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How Did You Learn to Masturbate?

Six men on the first time they choked the chicken—and the lifelong wank session that’s followed

“When my worries oppress my body, with my left hand, I release my pent-up fluids.” —Ancient graffiti in Pompeii

Most men’s sex education begins in self-imposed exile, alone, with his dick in his hand. Typically somewhere in middle school, a boy finds that his urine cannon is also a pleasure stick. What a glorious discovery that is! Then that boy’s natural-born sexual curiosity quickly becomes a source of shame. He learns that masturbation is dirty, wrong, pathetic and certainly not to be discussed. Hidden from guilt and shame, hoping like hell he’ll never get caught, he’s left to figure out his first lessons in sex and pleasure — all by himself.

As he cobbles together some nascent understanding of masturbation, from what he sees in the culture, he mixes that together with what feels good. Then, he begins to sneak-away to beat the bishop. To charm the cobra. To play the skin flute. He learns how to game the feel-good system of his body and brain — kinda like hacking a slot machine to always pay out. This is how his ideas of pleasure form. It becomes a pursuit of release. It’s a mechanical expectation to be satisfied.

This also explains a lot about men’s relationships to sex with partners. Our sexual awareness was founded in the dark. It was shaped by a boy’s understanding of what feels good. Plus, culturally, male arousal gets dismissed. It’s treated like fast food. A cheap and easy way to say “Mmmm…”

Is it any wonder then that boys and men who were forced to teach themselves about sex and pleasure might later become problematic for their partners? Whether it’s negligently attending to their partners’ pleasure, or misunderstanding what is and isn’t consent. Or more subtly, the selfish desire to use one’s partner simply as a means of pleasure — kinda like masturbating with their body.

Each of these issues tracks back to the sad fact we don’t talk to boys about sex in meaningful ways. It’s also why we need to speak openly of self-pleasure. As we’ve seen, the sexual frustration of men can become monstrous. So for better sex, sexual relations, personal health and the good of us all, we need to be able to talk openly about the five-knuckle shuffle.

Like, how did you learn to jerk-off?

Depending on how old you are, and when you started, you may not have grown up with the internet. Or perhaps you remember using the family dial-up modem to furtively download porn jpegs. (You know how wack that was. Pardon the pun.) These days, porn is far more accessible. With smartphones, you essentially have a porn machine in your pocket. But it’s likely you don’t know much more about masturbation now than when you first started to fuck yourself. (Despite the burgeoning field of masturbation coaching.)

And even with the internet, what you find there is a mirror of our offline culture, especially when it comes to sex and sex education. For instance, there’s more info online about men’s dick fears than there is about self-love. From a quick Google search:

  • Premature ejaculation: About 3,410,000 results (0.31 seconds)
  • Men’s masturbation tips: About 2,550,000 results (0.31 seconds)

This makes sense. It’s easier to sell fear than self-pleasure. Content creators and advertisers know that dudes are more likely to click on a post about how to beat premature ejaculation than about how to beat your meat. Besides, guys generally think they know how. After all, if there’s one thing in this world we’re good at, it’s jerking off.

But what helpful advice is there for a man looking to get better at pleasuring himself?

Sex toy-maker Lelo offers up this handy guide to male masturbation. It’s not bad. Over on the question-and-answer site Quora, a poster asked what are the best male masturbation techniques, and other readers responded. One guy shared a step-by-step guide with pics for how to make a masturbation sleeve using a rubber glove, a towel, rubber bands and some lube. Of course, as guys we try to hack masturbation with DIY tech — MacGyver style. A female reader recommends that guys phase out their use of porn and instead focus on their own fantasies and bodily sensations. Particularly, the frenulum. It’s called a foreskin orgasm, or a “fremgasm.” This technique works better for uncircumcised men. For men who’ve been cut, it depends on how much frenulum is left from their circumcision. If you’ve never tried it, it’s worth giving it a whack (again, pardon the pun).

