Last week, when I told you about The List, I mentioned the first person I'd slept with, a guy I call Skater Boy.
When SB and I met in high school, he sat across from me in psychology class. Actually, he rarely sat there because he usually got kicked out for being a smart ass. Since I’m a bit of a smart ass myself (not sure if you’ve picked up on that) but was also a well-behaved student, I was intrigued by his ability to speak his mind, even when our teacher threatened him with detention. I’m pretty sure SB might have even sworn at him once and I’m not gonna lie, that was hot.
By this point, I was pretty much your stereotypical cheerleader: blonde, blue-eyed, and sporting a very short (but school-sanctioned) skirt on Fridays. He, on the other hand, had shaggy red hair and wore tie-dyed t-shirts and hemp necklaces. But despite our outward differences, we seemed to get along, proving what’s inside a person is just as important to the attraction as the outside features. Though, to be fair, I thought he was totally cute, even if he didn’t play football.
We’d make eyes at each other in class (when he was actually there) but neither one of us seemed able to believe that the other was interested. So when he finally asked me for my number, the anticipation had built up to the point that I was actually shaking as I wrote it down.
Our initial phone conversations lasted hours, and it became clear we had stumbled upon something special. On our first date, he took me to China Town for dinner at a restaurant called The Mandar-Inn, but somehow got us so lost that we ended up in the middle of Cabrini Green. I could tell he was embarrassed, but he tried to laugh it off. In fact, we both ended up laughing about it and we still do now when we occasionally keep in touch.
When we finally made it to the restaurant that night, and we couldn’t stop holding hands over the table or even break eye contact, something inside of me somehow knew he was going to be the one I gave my virginity to.
It didn’t happen that night, of course (keep in mind that’s when sex was still a really big deal to me) rather we waited several more months until I was ready. That was what he wanted. He had already gotten his whole “virginity thing” out of the way, and he used his experiences to bring out my sexual side. He patiently showed me the merits of receiving pleasure, when in the past I had really only given it.
When he went on a trip to New Mexico he brought me back a most unusual souvenir. It was a vibrator. At first I was disappointed, because I had asked for a dreamcatcher, and I wasn’t sure if I wanted to be the only 17-year-old I knew with her very own sex toy. Though I was skeptical, when we finally tried it out, it didn’t take long for me to become a true believer. Obviously. And once I became accustomed to the idea of penetration, we decided it was time to go all the way.
I couldn’t have asked for a sweeter experience. His parents were out of town so I lied to my own and said I was staying at a girlfriend's. When he got home from work that night, he made me dinner, we had a glass of wine, and that’s when I got nervous. But he cared about me so much that he wanted to make my first time as special and painless as possible. We went to his bedroom, where there were candles lit and a Dave Matthews CD quietly playing in the background (shut up, it was 1998.) He kissed me softly and things progressed slowly until the moment itself, which to be perfectly honest, did not feel that great. Fortunately, it didn’t last very long (hey even an experienced guy can get a little too excited sometimes) and when it ended I remember thinking to myself “I’m a woman now.” It sounds stupid, but that’s how I felt. Then, as soon as he was ready, we tried again, only this time it was much better. All of our fooling around, plus the help of our battery-operated friend, had taught my body how to build to a climax. So the very second time I had intercourse, I had an orgasm. And that, my friends, is why I love sex.
I bet with the colorful history I’ve alluded to, you were probably expecting a gangbang in Cancun with an entire Mariachi Band. Not so much. Believe me, I’ve done some crazy things in my day, but I don’t tend to remember the little details about them the way I do about that night. I’m probably better off that way, come to think of it. I’m not kidding, I’ve done some craaaazy shit.
But to have that “first time” story, I feel lucky. For so many girls I know, it took years for them to enjoy sex. I was blessed to have a partner who wouldn’t stand for anything less than mutual satisfaction. At the same time, I suppose I was cursed by this, because learning to appreciate sex so early probably has something to do with why I’ve had so much of it since. Over the years, however, my motivations have certainly changed, and because of that I haven’t had nearly enough sex that meant as much to me as it did that night. But as I look forward to ending my celibacy, I can’t help but wax sentimental on how nice it would be to feel that way again.
So I owe Skater Boy a thank you for making my first experience one that I never want to forget. If it weren’t for him, it might have been years before I learned how to make sex work for me. Then again, if it weren’t for him, I might have spent every night at home studying instead of fucking, eventually curing cancer or winning a Nobel Peace Prize. Nevertheless, he was both a wonderful teacher and boyfriend. He introduced me to romance, vibrators and orgasms. And for that, he deserves his own Nobel Prize...if only they have one for sexual achievement.