Nearly 60 and Loving It

Q: I am a woman nearly 60-years old and quite well off. I have become attracted to a man in his early 20s. In fact, he's finishing college this spring. He's bright and intelligent and young, and he makes me feel young again. He escorts me to opera, ballet and art gallery openings, but truth be told I'd want to be with him for the sex alone. It's better than anything I've ever known—intense, emotional and frequent. He's taught me about anal sex (which I've never been brave enough to try) and things like pocket rockets and ben wa balls. Sex with him is like a whole, forbiiden world I've loved exploring. The problem is my friends, family and his friends and family. On his side, everyone thinks he's doing something awful spending his time with an old woman. On my side, everyone thinks he's after my money and just wants to live off me. They are making life difficult for us. I'm in this for the ride and have no illusions that he loves me. I give him gifts because I like to and I can. Is there anything wrong with that?

Anne: It could be said that you are leading him down a bad path, encouraging him to rely on a woman for his livelihood. However, if both of you accept the rules of the game you've started, I don't see anything wrong with what you're doing. I would advise you not to sign anything.

Dee: Good golly. You're almost 60 and you snapped up a young 20 something guy?? How the hell did you do that? Conversation, escort duties and all the fucking you can handle (or maybe more, dare I hope?). Life has treated you well woman! Tell those screwball friends and family that they're just jealous and if they can't get with the program, to buzz off. Take life by the horns! You can't make your friends happy and they shouldn't have the power to fuck up your happiness.

Older But Maybe Not Wiser

Q: I'm what's come to be known as a cougar. My boyfriend of a year is 12 years younger than me. I'm…let's say past the legal drinking age by about 25 years and he's in his 30s. He seems perfectly happy with our relationship. I love parts of it (especially the frequent and fantastic sex), but I get nervous going out with him. I keep thinking everyone's staring at us and wondering how much I'm paying to get a young stud for a date. What I think they're saying behind my back makes me feel like a slut, not a nice man's lover. If we could stay home, just with each other, I'd be more content, but he's very social and likes to be out with his friends. What should I do?

Anne: It's a cliché to say that if the roles were reversed—if you were a man and he a woman—no one would think anything of the situation you're in. You are woman. Let's hear you roar. I say try to enjoy your relationship—he seems to be.

Dee: OMG! You are being fucked senseless by—in your own words—a stud, and you're questioning what? Why he's screwing you? Something about your technique must be good. Then are you asking why he takes you out with his friends? He must not be embarrassed by your looks or manners. So you're wondering why he "seems perfectly happy" with the status quo? Lady, you must be doing something right!!!!

Now, if you think there's something wrong with what you're doing, like if you think there's something morally objectionable about an older woman being with a younger man, then break it off. Send him away to make some other older woman happy. Otherwise, relax, smile and enjoy your good fortune—plenty of other women would love being between your bed sheets.