Summer In Chastity Stories

360,281 results
Orientation
Length
Source
Infinite Scroll

Letter from High Coombe

by justincbenedict on Sep 24, 2019
Exhibitionist & Voyeur

Dear Shoeblossom... I don’t know if my involvement with Satanic Silki is my fault, because of my neurosis? You judge... First, my parents were weird, warped people. The oldest of us kids, Breanne, became an adulterous bitch, and my brother Brian’s effect was, he was a cruel asshole. And he ran off with my first wife. I’m Brogan, the youngest, the “sensiti...

A Freshman's Summer Class Ch. 04

by CapnSteelBoy on May 11, 2020
Transgender & Crossdressers

Edited by HotandHollow **All characters are of legal age for adult content.** We Continue from where we left off with our brave hero, as his adventure continues during his summer of higher education learning! This is a continuing series I'll be releasing as my helpful editor(s) help me clean up my mess.. Much thanks goes out to them, as the editor(s) tha...

Paige and Spalding

by justincbenedict on Jul 4, 2018
BDSM

Dear Mom, Thanks for the lemon bars. It'll help me stay awake during my property class. Tell Rylie that I'll bring back her mohair coat, don't have a cow. So you were asking me about how things are going with Spalding. I was so glad you and Dad liked him when you came up to school. I agree he's cute and has a good sense of humor, and Dad said Spal was obv...

Being a Subbie Hubbie

by justincbenedict on Jul 3, 2018
BDSM

The doctors walked leisurely in the corridor. Dr. Gibbon Brierley looked tolerantly at his colleague. "Shep, the decision you make to become a submissive male can be incredibly freeing." "Before, when I was married to Saskia, certainly I was well looked after. Saskia was loving and kind and a great mom to our kids, but I was a nervous wreck. I smoked fou...

A New Beginning

by justincbenedict on Sep 17, 2017
BDSM

Parrish Pindler stood in abject pain as his testicles dragged, with the extensive weights attached to his chastity belt. Babs whacked the weights between Parrish's legs as he stood before her. "Yup, that fellow Copeland is a genius! I needed a little more vavoom to your chastity device, and this certainly has given you something to think about, huh babe?" B...

Infidelity and Chastity Ch. 04

by rockbohunk on Sep 15, 2017
BDSM

"I guess that you will either have to ask me for help when I am here, or jump in the shower." Sara shook her chains and looked up at Rick, "Please Ricky, I promise not to do it again. Please?" "Promise?" Rick asked. "Like you promised not to cheat, or to lie? You should be damn lucky that it's not the middle of summer. You would be tied outside to your Pil...

The Tutor of Buttermilk Falls

by justincbenedict on Sep 17, 2017
BDSM

Alfred Nemirow rubbed his throbbing dick tentatively, and gave Fanchon an imploring look. His wife of three years was impervious to such looks,but Alf tried anyway. He looked down at the steaming Starbucks cup, and then checked the mirrors of the Mitsubishi Galant...was anyone looking? God knows no one wanted to catch Kissler Systems's head Accounting and F...

A Freshman's Summer Class Ch. 02

by CapnSteelBoy on May 11, 2020
Transgender & Crossdressers

Edited by HotandHollow **All characters are of legal age for adult content.** We Continue from where we left off with our brave hero, as his adventure continues during his summer of higher education learning! This is a continuing series that will continue, releasing as my helpful editors help me clean up my mess for release. Much thanks goes out to them, a...

Greg's Surprise Ch. 02

by SensualCurves on Sep 14, 2017
Fetish

(This is a continuation of a short story which was submitted to Literotica some time ago. Following a large reader feedback requesting further adventures of Greg and his Mistress Sasha, their story continues. If reading my work for the first time, this author respectfully suggests you read Part 1 first.) * Warm summer sunshine filtered through the bedroom...

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'...