Uncle Matthew is very handsome, himself. He’s got a perpetual tan, muscular body, and the face of a movie star! Even our cousin, Jack, is quite the looker, too. I’ve always felt a little dopey around him, not really sure what to say or how to respond. And as I’ve gotten older, he’s only shown more and more interest.

I can’t say I don’t like it. I’ve often fantasized about catching him coming out of the shower or returning from the gym. It seemed wrong, but I couldn’t help it. When the leaves started to turn and fall was reapproaching, I knew that I was going to see him again. I got excited, but I also had no idea what our interactions would be like.

It was right after Halloween that I showed up with my friend, Tom. We were just going to say hi, hang out for a bit, and go into town when we saw some pumpkins sitting on the stoop. They weren’t carved or anything, clearly put out for Halloween but never decorated. It felt like a shame to put them out completely blank.

I asked my uncle if we could carve them up and a peculiar sort of smile crossed his face. His smile was always disarming, glowing white and bright. But something about the look in his eye surprised me. He said yes and Tom and I brought in the pumpkins to begin working away.

Tom and I were being dumb and talking about what we were going to carve and such, still wishing it was Halloween. We went to look for a knife and some towels and when we got back to the pumpkins, my uncle was standing there, waiting for us, still with that peculiar smile on his face.

“Boys, come here,” he began. We walked over, waiting for him to simply just remind us not to make a mess or clean up after ourselves. Instead, he mentioned something about a “fall male-bonding harvest ritual.” It sounded like a joke he was setting up, one of my uncle’s attempts at silly humor. But when he explained that it’s done completely naked, I felt my face flush red.

Completely naked? Was he being serious? I watched in disbelief as my uncle began to unbutton his shirt. I could tell Tom was on board immediately. His face lit up and his horny, “say yes” attitude came right out. For me? I was nervous. I’d never seen my uncle naked before. And he’d never seen me naked! I kept waiting for the moment when it was revealed to be a prank, but when uncle Matthew stripped down to his underwear, I knew he wasn’t kidding.

He urged us to do the same. By the time I was just starting to take off my sweater, he was completely naked! There I was, just a foot or two away from my uncle Matthew! Naked!

He was insanely good looking. Better than I had imagined. I had seen him in the pool and on the beach a handful of times growing up, but I didn’t see more than just his muscular chest and arms. Now, I could see every inch of him. I couldn’t breathe or speak. I looked to Tom for a sign of what to do, but he was already all in. He stripped off his clothes and stood naked beside me, ready for whatever my uncle had in store for us.

Apparently while we were running around looking for supplies, uncle Matthew had already carved a hole in one of the pumpkins.

I had seen things online of people fucking pumpkins, but it seemed like a meme or a joke, not something people actually did. But as my uncle explained his “fall ritual,” it became clear that that’s what he wanted us to do.

It felt strange to be talking so frankly with my uncle. He wasn’t a saint, but we’d just never had that kind of conversation. Sex was just not something we ever discussed, though looking like him, it was always on my mind. So to have him positioning me and my friend into position, it was surreal.

Uncle Matthew had me lean over the pumpkin, placing my dick just above the hole. My bare ass was outward facing him, and before I knew it, he had his face right into it. Uncle Matthew! He kissed my ass cheeks, even tonguing my hole. It felt so weird, but I really liked it. He seemed to really love what he was doing, and it felt really good.

I looked at Tom, seeing him stroke his cock watching me get eaten out by my uncle. I felt myself get hard, too. I reached a hand out to touch Tom’s cock, and as I did, my uncle put his hand on mine. He stroked it, teasing me and getting me excited before placing it in the hole he’d carved.

The pumpkin was cool and gooey. I didn’t know if I should like it, but it felt good. Uncle Matthew pushed me into it, guiding me back and forth as I simulated fucking. As I kept going, it got warmer… and felt really nice.

Tom watched and I played with his cock as my uncle continued to kiss and lick my ass. I felt like I was dreaming! This was not at all what I thought this fall would bring!

Just when I thought it couldn’t get more intense, I felt my uncle’s finger going inside my ass. It was slow and smooth, but unexpected. I felt my insides clench around him, seemingly hugging him with my hole. He slid it back and forth gently. It felt so nice, but I couldn’t stop thinking about the fact that this was my uncle!

I didn’t want to admit it to myself, but I wanted more. I looked at Tom and he saw my mouth open and drooling. He stood up and put his cock in my mouth. It tasted great. I’ve never sucked his cock before, and honestly never thought I would. But with everything else going on, somehow sucking my best friend’s cock was the most normal thing happening!

My uncle pulled his finger out of me, leaving my hole with this hungry feeling. I wanted him to put it back. But then I felt his hands resting on my hips and the warm, smooth feeling of loins up against my ass.

I couldn’t breathe. I’m pretty sure my heart stopped, too. I felt myself locked in place in the warm, well-fucked pumpkin as my uncle slowly slid his cock inside me. I couldn’t believe what was happening. But within moments, I felt his thick, hot shaft moving its way deeper into my body, steadily going until I felt his body flat against mine.

I finally let out an exhale. Fuck, it felt so good. Every doubt I had seemed to go away and all I could think about was how hot he was and how much I wanted him to fuck me. As he began to thrust into me, I felt the pumpkin begin to rock back and forth from his movements. My cock continued to work the gourd, all while Tom’s cock rested in my mouth. And in a moment of clarity, all I could think was how much more I was going to need to see my uncle going forward...