8 Awkward Steps in My Masturbation Education

Repressed parents, lousy porn, and horny friends led to an exceptionally awkward sexual awakening.

When I was in kindergarten, I used to lay in bed butt-naked, spread-eagle, and imagine girls from my class, falling on top of me through the ceiling. Then, we would hug each other very tightly and roll around. At this point, I’d never seen people have sex, nor had I seen porn. I just instinctually wanted a warm body against mine, never suspecting for a minute that this spout between my legs needed to be in any way involved. This weird habit aside, my interests were more in building forts, putting ketchup on chicken, and refusing to take off my blue power ranger outfit. Then, one dark night, everything changed.

Step 1: Just wrap your fingers around it and go up and down.

Sleepovers were the in-thing in the 90s. Without group texting, if I wanted to interact with my friends, this meant seeing them. I was seven or eight, and my best friend was named Joey. He was cooler than me. This isn’t saying much about Joey, though, since I was still refusing to take off my power ranger costume. It was the middle of the night, and I was almost asleep, tucked innocently beneath a blanket on one couch. At the same time, Joey lay, breathing heavy, on the other. I was almost in dreamland when I found myself shaken awake. Joey was standing over me, and he said:

“Have you ever masturbated before?”

“What?” I asked. And he smiled like adults smile when they find out you haven’t yet heard this really great band. (Yes, kids, surprises get worse and worse the older you get).

“You’ve gotta try it,” he said. He held up a finger, then used his ring and middle fingers to press it into his thumb. He started moving them up and down.

“Do that,” he said, “But — “ and this was the kicker, “with your penis.”

And I did.

Oh, boy, did I.

I don’t remember what happened to my blue power ranger outfit after that.

Step 2: There is more than one way to burp a baby worm

When people imagine men masturbating, they’re often picturing a man with a fistful of dick violently going up and down like it’s some sort of weird carnival game where, if they do it fast enough, money will shoot out the top. It’s not really like that — especially not when you’re a kid whose penis hasn’t grown into the size of your hands. Three fingers — that was how I learned. I didn’t realize anyone did anything different until kids started making masturbation jokes at school, using their whole fist to simulate the action. At first, I’d be like, “yeah!” and hold up my three dirty fingers without realizing anything wrong with it.

My cool streak lived on.

Step 3: The porn chooses the wizard

My mom always said that beggars can’t be choosers. That was never truer than when my friends and I managed to get ahold of porn. Sometimes it came from older brothers, sometimes from stashes, they found of their dad’s. I never discovered porn in my house, so I always had to rely on friends.

My first porn came as a VHS tape smuggled over by my friend Peter. We locked the door to the basement in the middle of the day, turned out all of the lights, and hit play. It was vampire fantasy porn. This was all well-and-good until we found out how the men were turned into vampires. Yes, they bit off their penises.

It was only after that moment that I turned to look at Peter and realized, to my horror, that he was masturbating…too.

Step 4: Masturbating together — no, not on a cookie

Whether it was 2, 4, or 7 young boys, it got to a point where no sleepover was complete without someone sneaking over a porn tape. And, no, boys don’t just watch it to comment on the physique. This stage, in particular always makes women I’ve told cringe.

“You really all masturbated in a room together?” they’ll ask.

“Yes.”

“Like on a cookie?”

What’s with the cookie thing? This was a viral rumor that occurred before the internet where people assumed that boys played a game where the last person to come on a cookie had to eat it. While most men I’ve talked to have experienced childhood group masturbation sessions, I have yet to meet a guy who said, “Oh, and remember doing the cookie thing?”

Also, many of my friends couldn’t actually produce semen when we started masturbating.

Step 5: Getting through the dry period

Yes, boys can masturbate and even orgasm before they can produce semen. Most of the boys I grew up with couldn’t come when they started. I miss it, actually. It was a cleaner time in my life — no dirty socks or crusty underwear or having to lean over a toilet. There was no gooey reminder of shame leftover. For the first few years of masturbating, I was unable to produce semen. What started as a convenience soon became something shameful. Other kids began to be able to produce semen, and it became a weird little test of manhood. I remember being at a friend’s house where we were masturbating over the back cover of some video game, and two of my friends ran to the bathroom. Feeling embarrassed, I went after them. When I came back, they asked, “Did you finally come!”

I was like, “Yeah! Oh, it was great.”

To be honest, it was good practice for my high school years when I’d lie and say, “Yeah, blowjobs…uh…totally feel great!”

Step 6: You end up doing it in weird places.

One day, it happens! The burp in your worm, the tartar sauce in your rainbow, the tears in your bald man’s eye. Now, where to put it? Everyone has their go-to spot. Someone sent me a post on Reddit once about a guy who did it in the same box over 10 years. Gross. Most boys go for a sock, or the smart ones have tissues beside the bed. In the end, there is no great place to put it, especially since it can pop up at the worst times. Horniness is a lot like hunger for a teenage boy. So imagine that you periodically get agonizingly hungry and are lucky enough to always be walking around with a bucket of chicken in your pants.

Yeah — you get the idea. I could list all of the places my teenage self shamefully masturbated, but this article would become an hour-long read. Basically, it’s gross. Just gross. That’s all I can say. And, eventually, someone catches you.

Step 7: Your parents eventually find out, and it’s weird

My mother has an uncomfortable sense of humor. She called “Bring It On” the masturbation movie. If I ever tried to watch it with my friends, she’d yell after us, “Ooo, you guys going to watch the masturbation movie!?”

It was a damn good movie, okay? Just that. Great acting. Spot on-camera work. Fantastic soundtrack. Really a first-rate flick. That’s all. Okay, mom?

And the day she walked into my room, burst out laughing, then slammed the door and called, “What were you doing?” I didn’t — did not, have the Bring It On VHS tape in bed next to me.

Step 8: Mastering the art of discrete masturbation

Eventually, masturbation becomes more of a habit than a need. Rogue boners come around less and less, and you meet someone who lets you do with them what you’ve been doing to yourself for years. I’ve never met a man who had an orderly unawkward experience learning to masturbate. It is always cringy, gross, and embarrassing. Some kids learn from family members. Others discover it for themselves. I’d imagine that these days many kids can just look it up. Some men I’ve met got way too comfortable with food when they were starting out. One guy even admitted an alarming hot-pocket incident to me.

The important thing is to be able to laugh at the absurdity of this process. I think I was lucky to have parents who at least never talked about it. Some kids are scolded or taught that it is awful or blasphemous. It’s not. It’s awkward, hilarious, and a part of growing up. Though, maybe if you are a sibling or parent of young boys, just don’t think about it too much — and remove all blacklights from the premises.

*also, doesn’t it totally look like that guy in the cover photo is shamefully masturbating behind some building?

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