Gay Chastity Cage Milking Stories

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Bathhouse Chastity Bitch

by Cumpup39 on Feb 11, 2019
Gay Male

I'm a married man in my early 40's, I'm 5' 7" in good shape and have a great wife and two kids. I also have a secret, I'm an absolute cum whore! I love everything about being used by men! I love being manhandled, degraded, covered in cum, piss and spit. My favorite kink is being sexually humiliated in public, in front of strangers. My wife would never beli...

Turning Myself Gay Pt. 03

by bart_allen on May 29, 2018
Gay Male

To my mutual humiliation and arousal, the next morning at work, Marie could instantly tell. Truth was, I could see why: Nathan had fucked me three god damn times, and I my ass was sore as hell. Sure, he'd been tender as well at times, but one look at me and she knew. She just rolled her eyes at me, causing me to blush. She wanted to know what he looked like,...

On No He Didn't

by felicia_rene on Sep 21, 2020
Gay Male

Description This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy safely. Rick a tall well-built handsome entertainer catches the eye of his boss as he works at his night club. The man's lust consumes him and he conspires to twist him and make Rick his bottom. Despite the fact that Rick insists that he was a...

Nephew's Readjustment Pt. 13

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. * The next weekend, Cynthia called her nephew over in the afternoon. It was time to start preparing him for the next phase in her ever growing plans. She knew th...

Cum Over

by sickoboy on Oct 22, 2019
Gay Male

Damian walked out into the sunlight and immediately felt the humidity in the air. The contrast from air conditioning to summer afternoon was like a rolling oven blast. Damian had thrown on a cotton Hawaiian shirt, and a pair of jean shorts, frayed at the cut offs. On his plump feet, he wore a pair of sandals. Today Damian was going commando. As the heat boun...

Temporarily Dickless

by AssWhisperer on Sep 14, 2017
Gay Male

[Warning: This is a very sexually dark story. Fisting, watersports, medplay, implied body modification, chastity. My thanks to Kenji De Sade for his encouraging me to write this story after a series of conversations about chastity.] How had I come to be here? I wondered as I floated in orgasmic bliss. It had started with my impulsively writing a guy on...

Enslaved by Myself Ch. 03

by Lausunaht on Sep 14, 2020
Gay Male

I was dreading what was about to happen. My master was going to hurt me badly to ensure I would never rebel. I knew this for certain because I would do exactly the same if the roles were reversed. I could only hope that my affection for myself was strong enough to limit the pain. He left me tied up alone for hours, I was thirsty as I didn't drink the whole n...

First Time Fucked

by tinywhiteboi on Aug 18, 2017
Gay Male

It's a long story but I had by now been the chastised slave to my former Mistress for over 6 months. Over that time I'd been conditioned to be more and more subservient. She seemed to take particular pleasure in humiliating me in front of others, especially her friends. Most Friday nights she'd have a gathering at her house with 2 or 3 friends. I would serv...

Top Becomes a Daddy Bear's Boy Pt. 02

by DaddyBearChaser on Jul 6, 2020
Gay Male

Mike woke up in the morning and gave his new boy a tight squeeze, nuzzling his beard and nose into his boy's smooth neck. "Boy it's morning, time for you to get up and take care of my needs," he said softly in his deep grizzly voice. I woke up being squeezed and spoken to, not knowing what was going on I tried to get up. I felt big arms wrapped around me an...

Power Trip Ch. 04

by Wally_West on Sep 18, 2017
Gay Male

Reader Warning: Over the course of several chapters this story will contain cuckoldry, forced-bi, male chastity, humiliation, and other female domination themes. These kinks are not for everyone; if you do not enjoy FemDom themes you will not enjoy this story. * A week had passed since Colin had sucked his first cock in the glory hole. Veronica had held hi...