Gay Chastity Cage Sissy Stories

1,568 results
Orientation
Length
Source
Infinite Scroll

The Backpacking Trip Ch. 01

by lockedinsteel on Nov 21, 2017
Gay Male

"It's what I want for you baby," said Jamie. Her husband, Daniel, was still a little uneasy with the idea. "I know you've wanted to explore that for years and I think that if you get the opportunity you should. In fact, I'm giving you an order. Do it if you get the chance. Promise me!" she told him. "Okay, Okay I get it. I promise, my love," he replied....

A Kept Sissy Boy

by keptsissy on Sep 19, 2017
Gay Male

"You need your butt paddled, don't you?" When I responded to his 'Dominant Male' ad I knew what I wanted, what I might be in for. I masturbate to nothing other than being used by a real man. But I didn't know this man would exploit that completely at the time, be as good at it, as addictive as he is, make me his full time sissy 'girl'. It started out two...

The New Slave Ch. 05

by martin_x59 on Sep 14, 2017
Gay Male

I would like to start by saying I am new to writing so I hope you don't judge me too hard on my literary naivety. Nor am I experienced in Bondage or Master Slave relationships. This story is pure fantasy from my part and is about what I find erotic and stimulating. Please bear this in mind when reading the story. I hope you find it as stimulating reading as...

The Master and Slaves Playtime

by LthrBndBy on Jun 9, 2020
Gay Male

As in every single one of my stories, all characters are over 18, and fully consenting adults. This story is purely fictional on all accounts. Enjoy. ————————————————————- Here I am, in all my "glory" so to speak, kneeling on the floor of the closet in our bedroom. My arms stretched out to either side to the walls, my mitts clipped to the rings discreetly...

Nephew's Readjustment Pt. 04

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, mind fucking and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. Comments, ideas and feedback are welcomed and sought after! ***** Lying in bed that night, Nicholas' mind wouldn't quiet. He kept trying different p...

My Time in the Monastery

by brownmonkk on Aug 18, 2017
Gay Male

Brother / Sister/Slave, ("TML") November 1970 "Good loving & Good Scourging" The story of a MASTER and his slave! WOW, "it" finally happened!!! I had had my first sex, and it was with a fellow brother monk in the monastery. It was great. I always imagined having my "first time" with a sexy gal, but nonetheless my first sex was great! I often fantasize and...

Claiming Evyn Ch. 01

by Domina_Jen on Aug 30, 2017
Gay Male

Note to readers: This story contains nonconsensual sex between men. If nonconsent or reluctance isn't your thing, feel free to move on. Otherwise, enjoy. ***** Evyn slumped down against his door, holding his head in his hands and quivering all over. He knew it was coming tonight. He'd just seen Jeremy in the hall, he'd seen that hungry look in the man'...

The New Order Pt. 03

by Iamkrazy4 on Dec 16, 2019
Gay Male

Part 3: My ass, my mouth, my job No, the guidance counselor didn't fuck me. Though, I would have let him. But, that says more about me than it does about him. What he did do was praise my on stage performance and say I the most enthusiastic "volunteer" so far. He complimented my dick taking abilities and described how my life would be from there on out. Th...

His Plaything Pt. 03

by Cumpup39 on Jun 5, 2019
Gay Male

I considered my current situation. I was standing naked in a hotel hallway, wearing only a stainless steel chastity cage that contained my throbbing and swollen cock. I had a load of dried cum on my face that had been left there by a man I only knew as Master. He came to my room, handcuffed me and fed me his cock and cum, except for the part of the load I n...

Confessions of a Chastity Slave

by deviator on Aug 31, 2017
Gay Male

It's hard to believe it all started with some talk on a chat room. I was in college then, and always straight in real life, although not very successful with the ladies. But my dirty little secret was that I liked to go online and indulge my fantasy: being enslaved, feminized, and kept in chastity by a man. At first, I'd wander through chat rooms and find a...