Gay Chastity Cage Milking Stories

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Infinite Scroll

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...

The Making of a Master

by Littlepoppyhole on Oct 6, 2020
Gay Male

David lay on the dishevelled bed exhausted and still sweating after his recent sexual encounter with a man called Raymond. His hole was leaking semen onto the bed sheets. The sheets also gave off the aroma of anal mucus. This did not perturb David as he was deep in thought about the man he had served. He thought there was room for improvement in his sexual i...

Master Jakob and Seth

by and9993 on Jul 11, 2018
Gay Male

Master Jakob Chapter 1 - Seth meets Master Jakob and Zach and starts his new life as a slave Training Day 1 - Saturday I was on the way to finally start my life as a slave for Master Jakob (MJ). My given birth name was Andrew but as part of the slavery I was given the name Seth. His name is Jakob or Sir to me. He's 6'4" tall with brown hair and the most...

The Apocalypse

by realizingworlds on Jun 17, 2015
Gay

Your name is Lexus Halpas and you are one of the last men born from a woman after a strange disease wiped them out. Your father didn't take her death well and he became even more distraught when he learned that you would never know your grandmothers, your aunts, or many of your cousins. As his only child, he's hidden you from most of the world and tried to k...

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Pretty Boy

by today_i_am26 on Jul 13, 2020
Gay Male

"Aren't you a pretty boy?" He said with a leering grin. I was on my second day of my new job and I had been tasked to drive the van to an industrial estate in the rougher end of town to collect some items and drop them off to the customer. I had walked through into the warehouse where I was confronted by a man in his late 40's with a strong accent, tattoos,...

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...

The Male Room

by WatchingAndWaiting on Aug 18, 2017
Gay Male

This is the story of my first time with a man. And my last time... So far. I was always curious, even when I was very young. Looking at men in magazines, especially if they were in revealing underwear and had big, well-defined bulges. I had messed around a little as a kid, but nothing more serious than 'you show me yours and I'll show you mine'. But as the y...

Bobby

by skinnysailor on Jan 28, 2019
Gay Male

Every morning started the same. The harsh bell sounded and the lights came on. Roberto whimpered. It was a beautiful dream. They were in a grassy park. The sky was blue, the clouds fluffy white. He was wearing a pretty pink sundress. Damon was laying on his back wearing only a white dinner jacket. He was kneeling between Damon's knees. Damon's big black coc...

A Weekend of Servitude

by HerLittlePiggy on Sep 14, 2017
Gay Male

Thank you Susurrus for the help editing this monster. ***** Richard Michael Quail, Rich to his family and friends, Mr. Quail to his associates and adversaries, sat quietly at the round high top table beside his sexy, buxom wife and sipped on a fine 18 year old single malt scotch. They were both well dressed: she in an expensive blue designer dress which d...

Blink: Four

by KenjiDeSade on Aug 18, 2017
Gay Male

The following story is a fictional account. The characters are entirely unreal and so are their situations. Thus no direct attention was paid to probability or safety for the characters. Such practices should not transfer over to real life situations. Practice safe, sane and consensual sex. For your own damn good. If you have problems or issues with queer po...