My First One Night Stand Was So Bad, I Almost Gave Up On Casual Sex

My First Time is a column and podcast series exploring sexuality, gender, and kink with the wide-eyed curiosity of a virgin. We all know your "first time" is about a lot more than just popping your cherry. From experimenting with kink to just trying something new and wild, everyone experiences thousands of first times in the bedroom—that's how sex stays fun, right?

This week, we're talking to Florence Barkway, co-creator of sex-positive YouTube channel Come Curious, and co-host of sex podcast F**ks Given. You can listen to My First Time on Apple Podcasts, Google Play, Spotify or wherever you get your podcasts.

I was 16 when I had my first one-night stand. I’d just gotten out of a relationship with my first love, and the guy who I lost my virginity to. Although we’d been together for 11 months, we’d only actually ever had sex twice; so my first one-night stand also ended up being the third time I’d ever had sex.

I’d gone partying with some friends and we ended up in this grotty club that was the only place that would let us in, because we were underage. I was wasted, in the smoking area, and I started chatting with this guy. He was in the same friend group as my ex-boyfriend. I ended up kissing him in the club—actually, if I’m being really honest, he fingered me in the club as well.

By the time we got back to his house, it was really late, or really early depending on how you look at it. I remember it was actually daylight as all of this was happening. My memories are really vivid: We were naked, fumbling, having this clumsy sex like teenagers who didn’t know what they were doing—because that’s exactly what we were. The sex was shit. I know we tried 69-ing at one point, because I thought, Ok, let’s try this out, I’ve seen this in magazines.

As we were having sex, the condom tore. I panicked: It was the third time I’d ever had sex and the first time I’d have sex outside of a relationship and now the condom just broke! I thought, Oh my god, I’m going to get pregnant. Inside I was screaming, although I didn’t really say anything to the guy. I think I just said, “I’m going to have to get the morning-after pill,” and he said, “Yeah, I guess so.” We never spoke again after that. He never offered to pay for it either! I think we saw each other a few times in clubs or at parties and avoided each other.

It was a Sunday morning and all the doctors were closed. I was panicking and phoning up all these places to see if I could get Plan B, but nowhere was open. I got to the end of my list of places to call and because I didn’t know what else to do, I went home and told my mom. She seemed so disappointed in me: I remember her facial expression turned from concerned to slightly angry. I could just tell she thought I was being reckless, and stupid. There was this wave of disappointment coming off her. I can understand why: I wouldn’t want my teenager to be having sex with random people they’d met in a club.

We ended up finding Plan B at a pharmacy that was open, and bought it: I remember it felt like a lot of money at the time. We went down to the beach near where we lived and I took it there. I remember standing on the pebbles, and feeling so incredibly disappointed at myself. The sex had not been worth it, at all, and I felt like I’d really let myself down. I felt a lot of shame as well. And it didn’t help that I was hungover, and the Plan B itself made me feel even more sick. All I could think was, Why did I do this to myself?

For years after that incident, I was really put off having one-night stands because I felt ashamed of how that night had played out. When I was a teenager, I was at my least confident sexually, and that disastrous one-night stand really shook me. I felt ashamed of it for a really long time, but conflicted, because I also loved sex and wanted to have more of it. Looking back at it, it’s sad that what should have been an innocent experience became something so shameful and embarrassing.

After that one-night stand, I got into another relationship with someone for two years. I think part of me felt like I should be in a relationship so that I could get over how horrible that one-night stand was, and have sex that felt less shameful and guilty. I ended that relationship when I was 19, because I wanted to explore more sexually and have sex with different people, rather than be in long-term relationships throughout my teens. For the first time, I made it my mission to have one-night stands because I felt more.

One-night stands have been a valuable experience for me because they've given me a deeper understanding of what sexually satisfies me and how to identify what others may enjoy. I run a sex-positive YouTube channel and I don't think I'd be able to do that if I hadn't had all those one-night stands. That said, I do think that it's important not to only have one-night stands. Yes, they're a lot of fun, but in my experience, building a foundation with your partner is the most intimate kind of sex.

I think that one-night stands can be very beneficial to understanding yourself sexually. The whole point of having a one-night stand is to have fun, though, so you shouldn’t do it if you’re not in the right frame of mind. Don’t have sex with someone because you’re feeling shit about yourself, or need validation through sex. Because the next day you’ll just feel rubbish, and why would you want to bring that negative energy into your life?

Always have a one-night stand with positive intentions: Have clear boundaries, communicate with your partner, make sure it’s someone you trust—and have fun!