Gay Femboy Chastity Stories

301 results
Orientation
Length
Source
Infinite Scroll

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...

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...

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...

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...

On No He Didn't

by felicia_rene on Sep 21, 2020
Gay Male

Description This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy safely. Rick a tall well-built handsome entertainer catches the eye of his boss as he works at his night club. The man's lust consumes him and he conspires to twist him and make Rick his bottom. Despite the fact that Rick insists that he was a...