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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.
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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 non-negotiable," 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.
Terrific e-mail connections don't guarantee a sizzling face-to-face meeting. 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 Map Quest the planned meeting spot.
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.
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.
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. 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.
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.