Welcome to the AF+ Advice Box, in which we answer all the queer and lesbian advice questions from AF+ members who submitted their queries into our AF+ ask box! And…now advice is going up WEEKLY.

Hi. I am a stone butch who has never penetrated someone, but who wants to try. I’m struggling to get over the empathetic feelings of “Aaa! Vaginal penetration is painful and bad” when I know that’s not how a lot of people feel. But it is how I feel about my own body. How do I sort of lean into a more understanding feeling regarding others’ desire for penetration?

Nico: Thank you so much for writing in! To start from the broadest possible standpoint, every single person’s body is different, and also, so is every person’s relationship to their own body and sexuality and what feels good (physically, but also mentally). I’m going to start this answer as though you are perhaps imminently going to have sex with someone who enjoys penetration and you need to get ready. But there’s more general advice regarding mindset at the end, too. A great place to start is a discussion which can be brief and bullet-pointed if it’s a hookup, or more in depth if it’s someone you spend more time with, about what each of you like when it comes to sex and intimacy, what feels good, what doesn’t. Because, even among people who enjoy penetration, there’s a whole spectrum of ways that someone might like to be touched and have their body interacted with. I’m going to outline a few different aspects of penetrative sex you can ask about to get a clearer idea of what your partner might enjoy most:

1. What we know is almost certainly going to be the case with anyone is that there is usually a bit of warming up and arousal needed before vaginal penetration. This can really vary from person to person. How does your sex partner like to get warmed up? What turns them on? You might already know this! Feel free to just skip ahead, if so.
2. How much do they like penetration? Is it awesome, their favorite thing? Is it an accompaniament to clitoral stimulation? Is penetration something they like a little bit of here and there or is it something they want you to focus on?
3. How does your partner like to be penetrated? What positions do they like to be in? Do they like being fingered? Do they like gentle movements, slow movements, hard movements, fast movements, for someone to go deep or to pay attention to their G-spot? Do they like toys? Do they have toys they would like you to use? Are they comfortable showing you how they like their toys used on them?

And that last point leads me into another thing you can ask your partner to do. While you’re getting down to it, you can ask your sex partner if they would be willing to demonstrate how they like to be penetrated. They can use their fingers or the toy they want you to use, and they can show you just what they like. I’m hopeful this will help with two things: for one, you’ll be able to be somewhat assured that if you do what they showed you, then you’ll be doing something they’re going to enjoy — and two, if you see them enjoying being penetrated before you’ve penetrated them, then I hope that will relieve some anxiety for you about hurting them. You’ll see first hand, for yourself, that this sex act is pleasurable, not painful for your partner.

During sex, it’s also great to get continued confirmation. Don’t be afraid to ask things like “Is this okay?” or “How does this feel?” or “Is this too many fingers?” or “Do you want another finger?” Even asking someone outright what they want from you in that moment might yield some fun results! Maybe they want you to also suck on their nipples while you finger them or to get into some dirty talk. It’s totally and very okay to reaffirm consent mid-sex, including multiple times, especially if you’re getting to know someone or trying something new.

To help you understand where someone else might be coming from, I encourage you to explore erotica, whether that’s written or perhaps in audio form. Look for stories from the perspective of a queer person who is enjoying being penetrated. Allow yourself to try to get into the headspace of someone who is experiencing penetration and having The Best Time. While these are nonfiction, we have some recent Sex Diaries that might be good reads. The most recent sex diary actually features the author talking about the differences between her and a woman partner of hers when it comes to the kinds of stimulation that get them off. It’s a super interesting discussion about just how different things can be from one person’s experience and body to the next! The Leather Play Party is written by a trans person who enjoys penetration (among other things!). This sex diary is written from the perspective of a trans man who is fucking his boss. There’s plenty of writing from the perspective of someone who is the one doing the penetrating in this one that might give you a real life example of one person fingering another and having a positive response from that. Exposing yourself to others perspectives can really help you gain a better understanding of all the many ways people might feel about penetration — and other sex acts, too!

This is also going to take trust in your partner, that what they are telling you they enjoy is the truth. If the space you’re sharing with a sex partner, whether this is a longer term relationship or a one night stand, feels safe and consent-based, then you should be able to trust that they’re being honest with you. Finally, sometimes, the best way to get over anxiety around something is to try it. I don’t mean for you to try penetration, no. You already know you don’t like that, and don’t let anyone pressure you into doing something you don’t want to do. But if a partner asks you to penetrate them, and you say yes, and it goes well, I bet you’ll feel a lot better after that. Take a deep breath, center yourself, and go for it!

I’ve been in my slut era, and it’s great. I’m getting good at asking for and knowing what I want. But I’m developing a crush on my regular hookup. We have crazy good sexual chemistry, and share a sense of humor, and we spend like 3-6 hours together every time we see each other, so I know we get along really well. I’m also picking up on some romantic vibes from her, but we’ve already discussed that we’re friends with benefits– I still find myself wanting more. I’m not sure I’m ready for a relationship, but I know I like her. I have a lot of relationship anxiety from a bad relationship I was in last year, and have historically gotten too serious too fast. How can I be patient and let this be natural? How can I be comfortable with casual? And how do I find out what she wants (I know, I know, ask her). I would hate to lose the dynamic we have going on right now– I’ve literally never liked sex this much– but I also don’t want to miss my chance at something good. Thanks in advance for your sage advice.

