For the record, I feel the internet has failed society if earnest young men have to seek advice from me. That I seem like a relatively reasonable source of input is sad as hell.
But onward…
- Cultivate a relationship where she knows that you’re interested in how your actions are received. Seriously man, a field full of interpersonal landmines can be side-stepped by simply giving a shit about the impact of your behavior. Girls are weird; they like it when you notice their lives are real.
- Do not, under any circumstances, Make A Plan. Sex is a call-and-response improvisation… you’re not there to hit your marks and speak your lines. If you have a plan, you’re going to be thinking about getting to the next step, when you should be thinking about how her eyes look at that moment, if she smiled when you took her hand, if she’s leaning into you when she laughs, and so on. Just be present… girls spend a lot of time thinking about boys, and they find it inordinately exciting when they can see a boy thinking about them, too.
- Be sure you’ve done your prep work. What is she into? If you don’t know, find out; drag it out of her like a demon on the losing end of an exorcism. Or… on second thought, that’s more my style… you should probably just encourage her to express herself as much as she’s comfortable, and make damned sure she never regrets confiding in you. Whatever you do, be very confident that you’re not going to inadvertently blaze a trail for her… that first time is for making her feel discovered, not rocking her world.
- Don’t put yourself on a clock. The first time might be over quick, or it might be underwhelming, which is pretty reasonable when you think about all the assumptions and insecurities you’ve both overcome to reach the point where your dick’s been inside her. But there’s a cheat code to solve this problem: left-right-left-right-A-B-START doing that shit again, my friend. You’re young and can fuck all night long… so fuck all night long. Fuck ‘til one of you is bored or exhausted. In short: rather than initiate sex, you should initiate an evening.
- Take a shower first, ya filthy animal.
Good luck, and be nice to her. Don’t make me look bad.