comfortable air. Mahogany bookcases surrounded the walls of the well-lit room, with a heavy pastel-shaded carpet co...

Combatting Clenching

by lesliejones on Sep 12, 2017
How To

To Dearest Lizbeth * Experienced disciplinarians are familiar with the behavior known as clenching. The person being spanked, caned, or paddled seeks to press his or her buttocks close together in a vain attempt to avoid the pain that is inevitably coming. The dominant finds clenching annoying because it may affect the accuracy of the cane or brush stroke....

The Girls College Ch. 09

by TF2123 on Jul 31, 2018
Fetish

The sun had risen over London, birds were excitedly chirping as many people started their daily commute. It was Wednesday the sixth of September, the summer holidays were over. As the bright rays of sunlight kissed the glistening windows of London Girls' College for the first time that day, Paul Edwards was already wide awake. He had been, quite rudely, awo...

The Desk Ch. 04

by fishophile on Sep 16, 2017
BDSM

[Thanks to A for editing] 1] The ironing board in the kitchen was exactly the wrong height - or the right height depending on how one looked at it. Chloe tried to ignore it, but it meant she had to stretch her arms out further to press Mrs Petrescu's clothes; a task she usually performed with relish, eager to earn her Headmistress, manager and Ma'am's appr...

Mrs. Shepherd Learns To Dominate

by harryflashman1970 on Sep 14, 2017
Group Sex

This is another sequel to and Observed Threesome and Foursome. This tale just about stands alone, but I think it'd be more instructive (and would be more arousing) to read the earlier stories. This story picks up immediately from An Observed Foursome before going off in another direction. Thanks again, for the comments, messages and ratings. It's very nice...

SOAR University Ch. 01

by AubreyWright on Sep 14, 2017
First Time

Izanagi dropped his backpack next to a desk in the back row. Low profile, he thought to himself. That's how he got through secondary school, and as his first day at university, why should that be any different? But, it would be different. Different for Izanagi and, he had to keep reminding himself, for everyone else, too. This was university, and not just...

The Girls College Ch. 08

by TF2123 on Jan 13, 2018
Fetish

Brooke Johnson was a beautiful woman. Her face was pretty and she had long, soft blonde hair that was propped up into a very tight bun. She had large breasts, yet a thin waistline. Her firm bottom was covered by a black Ponte-knit pencil skirt that stopped just above her knees. Sheer, glossy pantyhose matched her milky skin tone and ran down to her feet, dre...

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...

The Appointment

by LongJoe on Sep 1, 2017
Humor & Satire

Mrs Olivia Williams, twenty seven years old, married to Roderick Williams, forty one years old and highly successful, wealthy banker, pulled her car up outside the address she had written on the back of a rolled up railway ticket. She sat for a moment and stared at the anonymous building that contained the address she was about to enter. She considered not...