Chastity School Stories

109,968 results
Orientation
Length
Source
Infinite Scroll

18, Old Enough For Love

by R410a on Sep 5, 2018
Mature

This story is based on a girl my youngest sister grew up with. I have changed the town and people's names, otherwise it's fairly accurate. * Mom and I sat at the kitchen table looking out the window as the girl next door trudged off to school. She had recently turned 18, wearing baggy pants, combat boots and a flannel shirt buttoned up to the neck. No make...

Therapy

by Worknhard4fun on Sep 13, 2017
Erotic Couplings

(The seventh installment in the Lance Sheldon Chronicles) Prologue The look of shock must have been plastered all over my face as I stared at my laptop because I heard Jessica say, "What? Is something wrong, baby?" I did my best to change my facial expression as I looked up at her. "No," I assured her, "just can't get over the extreme people will go to in...

Daniel Ch. 06: Cums in Their Ends

by ZachDocEight on May 13, 2020
Anal

WARNING: This new story completes the introduction of Daniel my newest character. Here in involves scenes of graphic sex including seduction, reluctance, cunnilingus, discipline, breastfeeding, anal and incest. If that is not what you are looking for don't read on. All sexual acts depicted in the story are committed by female adults over eighteen years old....

Spellbound & Sissified

by EROTICbearscribe on Oct 19, 2020
Transgender & Crossdressers

SISSY FOR A SPELL The Omega Psi Phi Fraternity loomed in front of him. The lights were on in almost every room. Frank's hopes, that maybe the brothers of Psi Phi were at the Halloween party across campus being thrown by their sister sorority Sigma Gamma Rho, were dashed. He took a step forward. His hand was shaking and the child's Jack O' Lantern bucket...

My Roommate's Ex

by GuyJD on Sep 16, 2017
Interracial Love

I began college about a month ago. I can remember being a B student in high school but college is a big challenge for me. So here I am, an above average student who is struggling to keep a C average in a predominately white college. My name is Agnes but my friends call me Aggie. I am your basic black girl who struggles to get out of the ghetto by advancing h...

The Root and Nasty Rachel Pt. 01

by RootRadio on Aug 7, 2018
Erotic Couplings

His name was Luther. Luther Casey. Most of his friends called him "Lute." Though "Root" was a nickname he picked up as a kid, thanks to a younger cousin who had trouble pronouncing his "L's", and it ended up being a self-fulfilling prophecy. Because, by the time Lute started high school, his genitalia had grown to truly impressive proportions: ten inches lon...

My Neighbor Pt. 01

by lmollybee on Apr 4, 2018
Fetish

Hi, my name is Molly I am 18 years of age, and this is my first article! I live in a small town near the beach, and not much happens here. It's my mom living in our two bedroom ranch and me. Our house is quaint; we have a small yard, a few trees and a fence that needs some work. A lot of things around our house need work since my mom is ridiculously busy and...

A Soldier's Story Ch. 04

by Wifetheif on Sep 16, 2017
Sci-Fi & Fantasy

Valet School was sort of like what I expected. There were tough as nails Sergeants running the place with a Lieutenant Colonel in charge of the entire operation. In a lot of ways it was like NCO school back home. The first day were were ordered to strip and the drill Sargent inspected us in detail even rolling back our foreskins when they examined us. We had...

Kate's Mom Comes To Visit Ch. 04

by Catytheghost on Sep 16, 2017
Transsexuals & Crossdressers

Part 4: Plan B and a Question to Ask and a surprise! Kate I went and talked to Mom about my little conversation with Jasmine and Sally. Now, I'm sure you're wondering when we had this, aren't you? Well, it just so happens that Sally and Jasmine are both telepaths like me, so we talked while Sally was riding me. Don't look shocked; gee, we are Witches afte...

American Mom Ch. 01

by Hardplay on Sep 11, 2017
Celebrities & Fan Fiction

Francine Smith's skin glistened in the harsh light of the office as she gripped the oaken desk with her manicured hands, panting and sweating. She was perched upon a pair of four inch tall black platform heels, wearing only a matching black garter belt and stockings. The sexy, tall heels lifted her rounded ass and highlighted her strong thighs. Her long...