Here’s What I Learned From Having Sex With A Woman For The First Time

Here’s What I Learned From Having Sex With A Woman For The First Time

About a year ago, I had sex with a woman for the first time.

Before that night, I had simply kissed and pined after feminine bodies I was attracted to. My embarrassment over my queerness was one of the reasons why I didn’t allow myself to act or date according to my sexual orientation, until last year.

I was raised in a home where my lesbian aunts’ girlfriends were introduced to me as their “roommates” and my mom’s version of teaching me about sex was to explain vaginal, penetrative sex only.  For a majority of my life, the thought of wanting to have sex with girls and for having secret girlfriends, was my well-kept secret.

Then I came out as pansexual in college.Coming out when I was 20 years old led me to my first sexcapade with a girl a year later. We matched on OkCupid, and we talked extensively about our boundaries and interests. Finally, we came together in a Brooklyn hotel room and while some of it was eye-opening and awkward, I learned a lot about sex and myself from this new experience. Here are some of my takeaways:

Sex Should Be Communicative and Respectful

My date with OkCupid girl, as we’ll call her for privacy reasons, was the first time I had established boundaries, safe-words and a list of acts that were off-limits. In my experience with men, sex was a rough-and-tumble mess that was mostly satisfying and had a “we’ll talk about it later” feel to it. But I loved the way this girl led the conversation about these very important things.

While I was eating OkCupid girl out, she laid still with her eyes closed without making a sound. I felt worried for her and stopped, asking if she was OK and if I was making her feel good. She told me she was fine and that I was, but that she was just used to her partners wanting her to stay quiet during sex. This was tricky for me to hear, as it didn’t sound like she meant “be quiet” in a kinky submissive way. She seemed solemn when she said it. I told her, “I’d love if you wanted to make noise, so feel free.” She allowed herself to make some noise as I continued to go down on her.

This exchange made me grateful for the line of communication we had established, as it made me aware what was bothering her and why. Her sharing allowed us to bond over shitty past male lovers we had and gave me a lot to meditate over on how I could have even more respectful and intentional sex going forward.

Oral Sex Can Be Even More Fulfilling

Giving her oral sex only reassured my primary attraction to people assigned female at birth. But for the first time, I was presented with very different genitals in my face and on my taste buds…and it was an amazing difference to say the least. I really felt like I was having so much fun, something I never felt in casual encounters in giving cis men blow jobs. I felt so grateful to be receiving that experience.

It was additionally wonderful to have a mouth unhindered by facial hair going down on me. My partner assigned male at birth gives me the Best Ever head with facial stubble and all. But still, it was nice to feel that smoothness this one time.

All Bodies Are Good Bodies

After sleeping with her, I realized that my sexual experiences were incredibly homogenous and included only thin and toned white cis men (with a few exceptions, which now includes my fiance). With her, sex included a squishy belly, wide tattooed thighs and happily fumbling through positions that worked for both of us.

She was also the first person I’ve ever been with who’s completely shaved, and I was the first person assigned female at birth she’s ever been with who’s completely unshaven. It was fun for the both of us to explore each other’s vastly different bodies, and appreciate the sexy things about each other we weren’t necessarily familiar with.

Orgasms Aren’t Everything

Orgasms are very important to me and everyone I’ve ever been with, but she was the first person I had personally encountered that didn’t feel this way. She told me before we had sex that she usually doesn’t climax during sex with others, and to not prioritize that during our time together. I appreciated her confident communication on the subject, but still found myself struggling in the learning curve. At different points, I might have went on for a bit long with the autopilot intent on making her orgasm, but I would catch myself and laugh or change positions.

I now see that avoiding that race to a finish line makes sex way more enjoyable. While I still love orgasms so much, I see that the journey alone can be just as satisfying as the destination.

Vaginal Sex Isn’t Everything to Everyone

During sex with OkCupid girl, neither one of us were vaginally penetrated…and we still had a great time. In the past, the existence of my vaginismus always led to awkward conversations with my male lovers, but OkCupid girl was incredibly kind and respectful about my wishes. Even for someone who can experience vaginal sex, she fully believed we could have a good time without it–and we did! Having been shamed for my pelvic pain disorder many times in the past, this was refreshing.

Exploring The Full Spectrum Of Your Sexuality is Crucial

I felt like I understood myself much better after this experience, as I finally allowed myself to move closer towards pursuing the fullness of my sexuality. And while my sexuality spans vast territory, as I’m attracted to people of all gender identities, it was my first practice in exploring outside of the bodies I’ve known personally. And for that, I was thankful.

Cover image courtesy of Getty Images.