Boarding School Punishment Stories

127,893 results
Orientation
Length
Source
Infinite Scroll

Trinity Finishing School Ch. 01

by ProfRighteous on Sep 19, 2017
BDSM

I was sitting in the baggage claim area of the airport waiting for my niece's plane to arrive, wondering if I had been a sucker to agree to this. Three days ago, I had been just sitting down to dinner when my phone started buzzing. Figures, people always call me at the most inconvenient times. I fished it out of my pocket and saw it was my brother Matt. "He...

An Innocent's Epiphany Ch. 01

by happy_bloke on Sep 13, 2017
First Time

Today I had a revelation shown to me and I have decided to keep this diary of my progress as a sexually developed adult, finally discovering the secrets that have been hidden and forbidden from me by my controlling family and teachers. This week I moved into my new rooms at the University of Hampshire on England's South Coast. I have spent most of my childh...

Technically You are Still a Virgin...

by ElderDirt on Nov 25, 2017
Romance

When you first glanced at her face, Shari looked like she was fresh out of middle school instead of a twenty-year-old woman. Standing a petite five-feet, she had a pretty Chinese face that was framed with straight jet-black hair that fell to the middle of her back. When she giggled, her almond-shaped eyes twinkled, her cute nose wrinkled, and her sweet dimin...

Yes Sir

by TGND83 on Jan 22, 2020
Erotic Couplings

I sat on the cold wooden bench outside Mr. Anderson's office trying to control myself. I was shivering uncontrollably, not from the cold or because I was afraid of the punishment I was about to receive. I was shivering because I was so aroused at the thought of what I was about to do. I certainly fit the profile of a troubled teen but I wasn't one. I was t...

Punished by Parents-in-Law Ch. 14

by Alfamann on Sep 26, 2017
Fetish

The horse ride back to the ranch was long and painful for Rachel, Troy and I. By the time we arrived there was only a couple of hours before I had to leave with my Parents in Law, Ben and Jane, and my husband, Michael, for the drive back to the airport and the flight home. I dived into the bathroom to have a shower with Michael, but once I had removed what...

Finishing School - Staff - Mr. & Mrs. Ellis

by DonBrown on Jul 3, 2018
BDSM

Welcome back to Calder House, the place Ladies are finished and below stair girls are whipped into service. The staff are also dealt with harshly should they step out of line by Mr. and Mrs. Broadwood who ruled the staff as well as the inmates with the strap. The only difference was the staff were whipped in private for any indiscreet actions, private bei...

Managing Melanie

by kinkqueen on Sep 15, 2017
BDSM

Janet was 43. She'd been a widow for more than two years, and for all of that time she realized how hopelessly incapable she was of controlling the misbehavior of her only child, her daughter Melanie. Janet's late husband had tried to discipline the girl, by grounding her and cutting off her allowance, but he'd had little success. And then Janet, on her own,...

A Headmaster's Lesson Pt. 01

by LittleKay on Nov 6, 2018
Fetish

Greetings! Thanks for taking the time to read my story. Feedback and Comments are welcome! Please read the disclaimers at the end before leaving negative comments on the themes or content. This *is* a dark, twisted story. Apologies in advance. _________________ The only thing worse than growing up in a wealthy religious family was being sent to boarding...

Sex at School? Naturally...

by MrsJ on Jan 13, 2018
First Time

Hello, I'm delighted you're interested to learn about my high school days, which have just finished – my recollections of a young girl learning the real meaning of 'life,' discovering those innocent teenage joys of sexual pleasure, losing my virginity, and leaving school very 'sexually active.' The school I attended is a private school, hours and hours awa...

The Ranch Ch. 03

by clcarne on Sep 12, 2017
Loving Wives

She was still plugged when they walked into dinner. The young woman, who had enjoyed Colin so much, had come in after a few endless hours and released them, giving them a set of the suede outfits. Lissa laughed as she watched Colin put on the chaps. He always dressed so conservatively and his long dangling penis seemed so...so un-Colin. She was amazed th...