Chastity School Stories

109,968 results
Orientation
Length
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Infinite Scroll

The Headmaster's Room Ch. 02

by Mag58 on Sep 12, 2017
Fetish

When the bell rang for the end of the morning lessons at 12.30; I was strangely disappointed at not having been called back to Mr Skinners' office for him to finish my punishment in his study. I ate lunch with some girlfriends then hung around the gym buildings smoking cigarettes and talking about a party that we were going to on the Saturday night. As the b...

Molly - My First Love

by apeion on Sep 2, 2017
First Time

My first real love - that would be Molly. As the old song went, she was a dark haired beauty with sky blue eyes. Barely 5'3" tall she was slender with long legs and small round breasts. We met at orientation on our first day at college. After I helped her with class information and schedules she thanked me and then wanted to know if I wanted to grab lunch. S...

Amanda, Friends Helping Friends

by Dave_Loves_Puss on Nov 2, 2020
Erotic Couplings

It was Friday! Fridays were always a day to relieve some stress after a long week of school. It was a Navy school which meant they crammed us full of information during the week and tested our comprehension every Friday. I did well so it was time for reward. In Great Lakes, there was not much to do on base on a Friday night except drink a few beers at the c...

Teaching Patti Ch. 1

by Dixon Carter Lee on Sep 11, 2017
Novels and Novellas

All characters in sexual situations in all chapters of this story are 18 years old or older. * I'd escaped high school ten years earlier, and was living in Manhattan, doing the acting thing; a few showcases here and there, a Broadway production of "Godspell", and living well off some commercial residuals. Then, suddenly, the show closed, the friggin' comme...

Lesson Plan Ch. 04

by GettingItDone on Sep 13, 2017
Fetish

Thank you for reading my stories, and I am sorry if the wait between chapters is longer than you would like. I am doing my best, and promise to keep writing them as long as the response to them is positive. As always, rating and commenting on the stories are greatly appreciated, and if you would like to make suggestions as to possible scenarios you like to s...

Talk To You After Class Ch. 02

by Quenton2123 on Sep 1, 2017
First Time

(Hey, this story is a continuation of the short See You After Class, if you haven't read it yet you may want to read it now, or you could miss out on some things.) Jake walked into West River High School on Monday morning in the same way he always did; slightly sleepy and several hours early. This earliness wasn't born out any particular desire to be at s...

Sweet Smell of Sex-cess

by lesliejones on Sep 14, 2017
Fetish

[Those put off by natural functions, including periods, and things like body smells of different kinds should skip this story. The narrator and all other characters are 18 or over.] In my admittedly limited experience, girls normally place a far greater emphasis on personal hygiene than do boys. From when I was little, I learned to wash myself thoroughl...

A Stile

by penda on Sep 17, 2017
Non-Erotic

I'll always remember the first time I saw Joan. I was fourteen and it was the earliest summer I can recall when it had been really hot. I was in a real bad mood too, because the teacher had kept me behind after school to go over some crazy sums I'd gotten wrong. My school was in a small town some three miles away from the village I lived in and on my way ho...

Life as Clara Oswald Ch. 02

by zmoorez on Nov 23, 2017
Celebrities & Fan Fiction

Clara had been teaching for about a week, and had just finished an afternoon English class with Year 11. When all the students had left the classroom, Mr. Davis suddenly appeared. He had spoken to Clara yesterday and instructed her to wear thigh-high stockings and a skirt. She had picked the same stockings as she wore when he came to her house, and a tight j...

Forced to Change Ch. 03

by SimoneLisbon on Sep 15, 2017
Novels and Novellas

Chapter 3 Paul Donnelly, Jr. was already in college my last summer with the Build-A-Village program. He'd been in college for two years, but Mrs. Wellington, the teacher who supervised the trip, adored Paul. She worked him in at the last minute as a chaperon. Paul was excited by the responsibility. He found the situation hilarious. He loved the responsibili...