I was a frustrated virgin. I had gone to college without having had penetrative sex and  decided that not only did it mean I was undesirable but that there was something wrong with me.  That was affirmed by the first person I hooked up with. When I told him I was a virgin, he  refused to have sex with me for fear that I would become attached. I was hormonal and, in truth,  not attached to him at all. I still don’t believe I would have become attached to anyone in that  position. A desperation within me led me not to want it to be particularly special or even  romantic.  

This was perhaps the start of me feeling so different than the women I was around  growing up that I went to the internet for answers. I had been made to feel like a freak for my sex  drive and my masturbation practice. And this was by other women! I would realize that as  judgemental and dismissive as it seemed, it came from a place of disconnect and shame with  themselves.  

This meant I had a huge problem. I had been humiliated by this person. I knew it might  happen again if I told the truth. And so I resolved to lie. That meant that I could either grimace  and hide the pain that I was told was a hallmark of first-time penetrative sex, or I could get  creative. I’m very fortunate to have grown up when I could use the internet to find Betty Dodson.  Her website and writing are where I divined the best ideas I had had in my 19 years on Planet  Earth. I would penetrate myself first. 

I was gifted a lime green, thin vibrator that I am almost positive was a novelty toy— probably not designed to be used on a human being. It was purchased at Spencer’s for cheaper  than I’d like to remember. I had used it barely. The vibrations were dull, and the tip was pointed.  It was less than ideal for the clitoral stimulation I’d grown fond of since adolescence. But it  would be perfect for my goal. I had limited means when I was home from college. I know I used  lube, but I shudder to think what kind of lube I used. It was likely water-based, sticky, and  smelled vaguely of plastic.  

At first, with no warm-up, wanting to be over and done with it all, penetrating myself  with that cheap vibrator hurt a bit. I would masturbate to orgasm a few times and then found it  abundantly easier. I would practice while I watched a movie or TV. Ever since I was a little girl, I  would be frustrated if I couldn’t complete a task or learn something immediately. Masturbation  and orgasms came easy to me from childhood; I wanted to nail penetration. Weirdly, I didn’t feel  ashamed or embarrassed about this at the time. And the more I’ve aged, the more rad I think it is.  

I went back to college for the spring semester, having successfully incorporated  penetration into my masturbation routine. I even bought a cheap glass dildo that I was fond of. I  turned 20 in February and was miserable. I carry a bit of shame and regret about that; after all, I  was my best lover at 20, and I knew from bits and pieces I heard growing up that that is a rare  and beautiful thing. Perhaps that is changing with each generation.  

Everything changed one weekend night. I was with my best friend Zach, and we decided  to go to a college party. We walked uphill to the apartments where the upper-level students lived.  It was treacherous to go on foot. Zach is my most audacious and impulsive friend; his part in this 

story is the romance. He’s gay, and we’ve adored each other since we met. Many of my  soulmates are my friends, especially if they have a similar obscure humor to mine.  At this particular party, I locked eyes with this beautiful man who had been in my  Shakespeare class. He’s everything I adore about men to this day. Big, burly, hairy, and, dare I  say it, simple. I’m not sure how it all transpired. I’m not a natural seductress. But somehow, we  were making out in the bathroom and planning to walk to his apartment. To date, I’ve never been  in a more disgusting apartment. Generations of the outdoor primal pursuits club had handed it  down, and it was in disrepair. None of this mattered.  

The whole experience was rather empowering. I hadn’t dated this person. He didn’t buy  me a fancy dinner. None of that made sense to me in this context. I wanted to have penetrative  sex. The sex was the event. The few people I chose to tell did not receive this opinion well until I  met Zach. Is it weird to think of my friends as the loves of my life? Here I was, stripping naked  with a gorgeous man, and I felt nothing but pleasure. There was no anxiety about pain. And I  refused to tell him I was a virgin. After all, it was only a minor lie. I had penetrated myself. Can  you take your virginity? Is virginity even something that is taken?  

When he penetrated me, I was more aroused probably than I’d ever been. There was no  pain at all. I didn’t orgasm; that would come later with partners. Unfortunately, that is the gamble  you take as a woman engaging in hook-up sex. That’s not to say it was terrible. It’s an experience  I look back on fondly. And if I have a daughter, I will openly encourage her to do the same. By  injecting the whole experience with romance and having it be rather painful and traumatic, it  sends a strong signal to our girls. It’s the first message we get as women that our pleasure does 

not matter. Romance matters! But sex is painful, dangerous, and dirty unless you are in love with  the person. And then you’re lucky that it’s just painful.  

As I was lying there in that horrifying college apartment, I heard voices outside the  window. It was Zach and my other friends walking home from the party. It was as if they were  there with me, cheering me on. When you penetrate yourself, you stand firmly in your power.  And nobody can take that away from you. 

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