Free Jailbait by Jack Kilborn

I walked into my neighborhood bar, a fierce winter wind following me inside. It wasn’t my favorite watering hole, but it was within walking distance of my place, and I was so cold my balls were making clinking noises every step I took.
    I stood at the entryway and paused, taking the place in. It was darkish, grimy, still smelling of cigarettes even though Chicago had banned smoking indoors years ago. The after-work crowd had dwindled down to the diehards—those without families to go home to.
    I didn’t have a family of my own to go home to. I wasn’t looking to find one, either. They were expensive, messy, and needy. My presence at the bar was twofold. First, I needed a drink. Second, I hoped to get a little something-something. Nothing made the cold, winter nights easier than a little bit of strange.
    I took a quick survey of the thirty or so patrons in the place, judging and discounting the women with rapid-fire glances.
    With a guy. Too old. Ugly. Fugly. Chicken neck. Nasty birthmark. Fat. Bad teeth. Double chin. Missing an ear—Jesus Christ. With a guy. Fugly and too old. And—
    Hello… who is this vision of loveliness?
    I went in for the closer look. She was blond, perched on a barstool. Her skirt was far too short for the weather, and she had one leg crossed over the other, her foot ending in a red pump sporting a killer stiletto heel. I let my eyes drift upward. Nice rack, struggling to break free of the tight button-up shirt she wore, the first three buttons open. Lipstick that matched the shoes. And…
    Jesus. Pigtails. That’s hot.
    I swallowed, then took the seat next to her.
    “Can I buy you a house?” I asked, leaning over.
    She gave me a look as if she wasn’t impressed.
    Not that I fell for it. Hard to get could be a lot of fun. “Well?”
    She sighed, giving her chest a nice up and down bounce. “Start with a drink. If you don’t fuck that up, I’ll decide if you can stick around.”
    I raised my hand for the bartender. “Can I get a Goose Island and three bottles of tequila for the lady?”
    She peered at me under raised brows. “Rail booze?”
    “Excuse me?”
    “I’ll give you points for quantity. You’re lacking in quality.”
    “Sorry. Wasn’t paying attention. I was looking at your boobs. Did you have a drink preference? I’ve found it all comes out looking the same.”
    “I’ll bet.” She spun her stool and gave me her back.
    I stood up, taking the opportunity to check out the top of her head.
    She glanced back. “What the hell are you doing?”
    I sat down again. “Checking out the view I hope to see later. I gotta say, I really dig the pigtails. Besides the naughty schoolgirl vibe, they’re also like handlebars for blowjobs.”
    “You’re charming.” She rolled her big brown eyes. “The way herpes is charming.”
    I winked. “Give me enough time to finish one drink, and if you aren’t completely charmed I’ll take off and never bother you again. Fair?”
    Her lips pressed into a non-committal line. “Pour the tequila. I always was a sucker for a challenge.”
    The Goose Island arrived, and I bugged the bartender for two chilled shots of 1800. Then I offered her my hand. “I’m Harry. Harry McGlade. Have we known each other long enough for me to get your name?”
    “No. You can just call me babe, because I know you will anyway.” She gave me a quick, perfunctory handshake.
    “Fair enough, babe. I gotta say, though, that it’s past seven pm, so if you were looking to hook up with some yuppie, they’ve all gone home. And dressed like jailbait, I’m guessing you did come to hook up. A lady doesn’t look this sexy if she’s just going out to get drunk. So I may be your last chance at a good evening. And while I like a challenge, I’m not into bitter and disinterested. So what can I do to push your defrost button for the next three minutes?”
    She looked past me, focusing on something or someone near the door. When she glanced back, the cynicism was