Gay Sissy Chastity Stories

970 results
Orientation
Length
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Infinite Scroll

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...

A Kept Sissy Boy

by keptsissy on Sep 19, 2017
Gay Male

"You need your butt paddled, don't you?" When I responded to his 'Dominant Male' ad I knew what I wanted, what I might be in for. I masturbate to nothing other than being used by a real man. But I didn't know this man would exploit that completely at the time, be as good at it, as addictive as he is, make me his full time sissy 'girl'. It started out two...

Stick Shift: C.S.P.

by zackjack on Sep 14, 2017
Gay Male

I watched, rigid dick in hand, as the smaller man squatted in front of the handsome stud who hit the vape cig between his fingers in obvious expectancy of some good head. Both men's ebony skin aided their blending into the shadows which added to the mystique of my visual. The diminutive dicksucker knew his way around dicks in general and this 'cocksucker pa...

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...

This Thing Called Life Ch. 05

by noodneighbor on Sep 14, 2017
Gay Male

The ride back from the frat to the hotel was a whirlwind of information and feelings. The ladies were celebrating my first job and saying how well I did though Ashley teased that she missed my "tits" which were now sitting in the back of our vehicle. Flavia, pressed against me in the back seat suggested she liked me both ways just fine, which I enjoyed until...

My New Daddy Ch. 01

by sissytoy20 on Feb 13, 2018
Gay Male

I'm 21 years old and I attend college but I still live at home for financial reasons. I've always been fem and young-looking for my age. I like to cross dress, but I don't usually dress fem in public. I've just found that it can be difficult for some straight folks to take a young male who likes to be a sissy slut. So you can imagine my surprise when I was r...

It Could Be Worse Ch. 06

by eviltwin52 on Sep 14, 2017
Gay Male

In chapter 5 Leon took control of what he called his new sissy and fucked Cin into submission. We both became addicted to his superior black cock. Besides falling for his cock, Leon's predatory nature was evident. He wants Cin and I to prostitute ourselves for him. In the throes of black cock lust, we agreed. It could be worse Part 6 "Did you remember t...

I Turned Myself Out Ch. 04

by drmweaver705 on Sep 14, 2020
Gay Male

All characters are over 18. This story contains bisexual and cuckolding activity as well as fetishistic name-calling. If you don't enjoy these things, this might not be the story for you. *** Porn seduced me early in life and, even as a married man, it commands part of my loyalty to this day. It happened that I became bored, or maybe just desensitized, to...

Fantasy Out Of Control

by gbr2004 on Aug 18, 2017
Gay Male

I'm a divorced man living in Las Vegas. Recently retired, live alone and live a relatively normal life. I'm in decent shape for my age, 5'8", 180, and stocky build. I have been straight for the majority of my life. For the last few years, I have started to think more about getting together with another man. It goes beyond just this, as I want to be submissiv...