Illustration by Erin Aniker
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 Trisha O'Bannon about her experiences of dating after a long-term relationship ended. You can catch My First Time on Acast, Google Play, Apple Podcasts, Stitcher, or wherever you get your podcasts.
I was in a four-year relationship with a guy I met at a gig. We lived together for two years and had met each other’s parents and would joke about things like marriage and kids. Around three months ago, we broke up. Things had been strained for a few months, and we’d stopped having sex. The lack of intimacy definitely contributed to the breakup—it drove a wedge between us, because we didn’t feel as close physically or emotionally. There were also a lot of external pressures on the relationship. It got too much for both of us to handle, and he broke it off.It took me about a month to start dating again. I went back on dating apps and started going on random dates with people here and there. I did have sex with someone I was casually dating. By this point it had been over four months since I’d last had sex, so I was excited to let go and do it. To be honest, I didn’t really enjoy myself. It wasn’t uncomfortable or painful, but it was just weirdly awkward and unsexy. There was this voice in my head saying, Is this worth it? I should just stay at home and masturbate and save money and everybody’s time.After my relationship ended, I’d say there was a lot of fear in opening myself up and allowing myself to be vulnerable again. Although I’m a very sexual person, I have a personal philosophy about sex: I can’t have sex with someone I don’t have a connection with, even if it’s just a platonic connection. I’m getting older! I don’t have the time to deal with people I don’t want in my life anymore.
I live in Manila, which is an extremely Catholic, conservative place. There’s a huge emphasis on saving yourself. “Why buy the whole cow if you can have the milk for free”—that sort of thing. It takes a lot of courage to tell someone the things you like to do in bed, especially in a country like the Philippines. What other cultures might not think is kinky is completely taboo here. For me, having sex with someone new involved so many different risks. There are the social risks—will people think I'm a slut? The physical risks—what if I catch an STI? And the emotional risks—what if you fall for someone you’re sleeping with, and they don’t feel the same way?The turning point for me was when I went to a concert. I went to started talking to the cute bar tender, and by the end of the night I had her number. We went out a week later for the first time. She’d actually also just gotten out of a long-term relationship, so we were both in the same headspace of not being ready to have another relationship. We were both really upfront about it.On our first date, we’d originally planned to just hang out and have a drink as friends. But we ended up staying out under 3.30 AM, just talking. Neither of us expected to hit it off so well. Within a week I’d hung out with her friends and got to know her better. At this point it was a bit unclear as to whether she liked me that way, or just wanted to be friends. But one evening after we’d been hanging out she texted me and said, “I’m disappointed I didn’t go home with you.” So then I thought, That works!
I’m a burlesque performer, so I invited her to a show I was doing the following day. She came up to me after the show, and I was so nervous, I was actually shaking. Another factor was that it had been six or seven years since I’d slept with a girl, so I was doubly nervous. I thought, What if I don't remember how to do this? It'll be the worst sex of her life, and she'll never talk to me again.
In the end, we had a few drinks so we’d have liquid courage, and went back to my place. We stayed up pretty much all night. We got along so well, and the things we liked to do in bed synced up perfectly. I’d been wondering whether I would miss having sex with men; whether there would be something missing from the experience of sleeping with a girl, for me as a person who mostly slept with men. But it didn’t feel like that at all.The most important thing was learning that I was able to meet someone who I’d have the same connection that I’d had with my former partner. I didn’t know if I’d be able to have inside jokes with someone; if I’d ever find someone I could talk with until 5 AM about everything and nothing. Would I ever be able to find someone who’d find me physically attractive and indulge me in my fantasies and the things I want to do? I was terrified, because I’d built that for years with my ex-boyfriend, and it was gone. I kept thinking, Do I really want to put all this work into building something new, if it’s just going to die again?But after hanging out with this girl, it felt like—why was I ever scared of that? Why was I in fear of never finding someone ever again, when there are literally billions of people out there in the world? It seemed funny that I'd thought I’d never be able to connect with someone else. I’m so grateful that I was able to. It taught me that I’m not closed off, I’m not stuck with who I was before, and I’m moving on. Every day I’m getting closer to the type of person I want to be, and I’ll be able to find a person I want to be with again.I’ve learnt that sex is a form of communication between two people. Sex can be amazing with one person, and awful with another. Even if you’re out dating again after a long time, and you’re struggling to find someone you get along with, there’s a lot of hope in knowing that the next person may be different. It’s all about getting out there and finding someone you like and you can communicate with, because sex is rarely good the first time—you need to build up trust and get to know someone.Just find that person you’re willing to go through that process with, and realize that it may not happen with the next person you date—or even the next ten people you date. But with each person you date you get so much closer to the next person you’ll really like, and want to take that leap and be in a relationship with.