This One Time, When I Was a Virgin …

Editor’s note: This post serves as, hopefully, the first in a series about losing your virginity. This series was inspired by this Rookie Mag post. We hope it offers a glimpse at the experience of losing your virginity and all the complexities that come along with that. These pieces have hints of the explicit and are not for the easily offended.

When I was in high school, I hung out with a pretty sheltered group of kids. We were the theatre and band kids, and not the sexually active kind. I was a lot more promiscuous than I ever told any of them. When asked the question “Will you wait until you are married to have sex?” I, like the realist I’ve always been, said, “Gosh, that sounds like a lovely and romantic thing to do, but I don’t think it’s a realistic expectation to put on myself.” This was appalling to most of the people I hung out with because abstinence-only education taught my friends and me that sex before marriage would lead to an inevitable STD upon first penetration.

The other thing that separated me from my friends and their sexual journeys was this huge secret I was keeping. I was feeling the feels for my best friend, and, oh yeah, she was a lady. It was one more complication on top of all the talk of boyfriends and losing your virginity. The desire I felt strongest, and still feel today, was this yearning for a connection with someone. I wanted so badly to fit in with that image of being in high school with a boyfriend and exploring bodies in an innocent high school way, but that wasn’t meant to be my story.

In my pursuit of this partner, I took to the only social media outlet available to me as a senior in high school: MySpace. The ultimate resource for everything from booty calls to all those STDs I mentioned earlier. I went out with about a dozen guys, trying to explore my sexuality and understand why I always felt so different from my female peers. I had some pretty terrible dates and admittedly put myself in some dangerous situations because meeting people on the internet in 2005 was not ideal. This is where I met the guy who would take my virginity.

His name was Oliver, which was so charming to me, and he was a red-headed scrawny college guy. We had chatted for a few weeks until he was in town from his fabulous college life to visit with his parents, so we seized the opportunity to meet in person for the first time.

I don’t recall going into this date with the intention of losing my virginity, but that’s how it went. We met in the Safeway parking lot because I like to keep things classy. He went in to buy us alcohol while I waited in the car, which was so cool to my 18-year-old self. He came out with the only thing I could suggest he grab: Smirnoff Ice, the high schoolers’ go-to adult beverage. Then we drove out to the middle of the desert for some privacy, lively banter, and booze.

Now, I know what you are thinking: “Jess. Are you telling me that you drove out to the desert in the middle of the night with a stranger and a six pack of Smirnoff Ice on purpose? Did that not strike you as a potentially bad thing to do?” Frankly, no. It sounded like a dangerous thing to do, but I was looking for that experience.

What began in that Safeway parking lot was hardly the safest way to go about losing my virginity, but Oliver was really a nice guy. He didn’t come with expectations. Up until that point, I’d never had more than a glass of wine at my cousin’s wedding, so three Smirnoff Ices put me well over my limit. We talked in the front seat of my car, and he suggested we move to the back. I knew what that meant, and recall feeling ready for it. There wasn’t much to talk about once we positioned ourselves in the backseat of my car. I don’t think there was a discussion of the status of my virginity, but by the end of the night, it was unquestionably out the window of the claustrophobic backseat of my Honda Civic.

Looking back on this experience, I can honestly say I have no regrets. The loss of that virginity felt inconsequential compared to the first time I slept with a woman. It was a test, an answer to some questions. So, why wouldn’t I just consider the first time I slept with a woman to be my actual “first time?”

First times are a hard thing to decipher when you are challenging the norms of sexuallity. I may technically have two sets of first times, but the actual first time was the first time I took my clothes off in front of someone else. It was the first time someone attempted to please me. It was the first time I made myself vulnerable sexually to another person. Regardless of his gender, this was my “first time,” and I’ll always remember it as such.


2 thoughts on “This One Time, When I Was a Virgin …

  1. I really tend to agree with you. As much as society today (IMO) cheapens sex, makes it all about momentary pleasure, and perpetuates the idea that it’s the progressive decision to have lots of partners, my own experience has brought me to conclusion that is similar to yours, Jess. Sex is oh so fun, and I spent the better part of high school and college experimenting with several guys. Sometimes it was good, sometimes it was bad, and occasionally it was terrible. Never, ever, was it fulfilling. Even my first time with my fiance, while fantastic physically, was lackluster emotionally. It wasn’t until, as Jess put it, we made ourselves “vulnerable sexually” that it was really satisfying for me. While I technically lost my virginity when I was 14, My first time was a little over a year ago with the guy I’m marrying in 8 months.

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