Children of the Boss

Chapter 5: Gabriel

August 1st

At Dean's birthday party that had really just turned into a casual party in the basement, I sat with Alyssa and Tamir on the couches. We were talking with our friends from choir but I was also messaging someone. Cody was 20, almost 21. He was going to be a junior in college. I was going to be a sophomore in high school. Still, he was in town for the summer and we matched on Tinder. We talked for a couple of weeks and then I invited him to Dean's birthday party.

I knew I was gay when I was in fourth or fifth grade. Dad tried not to act excited when I told him and Pop, but he was actually really excited to have a gay son. I was glad I had gay parents. Dad told me a lot about his experience being gay and what it was like. It was just great being able to really relate to your parents. They didn't make me feel bad for being feminine and they said if I didn't want to call myself a twink I didn't have to (even though I kind of was). 

Alyssa was the first person I told. We were both in the same grade and best friends ever since we were kids. Then I told Dean. Then Dad and Pop, and soon everyone else. I had my first kiss with a guy when I was thirteen, nothing too much. We were at a summer camp for LGBTQ kids and just kissed one day. I kissed a lot of guys after that. That was a little over two years ago. 

I shouldn't have invited Cody, but he was really attractive and I remember having a crush on him in sixth grade. He was a sophomore in high school when I was in sixth grade. Alyssa and I would go to football and basketball games for the high schoolers when we were in middle school. Thinking about it now, it was kind of disturbing how many of the high school guys would flirt with Alyssa and I when were only twelve and thirteen. A guy who was seventeen once asked me if I wanted to give him a blow job. I was literally only twelve and just got out of sixth grade. I said no of course, and when one guy wouldn't stop messaging Alyssa to come over to his place we stopped going to the games.

I should've known better than to be interested in a guy who was in college. I mean, he was going to be a junior and there were thousands of people at NYU. Millions of people in NYC. Our town had about 12,000 people in it and yet he chose me, a fifteen-year-old sophomore to talk with.

I met him outside. "Hey," I greeted, smiling at him. He was really attractive.

"Hey babe," he said, which made me cringe inwardly. He kissed me too. 

A few minutes later we were in my room making out on my bed. Making out I could totally do. I was a great kisser and liked kissing. Then he took off his shirt and took off mine without asking. I was a tiny guy, which a lot of times I didn't mind because I liked being cute and being tiny helped with wanting to be feminine. At that moment, I realized just how immature my body was compared to his. He had some muscle, some fat, blemishes, hair. I was still pretty hairless and not much muscle at all. He pulled a condom from his back pocket, and I though how bad could it be?

It was awful. The kissing wasn't bad and his hand on me wasn't bad. The penetration hurt but it wasn't unbearable. It was just everything all at once. He was ugly and sweaty and smelled bad and it was all about him. I'm glad I didn't see his face. The sad thing is I knew for a lot of gay men the first time wasn't great. In fact, I knew for a lot of gay men they would have sex with older men often. I remember watching a video with some of my favorite drag queens and they all talked about how their first time was. A lot of them were teenagers, like me, and had sex with older guys, like Cody. One of them said they had a nice time though, with a man well into his thirties. I guess I was always hoping for that instead of the other scenarios.