Sex With a New Guy

To make your first hookup worth remembering, follow four simple rules.
by Bethany Heitman
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You're dating a guy, and the makeout sessions have been so hot, you’ve practically dry humped holes into each other’s jeans. With all that chemistry, the sex has to be off the hook from the start, right? Ehhh.

“Getting intimate with a new person can be clumsy,” says Chris Fariello, PhD, director of the Institute for Sex Therapy, in Philadelphia. You aren’t completely comfortable with each other yet. Plus, there’s so much at stake the first time—bad first-time sex could nip a budding relationship in the, uh, bud. Good thing these four rules will make it sooo enjoyable.

Rule 1: Don’t Jump the Gun

No doubt there’s been so much buildup to this moment that you’re tempted to skip foreplay and launch right into the part where you insert tab A into slot B. But, that’s a rookie mistake.

“The first night with someone is when you should be taking your time,” says sex educator Jamye Waxman, author of Getting Off. “Your goal should be to pay close attention to what works and what doesn’t for the other person. That way, you can please them right from the start.”

So, keep things slow and steamy from the get-go. During foreplay, any time his hands start to wander too daringly, or it seems like he’s going for the main event, grab his wrists and hold them tight. Then, give him a long, drawn-out kiss.

“Most men love it when a woman does something aggressive like this, because it helps them understand what she wants,” says Carole Altman, PhD, author of You Can Be Your Own Sex Therapist. “The back-and-forth between heavy petting and kissing will make sure things stay well-paced.”

Rule 2: Acknowledge Awkward Moments

Of course, we all want to be thought of as a goddess in the sack, so the instinct is to ignore any gawky moments and bet on the kama sutra that he will, too. But, things will go much more smoothly if you do the opposite.

Being with someone new is stressful enough because you’re worried about what he’ll think of your body and if he’ll like what you’re doing,” says Altman. “And, if you don’t accept the natural mishaps that are bound to happen, they’ll silently taint the experience.”

To rescue the mood, you need to acknowledge these slips subtly in a way that suits the kind of sex you’re having. If you’re both being playful, maintain that attitude—meaning, if he can’t seem to get your bra unhooked, don’t just sit there as he gets frustrated. Give him a smile and say, “Let me try. I know the trick with this.”

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Or, if the mood is more intense, find a way to keep that vibe intact. If you accidentally knock heads, turn your attention to that area by passionately kissing his forehead and face.

Rule 3: Say Something Nice

It’s a myth that guys are worried about only their own pleasure. In fact, most dudes have a harder time enjoying themselves when they’re unsure if their partner is having a good time. “Part of what keeps him turned on is knowing you’re feeling turned on,” says Altman.

And, since you’re new to him, he doesn’t know all your little inaudible signs that you like what he’s doing. So, it’s crucial that you tell him.

Just be sure you praise something that really does feel good, because he’ll file away whatever you say and often incorporate it into future sex sessions (and please, don’t fake any pleasure where there is none. Backtracking from that is not easy). If he’s awesome at oral, a simple “That feels so good” in a seductive voice will encourage him. Or, if your style is more cute, go with “Wow, your tongue should enter the Olympics.” By being vocal about what feels amazing, you keep the steamy momentum at present, plus help him learn what you like.

Rule 4: Hold Back From Getting Crazy Acrobatic

You may have the urge to pull out all your wild sex tricks to show him you know how to get it on, but the first time isn’t the right time.

“You don’t want to be experimenting with a complicated position or trying tricky tantric maneuvers the first night. There’s a good chance you’ll get frustrated if they don’t work due to your unfamiliarity with each other’s movements, or become so caught up in showing off your skills that you won’t be able to pause and enjoy what’s actually happening,” says ­Waxman. “Those should be saved for later, when you understand what each other needs to orgasm.”

Stick with positions that are familiar, feel awesome, and don’t require any crazy-ass acrobatics. Then, if you want to spice things up, try one little tweak, like touching yourself while he watches. This way, you won’t feel bored, says Waxman, but it is risk-free and lets him know there’s a whole lot more where that came from in the future.

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