Sleeping Around Craigslist 

Two middle-aged women discover that casual sex is anything but casual.

It takes a woman about a thousand words and a condom to get laid on Craigslist. But for a woman to be laid properly — by a passionate lover who knows what he's doing — well, that's a whole different ball game.

We are both middle-aged women who have spent the past eleven months sleeping around Craigslist. At an age when most women were sending their firstborns off to college, we found ourselves — through chance and circumstance — single, tumescent, and ripe for adventures. Those adventures have spanned ten counties and four states, and involved roughly 45,000 e-mailed words, 27 phone calls, 36 face-to-face initial dates, 13 actual lovers, and re-aggravated our carpal tunnel syndrome from all the typing.

Years before embarking on Craigslist, both of us had experienced sexual abandonment. We were both hungry for intimacy and physical touch after years of wandering in the desert. Our lives were on similar trajectories.

Lily Penza, 46, had been overweight since her teens and suffered from dangerously low self-esteem. At age 28, she moved in with the first man who looked her way. It was a virtually sexless union for ten years before a therapist helped her come to her senses and move on. Lily never married and spent most of her life caring for an ill parent who died recently. So she lost forty pounds and decided she would make up for lost time.

Anna Reed is a fifty-year-old who, as a young woman, had been raped and pressured into sex during the so-called sexual revolution. She had read books on women's sexuality — Barbach, Tisdale, Jong, Hite, and Nin — but each held only a small piece of the puzzle. Not one of these authors could tell her as much about sexuality as her own inner life did. Emerging from a stale and sexless marriage, she would do things her way this time around.

Lily turned to the free Craigslist personals because didn't want to spend any money getting laid. She started answering ads last July. She was open to every person and every experience — even Republicans, as long as they could kiss. Lily told her close friends about how thoroughly she would be sleeping around, joking "I want my vagina to have call-waiting." Now she is enjoying the adolescence she never had; dating like an oversexed high school student but armed with the wisdom and savvy of a woman in her forties.

Anna decided to try Craigslist because she found other online dating sites too silly. Now, despite her wrinkles and middle-age spread, she "dates" a multitude of guys. But they aren't really dates. "We don't go places together, they sometimes buy lunch but just as often they don't. I'm sleeping with them. Actually, that's a euphemism; we have sex." With a lover whose bad back has him on the injured reserve list, Anna knows what to do: click on "Casual Encounters" and start the e-mail banter that almost always leads to a meeting. "I don't have a boyfriend," she says, "I have a team roster."

Lily and Anna are not our real names, but then you probably knew that was coming. Virtually everyone on Craigslist lies about something: their name, their age, their weight, their marital status, maybe even their penis or bra size. For the purposes of this story, we have changed everyone's names to protect their privacy.

The two of us met when Anna answered an ad that Lily's then-boyfriend, Scott, posted on Craigslist. Lily and Scott were seeking a third partner to join a ménage à trois. Before anybody actually met face-to-face, Lily dumped Scott and canceled the threesome, but she became e-mail pals with her would-have-been sex partner, Anna.

Once we met, we realized we had a lot in common, and began sharing our respective experiences. Our adventures have included the hot, the not-so-hot, and some potential hook-ups that never even got off the ground. There were memorable ones, like Lily's first date, which ended at 3:30 a.m. at the Power Exchange sex club. Or the ex-con who went down on Anna for an hour straight.

There were forgettable ones too, like the alcoholic art dealer, or the guy who excused himself in the middle of sex to smoke a cigarette. And there have been multiple-partner dates, which involved average-looking East Bay residents who swing, tie up, dominate, submit, and spank.

What kind of sex did we find? Some of the lovemaking was wonderful, a lot of it was initially awkward but got better as time went on, and some of it was downright disastrous. Up-ending the notion of "Casual Encounters" — as Craigslist dubs its "Just Looking to Get Laid Tonight" category — we both discovered that casual sex is anything but.

Perhaps because we are highly verbal, our initial Craigslist encounters involved a ream of e-mail. Sometimes we just coordinated the logistics of the hook-up, but equally often, we wrote and received profoundly intimate and revealing letters — an epistolary of erotic stories.

Then there is the issue of sexual chemistry, which is arbitrary, inexplicable, and largely unpredictable. Terrific e-mail connections don't guarantee a sizzling face-to-face meeting. And not everyone keeps their word. More than once, last-minute cancellations left us calling one another for support, or just drunk, horny, and alone with a DSL connection.

Finally, there's the zany sitcom a woman's life becomes when she's juggling multiple lovers: scheduling dates; trying to keep personal data straight on each man; finding enough time after work to shave her legs, dye her hair, exfoliate her skin, apply mascara, and MapQuest the planned meeting spot.

But when it works — and it has — there is the sheer joy of exploring sexuality without any strings attached. And sometimes a woman can find a treasured friend with benefits, an outright boyfriend — or the love of her life.

Besides all the rules that sensible people follow when dating online, like "meet in a public place," "let someone know where you are," and "condoms are nonnegotiable," we developed our own special list for middle-aged chicks who date on Craigslist:

1) A lot of men want to screw Sarah Silverman. (Three lovers told Lily the potty-mouthed comedian was their "fantasy fuck.")

2) With ads for people over forty, add at least five years and ten pounds to the photo. That way, when the older and heavier date shows up, you won't be as disappointed. This rule is as applicable to men as it is to women.

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