IT HAPPENED TO ME: The Guy I Lost My Virginity To Had No Idea It Was My First Time

At 19, I hatched a plan to lose my virginity to a guy I liked without him having any idea.
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At 19, I hatched a plan to lose my virginity to a guy I liked without him having any idea.

When I was 13, I saw the movie "Cruel Intentions" twice in cinemas. I liked it because it actually dealt with teen sexuality, a new topic for me. 

The kids in question were only a few years older than I was, and yet they knew all sorts of exciting words and seemed to have experimented with every sex act I could think of (albeit, my knowledge on this topic was not particularly expansive at the time).

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My favourite character in Cruel Intentions was Sarah Michelle Gellar’s Kathryn. Kathryn slept with whomever she wanted, made out with girls in public without any homophobic reservations, and wore incredibly sexy lingerie. She was definitely the most sex-positive character I had ever seen on screen. Sadly, however, Kathryn was also the villain.

The hero was Annette, a sweet girl-next-door played by Reese Witherspoon. Unlike Kathryn, Annette believed that you should only have sex when you were in love. She thought you should wait for “the one.” And Kathryn did just that. 

The act itself happened in missionary, with lots of kissing and the song “Colourblind” playing in the background. Halfway through their coitus, Sebastien even stopped to ask Annette if she is all right. It was at that moment when I developed a fear of losing my virginity.

I was interested in sex, for sure, but I hated the societal baggage that came along with it. I didn’t want the pressure of having to wait for the “right person,” find the “right moment” and make sure we were in “the right place.” 

I didn’t judge people who did crave these things, of course, but I resented the fact that the dominant societal discourse suggested it wasn’t normal to see things any other way. I wanted sex, but I didn’t want it to have to be about love. Most of all, however, I resented the symbolic claim someone would have over me if they became “my first.”

For some reason in our society, who your first lover is matters infinitely more than your second, third, or fifty-first is. Perpetuated by heternormative stories of fairy-tale-like sexual initiations, there is this myth that you, as a young woman, should give the question of who your “first” will be more consideration than practically anything else. In fact, probably more consideration than whether to go to university, and which school you should choose.

As I hit my late teens, I became more and more convinced that my sexuality was my own. I didn’t want to lose it at prom night in a king-sized bed like kids did on American television series (plus, I was a Canadian whose all-girls independent school hosted an annual winter formal, not a prom). 

I didn’t want to lose my virginity to someone at all, in fact. I didn’t buy into the idea that “my first” was someone who had to be eternally important to me – no matter what they did later – just because they put their member inside me before anyone else.

I wanted to resist the idea perpetuated by the media that your first time sets the stage for the rest of your life. Sure, it’s important that you feel comfortable when you do it. It’s important you can consent to it and only do it when you want to, but why does it have to matter more than all the other times you have sex subsequently?

So, at the age of 19, I hatched a plan to lose my virginity to a guy I liked without him having any idea our sexual shenanigans would be my, ahem, maiden voyage. At the time, I had been dating a cute guy named Travis for three months. He was a med student at the university where I was an undergraduate major in Gender Studies. It was winter break and I was attending a conference in Calgary, where his family conveniently happened to live. I decided this was the perfect opportunity to lose my virginity.

I liked Travis, but I didn’t want him to think I had “waited for him,” or that I thought he was “The One.” I felt that was a lot of pressure to put on our fledgling relationship. 

What’s more, I didn’t know him well enough to know if he was special. And, as an inexperienced 19 year-old, I wasn’t even sure I was capable of divining whether someone could be “the one.” 

But, I decided that didn’t mean I should deprive myself of sex for years more to come. I did know I was ready for sexual pleasure, even if I wasn’t ready to say Travis was someone with whom I could see myself buying a dog and sharing a mortgage.

In preparation for our big sexual encounter, I decided I should probably get rid of my hymen. I did it myself. Lying in bed, I punctured what Shakespeare would have called my “maidenhead” with a pen. I do not advocate this crude method of getting rid of one’s hymen. It definitely wasn’t sterile and I’m surprise I didn’t emerge with some sort of infection; however, I have to admit the whole process did work out wonderfully for me.

Travis and I met up in downtown Calgary one night after I was done with the conference. As luck would have it, his parents were away for the weekend, skiing in Banff. After dinner and drinks, we went back to his place ostensibly to watch a movie. Of course, we never watched anything other than each other undress.

I’m not going to lie, there was one moment when I came close to admitting this was my first time. Unsure if my antics with a ballpoint pen had completely done the trick, I was worried about pain and bleeding. As he looked into my eyes, Travis clearly picked up on this stress, as he was about to enter me.

Taking his face in my hands, he asked me softly, “Are you OK? You seem really nervous?” I thought for a second. I could tell him I was a virgin, I could tell him the whole thing with just thing little words. It would be so easy, the work of a moment.

“I’m completely fine,” I replied.

And with that, the intercourse began. I had achieved my goal of unceremoniously losing my virginity.

Almost 10 years later, I do not regret this decision. Travis was a nice guy, but I soon discovered we had little in common and we broke up. I don’t speak to him anyone, though he is a Facebook friend. It’s a relief not to have to pretend to think he’s special because he was my first.

The truth is, the sex I had with Travis was the first sex I had, but it wasn’t particularly formative. The first time I did doggy style, gave someone a hand job in public, and the first time I had really loud sex, all left more profound marks on my psyche and my sexuality.

In the end, my decision to lose my virginity without telling my lover he was my first was a really good one for me. I’d do it again if I could.