the best sex I never had

I can be a real doofus. In Junior and Senior years of high school, every kegger I’d hook up and make out with this guy named Jay O’Toole. Ok, his name wasn’t Jay O’Toole, but for the purposes of this writing, we’ll agree it was.

We would independently consume enough Pabst Blue Ribbon to make our morals and insecurities comfortably numb, then with a nocturnal sensing system, find each  other in the dark, and start kissing. Usually without speaking.

Why speak? Other than being carbon-based lifeforms, having the right to trial by jury and attending the same high school, what did we have in common? Jay was in with the in crowd—a jock, a blonde demi-god—and I was…whatever it was I was.

Jay and I ignored each other at school. Sure, we’d catch one another’s eyes in the hallways and nod imperceptibly, but pretty much we acted as if we hadn’t been swapping spit—and later other bodily fluids—the Saturday night before. I felt we had an unspoken relationship. We made out. That was it.

So this is how dense I am: Jay and I had algebra together, and every time I entered he would sing a couple of lines from Foreigner’s “She’s as Cold as Ice.” I remember one day in my thirties, when I was showering, and for some reason, my mind wandered to Jay O’Toole and his singing. Oh my god, my epiphany rang out, Jay had a crush on me.

I was willing to sacrifice our love.  I was cold as ice. Damn.

So here is the story of the best sex I never had. (It wasn’t Jay. We did make out, and I did suck his cock, and I did give him measles, or maybe he gave it to me, but that was it. I never regretted not fucking him.)

When I was in college the first time around, I was Managing Editor and then Arts Editor of our school newspaper. We had a reporter who was pretty cute. I could drop names here, because his father is a Pulitzer Prize winning poet and his aunt was a photographer of seismic world renown, but I won’t. I’m going to call him Vlad, Vlad the Would-Be Impaler.

Vlad was a year or two younger than I. He had that combination of dark brown hair and dark brown eyes and almond skin that slays me. But even though he registered as cute, I never thought of him. Never.

I remember going to a party in late spring at the country club in our town. It was one of those magical, slightly misty evenings, and everyone who was anyone was there, tipping slightly in their high heels if they were girls and listing gently in their loafers if they were not.  It was a beautiful, memorable party full of drama and what passed for witty banter when I was twenty-one.

There was a hot tub or two at the club, and we had brought bathing suits to enjoy it. I remember mine was a Danskin one-piece, a wet-looking Lycra number the color of grape Bubble Yum that zipped up the front. I’ve always been a brazen hussy, so I’m willing to remember the zipper as being just this side of wrong.

I was in the tub with a bunch of friends. Chatting. Watching the steam rise and disperse into the cool Vermont air. Across from me sat Vlad. I didn’t think much of his presence. He just never registered.

“You look like a Bond girl.” He said.

Thanks. Great compliment.

Then, under the water, he began massaging my feet, my calves, my legs. Nonchalantly, he took one of my feet out of the water, lifted it to his mouth and began sucking on my toes.

Oh my fucking lord. No one had ever sucked my toes before.

I give very good head. Even great, from the preponderance of evidence I’ve accumulated over the years. And I’ve always wondered what it feels like to have one’s cock sucked. I can only imagine it feels like when I have my toes sucked, but better.

Vlad carefully, mindfully, and with seduction aforethought, sucked each and every one of my toes. It was chlorine-scented heaven in a one-piece.

Did I fuck him? I did not. I don’t remember exactly why, but I probably was waiting for some other guy who didn’t want me.

And Vlad, he just didn’t register. Even with my toes in his mouth.

A couple of years later, I was at the hot dance club in Burlington, Vermont. I know, it is to laugh, but it was fun. It was the place to be. It was the only place to be. And I ran into Vlad.

He looked good. Really good.

He stopped me. We chatted. I don’t remember what it was about. I don’t remember not because my memory is faulty, though it is, but because of what he did to my hands.

He took my hands in his, massaging my palms and my fingers with his, tracing his long poetic fingers along mine, rubbing his fists in the center of my hands, pressing his palms against my finger tips.

He made more effective love to my hands with his than many men have made with their whole bodies.

I swooned. I stuttered. I was speechless.

I was dating someone.

Once more, I didn’t fuck him. And once more, it took me twenty plus years to realize that Vlad had to have liked me. He took major risks in getting my attention, and he was rewarded for his boldness with bupkiss.

And I regret it. Because clearly this man can fuck like an angel.

Honestly, I wonder how my life might have been different if I had recognized what was standing in front of me, touching me, looking into my eyes and hoping for a response. Maybe he just wanted to fuck me. Maybe, though, just maybe it was more than that.

But it seems to me he cared enough to take the chance of my rejecting him. Which I did. More than once. And so his interest in me was great enough to overcome whatever fear he might have felt and whatever walls I put up, which trust me are formidable. Men never approach me. I am rarely asked out. Vlad, I think, liked me. Really, really liked me.

If the gods are good to me, our paths will cross. And I will get a chance to find out.

Moreover, I hope that next time someone as delectable, as fearfree, and as open as Vlad crosses my path, I recognize what it is I’m looking at, and that it doesn’t take me twenty years to have that moment when I say Damn! He likes me!

Comments

[Automatts]

Vlads come and go--as it were--and I suppose that in the form of viciously amazing kissers with GPS guided, wandering hands, I’ve been humbled and awed by his women equivalents. At times it was just that though, the best makeout session in recent memory and then a rapidly cooling trail of evidence that she ever existed. I make bad choices in women…desperately, hopelessly, intergalactically awful choices that have led me to a predictably bemused state of disrepair. Part of those bad choices though, was an appreciation of how wonderful these women were in the moment, even knowing that there was no promise of bankable future moments.
No future can be deeply sexy. Fucked up, but…

[peach]

so, what if you had fucked ol' jay the tool man, would you be any different would you be the same person you are now maybe ol' jay the tool man would have fallen down on the job, so to speak, maybe ol' jay the tool man would have been so bad as to spoil your own sex drive maybe ol' jay the tool man would have been so good that you would have gone celibate because you know it could never be better maybe you would just not be the person you are now...maybe maybe it would have been just another fuck.

[Autumn]

been there, fucked a man like that, and you know what - while the memory still runs in my memory more often then it should, the sex caused more problems that anything else in the world.

Do I regret it? Never.

[James]

I can say this has not happened to me. I dated and never fell in love. Then I met my wife. Are we soul mates? I don't know. I know that she puts up with me, and I cook for her. I love her.

[auugh]

Yes, I've been in your situation many times.

It's a lack of confidence, in my case, that has left me staring at the mirror 5, 10, 20 years later, and going, YOU IDIOT!! SHE WAS TOTALLY INTO YOU!!!

At the time, they did not seem "into me". Women are MUCH more subtle in showing interest than men are. And men are MUCH more clueless and miss the cues, all the time.

If only I'd been better socialized, more of a "people person", had more friends and social life as a young child (instead of being a nerd), I'd have learned to recognize social and nonverbal signals, at least some of them, and been with some truly amazing women in my teens, 20's, and 30's.

Instead, I've consistently been with the loudest, most obnoxious, most in-your-face woman around in any given situation-- the one who woos me by clubbing me over the head and dragging me back to her cave-- or, when I've done the chasing, with someone shy but dramatically overweight and not the type that the really hot guys would go after, because I'd never be able to compete with them. I thought. But many years later found out I was wrong. Auugh!!