Q I’m a 21-year-old bisexual female, and a very sexual one at that. My best friend is also bisexual, but a guy. I’ve known him since I was 14, and we’ve had an extremely atypical friendship. We were each other’s first fucks at age 15—because we were so close, it was surprisingly not awkward. From then on, we’ve hooked up consistently. We both consider each other as sort of half twin, half lover, which I’m aware could be classified as creepy. We have other friendships and romantic relationships on the side, but there’s a mutual understanding that we are each other’s favorites. I love him to death, and I would put him before anyone. The odd thing is, with men, I’m mainly attracted to very macho types, which is so the opposite of my friend. He is the embodiment of a campy queer; feminine with a high-pitched voice. He is very attractive but in a skinny sort of way. On top of all that, our relationship is evenly split between sex and romance and things like gossip and spa time. We share the same interests such as foreign film, art and fashion. I’ve recently stopped living in denial and realized this is a bit of a problem. Do you think this is the result of me growing up? Would you agree this infatuation with one another is unhealthy? What do you suggest we do?

A I’ve been sitting here just staring at this letter for a good half hour now. I’m stymied because I absolutely do not want to be the one to begin the slow unraveling of a truly beautiful relationship. In fact, a big part of me wants to tag along with you guys for a day of seaweed wraps and salt scrubs and then maybe we could rent The Umbrellas of Cherbourg (I’m already trying to impress you by pretending I know jack shit about foreign films) and have a long discussion about Catherine Deneuve’s choice of trench coat (I saw it on the poster that came up when I Googled it—sad, I know, but I love you guys!). Unfortunately, I do think that all these questions you suddenly have about this relationship are due to the fact that you’re growing up. When you’re younger, boyfriends or girlfriends can come and go, as long as you have at least one good friend who totally gets you, and boy, did you luck out on that score. But now that you’re at a point where it makes sense to start thinking about forming long-lasting, nurturing sexual relationships, you’ve got some serious soul-searching to do. Soul-search No. 1: Would desexualizing this friendship give you the emotional breathing space you’d need to start focusing on forming relationships you actually see a future for? Soul-search No. 2: Is it possible that, despite the tonality of his voice and the lankiness of his body, your bond with this guy is so strong that you actually could make a run at the long haul with him? From your youthful perspective it may seem like the goal is to find someone who is 100 percent perfect for you, when in fact, 75 to 80 percent will suffice as long as what you’re getting out of it far outweighs the stuff you kind of sort of wish were there. Either way, now would be an excellent time to talk to your friend about what the ground rules will be going forward. If neither of you sees yourselves in a long-term relationship with the other, the time has come to figure out what it will take (spending a bit less time together, bringing along other love interests when you do hang out, not allowing his penis to enter your vagina) to branch out from each other emotionally without destroying the amazingly beautiful thing you’ve developed over the years.

Q I’m a 30-year-old woman, and my stretch marks are a bit more pronounced on my upper and inner thighs than I’d care to admit. I can only assume it’s from all the years I’ve fluctuated in my weight, but now that I’ve accepted my body, I’m left obsessing over my stretch marks. What do I do when I’m naked for the first time with a new guy? Do guys really care if a girl has stretch marks if she’s attractive, in decent shape and knows what to do in bed? I seem to be growing an insecurity about the appearance of my skin, which is killing my self- and sexual confidence. I am using creams to diminish the lines, but what can a girl do, because you can’t make out in the dark all the time, right? Eventually, your partner will want to see you naked in the daylight/shower/morning light. So do I tell him up front or let him see for himself?

A Here’s what you don’t do: You don’t find yourself making out fully clothed on the couch and suddenly stop the action by saying something like: “I’m really into this, but before we go any further I just want you to know I have a few stretch marks on my body that I’m self-conscious about.” The easiest way to wilt a willing pecker is to get the mind to manufacture all sorts of ill-conceived visions of what lies underneath. Clearly, you haven’t fully accepted your body (which is fine; these things take time and constant vigilance), but don’t just assume everyone else has the same hang-ups as you. Believe it or not, some people actually dig having sex with real live human beings, not just zero-percent-body-fat, muscled-up, body-waxed imitations thereof. When it comes to sex, confidence (even the faked kind) is arousing, and skittishness is a buzzkill. Go into it with a selfish frame of mind: “I don’t care what’s going on inside this guy’s head, tonight I’m just going to let it all hang out and let whatever happens happen.” It will be the most freeing sexual experience of your life.

Every week, some letter seems to rile people up, and this time it’s the one from a few issues back in which a happily married guy got shit from his wife for doing a bit of drunken stripper-boob fondling (it’s actually more innocent than that makes it sound, but that’s the gist). Here’s one reaction I got from a confused gal:

Q While discussing the “what if we were in this situation” hypothetical with my boyfriend, I said, “Come on; if I told you I touched some male stripper’s cock, you wouldn’t be pissed?” He said that male-stripper cock was not equivalent to female-stripper boob. I have to say, though, I think women get the raw end of the deal. What else am I supposed to touch?

A Obviously, someone wasn’t paying attention during their high-school biology class. Female-stripper boob is the equivalent to male-stripper ass, just as female-stripper legs are the equivalent of male-stripper pecs. But even more important than the body part is the intention in touching. If you were to brush up against some stripper cock on your way to touching stripper pecs, I have a feeling your boyfriend would find a way to live with that.

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.

See previous Get Naked