F*ck Around and Find Out with Anna Lee: What’s the deal with pegging?

Welcome back to F*ck Around and Find Out with Anna! Can I just say, I’ve been LOVING the write-ins I’ve been getting lately. They've been getting more detailed and specific, and I’ve been having the best time reading them. I promise I’ll get to as many as I can, but I’ve also realized that sometimes I ramble and end up writing a full-on novel in response. I think this might be an aging thing. Both my mom and dad will keep talking at me, even when my eyes glaze over and become 80 percent closed.

Anyway, before I start rambling about my parents, let’s get into it!

Okay, can you please explain to me what’s the deal with pegging? - Matteo A

I’m so excited someone finally asked about this! Pegging has truly stood the test of time. It's consistently one of the most-asked-about topics in my inbox. Dare I say, it had a mainstream resurgence after that iconic Broad City season two episode in which Abby’s date, Jeremy, casually asks to be pegged on their first date.

But yes, I said “resurgence” because the first truly iconic public moment came in the form of a 1998 adult video called Bend Over Boyfriend, starring Carol Queen and Robert Morgan. It’s an explicit, educational guide to pegging—and honestly? Still a must-watch.

So, what is pegging?

Pegging is a sexual act during which a person with a vulva (typically using a strap-on dildo) penetrates their partner’s anus (typically someone with a penis). It’s often seen as “role-reversed” anal sex—meaning the receiver isn’t usually the one being penetrated.

While the act itself has probably existed for centuries (because, you know, if it’s a hole, it’s probably been filled before), the term “pegging” was coined in 2001. Relationship and sex writer, Dan Savage, ran a public poll to figure out what to call the act, and “pegging” beat out runner-ups BOB (bend-over-boyfriend) and “punt.”

I think it’s such a cool sex act that can bring immense pleasure for everyone involved and especially if the person being pegged has a prostate. It also taps into elements like trust, communication, power dynamics, and comfort, which makes the experience even more meaningful and hot.

Remember that anal pleasure has nothing to do with sexual orientation: it doesn’t make you gay, straight, bi, or whatever. It just means you like what you like. Just enjoy it, go slow, and use A LOT of lube.—like, whatever you think is the right amount of lube, do two extra pumps for good luck. 

I’m not fully sure how to word this or if it’s even something you can answer so I want to apologize for that up front😭, but basically I have only ever masturbated with a vibrator. I’ve probably been masturbating for four or five years now, before that I just never knew what to do. But I do want to figure out how to do it manually and still enjoy it, but I just don’t know how? Do you have any advice or tips and tricks on it? I’ve actually tried to look into this a few times over the years and each time I come up empty. I’ve tried a finger or two before and it honestly didn’t feel good until I used a couple fingers, but that’s also a lot going on at once and tired me out pretty quickly😂. I’ve heard of people using pillows, but I haven’t been able to figure that out. I think my biggest concern is that I’m training my body to only finish using a vibrator. And I know that oftentimes penetration alone isn’t enough to make women finish but I can’t help myself from wondering if the reason I don’t finish nine out of 10 times when sleeping with a man has to do with me only using a vibrator on myself? I’m also very new at sex, so that could be a factor too. In summary, got any tips?😅-RB

This is a great question and I know it’s one that a lot of people can relate to. In fact, I feel confident answering this because, same. 

The number one thing to remember here as we walk through some of my thoughts is, do not panic! Your brain is a smart little thing that likes routines and habits, and if you’ve built a strong, pleasurable association with your vibrator, of course your brain is going to lean into that! But the amazing thing is that your brain is also very capable of learning new things.

I also had a moment a few years ago where I had found a bullet vibrator that I just absolutely fell in love with. I found myself grabbing it every single time when I was masturbating and one day I realized that I was having a hard time getting to an orgasm with my hands, my partner, and even other toys.

And here’s the key: vibrators are machines. They’re designed to do things our fingers (and even our partners) can’t manually do as efficiently—they vibrate, suck, and thrust beyond what humans can do. So yes, it’s absolutely possible that your body and brain has gotten accustomed to orgasming with a vibrator because you’ve created a really positive association with a vibrator. But, the good news is that research shows there’s no such thing as permanent “vibrator dependency” or damage. That’s just an old myth meant to shame people for using toys. You’re totally fine. You’ve just built a really strong sensory pathway, and now you’re curious about building new ones.

When I decided to explore orgasming without my trusty bullet, I focused on three things:

1. Putting the vibrator away (temporarily, not forever!)
2. Using slow, intentional strokes with my fingers—circular or up-and-down motions on the clitoris
3. Taking my sweet, sweet time to build up arousal

I also recommend setting aside time to explore what turns you on mentally because, yes, orgasms involve touch, but they’re also super mental. Watch something sexy, read erotica, fantasize and get yourself so turned on that you’re focused on the experience, not the orgasm. That removes the pressure and helps create new positive associations with different types of touch.

Now, I also have to mention for anyone else reading, you don’t HAVE to know how to get to an orgasm with your fingers or manually with a partner. This advice is only if you WANT to explore, (or sexplore, as I like to say), and see other methods you can experiment with. I’ll forever be an advocate that vibrators are collaborators, not competitors and they always should have space in the bedroom, with or without a partner, if it brings you happiness and pleasure!

You’ve got this, RB. Give yourself grace, take your time, and have fun with the process.

I promise you that there is truly NO question too unhinged for F*ck Around and Find Out with Anna Lee. Have a question you’d like me to answer for the next article? Submit them anonymously here!