Nico: First, before anything else, I think it would be good to get clear on what you want. Do you want, specifically, a romantic relationship with this person (even though you say you’re not ready), or do you want to “not miss out”? I think if it’s actually the latter, then this is a great opportunity for you to work on unpacking anxieties or thought patterns you might have when it comes to a sense of scarcity around relationships. You mentioned that you have anxiety from a bad relationship and that you tend to get too serious too fast. It’s super great that you’re self-aware and that you know these things about yourself. Because of your saying that, I’m going to follow a path here that assumes that escalating into a full-on romantic partnership with this hookup / friend is probably not the best thing right now at this time.

So, with that said, I want to look at the fact that you said you “don’t want to miss my chance at something good.” But don’t you have something good right now? Isn’t the sex some of the best you’ve ever had? Isn’t your friendship with this person something you value and that is fulfilling? And aren’t you spending nice chunks of time with her that you’re both enjoying? It sounds like a rich, fulfilling connection right now. And I get the impulse here — it’s so good and you maybe have an instinct that is telling you that you need to do something to make sure you can hang onto this forever or for longer. But the thing is, we can’t actually control a lot of how long any relationship lasts beyond the ways we show up and the boundaries we keep. Even if you did move into something “more” right away, it doesn’t guarantee…anything! To get comfortable with casual, let yourself be present. Romanticize what you have right now. Journal about your friends with benefits situation. Reflect on things in your life from a place of gratitude (you are having the best sex of your life right now, as I understand it?).

And, there’s also nothing wrong with being honest about your feelings, whatever they may be. But that’s why I asked you to reflect on where you’re coming from and what you want. There’s also, sometimes, a romantic side to queer friendships and queer friends with benefits situations. You don’t have to be hard and fast with lines. You can queer things. You have options and you always have the ability to make something that is your own, that works for you and your friend. However, I find that a great way to find out how someone else is feeling is to just state how I’m feeling. You can try being the one to go first, to offer vulnerability and open space for her to share how she’s feeling. And then, of course, you’ll want to respect that vulnerability by accepting that what she tells you is her truth and is what she feels and wants. Maybe it will delight you, maybe it will be something you say “okay, I can handle that,” or maybe it will be too disappointing for you to continue things. But, you know, if your friend wants to be friends with benefits and not escalate things anywhere in particular, and you can be okay with that, then embracing the casual is about embracing the moment, embracing pleasure, embracing yourself as a sensual being who is on this earth for just a little while. Our connections with other people, in all their many forms, can be one of the greatest joys, and a connection does not have to be a huge romantic to-do for it to be meaningful to you. I hope this helps!

Need a deodorant recommendation! What works well with armpit hair, isn’t an aerosol, and won’t leave white marks on clothes??

Valerie Anne: I personally use Native and Schmidt’s natural deodorant and, unless all my friends have been keeping a secret from me for years, they work great. (And I don’t shave my armpits. My hair is pretty thin but it’s decently long.) I started off with Native when I first switched the natural deodorant and loved them, but then got annoyed that their website arbitrarily split scents into “men” and “women” and when I emailed them about it the response I got was like “shrug, that’s how people shop.” So I switched to Schmidt’s for a few years. Then one day I got served an ad that Native has plastic-free packaged deodorant so I went back to their website to check them out and lo and behold, the gendered language was gone! So I’ve been using them lately. I personally love the “coconut & vanilla” and “citrus & musk” scents from Native, and the “bergamot & lime” and “vanilla oat milk” scents from Schmidt’s. I’ll probably stick with Native for a while because I like the plastic-free sticks but I’m sure Schmidt’s can be too far behind on that trend, at which time I’ll probably use both!

Lots of predatory lesbian feelings with this one! So. I’m poly and I have a friend who is also…poly. We’re the kind of very casual friends who will socialize together and maybe in conversation share deep things but we rarely talk outside of seeing each other at larger group gatherings…and she has seemed largely uninterested in having any kind of deeper interactions. That’s hurt me because I have a huge lesbian crush on her and I…didn’t know she was pansexual for a long time until recently, at which point I might have flirted with her a little. After the last time we saw each other when I flirted with her she hasn’t asked me to hang out again. I tried to initiate hangs or invite her to things a couple times and eventually gave up and backed off like you do if you think you made someone uncomfortable. AND THEN YESTERDAY WE MATCHED ON FEELD. Her profile is super explicit about stuff she wants to do with men and says she just wants to slowly explore with queer women and nonbinary people. Is this just a friend like? Ignore that I liked her first. Is this a sign that flirting might be welcome? Should I leave her alone because I’m a lesbian and I’ve been dating women forever and she’s maybe not looking to be with someone who has as much queer experience? Being in your mid / late 30s is rough out here I don’t know what to do but my brain is melting because she’s so hot and funny and awesome.

Drew: While people disagree about whether a match on a dating app with a friend is just friendly or implies something more — personally, I’d never swipe right on a friend unless at least part of me was open to more — at the very least I think it’s an invitation to explore. I also think feeld is specifically more sexual than if, say, you’d matched on Tinder. And I think the most revealing aspect of this — other than, ya know, matching on a dating app — is learning she’s not as experienced with queerness. That explains the possible timidity! I fundamentally don’t believe there’s anything wrong with a more experienced queer hooking up with a less experienced queer. As long as you understand she might need some patience and may not be 100% sure what she wants.

My suggestion would be to be very direct but not pushy. Ask her out! But be casual about it! She’s probably not ready to dive into a relationship — or even dive into bed — but she might be open to a date. I’d start there and then take her lead with what happens next.

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