Gay Chastity Maid Stories

645 results
Orientation
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Infinite Scroll

Fixing the straights

by cdbaby on Dec 28, 2016
Gay

You wake up and prepare for your day, unaware that this would be the last day you would be considered straight. You shower as you did every morning and felt the water's warm touch as it cascaded over your skin. You could stay here forever if you could. But you need to start your day and the hot water would run out before long. You wash your hair, then the re...

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The Hole

by iamacocksucker on Sep 14, 2017
Gay Male

(Message written to an online forum) Hello, gentlemen. I found this awesome forum just a little while ago, and I thought I'd introduce myself. I don't have a real name any more, but I am addressed most frequently as "hole" and "cumdump." Actually, although you can't see it in the picture below, "cumdump" is tattooed on my back. So, about me: I am twenty-fi...

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...

Enticed and Humiliated Ch. 13

by FantasizeAndRealize on Sep 14, 2017
Gay Male

Part 13 - Debased Spring Break Frolics - Back at Chokers I went home that night feeling so proud of myself. Glen had actually told me that I cleaned up good! I also loved the humiliation that he was dishing out to me. I don't know why but my dick would almost erupt in orgasm when he humiliated me in front of his two friends. It made me feel like a real subm...

Nephew's Readjustment Pt. 15

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. ***** Nicholas was able to refrain from masturbating that night and the next morning, but only because of the tenderness of his ass. Without access to his genita...

The Pet Ch. 02

by Gman26 on Aug 18, 2017
Gay Male

Leave real feedback or don't comment at all. Indecent comments will be flagged for the webmaster. ***** I found myself in master's basement with two chairs sitting in front of me. Voices upstairs are definitely my parents. Mom sounds like she's crying. "This isn't how I wanted it to happen!... My baby boy." She doesn't seem to want to come down. Dad sound...

Gay Lovin' Gone Bad

by Ciceri on Aug 18, 2017
Gay Male

I have always been turned on by the lash or whip. Even when I was a teenager I wasn't so repelled by the idea of slavery merely because the whip was often used. Of course, slavery is bad. I knew there was an occasions when two or more consenting adults got together and used a whip. I just did not know when. I grew older and became aware of such occasions thr...

Guys' Retreat Pt. 03

by Cyanlot on Jan 20, 2020
Gay Male

Part 3: Serving I don't know when Vince came into the bedroom. Amazingly, I got to sleep quickly and slept soundly until about 7:00, when light came streaming into the room. I looked over and saw that Vince was still asleep in his bed. I didn't want that to change so I very quietly got my clothes together and tiptoed to the bathroom for a shower. A long ho...

Naughty Boy Ch. 02

by fantaseeboy on Sep 1, 2017
Gay Male

I'd always been embarrassed and ashamed of my body. I suppose I had an image of what a guy is supposed to look like in my head, and that isn't me at all. I had to look up at nearly everyone I'd ever known. The first time Sam picked me up in his arms he laughed and said I couldn't weigh more than a buck soaking wet! Well, that's not quite true, but it's close...

Progression Ch. 08: Introduction

by klapperz on Mar 28, 2018
Gay Male

Nathan woke up next to Kevin, who was wearing only his briefs. It had been a week since he had invited Kevin to meet Jack and Ryan, and it was time to visit them for another session. It was now over a month since Nathan last had an orgasm, and he could feel the cum built up in his balls. Nathan got out of bed and went into the bathroom to take his shower....