For the last few months, I’ve been hanging out online with a new crush counting down the days till we can meet in person. We’ve both had our first and second shots. Now we’re just waiting the extra two weeks. And then—FIRST DATE! I’m so excited I can’t stand it! The only problem is that I’ve never had sex with another woman before. Even though I’ve always known I’m pan, I’ve just kept getting into LTRs with dudes and other humans with penises. My new crush will be my first gal pal. We’ve talked (and talked and talked) about what we like, don’t like, and want to try. But for real—I’m nervous. I’ve seen movies and read some stuff. I know I’m a good kisser. And I pay a lot of attention to detail. I’m a pleaser, and it’s important that my partners have a good time. I don’t know though. I’m intimidated when I think of learning a whole new body part! I know my bits sure can be picky about how they’re handled. Can you tell me help me out? Just tell me some real basics to get me started? Any advice is sure to help!

Getting Some Real COVID Relief

Dear Relief,

Congratulations on your new crush, and on getting vaccinated! Way to stay safe! It’s been a hard year, but I feel like we’re finally seeing the light at the end of the tunnel.

First up, make sure you and your gal pal are protected. Use barriers for everything to reduce the risk of STIs. Remember that chlamydia, gonorrhea, HPV, herpes (1 and 2), and others can all be transmitted orally and by skin-to-skin contact. Gloves and dental dams are going to be your friends!

While it’s daunting to try new things, you’ve already done a lot of learning and preparation during this period of social distancing. See, our biggest sex organ is our brain. It sounds like the two of you have already been using your brains for the last few months. Getting to know each other and talking about your sexual (and other!) interests is what has gotten you excited in the first place. You already know a lot about how to please her because you’ve been communicating. That’s going to get you a long ways in this exploration.

Next, keep in mind that your crush is more than just her bits. She’s a whole human, and there are lots of places on the body to stimulate. Put your good kissing skills to use on her neck maybe, or her shoulders. The insides of the elbows and backs of the knees are also very sensitive. Check in with her as you’re going, asking her what she likes. It sounds like you’re planning to have sex on this date, which is awesome. Just remember that in the moment, one or both of you may decide that you’d like to wait until a second or third date for that. That’s awesome too, because it gives both of you a chance to be really comfortable with the decision.

Whether it’s on the first date or at another time, here’s some basic information about pleasing a vulva or vagina.

Let’s start by discussing orgasms for people with vaginas. Many of us cannot orgasm without clitoral stimulation, either alone or in combo with other play. This is really typical. Also, there is no one type of orgasm that is superior to the other types. Many people feel like they “should” be able to come in specific ways, giving more weight or importance to one type of orgasm over another. A g-spot O isn’t better or worse than a clitoral O. They’re all orgasms, and that’s pretty great. You will find things that will work best for her, and that’s the important thing.

When you’re stimulating a vulva or vagina, utilize variation. Don’t do the exact same thing for too long. Just like with kissing, massage, and other types of touch, making contact with the same place on the body for an extended period can be overstimulating or even annoying. You can play with something warm or cool for variety, or try a lube that gets warm or maybe something that tastes good. Involving a few different senses in the process can be a lot of fun!

When we settle in for sexy times, we often make a move directly for the clitoris or the vagina. I think it’s a good idea to sort of send a greeting before barging in. By that, I mean spend a little time with the vulva (the whole collection of external parts including outer and inner labia and the pubic mound). You can cup your hand over it and apply gentle pressure for a few moments to introduce yourself to her bits. From there, maybe run your fingertips through her pubic hair if she has any, or just run them over her outer labia if she doesn’t. If you’re both enjoying yourselves, you can try touching her vulva in other ways (tugging a little on the labia, or spreading them to get a good look at her).

Moving on to the clitoris is a logical next step for many folks. The clitoris usually likes motion more than stillness. And it likes that motion to be pretty rapid. You can touch her clitoris with your fingers (do you have gloves on?) or with your mouth (got that dental dam handy?). Maybe she has her favorite vibrator nearby and the two of you can experiment with that. Lube will allow your hand or a vibrator to move more fluidly without friction. As much as she’s comfortable, let her guide you. Most people have a good sense of what their bodies like. If you want her to have pleasure, following her lead is a good idea.

For many folks (though certainly not all), vaginal penetration requires a different level of intimacy and trust than external stimulation. And this can apply to both the giver and the receiver! Going inside someone’s body is a big responsibility! Checking in before moving onto penetration is a must. When both of you are ready though, penetration can be lovely/hot/amazing/sensual. The most sensitive portion of the vagina is the first inch to inch and a half. If you’re using your hand to penetrate a partner, you’ll want to be wearing a glove. If you’re using a dildo or vibrator, you can roll a condom onto it. And definitely use some more lube! Some people like slow thrusting and others prefer a rapid motion more like pounding. Tune in to how she’s moving and match her motions. And don’t forget! You can always just ask if you’re not sure!

These tips are just to get you started. When the two of you are together, you’ll hopefully be able to discuss what’s working (and what’s not), and make fun and appropriate adjustments together. While the first time with a new partner is definitely special, repeat encounters will give you both the opportunity to really learn how to give and receive pleasure as a couple.

Curious about cunnilingus? Anxious about anal? Do you have questions about queefs or problems with your prostate? Lucky Tomaszek is the education coordinator at The Tool Shed: An Erotic Boutique, Milwaukee’s only mission-driven, education-focused sex toy store. Send her an email at [email protected] and she’ll get back to you with an answer.

About The Author

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Lucky Tomaszek, LM, CPM, is the education coordinator at The Tool Shed: An Erotic Boutique, Milwaukee's only mission-driven, education-focused sex toy store. Most mornings you can find her balancing her cat and her keyboard in her lap, working to make the world a smarter, safer place for people of all genders and orientations.