What We Wish We’d Known Before Having Gay Sex for the First Time

Whether it happens at 18 or 80, few among us feel like we go into our first girl-on-girl experience feeling over prepared. While we can’t tell you exactly what you might need to know, like a wizened mysterious guide of lesbian sex appearing from the shadows, we can tell you what we wish we had known our first time!


Archie Bongiovanni, Cartoonist

Pack your own lube, don’t count on the other person having any or having a brand that won’t give you a raging yeast infection.

Also: Sex can be bad. Gay sex can be bad. If there isn’t a spark before the bedroom, there probably won’t be any sparks in the bedroom. Don’t dwell on this, it’s not worth overthinking.


Bailey , Writer

Laughing is sexy and vulnerable and safe and it’s totally okay to have a wholesome giggle at any point. Also, don’t overthink it! Sex is meant to be fun and feel good for all of you.


Dear 21-year-old me, let me save you a few years: You’re a bottom.


God I feel like it’s cliche but: communication! It’s so strange to think that we have been socialized to think that good sex just happens magically with no conversation and everyone just gets it from jump? It makes no sense! People are different, talk about what you like and what you don’t like, let your partner do the same! Also you can fun during sex? Silly sex is great!


Dani Janae, Writer

One of my early sexual experiences was with a woman that wouldn’t go down on me because she “doesn’t eat hairy pussy” and I wish I had known some people are absolute babies during sex. I would tell my younger self not to be afraid of being pleasured. I was definitely a touch-me-not for a few years and just generally had a numbing bad time during a lot of my early hoe years. Working on an essay that centers around this a little so I won’t say much more but yeah, I would tell myself to relax and not be afraid to enjoy sex.


Drew Gregory, Writer

Just because you have a fully functioning dick doesn’t mean you can’t wear a strap-on instead.


Heather Hogan, Senior Writer

I wish I’d known how to relax! My inability to relax has ruined so many things for me! And when I look back on the first few years of my gay sex life, it’s clear it could have been 85% better for me and everyone I slept with if I was capable of just chilling the fuck out! Also I wish I hadn’t had my heart set on really good bathtub sex after so many fan fictions promised me how great it would be. I have had some really mediocre bathtub sex, which was always such a disappointment because I do love baths so very much — and also I have accidentally whacked my head or knees or elbows against the bathtub enough at this point that I probably have a permanent concussion from it.


Kamala Puligandla, Deputy Editor

I wish I’d been masturbating with penetration more before I started having sex with other people, so I had known better what I did and didn’t like.


I would like to tell my younger self that she will really, really like gay sex and does not need to spend so much time and energy on trying to convince herself otherwise!!!!!!!!

Also tbh I WISH I HAD KNOWN WHAT TOPPING AND BOTTOMING REALLY MEANT instead of the v rigid ideas of these categories I had in my head as a baby gay. I mean, I feel like I’m STILL adding to my personal definitions of these terms, but it would have been nice to have a stronger base knowledge. I also didn’t start using toys until way late in the game.


Malic White, Writer

1. You won’t have fully satisfying, technically-sound, mentally-generative sex right away. Accept that there’s a learning curve, you eager little Aries.
2. Sexual compatibility is actually important. If you’re not sexually aligned with the person you’re dating, get the hell out of there. There are plenty of queers who like what you like.
3. It’s ok for kink to be a requirement instead of a garnish.


Rachel Kincaid, Managing Editor

As a rookie fingerblaster, especially one who was bisexual and felt somehow extra “inexperienced” because of that, I was (understandably!) very worried about being “good in bed” — despite the fact that I had at that point logged countless successful sexual acts with boys, the idea of successfully getting a girl off felt incredibly high-stakes and scary. It’s true that I didn’t like, get a Matrix-style brain download from Sappho about fingering techniques my first time with a girl, but I wish I had known first that that wouldn’t matter that much — what, like anyone else was any better at that point in our lives? — and also that I had worried more about my own experience. I had no idea and it hadn’t even occurred to me to think about what would feel good to me, what iteration of “lesbian sex” sounded hot to me, how I would talk to someone else about how they should be touching me; I wish I had put at least as much energy into thinking about that as I did trying to figure out how to win a blue ribbon at lesbian sex.


That lesbians have bad sex too. Porn and MTV made me feel like every time i had sex with a woman there would be fireworks, crying and cuddling. Not the case; it takes time to learn not only the bodies of your partners but your own. Also, I wish that I knew way earlier on in my sexing game that strap-on sex (giving or receiving) doesn’t make me any less of a queer lesbian. I can have you inside me or strap you down something crucial and still be a total dyke.


