Gay Femboy Chastity Stories

301 results
Orientation
Length
Source
Infinite Scroll

Discovered by a Black Guy

by chastity_sissy on Sep 14, 2017
Gay Male

I should preface this story by saying I've never identified myself as homosexual, but sometimes after being locked up in chastity for a long time combined with crossdressing, I must admit to some fantasies involving other men. I never expected anything to ever actually happen, and it's my own fault really. I had been paying a beautiful, very sexually fetis...

Progression Ch. 02: Regret

by klapperz on Mar 6, 2018
Gay Male

The next few weeks Nathan went back to normal. Wake up, Work, Wank, Sleep. Almost forgetting about his encounter with Ryan. It wasn't until a month later that his urges to lock up his cock would come back. He started to remember Nathan and his offer. "He did say I didn't have to show my face" he thought to himself trying to ease his shyness. He pulled open...

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...

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...

Prince Gyllen Ch. 03

by MythMaker on Sep 19, 2017
Gay Male

A couple of days had passed since Gyllen's fellatio fiasco in the Monster District. Though he may have looked like a sweet young man from the outside, behind closed doors he was slowly but surely turning into quite the little tart, replaying the scene over and over again in his head while he masturbated for the following nights, thinking about the exotic non...

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...

Sexy Filipino Nurse

by xploring96 on Sep 14, 2017
Gay Male

The following story uses derogatory terms for gay men. If this offends you do not read any further. This is my first story. Any feedback is appreciated. ***** I was in the Emergency room at Mercy Hospital having brought my elderly mother in. While we waited for a doctor, the nurse came in. A tiny Filipino man. At about only 5'3" maybe 120 lbs, boy almost...

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...

Straight to Bi, Cam to Real Life

by dlcalguy on Aug 18, 2017
Gay Male

After I finished university, I struggled for a good-paying job and money was tight. But I couldn't face living back at home. I managed to find a room to myself in a house-share with two other guys and three women. We were mostly in our early twenties and doing various entry-level jobs. One guy, Pete, was older. About 45. He was on a temporary assignment in o...

Damaged Goods

by NRMathis on Dec 10, 2018
Gay Male

For about the twentieth time, I seriously considered getting up and running away while I still had the chance. The only thing that stopped me from escaping the restaurant was the fact that if I did, I would be blowing this Scott guy off. I didn't even want to be on this blind date, but everything happened so fast. Kaleb, one of the men working with me at C...