Headmaster Stories

774 results
Orientation
Length
Source
Infinite Scroll

Headmaster's Life

by FayeBaye95 on Sep 13, 2017
Fetish

Being the headmaster of an all-girls college was a good job. Fuck, it was a brilliant job; surrounded by buxom girls aged 18-21 was a dream. A lot of these girls were willing to get on my good side to increase their grades and reports, I was more than willing to accommodate. A slurping sound brought me out of my thoughts as I looked down at the whore current...

Celebrate Freedom!

by sophia jane on Sep 16, 2017
Reviews & Essays

Thanks to Softouch911, again, for being a fantastic editor and friend! * My grandmother had a bookmark when I was growing up that said: "Celebrate freedom. Read a banned book." The irony never escaped me; while we have free press, we also have people who exercise their freedoms by protesting, and banning, the words of others. My grandmother celebrated he...

Insane-y about Hermione

by weltscherz on Jun 5, 2020
Fan Fiction

**** (All characters in this fictional work and in oncoming continuation of said work are at least 18 years of age) **** They can't understand._ Maybe they do not want to understand. Yet you don't deem it much as something you should care about. Sure, you have neither seen nor exchanged anything besides a few 3-words-long text messages with your friends an...

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The Headmaster Ch. 02

by l8bloom on Sep 13, 2017
Erotic Couplings

Thanks to rgraham666 who goaded me into writing more about these characters. Thanks to snowflakesarah for editing. The following Saturday I have broken a sweat before I even make it to the locker room. It was a week ago that the headmaster invited me to be his lover. That seems far away now. But what we did in my apartment a few nights back is uppermost in...

A Visit to the Gym

by djt_one on Sep 17, 2017
BDSM

It took two weeks for the cane marks on Sue's behind to fade. This was not surprising after what had taken place in the headmasters study at the school reunion. Not only had Sue been soundly thrashed, she had also been thoroughly fucked by her old headmaster. All of which had happened while John, her husband had looked on, and at some stages taken part. Ther...

Suzy Matron Ch. 02

by robin35 on Sep 19, 2017
Erotic Couplings

I left the cottage and headed for the exam room. I had Maths and English this morning and I was confident that I could do well with both of them. They were my strong suit along with history. It was the languages that were my sore point and they were tomorrow and I would have to do revision for them tonight. I got to the exam room and looked for my seat. Bei...

The Headmaster Ch. 05

by deadeye_76 on Sep 13, 2017
Erotic Couplings

Chapter 5. The Halloween Party We have been at the school now since July and the Halloween Party was approaching. My wife and I decided to go out and get some costumes that covered us enough that we couldn't be recognized if we didn't want to be. I ended up going as a ghoul with a face mask and a completely covering robe with a hood. My wife selected, of al...

Another Year at St Cat’s Ch. 04

by nightvoice2 on Sep 25, 2017
Novels and Novellas

Winter Sunshine (2) --------------------- Thursday, 21 November --------------------- David looked around Helen's room while he waited. It was similar to his suite: a large old-fashioned study with a large desk, chairs and a large bookcase all made of sturdy-looking oak. Her desk was very organised: the papers neatly stacked and the pens uniformly lined...

The Party's Ripe for Caning Ch. 03

by lesliejones on Sep 19, 2017
BDSM

[This story takes place in a prep school which prepares pupils for three years after high school for university, from ages 18-20. Previous chapters explored Miss Crawford's introduction to the strict disciplinary regimen as the first female teacher of the boys' school.] Linda Crawford now had completed her second full year as an English teacher at Hamilto...

Mercedes Senior Year at St. Vincent Ch. 02-03

by OTKTop on Aug 28, 2018
BDSM

Chapter 2: Mercedes is aroused from her spanking. (This is more of a story I have written for a submissive friend of mine. She likes to imagine what it could have been like to be spanked at her boarding school. It's only real in that this is what she imagines happening.) Mercedes walked quickly back to her dorm room, her mind clouded with a variety of thou...