I am a happy, well-adjusted bisexual woman in my mid-twenties. Since I began dating in my early teens, I’ve been in a mostly steady stream of long-term, monogamous relationships with men. I’ve always been attracted to women too, but my experience with the fairer sex is limited to a few random (mostly drunken) sexual encounters — no actual dating. My amazing boyfriend of three years told me early on that he would not consider it cheating if I wanted to see women too. I recently decided to take him up on that, and with his blessing, I set up an account on a dating website. Overall, this has been a good experience. I’ve even developed a great connection with a beautiful girl I’ll call “Sarah,” who is also new to dating women. We’ve been on several great dates and exchanges lots of flirty texts and emails. I know she is in to me. However, we’ve only kissed a few times, and I think we would both like to take things further, but neither of us is quite sure how. As a pretty girl, I’ve never had to make the first move before. The man has always taken the lead (at least in the beginning of a relationship). Best I can tell, the same is true for “Sarah.”
So here’s my question for you guys: how the hell do you do it?! I’m not asking for step-by-step instructions for seducing a lady (I’ve got a pretty good idea what I’m doing, thanks!), but I would love some advice on how to get over this weird shyness and just take the plunge. This is something most guys figure out how to do in high school, and here I am, an adult, too intimidated to lean in for a kiss until she’s walked me to my car! Any tips to help me unleash my inner Casanova? — The Tension is Killing Me!
MATT: Let me get this straight (pun intended), you spent 300 words talking about the understanding boyfriend, the drunken experimentation, and going online to source out some lady bits; you carefully note that you’re already versed in seduction (hilarious detail) then—drum roll, please— you finally get around to asking your big question: how to get over this “weird shyness”?
Let’s skip the self-esteem, sexual identity, open communication (with “Sarah”), fidelity chat we could have and instead address what you’re really asking for: Permission. Permission to get down and dirty with your gal pal? GRANTED. Permission to, quite possibly, not be very “good” at it? GRANTED. Permission to totally dig it? GRANTED, baby. If you’re certain she’s down for some lady fun, find a time and place that’s mutually comfy and safe, take off your pants and go exploring…You’ve come this far, right?
So? Actual tips? Okay, fine: Take plenty of lotion along on your all-girl picnic, hand-warmers (essential), an open mind, a squeaky-clean body (without a ton of perfume, thanks), a list of questions, lots of time, some candles, and a sense of humor. Go ahead and bring Sade for the soundtrack; she works for almost any occasion. Oh! And don’t be afraid to go basic: “Truth or Dare” and “I never” are both excellent games, if you ask me.
JAREK:In high school, we all had raging boners 18 hours of any day, so we *had* to do something. As such, we just went for it. We got shot down a lot, but sometimes we didn’t. It only takes riding a bike so many times before you no longer worry about falling off. That’s the hump you need to get over. The biggest fear in making a move is thinking that the other person is “better” at this stuff than you and that you are going to end up looking like an inexperienced idiot. You both appear to have the same experience with this sort of thing, so she is likely just as nervous as you are.
Knowing that, the most important thing is for you both to feel comfortable in your situation. Go back to the basics of feeling comfortable when you’re exploring intimacy – lights on or lights off, bed room or living room, music or TV in the background. Have a drink while you two get comfortable in front of each other, just take the edge off. It’s not called liquid courage for nothing. Once you’re there, communicate. “Is this okay?” “Do you want to keep going?” If you’re engaging yourself with the other person, she isn’t going to feel rushed or violated or uncomfortable, and neither will you. You can progressively move your way up to exploring new things, and you’ll be doing it together.
JMagic: I’m going to let you in on a little secret: guys never figure “it” out. If by chance some guy did there’d be this mythical 10-page-or-less book containing that info that would sell out all over the place and the only way to get your hands on it would be to take out a second mortgage and know some secret handshake … maybe I just haven’t learned the handshake yet.
But seriously, every guy, including your current boyfriend reaches a stage in the relationship where he wants to take it further but the awkward nervousness and fear of rejection make it difficult to do so. Now, the ‘Casanovas’ of the world have just learned to better contain said awkwardness and use it to their advantage. Others simply fumble their way around and find out, or are still searching many years after high school.
The best way to do it is … to do it. Plain and simple. Part of the joy of a new relationship is being in the exact same spot you’re in right now. You can both feel it. You know you want it. But the so-called rational part of you wants you to keep waiting until the obvious ‘open for business’ sign turns on. Not gonna happen. Especially since you haven’t been in this spot before. So, tastefully, dive right in and make your move. Sure, you might get rejected, but who cares? From the way you describe your relationship with your boyfriend and woman you’re dating… you’re having your cake and eating it too. Enjoy it and try not to put too much thought into it.
DENNIS: Short of directing you to the world of pick-up artists, my suggestion entails two basic components: 1) body language and 2) baby steps. Pay attention to how she responds when you’re being intimate. Is she pulling away? (Bad sign.) Is she leaning in? (Good sign.) Combine that with what I call baby steps: Don’t stick your hand straight down her pants right away. Instead, move your hands over her body and see how she responds. Start with the “safe areas”… hands, arms, upper back, you know, places you’d naturally have your hands as you’re kissing her. Then, move them to slightly more risque areas… her hips, legs, small of her back, neck. Again, notice how she responds. If she moves toward you, or even reciprocates, then keep progressing. If not, slow down, hot shot. Once you feel that she’s sufficiently comfortable with you touching her (believe me, you’ll know), then you can move on to the, ahem, private parts.
And wow, that just got really graphic, didn’t it? I think I’ll let you finish the seduction from here, mostly so I can go take a cold shower now.
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