3 min

The reluctant top

Even after years of hooking up, still hesitant to pick a label

It’s late one Saturday night. I’m drunk and stoned on weed at my apartment, and I decide to go onto I’m one of those online cruisers that other online cruisers bitch about. You know, the type who logs on a lot and looks at photos of people, sends the occasional flirtatious message, but doesn’t really hook up much. In all my years of online cruising hours, I have probably successfully hooked up around 10 times. Considering I have had well over 1,000 casual encounters in my days, 10 times online is nothing.

Someone sends me a message: “Want a massage?” he asks. Hmmm… sounds tempting… so I reply, “If you are willing to come over here, only stay for as long as I want, and expect no reciprocation, phone me at….” My phone rings moments later, I give my address, and 10 minutes later he’s in the lobby. Wow — in terms of online efficiency, this is a good start.

I open my door and a guy who looks basically like his photos stands there with a duffel bag. He has huge bugged out eyes (I’d guess crystal or coke) but a gentle energy. He has his own towels and massage oils, so I lay down on my stomach, and he starts working on me. It feels amazing — he knows what he is doing, it’s erotic, and he doesn’t talk too much, which I like. I roll on my back and he does my front. My cock is throbbing hard, so he says in a sexy voice, “You must really want to put that somewhere,” and I answer “Uh… not really.” Then, remembering my manners, I told him, “Oh yeah, sure, have a seat.” I mean he just spent a good 20 minutes servicing me, the least I can do is let him enjoy my cock up his ass. He rubbers me up, I verify it’s on right, and he rides my cock with a big smile on his face.

I am describing the above encounter because I don’t know if I am a top, a bottom, or truly versatile. One of the side effects of being a sex worker for a lot of years is you lose sight of what you really like — it is a service industry, after all. When I was young, I was just a regular boy escort, but I did not engage in anal sex with clients. In my recreational encounters I would say I was the bottom more often than not. As I got older, I became a professional dominant. Sometimes that included anal, always with me as the top. During those years, recreationally I became even more of a bottom.

It’s a common joke amongst Toronto cruisers that “everyone in Toronto is a bottom” (although a friend of mine who is a flight attendant informs me that it’s the opposite in Ottawa…). Just go to any Toronto bathhouse late at night and you will see — it’s a parade of boys walking around, dropping their towels so they have to bend over, competing for the affection of a small handful of guys who will top. I know — I have been in that parade. When I was at my prime, and younger, if I was hit on by an older guy and he indicated he was a bottom, I would decline. It almost seemed like one of the privileges of youth: “I got the youth, you gotta do the work and let me enjoy the feeling of your cock on my prostate.” There is a clear hierarchy in cruising spots — it’s a bit crass, but try to tell me it doesn’t exist — it’s like a beauty pageant where everyone is ranked compared to others, and those with the highest scores get to choose who they want and what they want to happen. The lower your score, the lower your standards might drop. Or you can also choose to go home without hooking up. But if you have special skills — for example, a hard cock and an ability to use it, your value rises, regardless of your physical appearance.

I’m not a big fan of labels anyway, but there does seem to be a tendency for most guys to gravitate towards one end of the spectrum or the other. I used to think I was a bottom, no question, but lately I have doubts. I am sexually passive — I do enjoy lying back and doing very little, but does that make me a bottom? I am simultaneously titillated and terrified about cocks going into my bum — will it hurt? Will I push it out? Will there be poo? Or will it give me that incredible mind-blowing feeling that only those who have been fucked by a great top can understand? Sometimes the idea of becoming a total top is appealing to me — it eliminates a whole bunch of anxieties. Plus I just turned 34, so isn’t it part of my responsibility as an aging guy — to learn to appreciate the art of being a top? And when that guy from came over, although I was not initially interested in fucking him, I did it — and I gave him a great deal of pleasure. And isn’t that what sex is really all about: sharing pleasure?