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Q: My girlfriend and I broke up about four months ago. She was the first girl I was ever with, and we were together for almost three years. About halfway through our relationship, she admitted to me that she had been “faking it” every time we had sex. She told me she never once had an orgasm (despite what she said during sex) and that I was so bad she lied and avoided having sex with me. Like she would tell me she had gotten her period twice in a month. She said at first she tried to be patient because she knew this was my first time having sex with a girl, but eventually when I never got better she hated sex with me. This completely destroyed my already broken self-esteem. To make matters worse, after telling me this, she never had sex with me again. Every time I tried talking to her, and asking her what she wanted and advice for how to make her feel good, she said she didn’t want to talk about it.
Now that I’m single and finally able to move on, I am terrified to have sex with another woman. I feel extremely insecure. I’m 23 years old, and I’m regretting coming out of the closet so late. I dress a little butch, so I feel like the women I’m talking to are expecting me to be the top and know how to get them off. I went on a date this past weekend but the woman turned out to be a gold star, which terrifies me because I feel like since I’ve slept with men in the past, I’m not going to seem like a “real lesbian.” I don’t know where to go from here when it comes to dating women. I feel like younger, less experienced women, like me, want someone with more experience to “show them the ropes.” And older, more experienced women want someone who hasn’t just stepped out of the closet.
A: Oh wow. First, let’s take a deep breath. It’s so upsetting that your girlfriend did those things! This is about more than just sex skills; this is about being in a relationship that doesn’t seem to have made good sex possible. With that said, it’s important to keep some things in mind.
A lot of people have a lot of first girlfriends and a lot of them are shitty! Congratulations, you made it through. You are a badass. And there are gonna be so many more girls who love the way your hair falls in your eyes or who love the way you make tea or the way you do those things with your fingers and your mouth.
But first, you have a lot of ideas about the way you think things should be, and this is a good time to let yourself realize that they’re not necessarily true.
For instance, it’s not going to help you, your sex partners, or your sex life to try to imagine what other people might want or expect from you in bed. You can’t know what other people are thinking until you ask them. Sometimes you won’t know even then. Butch-presenting people can be bottoms. Femmes can be stone tops. Lots of people are switches, or all of these things, or none of them. The person sitting across from you on a date could want anything in bed, and (hopefully) they’re not assuming that you only like/are interested in certain activities because of how you look, either.
Also! “Gold star” is a construction of the patriarchy and less useful than old gum. No one is more or less “real” than anyone else. None of these things will tell you that it’s better when you move your fingers up and to the left when you’re inside of them or that they really like it when you bite them almost hard enough to draw blood or that nipple play is out under any circumstances or that they like it when you use the big cock tonight, darlin’, or when they get to strap on first or last or always or never. Forget all your ideas about what the person across the table from you might want until they tell you so you can actually listen when they do.
And you know what? It feels like you’re coming out late no matter when you come out. If you come out in your fifties you wish you’d come out in college. If you come out in college you wish it’d been high school. If you come out in high school you wish it’d been middle school. We as a society rely on personal history as a foundation for identity and without that history it can feel scary to declare that your identity is legitimate. It is okay to know that you’re queer and not know the ideal way to fuck the person in front of you yet. A lot of people are in that boat. (Also just because someone is out doesn’t mean they’re having tons of awesome gay sex all the time always, even if it seems like they are.)
There are reasons people come out when they come out. There are a million different things that affect where you are in your life and contribute to exactly where you are right now. Where you are in your life right now is okay. And very few lesbians, if you tell them — at 23 — that you used to sleep with men, will be surprised or not want to sleep with you as a result, except for assholes. If you’re worried about it anyway, just don’t mention it. You don’t owe them that. “Hey and also I used to sleep with men in my teens before my three-year relationship with my ex-girlfriend that ended a few months ago and also we were bad at sex together” is defensive — you’re disclosing it because you feel like it’s their right to know, like they’re considering damaged goods. Do not be defensive of who you are. Taking your time — and honestly, you have not taken that much of it — to figure out who you are is nothing to be ashamed of.
Confidence is key. No queer lady person, gold star or otherwise, is going to lay there thinking, “Ugh, she’s going down on me and I can totally tell she’s slept with boys before.” NO! Your head is between her legs. That’s what she’s going to be thinking about. Especially if you’re asking, does this feel good? Does this? When she says yes, do it a thousand times until she comes or asks you to stop or you move on to other sexy things together.
So let’s talk about how you get confident.
This very website has a lot of guides on how to have lesbian sex. Read them. Study up. Check out the Vice guide to oral or search for instructional sex videos on the pornier parts of the internet or straight up watch some queer porn. (Porn is not often instructional, but it is good for ideas.) Some of the the things you will learn will be a number-one crowd pleaser for everyone until you meet that one person that thing just doesn’t work for. Sometimes everyone will hate something until that one person begs you for it. That’s okay! That doesn’t mean you’re bad at sex, it means that different people are different. The point of research isn’t even necessarily learning, though hopefully you will. The point is to make you feel like you know what will work, so you have a chance to find out what will work for the person in front of you. The key is faking everything except your orgasms until you make it.
Also, the only way to figure out what is working or might work is to ask. I’m so sorry that your previous partner wouldn’t meet you halfway on this, but please don’t let that turn you off of talking about sex altogether! Talking about sex is super fun, and if you have the chance to do it in advance even a little then you should jump on it. You can also engineer that chance. You don’t have to say, “I want to talk about sex now,” but can mention this cool new sex toy you saw on the internet or ask whether you can bring anything if you’re going over for dinner — wine? dessert? riding crop? — in a way that could be construed as a joke if you’re nervous and she’s not into it, but that could also lead to discussion.
It’s also important to try new things until you figure out what works. This is important for responding to activity partners, and it’s important for your own growth and development as a sexual being. There might be something you think you like that might be terrible in real life, or best left as a fantasy, or that works in some ways but not others, or that is the only way to want to fuck for the next three months. There is a reason people refer to sexy times as “play.” Sex is a weird and awesome thing that sometimes makes no sense and sometimes is the only thing that makes sense and it is always supposed to be fun, so have fun with it.
If you don’t have someone to practice with, practice on your own. Masturbate furiously. Find out what you like and let you brain carry you in different directions.
You also need to figure out how to rebuild from this relationship that has destroyed your self-esteem. Again: masturbate furiously. Find a therapist. (Maybe not both together.) You were not your ex-girlfriend’s ideal sexy person. This does not mean your moves will not be great for someone else. Some people just can’t have good sex together, and that’s okay. She also spent a year and a half lying to you and another year and a half refusing to engage with you, which sounds really selfish. A caring partner who wants sex to be part of your relationship will give you all the room in the world to figure it out, especially if you’re willing to listen and learn and take direction. Make sure you are willing to listen.
There is no one way to fuck someone. Confidence is key and physical attraction is great. Are you attracted to this girl you went on a date with? Go on a date with her again and see what happens! Don’t assume she won’t want to sleep with you until she tells you that. The sex stuff will work itself out.
