Back in the days when I actually wore lingerie and bathed on a regular basis, I was a burgeoning sex kitten. I had a belly button ring and a list of makeout spots. I was a self-titled "good time girl." I liked being kinda slutty - it was a badge I wore with pride.
I wasn't unusual. Of the hundreds of people in my graduating class, I knew only a handful of virgins. Everybody did everybody. Sex wasn't so much a rite of passage as an unwritten rule. We were young, we drank Popov vodka, we went skinny-dipping. My group of friends was so sexually voracious (and bored) that many of us ending up hooking up with each other. Most of it happened in my basement (sorry Mom and Dad). And most of it was messy. I'll never forget certain incidents involving a stained t-shirt and a midnight romp down my street clad only in boxer shirts.
I don't regret any of it. My sexual exploration as a teen was completely natural and entirely pivotal to my development. I wouldn't be as awesome as I am now had I not learned a few things along the way. Among my greatest learning experiences were the two virginities I destroyed.
The first one was an accident. I didn't actually find out about it until a good three years later.
At age 17, in the middle of summer, and in the midst of a dry spell, I proposed what I liked to call a "business arrangement" with a friend.
This friend was more than a friend. He stuck his tongue in my mouth when I was 13. We spent our entire eighth grade Washington, D.C. trip with his hand surreptitiously down my pants. We fooled around everywhere, and we had a lot of firsts. We parted after middle school, when he was sent to boarding school and I went to a public high school.
We stayed in touch and went for friendly car rides on some weekends and holidays. I hadn't viewed him as a potential sex partner - I was young and had lost my virginity to my high school sweetheart just a year prior. He was back at his parents' for the summer. He was kind and gentle and nothing like me. He liked lacrosse and wore khakis. I had come out as bisexual and listened to Alkaline Trio. But goddamn I was desperate.
I hadn't intended on making it with a virgin. He had told me previously that he met a girl at school named Kate who had popped his intangible cherry, but that it had gone kaput prior to the end of the school year. Finding myself adrift in a sea of losers, he seemed like the perfect option. I gathered my courage and sent him an instant message. I proposed an agreement - hookups whenever one of us felt like it, with no strings attached. It was perhaps my most brilliantly engineered relationship to date. He eagerly agreed, and I made a date for our first rendezvous.
I showed up at his parents' whitewashed stately colonial house around 1 pm. He had the kind of parents who had money but you really didn't know how; they drove brand-new Volvos and played tennis and were never home. He came to the door and planted a sloppy, wet kiss on me. It didn't get much better from there.
We hurriedly made our way upstairs and started getting down to business. It didn't take long before I started wondering why he was so... bad. No rhythm, no natural sense of movement. I got on top and remember staring at the sports-themed border in his still-pristine childhood bedroom, and all I could think about was... balls. I worked my magic and expected results, so we could wrap it up. I was surprised at his longevity. He suggested we go take a shower.
Now this should have been it. I should have known that any man who would get in the shower wearing a condom and proceed to poke around my behind was definitely green when it comes to intercourse. He was too excited and all too eager to push the boundaries of our interaction. I yelped in pain and he backed off. He left me to finish my shower and was ready and waiting afterward with a new rubber. I admired his persistence and obliged, but I was weary of any future hookups. I held out for a month before getting back in the saddle.
We went on to have a lot of good times together, and I let the inelegance of our first time together slip my mind entirely. Several years after everything romantic or sexual fizzled out, on the heels of a very casual conversation, he dropped the bomb that our fateful afternoon was his first time. Part of me was horrified that he hadn't mentioned it sooner. The bigger part of me was relieved. At least he had an excuse for why it was so uncomfortable. My ass didn't.
