Everyone in this story is 18+.
This is the story about the time I got fucked by my buddy’s dad. I don't remember all the details or what was said, but you'll get the gist. We’ll call the dad James, and we’ll call my friend Dan. It was summer and I was hanging at Dan’s pool as we did almost every day. We had just graduated high school, so we were kind of soaking it in before we went off to separate colleges.
Dan and I had been friends for a long time, so we didn’t have a problem swimming in our boxers if we had to, and it wasn’t entirely uncommon for us to just skinny dip. Dan had a decent dick and body, but I didn’t really look at him that way, so it was never weird. One day, though, James came out while we were in the pool one late afternoon. He was wearing some board shorts and no shirt. He was in his 50s, bit of salt-and-pepper going on, and a dad bod. Hairy, too.
Before this, I’d never really looked at men in general. Hadn’t had much luck with girls in school. Not like Dan, who lost his virginity early on. I was just more on the awkward side. But seeing his dad’s hairy belly…I couldn’t quit sneaking glances.
He sat in a lounger and talked while Dan and I splashed around in the pool until eventually Dan said he was getting out and was gonna take a shower. I wasn’t quite ready to get out yet since it was still hot so I told him I’d get out when he was done. After that, it was just James and I.
James started asking me the same questions I’d been answering for the last six months: where I was going to college, what am I thinking about majoring in, etc. We shot the shit for a little while, and then he started asking me about relationships.
“You have any girlfriends?” he asked me. I told him no. “You ever had a girlfriend?” he asked. Again, I told him no. He whistled low and asked me if I’d ever “fooled around.” I noticed that he sneakily adjusted himself as he asked. I admitted I made it to second base once, but other than that, no.
“You ever fooled around with a guy?” I know I blushed hard, but I quickly denied it. And that was the truth. I hadn’t.
“Damn. You can’t go to college with no experience, man. You’re gonna wanna fuck everything that walks!” He let out a laugh, and I nervously chuckled. Then, suddenly, he got serious. He asked if he could join me, and I said yes. It was his house.
But instead of just jumping in with his board shorts on, he undid the drawstring and let them drop to his ankles. I quickly looked away, trying to act like the whole situation wasn’t extremely weird. But when he got in, he came to stand right behind me.
“What’s the matter?” he asked. “I’ve seen you skinny dip with Dan before. Why don’t you take these off?” He tugged at the waistband of the trunks I had on, then ran his hand up my side and over my chest.
I don’t know why I didn’t stop him. I also don’t know why him touching me gave me an immediate boner. Although it didn’t really take much.
He shifted and stood a little closer until I could feel his dick against my ass, then he loosened my trunks and began pulling them down. Again, I didn’t say anything. I couldn’t think, just feel. And what I felt was horny.
I picked up my feet when he got the trunks down around my ankles and watched them sail over my shoulder as he tossed them onto the patio. Suddenly I was naked in the pool. With my best friend’s dad. And his cock was nestled in between my ass cheeks.
Next thing I knew, he had one hand wrapped around my cock and he started jerking me off under the water. He asked me if I liked it, and I just nodded my head, to afraid to say any words. His other hand was caressing my ass cheek until eventually he ran it up the middle, over my hole. I shivered.
He stopped jerking me off at this point and gently turned me around until I was facing him. He grabbed my wrist and led my hand to his cock, which was starting to chub. I grasped it and started stroking. It was a little clumsy; I’d never touched another cock besides my own.
“That’s it,” he said. “That’s a good boy.”
Boy did that light a fire in me. I started jerking him off in earnest while he ran his hand over my abs and chest.
“Why don’t you come here a minute?” I remember him saying. He got out of the pool and walked into the pool shed, and I followed him. He told me we had to be quick because Dan would probably be done showering soon. Then he told me to get on my knees.
Before I knew what was going on, his cock was in my mouth. He didn’t give me much time to get used to it, and pretty soon he was basically fucking my mouth, moaning my name and telling me what a good boy I was being. Telling me he’d get me ready for college. And I fucking loved it.
Then he pulled out of my mouth and told me to turn around. He pushed me over until I was bent over, hanging onto a shelving unit. My whole body was shivering. I wasn’t quite sure what he was going to do until he spread apart my cheeks and I felt his stubbly face in my crack. He lapped at my hole with his tongue. I’d never felt anything like it before.
He circled it a few times with his tongue, and then he put his finger in me. I gritted my teeth against the sudden pain, but he told me I was taking it like a good boy. He inserted more slowly until suddenly he touched a spot inside of me that made me feel like every nerve in my body was just electrified. I later learned he’d hit my prostate. I didn’t know that then, but I knew whatever it was was fucking incredible.
James finger-fucked me for only another minute, then he pulled out. I felt kinda empty after. But not for long. He stood up and rubbed his cockhead against my hole. I think he felt me tense up because he whispered in my ear, “Are you gonna take daddy’s cock like a good boy?” After a second’s hesitation, I nodded.
He pushed it in, which caused a searing pain. Even when he hit my prostate, the pain didn’t go away. But it ebbed after a minute. Which was good because James didn’t waste any time. He grabbed my hips and thrust into me over and over, pushing on my shoulders so that I’d arch my back more.
“Fuck, Austin, who knew you’d grow up to be daddy’s little slut?” he said as he pounded me. I remember my head was knocking against the shelves in front of me, but James was fucking me so good I didn’t care.
He started fucking me faster. “You want daddy’s load?” he asked. I’ll be honest, I didn’t know if I did or not. I’d never done this before, so after a second I just nodded. “Tell me you want daddy’s load,” he commanded me, making my face flush.
“I want daddy’s load,” I muttered, embarrassed but so fucking turned on. He reached around and started jerking me off again, but just his touch was enough to get me close.
“You wanna come with daddy?” he asked.
“I wanna come with daddy,” I answered, knowing it’s what he wanted.
“Good boy.”
Another minute went by, the shed filled with the sounds of our bodies slapping together and the occasional moan. With James jerking me off, I knew I was going to come any second. I wasn’t the only one.
“Fuck, I’m gonna come,” James grunted. Suddenly he thrust his entire cock inside me, his body tense behind me, and then I felt a warmth in my ass that I assumed was his cum. His body spasmed against me, his hand stroking me unevenly. It didn’t matter, though. I didn’t say anything, but I’m sure he felt my ass clench down on his cock as I squirted the biggest load of my life onto his shelves and floor.
When we were done, he slipped out of me. Suddenly I was feeling incredibly awkward, so I made to leave when he put his hand on my shoulder and turned me around. He held his hand up to my mouth, dribbles of my cum running down his fingers.
“Clean it up,” he demanded. At first I didn’t know what he wanted, then he stuck his cum-soaked finger in my mouth and I licked the salty substance clean. He pulled them out and reached around my waist to smack my ass.
“Good boy.”
He made true on his promise that summer. I spent the days with Dan, and I spent the nights getting fucked by his dad. We nearly got caught a few times, but it didn’t stop until I went off to college that fall. And he was right, I got there knowing exactly what I wanted. I wanted to keep getting fucked.
