Probably because my first time (with a guy) was the least sexy encounter ever. And was also kind of multiple encounters that eventually led up to a successful complete “coitus." 

My first time with a girl, before I get into this story of the losing of my "virginity,” was with Elle. We did it in her SUV and it was pouring rain all around us outside. I was nervous the entire time. We fogged up the windows. I wasn’t out to any of my roommates, so when I came home and they asked where I’d been, I lied and said I went on a walk and had gotten stuck out in the rain.

Sex with a guy and the whole metaphorical “cherry popping” came later. I say metaphorical because I didn’t bleed (which is normal, by the way!!) It was significantly less smooth than with a girl, mostly because a lot of it was coordinating me being wet with him being hard and balancing our respective nerves about the whole thing. 

The first time we kind of did it, I forgot I had an appointment that day. So, he’d thrust into me once and my phone started ringing with the reminder for the appointment. And so I really awkwardly climbed off of him and was like, “uh sorry, sorry, sorry.” On the way there, I had this really awkward sort of phantom penis feeling inside of me, probably because I’d never felt so full before. So, I was sitting through a doctor’s appointment with this weird empty fullness – if that makes any sense – in my nether regions and mentally debating whether or not I could count that as losing my virginity. And how virginity is a construct anyway. And how I was 500% glad I didn’t save this bizarre experience for a wedding night like a bunch of my friends at the time were planning to.

A few days later, at about 10 in the morning, we tried again. In retrospect, it was probably absolutely horrible. But, at the time, we were just kind of thrilled we’d managed it. I was on top, a position I now really don’t enjoy all that much, but he kept bucking his hips up to meet me which felt great. If you can believe it, I actually came first and it lasted a fairly longish amount of time. It was his first time, too.

And, yes, it was somebody that I’ve mentioned on here before.