Lesbian Craves Geezer Weiner/Geezer Craves Teen Ween

Dear Jen,
I am a lesbian in my mid-thirties. I came out really young and have never been with a man, but for the past ten years or so I've been having sexual fantasies about men in their sixties.  I've never acted on these fantasies but still want to know - why is this happening?  - Who's Your Daddy?

Dear Daddy,
I used to have this great job working in the creative department of a record company where my coworkers and I would help each other with our respective projects.  We'd gather in someone's office and brainstorm for a while until we got bored and started making phoney phone calls or drummed up a round of butt quarters.  One day we decided to play "what's your filthiest fantasy."  We each wrote one down on a small piece of paper, put it in a hat, and pulled them out one by one, trying to guess whose was whose.  I learned that my fellow workers dreamt of things like being suckled by huge-breasted women like an itty bitty baby, and getting eaten out under the conference room table during big meetings.  At the time it was a tad too much information, but it wasn't until they put a gym in the building, and I found myself discussing the new Michael Bolton ad campaign with my boss while she toweled off her crotch, that I quit.

I went on to meet a lesbian who only likes gay male porn, a gay boy who longs to go down on a woman, and everybody knows some straight chick who's gotten it on with her best friend.  What is happening to you is happening to the majority of the population, and all it means is that you have a healthy libido, a liberated imagination, and a secret desire to work in a pipe shop.

We're all under such pressure to follow the tired rules of straightness or gayness or Christianness or whatever, but the world is far too juicy a place to not participate in just because you don't want to get kicked out of any clubs.  So whether it's sitting on the couch watching Columbo reruns with  your hand down your pants, or begging your uncle to take you fishing with his buddies, I sincerely hope you don't let the L word get in your way.

Dear Jen,
I'm a 37 year old woman in dire need of advice.  One of my best friends is a divorced, 41 year old woman who has a 19 year old son.  I've known them both for about 5 years, but only met her son on a couple occasions when he was home from boarding school.  Well, guess who came on to me last time he was home visiting Mommy?  And guess who leapt at the chance to sleep with that fine looking morsel of a boy?

I'd be lying if I said this was the first time I've slept with a member of the younger generation, but I usually don't do it so close to home.  I managed to break it off with the boy without too much drama, but I feel deceitful by not telling his mother about what I did.  At the same time, I feel like since it's not going to happen again, I don't have to humiliate myself, and threaten our friendship, by telling her.  What should I do?
- Dirty Old Lady

Dear Dirty,
Isn't it weird how right as you're about to do something really irresponsible everything drops away - your judgment, your nerves, your pants - and you walk boldly into the storm with unwavering intent.  I think this calm clarity is reserved for only two situations:  those where you're doing something that you absolutely know you should do, and those where you're doing something that you absolutely know you shouldn't.  These, they are special moments.

In your case, an even specialer moment would have been the one where you had an ounce of self-restraint and decided to fish out of a different kiddy pool.  Sleeping with your best friend's child is like sleeping with her freshly divorced husband or the guy she's been lusting after for years - it's technically ok, but it's begging for trouble.

Technically, you don't have to tell her.  He's a grown up, you're a growner up, it's really between the two of you.  Mommy may give you the heave ho if she ever finds out, but this may never happen.  The only question is whether or not you can live with that giant morsel of an elephant in the room.  If you can, don't tell her.  If you can't, take a deep breath, spill the beans and get on with your life.