My Second Try

The first cock inside of my hole was a dull, painful stab. I wanted to reciprocate what my best friend had just done for me - he allowed me to use his ass to lose my virginity. He knew to relax to let me in, and took my tentative strokes with verbal reassurances that he was ok, I could keep going. And I did, until I let loose a torrent of jizz into the first condom I'd ever worn. I'd promised I'd do the same for him, and got down on all fours, ready to be fucked to completion (we were pretty horny teens). But one deep, invasive entry later and I was a hard no. No pun intended. I sucked him to completion instead, unable to use my hole - a hole I'd enjoyed exploring with fingers and objects, so what was my deal? Why couldn't I take a cock?

It was an incredible first experience, and I imprinted on the idea that male to male sex could be a world of pleasure, but we lost touch with time and distance as we grew up. I dated women exclusively, got married, divorced, and life rolled on. I lived straight; I was straight. Whole decades passed without the opportunity to have another man in my bedroom. I did fantasize about another male lover, mostly through porn - one video here and there and before long my porn-watching was about 90% gay/10% straight. I loved seeing a man make love to another man. I got gutsy enough to buy a 7-inch purple vibrator that I could take up my hole to the hilt, and would fuck myself with it while I jerked off.

And so it went for a time. Me thinking about cock and the carnal lust brought out in me when a man loves the pleasure he can give and receive with his own beautiful asshole. When an out of state work trip presented itself, I realized I could take advantage of a hook up site and I'd have a two month runway to find "Mr. Right" - a top who would be perfectly ok with me saying no if I couldn't fit his dick inside of my body. I landed on a soft-bodied latino college boy half my age who identified as vers-top. We had good conversation and exchanged a lot of pics, leading up to our planned hotel room romp. His cock was uncut, unlike mine, but about the same size and girth. I wanted him inside of me, but would it happen?

We greeted at my hotel with a deep, wet kiss and he could feel my cock spring to attention as we locked lips. He reached his hand down and undid my pants and fondled my leaking shaft as I kissed along his neck. The anticipation was killing me.

To make myself fully comfortable, we took our makeout session to the shower. He felt right in my arms. The weighty heft of his ass cheeks in my hands, allowing me access to the incredible red hot center of his puckered, willing slit within. His mouth lovingly slurping my own slick cock, which somehow felt engorged in a way it hadn't been with a woman in years. My six inches felt heavy and enormous for the first time in a long time. I wanted to fuck this man. And, more importantly, I needed him to fuck me.

I laid down on the bed on my belly, and for the first time ever, my hole was eaten out. Hungry laps from this new gay friend brought me, a straight man, to the point of begging. "Fuck me, please." He would stop tonguing my rim to ask again, like a tease. "You want that? You want my cock?" YES. Please. Bare.

He raised my hips up & greased me up with cold lube and a finger and then I felt it. A bigger push into my backside, from the dark pink head of his rigid cock. It worked its way in slowly. I was tight but accepting. Lots of "you ok?" and me replying "yeah" because I was more than ok - I was in heaven. Before I knew it he was in my own virginal male pussy, and I felt light-headed and euphoric off his tempered strokes. I did it. I could take cock. He used my hole to get himself to the edge, then laid on his back, legs over my shoulders, and I fucked his sweet young ass until he milked the boiling cum out of me & onto his stomach.