Dear Dan —
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 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.
Dear Dan —
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, 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.
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.
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.