How Do Men Discover Butt Play?

Category: Points Of View

Author: Benjamin Davis

Men stick their fingers up their nose, in their ears, under their pits, between their toes, and into the corners of their eyes, sometimes – if not often – without washing in between… So it’s a mystery why so many men have a knee-jerk aversion to a finger up the bum. 

Often, when I meet men like this, they have one thing in common: they’ve never tried it. The inherent aversion – after the boyhood ignorance of not wanting to be labelled ‘gay’ is gone – being that “poo comes out of there”. I was like this, that is until, one night, on a rooftop in New York City, a lovely young woman shoved her finger so far up my ass that she dislodged a popcorn kernel stuck in the back of my throat. This isn’t to say I hadn’t thought about it or popped a few things up there as a teenager, but those were experiments more in the name of science than pleasure.

Anal play is like sushi in that way: you just need to try it and, most of the time, you’ll love it. But you’ve gotta open that back door first. From there, a guy might try it on his own, invest in some toys, and step into a whole new world. Without that first experience, some straight men won’t ever try it – despite a lot of women who like it. With this in mind, I asked some men I know first if they’re into it, and then, how they got into it, to try and narrow down some of the ways people might ‘open up’ to the idea.

For me, it was a pleasant surprise with a blowjob, and this, I think, might be the best way to introduce, well, any idea to someone with a penis. All surprises are better with blowjobs – if someone stabbed me while I was getting a blowjob, it’d take me at least 30 seconds to realize it wasn’t pleasurable. 

For a friend of mine, it was a much more adventurous experience. An older woman brought him home from the bar one night, into her living room, where, in front of a neat little fireplace, laid out on a svelte purple shawl, was a collection of sex toys. She’d gone to that bar with a plan. From there, they spent hours exploring all sorts of things that now play on repeat in my mind every time I look into his eyes for too long. 


For another, he and his girlfriend were exploring ways to spice up their sex life and she recommended it. They hadn’t been a wildly explorative couple, so they started small. From there, it snowballed. Another friend never brought it up, but instead was asked by his girlfriend if they could try it because she’d heard about it.

I did not, however, manage to find any men who’d started experimenting this way with a partner in high school. Teenage boys tend to be awkward, shy, and wrapped in insecurities. And I do still have – of course – a few tight-ass type friends who simply refuse to try it, and others who have, and haven’t enjoyed it – hey, butt stuff is not for everyone. 

Some men, however, will always be solo frontiersmen. My friend, for example, discovered anal play by letting his family’s bath candles get warm, shaping the wax into a dildo, and playing with himself. Another friend explored forums online, learning about the joys of the prostate, and jumped head-first into buying the most highly-rated prostate massager he could find. Another? Hotel shampoo bottles. (Please do not try this at home or in a hotel.) 


And sometimes, it’s a combination of things. Myself, for example. I’d never tried it with a partner, but I’d experimented with a marker or two. I didn’t find it pleasurable enough and was also afraid to ask for it with a partner, never mind order a toy. Since it isn’t often discussed among men, especially young men, we can go years – a lifetime! – without discovering this potential for pleasure.

I do think most men eventually wear out their nose, their ears, their pits and toes, sit back, look at that finger, and wonder, “Now, where else could I put you?” Some just need someone to point them in the right direction.

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