Chastity Gay Stories

28,507 results
Orientation
Length
Source
Infinite Scroll

Mistress CC

by cocosboy on Oct 7, 2019
BDSM

I first saw Mistress in a magazine ad. She seemed the perfect marriage between my budding interest in female domination and my attraction to black women. For weeks she was the star in my jerk off fantasies. But I was in my early 20's; a broke student with college life taking up much of my time. I eventually forgot about her. Several years pass before I find...

The Dominatrix Order Pt. 02 Ch. 04

by Jwwsmith on Feb 11, 2019
Transgender & Crossdressers

Protestors swarmed the streets of Femininus on what was the anniversary of the initial passing of the 23rd Law. It had recently been considered for repeal and been upheld by the Council of Goddesses. The protestors demanded that the 23rd Law be repealed and that same sex courtship be legalized. The predominantly liberal crowd congregated before the steps of...

Cuckolded by Kate Ch. 05

by cuckytoher on Jul 3, 2018
Loving Wives

The early morning sun streamed through the balcony doors onto Michael's muscular thighs and legs. His head buried beneath a pillow, he slept soundly. Kate stood naked on the balcony, the ocean breeze caressing her naked body like a million tiny feathers tickling her. Glancing down to sand below her she spotted a cat playing with mouse, toying with it, decidi...

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. 03

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...

Interracial In-Laws

by scatwoman on Sep 12, 2017
Interracial Love

My wife, Chastity, has a sister, Bella, several years her junior, who has always been on the wild side. My prim and proper wife was usually aghast at the latest information concerning her little sister's sexual exploits. It wasn't that she condemned her, she just didn't understand her. I, on the other hand was always fascinated, and frequently aroused by her...

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...

Life and Time of Lady Vargos Ch. 07

by rik581 on Mar 26, 2019
Transgender & Crossdressers

"The New Bitch of Vargos Manor" Written by: Rikki Lady Vargos begins to exert his new found powers as Lady of the House. He is able to channel many of his frustrations and anger through being tough and almost insulting to those try to accept him as the Baron's wife. As a result, word spreads and Martin is slowly becoming the Bitch of Vargos Manner. "Thank...

Mistress Starla Proves Her Point

by justincbenedict on Apr 16, 2018
BDSM

Porky was weeping bitterly, and at the same time, his dick was straining, and quite excited. Who was this girl? Starla was his friend Spalding's cousin, and he'd seen how she enslaved him--Olivarius, the school's intramural lacrosse coach had told Porky that Starla had taught him how to suck his own dick... Several young women of Porky's acquaintance foll...

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...