I'm a straight male, 21 years old. I love women, I've always loved women, I've always loved having sex with women. However, in the last year, here and there, I've jerked off to transsexual porn. One night, after drinking with a friend and smoking some hash, I arranged a date with a trans sex worker. She was totally womanly, nothing manly about her, except for, you know. She licked my butt, gave me head, and fingered me. I've been on the receiving end of anal play before from girls, so nothing new. But somewhere during this encounter, I became the receiving partner during anal sex. At the time, I was too fucked up to care. But the next day, I started to feel REALLY bad. She was very safe and used condoms for everything. I just can't get past the fact that I did the gayest thing a guy can do. I feel really depressed about this traumatic situation. I can't seem to enjoy my life anymore. I've even felt somewhat suicidal. (I would never kill myself—I wouldn't do that to my family and friends.) I still want to date women and have sex with women. I don't regret being with a trans woman because I wanted to experiment. I've been tested since the encounter to make sure I didn't catch anything. What I regret is her sticking her thing in my butt. Can a single act like this make me gay? Please help.
Wrong Side Of Wild Side
Give yourself a break, WSOWS.
Yes, yes: You did the gayest thing a guy can do—you allowed someone to put a dick in your manbutt—but now you're doing the second-gayest thing a guy can do. You're being a huge drama queen about the whole thing. Stop acting so cray, as the kids say, and repeat after me: One dick in the ass does not a gay man make. Look at it this way: The difference between having a woman's finger in your ass and having a woman's dick in your ass is a matter of degree. If the woman's finger was fine—to say nothing of the woman's tongue—why freak out about the woman's dick? Remember: You don't sleep with men, you're not attracted to men. You made an exception for this woman's dick because her dick is exceptional: It's attached to a woman.
So maybe you took a longer walk on the wild side than you might have if you'd gone on that walk sober, WSOWS, but thankfully, your sex worker was conscientious and responsible and used condoms. So you didn't emerge from this encounter with anything more devastating than a touch of gay panic. Be a man about this—be a straight man about this—and walk it off, as the football coaches say.
Maybe this will help: Like a lot of gay men, I had sex with a woman before I came out. I did the straightest thing a guy can do—I put my dick in a vag—and it didn't make me straight. You did the gayest thing a guy can do—you let someone put a dick in your ass—but that didn't make you gay. Because you're not gay, WSOWS, and one ride on a trans escort's dick can't change that.
If nothing I've said has made you feel better, WSOWS, maybe this will: Gay men don't hire trans women sex workers. Wanting to be with a woman who has a dick is an almost exclusively straight male kink/obsession/wild side. Gay men are into dick, of course, but what we're really into is dudes. There are gay men out there who date and fuck and shack up with trans men—men with pussies—so not all gay men are after dick. What we're all after is dude.
If our gayness can't be defined solely by dick, WSOWS, then surely your straightness can't be undone entirely by dick.
I recently used the term "saddlebacking" to indicate the position where a man rubs his penis between his partner's ass cheeks as either foreplay or nonintercourse sex. My girlfriend, a regular reader of your column, insists that I used the term incorrectly. Did I?
Rubbed The Wrong Way
You did, RTWW. "Saddlebacking," as defined by Savage Love readers (the Académie Française of sexual neologisms), is when two straight teenagers, endeavoring to preserve an evangelical girl's virginity, engage in anal intercourse. This is a thing that really happens. Since anal sex isn't really sex, according to the abstinence educators evangelical teens are exposed to, many good Christian teenagers rationalize that getting fucked in the ass doesn't really count against a girl's virginity.
The act to which you refer—rubbing your penis between someone's ass cheeks as foreplay or as a substitute for intercourse—is known variously as frottage, outercourse, the Princeton Rub, or "the pearl tramp stamp." But in Chicago, it's known as "the Cardinal George."