One of my favorite columns on my sex spreadsheet is the one listing how many times I’ve had sex with each person noted therein. I updated it today and noticed that I’ve had sex with Matt 504 times in the 1,079 days we have known each other. And that’s not even counting phone sex. Yeesh.
I’ve known for a long time that sex is better for me when I’m having it with someone I’ve already fucked many times, and this is borne out in scientific studies that find women are less orgasmic during casual sex than they are in relationships. While a “relationship” in this context can be whatever you want it to be – a long-term friendship-with-benefits, an ex you’re still pals with and occasionally fuck, or just a regular ol’ romantic partner – these ongoing dynamics are far more conducive to good sex for me (and many others) than anything more casual or fleeting.
I’ve gotten in trouble on Twitter before for sharing this take, because it was interpreted as slut-shaming, or as a judgment on the merits of casual sex. To be clear, I wish I liked casual sex more, and I both respect and envy people who are able to have a great time rolling around in bed with a near-stranger who they know they’ll never see again. There is nothing wrong with casual sex itself as a concept – the execution is where it usually falls flat for me.
There is nothing to prevent you from, for example, asking a casual partner several questions about how they like their genitals touched before diving in, or inviting a hookup to bring their favorite sex toy along and show you how to use it on them, or staying up all night fucking your date again and again until you’ve gotten good at it. The trouble is that most people I’ve casually hooked up with have not done these things – and, to be fair, I usually haven’t, either. Maybe things would be different if I predominantly hooked up with other people in the “sex-positive queer kinky nerd” community, but most of my one-off sexual experiences have been with random vanilla straight cis guys from Tinder and OkCupid. Most of them are not all that interested in mid-bang check-ins or clitoral mastery.