Yeah, I like my rock’n’roll and I can get dirty with the best of them, but I love my George Michael, and always have. Heck, my first masturbation was inspired by George more than two decades ago.
I felt like I was 13 again last week as I waited for the concert to begin, and was over the moon when, at long last, a still-unseen George began belting out one of his lesser-known tracks, “Waiting”, from behind the stage.

All those insecurities
That have held me down for so long
I can’t say I’ve found a cure for these
But at least I know them
So they’re not so strong

Those lyrics got me through much of my teens and taught me at a very early age something I think I’m struggling to remember until I die: Insecurities never really go away, we just learn about ourselves and know how to out-think and overpower them, like George did.
God knows my insecurities have never taken leave of me, and sometimes I doubt that they ever will. Yesterday, shopping at Value Village, in their shitty lighting, surrounded by a lousy selection, and with my heat-wave water-retention at full-power, much of those insecurities that have plagued me throughout my life were brought home.
Worse, now that I’m older and wiser, I started being mad that I’d allowed myself to be so affected by old insecurities, and had so stupidly done what I knew I shouldn’t (shopping when I wasn’t feeling sexy anyhow) so there I was, both feeling all my old insecurities, and disliking myself for feeling them.
Welcome to Humanity 101, I guess. It’s how we roll.
Insecurities get in our way in life, especially during sex. How do we get past them? Like you do most impassable things: By pushing your way through, no matter what it takes. Especially when it comes to getting past your insecurities during sex.
Take me, for instance. Always being overweight in my life, about the last thing I ever wanted was to have sex on top. I always figured that it’d be horrific having to be consciously aware of my jiggling during sex. Then I had the concern of weighing too much on top of a lover. All those things that make sense to feel, but really, really get in the way of enjoying yourself, you know?
Doesn’t matter that guys have fantasies about “jiggling” or that the weight means more pressure on his penis and in a usually-good kind of way, that’s just too much logic for a girl in the throes of her insecurities, isn’t it?
Three or four years ago, I finally got past that and started not just going through the motions on top, but really trying to get out of my head and get into what it was feeling like, instead. Surprisingly, it actually felt pretty hot. Then I started to enjoy myself. In fact, I discovered this neat little trick where I can almost “ratchet” my hips through a few positions, much to the delight of the fellow who first experienced it. That LOOK he gave me as he gasped. Who knew?
When I get to thinking of all the stupid things I’m scared of looking like or feeling like as I’m on top of a guy, the thing that stops it all is that expression that first guy had, when I knew I’d finally mastered the on-top experience.
All those years of resisting being on top, all those years of thinking from my insecurities first rather than the feeling being on top created, and suddenly I learned, with one gasp and exclamation from one guy, that if I’d just gotten past that bullshit sooner, I could’ve had that empowering feeling of a guy melting beneath me all those years earlier.
Like I said, welcome to humanity 101, eh?
I guess that’s the trouble with sex sometimes. We’re so afraid of looking like an ass or feeling like a moron, that we don’t allow ourselves to submit fully to the moment. That’s why we have bad sex, or underwhelming orgasms, or no orgasms at all. Because we get to thinking too much, and not doing.
That’s one of the reasons I’m loathe to do these step-by-step instructions people will often ask for in regards to different sex tips. I have this fear that, somewhere some woman’s going down on her man, thinking, “Now, what did Steff say to do after sucking the base of his shaft? Oh, DAMN, I can’t remember!” as if she’s baking a cake or something and just forgot an ingredient. Improvise!
Sex is hard enough without having to get all intellectual about it. Getting past our fears is hard enough, too.
So what do you do? You do what you’re scared to do. You do what you’re fearful of feeling like a loser during. You just try. You do it anyways. You hang your judgments and fears up in the closet, and you get busy, darlin’. Then, when it’s over, you look at the post-orgasmic mess of a lover lying crumpled beside you and you think “Yeah, that’s all me, baby.”
Because it is. When you ignore your insecurities, dismiss them for what they are (humans feeling human), and fully immerse yourself in the experience, you might find yourself pretty surprised with who you were able to be for a few short minutes, and just how much your lover became a fan too.
Or maybe it’s not about the orgasm. Maybe, for once, it’s just about knowing you didn’t get in your own way, and maybe that’s enough to make next time a little easier.
Because that’s about the only way we really get past these things.
PS: The GM concert, in the end, was awesome. Of course it was. He’s a consummate pro. I posted a review on my other blog.