Babybutch wrote:

My girlfriend totally knows how to get me off, but I’m nervous that I’m not doing enough for her sexually. We’re very honest with each other, but I worry that she’s not saying anything because she’s afraid of hurting my feelings. What kind of sexual activities would you recommend for the relative novice? What did you “start” with when you were just beginning your sex life with women? I think my biggest problem is (lack of) confidence.

I think you’re probably right, that more than anything it is a lack of confidence. My best advice for building confidence is: a) come up with a small script you can say when you get nervous, where she will reassure you in a way that makes you feel more confident and builds you up (this also might involve a post-fucking script with lots of praise over what you did); b) ask her what she likes, let her direct you until you get it right; c) fake it till you make it—not with the moves, but with the confidence. Just pretending you have confidence will get you pretty far, since usually confidence is actually about a mental state rather than any physical action that you do (or don’t do).

This also kind of depends on how toppy or switchy you are—it’s harder to fake topping, I think, and harder to let her direct you if you’re also trying to build dominance too. But you said she knows how to get you off, so perhaps that isn’t a factor with you two.

You also wrote: “We’re very honest with each other, but I worry …” See if you can work on that. You can flat out tell her, “Hey, I know you said it’s okay, but I have the impression for some reason that maybe you just don’t want to hurt my feelings. Now if you tell me that I’m wrong and just worrying too much, I will believe you, but I also want you to know that I can take it, and I’m interested in getting better at fucking you, so I hope you’ll help me do that.”

And if she tells you that it’s okay, then you can choose to believe her. (She can also choose to change her mind later, and hopefully you won’t take that as an affront, or that she was lying—just accept that sometimes feelings about things change, and that she’s being as honest as she can be right now.)

Another issue at play here might be the difference between how many times she wants to touch you vs how many times she wants to be touched (or how many times you want to be touched vs how many times you want to do the touching). Conventional lesbian wisdom says I-do-you-you-do-me, but that doesn’t necessarily jive with everybody. I, for example, am a top bordering on stone, so I don’t want to be touched, barely ever. Maybe 1 time out of 20. But perhaps you are a five-out-of-ten person, or an eight-out-of-ten person. It sounds like her desires—to be the one who mostly touches you—is driving your sex life right now, but that can (and should) be co-created by the couple to figure out what’s best for both of you. Maybe you want to do more of the touching, but your confidence is holding you back? Maybe she’s not so good at asking for what she wants, or giving you permission to just explore and play? Maybe you are both too goal-oriented here—just because you don’t know how to get her off in two seconds, like perhaps she does to you, doesn’t mean it isn’t still a good idea to touch her, kiss her all over, make her feel good.

And yes, it’s possible that she’s overcompensating because of your nerves, being more of the actor than the receiver because you aren’t stepping up. So if you want to step up, do it. I would TALK to her about it—out of the bedroom, on a random afternoon where you’ve had a lovely morning together and you are both feeling loose and open. Say, “Hey, I know I haven’t been stepping up in the bedroom much, but that’s because I’ve been kind of nervous, but I’d really like to work on that. Can we talk about ways we can play so I can try to build my skills?”

And, speaking of skills. You asked for advice on activities for a sexual novice. Ultimately, it all depends on what you like, and what she likes. There are activities that I think are kind of basic and beginner that other people think are really advanced and edgy, and vice versa. Like cunnilingus—going down on a girl—that is something that I do not do with a new lover, mostly because it’s so intimate (and the whole fluid-bonding thing, since I much prefer it without a dam). It takes time to build up to, for me. But then again I can top someone and be dominant on a first date, spanking or using restraints or pulling hair, which some people would think is a much more advanced thing to do.

But, generally? I think to be a good lover, you should be good at these things: 1) kissing, 2) finger fucking, 3) going down, 4) toys, whichever toys you might be in to, be they vibrators or strap-ons or bondage equipment, 5) quickies.

