Chastity School Stories

109,968 results
Orientation
Length
Source
Infinite Scroll

Candace's New Years Eve

by Dominic_Lee on Sep 17, 2017
BDSM

Chastity had worn her locking heels out quite often and no one ever mentioned them. Normally she would hide the locking portion under a pair of jeans. All anyone ever saw was another pair of black heels, which she owns a lot of. This is until New Years Eve. Aiden asked her to wear them out to the club that night. He liked them and wanted her in them tonig...

Christian College Sex Comedy Ch. 04

by FinalStand on Sep 25, 2017
Anal

(Once more, thank you frontma for your editing) * *Pain is either not knowing what it is or forgetting what it was* (Yes, this tale is supposed to be somewhat humorous and outrageous too. While not always comedic I'd like to think it is mostly a good-natured romp.) I was slumped down on the floor against the wall when an expensive pair of shoes came at...

Family Chastity Story Ch. 02

by antares34 on Jul 3, 2019
BDSM

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. ***** Having grown bored with how things were progressing with my sissy son, I have recently ventured into a new and fun project –filming and distribu...

Jennifer in Chastity

by Wifetheif on Sep 14, 2017
Fetish

Some of Jennifer's friends had told their secret to affording college. They had found sugar daddies, older men who paid for their college tuition and expenses in exchange for sex. Amy, Jennifer's best friend was bedding a local banker and was doing very well indeed. Freed from the financial burden of massive debt from college loans, and with her sugar daddy'...

Dual Thrill

by Mesmeri on Sep 15, 2017
Erotic Horror

This is the final sequel to 'Dual Shudder', which is the sequel of 'Dual Shiver'. I strongly recommend reading those before you start with this story. Before we start with the story, I'd like to thank my new editor JHB for his great work. Dual Thrill Chastity Dejager took another casual look at the watch on the inside of her wrist. With her combat boots, f...

Letter from Annapolis

by justincbenedict on Sep 26, 2017
BDSM

Dear Shoeblossom: I've always known I was a bad boy. My Mother used to get so mad at me...she'd want me to spend time with my sisters, and help polish the silverware...she'd shake her head because I didn't want to play with paper dolls...I wanted to be like my macho father. Mother had strawberry blonde hair in a bouffant hairdo, and what they used to call...

Chastity with Neighbor as Keyholder

by randomer555 on Sep 25, 2017
Fetish

I've always found chastity to be a really interesting idea. I'd wanted to experience chastity ever since I was teen. But now I was 30 and still hadn't experienced it. Well, I hadn't truly experienced it anyway. I'd bought a CB6000 a couple years ago and had put it on. I enjoyed having it on, but I still had no keyholder. Self-imposed chastity could only go...

Letter From Houston

by justincbenedict on Sep 24, 2019
BDSM

Dear Shoeblossom, My sister-in-law and I are thinking of turning this into a regular podcast! We had to debate whether to have it be "Letter from Austin" or "Houston" or even "Laredo" since we have family all over Texas. Thanks again for your "Taped Confessions" series. Thanks, Bunny Baxter "Talise, it just seems like you are so hard on Calder." "Why...

Marabogo: Cuckold Island Ch. 01

by eeric on Sep 19, 2017
Interracial Love

Prologue The breeze that came in from the Atlantic ocean did not do much to quell the baking sun on the beach of Marabogo. The small island laid approximately one hundred miles of the coast of Namibia, Africa. John Morton and Henry Larsen sat on the beach in their sunbathing chairs looking at all the skimpily clad women and ripped black men. Both men were...

Master Soames's submissives: Calvin

by justincbenedict on Sep 15, 2017
BDSM

Soames watched the balding blond man sweat. He looked terribly defeated, kind of like Toby, the Human Resources chap on "The Office." Soames tried to smile--it wasn't in his blood, smiling on command, to make the man feel at ease. "Calvin, just tell me more about yourself. It'll really help in the session." Calvin Sage smiled. "You can call me Cal. All my...