Sleeping Around Craigslist 

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

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3) Men have a tendency to overreport the number of sex partners they have had. Women underreport.

4) You better have a good memory if you want to date a lot. In case you don't, call everybody "honey" to avoid mix-ups and make a cheat sheet on each with the name of their dog, their favorite movies, wines, and sexual positions. Failure to take notes will make pillow talk a minefield. If you are compulsive, go ahead and make a chart.

5) Promise little, deliver much.

What We Found

Probably because the ads are free and largely uncensored, Craigslist has become "Hook-Up Central" on the Web. There's no long questionnaire and no profile required as there is on other dating sites. There's just a bunch of hungry people looking for everything — large breasts, big dicks, big beautiful women, skinny transvestites, long-term partners, friends with benefits, illicit affairs, spankable lovers, submissive studs.

The unspoken acronyms behind online personals are HIV, HPV, HSV, and HepB. Sexually transmitted diseases are the scourge of the modern gal navigating her way around Craigslist. Studies show one of the highest rates of new HIV transmissions is currently among women over forty. Just as a middle-aged woman knows she is ultimately responsible for her own orgasm, she also knows she alone is responsible for her own sexual safety. If a man won't agree to wear a condom during sex, the thinking woman gets out of bed, gets dressed, says goodbye, and doesn't look back.

Some people who date on Craigslist are careful, some are not. Some couples want full blood work and a credit check before they'll swing; other couples bone strangers at the Power Exchange with just a few words beforehand.

But for a heterosexual woman who wants to get safely laid, there's a fully stocked candy store on Craigslist waiting to be robbed blind. On a recent Sunday night there were 1,000 men in the Bay Area looking for one woman, any woman.

Most of the ads were written in a vulgar and tasteless style which didn't even tempt an answer. For instance: "I often travel and find myself bored in a hotel room and not really interested in another half-assed handjob from some pregnant meth-head for $100. ... So, I'm doing something very uncharacteristic: thinking ahead." This man seemed to be looking for women to meet him in his hotel room the next time he was in town. His ad said he was "well-versed in the appropriate acts and mechanics" and able to "control myself so that everyone has a good time." But though we like a man who is proud of his skills, he pissed us off by equating us with hookers. And his characterization of prostitutes as "pregnant meth-heads" is incredibly offensive.

Other ads were more tender: "Please, I feel so lonely," or "Please I just want to hold you." Many of the men who post on Craigslist are married, and some are upfront about it. There is an endless variety of enticing, amusing, and erotic messages. It's never dull.

Neither of us ran our own ads; it was more fun to see what the guys were offering. Lily answered ads in the Men Seeking Women section while Anna looked in Casual Encounters. Anna was okay with the explicit nature of that milieu, and the ratio of men to women worked in her favor. Anna thinks like a guy anyway: have sex first; if that works out, see if love follows.

Nearly every Craigslist ad included the poster's alleged age and geographical location. We answered ads that ranged stylistically: some were hilariously funny and tongue-in-cheek; some showed intelligence and creativity; others were just plain romantic. A good vocabulary excited us: one guy claimed he was a "naughty sesquipedalian." A very funny ad entitled "Hideous Freak of Nature Seeks Sympathy Sex" included a surprisingly attractive photo of a buff male torso in briefs. Often one of us was the only woman to respond to an ad — that is, the only real woman. There are enterprising escorts, cyber-bots, and pay-to-view porn scams galore that spam male posters.

Many ads have photos, not just prose. This tactic increases the chances the posting will be read, but not necessarily that it will be answered. After all, the most common picture is the erect phallus. But, without a ruler or other scale reference in the photograph, a gal is skeptical. You also find narcissists in cyber-space: "You will suck my cock. You will lick my balls. You will do it all to ME." C'mon guys, you've gotta give us a reason to hit the reply button. What's in it for us?

Once we answered ads, we sought photos right away; no need to invest 2,000 words in someone whose face or body didn't appeal to us. We sent current G-rated portraits to a new contact. Current is the key word here; people on Craigslist frequently post photos taken at least ten years earlier, or photos too dark or too far away to show details. Men send photos posing in front of motorcycles, sports cars, and boats; we're guessing they think these props boost their sex appeal or give the impression that they have money. We didn't give a whit about the props; it was the smile, the pose, the overall confidence that drew us in. The tackiest photo is a picture of a guy smiling with a woman's arm over his shoulder, but the rest of her is cropped out.

The web etiquette we prefer: a compliment from a guy when they received our photo, as preparation for stage two. Flattery is nine-tenths of seduction. Sometimes a man's picture isn't as enticing as his ad or his initial verbal foreplay, so a friendly but firm rejection is in order: "I don't think this is going to progress any further, but I wish you good luck and happy hunting."

Did we use the now-clichéd "three-date wait" before going to bed with the men we met online? Not always. Did we throw out the rule book, cloth cover and all, and go against the advice of every therapist, professional matchmaker, and guest on Oprah by sleeping with men too soon? Yes we did. There is animosity in online forums about this; some women complain that women who bed men on Craigslist right away are spoiling the dating scene. They claim that if men don't have to buy dinner or court a woman in order to get her in bed, they won't. It's the old why-buy-the-cow-when-the-milk-is-free argument, to which we say, "Give us a break." We didn't intend to upset the natural order. We just wanted to have fun.

And, now, some of the dates:

A Cunnilingus Expert

One of the first posts Anna answered was from a 55-year-old guy who said he would be happy to give cunnilingus for an hour — no reciprocation needed — and he was "not weird."

Anna: "I love cunnilingus. But after an hour I would need ... something else. Are you for real?"

Arthur: "Yes, I am for real ... girlfriends have remarked how uh, dedicated I am when it comes to that activity. I thought it would be fun to find someone who appreciates that. So tell me about you!"

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