School Punishment Stories

126,101 results
Orientation
Length
Source
Infinite Scroll

Finishing School Handbook

by brewster926 on Sep 16, 2017
Humor & Satire

Please note: this is an official copy of the handbook actually used at Dr. Deucel's famous finishing school which was in existence in Wayward on the Tool in Lower Suckexx during the latter part of the Nineteenth Century. Dr. Deucel's school was known for taking ladies in their twenties and older that everyone else had given up on and helping them become happ...

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...

The Feared '57' Ch. 02

by lesliejones on Sep 12, 2017
Fetish

To Megs—with joy for her continued high spirits Irene Crawford, Oakhurst's principal, immediately started having second thoughts about Janet Sanders' rather impetuous request to award the "feared 57" punishment to senior Marcie Williams. Irene realized that she had responded in a positive way to Janet's mentioning to her that the request was forthcoming bu...

Kimmie's Lesson

by kimbelina on Dec 10, 2017
BDSM

Kimmie Church Mrs. Kimmie Church Mrs. Jeremy Church I was gazing down at my paper, every single line of the page filled with my romantic doodles. I looked up occasionally during class, either so that Mr. Church would think I was listening to his lecture, or just to watch him as he moved. Whenever he made eye contact, I blushed, embarrassed at the inapprop...

Discipline is Hard Work Ch. 01

by BrooklynAnders on Jul 10, 2019
BDSM

Jessica adjusted the tops of her stockings in the mirror over the sink. She wasn't used to wearing such sensual lingerie at work, and to be honest she found all that lace between her cheeks a little uncomfortable, but for the first time in a while, she had a date after work. She smoothed down her short but smart grey skirt, and put her stern work face back o...

High School Spanking

by DonBrown on Mar 20, 2018
BDSM

When our youngest daughter, Teri, left school, it was the end of an era. No more delivering and collecting kids from this school activity or the after class detentions. After class detentions, we would have welcomed those when I was at school, instead of the beatings, which were handed out wily nilly. Don't get me wrong, I am not saying we did not deserve...

Mr. Anderson's Office

by mindless_indulgence on Sep 17, 2017
Mature

"Miss Winters," my teacher called. "Principal Anderson would like to see you." The principal? I hadn't done anything wrong! What else could they possibly do to me at this school? Hadn't four years of torment been enough? I gathered my things and walked towards the door. My exit was accompanied by assorted catcalls as well as flying projectiles of paper an...

The Party's Ripe for Caning

by lesliejones on Sep 19, 2017
BDSM

It was a most unusual change for the boys in the senior class at Hamilton Hall, an elite high school, when the Headmaster, Mr. Henderson, appeared in their class to introduce them to their new home-room teacher, Miss Linda Crawford. First of all, there had never even been a woman teacher at Hamilton Hall, much less one so young as Miss Crawford, nor did it s...

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...

An Appropriate Punishment Ch. 02

by Frixmaster on Aug 31, 2017
Fetish

If you have not read the first story ‘An Appropriate Punishment’, it is recommended that you do, otherwise the full context of this installment may be missed. Having now left the hall, I made my way in the direction of the library, barely able to put one foot in front of the other from the distraction inside my pants. To hide my now rock hard boner, I pul...