Ask Jack and Jill: Expectations, New Terrain, and PE Prevention (18+)

Twice a month, two local sex and relationship writers take your anonymous questions

Ask Jack

“Hey Jack. I’m sleeping with a great guy … who can’t seem to last more than a minute, two tops. Without him knowing (I don’t want to complain about it and make him conscious of it) I’ve tried buying those ‘desensitizing’ condoms. They did jack, Jack. As someone who ejaculates, I am wondering if you have tips for me to make a guy last a little longer? He’s a keeper, see.– Sue

Hi Sue.

If you find those kinds of products aren’t working for him, a more natural technique, that can make sex a little steamier if you do it right, is to find out how long you can go (thrusting) before he ejaculates, and never thrust that long. It’s the constant, uninterrupted stimulation that makes him come, so, interrupt the stimulation with pauses! If you’re saying he comes in one minute, then, get on top, thrust for 30 seconds, then stop the thrusting action of the sex for a bit and just lean down and make out for ten seconds or so, distracting from the fact you’ve stopped thrusting. If you have sex for thirty seconds, stop for ten seconds, and repeat, giving him a break in stimulation before he’s at that point of no return, he’ll last a lot longer. He’ll also have a stronger, more satisfying orgasm. Ditch the notion that “sex” is merely fast-paced penetration, and start finding ways where he isn’t being stimulated the whole time.

Ask Jill

“I have a boy who, 2-3 times a month likes to go in for some ‘titsex.’ It’s the weirdest thing. I don’t know what to do, I just lie there feeling really awkward, hands by my side, waiting it out. Is there something I’m supposed to do to make ‘titsex’ hotter? –  JustLiesThere

Hey JustLiesThere,

Get involved! Don’t just lay there and wait it out. That sounds horrible! You should enjoy this act as well if you’re participating in it. Use your hands to cup your breasts and squeeze them together or you can try rubbing a little lube between your breasts to add a new sensation for him. You can also try having him lie on the bed and you can lay over him and do the work! If his penis is long enough, you can also incorporate a little oral action as well. Yum! If you really don’t enjoy this act, then don’t do it just to please him. Let him know it’s just not your thing. However, if you’re cool with it and you just want to get in on the action, try one of my tips! Sex is supposed to be fun, remember?

“Jill, I’m getting back into the dating game after a 4 year relationship. I’m nervous about not knowing how many dates people go on before sex. Am I being awkward to say ‘okay, good night,” on dates 4 or 5 with no sex? Or Is that too soon? I really don’t know what dudes are expecting. When do you know it’s time to have sex?” – ANON

Hi ANON,

There is no set number of dates or a general time line to follow. You’ll just know.

I’ve slept with a partner on the first date and I’ve also waited five months before I slept with a guy I was dating. There was also a time when I was in a relationship with a guy for an entire year and we didn’t have sex at all.  Just do whatever feels right for you.  Don’t be nervous. Enjoy it! Have fun exploring new people and discovering what works for this new, single you.

P.S. Also, don’t date dudes who are “expecting” sex. Date dudes who are lovely and fun and sexy and who let sex happen naturally on its own, without any expectation or assumptions. Those are the best kind of guys.

“Jack” and “Jill” are monikers for two local sex & relationship experts, and they’re here to honestly answer your bottled-up questions, every second Tuesday. Use the completely anonymous form below to submit a question

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