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    Comments AlterNet is resurfacing some of the best and most popular articles published in 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, 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.

    What Are The Best Dating Tips For Men in Their 40s


    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 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. 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. I'm sleeping with them. Actually, that's a euphemism; we have sex. Virtually everyone on Craigslist lies about something: 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.

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    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.

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    There were memorable ones, like Lily's first date, which ended at 3: 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.

    Upending 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 hookup, but equally often, we wrote and received profoundly intimate and revealing letters -- an epistolary of erotic stories.

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    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: 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 non-negotiable," we developed our own special list for middle-aged chicks who date on Craigslist: Three lovers told Lily the potty-mouthed comedian was their "fantasy fuck.

    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. 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. 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.

    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, 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. So, I'm doing something very uncharacteristic: 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.

    And his characterization of prostitutes as "pregnant meth-heads" is incredibly offensive. Other ads were more tender: There is an endless variety of enticing, amusing, and erotic messages.

    Neither of us ran our own ads; it was more fun to see what the guys were offering. 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: Nearly every Craigslist ad included the poster's alleged age and geographical location. We answered ads that ranged stylistically: A good vocabulary excited us: 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 lick my balls. You will do it all to ME.

    What Are The Best Dating Tips For Men in Their 40s


    What's in it for us? Once we answered ads, we sought photos right away; no need to invest 2, 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: Flattery is nine-tenths of seduction.
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