Chastity Step Stories

113,217 results
Orientation
Length
Source
Infinite Scroll

Carl & Chastity: 2nd Date

by Ninjafish on Sep 14, 2017
Erotic Couplings

Chastity didn't ring until the evening. She had had quite some debate with her friends over a coffee in the morning about how soon is too soon, the usual argument erupted. The married friend telling her to not play games and ring straight away, the single friend telling her to wait a week and even then tell him you are busy. Sadly she never managed to put tw...

The Perfect Pair Pt. 09

by ChangeYourPassword on Oct 6, 2020
Fetish

The Perfect Pair, Chapter 9 (fetish, chastity, consensual, cross dressing) By ChangeYourPassword Author's Note: This is a work of fiction. It is a story of sexual fantasies and fetishes. These sexual practices are not for everyone, but those of us who delve into them understand the allure. The characters in the story certainly do. If you enjoy this story...

Mark & Lisa Pt. 01: Key-holder

by LockedSissySubmissive on Sep 25, 2017
Fetish

When the doorbell rang I honestly thought I was hearing things, I'd lived in my apartment for two years and I don't think anybody had ever rang it before. It's not that I don't have any friends although if I'm being honest I don't have many, it's just that I live in a secure block and any visitors would ring the bell at ground level and then I would either c...

Change of Control Ch. 04

by kaptiv8ed on Oct 26, 2020
BDSM

Several days had passed since the new couple had shared their latest "adventure" as they were calling the encounters. The two longtime friends had reunited after several years apart at a charity event less than a month prior, and the two hit it off very quickly. Both with time and opportunities in their life to explore and develop a transparent and mature re...

Loraine's Self Bondage Re-Creation

by loraineveritas on Mar 12, 2019
BDSM

The following is my re-creation of an event that happened a few years ago. I had been a sissy slave to Mistress Marie for over 2 decades during which I become a totally submissive slave to Her every desire. I think of Her often as She has passed now. While doing Self-Bondage activities shortly following Her passing my wild imagination conjures up the Mistres...

Win a Cock Cage, a Contest

by JrBlueBalls on Jul 31, 2019
BDSM

The following short stories were written as submissions to a contest run by the company that sold my wife our first cock cage. I was excited to write of our experience, until I saw the contest rules that would allow them to use our likenesses in any of the advertising or promotional materials. While we really enjoy their product, I didn't like the contest ru...

Sissy Girl Forever Pt. 01

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

The call from Mistress Andrea made my day. I hadn't seen her for over a week and was looking forward to playing with her & having my chastity finally removed. You should know that Mistress and I have known each other for many years and have I always enjoyed being her sissy sub. Lately she has been training me to be more feminine in appearance. I have been r...

Prison Made Me a Better Man Ch. 01

by Cuckyboy3 on Jan 7, 2020
Fetish

Chapter 1 - Going to Prison I looked at my calendar to see that I had a doctor's appointment today. It was with some new doctor in the city. My wife, Linda, set it up for me a month ago under the pretense of a 'joint health checkup'. It turned out that this Dr. Fleming was a well-known female sex therapist who had a great reputation for helping couples impr...

Inescapable Chastity

by blue0011 on Sep 28, 2020
Fetish

Note: This story contains chastity themes, anal penetration, female domination, mild consensual non-consent, and a bit of science fiction. "100% guaranteed inescapable chastity," the ad promise on her laptop screen. She flashed a brief smile at the possibilities. With a click of her mouse, it was on its way to her mailbox. The tall, thin man was still sta...

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...