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Craigslist hookups

One reader cops to her first time having sex with a stranger.

Female, 35, Uptown
After a decade of serial monogamy, I knew the last thing I wanted was another serious relationship. At the same time…a girl has needs, you know? The bar/club scene has never been my thing, but Craigslist had previously found me Cubs tickets and a quality apartment, so why not some much-needed sexy time?

My ad on “casual encounters” covered basics like my age, height, dress size and hair/eye color, followed by an outline of what I wanted: to meet a clean-cut, respectful, older man for drinks and, assuming we clicked, an evening at his place. Twenty minutes later, my in-box was flooded with messages from every Tom, Dick and Hairy in Chicagoland. The senders ranged in age from 18 to 70. Most demanded photos. Several inquired about my grooming practices in places I feel uncomfortable discussing with my gyno. Between the obviously mass-produced form responses and the crazies who asked me to scold them for wearing tutus, there were a handful of seemingly average guys who gave good e-mail. I exchanged responses with several contenders until I’d whittled the list and settled on a nice-looking, 42-year-old guy named Steve.

Steve met me the next night at a low-key bar, and we chatted and flirted until I felt convinced he wasn’t a serial killer. We split for his place and had another beer on his ratty, dorm-chic couch before we started making out. That’s when I learned Steve had a habit of whimpering when he kissed a girl. Whimpering wasn’t threatening, just…weird. Eventually we hit the bedroom, and I’ll spare the details except to say that Steve was loud. As in, “oh, Christ, where are my earplugs?” loud. It’s been a few years, but the thing I remember most about the experience isn’t how good the sex was or even what he looked like, but rather how difficult it was not to laugh at his bellowing—especially at the end, when he congratulated himself.

My final “dude, what the hell?” moment came in the bathroom, when I noticed the McDonald’s cup holding his toothbrush…right before I noticed there was no toilet paper. Steve asked if we could hang out again, but I claimed work conflicts before scampering out the door. Technically speaking, I suppose you could say my evening with Steve the Screamer was a success because I got all the sex I’d been craving. But in my mind, the real accomplishment was renewing my appreciation for my vibrator: all business, no screaming.

FIRST TIMER’S TIPS * Beyond safeguarding against pregnancy and STDs (everyone on CL claims to be disease-free—wrap it anyway), keep in mind this is risky behavior, as in, you could end up in a Dumpster. If you do proceed, make sure a friend knows where you are and expects to hear from you at a certain time. My friends and I reasoned that if the cute, Michael C. Hall–looking guy suddenly took a turn for the Dexter, he could easily text “all’s well” from my phone while preparing the Saran Wrap and knives. So when one of us has a hookup, we include a ridiculous, inside-joke code word in our update communications. * Don’t make it a sleepover. Nothing but awkwardness will come of it. * If the ad says just sex, don’t expect more—no matter how good the banter. This ain’t eHarmony. * Be honest with yourself: Fun and flingy sex isn’t going to make you feel less lonely or solve any problem other than an orgasm deficiency. And even then…sometimes not so much.

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