Dear Dan —
I am writing about a friend. By all appearances, he is straight. However, on more than one occasion, he has gotten drunk and tried to hook up with a transvestite or a person who could have been one. In one instance, he went to a club and was approached by a really masculine-seeming girl who proceeded to give him head. My friend, in his drunken state, reached into her pants and felt for a pussy only after she started giving him head. On a trip to Las Vegas, he drunkenly picked up someone who I was told looked like "Kevin Garnett in a wig" and was very obviously a man. He tried to take this person back to his hotel, but friends put a stop to it. I just received a message from a friend who is with him on a trip to Europe, who said that he just tried the same thing again with yet another manly looking transvestite type. Again, my friend was stopped before he did anything he might regret. I can understand if these cases happened with transvestites who looked like real women. It's easy to fool someone when he's drunk. However, the situations I have seen personally and have heard about all seem to indicate he is seeking out transvestites. Could he be harboring some gay or bisexual tendencies? I've never seen him act this way when sober. Or could he just have the world's thickest pair of beer goggles?
Cautious Lad Observing Developments
When we speak of "beer goggles," CLOD, we refer to someone too drunk to realize that he/she has accidentally picked up—or fucked the shit out of—a type that he/she would not normally/soberly find attractive. But I don't think your friend is getting drunk again and again and going after this particular type again and again by accident. Once? Yes, that could be an accident. Twice? That could be a coincidence. But three times that you know of? Sorry, CLOD, your friend isn't going after these types because he's drunk. He's getting drunk so he can go after these types.
Before we go on, CLOD, a word about the particular term you use to describe your friend's type: transvestite. That word? I don't think it means what you think it means. A transgender woman is not a transvestite, and a transvestite is not a transgender woman. A trans woman is someone who was "coercively assigned male at birth," as they say on Tumblr, but who now identifies and lives as female. A transgender woman may or may not have had sex-reassignment surgery—which means, of course, that a transgender woman could have a dick or she could have a pussy. "Transvestite" is an archaic term for "crossdresser" that no one uses anymore.
Now, I don't know what your friend is looking for in a sex partner, CLOD, but considering his observed pickup history ("a really masculine-seeming girl," "Kevin Garnett in a wig," "another manly looking transvestite type"), it's possible that he's not interested in either trans women or crossdressers.
I did drag for nearly a decade, and there was a certain kind of guy who lurked around drag shows. By all appearances, these guys were straight. But they weren't interested in women, they weren't interested in boys who could pass, and they weren't interested in trans women. They were interested in "girls" who were obviously men in drag. They were interested in guys like me: six foot eight in heels, big tits, 26-inch waist (thank you, waist cincher!), and a latex minidress. I was pretty—I'll tweet out a few pictures to prove it—but I didn't look like a woman, cis or trans, I looked like a great big fuckin' drag queen.
The queens I ran with called the guys who wanted to fuck us "panty chasers." It was an odd choice, seeing as none of us actually wore panties. (Trans and cis women wear panties, CLOD; drag queens wear dance belts over tights.) I didn't know at the time that there was an actual $20 term for guys who were into us: gynandromorphophiles, aka "lovers of males in the shape of females."
So back to your panty-chasing friend, CLOD. I'm pretty sure the reason you've never seen him "act this way when sober" is because booze provides him with the courage he needs before he picks up "Kevin Garnett in a wig" and the alibi he needs after.