When is the Right Time to Give Him Some Direction?

As my friend Sean says, when it comes to a guy performing oral sex, if you have to ask “what do you like,” it’s already too late and you’re asking the wrong question (Sean likes to joke, “the real question you should be asking is, ‘Can I get you a cab’?”). But I disagree, and so do my other friends. When a sexual relationship is starting out, sometimes you have to ask.

For seven nights my friend Jake just could not make her come. He would try his very best. He tried it sober. He tried it wasted. He used a finger. He used no finger. He played with her fifth base; he went nowhere near her fifth base. He did lots of inside work with his tongue. He focused solely on her clitoris.

Nothing worked. She “oooohed” and “ahhhed,” cooed and clucked, but there was no orgasm. Finally, on the eighth night, he did the unthinkable: he asked.

He asked her what she liked. He asked if he’d been doing it wrong. He asked if she came easier from clitoral stimulation or from penetration. He asked her if she liked using toys, or a vibrator. He asked is she wanted to kneel above his face, or take him in her mouth at the same time. He asked everything. But the lady just wouldn’t say.

Jake recounted this to me over cheese and wine at Beecher’s (my new favorite cheese haunt) the other night. He was distraught. He’s not an egotist, but likes to know he’s making his lady happy. Moreover, he likes this girl and is very attracted to her. The sex they are having is fun; he just can’t stand it that she’s not coming.

So he asked. And when she said nothing, he asked me. I told him I would have done the same thing. At some point, as a guy, you just have to ask. She might be shy, or pent up, or embarrassed (maybe for you); you might be wildly off the mark, close but not quite there. She may not know for sure, but if she does, she should answer. Silence, in this situation, helps no one. Instead of Jake taking swing after swing, she could be having orgasm after orgasm. Or maybe not. But if a little information is the difference between coming and coming close; I hope she musters the courage, realizes there’s nothing wrong with asserting some agency, and lets him know just what she likes.

Would you be able to tell a guy what you liked? Would you wait for him to ask? Would his asking turn you off?

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