Everything You’ve Ever Wanted To Know About Pegging

In the fourth season of The Bold Type, there’s an episode called “To Peg Or Not To Peg.” Spoiler alert: In it, Kat Edison participates in pegging for the first time. Her review? It was “intimate.” 

“I don’t know if that was just because I was in a place of power and he was vulnerable… But we connected,” she says. Kat isn’t alone: Plenty of people find pegging sexy and even empowering. If you're intrigued, the guide below can help you get started. 

It traditionally involves someone wearing a strap-on dildo to penetrate the anus of a person with a prostate. The term really came into the zeitgeist on 21st June 2001. It was the winning entry of a contest Dan Savage hosted to name the sex act. One of the some-12,000 folks who voted in the competition included a detailed case for the term: “Consider: Pegged. Pegging. Pegger. Peggable. Sir Pegged-a-Lot. Soft peg/hard peg. Feeling a bit peggy. Peg me, dammit. Not tonight, I've got a peg-ache,” they wrote. 

While originally, the definition relied on the gender binary (a woman pegged a man), our understanding of sexuality and gender have evolved since 2001, which has changed our relationship with the word, explains Luna Matatas, sex and pleasure educator. “We know that anyone, even people with penises, can strap on [a dildo] and anyone, even people without penises, can receive strap-on play.”

It's not for everyone — but those who dig it say it's divine. The prostate is a “pleasure nerve hotspot,” says Ashley Manta, a sex educator and the founder of CannaSexual. “Having it stimulated, particularly having something rubbing up against it, often feels really fantastic,” she says. “The anus and the sphincter and the rectum are also all teeming with nerve endings, and the feeling of being stretched and filled can be fantastic as well.” 

The experience isn't all about the receiver, either. While pegging doesn't have to be about submission and dominance, it can be a tool that people use to get into those mindsets,” Matatas says. 

“This is a time when I get to feel what it’s like, as someone who doesn’t have a penis, to be the penetrator, and it makes you feel power,” Manta says. “I believe we all have an energetic cock and pussy, and the energy of penetration can flow in the dildo. You can feel real pleasure from the sensation of grinding into your partner.” In some cases, you might even have energetic orgasms, even though the dildo isn’t a part of your body, she says.

Choosing a strap-on or dildo that is designed to hit your clit can increase the pleasure the giver feels. 

A dildo with a base that is strapped into a harness, and lube to apply inside the anus as well as on the dildo. Silicone-based is preferable because it's long-lasting, but it will damage silicone-based dildos, so in that case, stick to water-based lube. “You could even use coconut oil, but remember that spit is not the same as lube,” Manta adds. Unlike the vagina, the anus is not self-lubricating; pegging without lube can be painful at best, and can even cause serious injury.

You’ll also probably want to lay down a towel on the bed, as things could get messy. “When you’re playing with the ass, well, shit can happen,” Manta says. Matatas recommends using a condom on the dildo for easy clean up. A mild enema with water or saline should be safe, though you should check with a doctor before using one. Don’t try to “clean” your anus with any alcohol-based solution. This can dry out the delicate tissues inside the anus and make it more susceptible to micro-tears,” Matatas says

It can be difficult to relax anal muscles, but it’s important not to use any agents that would actually make you numb, because pain is your body’s way of telling you that something is wrong or isn’t working correctly, Manta cautions. 

First, foreplay. “Warming up is critical for pleasure and preventing pain,” Matatas says. “We want lots of blood flow in the body via arousal and we want our partners to be relaxed and feel safe.” She adds, “A few minutes isn't enough."

Start with a small dildo. If you're the pegger, the first time to put it on is not right before foreplay; slip it on ahead of time to make sure it fits and you know how to use it. “Put on that harness and the dildo, and do some air thrusting in the mirror,” she suggests. “Squat with it, dance around with it. Get playful with it and shake out any awkwardness."

When you're ready to start, have the pegger lie on their back and the peggee ride the dildo. This gives the receiver more control to go at their own pace. Doggy style has a similar benefit.

Communication is key. Especially during the first few attempts, the giver should keep asking the receiver, “How does this feel? Do you want to go faster or slower? Should I go deeper or shallower? Do you want me to stay in or go in and out,” Manta suggests. She says receivers speak up about what feels good and what doesn't. You're giving your partner “cheat codes to your body,” she says. 

Don't push past pain, Matatas stresses. “It might mean your posterior has had enough for the night or it might mean you need more lube or to take a break and get the body more aroused and relaxed,” she says. As Manta puts it: “The ass can be a barometer for how relaxed you genuinely are.”

If it doesn’t work, it doesn’t work. In that case, don’t stress out, and go with plan B. “Do things that feel good, scissors, cuddle, do something else, and let that be okay.” 

But you might experience a different kind of pain. If you're new to the practice, the first few times you might get “real tired, real fast,” Matatas says. “We are using the lower back, hips, glutes, and even hamstrings in thrusting,” she says. “If you find that your body just doesn't get used to pelvic thrusting, remember that you can peg with all kinds of harnesses — there are hand harnesses, thigh harnesses and even boot harnesses. Don't be afraid to experiment —  and have fun.