How I Finally Convinced My Husband To Try Pegging

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The act of pegging entered my consciousness in the late 90s with the release of Bend Over Boyfriend by Shar Rednour.

It was so deviant. So transgressive. I wanted in! (Pun totally intended.)

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Picturing myself bending my husband, Flick, over our bed got me so excited, I even went to the local feminist sex toy store and bought myself a lovely leather harness. I figured we’d pick out the dildo together.

Flick was, alas, not so interested in taking a dildo, despite enjoying prior anal play with my tongue and finger.

“But your prostate …” I argued. He was not convinced.

Fast forward approximately 17 years and I was finally able to take that optimistically and prematurely purchased a harness for a spin — first with a few women, and eventually for its intended deviant purpose with my husband.

Woo hoo!

Experimenting with non-monogamy opened so many unexplored avenues for us (Dammit! There’s no way to write about this without endless innuendoes!).

As Flick grew more comfortable in a community that celebrated and valued men who stepped out of the traditional role of penetrator to be penetrated as well, he decided he was open to it after all.

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We started slowly and it took us many months to progress from a tongue to a finger to a small butt plug to fingers (plural) to larger butt plugs.

The ‘beginner’ dildo I'd found intimidated him, so I got a smaller one, and we gradually worked up to getting it inside him — guided first by his own hand, and then by mine.

Our first attempt at true pegging was during a threesome with a woman we call "Hot Mama." He’d gotten us both off several times, and I’d warmed him up with several fingers.

Walking back to the bed after strapping on, I caught my first-ever glimpse of myself in the mirror with a harness and penis.

I looked so hot!

When we were ready, he bent over the bed. Hot Mama performing oral sex at the same time helped convince him this was a very good thing, and we were all able to enjoy it for several minutes — until I got a little enthusiastic and thrusty and he had to call a time out.

Flick doesn’t actually enjoy direct pressure stimulation of his prostate, so the angle was a piece of the puzzle we hadn’t considered.

He played a bunch solo after our first attempt and worked up to enjoying the dildo on his own, so we decided to try again.

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This time we tried with him on top, so he could control speed and depth.

We went slowly, with me not moving until he was ready. When we got going, he ejaculated so hard he hit me in the eye (which thankfully closed in time) and sprayed the pillow next to my head.

Pegging still isn't a frequent act in our repertoire, but it is something we’ve both come to really enjoy. We even celebrated International Women’s Day Deadpool-style, with him riding me during a threesome with our friend Iris. She and I loved every subversive minute.

I’m thrilled pegging is something we can share. The experience feels especially intimate due to his unparalleled vulnerability during the act.

The partners we’ve shared it all enthusiastically agree.

Plus, if I ever meet any feminist heroes, like Abbi on Broad City, I can proudly exclaim, “I pegged!”

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Kat (she/they) is a sex-positive, geeky, Canadian, and pansexual. She's also a podcaster - On The Wet Coast Podast - and audiobook narrator for Cooper S Beckett's novels A Life Less Monogamous and Approaching the Swingularity. onthewetcoast.com @WetcoastKat on Twitter. Their first book - Yelling In Pasties: The Wet Coast Confessions of an Anxious Slut - is available on Amazon.com, Amazon.ca, Inkterra, and Kobo.

This article was originally published at Life on the Swingset. Reprinted with permission from the author.