Get naked

Q I’m a 26-year-old lesbian, and I’ve started dating a 40-year-old woman. I think she’s great, but I’ve become sexually frustrated. She is funny, nice and good-looking, but she is not super amazing in bed. I have to direct her in positions, where the spots are, etc., and I’m sick of it. She has a high-paying job, but her coworkers are assholes to her, so it makes her insecure. I’m afraid if I have a talk with her or buy her a book on how to please a woman, she will have a freak-out and be really upset with me. I once tried to give her a lesson, and she basically told me she felt too much pressure to perform now and freaked out. Is there a good way to do this without hurting her feelings? I really like her, but the sex is boring me. I don’t know how much longer I can be frustrated without saying something or getting it somewhere else.

A What’s this? A letter from a real live lesbian? Do you know how rare it is to see one of those in my inbox? Thank you, thank you, thank you for trusting me with your sapphic dilemma; now maybe more people from your community will feel okay about making their voices heard around here. But let’s move on to the issue at hand: First of all, I commend you for being so considerate of this woman’s feelings, but I don’t think tiptoeing around this problem is going to be beneficial for anyone. I know it’s a hard lesson to learn, but it’s the wise human who can distinguish between well-meaning criticism and the kind of put-downs that can happen at asshole-filled workplaces. Trust me, this woman is not going to feel good about herself if you just suddenly break up with her or if she finds out you’ve been cheating. I would sit her down again, tell her all the things you think are amazing about her and your relationship and then tell her that the only issue you have is that you’re feeling a bit unfulfilled in the sack. Throw in a “it’s probably just my high-maintenance body” before “but I really want to work on improving our sex life.” That’s when you trot out two copies of a book on how to please a woman (the message is: “We both have something to learn from this”) and tell her how much it would mean to you if she read it. Frankly, this will be a good test of how much she can put aside her own baggage and concentrate on your needs. Hopefully, this will work things out, but if she either doesn’t get better or doesn’t even bother to try, I think you’ll have learned enough to make an informed decision about whether this relationship is right for you.

Q I’m a guy who has a thing for transsexuals and transvestites but consider myself straight. I recently had a massage from a guy from Craigslist—sort of testing the waters—and while it was exciting jerking him off (which is what I wanted to do), I found that I was not turned on by him in the least physically. My question is, if you’re not turned on by men at all, but are by men who look like women and you’re willing to do gayish things, does that have a name? Besides horny?

A It may not have a name that is socially agreed upon, but I would call it being “sexually idiosyncratic.” You’re simply listening to your own specific sexual desires, and it’s okay that they don’t fit into a certain box. If you talked to various “straight” and “gay” people, you would discover that they have a lot of little quirks that may not comport with preconceived notions of what it means to be a certain orientation, but it’s really not a big deal. Just do what your libido is telling you to do (within reason, of course) and don’t worry about what the Kinseys of the world have to say about it.

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.