Headmistress Stories

651 results
Orientation
Length
Source
Infinite Scroll

Cumming In My Wife's Best Friend Ch. 04

by HornyHubbie on Sep 18, 2017
Loving Wives

IF ANYONE HAS NOT READ PARTS 1 TO 3, I WOULD HIGHLY RECOMMEND THAT YOU READ THESE BEFORE READING THIS CHAPTER. I THINK YOU WILL ENJOY THIS CHAPTER A LOT MORE IF YOU HAVE THE FULL BACKGROUND TO THE CHARACTERS AND THE STORY. **************** The phone at my desk rang for what must have been the twentieth time, and it was clear that the person on the other en...

Hearts Academy Ch. 01

by RoseB on Oct 7, 2019
Transgender & Crossdressers

Disclaimer and Notes: Disclaimer and Notes: Hearts Academy is an dark horror/mystery story focusing on the reluctant feminization of a young artist. There are many themes such that cause it to be disturbing for those who cannot handle terror or dread well. This is a sequel to The Rose Diaries. While the characters are brand new, it does reference events an...

Repercussions Pt. 01

by astushkin on Jul 29, 2019
Romance

Derbyshire, England, Spring 1854 Chloe She never would have dreamt that she would miss her time at finishing school. One week returned home from Haversham Academy, Chloe stood upon a rocky outcropping gazing with a disquieted feeling down over her family's estate. Nigh a mile distant she saw Greystoke Hall favorably situated upon a gentle rise in the land...

Shemale Surprise

by silkstockingslover on Oct 21, 2019
Transgender & Crossdressers

SUMMARY: A married man is seduced and taken by a friend of his wife's. EDITING THANKS: Thanks to Robert, goamz86 and MAB7991. NOTE: This story is dedicated to Robert who requested the fantasy...sorry but the story ended up a lot longer than originally planned. ***** "You can stay with Robert if you wish," Mary said on the phone. I looked up from my lapt...

Anne & Coco

by G-String on Sep 13, 2017
Exhibitionist & Voyeur

I arrived at the bus terminal on Hong Kong Island side just after 7:00 am. I was only a few minutes late but they should have waited for me. Well, I wasn't sure if I really wanted to go anyway! Gave me the creeps just thinking about the trip. Perhaps this was my perfect way out. Sod it! Sod them all! "Coco." An unfamiliar voice called me from behind just as...

Boarding

by VMKane on Sep 14, 2017
BDSM

(As always, my thanks go to Lisa Jones for advice and encouragement with this story.) Abi stood on the corner and thanked her lucky stars that it was mid-afternoon rather than night. A couple walked past, intent on their own business, but even so she found herself checking her watch and looking impatient. See that, look at me being huffy; because I'm wond...

In Mrs. Reilly's Garden

by aaronburr on Mar 13, 2018
Exhibitionist & Voyeur

This story follows Rodney's Nude Humiliation Cpt 14 and Days of the Raj. If you like CFNM I am sure it will appeal to you. ***** In the warming sun of a mid-Western summer, in a grove of Mrs Reilly's garden framed by trellises and rose shrubs, the well-dressed ladies milled about. It was one of the finest gardens in the mid-West and the ladies presented a...

Tales a Swinger Told Me

by Shadowlands on Sep 12, 2017
Group Sex

This is based on a true story. It was told to me by friends and some time swinging partners. The actual detailed descriptions are figments of my imagination. The plot is entirely true. To those of you who choose to comment disparagingly about husbands who allow their wives to have sex with other men I say this. Eat your heart out ... * I have been married...

Unspoken Exchanges

by JackRace on Sep 14, 2017
Erotic Couplings

CHAPTER 1 Friends and family thought it funny. And strange. They still do. But we loved that peaceful North Wales coastal resort and had been taking our breaks here since we married 22 years before. It had a lot to offer us. For me it was the hill walking nearby and great stretches of shoreline to run to my heart's content. For Kate my wife, there wa...

Like Father Like Son Ch. 03

by smilodonwriter on Sep 16, 2017
Novels and Novellas

July 1916 Bethan Phillip was reluctant to send a telegram home to announce his unexpected arrival: the appearance of the telegram boy was viewed as an ill omen now at home. This would be particularly the case with the battle raging across in France. He had heard that over sixty thousand British and Empire soldiers had died on that first morning as he watc...