Get naked

Q I’m going to be 25 this year, and I’ve been with the same man for four years. He’s 38, so we’ve had that working against us, but we’ve worked it out, and we are for the most part pretty happy together. We’ve both had our share of affairs. Fast-forward past the drama—and the judgment from friends—and we’re actually stronger than before. I respect him more as a human being; and I truly understand that even though people we love make mistakes, they’re still people we love. It’s a personal decision to stay with someone who’s been unfaithful. But even though I’m the happiest I’ve been, I find myself nervous. Before my boyfriend, I was a bit of a whore and I loved it. I miss the variety. I miss the spice. I miss the late-night hookups. I’m not planning for marriage, but when I think that maybe he and I will get married, it scares me. I miss the thrill now and I have found myself nearly pursuing other guys. Not for lack of love for my man (I swear!) but mostly out of boredom. We have a pretty good sex life, but he’s not as much of a freak as I am in bed. But the point is, if I’m afraid I’ll stray now, what hope do I have for marriage? And that fucking adage, “once a cheater, always a cheater”: I don’t know, Jamie, am I?

A You know that part where you said, “It’s a personal decision to stay with someone who’s been unfaithful”? Well, the same thing goes for cheating. It’s a choice, and a bad one at that, especially when you’re with a guy you care for that much. After all the two of you have worked through, do you really want to start that long, laborious process with someone else? You’re clearly far too smart a woman to be such a slave to your sexual impulses, and yet…here you are. Why don’t we do this—repeat after me: I, anonymous, do hereby swear to not let my mind fixate on the stupid things I’m missing (like late-night hookups, for crissakes!) and consequently make bad relationship decisions. Furthermore, I promise to direct my energy into making my boyfriend freakier in bed and more focused on how to prevent me from getting bored and sexually antsy. And lastly, I swear that I will discuss my adulterous longings with my boyfriend and devise a strategy to cope with them. There, now you’re under oath, and God help you if you break the laws of Get Naked.

Q I’m a gay man, and up until I met my current boyfriend I was almost exclusively a top. But the way things have played out, I find myself exclusively in the role of the bottom, which I am learning to enjoy. He’s not interested in switching roles or even performing oral. So, I’ve been stuck with the feeling that our sex life is much less fulfilling than it could be. I’ve brought the subject up and his reply is that he’s just not really interested in other things. How can I help convince my man to switch things up once in a while without making him feel pressured into something he doesn’t want to do?

A Actually, it sounds to me like this guy could use a little pressuring, because he certainly doesn’t seem like the kind who worries much about the contentedness of his partners. I mean, here you are expanding your sexual role (and hole) for him, and he’s going to just blow off your request for oral? I don’t think so. He needs to be made painfully aware of the fact that you’re not all that satisfied with your sex life. Then he might start to realize that relationships require some give as well as take. Don’t feel bad about standing up for what you want. Ultimately, it’s the only way you’re going to be able to make dating a dude like this work.

Send letters to Jamie Bufalino c/o Time Out New York, 475 Tenth Avenue, 12th floor, New York, NY 10018, or send e-mail to sex@timeoutny.com.