As an obsessive podcast listener, when people get asked “How did you get into…” I always expect them to say “I can’t remember when I was not into…”. Sounds familiar? But this is not how it went with me and fisting. There is a very discreet moment, for me, and it (seems to me) was relatively late in my “development”.

I was about 22, definitely no older than 24. I was living in Vancouver at the time. I had been having fairly bland vanilla sex for a few years. I had a general curiosity in kink, with not a lot of specifics and null experience. I kind of knew that I always saw myself in the “active” role (I mean it in a literal sense) and since I wanted to be the one “doing things”, I figured I needed to learn… “things”. I am generally a very cautious, perhaps even too cautious, experimenter, so I was very hesitant to try things I wasn’t sure I could do well, safely, confidently, and so on. It occurred to me that a possible way of exploring this would be, bluntly, threesomes. The idea was to find a D/s couple, and learn from the top while having the opportunity to practice on the bottom. Well, when you are a tall 22 year old Greek boy it’s not that hard to find a threesome with a self-described Master/slave couple, it seems. I believe that was one of my first times using Recon. Wow. My account is that old?

While this didn’t turn out to be very productive as a learning route, at least not with this particular couple, it did provide the context and opportunity for me “breakthrough”. The couple didn’t really do much in terms of a SM activities – it was mostly roleplaying (the Top was very verbal), very rough fucking, and a bit of dressing up: the bottom always wore leather restraints and a heavy leather collar, but they never used them for anything. They did have thick latex sheets, partly because they used tons of lube and partly because they did get into watersports, though I don’t remember ever doing that together. So if I learned anything from the top it could only have been dirty talk. The one thing though that enabled what I am about to describe was that the top – otherwise unremarkable tall white Canadian dude – was remarkably well hung. Not just long, but disturbingly thick. I mean, it looked as thick as my wrist. Do you see where I am going?

That element, and the fact that they used a lot of lube and rubber sheets, probably already gave the rest of the story away… One time after a particularly rough and prolonged fuck, I was playing with the bottom’s butt with my hand. There was lube (and possibly cum, they didn’t use condoms together) pooling on the sheets, and I was picking it up and kind of trying to put it back in. An important sidenote: at this time innocent 22 year old me had no idea what fisting was, that it existed, and that there were people into it. My few failed and painful attempts at bottoming would probably not have allowed my imagination to conceive of anybody being able and willing to have a fist in their hole. And this couple was definitely¬†not practicing or seeking fisting – though I’m guessing the bottom has gotten into it since then. And then it happened, magically, without effort, and without the bottom particularly noticing it. My entire fist, past knuckles, just popped in. It was actually the Top that was the most surprised out of the three of us. He seemed angry but I think it was just how shocked he was, as he shouted; “Dude, you just fisted my boyfriend!”

And that was the first time I knew that fist was a verb as well as a noun. I was immediately hooked. It had been so natural, so effortless, it had none of the barriers that made trying other kinks so daunting to me back then. When I went home that night I downloaded every fisting video I could find. If I remember correctly I changed my Recon listing to fisting that very night (until recently Recon only let you have one “preference”). Unfortunately, after the initial excitement passed, I actually developed the same hesitation about fisting that I had about every other kink. I didn’t feel I knew enough, I wasn’t confident, I was afraid I could hurt someone, etc etc. Additonally, I wasn’t sure how you tell someone “I’ve never fisted anybody but I would like to put my hand in your butt”. In this context, I would argue that getting into fisting (only) as a top is a lot harder than learning to bottom. The physical barrier might not be there, but at least for me trusting my own competence was harder than finding another person to trust…

And so it was that, unfortunately, after that first time it took me several years to work up the courage to meet someone with the expressed goal of putting my hand in their butt. There was some (hot) occasional fistings or near-fistings in the meantime, but never because of my initiative. I regret those years now – I really feel I wasted a lot of my 20s not having the type of sex that I enjoy and that I know I can make others enjoy. I really think my super-active days in New York City were due to trying to compensate for this. But I will talk more about this, how I got over my inhibitions, including some advice for beginner tops, in a later post…

If you can relate to this experience, or if the way you got into fisting was radically different, I would love to hear from you, and I am sure other readers could also benefit from it. Please feel free to comment below!