Lessons in Pegging

How I learned a sexual term I hadn’t heard used before and realized it’s something I’d be interested to try

I have a friend who sends me dick pics on the regular to great comedic effect.

Whenever I need a good laugh, he sends me Dick van Dyke. Or another famous Dick. And I appreciate that more than any personal anatomy photos someone else might send.

He’s the only person who’s ever dick pic’d me, and I appreciate that, as well.

I decided to reciprocate one day with a dick pic of my own. I debated between two memes and went with this one:

It suited him since he’s the one who was leading me on for a while there. But, I digress. We’re good now, and can dick pic each other without making the other uncomfortable, so that’s all that matters.

When I sent it to him, I said, “Now you can say you’ve been dick pic’d by a chick.”

His response: “I believe the term is ‘pegged.’” Then he added: “Pic pegged.”

What The Heck Is Pic Pegged?

I was at work at the time he replied and couldn’t play around in the Google machine (my favorite pastime), but once I had time to look up pegging (I just knew that if it was something he said to me, it would be NSFW) and specifically pic pegging, I was all over it.

So, truth be told, I didn’t really know what “pegging” was.

Despite reading and writing erotica and sex stories on the regular, I tend to stick with what I like to read and what I write, and I suppose I’ve never ventured down the pegging avenues, although I did know it was a thing. I just didn’t know the term for it.

So, as per my usual, I hit the Google machine…once I left work, of course.

One of my first hits was about an AI-powered Microsoft tool that “pegs” photos with facial emotions. Funny (and creepy!), but I doubted that’s what my friend meant.

The next hit had a great graphic of “Keep Calm and Get Pegged,” which I thought held promise of an explanation of what my friend meant, but it turned out to be about being pegged or categorized as a musician.

Considering my friend’s predilection towards sexual innuendo and content, I highly doubted what this meant.

Seriously, Google, why are you showing me posts about pants or concrete and wood? I wanted a sexual definition, not whatever this was:

OK, Where’s the Sexy Pegging Content?

At this point, I was beginning to doubt my Google-fu. Usually I can find the weird, which is probably linked to my history of Googling the weird.

I changed my Google search from “pic pegged” to “pegging.”

Oh, that’s where you’re hiding, sexual pegging content!

The first hit was a snippet from an article entitled “Six men open up about what it’s like to be pegged by women and why they loved it.”

Here’s the snippet quote which told me a lot more than my previous search hits did: “Pegging describes the act of a woman penetrating a man anally with a strap-on. Mar 26, 2019”

Thank Google! You usually come through for me.

Now I knew I’d read about this and watched some porn in this vein but hadn’t known the term. I felt armed and mentally prepared to learn more and so I read the above article about six men’s experiences with pegging, which was, as expected considering the website, fairly tame.

So I kept scrolling to see what else I could find out.

Next up, I found a funny meme page tagged with pegging, but, interestingly, only the one applied to the sexual connotations:

I guess I won’t continue to learn to speak meme as a second language with pegging.

Why Didn’t I Start With UrbanDictionary.com?

I’m not sure why I didn’t originally start by looking up what UrbanDictionary.com had to say about pegging. It’s usually my go-to resource for all things that are beyond my current scope of vocabulary, especially in the sex world. I must be out of practice.

And, as always, Urban Dictionary did not disappoint. My favorite is the explanation by DI about the origins of pegging:

I have no idea if this is true or not about pirates. I so desperately want it to be true that I refuse to fact-check and Google further. Sometimes the “truth” found on Urban Dictionary is enough for me.

Pegleg pirates initiated pegging. Noted for future cocktail party fodder.

What Are The Best Positions For Pegging?

A common question I found was about what positions would work for pegging. Since I’ve watched possibly more than my fair share of gay porn, this seemed obvious to me. But then I realized that not everyone has.

So my next thought was: whatever position feels the most comfortable for both parties involved.

This article in Men’s Health gave some options. Not sure what makes them mind-blowing, but that’s for a headline analyzer to pick apart, not me:

I’ve Never Pegged Someone. What Does It Feel Like?

Although I’ve played around with some butt stuff, I’ve never used a strap-on or dildo on a guy. I’m not opposed to it. It just wasn’t something that occurred to me to try when I was in a serious relationship.

But that doesn’t mean I’m not curious: what would it feel like being the one who’s doing the doing?

I read the following article with interest, paying close attention to who brought it up and how it felt:

After reading this quote from the Cosmo article, I got the appeal immediately:

“Every time I did something he liked, I could feel all his muscles squeezing around me. It was really intimate and sexy. My absolute favorite part of it was just watching him enjoy himself, especially because I found it to be a huge turn-on that he’s so comfortable with his body despite all the negativity and shame around straight men enjoying anal stimulation.” — Diane, 38

Who wouldn’t want to make their partner feel that kind of good? Sounds like a super sexy way to get both of you going.

If I Like Pegging, Does That Mean I’m Gay?

This question of whether or not someone is gay because they like pegging is something that came up in almost every article on I read.

What’s with the sexual hangups? I’m of the mindset that sex is sex and you like what you like. As long as it’s between consenting adults, then have at it. Don’t worry about labels. Just enjoy!

Seriously, if you like a woman inserting things in your butt, it doesn’t mean you’re gay. It means you like having your prostate stroked. What’s gay about that?

And really, what’s wrong with making your prostate — and your partner — happy? Happy butts all around!

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