Sleeping Around Craigslist 

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

Page 5 of 6

When wooing, pairs of men were much better coordinated than couples. Two men would successfully tag-team Anna in e-mail exchanges until a meeting could be arranged. Among the dates that never went all the way:

Anna drove in the pouring rain to Chow in Lafayette to have beers with Bill and Richard, the friendly, oh-so-normal guy-next-door team. It would be easy to imagine Richard standing behind you at the hardware store, Bill standing in front. Either way, it doesn't matter as the three-way never came about.

Next came happy hour in Sausalito with two overprivileged captains of venture capital. Kevin was quite handsome and aloof. His partner, Neil, owned a yacht and was old enough to be her dad. Anna noticed people at the next table staring at her from behind the men's camel hair jackets. They were listening. As he left, Neil discovered he knew the couple at the next table. Yikes.

Anna had an urbane terrace lunch with Steve, 46, and Mark, 55, at Oliveto's in Rockridge. Unfortunately, Anna found the waiter ten times more irresistible than her dates. Silver-haired Mark interested her, but she couldn't imagine kissing Steve. Now that's a bit awkward all around.

In the end, Anna found these threesome meetings rattling. It isn't easy to flirt with two guys at the same time. And not every pair of men were effective at getting to the rendezvous:

Dick, Chuck, and Anna exchanged a staggering 105 e-mail messages, but only two were written by Chuck. After weeks of voluminous correspondence, Dick finally revealed he had lost his partner. It seemed that Chuck had fallen in lust for Dick. Anna wondered why he hadn't entertained that as a possible outcome from the get-go.


Undeterred, Dick went ahead and answered a foursome ad with Anna as his new buddy.

Paul and Missy were an attractive middle-aged married couple. Dick jumped into an e-mail correspondence with Missy and pretty soon the four found themselves seated around a table of raw oysters at Pearl on College Avenue. The evening went surprisingly well: Missy, 47, was chatty, funny, and friendly. Paul, fifty, resembled Anna's childhood TV star crush — Bob Crane, the colonel from "Hogan's Heroes" who always got the girl.

The next day Missy followed up in an e-mail: "Dear Anna and Dick: Would you be willing for us all to get a STD panel done to share — so we know what each has or doesn't have?" What a buzz kill.

But in a subsequent e-mail Missy revealed that her first husband had contracted HIV and died of AIDS from secret affairs he had had during their marriage. Although she was HIV-negative, Missy had understandably deep concerns about STDs, so the four would lay their cards out on the table. (Missy even forwarded Paul's test results via e-mail as a PDF.)

Anna trooped to the Berkeley Free Clinic for her HIV test. She squirmed when she realized she was old enough to be the intake counselor's mother. Anna tried to explain why a condom wasn't always an easy sell with men in her age bracket — largely because they never had to wear condoms during the go-go '70s. The 25-year-old counselor nodded her head, but it was clear that Anna wasn't gapping the generational differences in sexual mores. Anna was sent off with fistfuls of condoms in every color: mint-flavored, lubricated, ribbed, and twisted. She did learn one thing: not to floss her teeth before, during, or after sex, to reduce the risk of oral-genital virus transmission.

The big night finally came for Dick and Anna to drive to Missy and Paul's condo in San Francisco. Of course, they didn't all have identical chronic STD profiles. What would be the odds of that anyway? Undaunted, Anna brought along every safe sex device available at Good Vibrations; dental dams, lickable lube, vibrators, Saran Wrap, and all those free condoms. That night, Anna shared a peak sexual experience that crushed her bones to stardust.

The next day, Anna visualized her happy future in a group marriage, but that lasted a nanosecond. The interpersonal dynamics of four naked people were exponentially more complicated than a relationship between just two people; and most of us know what a picnic that can be sometimes. In the morning-after e-mails, it was clear Missy felt the swinging foursome was a one-time event, although Anna would have liked to have seen the couple again for another go-round.

The Life Lessons

After we decided to collaborate on this article, the number of dates we went on fell way off. It's tough to find time to have sex when you're writing about it.

Lily dated Luke exclusively in the past few months. Their love grew deeper when, in April, Luke was handed an unexpected diagnosis of kidney disease. What started out as casual sex on a boat in the Berkeley Marina, ended up as friendship caught fire. Hearts can and will be broken when sleeping around Craigslist. And in love, just as in life, there are no guarantees.

Anna remains in the game full-time. We are publishing under pseudonyms to protect our kids and our day jobs, not because we have shame. Truth is, we are grateful to be having the passionate sex we missed when we were younger. We thank the men and women we have met on our journeys. And we share the real list of what we've learned:

Be yourself.

Trust your body and your intuition.

Be honest with your feelings.

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