The Anonymous Sex-Confession Blog

Rooftop Thug

I’m a baby-faced thirty-something blond white guy who lived in a rather rough neighborhood in Philly for a while. One morning when I was walking my dog really early (5:30am or so) before work, this young tough-looking black kid started walking right towards me in the dusty morning light and before he was close enough for me to see that he was actually gorgeous, he was asking me about my dog. I was pretty nervous, not just because I was alone in my back parking lot with this stranger, but because I only had on a pair of sweatpants and any amount of hard-on would be immediately obvious. He walked right up to me, close enough that I could smell his smokey breath, and asked me if I was gay. Shocked, I started to stumble on my answer, which he took as permission to grab my crotch.

In a complete haze, with my heart beating like crazy, I quickly brought my dog up to my apartment, swished with mouthwash, grabbed a condom and went back out to my rough trade in the hallway. We never used the condom, but stood on my building’s rooftop jacking each other off furiously with the sun coming up. As clumsy and surreal as it was, this one time experience is the hotest thing that’s ever happened to me.