Chastity Key Stories

55,541 results
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Length
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Infinite Scroll

Anything for Her

by aweatherly on Sep 26, 2017
Fetish

DISCLAIMER: This story features a loving couple who participate in female domination, cuckolding, humiliation, chastity and cum-eating with the consent of both parties. If these themes offend you, feel free to discontinue reading now. Otherwise, I hope you enjoy the story. It almost feels like a dream when you're not in the middle of it. The days when you'r...

Sissy Instructions

by FrostShard on Sep 13, 2017
BDSM

Dear sissy, I trust you are preparing yourself well for our session next week. This session will be your final plunge into the realm of sissyhood. Thus far, you have simply dabbled in it, all the while essentially staying a man. All that will change starting from this session. Starting now, from the moment you finish reading this letter, one thing will cha...

The Keyholder Ch. 06

by AndreaJordan on Sep 26, 2017
BDSM

Amy returned to her flat and ran straight to her dirty laundry basket. She pulled out her orange gym shorts and unzipped the back pocket. The key! Why the hell hadn't she taken it with her to Ben's place? It had been an amazing evening, but it could have been so much better if she could have felt him inside her. At least he was hers for another day, still lo...

Lock and Key

by Teased and Denied on Sep 18, 2017
BDSM

Lock and Key: Chapter One We lay there together, sweating. Well, Tiffany much moreso than me. It was a one-night stand kind of hookup and I had figured I'd tease her for a while, bringing her to the very edge with my fingers and mouth, then backing off, making her squirm and thrash. "Shhh, you'll get your turn soon," I whispered in her ear as she desperate...

Chastity Resort Pt. 03

by handyrandy9 on Sep 25, 2017
Fetish

Anna slept for about an hour, exhausted from her explosive orgasm. I, on the other hand, was wide awake, thinking about my new found arrangement. It was a lot to take in; I still wasn't sure exactly how far Anna wanted to take this. I expected she would break by the end of the week and let me have some relief of my own. Anna showered quickly to freshen up,...

My Daring Self-Bondage Public Walk

by Gagged1 on Sep 25, 2017
BDSM

The lower floors of the parking garage are completely full, but I find an empty parking space on the third floor in front of a concrete wall and thankfully head into it. It is late Saturday morning so I surmise there are a lot of people shopping. I turn the engine off and try to relax; the journey has been quite interesting. Driving for the first time in my...

Instructions from Anne Ch. 03

by sunjimmy9810 on Sep 17, 2017
Loving Wives

Before you read this story please note that there are others that preceded it, You may want to read those as I cannot guarantee that this story will make sense. Also if you are not into cuckolding, chastity or bondage please leave -- you will hate this series. I like the feedback so bring it on good and bad. I hope you enjoy -- Also , the contract in the sto...

Marabogo: Cuckold Island Ch. 01

by eeric on Sep 19, 2017
Interracial Love

Prologue The breeze that came in from the Atlantic ocean did not do much to quell the baking sun on the beach of Marabogo. The small island laid approximately one hundred miles of the coast of Namibia, Africa. John Morton and Henry Larsen sat on the beach in their sunbathing chairs looking at all the skimpily clad women and ripped black men. Both men were...

Aphrodite's Curse Ch. 011

by Gaius8666 on Sep 15, 2017
BDSM

Standing on the bow of his ship, Demetrius was overwhelmed with feelings of sadness and loss. His status as an immortal was obviously a wonderful gift from the Goddess, a consolation prize to the curse of constant nudity and eternal frustration, but there was a catch of course. He had been away from his home now for over 53 years and did not appear to be any...

Taken Too Far Pt. 01

by SwitchSissy on Jul 2, 2018
Transsexuals & Crossdressers

I had maybe taken it a little too far. It had started as it always does, a little light crossdressing at home. Then toys as well. Then wearing something a little extra under my boy clothes when I was grocery shopping. Then when I was at work. And that leads me to my current situation. On the outside, jeans, t-shirt – normal enough. Underneath though... It w...