Pegging for the first time

Please note: This article is published as an archive copy from Philadelphia City Paper. My City Paper is not affiliated with Philadelphia City Paper. Philadelphia City Paper was an alternative weekly newspaper in Philadelphia, Pennsylvania. The last edition was published on October 8, 2015.

My favorite part of pegging is giving my partner pleasure.

I've never been the kind of woman who wondered what I'd do if I had a penis, so the first time I tried strapping on a dildo, it was because my boyfriend wanted me to. I was game for backdoor play, but I needed some reinforcements.

My first task was finding a suitably feminine sex toy for a girly-girl like me. I didn't want a traditional harness, which works wonders for some people, but to me felt too spare and utilitarian.

So, I was happy to find the body-hugging, SpareParts Sasha panty harness, in red, of course; it was worth $150 for me to feel comfortable and sexy. The bikini bottom looks like it belongs in a high-end lingerie shop, except that it has an O-ring embedded up front, which holds the dildo in place.

The first time I tried it, I felt awkward; after all, I suddenly had this appendage sticking out of me. Next, I had to find a position that felt comfortable for both of us, and that was trickier than I'd imagined. When I had used the same dildo manually, I had a front-row seat to see exactly what I was doing. But with the panty, I didn't have the same level of control, and kept asking, "Are you OK? Does that hurt?"

While it's important to check in during sex, my extreme nervousness was ruining the mood. "I'll tell you if it's too much," he assured me.

Slowly, we found our rhythm, with a few more verbal assurances along the way. For me, it wasn't the power trip I'd been expecting. I didn't have some "aha" gender revelation, like: This is what it feels like to have a dick! I was fully aware the whole time that I was a cisgender woman using a sex toy, but I did get a rush of power knowing how good I was making my boyfriend feel. There are some noises you just can't fake, and his were sounds of pure bliss.

So, once I got over my fear that something would go awry, I got more into it. While I'd never been as big a fan as he was of being on the receiving end of anal sex, his pleasure felt familiar to me, because I've made similar sex squeals.

Since then, I've discovered that I don't have to wear a cock to wield one well. I piled up pillows to try to make the pegging position work, but no matter what, our bodies just wouldn't align. Rather than becoming overly frustrated, I got naked and worked the dildo manually.

I controlled every motion, easing back or pushing forward at my comfort level. Eventually, I lay down on top of him, fingers digging into his shoulders, my breasts against his back, pressing the toy forward with my pubic bone, mimicking the job of the panty with the dildo attached. Afterward, the sex was explosive, for both of us — though I hesitate to call pegging "foreplay," because it's its own main course.

My favorite part of pegging is still giving my partners pleasure. If backdoor fun lights their fire, I want to be the spark. To me, being able to do that is all the power trip I need.

Anal sex has come a long way in the popular imagination since S.I.R. Productions released its pioneering educational porn video "Bend Over Boyfriend" in 1998. (If you're curious about the topic, it's worth watching.) But, too often it's still framed as something a man does to a woman, and something that dare not be discussed outright, such as on The Mindy Project episode "I Slipped."

Is someone out there ready to become the poster boy for pegging?

Rachel Kramer Bussel is the author of the essay collection Sex & Cupcakes and editor of over 50 erotica anthologies, most recently Hungry for More and The Big Book of Submission.

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