The new kid | Updated 3/6/2013

Tips for pleasing an older woman.

Q: I’m a 20-year-old guy who is about to have a girlfriend for the first time in his life, and I’m clueless about how to please her. I’ve always been too obsessed with straight A’s to even look at girls. So I dropped some extracurriculars and got a part-time job at a bar, thinking it would be a good place to meet girls. Well, I met the greatest girl who works there. She is nine years older than me but we get along great. We go out on dates and have gone back to her apartment a few times to mess around, but I can’t tell if she is enjoying it. I’m not a virgin, but my experience is limited to a girl last year who attacked me (in the good way) a couple of times and then acted like it never happened. I know I should know more about women by now, and I don’t want to disappoint this girl. What are some things I can do that she will for sure enjoy? What signs do I look for to know when she is ready for sex?


A: Step one: Have a little confidence in yourself. You were smart enough to realize what was missing from your life, so you went out and found it. That deserves a pat on the back, if not a tongue down the throat. You even found a great girl whom you’re intent on making happy, and I have no doubt that you will achieve that. Take that academic can-do attitude and apply it to your new relationship. Everyone is attracted to confident people; we inherently like to be around those with a positive disposition. You might be a little intimidated by her age, but I assure you that it rarely makes a difference. Don’t assume she’s got a mile-long list of past lovers and knows everything there is to know about sex. Twenty-nine may seem like a wise old age to you, but my guess is that she’s still learning new things about herself and what turns her on. Likewise, you’re not a late bloomer just because you haven’t bedded a bunch of girls by age 20.

Step two: Pay attention. If you can learn C++, you can certainly pick up on the signals that indicate she is enjoying herself. Look at her face, for starters. If she’s smiling or smirking with her eyes closed (or better yet has them focused on you), then keep doing what you’re doing. If she’s sporting a mean grimace and looking anxiously at the ceiling, stop whatever you’re doing immediately. Reset the mood by offering her a drink and moving from the sofa to the floor for a backrub. When someone is touching us in a pleasurable way, we tend to want to reciprocate. If you notice her running her fingers through your hair and rubbing your neck and shoulders while you’re tongue-swirling around her nipples, then you’re doing a great job. I can’t tell you exactly what turns her on, but you’ll figure it out quickly just by watching for signs and listening to her. She can tell you what she likes, so make sure you ask her. I’ve said it before: If you don’t communicate in bed, you’ll get exactly what you asked for.

Finally, speaking for all the gals out there who prefer to date younger guys, know that we sometimes get insecure, too. We can be sensitive about the age gap, because the double standard unfortunately still exists. Our culture still regards an older woman-younger man relationship as an oddity, yet we’re supposed to believe Jennifer Lawrence (22) would actually have the hots for Bradley Cooper (38). There are bound to be some blank stares when she quotes “Vicky Cristina Barcelona” or you reference an episode of “Avatar: The Last Airbender,” but if you have fun together and the sex is getting good, something as small as your age difference shouldn’t even be acknowledged.

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