I am a young gay man who has been so freaked out by the idea of catching an STI that I haven’t gotten with anyone for two years. But last night, I hooked up with a cute 21-year-old FTM trans boy, and maybe because it was a person with lady parts, I let caution go, and no condom was used. How worried should I be about having made a baby with a person who is way too young to have one?

> Cautious Homo In Loopy Dilemma

P.S. He is on hormone therapy.

Here’s a good rule of thumb for all you sex-havers out there: a new sex friend who’ll have unprotected sex with you has probably had unprotected sex with other sex friends. Yes, yes, typically cautious people have been known to “let caution go” on rare occasions. It happens, CHILD. But the odds that two typically cautious people will both simultaneously decide to “let caution go” and have unprotected sex with a brand-new sex friend just this once are pretty slim. “This person who’s having unprotected sex with me is having unprotected sex with other people” is a far more reasonable assumption than “This person who’s having unprotected sex with me would never have unprotected sex with anyone else.”

Which means you should be less concerned with pregnancy—your sparkly new concern—and more concerned with that old concern of yours, sexually transmitted infections. The odds that you got that FTM trans boy pregnant are pretty slim; there’s only a one-in-20 chance that a single act of unprotected penis-in-vagina sex will result in pregnancy. The fact that this guy is on hormone therapy may make him slightly less likely to conceive. But if your cute hookup was having unprotected sex with others—if he wasn’t making a very special exception just for you—then you’re at greater risk of acquiring an STI than you are of acquiring an heir.

Go and get tested, CHILD, and while you wait for your results, ponder this: health workers and HIV-prevention educators tell me that the more freaked out someone is by the idea of catching an STI—the more paralyzed by fear someone is—the likelier that person is to have unprotected sex when they do have sex. Your recent experience is common enough to be a depressing cliché. So working to conquer your irrational fear of STIs—and actually having sex once in a while—will leave you less likely to contract one.

Twenty-one-year-old furfag here. I consider myself a bi guy, I check out men and women (femmy guys and cute girls), but I’m a virgin. I have a boyfriend of three years, and we do role-play online. He’s sweet, nice, and sometimes a stubborn dick, but otherwise always there for me. We met online, and I fell in love with his personality two years before we traded pics. He is totally okay-looking, average, and I am fine with this because he’s a sweetheart. He’s also four years my senior. I’m working on my bachelor’s and trying to get into graduate school. He swears that no matter where I go, he’ll follow me. Is this a strange relationship? I know it’s unorthodox, but is it a bad move? I don’t want to ruin his life. What if we meet and try gaying it up and I’m not into it? (“Ha! You ruined your life. I’m not even into men.”) It’s my senior year, and I think I love him. I’m certainly more fond of him than any other relationship I’ve been in. Sex doesn’t hold a big interest for me, and porn doesn’t do anything for me—gay, straight, it’s like watching a sweaty, breathy anatomy class. I’ve never even masturbated. Am I going about this wrong?

> Fella Unsure Regarding Feelings About Gayness

Maybe I’m behind the times—maybe I just don’t get this “online relationship” stuff—but I don’t think two people who’ve never met in real life (IRL) should be planning a future together. Attraction is about more than just shared interests, emotional compatibility, and kinks in common. There’s an ephemeral, unquantifiable aspect to attraction, something that can only be established when you’re face-to-face/tongue-to-tongue with someone. Call me old-fashioned, but I don’t think you can know for sure that it’s love—a love worth moving across the country for—until you’ve tasted each other’s spit.

Don’t get me wrong: I think it’s great that you two got together, FURFAG, and I don’t doubt that there’s a real connection. One of the wonderful things about the Internet is the way it brings people with rare kinks together. And sometimes people with uncommon kinks have to go to uncommon lengths to be together—which can include taking a big risk like moving across the country to be with the furfag of your dreams.

But before you do that—or before you let him do that—you need to meet in person at least once to establish that (1) you’re actually in love with each other, and (2) you’re actually into men. You can’t resolve those doubts until you’ve acknowledged them, FURFAG, which means a truth-telling, doubts-airing, non-role-playing Skype session is in order.

I’m a 19-year-old gay guy in a relationship with an 18-year-old gay guy (for nearly four years). My boyfriend and I have a good sex life, but I rarely get to top him. We’re both versatile on paper, but the actual act of getting penetrated is almost always painful or uncomfortable for my boyfriend, even with plenty of lubrication and preparation. I’m frustrated because I know it’s not his fault, but I sometimes feel that he isn’t putting in enough effort to try to bottom for me. Additionally, it’s hard for me to understand how he feels because bottoming is never painful for me, and I enjoy it a lot. We’ve discussed the possibility of me topping another guy (alone or in a threesome), and he isn’t opposed to the idea, but I’d much rather it be him. Is there any way we can make bottoming pleasurable for him?

> Ready To Top

The best way to determine if your boyfriend is a natural-born top—not into getting fucked, never will be into getting fucked—is to sideline your dick for the time being. Explore his ass, and his capacity to experience anal pleasure, without fucking him. Get some small anal toys that aren’t designed for in-and-out play, RTT, but set-and-forget play—a few butt plugs, one or two small vibrating eggs. Pop one in his ass and then let him fuck yours. If you can take the pressure off your boyfriend while getting a toy in him, RTT, he may begin to associate having something in his ass with pleasure. If he can do that, he may be able to graduate to your cock. Good luck.

I’m a 21-year-old gay boy with a kinky side that I keep pretty private. (Total twink—you wouldn’t know what I’m into by looking at me.) I went to London in June to get with a guy who has an amazing dungeon. I spent a week being his slave boy and getting tied up and caged, and I had a blast. He posted some pictures of me to his porny Tumblr, which I was okay with, but some gossipy vanilla boys I go to school with recognized me even though my face was blurred out. NO! What do I say to them?!?

> Kinked Twink

“I had a blast.”