This is a story that happened a few years ago. I was [26] then and my friend's Dad was about [50].
It was the middle of summer and I was helping a family friend with a a construction project in his private backyard. We'll call him Jack. I'll call myself Ryan.
I had known Jack since I was young. I had grown up around him and he was a very nice man, always respectable and kind.
He was handsome. Dark olive Italian skin, hairy and barrel chested. Thick forearms and hands. A full head of hair.
Now, I'm mostly straight, but ever since I first gave into my curiosities in college, I've craved a man's cock every now and again. At the point in my life when this story takes place I was experienced enough with men, but I had never thought of Jack in a sexual way at all, so what happened one day while I was helping him with a building project was completely unexpected.
It was a hot day and we had been drinking beer while we were working. Jack and I had already finished off a 12 pack so we were feelings nice and loose in the hot summer sun, both sweating pretty heavily.
I popped my shirt off without thinking about it. Two men casually working outside, nothing strange about that.
"Pretty fit still, Ryan", he said looking over at me.
"Thanks Jack. Trying to keep athletic in my old age". He laughed.
A few minutes later he said, "mind if I pop my shirt off too? It is pretty hot now that I think about it."
"Go for it", I said without really looking at him. Then when I finally did look at him I noticed he was pretty fit for an older guy. So, to be polite, I returned the compliment.
"You're pretty fit too Jack, for a young guy like yourself." He laughed casually as he put both his hands on his hips and made eye contact with me. I held his eye contact.
It should have been awkward eye contact, but it wasn't. We held the gaze, smirking at each other, for what seemed like a minute.
"I'm gonna go use the bathroom", I said as I walked toward the door. "Alright", he said.
I headed for the bathroom thinking about what the hell just happened. It was weird, but also wasn't. This man, who I've known my entire life, definitely just made sexual eye contact with me, but I couldn't really believe it. Jack was divorced, had kids, he was a straight guy. A masculine Italian man of faith. But he had just ogled my naked torso and commented on its fitness, that was no idle gesture.
Then suddenly the door to the bathroom opens, while I'm mid-stream.
"Ah sorry!" Jack said quickly, but not after certainly staring at my package.
"Thought you were in the other bathroom!"
He did that on purpose, I thought. There's no way he thought I wasn't in here.
"It's ok. I'm just about finished." I flush and leave.
He goes in, we slightly brush shoulders even thought there was plenty of room for us to walk around each other.
As Jack goes in, he leaved the door slightly cracked open, not quite closed. My heart started to pound. Was this really happening? Was this an invitation? I decided to find out.
As Jack's steady stream began to finish I quietly pushed the door open. His hairy broad shouldered back was to me. He was shaking his cock out.
"Jack", I said. He picked his head up and stood a moment, I guess gathering himself. And he turned his body to me, cock out.
It was huge.
A giant uncut Italian cock thick and long flopping out of his pants.
We stare at each other for a moment, taking it all in, all the history behind us. The taboo of this older man and me. His cock started to get hard, as did mine.
He walked toward me and pinned me against the bathroom wall, looking down at me.
"I always knew you'd be a good boy". Then Jack took my face in his hands and kissed me. I normally don't like kissing men, but I liked it when Jack did it.
"Now I want you to be a good boy for me Ryan".
"Yes Sir", I said, transforming into the submissive person I am in the bedroom with men.
And with that I dropped to my knees, staring at his cock straight on. He grabbed his cock and flopped it over my face. I began to run my tongue up and down the shaft. He took his balls and put them both in my mouth as I started stroking his cock. Then I took his entire cock in my mouth, spitting on it and lubing it up for my throat which he penetrated the very next moment. Grabbing the back of my head and guiding me down his entire shaft. I gagged and grabbed onto his thick thighs and ass, squeezing for help. He made me gag a moment more before letting me breathe.
"Spit on my cock Ryan". I did so and the spit dripped off his cock and onto my body. He leaned over and stuck his tongue in my mouth to get some of my spit.
"Tongue out." And he spit my spit back in my mouth. Then he picked me up and carried me to the next room where there was a couch.
"Get naked for me baby, Daddy wants to taste you."
So I stripped naked for him as he stood there stroking.
"Where do you want me Daddy?" I couldn't believe I was calling him Daddy and throating his cock, this man I've known my entire life. My family friend. I loved the idea of the secret of it.
He didn't even answer my question. He just picked me up again and put me on my back. He pushed my legs back, exposing my tight pink hole. I heard him groan at the sight. Then he buried his tongue deep in my asshole. I knew he was preparing me for his cock. I squirmed and moaned at his tongue lashing. Then he stopped. He got up and got some lube and squirted some on his cock and my asshole.
He started to massage my hole with the tip of his cock which almost made me cum in and of itself.
"I can't believe you're going to take my cock. After all these years. I've wanted you for quite some time Ryan."
"Thank you Sir. I want your cock. Now spread me open."
And with that he threw my legs over his shoulders, took my throat in his strong thick hands and gently thrusted his cock inside me. Once his thick head finally penetrated all the way he was in to his balls. Thrusting slowly. I liked the way he choked me and made me feel like a little bitch.
He never took his eyes off me except to admire the gaping hole he made in me with his cock, to which he'd groan at.
"Daddy's gonna cum inside you Ryan, I'm close".
"Cum inside me Jack. MY hole is yours daddy, cum in fucking side me", I moaned as his huge dick massaged my prostate and I could feel myself swelling with cum.
I could feel his cock swelling and his body tensing. He leaned over me more, his big heavy body weighing me down and pinning me to the couch.
"Fuck I'm gonna...cum!" He grunted as he began his spastic thrusts and groaned like a beast. I began to cum and was squirting cream all over my chest and even hitting my own face from the power of the explosion.
Jack continued cumming as he gripped my throat harder and stared me in the eyes. After a minute or two he finished thrusting and took his dripping thick cock out. I could feel the gallow of hot cum begin leaking from my gaping asshole which was gasping for more.
Jack helped me up and we took a shower together. We eventually finished the building job, though a lot slower now, because we had found something else to pass the time that summer.