Inspection Headmaster Stories

12,642 results
Orientation
Length
Source
Infinite Scroll

Headmaster

by Astraphemeral on Jul 27, 2018
Amateur

The Venus Academy for Girls is, unfortunately, neither as divine nor as stellar as its name implies. Although once unquestionably the best girl's finishing school in the state for the 18+ woman, it's fallen far from grace. Today, you can see girls doing cocaine in the washrooms, or wearing skirts that end halfway on their calves. Others party late into the n...

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Pakistani Daughter

by StoryTeller07 on Feb 6, 2018
Fetish

A daughter takes over Ayesha was shopping locally with her mother, getting to know the new area. She hoped not to run into anyone from the new school while wearing traditional Pakistani clothes. Although, while wearing an abbaya and head scarf, there wasn't much chance she would be recognised. The clothing completely covered her, leaving just her face parti...

Spanking Headmaster

by BostonDom55 on Sep 14, 2017
Fetish

Please note, all parties involved are over 18. * You are a student at the age of consent, dressed in a white blouse, lacy white bra, pleated short skirt, no panties, and white socks. You have been called in to my office because you have been under suspicion of smoking and even worse, of possible sexual activities, with boys and girls. I am the Headmaster...

Melissa's Story Ch. 02

by iraussieguy on Sep 13, 2017
BDSM

Author's note: This is the continuation of "Melissa's Story Ch. 01" - if you have not read it, I suggest you do before reading "The Schoolroom". Many thanks to all my fans, specially M, R & A, for their positive feedback. Melissa's story continues: Chapter 2: The Schoolroom Driving home from Matt's after my first spanking session I felt as if I was in an...

Finishing School For Ladies Ch. 11

by MicheleNylons on Oct 9, 2017
Transsexuals & Crossdressers

The finale...enjoy. * Chapter Eleven - Business As Usual The businessman sat in his cheap London hotel room sipping a Johnny Walker. He twiddled what appeared to be a business card between his fingers. The small black high-gloss card had the silhouette of a stylised schoolgirl with her skirt flung high showing off her stockings embossed on it in silver. U...

No Controlling Legal Authority Ch. 02

by TheScribe on Sep 16, 2017
Novels and Novellas

The smooth liquid burned his lips and tongue. He could taste the smoky flavor of burning peat in the scotch as he swirled it in his mouth. It had a rich, earthy taste that reminded him of the sturdy stone houses and walled fields of Scotland, and never failed to infuse him with a feeling of calming warmth. This might turn into a two-scotch night, he mused, r...

Sean Leaves Karen

by jacksgirl on Sep 17, 2017
BDSM

There was going to be a party. Sean invited several friends and business associates. He told us to be prepared for twenty guests. Jillian and I cleaned and cooked for days. Well, ok, Jillian did most of the cleaning. Since I am an excellent cook, the kitchen was my domain. And I loved it. Of course, Sean insisted Jillian and I remain naked at all times. Whic...

The Girls of St Catherine's Ch. 01

by nightvoice2 on Sep 16, 2017
Novels and Novellas

The Headmaster Ritual (1) Prologue: Friday, 26 April Portia danced sinuously in the half-light of the dimly lit study, closing her eyes and losing herself in the thumping beats and intricate rhythms of the Latin music. She reached up and ran her hands around the brim of her straw hat, the fingers brushing against the silky pink ribbon. She watched him tapp...

A Very Naughty Girl Indeed!

by Jonathan Phillips on Sep 11, 2017
BDSM

The PE teacher had buzzed ahead telling me to expect you. She had not however, prepared me for exactly what I was to be punishing you. I could easily have lost my job for the punishment I chose for you. Christ, I really should lose my job for the punishment I chose for you. *** There was a knock at the door... "Come!" I shouted. You stepped inside. You...

My Friend Sophie Ch. 02

by LeanneSinclair on Sep 17, 2017
BDSM

In the previous story I introduced you to my lovely friend Sophie and told you about an evening when she and I got very drunk and she told me, in great and explicit detail, about her submissive fantasies and desires, which were focused on her male boss. I'll pick up the story again on the morning after that, briefly, although I'll probably then gloss over so...