Teen boys today are lucky. Many of us, for instance, didn’t have BuzzFeed handing out solid advice on masturbation as a safe and healthy form of pleasure. Or, if you prefer your advice more raw and real — Reddit. There are also whole sites devoted to slapping the bald stranger. (As always, consider the source.) Counterintuitively, though, the best sex writing you’ll find about male pleasure, like this post, is on women-centered sites like Bustle. Thanks to the feminist revolution, women have been taking their pleasure seriously for decades. They understand that arousal and climax is a form of freedom and power. Meanwhile, men enjoy a far less examined sex life. It’s time, however, to change all that.

To kick-start at least a portion of that conversation, we convened this roundtable to ask men about how they learned to jerk-off. Their answers are as undeniably honest as morning wood. [Editor’s Note: The names have been changed, because these are grown men who are still ashamed of the fact they pleasure themselves — a big reason why this conversation is necessary. For the record: Z-Man isn’t me; he’s a Canadian friend.]

What’s your preferred term for masturbation?

Michael (straight male): Jacking off

Ben Davis (straight male): Beating off.

Seymour (straight male): I’ve always only referred to it as jerking off, which I think comes from a term for how to get a horse to moving. I’m reading a book called Blood Meridian by Cormac McCarthy. I heard about it through this podcast. And the host was talking about how when a Native American would “jerk off,” they’d get going on their horse.

Hans Jurgen (gay male): Masturbate, jerk off, rub one out, pleasure myself.

Z-Man (straight male): I wish I used some clever or classy turn-of-phrase, but for me, it’s always just been jerking off.

DJ (straight male): Choking the snow angel. No, I’m kidding. I guess, for shits and giggles, I say, whacking it.

Do you remember what age you started?

Michael: Probably in middle school.

Seymour: I can’t remember exactly. I’d been exposed to my buddy’s porn. And I remember seeing it happen during intercourse and thinking maybe I could do that to myself. I was about 12 when I first did it. It was something that I didn’t understand so I felt horribly guilty about it after I did it for the first time.

Z-Man: I have a weirdly specific memory of playing with an erection during breakfast before school back around Grade 2 or so. But the first time I ever experienced an actual orgasm would’ve been in Grade 7. I was in the shower, similarly playing with an erection (which now appeared with MUCH more frequency) when I suddenly burst forth and experienced a level of immediate euphoria I didn’t know was possible. I took a LOT more showers after that.

Hans Jurgen: I was a total late bloomer — not until college — not until after I had already been in a sexual relationship with a girl! I think I thought that it just wouldn’t work? Like, I wouldn’t be able to make it happen? In hindsight, I think I was already trying to avoid dealing with my sexual preference. I probably would’ve already jerked off to men in my mind, and so, the whole thing seemed impossible.

Davis: About 11. I saw Laetitia Casta in the Victoria Secret catalog. I just knew I had to do something about that. (laughs) There are only a few red-blooded straight men of our generation who don’t know what I’m talking about. For me, it really started with a set of fuzzy flannel sheets and a pair of pajamas that didn’t quit fit right. All of a sudden, it was like, Wow, this is interesting. Then I had to change my sheets. (laughs)

How did you learn to masturbate? Did anyone teach you anything about it?

DJ: No, no one taught me anything. It wasn’t trial-and-error as much as it was trial-and-flourish. Been killing the game ever since. You know when you just realize you’re good at something. It was like that. (laughs)

Michael: I don’t think I learned from anyone. It always felt very natural.

Z-Man: No one taught me. In this instance, I was an autodidact. Everything I know about jerking off I learned by myself. The truth was that I NEVER talked about it. I was already something of an outcast at that age, and I knew talking about this with anyone would just lead to it being used against me in some way. Even at that age the hypocrisy of this rankled me, since I knew — based on how it felt — that EVERY boy my age did it. But somehow, we were supposed to accept that it was solely the domain of “losers” and “freaks.”

