8 Tips For Women Sleeping With Women For The First Time

Listen up, ladies!

sleeping with women
Photo by Brooke Cagle via Unsplash

No, but really — how does a person have better sex or a better relationship? The Fresh Toast has enlisted Rachel Krantz, a sex writer and proud canna-enthusiast, to help readers out with some answers as its sex columnist. No question is off limits, and all questions will remain anonymous. Please send your sex and relationship inquiries to freshlove@thefreshtoast.com. Now, onto this week’s topic: tips for women sleeping with women for the first time.

Q: Hi! I’m a 25-year-old woman who’s only slept with men. I’ve always liked women, it’s just never happened for me. Now that I’m single again, I decided to put on my dating profile that I like both men and women. I set up a date with one woman, and I think it went well! I was upfront about being a girl-virgin, but she still seems interested. Now I’m just wondering … how the do I actually sleep with a woman without sucking? I’m so intimidated! I know as a woman how picky I can be, and how much people can suck at oral sometimes. How do I go in with great game?

A: I love this question. Up until a few months ago, I was just like you! I’m happy to say I’m on the other side now, and that much of the advice my queer female friends gave me in the years leading up to finally sleeping with a woman proved true and helpful. Now, I also have some advice of my own to dish out. Here are eight tips for women sleeping with women for the first time.

Study Girl Sex 101

This was my first step, and man, was it a good one. Allison Moon’s Girl Sex 101 is by far the best sex guide I’ve ever read. I learned all kinds of techniques in there, and plan to continue revisiting it often. She gives excellent advice on how to please a woman that you can also apply to yourself (and show any future partner). My favorite trick I picked up from her guide? Always warm a pussy up before you touch the clit directly — literally. She suggest cupping your whole palm over the vagina and gently squeezing to get the blood flowing — feels great, and works every time.

Make Sure To Masturbate Digitally On Your Own

While I’m a big fan of vibrators, it’s true that one of the most important ways to understand how to touch a woman is to know how to touch yourself first. Spend some time thinking about what you like, stroke-wise. While it won’t always be the same for another woman, the way you like to touch yourself is certainly a good starting point for learning how to touch someone else.

Be Upfront About Your Lack Of Experience


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In your question, you said you’ve already been upfront with your potential sexual partner that you’ve never slept with a woman. Good for you! While it can me tempting not to reveal your novice status (trust me, I know), lying or omitting information never leads to good sex in the long-run. The person you’re with deserves to know — and putting it out there, preferably before you’re in bed, will help take some of the pressure off of you.

Trust That You Know More Than You Think You Do

This was some advice that was given to me by a queer friend. She said, “you already know how to touch a woman because you know how you like to be touched.” While it’s true that every woman is different, starting with the way you’d like to be touched (and listening for feedback via moans, bucking hips, etc) is a good start. For example, I know I really like to be teased and warmed up with lots of light nipple stimulation, that I like kisses on the neck, that I like a super-light touch on my clit at first — so I just started there, intuiting what I would want if I was my partner and giving it to her. It worked!

Take Your Time


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One of the most fun things about sleeping with a woman as a woman is how much more likely it is your partner will be into taking it slow. I made out with my partner for nearly an hour before anything else happened. Take your time. Don’t do anything — or let anyone pressure you to do anything — before you’re ready. Enjoy how soft her lips feel, and what it’s like to touch breasts. Slow everything down and build up tension. If someone gives you a hard time about it, they’re not worth sleeping with to begin with.

Tease Her

I think most women really like to be teased. (Girl Sex 101 backs me up on that.) Tease her in a way that feels intuitive to you — suck on her nipples through her bra, pull at the sides of her underwear in a way that would get your own panties in a twist. Touch her clit with a feather-light touch for as long as you both can stand it. As long as a tease follows through in the end, she makes a great lay.

Let Her Know You’re Into It

Even if you’re feeling timid, you can let your partner know you’re into it along the way by making noises that aren’t just pornographic moans (although those are cool too). A nice mmmm can go a long way in reassuring your partner that you’re enjoying what’s happening and are indeed into girls and her body. (Of course, if it turns out you’re not into it or things are moving too fast, let her know about that, too.)

Warm Up To Oral Slowly & Listen Carefully


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By far the most daunting part of sleeping with a woman, for me, was oral. What if I sucked? (Heh, suck.) Luckily, in reality it wasn’t scary at all — and no, it didn’t taste “weird,” either.

After you’ve teased and been teased as much as you can both stand, take some time to look at her pussy. Spread the lips apart, pull back the clitoral hood, get a good look. Be sure to let her see you staring in awe. The more she feels like you’re into her anatomy, the more arousing whatever you do next will be. Don’t start licking until you really want to — or keep licking past when you really want to. Let your intuition guide you, listen to her vocal cues and body language (bucking her pussy towards you means harder, pulling back means softer), and don’t forget to check out guides like Girl Sex 101 for more specific tips on technique.

Keep in mind that you already know something about what you like, and that means you’re not a true novice. Above all else, stay present, respectful, and communicative. That’s what good sex is all about, no matter your partner’s gender!


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