Of course, there’s plenty more things to get good at—anal, bondage, squirting (if either of you tends to do that—or if you don’t, you can experiment and see if you can make yourselves do it), percussion play, penetration, dirty talk, role play … but generally I think those take longer to learn and experiment with, and if you get those others down, you’ll be golden.

Kissing: check out Violet Blue‘s book Seal it With A Kiss (or her ebook, How To Kiss) if you doubt your abilities. Go slow, make it luscious, make it last, don’t use too much teeth or tongue or saliva. You probably know the basics.

Finger fucking: Practice on yourself. I assume you’re good at getting yourself off already. Watch her masturbate so you can see what she does to turn herself on: does she always have her fingers on her clit, and never go inside? Does she start with a lot of fingers in her cunt and only put her fingers on her clit at the very last second? Does she use tons of force, or very light strokes? Are the strokes long and circling, or slow and jerky? Watch closely. Take notes. Try to duplicate it. Ask her for help—”There?” “No, lower, lower—YES. Harder. Left-right instead of up-down. Like that. Don’t stop!” (And then, whenever a lover says don’t stop, for goddess’ sake, DON’T STOP.)

Going down: Check out Going Down: How to Give Her Mind-Blowing Oral Sex which has some excellent tips, or Violet Blue’s Ultimate Guide. I have a whole class on this, so I have more things to say than I will go into here.

Toys: Consider adding a vibrator to the mix if you are worried that your skills aren’t getting her off. Have her hold it and use it while you fuck her, while you kiss, while you talk dirty in her ear, while your fingers are inside of her. I am not huge on vibrators myself, but I do love the Hitachi, and there are a lot of really beautiful high-quality high-class vibes out there these days. Experiment! Ask your favorite sex toy store for advice, I’m sure they can help. I just noticed that Babeland has 20% off of Jimmyjane vibrators this month—that might be worth looking into, those are beautiful (and expensive).

Quickies: For lots of reasons, this is a great thing to work on, to be able to do as a couple. For one, it says to her, “I can’t wait, I have to have you RIGHT NOW, I don’t care if we only have ten minutes,” which is flattering and good for the bond between you. But also, it is good practice for getting her (or your) arousal up to the point where you can come quickly. It takes skill and practice and enthusiasm! If it was me, trying to get better at something like quickies, I would lay it out directly: “Hey, I really want us to be able to fuck quickly. Are you game to try that? Say, every day this week we’ll try to just work in a really quick fuck somewhere other than the bed (or maybe in the bed, too, if that works). Are you up for that?” And see how she feels about that kind of thing. Maybe daily is too much, but maybe it could be daily over a three-day weekend? Or every other day? I like setting specific guidelines or goals around things like that, because then if we both consent to it, it makes it easier to follow through with. But—your milage may vary, do what feels good for you.

Last but not least, you asked how I got started, when I started fucking women. I went to a women’s erotic workshop, one of those that I have been pimping out lately because I’m now coordinating the workshops, before I’d ever slept with a girl. That most certainly helped.

But, thought I had (quite a bit of) experience fucking guys, I didn’t have much confidence and I wasn’t sure what I was doing. The first girl I slept with hadn’t actually slept with a girl ever either, so in that we kind of figured it out together. I remember very vividly how nervous I was, how we both knew what was coming, but neither were sure how to start or, once we’d started, how to proceed. She actually said, “I don’t know what to do,” which, for me, was the permission slip I needed to just go for it, to follow my instincts and to stop holding back what I wanted to do to her, how I wanted to touch her. When she admitted she didn’t know, well, then, there wasn’t much I could do that would be wrong, would there?

We only dated for about a month and slept together only about three times, partially because my mom was in town for a week and partially because I got my tongue pierced the day after our first date. Um, whoops.

Well—that was longer than I intended, but I hope that is helpful!

And now, what about you all out there? What’s your advice for this babybutch? How do you build confidence in the beginning? What were your early experiences fucking women like?