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How I Started My Fisting Life

January 11, 2023

How I Started My Fisting Life

Written by Alexander Cheves

I first got into fisting in San Francisco after being afraid of it for years. The fear is the tell: fear is the other side of wonder, and very often they are mistaken for each other. 

I had chatted with many guys online about fisting, but my first time happened through old-fashioned, in-person cruising at a party. And like the best cruising sex, it happened without a discussion. Somehow he knew that I was into fisting, or suspected that I wanted it. He held a cold bottle of poppers under my nose, greased up his hand with gobs of thick lube a final time after slowly working me open, finger by finger — and pushed in. 

The sensation was strange and alarming at first. I now know that one’s first fist is usually jarring: I’ve been the first fist for several men in the years since. The suction of the rectum means that once you’re past the widest part of the hand — the knuckles — your ass will naturally “pull” the rest of the hand in. There is a natural point inside everyone’s hole where the hand comfortably sits: sometimes wrist-deep, sometimes shallower, sometimes deeper. But this comfort spot is where the hand seems to settle. This is what I call “parking” — the point where you start to relax and get roomy. 

He parked — once, twice, maybe a third time, in and out — and that was it. I was exhausted and a little sore after. That’s a lot for a first hand, and the fact that I managed not to freak out when I took it to the wrist means I was ready for it. I had trained, starting with a small butt plugs some years before and working my way up with toys ever since. He knew none of that. He just met my eyes in a dense crowd, we had a cursory run-through of what we liked (he was dominant, I was submissive), and then we hopped a taxi back to his place, and a few minutes later I was bent over in a leather armchair with a blindfold over my eyes. I never told him my limits, never presented a list of interests; he simply read my body and I, in my way, read his. It happened organically — animals in a mating dance. He was gentle but forceful. I remember him telling me not to pull away, and I didn’t. 

I don’t remember much about him: he had a growl in his voice, a shadow of a beard, and he was older. I never learned his name, but in my memory, he was between forty and fifty years old, which means he was fisting before fisting was cool again — before it blossomed like a rosebud across Twitter, where OnlyFans stars now compete for World’s Biggest Hole. 

The story of how fisting fell in and out of vogue is intimately tied to the history of AIDS. In the early plague years, before we knew more about HIV and the mechanics of its spread, fisting was blamed in gay magazines everywhere as a sexual epicenter. In truth, fisting on its own is fairly low-risk for HIV transmission, so long as you don’t bareback simultaneously. But all the same, fisting was smeared as something violent and dangerous (a poorly-selected word like “fisting,” which sounds violent, didn’t help). I don’t know how it changed — if its taboo lessened post-PrEP or if it always held its appeal in adventurous sexual circles, even in the wake of AIDS: I can’t know. I wasn’t around for most of that history. I was HIV-positive when I was first fisted — PrEP took off about two years after I seroconverted — and I did not discover my kinks, fisting included, until after that pivotal life turn. (I wonder now: Would my fetishes have felt as accessible as they did if I had been HIV-negative?) 

Everything important in my life came after that first fist: the start of my sex column in The Advocate, my career as a sex writer, my first book. In the background of my greatest periods of growth, I was stretching my hole, learning how to relax, learning how to trust — and the really beautiful fisting nights, the punches and huge toys, came as I was ready for them. I never rushed, never felt like I was in a competition or onstage — as I fear many newcomers to the scene feel when they find fisting on Twitter and JustForFans. It’s not a journey of advancement, simply of pleasure: You only do it to the point that it feels good, and if that’s “mild” fisting (as opposed to the more hardcore stuff) that’s great. You’re one of us. 

And if you’re not part of us, you know where to look: online. But I wish everyone could have a first hand like mine: connected, in-person, cruisy, an experience of closer kin to the way sex was done in the 80’s than now. I like Sniffies because it feels closer to that, with its cruising map and minimal profiles. Among smartphone apps that strip all mystery out of an encounter, Sniffies fosters easy, anon, IRL sex. 

Fisting is nothing more or less than a profound exploration of intimacy and vulnerability — and it feels great. Come be part of it.


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