Headmistress Spanking Stories

23,089 results
Orientation
Length
Source
Infinite Scroll

Back to School Ch. 01

by good little boy30 on Sep 16, 2017
Transsexuals & Crossdressers

All the teachers in this story are based on teachers from my own school. If any of you ladies ever read this I would love to hear from you and promise to be a good little boy for you. Graham sped down the country lane, roof off, Led Zeppelin on the CD player, enjoying the Lotus for what may be the last time for a while, the sun was shining and he was thrill...

When Angels Cum Ch. 15

by CapDragon121 on May 7, 2019
Sci-Fi & Fantasy

Author's Note: I apologize for the late chapter. It's been a busy time for both me and my editor. Chapter Edited by the extraordinary Alex Lawrence aka DankMemez. Looking for Editors: Dankmemez has been helping me edit since chapter 11. He has been massively instrumental in my improvement and has put his heart into editing my work. Unfortunately, he cann...

Return to "Weekend School" Ch. 11

by cynthiablaine7 on May 29, 2018
Fetish

Laura Franklin's weekend school was proving so successful that she was now scheduling weekend sessions twice a month. Laura aimed at middle-aged adults who longed to return to the strict discipline they had likely experienced back in their own school days when caning and spanking were common. She had recruited one of her old teachers, Melody Haynes, who was...

Fox in the Henhouse

by Shandy on Sep 26, 2017
Amateur

Note: Due to numerous requests, pictures of some of the main characters can be found here: https://chyoa.com/chapter/Pictures.407721 Pink Rose Academy is one of the most prestigious private schools for girls in the country. Established over a century ago, it has long been a place where the very wealthy sent their daughters for education and preparation for c...

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Ms. Greys' School Ch. 02

by Lydyia on Sep 15, 2017
Transsexuals & Crossdressers

Chapter 2: New student written LJP edited another wannabe Preface: This school is for young women(18-20) and is focused on helping young trans women with their transition. Also I would like to thank my Editor for all his help. * Fall was here, the leaves were turning and the air was crisp. Time for the start of a new school year at Ms. Grey's. The camp...

Mistress Kathy's Wicked Protégé Ch. 05

by ThoughtStorm on Sep 15, 2017
BDSM

A private yacht was moored at a private dock on a private beach at the westward end of a very private estate. Nearby an expensive car reached the end of the private road and pulled into a lot facing the dock. A rear door opened, and one of the world's most recognizable women stepped out to have a look. Della Tiara swept back her perfect curls, revealing smo...

Lions of Parnatha Ch. 01

by Medievna on Sep 12, 2017
Sci-Fi & Fantasy

It was a moment I had hoped would never come, one I had dreaded for years. In my mind there was no greater threat, not pain of death or facing the wrath of the gods themselves, nothing at all that could bear such fear within my soul. In that moment, all dreams became delusions and all hope was lost. In that moment, my fate, a life of servitude to the will of...

Cybil is Seeking a New Slave Ch. 02

by lateknew on Jul 6, 2020
BDSM

Story is about consensual adults starting a bdsm relationship F/m. For whoever read ch.1, Cybil has taken the first step into getting him to agree in being a slave to her. She is waiting for Sean to get back to her giving his agreement or final agreement and take the vows if he is ready. Once again I sincerely thank Mistress4one who has edited this story....

Kinktober 2020 - Day 02

by QuinnWitchy on Oct 12, 2020
Sci-Fi & Fantasy

{As I was editing this, I realized I should've done it differently, with Quinn trying to keep the attention of someone who was distracted. It would've had a lot more sex in it that way, being in Quinn's head and all, and doing it this way means she's the distracted one...but I really wanted to try writing something with a bit more of a femdom vibe to it. Her...

Belinda & Alberta Strip

by lancelot on Aug 30, 2017
Exhibitionist & Voyeur

Rod had another stag approaching and he was to be the organizer this time; and he didn't want any of the mistakes to occur that happened at the last stag organized by a friend. So I'd better let Rod take over the story at this point because my role was more participatory and the view of what happened would be better coming from a voyeur, as it were. Well, B...