Gay Chastity Master Stories

3,422 results
Orientation
Length
Source
Infinite Scroll

The New Slave Ch. 10

by martin_x59 on Sep 14, 2017
Gay Male

Here is the final chapter in Daniels journey of becoming a slave. Warning, this chapter depicts rape and may not be to every one's liking. I hope you have all enjoyed reading this story as I have had writing it. I will be writing more in the future so please do keep checking back. *** It's friday and I haven't heard from Sir all week, I hate it when I don'...

Adam & Steve, Eve's Fall

by SEVERUSMAX on Sep 14, 2017
Gay Male

Steve Cahill grinned with a certain nasty pleasure at the idea of what he might do with his new slave. The poor fellow had to shower to clean up from the scat and golden showers frequently forced on him. He frankly stank like a sewer, if Steve were to be honest with Eve, the man's sadistic Mistress/wife. He gathered that poor Adam had suffered a great deal...

Master Mike Ch. 06

by mdp_2004 on Sep 14, 2017
Gay Male

In the aftermath of our tag team assault on Kevin, I stand facing my Master. Our bodies drip with perspiration while our cocks hang semi-erect and my breathing returns to normal. I'm stilling looking at the soiled rubber Master has tossed onto the slut's back. I smile broadly and then I begin to chuckle as the post-orgasm euphoria sets in. "What's so funny?...

Master Jakob and Seth Ch. 12

by and9993 on Sep 10, 2018
Gay Male

Chapter 12 - Night at the spa I felt the pressure from Master's message. I was looking forward to learning more about his magnificent body and how he likes it serviced, but it was clear from his tone that he expected me to put a lot of effort and thought in and not just guess. I feared that if he had to constantly correct me it would be annoying to him and...

You are a Sissy Pt. 07: Cuckold

by Roland15Rollin on Dec 24, 2019
Gay Male

Hello, princess. Hello again. I see you are back. That pleases me, sissy. It pleases me that you have come back for more of what only I can give you. The truth only I can give you. And we have come so far together, princess. We have come so far exploring the depths of your sissy feminine mind. And your mind is feminine. Make no mistake about it, princess....

Bobby Ch. 02

by skinnysailor on Jun 5, 2019
Gay Male

It had been several weeks since twenty six year old Bobby came to live with Mommy, Daddy and Kitten. He was fitting into the family. He and Kitten helped the servants. Unless dining with Mommy and Daddy they ate with the servants. Usually he and Kitten chose their own cloths, but today Mommy chose what she wanted them to wear. Kitten wore a long sleeve hig...

His Plaything Pt. 01

by Cumpup39 on May 22, 2019
Gay Male

The hotel door was unlocked and open just slightly as he ordered. I was on my knees, hands behind my back, facing the door. My body was freshly shaved and my aching cock was bulging painfully inside my steel chastity cage, the only thing I was wearing besides my collar. Sir would be here very soon and would find me just as he wanted. This would be my first...

Descent into Depravity

by HerLittlePiggy on Sep 14, 2017
Gay Male

Sun streamed into my hotel room, waking me from my alcohol aided slumber. My head ached, my mouth was dry and my memory of the night before was spotty at best. I heard the shower in my room running and confusion set in. I had come to the conference alone and I had no idea who could be showering in my room. I recalled talking to a woman named Janice early at...

Master Comes on Sunday

by Cap_N_PieSissy on Dec 9, 2019
Gay Male

My Master is much younger than I am, and it would be entirely accurate to describe him as a twink. Small, lithe without an ounce of body fat in him apart from a certain softness of his facial features, and packaged in soft, smooth hairless skin. He fully enjoys all the greatest blessings of youth, but there is a devil in him. He found me on the internet. I...

Oliver's Balls Ch. 03

by newbitime on Sep 15, 2017
Gay Male

It had been just over a year since Oliver had taken control over my life. And control it he did. I went from being a promising young salesman, to an assistant, who handled all of my boss' accounts, and also served as his cock slave. Oliver had moved into a much larger penthouse apartment, while I was struggling to feed myself on a weekly basis. Not only was...