Keyholder Chastity Stories

6,874 results
Orientation
Length
Source
Infinite Scroll

Seduction at Belinda's House Ch. 10

by AndreaJordan on Oct 30, 2018
BDSM

Belinda had just showered and dressed when Kate knocked on the door. She could hear James cries from inside the padlocked box and she reached down to open the small four inch square hatch as she skipped through the lounge. James's eyes peered through the small opening just as the fast of blur of her denim legs rushed passed and on to front door. Kate had co...

Teased by My Neighbor Ch. 05

by randomer555 on Sep 21, 2020
Fetish

"Don't stop! Don't you dare fucking stop!" Beth cried as she neared yet another orgasm. I kept licking, painfully aware of my aching balls and tightly locked dick. I don't know how I hadn't gone insane yet, but I had made it to the last day of the week. My balls were definitely screaming at me to release them, unaware that they were no longer under my contr...

Successful Businesswoman

by mattpantyhose on Apr 17, 2018
Group Sex

"It's a man's world and it's tough to be an independent woman" some say, but I tend to disagree. My name is Samantha, before I prove my point, let me tell you few words about myself. I am thirty seven years old, but remain in a perfect shape; I eat well, exercise regularly and use all the latest cosmetics that supposedly stop the process of aging. All these...

Necessary Control

by macktosh on Apr 23, 2019
BDSM

This is one of my earlier stories, but I hope it's still enjoyable. It was written for the following prompt: "A masturbation addict notices that her clit is gradually being desensitized by her own excessive stimulation, making it more and more difficult for her to reach the orgasms she craves. She fears that if she can't break her addiction to cumming, she m...

His Wife's Fetish Ch. 01

by ArthurSummer2 on Jul 17, 2019
Fetish

Note: This story contains themes of male chastity and light femdom. The themes here will be fairly gentle, but it is still a femdom story, so be aware! ***** James Taylor and his wife Ava lay in bed together in their Sunday night post-orgasmic bliss. They had been together for eight years, dating for five and married for three. Their sex life had been norm...

A Domme at the Colfax Inn

by justincbenedict on Jun 19, 2018
BDSM

Nibs wearily tried to stay polite with the touron on the phone. Nibs, since childhood had referred to most of the tourists who came to the Colfax Inn as combinations of "tourists" and "morons", thus "tourons. "That's right sir...We are near Lake Colfax. My family has owned the Colfax Inn since the seventeen hundreds...No, that's the Buttermilk River. Yes,...

Letter from New Piedmont

by justincbenedict on Feb 7, 2018
BDSM

Dear Shoeblossom, I can still remember Rebecca's first comment: "You sure you want to do this, kid?" A full-figured ash blonde with brightly glossed lips...pure Jersey girl. "You really want to move in with me...the sessions aren't enough?" Sometimes the sessions were way too much, but I was lost without Mistress Rebecca. 46 to my twenty-three, she'd bee...

Letter From Palo Alto

by justincbenedict on Sep 17, 2017
BDSM

LETTER FROM PALO ALTO Dear Shoeblossom, My wife Lillian is also the keyholder to my Prince Albert piercing. Much of our time together my cock is struggling to erect against the cruel way it is locked in a bow shape against the piercing in my testicles... Lillian teases me a lot, and spends hours walking around in front of me wearing very little...demibras...

An Open Letter to My Goddess

by minicockboy on Sep 16, 2017
Letters & Transcripts

This is an open letter containing what I really want to say to my girlfriend, but can never quite find the courage to do so. Here though, I imagine what I might say if I were to send such a letter, and will follow this with what might happen as a result of the letter, in future chapters. ---- To my beautiful girlfriend, You are the most beautiful, gorgeou...

RTFM

by astuffedshirt_perv on Sep 26, 2017
Toys & Masturbation

Note: This story takes place in the near future. The toy in this story was inspired by a story on another site, "The Curator," and is used with permission. Google "Streetwalker Squid Stimulator Deluxe with Partner Play" to find it. Karen started to shake in her silken sheets as her orgasm hit. Despite being alone in her apartment, she instinctively grab...