Gay Chastity Progression Stories

435 results
Orientation
Length
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Infinite Scroll

A Furry Ass Slut Boy for Daddies

by playinmine on Oct 15, 2017
Gay Male

Yes, my ass is indeed furry, which is something I had always found a turn off myself, but I have learned that quite a few men prefer that. It was a bit strange for me, at first, to receive fan messages from guys that were turned on by it on adult social sites. Usually it was a request for a pic and I'd send (and still do) one of my furry ass, exposed in crot...

Cyber to Reality Ch. 01

by Ponty on Aug 18, 2017
Gay Male

I had always been curious, but much too engrained in the straight guy perception of all things gay. The gay community was all hairdressers and limp wristed wimp types. Perhaps it was my protection against my curiosity, I was not at all like that so I must be 100% straight. I ignored the obvious signs that did not fit the image. The fact that my first wank w...

Intrusion Ch. 01

by Allivrain on Aug 31, 2017
Gay Male

The alarm clock on the nightstand blinked, 4:15am. It was a warm night, the blankets had been kicked away into a tangled mess sometime earlier and the young man that lay on the bed wore only a threadbare pair of sweatpants. Taylor was on his side, asleep and facing the wall with a peaceful expression. He was exhausted, college and his job barely left him any...

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...

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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...

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...

Turning Myself Gay Pt. 03

by bart_allen on May 29, 2018
Gay Male

To my mutual humiliation and arousal, the next morning at work, Marie could instantly tell. Truth was, I could see why: Nathan had fucked me three god damn times, and I my ass was sore as hell. Sure, he'd been tender as well at times, but one look at me and she knew. She just rolled her eyes at me, causing me to blush. She wanted to know what he looked like,...

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...

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