Pegging: A Brief History and How-To

By Dr. Tiffany “K.”, Ed.D., C.S.E.

Pegging is all the rage right now. Thanks to the mainstream mentions of this once elusive act by films and TV shows such as Deadpool, Broad City, and Weeds, people want to know what pegging is and what it might feel like.

What Is Pegging?

Pegging is simply the act of donning a strap-on and penetrating someone anally. Previously, this was limited to a cis-male partner being penetrated by a cis-female partner, but the term has grown in inclusivity. The term pegging now encompasses any gender or non-binary partner being penetrated anally with a strap-on.

The fact is, anal sex is no longer about sexual orientation, but pleasure. It is something that anyone has the power to embrace and experience a meaningful and pleasurable experience if they chose to from anal stimulation. It can enhance sex, as well as the closeness in a relationship.

Where Did It Come From?

The term “pegging” was originally coined by Dan Savage in 2001, a renowned sex columnist. But, it was in 1998 that porn introduced the idea through the film Bend Over Boyfriend, which brought anal sexual satisfaction to the boyfriends of female partners. However, it wasn’t until the idea was brought up in films such as Deadpool (2016) and the TV series Broad City (2011) that pegging became more widely known.

In 2022, PornHub released insights reports specifically on pegging, showing that worldwide, “pegging” is searched over 3 million times each month. U.K. visitors search the term approximately 102% more than the rest of the world. In addition, men were 28% more likely than women to search for pegging, and those in the 55-64 age group were 36% more likely to search for pegging than other age groups.

With statistics like that, it begs the question: why the sudden enthusiastic interest? The answer seems to come from multiple factors.

The Pandemic Effect

With the sudden mention of the term in the mainstream, mixed with the pandemic forcing people to isolate with much more free time on their hands, curiosity seems to be a big driving force.

During the pandemic, there was a large increase in people searching the internet for sex: from porn to learning about themselves and their partners. Suddenly, communities in the world of sex, kink, and fetishes began to grow, leading to the discovery of what options existed for sexual gratification and play.

Quite Simply, It Feels Good

The anal entrance and canal have thousands of nerve endings. Those with a prostate also have thousands more nerve endings located within two bundles around the prostate itself.

Known by some as the P-spot (similar to the G-spot or G-zone in a cis-female), it provides ample opportunity for pleasurable stimulation. In addition, an orgasm by way of prostate stimulation can also lead to both an ejaculatory orgasm, as well as one without ejaculation, extending the sexual playtime. Many prostate owners have also found these orgasms provide more full-bodied orgasms than penis-centered ones.

Further, for those suffering from erectile dysfunction, prostate stimulation can provide pleasure, and even orgasm, without the need to stay hard. Pegging is one way in which the prostate can be stimulated, and for partners to enjoy sexual experiences if E.D. is a factor.

Pegging = Pleasure

Daniel Saynt, Pleasure Evangelist and Founder of We Are NSFW spoke with me to discuss his experiences with the sex act.

“I think it’s really sad that the majority of men living today will never experience penetration because of fear of judgment, shame, or internalized homophobia. I truly can’t have a serious conversation about great sex with a man who doesn’t appreciate his prostate.”

He continues, “The orgasms one discovers through pegging are similar to female orgasms, with varying degrees of waves of stimulating pleasure rushing through your body. While penile orgasms have a quick intensity, resolution, and [a] refractory period which could last hours, prostate orgasms slowly build up, intensify, subdue, intensify, and can be enjoyed for hours.”

Saynt adds, “As you become more advanced in your ability to excite your prostate, you unlock additional levels of orgasmic pleasure. There truly is no comparison… It’s sad that so many men fear it, some women judge it, and not enough people are exploring [prostate orgasms].”

Role Reversal

Those who are on the giving end of pegging report feeling a sense of empowerment through the act.

Ruby Ryder, Dominatrix, Educator, and pegging expert of Pegging Paradise loves pegging. She shares with her readers that it appeals as “…control is mine. I can tease him…or pound him…until he begs for release or respite. I can change the angle of my toy just a bit and know it’s driving him crazy with pleasure. Or I can stay still, buried inside him, and drive him crazy with wanting more. I am wearing the dildo, so I get to decide.”

However, pegging doesn’t have to be tied to kink, dominance, or submission. An entire subreddit called Pegging Unkinked exists to normalize and share content around anal stimulation without ties to BDSM. Every person with a prostate has the potential to enjoy stimulation, even if they identify as “vanilla.”

Strap-On Play and Gender Affirmation

For cis-women, they can “flip the switch” by taking on a dominant role with pegging. For non-binary or trans people, however, it can run deeper. They may feel a sense of affirmation through the act of pegging or being pegged, as so much sex concentrates on the act of penetration.

For trans men, the act of “having” or “wearing” a cock can help them feel connected to their masculinity. Jorah St. James, a transmasculine model, writer, and influencer based in NYC, agrees. He states, “I feel very affirmed when wearing a strap-on. It feels like an extension of my body, not just a toy that’s attached to me.”

They continue, “I am typically most mindful of my partner’s pleasure while wearing the strap-on. While I enjoy the optics and sensations of strap-on play, ultimately, I am most happy when my partner is happy. That being said, if I am feeling objectified while wearing the strap, it does taint the experience for me. I don’t like when it feels compulsory, or at worst – fetishistic.”

