Boarding School Punishment Stories

127,893 results
Orientation
Length
Source
Infinite Scroll

Travelling by Airplane

by PrincessErin on Sep 1, 2017
Humor & Satire

I rarely go anywhere. I think I've been on a plane no more then six times in my life. I just recently flew from Ottawa to Toronto. I truly believe that I broke all the rules in regards to having a smooth trip. I hope that no one follows this example. This is a warning to others on how not to travel. Arriving at the Airport When they say to be at the airpor...

Identity Crisis 01

by BabyDreamer on Sep 15, 2017
Transsexuals & Crossdressers

I would like to thank Kriskrossedup for helping me to edit the following story. - My name is Victor Janice and I am eighteen years old. I have never been very manly, always keeping a slim and child-like form. Along with my name, my body simply made me the center of all the kids' jokes. My last name is very awkward and feminine, which has brought me troub...

David's French Tutor Ch. 02

by Thorilla on Aug 29, 2017
Fetish

(It was 1885, and as a nineteen year old boy I was staying with family friends at their large house in the English Midlands. I was there to learn French conversation under the tutelage of Miss. Marie; the family had two 18 year old twins, Anna and Sarah who were also learning French with me) * Miss. Marie stood up and rearranged her petticoats carefully, s...

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...

Amanda's Gifts

by OldManSoftHeart on Jan 6, 2020
Erotic Couplings

I've done my fair share of traveling the last few decades earning over a million airline miles, but not all on the same airline. So I've had my share of lost luggage, delayed flights, and memorable travel mates. I used to run to my gate after getting off a delayed flight, only to look out the window at the gate, and watch my plane pull away without me. I hav...

Sheerview Heights

by swxtchelijah on Apr 20, 2019
Amateur

_Disclaimer this is my first ever Chyoa story I hope you enjoy!- - - - - - _ It was a Sunday, a beautiful Sunday at that and where was I. Stuck inside touring this new ‘prestigious’ boarding school alongside my step-mom and step sister. My real father was fed up with my trouble making and gave me an ultimatum, work or go to military school. Luckily my step-m...

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A Trip To Remember

by BlueEyed5ftAngel on Sep 12, 2017
Erotic Couplings

the daydream beginning after.. Her thoughts began to race.. and ending with... Her own breath was quickening as his fingers inched closer and closer to her private region. What the hell else could go wrong screamed through her mind as she glared blankly at her monitor? The mesmerizing starfield screen saver had replaced her charts but she continued to star...

Gang Bang Penny

by AnnGoode on Nov 19, 2018
BDSM

Editor's note: this story contains scenes of incest or incest content. *** It was the middle of the night. Penny lay in bed next to her sleeping husband, John. She was naked and had one hand between her legs and the other fondling one of her tits. She looked across at John thinking what a kind loving man he was. It was so sad that his sexual drive did not...

Prep School

by Spartacus on Sep 15, 2017
BDSM

"Mrs. Jameson?" the voice on the telephone asked. "Yes" Kellie Jameson answered. "This is Ms. Milton at the Colhaven Prep School" the voice responded "Our headmaster would like to see you regarding your children. Could you come in tomorrow around 5pm." "I" Kellie stuttered "I suppose so. Is there a problem?" "Mr. Lace will have to explain it to you when...

Secret Weapon Ch. 03

by Ton8ty on Sep 15, 2017
Sci-Fi & Fantasy

Chapter 03 -- Red Packs to Leave Dear Reader: This story presents adult situations in graphic detail. It is not suitable for anyone under 18 years of age. The characters and situations in this story are entirely fictitious and any resemblance to actual people, places or events is coincidental. * The two elegantly dressed young women ducked into the tiny...