Sleeping Around Craigslist

AlterNet is resurfacing some of the best and most popular articles published in 2008. In this piece, published this July, Anna Reed and Lily Penza go undercover to explore what sex life is like on Craigslist.

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 11 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 10 counties and four states and involved roughly 45,000 e-mailed words, 27 phone calls, 36 face-to-face initial dates and 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 10 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 40 pounds and decided she would make up for lost time.

Anna Reed is a 50-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 40s.

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 menage a 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.