Gay Sissy Chastity Stories

970 results
Orientation
Length
Source
Infinite Scroll

Infection Pt. 01

by TheStoryBoi on Aug 31, 2017
Gay Male

All characters in the following story are above the age of 18. The events and circumstances are entirely fictional and should not be re-enacted in the real world outside of consensual role-play. Always be safe, always get consent, and always take care of your partners. ***** Chapter One Mark raised his voice to be heard above the noise, "I can't take t...

Mr. One Fifty-Eight Ch. 01

by tazemebro on Sep 14, 2017
Gay Male

Mr. One Fifty-Eight picks up where Chris Donaldson left off. Chris Donaldson and Justin Corvino were roommates during their sophomore year in college, which has just ended. Justin began the year by forcing Chris to suck his cock, and their daily sexual activity gradually grew into an intense, Dom/sub oriented relationship. Chris' feelings for Justin deepened...

New Horizons

by Pelaam on Sep 16, 2017
Gay Male

Pelaam October 2007. * Captain Diego Alverez strolled jauntily through the colourful marketplace. Occasionally a stallholder would call out a greeting and the buccaneer would shout his reply or simply doff his red, feathered hat and affect a sweeping bow. He smiled widely. The financial success from his last cargo had been safely salted away, the swashbuck...

Anonymous Guest

by RalphyNJ on Aug 18, 2017
Gay Male

(Note to the reader: This is a revised and augmented version of the original story.) This story contains descriptions of unprotected sexual activity. Such behavior in real life exposes the participants to the utmost risk. This fictional account, meant purely as fantasy, is in no way intended to promote it. As Travis walked along a busy street that morning...

The Boy in Makeup

by DavidPatrick on Sep 14, 2017
Gay Male

Chapter One Like the men who made suicide is in my genes. The temptation was too great for my great-grandfather, my grandfather, and my father, having lured all three to the other side. Theories abound as to why. No one knows for sure. I think it's because there was too much dissonance between who they really were and who they pretended to be. We all prete...

Sporting Chance

by perihelion on Aug 30, 2017
Gay Male

Two hours after the school board hired me, I sat with my new principal in his office. "Jeremy, I'm glad you decided to call me. I just wish you'd done it sooner so we could talk." "It's like I said, no point in bothering you until I completed the courses I needed to teach in Georgia. I still don't understand why I had to take those extra classes if I didn'...

A Chance Encounter

by jaypbee on Sep 14, 2017
Gay Male

DISCLAIMER All characters contained within are entirely fictional; any similarity to any real or fictional person living or deceased is totally unintentional. Do not read this story if you do not enjoy reading about consensual sexual activities of an exhibitionist nature. Otherwise read on...... CHAPTER 1 It's funny how life can throw a spanner in the wo...

Best Friends Become Lovers Ch. 04

by UnderMyKilt on Nov 29, 2017
Gay Male

For those who haven't read them or have forgotten, you may have to read the previous stories to know how we got to this point. I hadn't intended for this to be series, but it turned out that way and this will be the last story under this series title. As we left off at the end of Chapter 3, Wayne and I had just fallen asleep after making love at a remote ca...

Rest Stop Management Pt. 03

by rimaday on Dec 24, 2018
Gay Male

I awoke around 4:45 on my belly, my red panties a little twisted and crusted with dried cum. I could feel Big Daddy's deposit oozing down my taint and hardening in the panties. I could not believe, this was not some kind of twisted dream but my stretched leaking asshole took away all doubt. Twelve hours ago, I was kissing my beautiful wife and leaving for an...

Max's Chance

by robcub32 on Sep 26, 2017
Gay Male

(Note: This story features characters from "A Clean Start". You don't have to read that story first, but I recommended it.) "Hi, Max!" the familiar voice called out. As I walked out of the locker room, I looked and saw Pete's smiling face standing next to the weight rack. Pete was my best friend Tank's boyfriend or partner or whatever you want to call it....