What Getting 'Pegged' Really Feels Like, According to a Sex Educator and a First-Timer

Pegging is a sexual practice in which a person, typically a woman, uses a strap-on to penetrate their male partner anally. The term was first popularized back in 2001 by the writer Dan Savage in his Savage Love sex-advice column. 

Decades later, pegging remains a popular fantasy among men and women. Keep reading to find out what pegging feels like, according to a man who tried it, and learn a few tips if you want to try pegging for yourself.

Pegging is a form of anal sex in which one person, typically a female partner, penetrates her male partner anally with a strap-on dildo.

However, while the term was originally intended to describe a cis woman penetrating a cis man, it has become much more inclusive and accessible to all genders and orientations. The main distinction between pegging and other forms of anal sex is that it involves anal penetration via a strap-on dildo.

Eric Barry, a Philadelphia-based comedian and writer, got pegged for the first time when he was twenty. But it wasn’t something he’d been dying to try. “It was not on my mind at all,” he says of pegging. “But my summer-fling girlfriend, who was 19 at the time, was exceptionally more experienced than me.”

She introduced Eric to BDSM practices — including restraints to role-play — and when he brought up his desire to have anal sex with her, she said that if he was going to penetrate her, she wanted to do the same to him.

How to Prep for a Pegging Experience

Before trying out pegging, it’s important to mentally and physically prepare. Going into the experience, Eric felt nervous. He spoke with some friends who were more experienced with anal sex, and they advised him to douche before anal play, so he made a “very specific trip” to the pharmacy.

He also accompanied his girlfriend to buy the necessary equipment. They shared the cost of the harness and dildo, which he decided to gift to her when they eventually broke up. 

Reflecting on the experience after the fact, Eric recommends newbie peggers to start with a smaller dildo.

How to Start a Pegging Session

The day of the pegging encounter, Eric and his girlfriend got started with foreplay, which is a smart precursor to any sexual activity—but particularly in this case. “Foreplay is key for all anal,” he says.

He says she adjusted the strap-on carefully, making sure everything was in place before getting started. As she poured lube directly from the bottle onto his perineum, his initial thought was that it was too cold. He wished she’d warmed it with her hands and breath first. She then used her fingers, a toy, and oral stimulation to help his body adjust.

Using a high-quality lube makes the pegging experience more comfortable because the rectum doesn’t lubricate itself naturally. And in the case of anal sex and shared sex toys, lube also reduces the risk of condom breakage, which can lower the likelihood of contracting an STI.

After Eric’s girlfriend used her fingers, tongue, and a butt plug to prepare his body, she lifted his legs and penetrated. 

Does Pegging Feel Good?

Getting pegged was overwhelming for Eric, but “not in a bad way.” He says his thoughts raced as she began thrusting, and he felt a mix of astonishment, exhilaration, and bewilderment. 

What he didn’t enjoy was the sensation of feeling like he needed to have a bowel movement. But as he breathed, he reminded himself that the sensation was caused by the dildo and not his bodily functions.

Would You Do It Again?

Twelve years have passed since Eric tried pegging. And though he’s open to the idea of doing it again, he says it’s not something he’d suggest on a first date. There are many more sexual acts higher up on the list for him. He notes that his preferences in the bedroom tend to lean dominant, and some partners may not be as open to role reversal.

Like the other genital organs, the anus is home to a dense network of nerves, which respond to sexual stimulation. The anus is also the entry point to the prostate, a walnut-sized gland that sits under your bladder and above the muscles that make up your pelvic floor. Some refer to the prostate as a man’s P-spot, supposedly comparable to a woman’s G-spot. 

One of the prostate’s main jobs is to produce prostatic fluid, which makes up part of your semen. However, stimulating the P-spot may also feel sexually arousing. In fact, some men find that so-called prostate-induced orgasms are more powerful and pleasurable than penile-induced orgasms.

Though many people practice pegging for the physical pleasure of the act, others in hetero-cis dynamics may enjoy the reversal of gender roles and the power play that pegging involves. Some view the sex act as a form of BDSM, in which the giver takes on the dominant role and the receiver plays the submissive.

This reversal of gender roles can also lead to more intimacy between partners. Studies have shown that pegging is associated with significant relationship benefits, including enhanced communication, trust, and mutual pleasure.

If you’re hoping to have anal sex with your female partner where she’s on the receiving end, letting her penetrate you first is a great first step. “Heterosexual women are more likely to trust a man who has been penetrated because he'll viscerally understand the need for warm-up and lubrication more than a man who's never been penetrated,” says Paul Aaron Travis, an AASECT-certified sex educator and founder of The School for Love.

Eric thinks there are many reasons why some men are afraid of pegging. The unfamiliar sensations, needing to do the bathroom prep, and buying the right equipment are just a few potential barriers.

But he also says that many men who have sex with women are simply used to being seen as the "doers" and “instigators” of sex. Because pegging places them in a more submissive role, it can feel like unfamiliar territory. Men who are interested in pegging may also worry about their female partner's reaction, particularly if she's not comfortable with him exploring different aspects of his sexuality.

Even more, the pegging experience may not be as fulfilling for the pegger, even if she’s suggesting it. “Given the mechanics of the dildo and harness, barring a double-sided dildo and vibrator harness pouch, the purely physical pleasure for the women pegger tends not to be great,” says Eric. “There can be an element of ‘why are we doing this when we have a better way for both of us?’"

However, according to Travis, while some women may quickly lose interest in being a pegger because they don't have nerve endings in the artificial phallus, they may still be willing to share the experience to provide their partner pleasure.

To peg or not to peg? If you’re curious but nervous, you’re not alone — and that’s perfectly normal. You don’t have to go all in right away. Starting with gentle anal play using fingers, external stimulation, or small toys can be a helpful way to explore what feels good and get used to new sensations.

“Stay engaged, take your time and practice,” he says. “Even if it’s not your thing, it’s fun to find out either way.”

If you’re still on the fence about pegging, then take some time to reflect on whether or not this sexual activity is for you. You should never agree to a sex act you don’t want to do, and your partner shouldn’t pressure you to abandon your sexual boundaries.

If you’re looking for more ways to enhance your sex life, try a different sex position, learn more about your erogenous zones, and explore this guide to prostate massagers.