Gay Chastity Anal Stories

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Infinite Scroll

Progression Ch. 01: Finally

by klapperz on Oct 15, 2017
Gay Male

Nathan paced around the shop for a few minutes while building up the courage to purchase the chastity device. This was his first time inside a sex shop, and he was very uncomfortable. He saw shelves full of different toys, each one exiting his mind with sexual thoughts. He noticed the device he wanted was behind the counter, but in order to seem less awkward...

Forced Slutty Transformation Ch. 01

by beachboi_3 on Sep 14, 2017
Gay Male

Small towns are all the same. Racists, cows, and that one weird racist guy who sleeps with the cows. Personally, I just wanted to leave my town. My name is Carter, and this is how I went from promising high school student with a bright future, to a strung out slut, desperate for sex. I'm white, about 6 feet tall, and I'm built like a swimmer. That is, fairly...

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...

Progression Ch. 13: Unboxed

by klapperz on Jul 3, 2018
Gay Male

Nathan woke up and as usual, removed his t-shirt and briefs then made his way to the bathroom. On his knees, he waited for Kevin to arrive to prepare him for the day. Kevin was frequently late, and today was no exception. Nathan waited patiently for twenty minutes until Kevin finally opened the door and with his phone angled to take a picture. "Smile for y...

Cherry's Graduation Party

by CherryWood on Aug 30, 2017
Gay Male

I finish applying my lipstick and take one last look at myself in the mirror. I'm almost stunned at the reflection that stares back at me. After months of training and feminization I look like the perfect slutty fuck toy. I feel my little cock begin to get hard and strain against my chastity device as I look over my changed body. The strict exercise regimen...

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...

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...

Caged Heat

by HerLittlePiggy on Sep 14, 2017
Gay Male

He looked at me with a sharp menacing stare and a shiver ran down my spine. I wasn't sure what I was doing or what I'd gotten myself into but I feared that I may have made a terrible mistake. He stepped closer with his intelligent eyes affixed with mine and my stomach started to churn. My eyes traveled down his half naked body on their way to their rightfu...

Master Comes on Sunday

by Cap_N_PieSissy on Dec 9, 2019
Gay Male

My Master is much younger than I am, and it would be entirely accurate to describe him as a twink. Small, lithe without an ounce of body fat in him apart from a certain softness of his facial features, and packaged in soft, smooth hairless skin. He fully enjoys all the greatest blessings of youth, but there is a devil in him. He found me on the internet. I...

Progression Ch. 09: Punishment

by klapperz on May 1, 2018
Gay Male

Once again Nathan found himself lying awake beside Kevin, who was sound asleep. All that was running through Nathan's mind was having Kevin's cock thrust into his ass. Unable to sleep, Nathan sat up and turned on his laptop to watch some porn. He logged into Ryan and Jacks porn channel and watched the videos. Each one made his cock fill the cage more each t...