Several years ago, while on business in Chicago, I stopped off at a trendy bar in the Wrigley Field area. I wanted to burn off some of the per diem my company had advanced me and drown the sorrows of yet another Cubs loss. I noticed this very beautiful young Latina playfully looking my way in a manner that has been depicted in too many bad movies. I made my way over to her seat at the bar.
After we talked for the better part of three hours, we found ourselves en route to my hotel. She said, in what could only be described as fractured English, that she felt compelled to let me know one very important fact -- she was a transsexual. During my mental undressing of this stunning young girl I hadn't guessed that she was "swingin' a bat." I tried not to play it like it was a surprise, although it was pretty hard to believe anyone would have been able to tell, and so she must have known this was news to me.
I hate to fast-forward over the juicy parts, but it was the best sex I've ever had! It was like something out of a bad Mickey Rourke movie (I guess that is redundant). We were thrashing about and hanging off every piece of furniture in the place until the small hours, much to the dismay of floors 1-50. Since I was very close to Wrigley Field I feel compelled to offer one more euphemistic sexual clarification: I was "pitching" and she was "catching," so to speak. Other than that we did it all.
Years later, I am quite the expert on transsexual culture, surgeries, hormones and most important, the "girls." In fact, while I have had on-again off-again biological girlfriends (and was married for 10 years and divorced my wife for unrelated reasons), none of them have been as hot and half as good in bed as the TS girls I've been with. Now the bio-girls don't seem to -- excuse the pun -- "measure up."
I'd never think of having sex with a guy (in fact the idea is rather repellant), but if I had my choice between a TS and a bio-girl, there would be little to consider.
Am I Gay?
Dear Am I Gay,
No, I don't think you're gay. I just think you have been seeing too many bad movies. But what if I said yes? What if I said there's no doubt in my mind: You, sir, are gay! Would you then feel compelled to start having sex with men?
I don't think so. I'm just making a point by taking the contrary proposition to its point of absurdity. So I think what is actually going on is that you like something more than you expected to, and you wonder what it means about who you are. You say you have learned a lot about transsexuals over the years, so perhaps you have given some thought to what it is about them that you like. Perhaps you have also thought about what kinds of other men like them. The things you have in common with those men might form a part of your identity, but identity is a composite. Labels aren't very helpful. It's better to just tell the truth and try to be specific.
You are who you are and you like what you like. You're an American and you like to screw transsexuals! So good for you! Strike up the band!
If every woman could be a man for a day, she'd probably know a lot more about what men like. So it's not surprising that the sex with transsexuals is good. It's not surprising that you like it. Chances are a lot more men would like it if they tried it, but they never spent three hours in this particular bar.
None of this means that you're gay. But I'm not sure. Do you want to have sex with men? It's not illegal -- not in most states, anyway. You could do it and find out. But if you don't want to, you don't have to. I think you're just fine the way you are.
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