I Thought Threesomes Were Supposed To Be Fun.

Threesomes are supposed to be fun, right? That’s what I thought, way back when. The names have been changed for obvious reasons.

When I was 18, I took part in my first and to date, only threesome. As a highly sexual and porn obsessed young adult, I’d definitely fantasized about being with two guys at once. The idea of three bodies writhing around together an enjoying each other sounded so hot. So you can imagine my reaction when I found out that I’d actually get to take part in my very first threesome.

I’d been seeing Joe casually for about 6 or 7 months. Joe was in his late 40s. He’d been married, divorced and had adult children. We’d started talking in a chat room and quickly met for dinner and ended up getting down in a motel room on our first date. We ended up hitting it off though and found that we really enjoyed each other’s company. I dated Joe for the majority of Grade 12 (my senior year, for those of you not in Canada) and would continue to date him casually for 5 years.

After dropping my fantasy of having a threesome into conversations for a few months, Joe finally set the wheels in motion. An old “friend” of his, that he’d fooled around with off and on for nearly 10 years had gotten in touch with him, wanting to hook up and Joe suggested that I come along. Of course, I was stoked. I asked Joe to tell me more about our third. Alvaro, as per Joe’s description, was 29, Latino, a little shorter than me and had a thin, slender, build.

Sounds great, no? Here’s the best part. Joe made sure to let know that Alvaro almost exclusively hooked up with older white guys and wasn’t into black guys at all. My heart sank. Here I am, pretty much the exact opposite of what Alvaro was into. Sensing my uneasiness, Joe suggested that I chat with Alvaro on-line via MSN ahead of the big threesome. This was certainly going to be interesting.

Chatting with Alvaro was definitely a chore. He gave lots of one word answers and seemed very uninterested in learning more about me. We knew that there was no chance we’d be hooking up outside of this arrangement. Alvaro and I came to the conclusion that we would make it work, after all, we were doing this for “Joey”. I hated Alvaro referred to my Joe as Joey. It just seemed so petty to me, like he was rubbing his long past with him in my face.

Flash forward to the next weekend. Joe and I had been spending the day together in downtown Toronto. We went for brunch, window shopped and got a hotel room. Back in the hotel, Joe started kissing me. It didn’t feel the same. I think he knew I was anxious and was trying his best to calm me down, but it wasn’t exactly working. I laid in his arms on the bed, counting down in my head to Alvaro’s arrival.

I felt as if I was going to pass out when the anticipated knock at the door came. Joe let Alvaro in and they embraced. As they stood there, holding each other and sucking face, I rolled my eyes. It took everything I had to convince myself that I was doing this for Joe and to get my head in the game. This is what I’ve always wanted to do and I just needed to grit my teeth and get through it.

It was what I always wanted, but some fantasies should be left as fantasies. Seeing Alvaro blowing Joe really didn’t do anything for me. I did make out with Alvaro some and we took turns giving each other head as Joe watched. Joe looked like a kid in a candy store, but the interaction between Alvaro and myself felt cold and mechanical. The fact that Joe barely paid any attention to me unless I was messing around with his longtime friend cemented things for me. When Alvaro eventually rolled on a condom and began to fuck Joe, I crawled over to the other side of the bed and started checking text messages and catching up on emails on my phone. Clearly, I was disinterested and deflated, in more ways than one.

When the two old chums had finished doing the deed and Alvaro had left, I put on a happy face. I didn’t want Joe to see how disappointed I was with how everything went down. I never brought up the threesome after that day and I never suggested that we plan another one. Will I ever have another threesome? Who knows? Maybe I’d be open to it at some point with the right cast of characters.