Chastity School Stories

109,968 results
Orientation
Length
Source
Infinite Scroll

Letter from Raleigh

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: What will happen now? Yesterday, Pebbles summoned me from the closet (I undress and kneel there as soon as I come in from work) and instructed me to put on my pink panties and my pink and purple lacy floral print baby doll nightie and high heels. I walked into the living room, and there was Peb, and her sister Faye, and the six guys in my...

Cruel Mistress Carnation

by justincbenedict on Sep 15, 2017
BDSM

JULY, 2005 Clausen Widdicombe pulled up just outside Enger Haverford's farm...She was the town dominatrix, and a bit weird, but Clausen had reasons for being here...he wanted to see Enger's niece, the wonderful Carnation!!!! Clausen got out of his little Miata convertible and sighed. Enger's youngest daughter, 20 year old Secondari (She and her sister Sel...

Happy Birthday! I Think?

by skinnywhiteboi on Sep 15, 2017
BDSM

"Come on, everybody knows you're a slut! It's not like you're not into guys." I called after her as she walked away. It was my eighteenth birthday, the first day of the school year, and for the last half hour I had been begging Elizabeth Cross to have sex with me. Elizabeth, or Ellie as she prefers to be called, was the captain of the schools cheer team. Eve...

Family Business

by fantaseeboy on Jul 27, 2020
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** Laying on my bed in my room in my mom's trailer, my laptop was set on the table beside me with my webcam aimed where I lay. White, satin, bikini panties were looped around my left ankle. The snug-fitting, stretchy crop top clung to my narrow, smooth chest and left my midriff bare....

By My Own Device

by maxout09 on Sep 12, 2017
Sci-Fi & Fantasy

3:00 pm 12/16/15 - Present day My name is Christine, and I'm a 30-year-old high school teacher with a very interesting tale to tell. I'm a sex slave to a computer. But to fully understand what brought me to this moment, I need to start from the beginning. I grew up an only child in a farmhouse. It's not that my parents were farmers they just wanted the so...

Letter from Boston

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: I have read with interest your letters from chastity belt couples. I really thought I was an enthusiast, but now I think it may have gone too far. My love affair with chastity and denial began, I think, in my early twenties. In the summer after my junior year at Harvard, I wrecked Dad's BMW while drunk on the Montauk Highway, near our vaca...

The Devil's Mystery Box

by bbcummings on Jan 30, 2019
Fantasy

Author's note: My idea is for the stories to mostly be 3rd person. However, this section basically has to be second person, so bear with me. *** The box you found was peculiar. Usually, a box didn't come with strange markings. It wasn't made out of exotic materials that seemed to defy normal physical behavior. Boxes were usually cardboard or wood. They held...

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Letter from Turkey Thicket

by justincbenedict on Sep 15, 2017
BDSM

Dear Shoeblossom... Inspired by Grant and Lyla's "Letter from Fritters, Alabama" I send you this! I bade Vince good night, kissing him on the cheek. Vince looked a bit dazed. "Troyce, you don't have to end it here. Your husband is clearly not what you want...you like me, right?" It was hard for him, my sudden distance, since my tongue had been plunging i...

Mistress Treva Wins Again

by justincbenedict on May 29, 2018
BDSM

Dr. Shepherdson Grangerford milled about at the fundraiser, his adoring wife, Treva by him, the ultimate arm candy even after all these years. A balding, chubby fellow came up, grabbing Shep's hand. "Dr. Grangerford, everyone is so pleased that you made the fundraiser, and that you'll be heading up the Ophthalmological Wing. We probably couldn't have gotten...

Aunt Janet's Hot Tub Ch. 03

by tmanners25 on Sep 15, 2017
Anal

"Thank goodness you're here," declared Aunt Janet as she opened the door. She waved to my wife, Roxanne, as she was backing out the driveway. We had gotten a call from Aunt Janet that morning that the hot tub wasn't working. She asked if I could come over and see if I could fix it. So here I was! "What's wrong?" I asked. "Nothing seems to work," she replie...