Headmistress Stories

651 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 SmutMD.com

The Petworthy Finishing School

by Farinholt777 on Sep 16, 2017
Novels and Novellas

Chapter One Where Mitten is interviewed and examined by the Headmistress. It was a very long trip so Mitten had a long time to think about it. Her Daddy told her that the school she was going to was far away and very strict compared to the little school house in Lincoln. For people in Nebraska, they were very well off. It was the only way that she would b...

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...

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...

RTFM

by astuffedshirt_perv on Sep 26, 2017
Toys & Masturbation

Note: This story takes place in the near future. The toy in this story was inspired by a story on another site, "The Curator," and is used with permission. Google "Streetwalker Squid Stimulator Deluxe with Partner Play" to find it. Karen started to shake in her silken sheets as her orgasm hit. Despite being alone in her apartment, she instinctively grab...

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...

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...