Headmistress Spanking Stories

23,089 results
Orientation
Length
Source
Infinite Scroll

Emily's Punishment

by Marialouise11 on Sep 15, 2017
Transsexuals & Crossdressers

Today I am wearing a white long-sleeved satin blouse, a dark blue knee-length skirt, sheer black stockings and dark blue court shoes with 3" heels. My long, dark hair cascades over my shoulders and down my back. My make-up is perfect and I must admit that I feel fantastic. There is a knock at the door. I pretend to be studying the report in the folder. Here...

Hot for Teacher

by Dirty_Deeds on Sep 12, 2017
BDSM

You lean over, "Marie, isn't Mr. Roth hot?" Marie smiles at you. "Is there something you'd like to share with the class, Lizzy?" "No sir." "No? Perhaps you should visit the Headmistress, then." "Yes sir." You bow your head and stand up. As you are leaving the room, you see Mr. Roth pick up the phone on his desk. You knock at the door to Headmistress Do...

The Diary of Jewel Delacroix Ch. 24

by BJGoodhead on Jan 20, 2020
Transgender & Crossdressers

The following contains themes of forced feminization, reluctance, non-consent, and other adult topics, so before we begin here are the usual disclaimers. This is porn, you must be over 18 to read this. If not, go away and come back when you are old enough. If you are old enough and this style of erotica isn't to your liking, then go find some erotica that is...

Submissionette 01: Slaves & Novices

by leersummer on Sep 19, 2017
BDSM

It was still the early morning hour of the day of her first submission, but Mirabella Lucinda was already awake. She lay in her bed wrapped in her linens, watching the rising sunlight through drawn, heavy curtains. Soon, the birds would begin to chirp, followed by the foot traffic that always passed just below her bedroom window. It was a small bedroom, and...

Return to "Weekend School" Ch. 07

by cynthiablaine7 on Sep 14, 2017
BDSM

[This is part of a series, and you likely will enjoy it more if you have read the earlier installments, but it is not critical to read them. There is some limited reference to bodily functions so those offended by such mention should read no further. All characters are over 18.] * Deirdre Carmody was enjoying her visit to her niece Laura Franklin's weekend...

Adventures in Nemesisland Ch. 07

by SlaveNano on Oct 13, 2017
BDSM

The hare led Kim away from the tea party. Kim was told to take off her fetish 'Alice' dress and change into some new clothes. The hare, or the Duchess, as she saw her, helped Kim tie her hair into plaits and get dressed. This time Kim had to put on baggy navy knickers, a grey skirt, a white cotton blouse and a purple and black striped tie with grey socks and...

Dedeaux's Delightful Discipline

by lesliejones on Sep 18, 2017
Reviews & Essays

Review: Dedeaux's Delightful Disciplinary Tales THOSE who delight in sophisticated yet incredibly arousing tales of delicious discipline have long been entranced by the novels of the mysterious P. N. Dedeaux. The eclectic author set his scenes in Europe—both present-day and historically—as well as Canada and sometimes unidentified exotic locales. While man...

SSCG Ch. 05

by Crystal_Ash on Sep 16, 2017
BDSM

Chapter 5 -- A Hunch About Lunch The school day was finished, much to Jenny and Sarah's relief, and it was time for lunch. On the way to the dining hall, a question surfaced in Sarah's mind. "I wonder whether there will be anything out of the ordinary about lunch?" she asked her companion, "After all, look at the classes. I have a hunch about lunch; someth...

Taken by Miss Strokewell

by Tyrnavos on Feb 13, 2018
BDSM

Elizabeth Strokewell is a dominatrix who specialises in dominating older gentleman. She has a story here on Literotica (https://www.literotica.com/s/dental-nurse). The personality that comes across in her story is vivid and amusing, and I started wondering how a chance encounter between her and a less experienced gentleman might turn out. The following story...

The Desk Ch. 02

by fishophile on Sep 16, 2017
BDSM

[Note: This is a follow-up to "The Desk". Read that first if you haven't done so already.] 1 Chloe walked nervously up the garden path. It was a detached house on the edge of town, in one of the nicer suburbs. Despite the sunshine, she was glad of the long coat which kept away the breeze that whistled through the trees. And, of course, it also was glad th...