Gay Sissy Bet Stories

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Old Jack Ch. 02

by exaucer on Sep 14, 2017
Gay Male

My Working Day: I didn't get to work until after 9.30 and when I entered the office my boss called me over to inform me that I would be going out with Jack for the best part of the day to visit claimants who could not make it in for interviews on account of their physical difficulties. Part of me was delighted and part of me was quite apprehensive. However,...

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...

Was I Raped? Ch. 02

by eviltwin52 on Sep 14, 2017
Gay Male

Note: See "Was I Raped" * 15 minutes after my new Daddy fucked me, I met him back in the bar. The sexual haze having worn off, I planned on setting him straight. "Look you brute," I said, mustering all the indignity I could. "I don't appreciate you bullying me like you did. I have half a mind to call the cops on you." Slap. Daddy had grabbed me by my up...

Sissy Bottom Has a Nite Out

by lostsoul1974 on Sep 14, 2017
Gay Male

My wife had gone out of town on a weekend business trip, so I invited my Fuck-buddy Eric over for some fun. I met Eric a couple years ago when he passed me his business card through a Glory Hole after he had fucked my asshole raw. After I eventually called him, we hit it off and have been friends ever since. Of course, hot raunchy sex can really help cement...

Packing in Tight Places Ch. 02

by drmweaver705 on Jun 8, 2020
Gay Male

All participants are over 18. I entered the code to unlock the door to the storage warehouse with trembling fingers and not a little trepidation. After all, strange as it may seem, the last time I was here, a week ago, I was taken roughly from behind. My anal cherry had been popped by a man whose face I had never seen. I came twice from this man's violation...

Andre Finds Love Pt. 03

by eviltwin52 on Aug 18, 2017
Gay Male

See chapter 2 where my father-in-law fucks me while my wife is away on our honeymoon with her black lover. For those of you who wanted to know what happened to joanie in the final chapter of "It Could Be Worse", the mystery is solved. ***** Part 3: Tomorrow, I thought to myself happily. Lee Anne will be back tomorrow. And her black lover, Leshaun. I...

Glory Hole Favors Ch. 02

by Kent100 on Sep 4, 2017
Gay Male

"Was I going to be as good to him as I was to his buddy?" I thought. "What choice did I have?" The first thing the guy behind me did, was to jamb two stiff fingers up my ass really hard. He twisted them around, jabbing them in and out while exploring the soft smooth walls of my ass with no regard for my comfort or feelings. Secured to the wall by my waist,...

Roommate Turned Me Out

by ralphcollant on Nov 2, 2020
Gay Male

It was a typical Tuesday afternoon after my last class for the day. I walked into my dorm room and found my roommate, Mike, watching porn on his laptop. This was not unusual for either one of us. Some of this junk could be quite entertaining. He nodded and said "Hey Tim" as I walked in and then waved me over so I could see what he was viewing. It was some pr...

Uncle Marty Pt. 02

by Marty Fisher on Dec 23, 2019
Gay Male

This is a spinoff of my Brotherly Love series where my brother's son discovers his uncle's special talents...Part 2 *** I never thought "tomorrow" would arrive, but it did, and I woke up with my small penis tenting my panties thinking about what I was going to do today. Rose was sound asleep next to me as I thought about what had transpired between my brot...

First Time Sissy Sub

by stevn on Aug 31, 2017
Gay Male

My first time was in a booth at an adult video store with an older guy. This is a work of fiction, but if it came true... Please email any comments to the contact on my profile, I would love to hear from you. I'll follow this up with part II. ***** I had placed an ad on Craigslist while on vacation alone in another town. It said: "Submissive sissy bottom...