Confessions Of A Failed F*ckboy

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The loss of my virginity as a 16-year old was proceeded by one of the most traumatic events in my teenage life. When I say traumatic, don’t get me wrong: it wasn’t traumatic the way, say, living in Syria and having your entire village unexpectedly blown up while you were sleeping, would be. It was traumatic for a boy living on Long Island and trying to compete with other boys on Long Island.

There I was, just going about my business as a teenager — driving to my friend Joey’s — when everything changed. Joey wasn’t home. Neither was Joey’s mom and dad; however, Joey’s sister was. I was incredibly excited when, minutes after I got there, we were quite unexpectedly making out pretty hot and heavy. As a virgin, I never imagined the next series of events. Let me rephrase that. Of course, I imagined the next series of events; but I never imagined they’d actually come true.

Joey’s sister — in an almost clinical way — began taking off all of her clothes.

“This was it!” I thought to myself. “I’m about to lose my virginity! At long last!”

My body, however, failed to cooperate. I had no reason to ever imagine that I would freeze up like that in the heat of the moment. In my most private imaginings, I saw myself as one of those porn dudes (except without the cheesy moustache — this was the eighties). Alas! I was not. The next forty-five minutes was spent in the horrific attempt at getting my body to do its job through the most embarrassing process of utilitarian oral sex until all parties surrendered. I went home feeling less than a man.

This incident as a stand-alone was unpleasant, but the events of the next day are what drove it into the annals of childhood trauma. I went back to Joey’s sister after spending all night and all day planning how I was going to redeem myself, but instead of Joey’s sister answering the door, some bigger, older shirtless dude answered in her place. I don’t remember what I said, but I absolutely remember what I felt.

I am fairly certain that the next 25 years of serial monogamy and baby-making was the result of proving to the world that my parts worked just fine. Even last winter, I remember a one-night stand that I could not have been less thrilled about. I knew that I would never see the woman again afterward, but I had some drive inside of me to see if everything still worked.

A short time after that, I was faced with what most men usually only dream about. Try, if you will, to imagine the most beautiful person your brain can invent. Now, make them a little prettier. Excellent. Think of someone in the best shape you can imagine. Do you got it? Now add some to that. Are you following me? Great. Now once you’ve got all that, make them impossibly brilliant. Then, make them interested in you. Sexually.

Yes. I blew it.

Yup. The only reprieve I got that time around was that it wasn’t some embarrassing circumstance where I couldn’t get it up. In that case, I just didn’t even make the move and we wound up sleeping together. Sleeping.

The next day I figured the most efficient way to torture myself would be to imagine that she was with the shirtless dude having incredible sex. All day long this played in the background of my thoughts. He, as the Olympic Gold Metal lover and myself as the benign innkeeper. It was rough.

I am fortunate enough to have a lady friend who is wildly successful in the corporate world. I save my biggest issues for her. Not because she really has the time for this nonsense, but because she has gotten further in her profession than anyone I have ever known. She understands what it takes to achieve a level of success that few people get to. I emailed her to release the anguish I could not help feeling.

“You might’ve been better off that way,” came the reply later that day. “You’ll see.”

What’s great about that answer is that it doesn’t go into detail. Better because this person will hold me in higher esteem? Possibly. Better because I may have kept myself available for someone that might be more suitable? Could be. It’s not really that important to go into detail about how it all played out. My career as a f*ckboy was circling the drain.

It’s sad. I had always wanted to be known as an aloof sex machine. A somewhat hated but highly sought-after conquistador. I’m serious. I mean, damn, we all know those guys are horrible but we all secretly want to be them. There is no death knell louder than the words “nice guy.” At that point, you may as well buy a Franciscan robe and a pair of sandals because that’s about all you’re going to need.

Meh…maybe my friend was right. Maybe I was better off.


Confessions Of A Failed F*ckboy was originally published in P.S. I Love You on Medium, where people are continuing the conversation by highlighting and responding to this story.

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