Davis: Like all teenage boys before the internet — or in the early days of the internet — you crowded around some porn someone had. It was all sort of DIY. You had to sort of teach yourself what there was to know. If anybody taught me anything, it was how to deal with the digital trail that you inevitably left as a 12-year-old on a dial-up modem trying to download three jpegs. That was the knowledge that got passed around — how to delete browser history and cookies of those early internet porn sites.

As for masturbation itself, once I figured out the hand works better than a set of sheets, the ball started rolling. You always hear about the microwaved cantaloupe, melon in the couch cushion or some other sort of American Pie-esque idiocy. But no one was ever seriously trying that stuff. Like, no one had a personal favorite recipe for hot melon. (laughs) That said, any middle class kid who had a pool will tell you about the joys of the out vent. (laughs)

Hans Jurgen: In college, it somehow came up with my roommate, who casually said that, yeah, he masturbates. I was like, “How? Where?” He said in the shower, with soap. So I tried it and was like, “Holy shit!” I certainly can “make it happen.” I also quickly learned on my own that soap isn’t great for extended or frequent uses.

What about lubricants? How did you work those into your one-man sex game?

Seymour: When I was younger I didn’t know how to lubricate, properly. So a lot of times I’d do it in the shower with soap. That ended up not being the best way because it makes your skin raw. (laughs) Next, around the time I started shaving, I began using shaving cream. I learned that I could do it for longer without it chafing me. Then I heard about Vaseline and tried that, but it never made sense because it was so sticky and oily. I was like, How do people jerk off with this shit? It just didn’t make any sense; it was so awkward. That’s when I started to just use my own spit. I’d just spit on my dick. Directly. Finally, I found out what KY was, and since then, I’ve used proper personal lubricant.

Davis: I used to be a big Vaseline fan. But ultimately, I found the clean-up to be more trouble than it’s worth. There’s sort of a materials science thing to it. You have to figure out what works. And as a kid there’s always a tub of Vaseline lying around the house. You use that. But it fucks up your T-shirts; it makes your socks all weird looking; it’s just a mess.

If you’re black, you end up with cocoa butter — because that’s another thing that’s always around. And at least it gets absorbed by the body. I’ve moved on to more natural, easily-absorbable materials. Also it depends on what you’re in for. If you’re on your own for the evening, you might prefer something that has a little more staying power, than say when you have 10 minutes before you have to be at a meeting.

What did you learn about masturbation from pop culture?

Michael: That it was a very taboo thing to talk about, or to reveal to anyone.

DJ: There’s a latent Catholic thing — that big message of “No!” But while I did get the message that it was dirty, I never really felt shameful about it. Honestly, it’s only shameful if you get caught. For me the rule was Thou Shalt Not Get Caught. (laughs)

Z-Man: Weirdly, it was only AFTER I figured it out for myself that I understood all the previous references to masturbating I’d seen in the media. Before that, I didn’t know what was happening in those scenes. Also, there really weren’t a lot of overt masturbation references in the media aimed at tweens back in the 1980s. If Arnold ever talked about it with Willis on Diff’rent Strokes (heh), I definitely missed that Very Special Episode.

Hans Jurgen: There’s a certain association of masturbating and teenagers. That doesn’t really make sense — like, adult men don’t masturbate? Or just don’t talk about it? There’s also a big association of masturbating and sexual frustration. You’re not doing it because you enjoy it and it feels good, you’re doing it because you can’t get laid — or not laid enough. Plus, what do men usually do to jerk off? They watch porn. But most women hate porn. That’s one of the convenient things about being gay. Porn is way more accepted as normal.

Davis: Mostly, I just learned to be ashamed of it. I remember loathsome days in my 20s when I was unemployed and had an internet connection and nothing to do. By the time the sun went down, I did feel pretty ashamed of myself. (laughs) That puritanical shame of not being productive is more the message I got than any particular religious sexual shame. It’s more about, “You should be doing something with all this energy you have.” The thing that sort of always shames me: It usually takes me as long as if I just went for a run. And I feel like I should just go for a run. But then I go for a run, come back and want to beat off anyway. (laughs)

Is your technique now pretty much the same as it was when you started?

