Awkward Sex Attempts (and Other Common Experiences)

There are times when I try to (almost have to) convince myself that I'm not the only one with the most god awful stories to tell when it comes to interaction with the opposite sex. If it's not saying the wrong thing (or nothing at all) on a so-called "sexy" phone call, I make the wrong move and make myself feel like I'm trying too hard to be "grown-up" instead of letting it come naturally. I can only imagine what I look like to the guy I'm with.

First ever horrible nonsex experience: I got naked for the first time.

First of all, this entire scenario was all wrong. I was 14 and (rightfully) had never been naked in front of anyone before. He had a girlfriend. Granted, he'd asked me out first, but I said no and ended up becoming his best friend. Then stealing him. Did I mention I was a candidate for sainthood in high school? I justified it by being "in love" with him. To top things off, I found out later that he was lying about his age. By two years. (Honesty is one of the sexiest qualities someone can have.) I'm not even going to get into the actual number. Let's just say, I was a freshman and he was a senior.

Secondly, I was nowhere near ready for this experience. I thought I was, but sneaking a few looks at porn and late-night HBO does NOT prepare you for someone seeing you naked and not lighting up with joy the way they do in movies. That might've had something to do with his growing attraction to his male best friend, but that's another story. See, it's that honesty thing I was talking about.

So, the afternoon starts out with him calling his girlfriend and telling her he would be working all afternoon and he would call her later that night. Then he showed up at my house and lay in wait inside his car, ducking behind the steering wheel when I walked home with one of my friends. It was like a scene out of a bad spy movie. When my friend left, he tiptoed up to the door and I let him in. This is where the awkwardness began.

Now, I had gotten my first kiss from someone who was (a) hot and (b) a very good kisser. I had several months of practice under my belt. This did not prepare me. I had invited him to the house under the pretext of watching The Nutty Professor (Eddie Murphy) together. He'd never seen it and I figured we wouldn't get past the first 30 seconds, so it didn't matter. I started the movie and he sat behind me. Like almost a full two feet from me on the sofa. It took him damn near 30 minutes to work his way to my part of the sofa, put his arms around me and kiss me. Badly. I don't know how many ways it's possible to get a kiss wrong, but I think he had them all covered. Wrong angle, didn't know what to do with his tongue, couldn't quite get a rhythm going - it was horrible. I tried to take control of the kiss; it did not help.

Somehow, we moved past the awkward kissing and maneuvered on the sofa so he could help me undress. My shirt came off okay, but then we had to deal with the jeans. I blame this next incident on a few things: My mother's insistence on buying me clothes that were either a size too small (trying to keep me a child) or a size too big (telling me I'm getting fat). These jeans were tight as all hell. Which might be why I wore them. They made my ass look fabulous. Plus, I was nervous and didn't really know how to help him undress me. So, we're positioned on the sofa: me, on my back looking up at him, him kneeling on the sofa facing me and the TV he was still half-watching. He unbuttoned my jeans and peeled them off me. Or, at least he tried. Mostly he succeded in scraping my skin. I tried to wriggle out of them while his "help" got a little more active. This resulted in me popping out of my jeans, bouncing on the sofa and cracking my skull on the arm.

This put a slight damper on the "sexy" feelings I was trying to work up. Trying because he was still watching the damn movie. Honestly, I love Eddie and Jada and them, but it wasn't that funny. He was about to get laid. Shouldn't he be paying attention?

Or so I thought as he had his hand between my legs. Watching the movie. Laughing. Working his fingers. His large, dry fingers. (Cue the KY commercial.) By this point, I had almost given up getting anything good out the experience. I was just hoping he'd stick it in and make it worth my trouble. Then, he suddenly remembered I was there. Meaning, he stopped watching the movie long enough to watch me watch him move his dry hand. Then, he produced the single most awkward moment of the afternoon.

Him: Do you ever think about [girlfriend]?
Me: (disbelieving) What?
Him: You know. Because I'm here with you.
Me: (trying to work up a fake moan so he'll concentrate) No.
Him: Really? You never do?
Me: (eyebrow raised, fake moan stopped) No.
Him: You've never thought about what I do with her? (looks down) How I might've done this to her?
Me: *sigh*
Him: You never thought I must use the same hand, the same fingers and everything?
Me: (thinking: what the fuck did I do? I should've slept with [guy I had my first kiss with])

I closed my legs and kind of turned to the side, effectively dislodging his hand. I pouted like the cute little girl I was and wondered what I had done to deserve this misery. Then I remembered. That falling in love thing. Right. Then he says to me, "You're not ready" and some other BS and goes to wash his hands in the bathroom. Truthfully, I think he was just going to experience the smell of a female with a proper look of surprise (did I mention he was an "actor"?) because I don't think he'd gotten that close to one before. But, he did wash his hands. I just lay there on the sofa, pouting. I mean, really. He was the "experienced" one. He should've guided me through that horrible experience a little more gracefully. But then, he would've had to know what he was doing.

So when he came out of the bathroom, I tried to ignore him. I couldn't. He felt all sorry for me. He mistook my sad expression for one of sorrow that he wasn't going to be sharing afternoon delight with me. I was secretly relieved that I wouldn't be put through slow, awkward sex that day. I was also pissed that I'd wasted a perfectly cute outfit and homework time on him. And ruined future Valentine's Days (when I found myself sitting on that same sofa) forever. Thankfully, we got a new sofa a few years ago. Not that it improved Valentine's for me, but whatever.

He helped me get dressed and then I walked him to his car in my socks. I couldn't believe that disaster had taken almost an hour! Even worse than his performance, he wanted to take the movie home and finish it. (Honestly, I think he might've just wanted to go home and rewind to the part where Eddie was dancing around in spandex, but I'm going to pretend that possibility never occurred to me for now.) Sometime during our afterbadnonsex talk, he blamed the bad kiss on me, told me he'd wait till I was ready and basically said it was all my fault. Right. Because when a girl you supposedly love is throwing herself at you, the best way to communicate how you feel about her is to laugh at a few tired fat jokes. Really, I wanted him to be honest with me, but I wanted him to be honest with himself more. It takes two to make it go right, but apparently it only takes one to make it go horribly wrong.

Okay, that's it for this trip down memory lane. For the curious, let me just add that I officially found out about his boyfriend a couple of months later, ignored it and kept trying to make it work. I had suspected since the previous December, but I thought my magical kitty could "fix" him. Oh, to be 14 again. His girlfriend didn't find out about his boyfriend until later that summer. Hilarious that it took her that long, but still. She stayed with him (and his awkward hands and bad kissing) off and on for an additional two years. At least I had the sense to get out a few months later.

But not before a few more bad kisses. I thought I could teach him. Why didn't I learn?

Maybe next time I'll write about what happens when you mix bad phone sex, awkward positions and references to a guy with passports from four countries (and different looks on each picture) as a "terrorist." Good times.