How I Learned To Get Pegged And Like It


Three months ago, I thought I completely understood women. And why wouldn’t I? Twenty-five years is enough time to understand three billion people. I grew up in the snug cove of the Bay Area, went to a college named after a woman, and got real good at turning my feelings into words. Eventually I got so good at talking about feelings that I started doing plays, so I could talk about feelings I didn’t even have.

So why is it that, after decades of sympathizing with women, I feel like I’m just starting to empathize? It’s pretty simple. I got fucked. In a good way.

As a lover, I pride myself on being a nice guy, a boy scout in an army of mere boyfriends. Just look at my badges! Monogamy sits proudly at the top of my sash, and under that are Communication, Promise Keeping, and Spontaneous Flowers.

Like all good scouts, my passion for good citizenship is rivaled only by my thirst for exploration. So I found myself proposing to my (amazing) girlfriend of two (amazing) years that we try a little butt sex. The way I explained it, it was just another way to appreciate her and build trust. (Which is true, it just looks really creepy on paper.) She was hesitant, so I doubled down and put my own ass on the line. If she could take it, so could I.

After a romantic evening of Futurama, Wine, and a True Grit bootleg, she deflowered me. And I’ll never be the same again. I’m not going to get into any gory details, that’s what Twitter is for.

After it happened, I felt the same exciting relief I imagine a girl feels after losing her virginity on prom night. I never realized the incredible amount of bravery it takes to let someone inside you. It’s asking someone to stab you in the back, but lovingly. Masculine courage is throwing yourself headfirst into danger, like jumping out of a plane, but feminine courage is letting danger throw itself headfirst into YOU. It’s even more badass. I look at women like soldiers now, and older women as grizzled retired Generals that I wholeheartedly salute.

I also never realized how instantly bonding sex can be on the receiving end. I already felt close to her before we began our little experiment, but now I feel like she’s tattooed under my skin. Even though she was staying the night, I almost begged her to call me the next day.

So if your boyfriend doesn’t understand you, the next time he tries to give it to you, see how well he takes it. After years of formal and informal Women’s Studies courses, I feel like I’m just getting to know the opposite sex in a way I never could before.

God I hope I’m not pregnant.

Earlier: Everything You Need To Know About Pegging

Max Levant is a perspiring comedian and teacher living in Chicago. He writes sketches for the celebrated group Side Hustle.

This post originally appeared on Pluck. Republished with permission. Want to see your work here? Email us.

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