Gay Progression Chastity Stories

435 results
Orientation
Length
Source
Infinite Scroll

Power Trip Ch. 04

by Wally_West on Sep 18, 2017
Gay Male

Reader Warning: Over the course of several chapters this story will contain cuckoldry, forced-bi, male chastity, humiliation, and other female domination themes. These kinks are not for everyone; if you do not enjoy FemDom themes you will not enjoy this story. * A week had passed since Colin had sucked his first cock in the glory hole. Veronica had held hi...

Are You Game? Ch. 04

by 2ndAlias on Sep 14, 2017
Gay Male

Pro Bowl ---Sunday Ben greeted me at the door that afternoon with an extended hug and I instantly became hard. Ever since last week, or perhaps even before, my dick had somehow become accustomed to springing to life whenever I was in forty feet of him. "It's just the two of us," Ben said as he affectionately rubbed the back of my neck. "You want a drink...

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...

The Male Room

by WatchingAndWaiting on Aug 18, 2017
Gay Male

This is the story of my first time with a man. And my last time... So far. I was always curious, even when I was very young. Looking at men in magazines, especially if they were in revealing underwear and had big, well-defined bulges. I had messed around a little as a kid, but nothing more serious than 'you show me yours and I'll show you mine'. But as the 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...

The Brotherhood

by sr71plt on Aug 18, 2017
Gay Male

Alfons delivered another tankard of beer to the well-dressed gentleman seated at the best table, near the fireplace. It still ranked as the best, with the most substantial chair, even though the table was functionally only the best in the winter, when a fire was going, not now, in high summer. When he set the beer down, the man grabbed Alfons's hand and didn...

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...

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...

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...