This post was submitted by Zack Rosen

The most terrible things happened to me this summer: I had sex with a redhead. And it was awesome. The whole thing – his hot body, his sparkling personality, the charming circumstances by which we met – left me devastated for weeks. I’d spent nearly 25 years (or 300 months, or 1300 weeks) not having sex with redheads. In this time, I built up the experience to the top rung in my personal pantheon of things I would do when I was older. I became obsessed with red body hair. With freckles. With the distinctions between chestnut and auburn and strawberry blonde. I nearly fell in love with a straight Irish guy in college and could tell you what he looked like in winter, when the grey landscape of Ohio turned him nearly translucent like speckled alabaster china, and in summer when the sun turned his hair copper and his skin a crocodile brown. Redheads, for me, became Byrd’s Antarctic or Gunther’s Rachel: The may have seemed inconquerable, but I knew that they were there. And I could plot and scheme and make plans and through all my patience and hard work I would someday arrive.

And then I went and ruined all that, all those years of intrigue, by going and getting the thing I wanted. How stupid. In 30 lousy minutes, in a brief exchange of blowjobs and handjobs and later-apologized-for facial ejaculations, I boiled a whole lifetime of anticipation to a scorched puddle of memory and their flaming lustre was gone forever. And I was an English major! I’d read “Ode on a Grecian Urn” and “To The Lighthouse” (and got out of reading “Moby Dick” and “Don Quixote,” blessedly,) and knew what happens to totems: they topple.

And this isnt to say that the experience was awful. It was great, both by virtue of being sex (which can never be that bad) and by being a long-awaited first time. But that’s the trouble with first times: You can only have them once. Corey’s column yesterday about virginity made me think of all the v-cards I’ve gained and lost in the various stages of sexual awakening. There’s the obvious ones, like first kiss, first anal, and first horribly mortifying premature orgasm or mid-sex fart. Then there’s the more subtle ones, like the first time I said “I love you” and meant it, or when I moved in with my boyfriend last June and realized for the first time how happy it could make me to to give my life over, 100%, to another man. But I could move in with forty more boyfriends (though I dont want to, the one I have is great) and never have that realization again.

My sister calls me an “experience junkie.” Some of the things I’ve done, just for the sake of doing them, would make your pubes turn white if I told you of them. But suffice it to say that, as my college’s token slutty homo, I took alot of pride in my mildly checkered past. I used to delight in telling my straight friends who I had fucked, and where, and who asked me to keep my cowboy boots and which security guards had caught us in which campus buildings. And then I graduated and for the first time was exposed to the filthy, resplendent sexual excesses of gay culture. And when I learned that all these experiences were so far from unique, that they actually appeared mundane in comparison with what the mousy man across from me on the bus had done in the course of one hazy weekend in Miami in 1987, something unexpected happened: I started taking pride in all the things I hadn’t done.

It was bizarre. My wallet full of fish stories turned inside out. At bars or parties, I would actually brag to my friends about what rites of passage I’d abstained from. “Oh yeah,” I would find myself bragging,”I’ve never gone home with anybody from a bar. I’ve never had an online hookup. I’ve never even… [dramatic pause]…. had a threesome! My number of sexual partners is in the single digits!”

My audience’s gasps of surprise could have drowned out a jackhammer.

That, though, was years ago. Slowly but surely the gaps in my history of sin were filled in by sweat and groans and things I won’t even tell my shrink. You deflower and deflower yourself until you take a step back and find your yard filled with nothing but dirt and twigs. And what then? Do I spend the next five years in a nunnery so my 30th birthday can be spent rediscovering the pre-adolescent thrills of hand holding? Or do I go the opposite route, paying the shy looking man at the end of the bar to let me do things that Caligula himself had only dreamt of? I like to think this isn’t the case, but I don’t really see a lot of ways to both do new things and stay on the right side of the DC vice squad.

I guess the obvious solution is to just stop worrying and be thankful for what I’ve done and excited to find out what I haven’t. But stoic resolve has never been a strength of mine. So why don’t all of you in TNG-ville answer this question for me: Is it ever possible to do it all? If yes, what comes next?

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