Mind Of Man: Losing Your Virginity Is Totes Awkward

Apparently, Brooke Shields lost her virginity at the positively spinsterly age of 22, and regrets not having gotten it over with earlier. When it comes to celebrity gossip, I’m on a blessed time delay. Normally, I’m too busy doing manly things like chopping down trees with my face, flamethrower-roasting suckling pigs, or seducing entire female soccer teams. But truly, this is momentous news, sorry I’m just getting around to it.

It should be of some solace to Brooke that there is no ideal way to lose one’s virginity. It is supposed to be awkward, because sex is awkward. Objectively speaking, it’s kind of funny. Clearly sex was invented by Morgan Freeman as a way to entertain bored angels. Think about it: sex is a lot of butt meat jiggling, legs in the air swaying back and forth like metronomes, and blush-worthy squishy noises. Shakespeare called sex “making the beast with two backs,” but it’s more like “making the squirming eight-limbed octopus that grunts.” The “O” in “O” face stands for “Oooh my gawd, is my grill turning itself inside out?”

She had lost her virginity in high school, quickly sized the situation up, and took over. Forty-five seconds later I was staring at the ceiling wondering how the hell anyone gets to 60 seconds.

Losing your virginity is a preview to all of this awesomeness. The first lesson losing one’s virginity should teach is to have a sense of humor about sex. It is entirely too much to ask that something that feels so good should also be aesthetically pleasing. So buck up, Brooke. Whether you were 22, or in my case, 18, it doesn’t matter when the deed is done. Or where. Or with who. It’s going to be slightly, if not gloriously, traumatic. I’m sure there are those of you out there who would possess the temerity to question my ironclad thesis. Let’s say, for the sake of argument, you lost your virginity and it was nothing but rose-petal storms, silk curtains whipping in the wind, and soft-core porn choreography. If this were even possible then, friend, you have some serious sexual karma to pay off. Here’s hoping, eventually, you experience not knowing if it’s “in” yet. Or you fall off a bed. Or your vagina honks at an inopportune time.

Breaking your actual or metaphorical cherry kind of sucks, and also, it’s kind of amazing. Life is filled with such contradictions, deal with it. Such as: love hurts, and you’ll miss that ache when it’s gone. When I lost my virginity, it was to a woman who knew what she was doing. It was also the first time I was ever naked in front of someone, and Brooke Shields’ claims of poor body image aside, let’s just say my fat wings were fully ready for take off. She knew what she was doing, and I so totally didn’t, even a little bit, and I must have looked like the biggest douche in douche history.

But man, I loved that woman. We met in college. I had spent most of high school recovering from a first and last kiss with an upperclassman whose affections immediately turned to someone who could operate their tongue. My recovery consisted of listening to a lot of punk rock, and touching as many boobs on as many basement couches as possible. When I met my first, however, I was possessed by biological imperatives and a responsibility to my gender. I pursued her like an emo Pepe LePew. Inexplicably, my ploys, poems and petitions worked.

I mean, we were mismatched utterly. She was an incandescent country girl with curly black hair, clever and sweet, a body that bikinis long to wear. And I… wore Hyper Color shirts and quoted the seminal graphic novel, Watchmen. When I’m on my deathbed, or rather, as the woman I love cradles my body after I bravely fended off that marauding horde of zombie ninjas, I will press the pause button as my life flashes before me, Oscar movie montage style, and take a moment to savor that special college girlfriend, the one who tasted like spun sugar. The one with the deep dimples and fantastic breasts. That woman who I first whispered “I love you” to.

When the big moment came, when I finally saw a fully naked woman lounging on my mighty dorm room twin bed, I had no idea what to do. My only frame of reference came from the handful of pornos I had watched with my girlfriend Lubriderm (she was from French Canada.) So, by the sexy light of my desk lamp, which accentuated my innie-outie bellybutton and aforementioned fat wings in the most sublimely unflattering way, I went to work. I grabbed her legs by the ankles, hoisted them up, and, somewhere, a bass guitar started to waa-waa. I played to an imaginary camera, and I had no idea how to get my penis inside of her, because I was holding her legs up. That’s what they did in “Sexbusters.”

She had lost her virginity in high school, quickly sized the situation up, and took over. Forty-five seconds later I was staring at the ceiling wondering how the hell anyone gets to 60 seconds.

I learned a lot that night, and even more in the morning. I learned that waking up next to a woman is better than comic books and beer combined, times infinity. Things got better from that point, but it took practice. I am proud to report that I can last in excess of sixty-seconds. Hold your applause please.

My first time was an epic fail. And a total win. I regret nothing. Brooke Shields should regret nothing. None of you should regret anything. When you’re dead, you’ll regret regretting so much.