Seymour: Yep. Pretty traditional. Nothing too creepy.

DJ: No. It’s much more exploratory and weird when you’re a kid. Then it becomes kinda boring as you dial it in.

Michael: It’s stayed consistent for sure.

Davis: More or less. I mean, I’ve tried to pinch hit with the left hand, from time to time, but usually, it’s like, This feels awkward, and the other hand knows what it’s doing.

Hans Jurgen: I’m super boring; I don’t even change hands. Well, sometimes, on special occasions I’ll use a butt plug.

Would you ever be curious to learn new tips or sex hacks — maybe hear about what other guys do to continue your sexual education?

Davis: I never got to that second stage with anybody. But I do remember in junior high, somebody said in the locker room, that the more you masturbate, the bigger your dick gets. We were all like, “Wow!” For that next week, we all beat our little 13-year-old dicks, furiously. We came back to practice the next week, and I was like, “You a fucking lie.” (laughs)

That was the last time I was even close to entertaining those conversations with other men, ’cause I’d learned guys talk nothing but shit about their dicks. I don’t want to trade in those tall tales, or sit there and listen to yours because, man, I know you’re as full of it as I am. (laughs)

Seymour: I’d be more curious about what things men have sex with, as opposed to their hands. Like, I’ve heard about people screwing fruit. Or the things you can get at sex stores. There was a gay pride event in San Diego, and one booth had these sex eggs. They were free. My friend picked one up and gave it to me. I was like, “What the fuck is this thing?” And he was like, “It’s a thing you beat off with.” Curiosity got the best of me, and I tried it. I was like, “Oh, ooh, wow, this is different, this is new.”

I hardly ever use it because I’m too lazy. But it’s called like a Super Sucker, or something like that. It’s like a sock, a super flexible, rubbery thing that I fuck. It was game-changing. I wanted to spice up the ol’ love life… with myself. (laughs)

DJ: I’ve been asked by a woman who wanted to watch me. I said, “You’re right here, and interested. You do it.” It’s the fact that it’s not you doing it, that’s the cool part. You can always do it by yourself, but having someone do it to you is what makes it sexy. She was surprisingly good, which is rare. Most women aren’t good at handjobs.

Z-Man: In my 20s, I briefly worked at an adult video store, and it occurred to me that I was in the same realm as sex workers and shrinks — many times people, over the course of our transactions, would be admitting things to me they hadn’t told anyone else before. Once again, it highlighted to me how screwed up we are as a society when it comes to this subject. Everything we know tells us this is a near-universal experience, yet there’s a cloud of shame attached to it.

Why do you think we shame and dismiss male self-pleasure in America?

Davis: Maybe this is just my own sexual experience, but I think even liberated, modern sex-positive women are sort of meh about men’s pleasure. Because they know men can beat off. Men’s pleasure isn’t valued because it’s so easy to climax. That’s part of the cultural shame about it. If men didn’t feel cultural shame about beating off, we wouldn’t get anything done. (laughs)

Like, there are whole books about the female orgasm. In woke circles, we spend a lot of reasonable and necessary time talking about women’s pleasure and the involvement of women’s pleasure in the straight sexual experience. But when it comes to men, women are like, “If you’ve got an iPhone and 10 minutes in the bathroom, you’re good. So I don’t give a fuck.” That’s the interesting larger cultural messaging I pick up on these days.

And in relationships, the message seems to be: If you’re woke and a guy, your focus should be on a woman’s pleasure. Your pleasure is sort of secondary, if it’s meaningfully considered at all. To be a man interested in his own pleasure is to necessarily be chauvinist, which I disagree with.

Hans Jurgen: Why don’t we value male self-pleasure and actively discourage talk of it? It’s the same reason there’s soooo much therapy, moisturizers, batik print sarongs and yoga retreats for women but not for men. We’re supposed to be rugged and simple and not care, blah blah blah. “Just go rub one out in the bathroom; you don’t need candles, tantra, vibrators or adventure.” We’re totally verklempt. It’s sad! Men should be fabulous, if they want.