The One Where I Lost My Virginity

The first girl I ever slept with was also the hottest girl I ever slept with, and if you're my first ex-wife and you're hearing this for the first time, I was lying to you every day.  I say "girl" and not "woman," as a favor to her, because while we were both nineteen years old, she could be described as a woman, while I, at 5'4" and 125 lbs, could not have been mistaken for a man.  I'm trying to save her from the pedophilia charges, though I suppose at this point the statute of limitations has passed.  I had no business sleeping with this girl.  I have a very strict 1-10 rating scale for women, modeled after the IGN scale, which is the most incel thing I’ve ever written down.   This is ironic because I'm a 7.2 on a good day, and at the time I was an even 5.0.  I grew six inches as a sophomore in college, and I do feel like that added 2.2 points to my rating.  This girl (let's call her Kylie for the sake of the story, but that is not her real name) was a 9.5, and that’s a conservative rating.  IGN calls anything over a 9.0 “incredible,” and that is an apt description.  She was breathtakingly beautiful.  You couldn't keep your eyes off her.  Not only that, but she was charming and funny.  I was smitten with her the first time I laid eyes on her, which happened to be during a driver's ed lesson.  You know how everyone is required to do so many hours as a driver and so many hours riding along while other people drive?  In this scenario, she was the driver, and I was riding along, which is also a good metaphor for our first sexual encounter.  She made an impression right away.  She was funny as hell even as she was learning to drive, which is such a stressful thing to do.  I brought this up to her later, and while she remembered fondly the hilarious jokes she made, she did not remember me being in the vehicle.  I'm not surprised.  She probably thought at the time that I was the driving instructor's young child.  Anyway, this was an impressive girl (which she was, at the time; we were 16).   When the hour was over, I was way too chickenshit to ask for her number (I don't think this was ever even remotely a possibility, just a fantasy), so that was that.

               Fortunately, though I did not know it at the time, one of my best friends (the incredibly handsome fella seen below) was dating Kylie’s best friend, and she invited my friends and I to a party at her house a few years later.  Now, of course, that girl is still one of my best friends, because how could I not dearly love forever someone who facilitated my greatest underdog story?  I remember that I was drinking Smirnoff Ice, a telltale sign that you are not old enough to have good taste.  This was before that horrible trend where if you handed someone a Smirnoff Ice, they were required to chug it, setting their internal organs ablaze.  I think we can all agree that Smirnoff is the second worst I.C.E.  Anyway, my friends were talking (as they loved to do) about how I was still a virgin.  Young men are mean as fuck.  I can promise you that I gave it back to them just as much, though when you're 5'4" other men tend to not take you very seriously.

                Somehow, my virgin, short-king status did not repulse this goddess of a woman.  Looking back, it may have actually worked in my favor.  She certainly was doing me a favor.  We somehow ended up in a side-conversation, and eventually, Kylie looked at me and said "will you kiss me already?"  That's right, she literally had to ask.  At no point am I the hero in this story.  We made out for a bit, and then I did the one manly thing I did all night, which was to say, "want to go upstairs?"  And the rest is history.  I walked into work the next day, and a co-worker of mine actually guessed that I had lost my virginity the night before because, as he said, "you're walking like you're proud of yourself for the first time in your life."

                Now it's time to play a little Monday Morning Quarterback, and break down why I think this all happened to me.  As I said, Kylie’s  best friend is still one of my favorite people (I showed my gratitude to her for her wing-womaning by giving her a life-size cut-out of Captain Jack Sparrow, which is still one of the best gifts I've ever given).  After my first divorce (two-time champion), I would ask her how Kylie was doing.  You see, I knew that my sexual prowess had grown immensely (how could it not have?), and I wanted a chance at a do-over.  This wasn't greed or selfishness, though Lord knows that I would have of course enjoyed getting to be with her again, but a desire to pay her back for the extraordinary favor she did for me.  So, in checking in, I was trying to ascertain if Kylie was single.  I am 90% sure that my friend always knew what I was up to, in that way that women always seem to know.  Every time I tried to find out if Kylie was single, my friend would get this twinkle in her eye, as if she was thinking "let it go, you dumb piece of shit."  Kylie was never single any of those times, and eventually I ended up meeting and falling in love with my second wife.

                After the second divorce (he did it again, folks!) I asked my friend how Kylie was doing again, but this time out of genuine curiosity instead of with an ulterior motive.  My friend told me that she was happily married...to a woman.

                And then a theory started to take form in my mind.

                Think about it.  If you were a nineteen-year-old woman whose sexual proclivities were leaning towards the same sex, and you maybe weren't ready to explore that yet, wouldn't it make sense to choose a "man" whose features were super feminine?  Like the opposite of Gina in "40 Year Old Virgin?"  I may have been a 5.0 as a man, but I was 5'4", 125lb, clean shaven (by default, not choice) and let's face it, cute as a button.   Maybe I was a 7.0 as a woman.

See? Cute as a Button. This picture was literally taken that night, isn’t that fun? I’m on the right, by the way. My buddy Greg, on the left, did not have these kinds of problems.

                Anyway, that theory could be completely off-base.  Perhaps she was just a girl out there having a good time.  Maybe she was taking pity on me.  Or maybe she actually liked me, although that hypothesis seems just as unlikely to me now as it did when I was nineteen.  No matter the reason, my therapist has me focusing on gratitude these days (I'm paraphrasing this, but it's something along the lines of "aren't you grateful you're not married to someone who makes you just as unhappy as you make them?") and there aren't many people who I'm more grateful to than Kylie.  At a time when I was not very confident, she made me feel like a world-beater.  I hope her wife is as hot a woman now as I was in 2006.