Full Disclosure: How I Lost My Virginity

Women, specifically the prospect of having sex with them, both terrified and fascinated me growing up. I would immediately volunteer myself into the friend zone because that always seemed easier than enduring the potential failure of romantic pursuits. It certainly didn’t help that I was a “dorky” kid, who was called a fag pretty regularly and wasn’t much good at sports (except for football, which I know, weird).

In high school I believed that if I embraced my individualism and had confidence in not conforming, I would be accepted and appreciated for who I was, because I was an idiot. So it didn’t really help when I made the transition from awkward gangly kid with acne who wore puka shell necklaces to awkward gangly kid with acne who wore a trenchcoat and kept saying this (I DIDN’T know Kung Fu, but I DID see Crouching Tiger, Hidden Dragon in theaters, TWICE). Maybe I just thought  by wearing a trenchcoat I could scare girls into fucking me.

As I’ve mentioned before, sex was a scary thing for a variety of reasons. Women were a very mysterious thing. I didn’t even know until I accidentally stumbled upon pornography on the first tv I bought that women’s vaginas were underneath them (diaper commercials that touted “leak protection in the front for boys, in the back for girls” always confused and frightened me. That poor girl is going to get piss everywhere!). There was a great debate in middle school amongst my friends about how many “holes” girls had. Before the advent of streaming online pornography, we would specifically seek out close-up pictures of vaginas, intent on settling the hole debate once and for all, which went something like this:

2-hole camp: This is the camp I belonged to, which I still maintain it’s a pretty reasonable one. The idea is that women have an asshole and a vagina – from which they birth and urinate. After all, men urinate from their sex organ, so it only stood to reason women did the same. Plus, even with all the close-up encounters I’ve actually had with women to date, I’ve still never expressly seen the pee-hole.

3-hole camp: As it would turn out, the correct one. This of course includes the asshole, the vagina, and the pee-hole. Tip of my hat to the precocious young lads who were in this camp.

4-hole camp: Here you have the asshole, the vagina hole, the pee-hole, and the clit-hole, naturally.

Then you have my friend Evan, who belonged exclusively to the 1-hole camp. Evan believed that women shat, birthed, and pissed all out of the same hole. If that wasn’t the case, he’d argue, why do women sit when they pee? Considering we all thought the vagina was in front, it was reasonably sound logic.

As online pornography became more and more pervasive (really AOL, what am I supposed to do with 30 hours?), I became more and more self-conscious about everything from size to stamina. How could that guy POSSIBLY be fucking her tits like that for 10 straight minutes? I’d already whittled my penis like a prison shiv by that point. I remember one time I was watching porn and I came so ridiculously early, that I literally started laughing out loud at the absurdity of the situation. When I looked to see how much time had elapsed in the video, it read :04 seconds.

But once I made it to college, everything changed. Not because sex was so much more readily available (I’m actually the first guy in history to turn down his high school girlfriend’s offer to have sex), but because I started to feel valued for the things I really cared about. The only reason I wore a trenchcoat (and later suits and pajamas) in high school was to create a visual flag that I didn’t feel emotionally or intellectually connected to my peers; if people could see that I didn’t look the same on the outside, then they would understand I didn’t feel the same on the inside. But at Berkeley, there were communities for everyone. Sure there were still assholes and idiots, and people who cared about conforming. But conforming at Berkeley meant trying to take the most upper-division courses, joining the most social causes, being the most naked person in your co-op. And at the end of the day, if you didn’t fit in with a particular social group, amongst the 40,000 undergrads you could easily find a group in which you did.

Me as a 6’1, 135lb, pretty fly for a white guy high school freshmen.

When I started to be valued for the very things I valued, I experienced something I never had in my entire life: confidence.

I never thought I’d lose my virginity the way I did. Christian notions of a virgin wedding aside, I knew that when I lost my virginity, it’d be to a woman I was in a longterm relationship with. We would have long conversations, write each other poetry, and eventually on a rainy December night with the Postal Service or perhaps Bright Eyes playing just above the headboard and our half-eaten dinner plates, everything would become magic.

Except that’s not at all how it happened. It was October 16, 2004. It’s a convenient date because it serves as an anniversary for both the loss of my virginity and my sister’s birth. It was for this reason that my family was gathered in celebration of my sister’s 25th at her condo in the East Bay. My cousin was in attendance that evening, and she had decided to bring an old high school friend with her as a guest. This friend’s name was Sonia, and she had a Wisconsin accent that could grate cheese. She stood about 5’7 and weighed no more than 105 lbs, and we’ll just say she was very top-heavy.

