"I was apprehensive about sex as a teenager. I didn't feel ready, and I definitely harbored fairy-tale fantasies about my first time being with someone who felt like a soul mate. In college, I carried that with me, so I hooked up and went almost all the way, but never quite there. And by my early 20s, the weight of my inexperience held me back in relationships — out of fear of being discovered for this thing I was missing, this knowledge that I didn't have.
"Eventually, I slept with a guy about five dates in, and stopped seeing him a few dates after that. So, when I started seeing my next boyfriend, my experience was pretty limited. When that relationship, which had consisted of a lot of missionary sex and limited orgasms, ended six months later, I still didn't feel like I was where I was supposed to be, as an adult in charge of her own sexuality. I didn't really know how to ask for what I wanted, or really, how to figure out what I wanted, when I wasn't on my own.
"Essentially, I had lost my virginity at 26, so this moment of singledom felt like my opportunity to do something a little reckless. I joined OkCupid. I laid low for a while, emailing guys and going on some dates, but never feeling comfortable enough to go home with any of those men. And then I heard from a professor who was a few years older than me, and emailed him back just once before asking if he wanted to meet for a drink. He did. We went out on a Sunday night and hit it off. I didn't feel a real connection — or in all honesty, real chemistry — but I did feel pretty comfortable with him, having easy conversation and laughing a lot. Three drinks later, we left, made out in the street, and headed in the general direction of both our (conveniently neighboring) places. When he offhandedly was like, 'I don't supposed you want to come up, just for a drink,' I surprised him with a yes. We went up to his place, started making out, and things easily escalated. And for the first time, maybe because I didn't feel any real pressure or expectations, I was able to be more vocal about what I did and didn't like. I put his hands where I wanted them. I stopped worrying about whether the jiggle around my middle was going to be unattractive if I got on top. And ultimately, I still didn't orgasm that night, but I did change some of my own ideas and inhibitions around sex and intimacy.
"But still, the next morning, I woke up before 6 a.m. and felt really uncomfortable. I didn't want to be there. So, I lied about an early meeting, left, and never called him again. And he didn't call me, either. The only problem: Despite the fact that I didn't want to see this guy again, the fact that he clearly felt the same, and was on the same page as me, felt like tacit rejection. Which was hard. That's why I never did it again, but in a weird way, it's one of the most important things I've ever done for myself." Illustrated by: Abbie Winters