Stef Schwartz, Vapid Fluff Editor

“You’re going to be good at it.”


Vanessa Friedman, Community Editor

I like to be prepared. I’m a Capricorn and I’m very anxious and I’m always trying to do my very best. So, growing up, when I thought I was straight, I decided I better prepare for SEX. I wasn’t sure exactly what that would entail, but I knew I didn’t want to be unprepared the first time I was called upon to HAVE SEX. I set up an agenda: I needed to learn to makeout by the end of seventh grade, should get felt up by the end of 8th, give a blow job by the end of high school, and lose my virginity (which to me at the time meant very heterosexual vanilla penis-in-vagina sex) by the time I was 18. I hit all my goals, because I am nothing if not determined when I set out to accomplish something, and turned 19 feeling proud of myself for mastering sex. Imagine my complete dismay and actual total terror when, at 20, I had sex with a girl for the first time and had barely studied for the test at all! I had prepared myself for various sex and sex-adjacent options with cis boys… I had never thought to prep for what would happen if I was tipsy and making out in my empty dorm room with the most handsome girl I had ever met in my entire life. I gingerly traced her tattoos and the brand mark she told me her roommate had given her the year before; I put my hands on her hips and memorized the yellow American Apparel briefs she wore, the thick white waistband rubbing roughly under my palms. We made out for a long time and she put her fingers inside me, but when it came time for me to tug down her underwear I must have seemed very unsure because she stopped me and asked if I was okay. “I don’t really know what I’m doing,” I confessed. I felt like such a failure.

I wish I’d known that there’s no such thing as “knowing what you’re doing,” that even though I’d diligently stuck to my practice schedule through my preteen and teenage years, even if I’d turned out to be straight, I still wouldn’t have been guaranteed an A in every sexual encounter. Sex isn’t a test, is what I wish I’d known. That’s okay, though – I know now.


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24 Comments

  1. TW: relationship abuse
    I wish I had known that isn’t okay to be pressured into sex. I feel like no one ever told my baby dyke self that my consent was important or that I wasn’t obligated to keep my girlfriend with my body.

  2. Oh my god Rachel this is such a bisexual mood, thank you. My thought when I read this title was “let go of the fear of being “good in bed” and lean in to communication and pleasure in the moment with someone”.

  3. HOO BOY as a fellow nervous Capricorn who wants to do things 150% right, all the time, Vanessa: yeah. yeah. uh-huh. thank yooouuuu.

    For me though: “you’re a top, and that’s cool, and it’s okay that you like to feel powerful and in control, just let it happen”

  4. I wish I’d known — really known, understood and embraced — that everybody likes different things, and there is no shame in something just feeling GOOD. It won’t be the exact same thing your partner likes, or the thing you read about online: it’ll be the thing that gets YOU off, and that makes it absolutely the right thing.

  5. Having it constantly drilled into my brain by other queer girls that “scissoring” isn’t a thing (mainly because of mainstream porn not actually created by queer people), I would have loved the clarification that tribbing is very much a thing and lots of us do it. If you connect right, it’s amazing! I guess what I’m saying is there’s a lot of community members that seem to imply there are limitations when it comes to lady sex and that it really just involves fingers and occasionally oral. Not sure if I’m the only one who has experienced that? But when I first had sex with a girl I was actually relieved that we did far more than just “fingerblasting” XD

  6. I feel like this definitely did not get mentioned at the clinic – having sex with a yeast infection isn’t great but is doable, but giving oral sex to a girl with a yeast infection is a TERRIBLE FUCKING IDEA. Think squirting, but instead of fun sexy times, just yeasty, chunky, cottage cheese horror. All over your face.

    • This also did not get mentioned: do not give oral sex to a girl if you have thrush! Because she will get a yeast infection.

      Shoutout to the girl I was dating who still wanted to me to be her gf after I made her so itchy.

  7. As a recovering perfectionist and straight A student, Vanessa had me ROLLING. My friends used to say when I finally decided to have sex I’d be like Liz Lemon when she schedules sex and gets turned on by paperclips. Glad I know better now ;)

  8. It’s okay if you feel nervous about having sex for the first time. It’s not okay if the person you are about to have sex with makes you feel nervous. Listen to your gut.

    Keep it simple. Even if you know you are kinky, maybe start off a little more on the basic/vanilla side of things and explore slowly from there.

    And also… vagina art wallpaper should be a tip off. Run!!!

  9. I don’t know if anyone is still reading these comments, but I have been chortling admiringly (which I’m not sure is even a thing) all week over Stef’s VERY pithy and confident: “You’re going to be good at it.”

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