Great Sex with My Best Friend

I met Sean when I was running a small magazine I created when I was 15 and not interested in my high school’s curriculum. Sean was a kid with big curly hair and braces at one of the nearby booths selling merchandise. He gave me a t-shirt or something and I gave him one of mine and we became sort of carnie high school sweethearts. We made out in the bleachers and in between some tour busses but it never went past that. Of all the people I met both summers, he was the one who stuck as the years passed. I started visiting him in Los Angeles, where he lived, as a means of getting out of my hometown in Canada where I felt like I was in brain jail and he was always there. He was often several hours late. But he’d be there.

I felt safe with him, our courtship had faded as soon as the tour had ended and he felt like my most trusted friend away from home. I began to see him as a brother-figure. He was protective of me and I loved his family. My mom loved him. Over time, the thought of anything ever happening between us felt like a weird Brady Bunch move. Over a period of several years, we would fall in and out of touch as we went about our lives, but we always circled back to check in and the welcome was always warm.

One day when we were both going through a breakup and sought comfort in one another. My boyfriend had been really hard on me about money, work and my body. It suddenly dawned on me that Sean had always looked at me like the sun shone out of my butt. I kept Sean at an arm’s distance because it felt good to have a friend I trusted and felt close to without sexualizing it. In my sudden realization at how good Sean made me feel when I talked to him, I actually saw him as a fully grown up adult, attractive male, and not the goofy teenager with braces and fluffy hair that I remembered (to be fair, both of us matched that description exactly) Somehow organically, we started talking about getting together.

Sean was coming through town, still working for the festival where we had met. I grew nervous and wondered if it would feel like making out with my brother. We talked through those feelings and decided we would deal with whatever happened. We had known each other long enough to know we loved each other as friends first. So I felt safe pulling the plug if it felt icky.

I met him at the festival and chatted with his co-workers while he finished up. We were so happy to see one another and I didn’t even think about the sexy part of it. I was just happy to see my friend and it was his first time in my town, so excitement bulldozed through any underlying anxiety. Once we made it to the cab over to my new place, it became clear that this very much did NOT feel like making out with a brother.