I’m a 24-year-old straight female. I just moved to a new city where I don’t know anyone. So the other night I hung out with a 21-year-old jock from work. We went to a bar and eventually wound up back at his apartment, where we both smoked pot. I was thinking he was a muscle-bound meathead, so to shock him I told him a story about one of my male friends wearing a skirt. He kind of exploded and said, “You have guy friends who wear skirts? That’s weird, because I like to dress up like a woman and it turns me on and I really want to be a girl and I want to be pretty and I have these huge muscles because I’m fighting it and I’ve never told anybody this before and I can’t believe I just told you and it’s probably because I’m drunk and do you think it would be OK if someday I dressed up for you?”

I swear it was like that–one big run-on sentence. We talked for four hours and he says that he’s not gay: he just wants to be a woman. The strain is really getting to him, he said, hence the heavy drinking and pot smoking. I suggested therapy, not to “fix” him but to help him get to a place where his desire doesn’t make him so unhappy. Now I’m not sure what to do. I can tell that he’s crushing on me. He was even before he told me his big secret, and now that he’s confided in me his crush has intensified. I wasn’t really interested in him to begin with, but I must admit his admission makes him more appealing. I really do want him to dress up for me. I’m just not sure that I’m ready to deal with his reaction when I don’t want to live happily ever after–especially if he sticks with the idea of becoming a woman. I’m not sexually interested in actual women.

Would I be helping him come to terms with his identity by taking part in his masturbatory fantasy? Or would I be scarring him for life since I’m not interested in anything long-term? I’m afraid that if I reject him now he’s going to think it’s because of the cross-dressing. –Told Very Titillating Secret

There are two things you want here, TVTS. You want to see the muscle-bound 21-year-old dressed up in women’s clothes for kicks, and you want to see the muscle-bound 21-year-old in therapy for his own good. So why not make dressing up for you contingent upon his finding a therapist?

Tell him you’re tempted but you’re not going to go there if you’re the only person he can talk to about this stuff. If he wants to mess around and explore with you, fine, great, you’re game for that. But that’s all you’re signing up for. You can’t be his therapist, and you’re not making any commitments. Explain to him that if you knew you were the only person he had to talk to about his desires you’d feel obligated to continue seeing him even if you decided that the relationship wasn’t working out. He’ll have his first therapy session scheduled a half hour after you get off the phone.

This past weekend I went out to a gay bar in Las Vegas. I consider myself a hot 26-year-old guy, but my sex life is lacking, as I’m somewhat shy and closeted. Well, several hours and drinks went by without so much as a glance from another boy, when who should walk in but sex on wheels himself. He was a dancer in a Cirque du Soleil production, 22, with looks and a body that could kill. We talked for a while and played some pool, then decided to go back to my place. When we got home I ripped off his clothes and we began to play. Hours later he was starting to fuck me with a condom on. Then I realized the condom had slipped off and that he was barebacking me. I immediately got up and asked him if he was clean and he said yes, even though I was too freaked-out to continue.

Am I being paranoid worrying about my chances of getting a deadly disease from this encounter? I don’t think he came in me at all, and he was only barebacking me for like a minute or less. Please help. My sanity depends on it. –Screwed a Circus Kid

PS: Yes, he did do some circus tricks for me.

If your sanity depends on hearing me say something like “There’s no way you could’ve been infected by that circus kid,” then my response is going to drive you out of your mind. There are plenty of hot 22-year-old HIV-positive guys out there, just as there are plenty of hot guys who got infected with HIV under the circumstances you describe. Sorry, SACK, but there’s HIV in precome, anal sex is the most efficient way to spread HIV, and not all guys who claim to be clean are telling the truth.

So what do you do? You go see a doctor, get tested for HIV and everything else, and find out whether it’s too late to take an emergency course of HIV medications. The Centers for Disease Control and Prevention recently advised doctors to start making a monthlong course of antiretroviral drugs available to people who are accidentally exposed to HIV. (It used to be made available only to medical personnel who were exposed to HIV on the job.) Dr. Josh Bamberger of the San Francisco Department of Public Health had this to say about the CDC’s new recommendations: “If you had unsafe sex while you were drunk or had a condom break, you should take these medicines.” Sounds like you, SACK.

Finally, while plenty of guys have been exposed to HIV under the circumstances you describe, there are also plenty of guys out there who’ve had a condom break on them but haven’t wound up with HIV. To save yourself from this kind of anxiety in the future, you should reserve anal sex for guys you know and trust. There are plenty of other things you can do with a 22-year-old Cirque du Soleil performer.

You mention quite often in your column the importance of couples being open to one another’s sexual interests. Usually these interests are way out there. My issues are completely mundane. I would like more foreplay, in the form of my boyfriend paying more attention to my boobs. I have tried to talk to him about it, but he becomes incredibly angry and defensive and tells me I’m being insensitive. “I don’t think you’re insensitive for wanting me to suck your dick,” I tell him. “But you like to suck my dick,” he says. I have just about had it. Any advice? –Sensitive Boobs Need Lovin’

Yes: DTMFA. And if you’re just joining us, SBNL, DTMFA stands for “dump the motherfucker already,” which is what you need to do. Your boyfriend is a rude, insensitive asshole and doesn’t deserve to have a girlfriend who likes to suck dick.