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 bit of a gut and a day's growth of beard. Not bad looking.
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."