The runner up: Artie Lange, losing his virginity in his father’s handicap van. We’re sparing you the dirty details, you’ll have to buy the book for those. Too Fat To Fish (Spiegel & Grau, 2008)
“You like me, right?” she said.
“Yeah!” I nearly shouted, I was so excited. “How much would you charge me to have, you know, full sex?”
“This is $50,” she said. “You want sex and blowjob, is $75.”
“Fine,” I said. “I brought cash with me. I have it right here!”
I didn’t care for one minute that $75 was easily half of my net worth in life - probably more. And the virginity thing was still a concern, but her beauty transcended my mission. I just had to fuck this girl, she was that hot. The only conceivable problem could be whether or not she’d do it in the handicap van.