Gay Chastity Milking Stories

1,806 results
Orientation
Length
Source
Infinite Scroll

Chase Becomes Chaste Ch. 02

by growing_interest on Aug 22, 2017
Gay Male

Chapter synopsis: While Chase loses his property and his dignity, our narrator takes possession of his new condo and his new boy. *********** The movers arrived bright and early. I had just awoken from a pleasant sleep, dreaming all night of how I could punish Chase next. I felt refreshed and empowered once more. It was that same sense of certainty that ga...

The Trio Ch. 01

by Fafantasiz3 on Feb 25, 2019
Gay Male

When The Man returned from work the boys were at play, David thrusting deeply and powerfully into Sasha's perfect round bubble butt, enjoying the sight of his lover's sore ass. He had been whipping it again, and he could see the blonde 20-something who was currently arched and getting thoroughly fucked by his other 20-something lover had been crying, and moa...

Hell slave

by Pantherking on Mar 4, 2019
Gay

You are a slave in hell. A lowly toy for Master Asmodeus to use. Your pathetic cock locked forever in Chastity, and constantly edged. You'll never know release. You'll live your eternal existence serving your master, and loving every second. Right now we will decide what species of slave you are.What's next? Rat What's next? Rat...

Open in Reader

Influencer to Sex Slave Ch. 02

by dreamymark9 on May 15, 2019
Gay Male

Author's note: This is erotic fantasy and completely fictional. The main character, Jack, is a fictional, generic social media star / influencer, and is not a real person. As always, would love to get feedback in comments and messages. ***** Jack wakes up naked in bed, being spooned by his master, in his Airbnb in LA. Recent events still kind of feel like...

Progression Ch. 11: Goodbye

by klapperz on Jun 18, 2018
Gay Male

"Welcome home," said Kevin as Nathan pulled the car into the driveway of his home. "It feels like I've been away longer than a week," said Nathan. Nathan opened the door and let Kevin into the house. "Welcome back, how was the holiday?" said Jeff calling out from the living room. "Oh yeah, I told Jeff we went away for a week holiday. Just play along. Or...

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...

Deviants in Chaste

by IsleyOfTheNorth on Jan 17, 2019
Gay

Author's Note: I've been working on another project. This story will be on hiatus for the time being. The monk was shivering. It was a bright summer's day outside the small council room with the heat of mid-July scorching through its wide balcony. Beams of harsh light lit all corners of the room yet still the novice appeared pale and near sickly blue. He sp...

Open in Reader

First Scene

by kinkfiction on Jan 15, 2019
Gay Male

It all depends on you in the end. You need to decide if you want to take pride in your submission or do you want to be humiliated by it. Would you like to be treated like a prized possession, to be placed in ways I find pleasing and, in exchange, have all your needs be met at my whims? Or do you want to be treated like a slut, to be taken as many times and b...

Liam's Submission Tested Pt. 02

by PupTracer on Sep 14, 2020
Gay Male

"Shower," Marcus pointed to the corner of the blue tiled bathroom. "And face the wall, I love the look of your reddened ass." I complied, setting the water to cold, both to stop my cock from getting hard under Marcus' gaze and to soothe the burn in my ass. He left and then returned with my bag and instructed me to change into gear. "I'll be waiting for you i...

Amy Cuckold Brian Ch. 05

by CuckoldGuy on Sep 19, 2017
Gay Male

"Honey, while I was upstairs changing, I went into our bathroom and I saw your douche bag hanging there. Are you having any kind of a problem?" Asked Brian. Setting the dinner table, Amy replied, "No I'm not but let's talk about it later. Will you tell the kids that dinner is ready?" "Sure thing", replied Brian. Later that evening after the children were...