Gay Chastity Pup Stories

494 results
Orientation
Length
Source
Infinite Scroll

Progression Ch. 03: The Show

by klapperz on Mar 6, 2018
Gay Male

Nathan turned and looked at his clock. It was barely 3am and he was just lying there looking at the ceiling. No matter how hard he tried he couldn't stop thinking about his session with Ryan and Jack. He put his hands under the blanket to feel his cocks prison and attempt to get some relief, but it was useless. When he tried to play with himself his cock jus...

Pretender's Fate Ch. 05

by KeithD on Nov 4, 2019
Gay Male

"They are still going to be there in the morning, Willy. Come back to the bed." "Do you think that Roxburgh can be saved if I just walk out there and surrender to them?" the young William Howard mused. It was the year 1314 in the northeast of Scotland, and Robert the Bruce had been king of Scots for eight years. He had been using that time to cajole or bur...

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...

Progression Ch. 07: Decision

by klapperz on Mar 28, 2018
Gay Male

The next few days went pretty slow as Nathan counted the minutes until he could see Jack and Ryan again. It didn't help his frustration than Kevin, who was now sleeping in his bed, had quite a high sex drive. He was always demanding handjobs and blowjobs, which kept Nathan in a constant state of arousal. "I'm off to see the guy I told you about," said Natha...

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...

A Night at the Movie turned me Gay Pt. 02

by jamtby on Oct 12, 2020
Gay Male

Entering the room immediately caused my stomach to churn with excitement. Something about entering a place where strangers are in control and you anticipate being involved with sexual activities. The what, why, and how remained a mystery. This only added to the combination of nervousness and excitement. The woman with a strangely deep voice said, "Welcome...

Runt and Giant

by NRMathis on Jul 31, 2018
Gay Male

It was dawn on a summer day in a forest in Idaho when Paine spotted the body floating in the river. He had gone out hoping to catch some fish. He didn't need to live off the land, but he liked doing it whenever possible. It meant that he didn't need to go to civilization as often. He had arrived only minutes before and was busy attaching his lure when he sa...

The New Slave Ch. 07

by martin_x59 on Sep 14, 2017
Gay Male

I would like to thank all your positive comments. I'm really glad you are enjoying this series. I have just written a new short story that I think you may all like, please keep checking back. I intend to post it next week. In the meantime here are some instalments in Daniels journey into being a slave. *** College is slow today, I'm finding it difficult t...

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...

A Life Not Spent With You Ch. 04

by Rinique on Sep 19, 2017
Gay Male

************************** The young man began to tremble again, snuggling deeper into his arms with a barely audible gasp. Cooing softly, Ivan brought the blankets up around himself and his lover, taking a moment to caress Damien's cheek before wrapping his arm around the other again. Within minutes, he realized the trembling wasn't from the cold, Damien's...