In Praise of Messy, Awkward Sex

Let’s ditch the script and just have fun…

The first time I had sex, I was shocked by how awkward the experience was. I knew it wouldn’t be perfect — I was young, inexperienced, shy, and, oh, let’s not forget, unbearably ashamed of my sexuality. I definitely didn’t expect things to go particularly well.

But I also had the enduring fantasy that it would somehow resemble if only faintly, something out of a movie. Two bodies slowly and romantically sliding together with little effort, everyone having their happy orgasms ten minutes later.

Of course, it was nothing like that. I was so self-conscious, I made him turn off all the lights before we even got undressed. It was so dark in the room, the only illumination coming from the red numbers on his alarm clock. I could see him taking off his clothes, and I was so nervous, I’m fairly certain I managed to tangle my panties around one ankle as I was trying to remove them.

Then he pulled out a condom and I remember thinking, I hope he doesn’t expect me to put that on him, because I don’t know how. Thankfully, he did it himself, but not long later, the next moment of cheek-coloring awkwardness came when he asked me if I was ready, I said yes, and we both just looked at each other in the darkness, trying to figure out what to do next.

Doesn’t it just kinda slide in there?, I wondered. When I realized that was not going to happen, I genuinely had no idea what to do. That part is never in the movies.

I was still dealing with so much shame around my sexuality that it was a damn miracle I was about to let him put his penis inside me — but the idea of actually touching it in order to get it in there…? Um, no. No way in hell. For some reason, that seemed far more intimate, brazen, and inappropriate to me than him actually penetrating me. (Honestly, I look back at that time and sometimes think I had no business having sex…)

So again, he took care of it, subtly sneaking his hand between us and, let’s say, steering himself into place.

From there, it only got more awkward. Though I can’t say we didn’t have a good time.

When I got into my twenties and started feeling slightly more expressive in the bedroom, I was determined to be an elegant, sophisticated lover and have a sexual experience that looked like it belonged in a movie. It seemed so attainable when I fell for Jay, who was one of the most handsome men I had ever seen. Seriously, most of the women on campus were crazy in love with him. And like any good musician, he took advantage of that, maintaining a network of groupies, each one who no doubt was happy to oblige him with a weekly blow job.

Of course, I thought I would be that plain but soulful woman who would make him understand the true power of love (whatever that means) and we’d soon be rolling in slow motion across his big bed.

Well, no, as it turns out, my determination and his smoky hotness did little for us. When he took me up to his bedroom on our third date, before we had done anything but hug one another, he suddenly came at me, catching me around the calves, and knocking me backward onto the floor. Then he grabbed my face and kissed me.

It was the most awkward damn kiss I had ever experienced (and I’m sorry to say, not the last time a man would tackle me for a first kiss). I didn’t even enjoy it. He was pressing into me so hard, there was none of that tingling, light, teasing pressure that so often characterizes the first kiss.

Thankfully, he eased up as we moved to the bed, but the night continued to devolve into clumsy but eager groping, and then the most awkward blow job you can imagine. Seriously — go to the most inept blow job you could dream of and then make it ten times worse. That was me that night. But hey, I tried (which is more than I can say of him).

After that experience, I started thinking a lot about how sex is so rarely like it is in the movies and in books. And it’s certainly not like it is in porn (thank fucking god).

Things are so awkward, self-conscious, uncertain…and even sometimes scary. And then there are those amazing moments that are, indeed, like the movies:

• The moment instinct takes over, effortlessly coordinating joining bodies.
• An electric kiss or another touch that sends all partners into a paroxysm of passion.
• An orgasm that makes your eyes roll into the back of your head and your body move in ways you can’t — and don’t want to — control.

I always loved those moments, but I also started to appreciate the awkwardness, the clumsiness, the ridiculousness of it all.

There was a certain freedom to realizing that I would never be a beautiful, skinny actress and that while I didn’t want to exactly show off my flaws, I didn’t have to work so hard to hide them. Yes, if my partner held my thighs up alongside my body when I was lying on my back, my stomach was going to develop a bit of a paunch. Not pretty, but there was nothing I could do about it. Oh well.

It was also nice to let go of the feeling that everything had to be so gloriously choreographed. No, we would almost never experience the joining of our bodies without one of us awkwardly maneuvering him inside me. We’d fall over in certain positions. He’d sometimes drop me. I accidentally head-butted him once. He accidentally batter-rammed my clit on more than one occasion when he fell out of me during thrusting. New positions regularly went awry. My experimental lube concoctions often ruined our sheets.

And then there was my favorite awkward moment that happened all too often for my taste. My partner had a tendency to enjoy the old jackrabbit thrust (that’s another story for another day), and the consequence of hammering someone that hard is that it pushes a lot of air into the vagina. So when he would leave my body after sex, my vagina would make a super sexy, juicy farting sound, which made him laugh hysterically.

As you can imagine, in my thrumming state of pleasure, the last thing I wanted was for my body to be making gross sounds like that, and I especially didn’t want my lover to be laughing at me. I even started to notice when the air was getting into me during sex, and I’d immediately get annoyed, slapping him, telling him to slow down. (Some nights, it was like he was an overly-eager air compressor trying to fill up an empty tire as quickly as possible.) But it was always too late by then, and we’d get to end our hot and sexy lovemaking session with my vagina gurgling and my partner laughing.

It doesn’t get more awkward than that.

But over time, I came to love all of it. Well, maybe not love, but appreciate it.

It was such a relief not to have to try so damn hard anymore to be beautiful and sexy or to make everything look like we were working from a script.

And I actually loved it when we fell over or he dropped me and we started laughing hysterically. I found humor in the moments when he slipped out of me and accidentally stabbed tender places with his dick and I’d immediately pull back and say, “That’s enough for tonight.” (Yeah, he usually talked me out of that once the pain had subsided.) I loved getting into pseudo-arguments, like when I snapped at him to stop staring at me because I felt like my stomach looked bulgy, and he snapped back, “You know it gets me off to watch your boobs jiggle! Just let me have this!”

It was real. It was funny, messy, happy, frustrating, awkward, clumsy, and wonderful. And yes, there were endless moments in between that were so sexy, they shook me to my core. Moments that are, all these years later, still imprinted in my memory.

But the awkwardness — it’s a good thing. We need it. We need to be real with one another.

I recently read an article by the divine Anne Shark in which she put it best: “…awkwardness is inherently part of good sex. It’s part of trust-building, and it’s part of intimacy.”

That’s it, right there. I couldn’t have said it better.

I wish I had had someone to share this with me when I was a teenager before I’d had my first sexual experience. I wish I had understood that it’s okay to be clumsy, messy, ugly, awkward.

I wish someone had told me: Sex is supposed to be a mess.

And what a mess it is…

© Yael Wolfe 2019