Headmistress Spanking Stories

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Orientation
Length
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Infinite Scroll

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...

Mrs Johnson's Opening Gambit

by adoration on Sep 1, 2017
First Time

It was 10 years ago now, but I can remember every sight, sound and smell of that incredible week-end. Mum had to go up to London for reasons she never explained and while I was 18-years-old I was still very much a "mummy's boy". Crikey, have I grown up! Anyway, mum called over the back yard fence and our neighbour, Mrs Johnson came out and walked down her g...

Pamela Ch. 05: Lights Camera Action

by FrankMcMahon691 on Jun 12, 2019
Group Sex

Hi Thank you to everyone who has read some or all of my attempts to chronicle Pamela's adventures - it really is appreciated, whether you voted or not (but even more so if you did!). This is chapter five, which means, as each chapter covers a full day from midnight to midnight and we started on a Friday, it's now Tuesday and Pamela is ... well, I don't kno...

Weekend Fantasy Ch. 01

by fantasywriter4all on Sep 17, 2017
BDSM

I'm Pat, a retired headmistress who never married. On alternate Saturday mornings Jason who is now 20 comes to clean. He is one of a group of university students who just charge minimum wage rates. When the doorbell rings I get up, slip on a short dressing gown, open the door and let him in. He slips off his coat and hangs it up. He is a Scottish lad and wea...

Naughty Naomi Ch. 04

by toocold on Sep 19, 2017
Fetish

This has been much-delayed and is only half complete so is shorter than previous chapters but positive feedback for part 3 wanted more and wanted dirty, so toilet action follows - you're warned if that's not your thing. I hope to get back into the swing with this, if I have time. Everyone's legal age and consenting and in my imagination anyways... All thre...

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...

Headmistress

by LeanneSinclair on Sep 13, 2017
BDSM

The school and university system of England is a strange, anomaly-ridden thing. It has grown up haphazardly over centuries, subject to the caprices of tradition and political whim, baffling to the outsider. One of the anomalies is that the great medieval universities of Oxford and Cambridge (collectively "Oxbridge") select part of their student intake on the...

Finishing School Handbook

by brewster926 on Sep 16, 2017
Humor & Satire

Please note: this is an official copy of the handbook actually used at Dr. Deucel's famous finishing school which was in existence in Wayward on the Tool in Lower Suckexx during the latter part of the Nineteenth Century. Dr. Deucel's school was known for taking ladies in their twenties and older that everyone else had given up on and helping them become happ...

Miss Is in Pain

by MistressAndromeda on Sep 17, 2017
BDSM

I assumed my position over her knee, her skirt slick over stockinged thighs. She pressed her forearm to my back, her hand nestled in my armpit, close to my breast...my gaze slipped downwards, taking in sheer black hosiery and blood red heels. "You're a bad girl, and bad girls must be punished!" Andromeda chided as her hand swung back and she launched her han...

Sehnsucht Ch. 04: Consequences

by ladythisbe on Apr 3, 2018
Novels and Novellas

Down to the laundry with the suit in hand, I find myself smiling at the secret mischief I pulled with it the night before. I promptly head to the kitchen, grab a quick bite to eat, and get items prepared for breakfast. The drab staff is just having their usual banter but after yesterday I feel a changed woman. The breakfast bell summons me, and I do a quick...