Italian Guy Pops My Cherry

I had been fucking myself with a 7-inch dildo for awhile, but hadn’t taken a real cock in my ass yet. I didn’t really expect this to be the day, but I try to be open to anything and I had been fantasizing about it for years.


He was just a random craigslist hookup; married. Lived over by Washington Park. His wife was out of town on business and he was looking for a little strange ass and cock. I had just gotten into D-town for the week and had the afternoon free. He wanted to meet in the alley, come in through his back door. So to speak.

I had been fucking myself with a 7-inch dildo for awhile, but hadn’t taken a real cock in my ass yet. I didn’t really expect this to be the day, but I try to be open to anything and I had been fantasizing about it for years, and had let my girlfriend fuck me with a strap-on a couple of times.

He was 40-something, Latino or Italian, had a nice body and a fairly groomed beard. Very attractive.

We made out in the recently remodeled kitchen first. Tongue. My hands up under his shirt, all over his body. He had me pushed up against the counter. I love it when a guy takes control like that. Pushes me up against the wall or down onto the bed. When I’m with a chick, I like to be in control, but with a dude: totally the opposite.

He took a step back and led me to the bedroom. I took his shirt off and worked on his nips for a while, licking, biting. I mouthed my way down his slightly hairy stomach while I got his belt and pants undone so I could get at the hard cock I could feel straining at his jeans and black boxer briefs.

It was about 7-1/2 inches long, a couple of inches around, and uncut. I pushed him back onto his bed. He leaned back while I got on my knees in front of him and stroked his foreskin back with my right hand, swirled my tongue over the head, then took it in my lips and slid my mouth up and down the shaft. I stroked his stomach and hip with my left hand.

“Mmmm. You’re a good little cocksucker, aren’t you? You like to suck that cock.”

I looked up at him, twisted my hand around the base of his dick a little, slicked up with my saliva, and nodded at him with the blowjob eyes, keeping his hard cock in my lips. I have a mouth, BTW, that was just made for sucking cocks: full lips, agile tongue.

I lifted my head from his dick, stuck my tongue out, and slapped the bottom of his head against my tongue a few times. I love the sound of a hard cock slapping against my tongue. This is a little trick I learned from a girlfriend, who gives incredible head. He moaned again and thrust his hips.

After a few minutes of this I stood up so he could get my shirt and pants off, and then we made out some more. His hands were up and down my back, grabbing and smacking my pert ass. I helped him step out of his jeans and pushed him back onto the bed, sucking his cock some more to keep it nice and hard and wet. I took out a bottle of oil, slicked his cock up with it, and spread it up and down my ass crack.

I climbed on top of him and put the head of his slick, wet, hard cock against my rosebud and rested there until I worked the head inside my tight hole. Then I slid the rest of the way down the shaft and back up again, until just the head was still inside. Then up and down a few more times, getting used to the new sensations.

I was getting fucked. Bottoming, Getting my fudge packed. It felt just… awesome.

“Oh fuck,” I moaned, my eyes half closed and my head thrown back. “Fuuuck.”

“You like that hard cock, don’t you?”

“Fuck yeah. Fuuuuuuuuck.”

It felt warmer than the silicone dildo I had been using on myself. And I didn’t have total control over it. So hot. I rose up until just the tip was still inside my tight, wet hole. He started pumping up and down, sliding in and out, long slow strokes at first, then faster and harder.

“Ngnnn. Ahhhh. Fuuuuuuuck.” I put all my weight down on his hips and ground in circles, leaning forward so his dick could hit my p-spot, my hands on his chest. I’m sure my eyes were rolling back in my head at this point.

He popped out and now that I was loosened up a little, I turned around and showed him my juicy ass as I settled back down on him reverse cowboy style, and rode. This is my favorite position, incidentally, either from the receiving or giving end of things and with both chicks and guys. I love to watch a nice ass bouncing up and down on my cock, and I love the different angle it gives me when I’m riding a cock or a dildo.

After a few minutes of this my legs started to get tired, so I popped him out again and rolled over onto my back. He took my hard 6 1/2 inch cock in his mouth and bobbed up and down on it a few times, then lay the full length of his body down on top of mine and put his tongue in my mouth.

After a passionate, lusty kiss, his rough beard against my clean-shaven chin, he pulled away, threw my legs up over his shoulders, grabbed his dick and guided it to my pulsing browneye. Then he started again with the long, slow, steady strokes.

My eyes were closed, my head rolled to one side, the full weight of his sweat-slicked body on me. He let my legs go, held my wrists down onto the mattress over my head. I pushed and bucked my hips up into his to get the full length of his shaft inside me, and wrapped my legs around the small of his back.

After a few minutes, he pulled out and flipped me over onto my hands and knees, grabbed my hips and pulled me back onto his cock again. I arched my back, giving him my ass. He pounded me faster and harder, his big, rough hands sliding up and down my torso, and then pulled out with a pop and shot his load all over the small of my back.

He fucked me again a few weeks later in my ex-wife’s house (my next post, perhaps). He’s gonna fuck me again this weekend. I can’t wait.

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