Sex Week: A First-Timer’s Adventures in Pegging

“I had flashbacks to rock climbing and fervently wished I was about to rappel down a mountain rather than jackhammer my new love interest.”

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what is pegging

(Illustration: Cannaday Chapman)

“Are you still up for doing what we talked about?” the text said. “Yup,” I messaged back, as if the guy on the other end, who I’d only recently started dating, had merely asked if I still wanted to order pizza. I hoped my casual affirmation would show him how open-minded I am in the bedroom. Truth be told, I wasn’t sure what we’d “talked about.” I remembered the subject of anal coming up the last time we were in bed together—as part of a larger conversation in which we’d catalogued our past sexual experiences, feeling each other’s interests out. I’d never jumped into backdoor antics this soon in a relationship and was unnerved by the speed of things, but if that’s what his text implied, I could be game. Right? When he arrived at my apartment, he seemed boyishly nervous, which was a side of him I hadn’t seen and couldn’t help but like. He was wearing a backpack that added to the schoolboy effect. We sat through dinner awkwardly, and as I was clearing the table, I heard him hastily unzip his bag.

When I turned around, I saw three dildos on my kitchen table, arranged in size from small to large. “Oooh, I thought you wanted to… You mean, you want me to…” I said, immediately realizing he had a different idea of “anal” in mind as he fidgeted with a harness. I’d heard of pegging, but couldn’t bring myself to even mouth the word. He blushed and said we didn’t have to, but in the spirit of trying anything once—and, in all honesty, out of fear of seeming like a prude—I insisted, “You’ll have to show me how. I’ve never done this before.”

Feeling a bit like a dirty Goldilocks, I selected the medium-size purple dildo, hoping it would be just right. With the hands of an expert, he pulled the adjustable straps tight around my hips and waist. I had flashbacks to rock climbing and fervently wished I was about to rappel down a mountain rather than jackhammer my new love interest. “You look sexy,” he insisted. “I do…?” I replied, my sentence straddling the line between question and statement. I could see my reflection in a small kitchen mirror and worried I looked manly. “It doesn’t look like a penis,” he insisted. “Is it supposed to look like a penis?” I asked innocently, possibly ignorantly. “I mean, should I want it to look like a penis? I don’t actually know what I mean. I’m too new to this,” I bumbled. “You don’t look like a man,” he assured me, before handing me the lubricant.

We made out down the hallway. I was a bit too overwhelmed by the new experience to be genuinely aroused at first. I giggled awkwardly as the dildo bent in different directions before springing back into place. When we got to the bedroom, he lay on his back with his legs raised in the air. Seeing him in such a vulnerable position gave me a surge of power I’d never felt before sexually—there’s girl on top, and then there’s girl on top wearing a purple power tool. I started out gently and used his facial expressions and moans to gauge how hard or fast I should go. It was as tiring as it was awkward, yet I felt that undeniable rush you only get from trying something entirely new. Like a virgin, thrusting for the very first time.

More From Sex Week:
When Your Dude Is NDTF (But You Are)
6 Women Confess Their Secret Kinky Turn-Ons
Diary of a Polyamorous Relationship

Broad City Stars Abbi and Ilana: “The Best F-cking Interview”

 

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