Gay Chastity Stories

271 results
Orientation
Length
Source
Infinite Scroll

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...

Hotel Whore

by Cumpup39 on Apr 17, 2019
Gay Male

I was in the city for a business trip, but wanted to spend some time serving cock while I was there! I am a married bi guy who is married to a great woman, but I have another side... I am a submissive, cocksucking whore for men! I love sucking and taking cock, cum, piss and spit. I love being dominated, humiliated and degraded. I am a genuine cum, piss and s...

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...

Master Jakob and Seth Ch. 09

by and9993 on Aug 13, 2018
Gay Male

After putting my butt plug in I went back upstairs. I hit the app on my phone which reinflated it to the last setting by Master. He warned me about the soreness and he was right. I had never felt this type of internal soreness before. Even my dick felt like I had spent the last hour cumming. Although I wanted to take advil, I understood where Master was comi...

Fun and Games Ch. 02

by Arten10 on Sep 2, 2017
Gay Male

Fun and Games - Chapter 02 Recap: As Leon didn't know anywhere near as much about the gear you can get, Jason showed Leon some websites that had loads of different stuff on - gags, clamps, restraints and numerous other things to secure a guys balls with. You name it and these websites had it! Leon couldn't believe this. With every day that went past, Leon'...

An Evening with Master

by SlaveJ2718 on Aug 18, 2017
Gay Male

I stood at the corner, looking down the block to Master's house. The bright May sun and the cloudless sky stood in stark contrast to the thoughts running through my head. "Sir will be expecting me. I can't stand here all day. I can do this. I have to do this," I thought. I had just walked up the hill from the train station, like I do every evening after work...

Submissive Sissy for 'Her' Man

by keptsissy on Sep 28, 2020
Gay Male

He toys with the lace ruffles on my panties. His fingers move over the ruffles and up and down the crack of my butt. I flick my tongue over the hole of his erection and then take it deeply into my mouth, holding it at the base straight up. His eyes are closed as he lays naked on the bed, his huge hard cock sticking up off of him. I start to pump, start to ma...

Collateral Ch. 05

by laurasfox on May 1, 2018
Gay Male

Jake was getting restless. There was no TV or other means of entertainment he could use while waiting for that annoying bastard. He had a mind to just get out of the house, but he didn't want Klaus to chase him down from the first day. There was enough time to observe his surroundings later. For now, he had to admit he was very curious about this insanely ri...

March Madness Ch. 07

by watchdwag on Sep 14, 2017
Gay Male

It felt really weird waking up beside another man in my bed. My ass was pressed against Larry's cock as I woke with his arm gently draped across my waist. It was a position to which I was accustomed with my girlfriend Sandy as she would often cuddle close to me in a spoon position in the bed. I looked over and Larry appeared to be dead to the world as I pull...

My Neighbor Made Me Do It Ch. 07

by CapnSteelBoy on Sep 28, 2020
Gay Male

My Neighbor Made Me Do It Ch. 7 by: CapnSteelBoy Thanks again to all the readers out there! I hope this spicy chapter relieves some of your own tension! Don't forget to like and comment, I want to know what you think. Feel free to message me instead if you hate the idea of public comments. Cheers! --------------------------------------------------- Chapt...