Sleeping Around Craigslist 

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

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The former was the first Craigslist date who understood that the largest sex organ in Lily's body wasn't between her legs. Last summer, Luke spent weekends on his boat at the Berkeley Marina and he and Lily started dating. Luke knew how to deal with a smart woman; if he didn't touch her brain, he wouldn't be touching her body. He was funny, audacious, and he kept Lily engaged and interested, in bed and out of it.

Lily and Luke fell in love. It was synchronicity: they both wanted the same thing — and it wasn't monogamy. Although they live in different states, they still see each other once a month for passionate lovemaking — and lots of adventures; indoor skydiving in Union City, Raiders games at the Coliseum, halibut fishing on the San Francisco Bay, hunting in remote areas of Washington state, and dancing to live music, from Ben Harper at the Paramount Theatre to jazz at Yoshi's.

While seeing Luke, Lily answered Carl's ad. Carl was at the other end of the commitment spectrum: he wanted monogamy and he wanted it right away. Shortly after meeting Lily, Carl took his ad off Craigslist, professed that he loved her, and started introducing her to his friends and family.

Carl thought Lily was "The One" for him and he was upset she wanted to keep dating other men. He put more and more pressure on her to date him exclusively and get serious. Had she entered a strange parallel universe where the guy wants a relationship and the chick just wants sex? "At a minimum, I need a situation with a friendship that's beyond a booty call between boink buddies," Carl wrote.

Does the double standard really still hold in 2008? Can a man belt-notch and think he's "sowing his wild oats," but when a woman does the same thing, she exposes herself to being called a slut? Are we all still in high school?

Lily ran this by Anna. "I would prefer the term "sex-positive feminist," but you can call me a slut if you have to, because there just isn't a word for it in the English language," Anna said. "Maybe 'love goddess' would be a good alternate." Lily prefers the term "Supertramp," largely because she likes really bad '70s music.

This poses a larger question: is promiscuity really possible for women without attachment forming? There's no easy answer. Anna admitted she fell in love "at least a little bit" with every man she slept with. Women are complex social creatures and our sexuality often requires some emotional or cerebral connection beyond just skin and friction. But there has to be friction.

And with Carl, there was some seriously good friction. Carl was expert at orgasm-inducing foreplay. He was a technician with a mission: he helped Lily find her G-spot, and then went further and found her elusive A-spot (a cluster of nerve endings located about halfway between a woman's G-spot and her cervix). Tip: look for a man with really long fingers.

Lily was sprung. She told Carl "I love you." But she knew in her heart she really should have said, "I lust you." Out of bed, Carl was controlling, possessive, a chronic complainer, and could be rather boring. The complete truth was, Lily loved Carl because he was an amazing lover.

She continued to date him for the great sex, but the strain of lying to him took its toll. Guilt stopped her orgasms, even when Carl worked hard to get her there. She was foiled by the mind-body connection. After a weekend of whale watching in Monterey, during which it became painfully clear they were totally incompatible out of the sack, Lily broke up with Carl.

Time is limited, especially for a middle-aged woman, Lily realized. She felt she had wasted three months with a guy who drove her crazy by day — even if he also drove her crazy at night. Carl did not take it well: he sent her scathing e-mails and filled her answering machine with accusatory messages.

After the break-up, Lily was getting closer to knowing what she didn't want. And with Luke, Lily got closer to knowing what she did want.

Lily turned to Anna for advice, who urged her not to settle. Anna also reminded Lily that while they are both late to the game, there's still plenty of time on the game clock.

Ménage à Trois

Despite the languid, Henry-and-June, Paris-in-the-rain romanticism that surrounds the ménage-à-trois fantasy, Anna had to type e-mails for months to try to set one up. She contacted twelve couples and four pairs of men, but not one of these e-mail exchanges led to a single three-way tryst.

Threesomes are a pervasive male fantasy — check out any porn film if you need confirmation. It also is a common post from couples with a female partner harboring bisexual feelings. Anna herself had been pushing away bisexual feelings for many years, and decided she would finally explore them.

Anna used to live as if there were a paradise in the afterlife, but now she lived as if her name were already listed in the hotel register in Hell. Maybe this set-up wouldn't lead to true love, but it would certainly be interesting.

She found that one person was usually much more into the idea of a three-way than their partner. Sometimes it was a man or a woman talking their significant other into trying something a little different on Saturday night. "First we'll post, then we'll decide whether we want to do it." That's the kind of attitude you get when the ads are free.

Before going to a meeting. Anna always asked to hear from the silent partner. She wanted to be sure that everyone who was there wanted to be there. If the eager party couldn't get the recalcitrant party to turn up online, what were the chances of getting them to show up naked?

Anna didn't have a whole lot of meetings. She answered one ad from a couple based in Oregon and met them face-to-face at Peet's on Fourth Street. They divulged that they didn't believe in condoms. Anna could handle garden-variety atheists, but how can you not believe in condoms?

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