Finish: What a Sex Expert Cannot Do

by:  Caitlin Bergh 


New York City. For most, it’s the city of endless possibilities. For me, it’s the city where I was endlessly miserable. Going to college in New York was both a privilege and a tragedy. It was a privilege because #1) I got to go to college #2) New York City is, objectively, a cool place. But it was a tragedy because I was 18 years old, had no idea who I was or what I was into, and, as a result, I made a slew of very bad decisions.

It was also a tragedy because, as an 18 year old, there was virtually nothing that I was old enough to get into at night in Manhattan. It was like living in an amusement park, where all of the “must be this tall to ride” signs are just one or two inches above your head.

On my nineteenth birthday my friends wanted to take me somewhere they knew I would get in. It is a sad truth, but the places where 19-year-olds can get in at night (legally) are some of the MOST dangerous places out there.

Case in point: my friends took me to “nineteen & over night” at Webster Hall. Webster Hall is a seedy concert venue in mid-town where no self-respecting person would ever go. This nineteen and over night consisted of five floors of different dance music, hundreds of girls who, like me, had turned 19 that day, and hundreds of disgusting, creepy men, who had turned 19 a very long time ago.

If you’ll recall, at the time, I had no idea who I was or what I was into. Here were the facts: 1) I’d never dated a guy successfully 2) I’d never really been that interested in guys 3) I’d never had good sex with a guy 4) I’d never had an orgasm and 5) I had a really big crush on my best friend, who was a girl.

For some reason, even though I knew these facts, I just couldn’t do the math in my head. Not into guys PLUS crushes on girls EQUALS…. What? What did it equal? I was an English major.

Instead of realizing that I was obviously gay, I just got more and more frustrated about why I never had satisfying sexual experiences. I thought I just needed to try harder. Like giving 180% to every blowjob. Which I did. As it turns out, blow jobs are the one time where you do not want to try harder. You want to give a relaxed 75%. Otherwise, people get hurt. And this night at Webster Hall, this was the one place where you do not want to try harder. But I did. It was my birthday, and goddamnit, one of these sleazy middle-aged men was coming home with me.

At Webster Hall, my friends and I formed a circle of safety and started dancing. Guys twice our age were coming up to us and putting their dicks on our butts as we tried to dance. It was too gross. Then, something terrible happened. A tall, not too sleazy guy who was only 27 came over. He took my hand and started dancing with me, like a normal person.

I assessed the situation. He wasn’t too sleazy. He was around my age. I should probably make him my boyfriend. His name was Robert. He worked at T-mobile, which explained the blue tooth in his ear. He seemed pretty nice, but also really forward. He asked for my number right after he kissed me right after he bought me a drink. I gave it to him.

Robert texts me the next day and we agree to go out. But instead of going out, he just comes over to my dorm room and has sex with me. I’m not interested in him at all. It’s the strangest feeling. Why am I not into this? And if I’m not, why am I doing it? God it was terrible to be 19.

It’s not that he isn’t good. In fact, Robert turns out to be something of an expert at sex. I find out that he has six other girlfriends, and has a reputation in the tri-state area because all the ladies know he loves to eat pussy. He could eat it all day. What I didn’t know at the time was, so could I.

The one thing Robert never expected, as a sex expert who works at T-mobile and gave great head, was to meet me: a girl who he would do all of his famous sex tricks on, but a girl who he could never make have an orgasm. This frustrated him to no end.

He would always ask me, after literally hours of going down on me, “did you finish, did you finish?” I thought it was so weird that he called cumming “finishing.” What were we finishing? Being bored? I would always say, “I think so.” YOU THINK SO?! He would scream, and go back at it. But I never did. I never came. I was as confused as he was.

My friends thought I was cool for dating a sex expert, but I didn’t even like him. He was super annoying to talk to. He’d call me and talk my ear off for an hour. It was that damned blue-tooth. If you can’t take the energy to hold a FUCKING phone to your face, you have no business making a phone call. I knew I had to get away from this guy.

One day Robert came over and grabbed me and took my clothes off and started fucking me in front of my floor-length dorm room mirror. He bent me over a chair and told me to look in the mirror while he was fucking me. He thought it would help me be turned on to watch what we were doing. Quite the opposite. It made me want to die, even more than usual.

If you don’t like the person you are having sex with, watching yourself having sex with that person is probably the most traumatizing thing you can ever do. It becomes written in your memory and you can never escape the vision. The vision of him fucking you over a chair and telling you to watch it. You will have that memory forever.

I stood there, or hunched there, having consensual sex that somehow felt like rape. Even though I had consented to this, it wasn’t truly what I wanted to do. So instead of feeling like Robert was raping me, it actually felt like I was raping myself. Like I hated myself so much for the subconscious knowledge that I was gay, for the deep down feeling that I was actually not normal, that I was punishing myself by forcing my body into sex with people who didn’t even turn me on.

Confusion is flooding my mind as Robert fucks me over this chair. He tells me to look again, but I refuse. I let my hair fall in front of my face and just wonder if this will ever be over.

I start thinking about my best friend, one of the girls I have a crush on, just to pass the time. I think about the sunlight falling on her hair. The softness of her skin when she hugs me. The way her eyes light up when I walk in the room.

Robert pulls me out of my reverie. He grabs my hair, frustrated and says, “Look at me! I’m about to finish.” I brush the hair out of my eyes and look into his eyes in the mirror. They are filled with pleasure and passion that I have never felt. I just want to be with my friend right now. I just want to hold her. “Robert,” I say, right as he is cumming, “I think I might be gay.” In my own way, I was finally finished, too.


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