Of course virginal me (and pretty much everyone else in the room) couldn’t help but notice what Sonja’s low-cut and high-riding dress was proudly displaying, but I pretty much dismissed it all since a girl like that would have no interest in me.

And then she said one of the strangest things I’ve ever heard: Li’l Abner is my favorite musical.

Now you have to understand. Li’l Abner is the worst musical of all time. The only way it’s ever been made worse is when I was somehow cast at the titular lead in high school, singing all sorts of songs that had no business being sung, especially by someone who couldn’t sing. So when Sonia said it was her favorite after apparently not having any idea that I was even in it, I knew the night was about to get weird.

As she continued to talk to me, she persisted to put her hand on my knee and squeeze my thighs. She mentioned that she had just broken up with her boyfriend and was looking for someone to “show [her] a good time”.  Later she asked to come back to Berkeley with me because she was looking to party.

“What kind of party,” I asked her. “There’s all sorts – co-op parties, frat parties.”
“I’m sure as long as we’re together, it’ll be a party,” she responded.

I was having a giant boner party at the time.

When we get to my co-op, immediately she starts drinking (something that even as a sophomore in college I still had yet to do). When I ask her how she plans on driving home, she tells me that she’ll just stay with me. I had never had a girl hit on me so blatantly and I didn’t know what to do with it.

As the night progressed, she grew drunker and drunker and I grew more and more anxious. After attending the infamous CZ Stripper Party, where college co-eds can grease their first pole in an amateur contest, we headed back to my place. We settled onto the living room couch, because I lived in a double and my roommate was home, and it’d be a couple years before I’d engage in roommate sex. Plus if things got awkward I figured I could just offer her a half-eaten Chik Patty from one of the couch cushions.

After what seemed like hours of spooning and playing the “who’s going to make the first move, oh wait if not me than no one” game, I decided to move my hand up her thigh. She abruptly stopped me. “I’m a lady. I’m not going to let you do that stuff when you haven’t even kissed me,” she said. Ashamed at my novice mistake, I began by giving her a soft peck on her forehead, at which point she immediately shuffled down the couch and began to go down on me, like a lady.

No sooner had I remembered that my cousin had been accompanying us through the evening and was in the adjacent room than Sonja sat atop me, and I realized at that moment we were engaged in the act of sex. You see, the entire time it turns out that Sonia was not wearing panties, and I got a hop-on.

The feeling was incredible. It was just like every movie about fucking a pie I had ever seen. It was at this point that Sonia informed me, “You’re supposed to move in and out, don’t cha know.” I’M TRYING TO SAVOR THE MOMENT my thoughts screamed back at her.

And as I followed her behest, I could no longer enjoy what was happening. My mind was flooded with a new mantra: please don’t come, please don’t come, oh god please don’t come. 15 seconds had elapsed, and I realized I was losing this battle. I stopped. I try for another 15 seconds. Then I had a brilliant idea.

“I need to run to the bathroom really fast,” I told her. I’ll empty the chamber, return, and everything will be brilliant.

I went into one of my house’s main floor bathrooms, shared by some 64 different people, and proceed to have one of the most intense orgasms of my life. So much so, that my ejaculate literally BREAKS THROUGH the eight sheets of toilet paper I had wadded up to contain it, splattering all over the wall like a Jackson Pollock. But I’m not done. The orgasm was still happening. 5 seconds, 6 seconds, 7 seconds, and on. I decided the effort to contain the mess is fruitless and I let it fly like an out of control firehose. Ten seconds had elapsed and I braced myself as I surveyed the damage I’d done. At this point I’d probably been gone five minutes, but I couldn’t leave the bathroom in the condition it was in (though believe me it crossed my mind). I do a perfunctory wipe job and run back out to the living room, where my proper deflowering would continue.

Except it doesn’t. Sonia has her clothes back on, and is asleep on the couch. I find out later that she had just assumed I came already in that first 30 seconds, and wasn’t exactly itching for a second go-round with me.

There was no love. There was no Ben Gibbard poetry to speak of, and I never saw Sonia again. I had always attached so much meaning to sex, but for the first time I thought maybe sex is just what you make of it. You can have sex with five different people and have that mean five different things, each significant or not in their own way.

I’d go on to have sex with many different people of all shapes, sizes, and genders. And while they all meant different things to me, I remember all of them and each truly holds value to me, whether we were together 30 second or 30 months.

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FREE porn pick of the week (NSFW): Taboo 2 (1982 vintage, before obscenity laws discouraged porn producers from explicitly building things like incest into their plot lines)

Full Disclosure podcast Episode 44: Dating Coach Marni Kinrys
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