This story first appeared at Ruthie’s Club, the net’s largest illustrated erotic stories site.
We were in a downstairs martini bar, something with a number for a name, too posh to bother with anything more than a simple address.
Gabriel and I, and the two girls, were sitting in the round booth in the back corner. The girls weren’t with us, but they were with us. Friends. From work. Simple. Right?
Gabriel was complaining, for the umpteenth time, about how he couldn’t meet a girl. He wanted petite, slim, 18 to 25. Sugar baby material.
I told him he was trying to hit the ball out of the park on his first at bat, after his wife of 20 years left him.
The girls agreed.
I said I’d be happy to offer him some advice. I was still in the game, and 10 years younger.
Another round of drinks, the conversation turned and skipped, but would always return to Gabriel and his problems. He’s an only child. You know how it is.
“Look, Gabe, I’ll show you,” I said.
The four of us quickly sketched out the rules, and the waitress agreed to be the judge. A cute cocktail waitress in a tony martini bar? Petite. Slim. 18 to 25. She’d probably heard it all.
Gabriel spoke into her ear. She smiled politely, then turned to me.
I pulled her close, to be heard over the pulse of the jazz band, and said my thing. She nodded. She’d heard it all before. Right?
She smiled at me and shrugged at Gabriel.
The next round of drinks, she slipped a folded cocktail napkin into my hand. I covertly peeled it open, under the level of the table.
Were you serious?
I spotted her across the crowded bar, holding her eyes with my own. I stood and nodded.
She walked toward me, smiling.