A Brief History Of Sexual Encounters

The first penis I ever saw was terrifying. Other boys since then have asked me how they “measure up” and I never know what to say because nothing I’ve seen since could possibly compare to this monster. It was enormous and purple and it made me feel inadequate because I knew that I wouldn’t be able to accommodate it in any of my orifices. But that was okay because I was fourteen and I’d decided to remain a virgin until the idea of being naked in front of another person didn’t make me feel physically ill.

Once you’re naked in front of someone they will know all of your secrets. I would like to know everyone’s secrets, and thus see all the people naked everywhere, but I don’t want them to know mine. If they saw me naked, they would know that I binge-ate at lunch. They would know that my inner thighs look and feel like bread dough. They would know the locations of all of my scars and suspicious moles. I’d prefer this information remain mine and mine alone.

The first time I had sex I kept my yellow sweater on the whole time. He was wearing an orange shirt. I’m glad that we coordinated, at least in one respect. We did it in my freshman-year dorm room. I kicked my roommates out so I could be deflowered in my top bunk. Other people had to sleep in that bed after me. That’s pretty funny.

After that I had this bad boyfriend who was tall and had a mustache and green eyes who took naked pictures of me that I didn’t want him to take, and who made me call him Daddy during sex. One time he videotaped himself hitting me with a belt.

That sucked, but I’m okay now.

After that, I “dated” this guy named Greg Thumb and ‘thumb’ turned out to be a surprisingly accurate descriptor for more than just two parts of his body. This was when I learned (the hard way) what you should say when boys ask you how they compare to everyone else size-wise: You lie. You just lie.

Greg Thumb also had these weird patches of shoulder hair. I thought it was funny to pet them, but he did not think that was funny.

And then I had a real boyfriend, and he was lovely. He was basically hairless. Also, he weighed less than me. He was 6 feet tall to my 5’4”, but he weighed about 5lbs less, and that did not make sense. I was voluntarily naked in front him, but I was very, very aware of this weight discrepancy.

I introduced him to my parents. He was my first (also only) ‘official’ boyfriend. He spent a lot of time on the computer. He treated me very well, but I think the Reddit community was a far more important part of his life than I was. Also, it annoyed him that I had bad days. He has fewer emotions than I do.

Once we did it at my grandma’s house.

After he dumped me, I was sad, and I didn’t eat very often, so I became very thin and beautiful, and when I realized that I now needed to wear a belt to hold up my size six pants, I decided it was time to start ‘getting out there again’ so I slept with one of the managers from my workplace. We didn’t do it at my workplace though, it was in my apartment. I can say that now because I don’t work there anymore, and also because I know he’s not on facebook.

Admittedly, that was a pretty bad idea, and had I been in my right mind (i.e. sober) I probably wouldn’t have done it. But it’s too late now, so I will decide not to be regretful. SECRET: I threw up that night, before he kissed me, and it was pink because I’d been drinking red wine, and tasted like Oreos because I’d been eating Oreos. I’m not sure that I brushed my teeth afterwards. I mentioned it once the kissing had started, but he said it was fine. I’m not sure which one of us is grosser.

A few weeks later, I kissed one of my best friends and realized that I loved him, and he realized that he would never love me, and it broke my heart. I don’t think I really understood that phrase before this happened. I suppose I could say more about this, but I would rather not.

So then I kissed most of the other boys that I worked with, because that is a logical response to heartbreak. And a girl too. That was weird. I’m super heterosexual. I ate and drank a lot and I gained a bunch of weight.

I dated this guy Jimmy for a while during the summertime, primarily because he had air conditioning. He was also nice though. I was really blobby, and Jimmy was more beautiful than I was. I commented on it once, probably made a joke about my doughy thighs, and he said “I mean, we all have bodies.” I think about that a lot. I feel bad that he liked me more than I liked him.

There was one boy I really liked for a minute. Or at least, I knew that I could have really liked him, given the time. He felt similarly passionate about macaroni & cheese. But then I moved to New York and he moved to LA, so it was doomed to fail. Sometimes I hope that we will both end up back in Boston, or maybe even some other mutual place, and then he can be my boyfriend for real. I know that probably won’t happen.

I kissed a really handsome boy and then he moved to China and persuaded me to “sext” with him, so I did, because it was kind of funny. I told him all kinds of stories about what I was wearing and doing, when really I was only ever wearing sweatpants and eating burritos. It was like a creative writing assignment. Then he abruptly stopped talking to me. At first I thought it was the time difference, but then after two weeks and an unflattering number of unanswered text messages, I realized it was not. I still don’t know what I wrote wrong.

I went on some dates with a guy who sent me really great messages on OkCupid and I was pumped about that (I’m always dazzled by impeccable syntax), but he decided that he’s still in love with his ex-girlfriend in Barcelona. We no longer go on dates, and are instead friends. This is totally fine. I’m serious.

It’s possible that I’m doing this all wrong. I recently occurred to me that I might actually die alone, but I would prefer that that not happen.

CONFESSION: Sometimes I like being naked. I like that feeling when you’ve been under the covers with someone and you’re overheated, so you fling back the blankets to feel the air on your skin. It’s refreshing. TC Mark

image – Shutterstock

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