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As someone who knew he was gay from age eleven and was also born by c-section, I was both confident and content with the fact that I had never come into contact with a vagina. But what would I discover if I actually gave this whole "woman" thing a try? After all, I think women are awesome in general, so maybe having sex would turn my "like" into "love." Would I enjoy it? Could I increase the size of my dating pool? With grim determination and thoughts of liberated sexuality, I set out to see.
1 (very willing) woman
1 gay man
3 gay porn magazines
1 bottle of Jack Daniels
Most people agree that it's possible to know you don't like something without experiencing it, like rock climbing or The Hills. So while the idea of female genitalia wasn't gross, it was about as sexually enticing to me as a paperweight. And so — while I had made out with girls in a we're-drunk-it's-funny kind of way — I comfortably stayed away from any downtown action.
The only problem with this lack of experience was that, as an emotional masochist, one of my favorite pastimes was developing doomed crushes on straight men. These would often be guys I was good friends with, who appreciated the way I helped them with their girl troubles (and missed my occasional grimaces of soul-crushing pain). While I would never say this to them — the straight male is a fragile and easily frightened animal — I'd think to myself, "Well, how do you know you wouldn't like making out with me if you've never done it?" I knew it was wildly hypocritical, but that didn't stop me.
So, in an effort to put my money where my mouth was (or wasn't), I decided I would have sex with a girl. It wasn't going to be easy. While in eighth grade girls often went crazy for the safety and dependability of a soon-to-be-gay guy, currently the ladies are not banging down my door. I figured two things: one, this would have to be a girl who was well aware that I was gay. No point in getting someone besides myself hurt in the process. Two, I'd want the actual experience to be as spontaneous as possible. I'd need to keep my wits about me, as I had long ago turned off the part of my brain that noticed any sort of interest on the part of womankind.
All the requirements were fulfilled one particular Friday night. Jenny was not only a good friend, she also had many of the things I look for in a guy. She is taller than I am (not hard, since I am quite short), easy-going, and a hard drinker. That drunken night at my apartment, our conversation turned to our own personal sexual frustrations, which, in your early twenties, is like saying "our own personal oxygen." And that's when I saw my chance to literally do it for science.
"I've been a bit curious, about um... havingsexwithagirl."
"Well," I said, "I've been a bit curious, about um." I clammed up. "Uh, um, uh..." I felt like a fifteen-year-old boy. I said in a quiet mumble, "...havingsexwithagirl."
She looked nonplussed. I drunkenly explained about my straight-guy philosophy, and the nature of my experiment. She considered for a moment. "Well... sure. Why not?"
And so it was on.
We started slow. If this was going to happen, I was going to do it right, goddamn it. We made out on my bed, and it felt like freshman year of high school for both of us. This was the territory I was familiar with. Normally making out with a girl was sort of fun, but knowing that it was the first step in a larger process made me hyper-aware of everything that was different. There was no stubble, for one thing, which I actually missed. And I wasn't sure if I was supposed to touch her boobs — how would I even do that? My arms moved gracelessly, looking for some nook between our bodies to exploit.
Still, the lead-up was not the point, so soon our clothes came off, and it was time. I reached into my drawer for a condom, and had the luck to pull one out that I'd gotten at a sexual-health event a couple of weeks before. The wrapper was adorned with a rainbow background and a stunning picture of a man's ass. It was both perfect and completely inappropriate. On it went.
And then I did it, full-on genital penetration. I know that there was probably a lot more preparation I should have done — going straight from making out to sex seemed like a leap you're generally not supposed to take — but it was truly a now-or-never moment. If nothing else, I was generous with the lubrication — having had nothing but gay sex, it was de rigueur. And if there was anything like an improvement over sex with a guy, it was that the concordance of male and female genitalia — both being towards the front — made missionary-position sex slightly less awkward. To my mind, though, the actual feelings in my junk, through the double screen of alcohol and latex, were pretty much the same. The whole act had a mechanical quality. Make sure you do this, make sure you touch that, and you're in business. Once again I found that boobs only served to confuse me. I knew that they were supposed to be star players in this whole sex-with-a-woman thing, but I was on top of her. How could I touch them without doing the sexual equivalent of a one-handed push up?