For a long time, it didn’t bother me that I was a 20-something virgin. Tina Fey was in her mid-twenties when she first had sex and look at her now. She and Mindy Kaling, another former 20-something virgin, are my comedienne inspirations, proof that maybe those who run a little behind romantically can still end up living perfectly happy, successful lives, and in the entertainment industry no less!

I knew why I was still a virgin. I’m a classic over-thinker and have backed out of every single romantic situation I’ve ever found myself in. Blame it on a history of low self-esteem, being annoyingly hyper-logical, a strong desire to keep my wits about me, and being overly aware of my surroundings. It never happened for me, because I wouldn’t let it.

My reasoning behind posting an ad on Craigslist is a little fuzzy. I felt overwhelmed by sexual energy like never before and thought at the very least I could see what’s out there. It was more direct than finding someone on OK Cupid or another dating site, and I don’t even like going out to bars with friends.

I wasn’t looking for any kind of emotional attachment, just physical satisfaction. Frankly, I wanted to see what the big deal was about sex. I didn’t want to go into my 27th year with the stigma of being a sexually inexperienced woman, even if no one knew but me.

I was partly inspired by my close friend, Carly, who recently entered into an open relationship and spends lots of time regaling me with tales of her random, meaningless hook-ups. I had been lying for years about having sex (I didn’t want to be seen as that weird, old virgin), but I have a good imagination and lots of experience watching pornography and having sex with myself. The truth is I never really intended to go through with meeting someone from Craigslist.

But there I was, sitting in front of my computer typing a clear and concise casual encounters ad. I used classic hook-up ad vernacular: “BBW wants a discreet encounter with a nice man. Cannot host.” And so on. I did not include the fact that I was a virgin.

I set up a gmail account under a fake name and waited for emails to roll in. And roll in they did. Almost immediately I had a world of men looking to hook up with me. The sheer amount of dick pics I got was staggering and I fluctuated between academic fascination, passive arousal, and outright disgust looking through all of them.

Several dozen emails later I read one from a relatively unattractive, but seemingly nice man named Stu, who was 27. He looked familiar to me, but it wasn’t until I met him in person that I figured out how. He had actually messaged me on OK Cupid the week before, but I read his profile and never responded (that right there should have tipped me off, I almost always respond to OK Cupid messages).

We started emailing back and forth (over 30 emails passed between the two of us) and finally we set up a time (10 pm) and a place (his townhouse) to meet. He kept reassuring me that he was harmless, unless you count his “giant cock.” I was, in fact, not reassured, but I was fairly sure he wasn’t going to murder me.

I kept pushing away the voice that kept telling me to stop and got ready for our meeting. It felt like an out-of-body experience. Thinking back on that night I see it from the outside, looking in. Watching myself do this, remembering that it happened and yet not feeling like I actually experienced it. Before I left my house, I texted Carly about what I was going to do (she was actually pretty supportive, but didn’t know I was a virgin) and the address where I was going. Up until now, she’s the only other person who actually knows what I did.

I parked my car and Stu was waiting at the front door. We shook hands and went into his backyard. It was nice, there was a fire pit burning and a half-empty bottle of Moscato waiting. I sat down and promptly drank all of the wine in an attempt to calm my nerves and also to catch up with Stu, who was very obviously drunk and high.

We started chatting, about him mostly. I did not like him. He was very much into talking about how Alpha he was and dropping a comment every single time he could about his self-proclaimed gigantic penis. (This turned out to be true.)

He packed a bowl for me and I lit up in a greater attempt to lose myself. He started going on about how LGBT individuals online were bringing a “wave of hate” into spaces they didn’t belong. I suggested we change the subject because at this point I, a queer, liberal, socially aware woman, was pretty close to leaving. But I again squashed down that part of me.

About 20 minutes later I needed to pee pretty badly and the guest bathroom was right next to the front door. I went in and looked at myself in the mirror. I couldn’t think, I wouldn’t let myself, but there was a small part of me that wanted to just leave. Go out the front door and go home. And, looking back, I wish I’d listened to that part.

But there I was and for some reason I still cannot fathom I was still wanting to hook up with him, who at that point was nothing more to me than a penis-wielding person. I just wanted to get it over with.

When I came back out of the bathroom, he was sitting on the couch in the living room, waiting for me. So I sat down next to him and he slowly worked his way into cuddling with me. I was apathetic and pretty stoned and just stared at the moon. He kept talking about stuff I didn’t care about, including reciting a poem he wrote in high school (it was called “Dark Souls” and it was truly, truly awful).

Finally I’d had enough small talk and we started kissing (it was also terrible, just saliva everywhere and at one point he sucked on my tongue like he thought a milkshake would come out of it and that was really weird). Eventually things just went from there. We moved from the couch to his bed upstairs and there it happened. And it was not the worst thing ever, but it was pretty bad.

I did manage to have an orgasm in there somewhere (that I was mostly responsible for), but he just kept going and going and going and my god, having stamina is supposed to be nice, but I was tapping out and he just kept going, to the point where I was physically uncomfortable.

Suddenly, all of my logic and reasoning that I’d been pushing down came flooding back and the reality of my situation came rushing into my head, hilarious and frustrating. A series of events that led me to a stranger’s bed and him trying to look deeply and sensuously into my eyes and me trying to not act like it was as awful as it was. Eventually I just had to stop him and I ended up standing over him telling him everything he wanted to hear just so he would finish and I could go home.

Once I got back to my house and into my own bed I couldn’t sleep. I kept replaying the evening in my head and while I kept trying to tell myself that I didn’t regret it, I did. I still do.

I always thought that the first person I slept with would be someone I loved, not someone I found on Craigslist during an out of body experience and a loss of personality, like my body overriding my brain.

For me, sex without a meaningful connection just felt hollow, my orgasm a pyrrhic victory. I feel sad. I feel like I lost some part of my integrity. I never thought I’d be someone who would have anonymous sex, I always assumed that I was above that, that I wasn’t capable of it, and I was a tiny bit judgmental of people were. But now I’m one of them. And I don’t think I like it.

This article originally appeared on xoJane.