Gay Sissy Stories

744 results
Orientation
Length
Source
Infinite Scroll

My Handyman

by robcub32 on Sep 14, 2017
Gay Male

I walked into the restaurant and looked around for my friends. I saw Walt waving at me and I headed over to their table and took a seat. My friends Walt, Chip and Byrne were already seated at the table waiting on me to arrive. Walt is my best friend. We met the first day of high school. At that time, we were both closeted gay boys and we somehow gravitated...

Bobby and the Cop

by robcub32 on Sep 25, 2017
Gay Male

Time seems to go by so quickly. It was almost a year that I moved out of my mom and step-dad's house, but it seemed like just yesterday. After graduating from college, I returned home to the Detroit suburbs. I got a job fairly quickly as a computer tech. The company I worked for sold PCs and custom software to small and medium-sized businesses. I did diagno...

When Irish Eyes Are Smiling Ch. 05

by TomNJus on Sep 25, 2017
Gay Male

*Joel* "You just want to play with my suspenders," he mockingly accused. "Not just, Muffinman," I parried, grabbing his suspenders and pulling him up to me. Tipping my head to the side, I let my lips brush his as I whispered, "My plans also include riding you into the sunset." My hands slid up and down his suspenders; I felt his nipples stand up through hi...

Just a Number?

by NRMathis on May 9, 2018
Gay Male

Couples with large age gaps have some sort of assumptions that are automatic whenever people look at them or think about them. If it's a young man and an older woman, she's a cougar. If its an older man with a younger woman, she's a gold digger and he's her sugar daddy. If it's two gay men people assume a sissy-boy/daddy relationship. With lesbians, I have n...

Three Strikes Ch. 10

by Mrsgnomie on Nov 20, 2018
Gay Male

It was Sunday morning and I decided to text Drew, Aaron, and Kurt. [Shane]: Hey, guys. Since we haven't gotten together for a while and I miss you, how about doing breakfast or lunch? At least, that's what I told them. They didn't need to know the truth—Donovan was working and I needed to distract myself. It wasn't until I stepped out of the shower tha...

Coming Home: Davis Brothers Ch. 04

by robcub32 on Sep 25, 2017
Gay Male

"Fuck!" Brandon slumped back with a groan. "God damn, you know how to suck cock." Lonnie raised his head from Brandon's lap and made a show of swallowing the remainder of Brandon's load. "I love sucking you." "That fucking mouth of yours is gonna give me a fucking heart attack." Lonnie snickered, then planted a kiss on the end of Brandon's cock. He let i...

Lariats and Lacrosse Sticks Ch. 04

by reddirtwriter on Sep 25, 2017
Gay Male

There are scenes of unprotected sex depicted in his story. In all cases it was between the two main characters, who are in a committed, monogamous relationship and were tested. If you aren't in the same kind of relationship, then you should always protect yourself and wear a condom. Randy double-checked the supplies they had packed. They were going to be...

How to Come Out to Your Parents

by kicky1000 on Sep 14, 2017
Gay Male

How was I ever going to tell my parents that I was gay? This was a confrontation that I had been dreading for a long time, but how long could I put it off? If I didn't tell them, they were going to find out anyway for sure. I was a complete slut. I mean, really indiscreet. One time I got the mailman up to my bedroom, and he was just in the middle of fucking...

His Loving Beauty Ch. 03

by AaronCromwell on Sep 16, 2017
Gay Male

NOTE: I hope this chapter isn't too kinky for those of you who enjoyed the first two chapters, but if it is, I encourage you to read it anyway even if only for the plot resolution. ----- What happened after that Super Bowl weekend taught me a lot. The most amazing thing to me was not just that Damon committed to loving me; it was how smoothly and comfortab...

Hot Tub Trio Ch. 09

by Turbidus on Sep 17, 2017
Gay Male

I have posted the majority of this tale in the "Group Sex category. I don't wish to cause confusion but this chapter is almost entirely MM sex. For that reason I have posted in under "Gay Male" although there is just a touch of MMFF group sex at the end. Once again my thanks to LarryInSeattle for his help editing. As always any errors that remain are mine a...