Gay Femdom Chastity Stories

302 results
Orientation
Length
Source
Infinite Scroll

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...

An Average Day

by Closetfaggotnyc on Aug 18, 2017
Gay Male

This is how an average day goes for me. In addition to being a closet faggot and a liar, I'm also a loser and a chronic masturbator. I'm a loser because I really don't have friends any more after lying so much for the last few years. My friends would call me on a Friday night and invite me out for drinks or to hang out or whatever. But because of my cock a...

Progression Ch. 04: A Real Fitting

by klapperz on Mar 6, 2018
Gay Male

Nathan hung out with Jeff and his other flatmates for the day. He had been so focused on Ryan and Jack that it was nice to have a break and be normal for the day. They went to the pub for lunch and then watched some films. Before he knew it, the day was over and everyone was heading for bed. The next morning Nathan woke up for work. He panicked, remembering...

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...

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...

Cum Delivery

by Patrick2380 on Jan 21, 2020
Gay Male

I had the house completely to myself, a rarity these days. Literally, no one would be home until the next day. Not needing to worry about any possible interruptions, I decided I was going to have an epic masturbation session. Back when I was single and lived alone, I could watch porn and jerk off for hours at a time. So after having a little breakfast and...

My life changed quickly Pt. 01

by elboriqua on Mar 30, 2020
Gay Male

Hello dear reader. My name is Charles. I am 47 years old, a divorced father of two grown kids, Charles, Jr and Chelsea. I work in IT in a senior position for a contracting firm. I make a decent living, low 6 figures, and have a pretty comfortable life. Until bout two years ago I had a comfortable, boring life. After my divorce about 10 years ago I had done...

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. 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...

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...