First-Time Sex with New Partner: A Guy’s Perspective

Doug Dalton is a good friend and guest blogger who happens to be in “new relationship phase,” so of course, we wanted to get the juicy (and awkward) details from him on how it’s going. Doug eats, drinks, and dates in San Francisco, though is most successful with the drinking.

The background: you have successfully woo’d her. A few nights out for cocktails, a nice dinner or two, and she likes you. Against all odds, you have convinced her that you are not a total scumbag, and that you are sexually attractive or, at least, sexually acceptable (either will do). You have followed the base path taught to you so many years ago, which, while funny, is actually the pattern you follow every time: kissing (french), boob touching, then vagina, and finally sex. This base path is the Esperanto of making out, except it is actually accepted by most.

The setting: Now back at your place (or hers), you are going to do it, for the first time. How do you know when it’s that time? Well…that’s a different post. For the purposes of this, we will assume you are pretty, totally, almost completely positive sex is going to happen.

The challenge: Most every man takes for granted that he is going to cum during sex, and I think most women expect that, too. Beyond this straight-forward biological reality, you have a goal: pleasing her. Pleasing her, though, is actually a complex union of goals that include giving physical pleasure, boosting your ego, exciting her, and making things interesting, all while not horrifying her. For those of you who believe in the cliché that men have a one-track mind, I assure you there is a lot more going on up there than you think.

The analysis:  Since your own pleasure, to some degree, is a given, pleasing her becomes a complicated and even distracting pressure. There are a number of reasons for this, many of them selfish, but all are part of what’s going on in your head during the sexual encounter. Here are some of the reasons pleasing a woman is such a challenge:

• You want her to enjoy it. The first reason is simple – you want her to enjoy it. If she doesn’t like this, then you don’t get to ride again, er, unless you are either rich or one hell of a charismatic motherf*cker. Thus, pleasing her is important and openly intimidating.

• You feel inadequate. Thoughts of inadequacy, while not rushing to the front of your brain, do linger in the background like the guy no one exactly knows at the party who keeps stealing beers from the keg. It might be about size, experience, or endurance. Questions run through your head like, “What was the last guy doing? Was he more fun, more open, more forthcoming physically?” Knowing that you’re probably an average lover and not too much more doesn’t help, even if it does put you in the middle.

• You want to be an amazing lover. Admittedly, this is pure ego, but as a man the concept of satiating a woman to the point of either fainting, gasping for air, or paralytic nirvana is a goal worth attaining, or at least dreaming of attaining. You want her (when she finally comes to) to announce to the world (starting with her friends) exactly what a sexual beast you are.

• You want to stand out. Beyond just pleasing her, you want do something more. You want to give her a little something to separate yourself from the others, as well as to excite yourself.  It could be anything, a solid ass squeeze, rough on the boob grab, nibbling, some sort of hip twist… who knows. But we all do something that, while we wouldn’t call it “patented,” we can recognize as falling onto the “extras” menu. It’s off the base path and hopefully therefore exciting to her and adventurous for you.

• You don’t want to be too “deviant” the first time, though. Is a thumb in the butt too much? Fine, a jaunt off the third base line is great, but might it horrify her? While you want to please her and be exciting, you don’t want to horrify her. There are some things you don’t want to ask; you would rather just do and roll the dice. Maybe she is a gambler, maybe not; finding out can be fun and a bit of mischief.

In the end, when you are both lying on your backs, realizing how late it is and that you are going to have a hangover in the morning, you can look back and reflect. Reflect on an evening that was just like you thought and nothing like you thought. You realize you probably didn’t come close to pleasing her, and the thing you thought was going to be cool and exciting turned out to be blunder-full and awkward. Strangely, you are pretty sure she will have sex with you again. Hopefully someone will write a post “Girl’s Perspective on having sex with a new guy for the SECOND time” because that is the real mystery.