Boarding School Punishment Stories

127,893 results
Orientation
Length
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Infinite Scroll

Emily & O'Shea

by innocentwriter on Sep 16, 2017
BDSM

**All characters in the story are, as identified, 18 years old or above.** Emily could not believe she was wearing this bullshit outfit. Like some slutty costume, but it was for real. She never wore skirts, especially ones cut at the knees, or white dress shirts, or knee high socks. It was all Jamie's fucking fault. Jamie's parents had bragged to Emily's p...

Birthday Surprise

by ALpelosi on Dec 24, 2017
Anal

I never imagined that on my 18th birthday, I would be deliciously fucked until I screamed. ******10 hrs Earlier****** I've been up since the crack of dawn staring at the Diamond Pendant from Bloomingdale's in its box that fell out of a large envelope and at the message that came along with it. 'Sorry I won't be able to make it hun. I will be away on busin...

A Sissy in the 22nd Century

by JerkGently on Jul 1, 2020
Transsexual

In a future not too far flung, humanity has progressed to a stage where almost all production and provision of society’s needs is automated. With no need to work, all citizens are instead driven to find lifestyles that fulfil their own and each other’s fundamental desires. This is achieved by the medium of an overruling system of artificial intelligences and...

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Mrs. Swanson's Boarding House Ch. 07

by 0ra11yfix8ed on Sep 25, 2017
BDSM

Mrs. Swanson watches as her housekeeper instructs two candidates for the position of assistant housekeeper after the three young men and the three young ladies participated in the ceremonial first milking of Mrs. Morton's son Carl. "What do you think?" Mrs. Swanson asked her long time friend Sara Lee Morton. The two ladies were sitting in the parlor watch...

Letter from Carker's Rents

by justincbenedict on Sep 24, 2019
BDSM

Dear Shoeblossom-- Since I taped this, I also have enslaved my brother-in-law Santiago and his basketball team. So I have real progress going on here in Carker's Rents! Love, Sugar Perez "Sugar, I am having a devil of a time getting these thorns out of my, um--" "Your diaper. Say it, Esteban." "Don't--don't you think it was punishment enough for me to...

The Good Girl

by LuxDominus on Sep 17, 2017
BDSM

It was September 5th, the first day of her senior year, 5 am. Morgana Felicity Avingone, or Morgan for short, had turned 18 just a week earlier and awoke in a drowsy state that normally accompanies 5am. It was still warm out and as she stretched attempting to open her eyes to greet the morning sun, her pajamas pulled against her supple young body. She smiled...

Ms. Madison's Puppy School

by Sarahcheer on Sep 11, 2017
BDSM

Mr. Morison looked at his two 18 year old daughters and gave a long sigh. The girls, Samantha and Sarah, both had bodies to die for but the manners of well spoiled princesses. He knew he had spoiled the girls all their lives and especially after his own wife's death, giving them money to go to the mall whenever they wanted, sending them to an exclusive board...

Twisted Ropes

by SpiritSarcyn on Jul 13, 2020
BDSM

"Oh! Three. Another please Sir." Her voice was shaky, her body already asking why she had agreed to this ordeal. The whip came lashing across her back once more, the leather tendrils wrapping around her body to lick at the soft skin of her belly. "Four. Another. Please. Sir." The words were wrung out of her, each one more troublesome than the last. Paige A...

Room Six

by CottonFarmer on Sep 17, 2017
Exhibitionist & Voyeur

Note: This is the story of what happened to me over thirty five years ago. Since the school is still in business I have changed its name and done my best to disguise its location. I doubt that this sort of thing still occurs there, but I have no way of knowing for sure. I have also changed the names of the participants, because it's unlikely any of these wom...

Jane Marwood, Governess Ch. 01

by harrietmarwood on Sep 25, 2017
BDSM

On London's Great Portland Street, there is a row of gloomy mansions that have not changed appreciably in the last century. There blossomed the romance of Michael Lovel and Jane Marwood. It was a story so bizarre in its beginnings, so fraught with suffering in its outcome, that the old house, which witnessed its birth and infancy, might well look melancholy...