“When I wear the strap, it’s because I want my partner to feel all of me, and I want to feel all of them. I guess that’s a long-winded way of saying yes, I do find it affirming, but because I am very particular about the circumstances within which I will engage in that type of play.”

How To Tell Your Partner You Want to Try Pegging

While pegging is becoming more mainstream, it is never a good idea to don a strap-on out of the blue, ready for butt play. Communication and consent, just as with any other partnered sexual activity, is key.

If you and your partner already have strong communication skills and are open with each other about wants and desires, you can bring the conversation during a relationship check-in or when both of you are relaxing. If you feel comfortable, just ask: “I’ve been looking into the idea of pegging and would really love to try it with you. How would you feel about that?”

However, if conversations around sexual activity are still difficult, you can always bring up the idea as a hypothetical idea, something a friend had brought up, or something you read in passing, such as from an erotica or article. Use that as a segue to express interest in the idea. The conversation can spark from there, but it may take time for your partner to sit with the idea before they open up to the idea of trying it.

If your partner is not open to the idea the first time you bring it up, respect your partner’s boundaries. Don’t push them. There is always the option to reintroduce the topic down the road, but it may be an idea that needs time and research to develop into interest.

But if you’re ready to try it, let’s break down how!

Pegging 101

Hygiene First

Anytime butt play is involved, cleanliness is key. There is no need to go through the process of an enema unless you so choose to, but if you’d like to, here’s a comprehensive how-to guide. However, be sure if you need to poop before you get pegged, do so well in advance and clean the area well. A shower is always a good option with warm water and gentle soap.

In addition, you will want to ensure hands and toys have been washed with warm water and gentle soap, or a good quality toy cleanser, to ensure everything is squeaky clean. If you have longer nails, consider investing in a pair of latex opera gloves to blunt the tip.

You can also use a condom over your dildo to make post-pegging cleanup much easier. That being said, it’s a butthole, and shit happens. Don’t freak out about it, it’s natural and has happened to us all. There’s no harm in laying down a towel or preparing to wash and change the sheets after.

LUBE LUBE LUBE

Now that you’re all cleaned up and the toys are prepped and ready, bring out the lubricant. Lube is the single most important tool you should have in your toy bag. The booty is not self-lubricating: a condom alone will not have enough lube out of the packaging. For both safety and pleasure, lube is essential.

In most cases, use a water-based lube and ensure that your toys are compatible with water-based lube as well. Silicone and oil-based lubricants can cause issues such as erosion of the toy and breakage of the condom. If you have a silicone lube-safe toy (or a hand) and are not using a condom, silicone lubes may be more desirable. Silicone lubricants last longer and tend to be slicker than water-based, making it a fantastic option for any booty play.

Take it SLOW

I’ll be frank. The tissue around the anus and rectum are fragile and can be easily damaged due to tearing by penetration if there isn’t enough care and time given to the experience. According to the health care and sexuality organization Ro, taking it slow is vital.

If you are new to anal play or pegging, plan to set aside a couple of hours to help relax, get comfortable, and ensure that you will have uninterrupted time to fully explore the sensations and avoid trauma.

Before diving deep on a strap-on, it’s often best to start with oral or finger stimulation. Then, slowly move to finger penetration or a small toy such as a small butt plug. This help stretches the pegee out, and introduces the nerves to new sensations!

Toys

For first-timers, choose a strap-on harness you like and a medical-grade silicone dildo. According to Dangerous Lilly, a well-known sex toy critic, this means a dildo that is made of 100% silicone, hard plastic, acrylic, glass, metal, or other natural materials. Toys that contain phthalates should not be used for anal play. This includes materials like rubber, PVC, vinyl, and Cyberskin.

You should also assure the dildo you select that is compatible with your strap-on harness. Don’t be afraid to start with a toy marketed to “beginners.” These dildos are typically a bit smaller and smoother.

You will likely find a more customized fit by buying your strap-on and dildo separately rather than as a set. Plus, it gives you and your partner(s) more options.

Get Ready!

Talk about the process. Ensure that your partner understands it’s okay if the full experience of pegging doesn’t happen the first time. If you take pressure off the experience and allow pleasure to be the focus, when the moment arises, pegging will likely be a smooth and exciting experience for both of you.

There is no rush. Staying relaxed is important for anal penetration to be pleasurable. Take advantage of all the ways you can incorporate foreplay: oral, kissing, massage, and all the other juicy things that turn each other on.

Recommended Starting Techniques:

Trace the outline of the anus gently with a finger. You can also use a tongue, the tip of a toy, or if you’d like to explore sensation further, an ice cube or a feather!
When you and your partner are eager, relaxed, and ready, start to insert a small toy, like a plug, or a finger. At first, only go up to the first knuckle of the finger, slowly thrusting in and out of the anus. Easing into it is essential!
Continue to apply lube as needed. Even if you think there is enough, add more!
Once you can penetrate a little further past the first knuckle, try making a “come hither” motion against the prostate. This is about 2 inches inside the anus, along the front wall. This is also known as “milking the prostate” in which the prostate is being stimulated for sexual pleasure. This often leads to fluid or pre-ejaculate being released. Prostate milking is a great preclude to pegging, and also incredibly pleasurable on its own or alongside a handjob.

Try these techniques, and experiment with others, until the receiver is ready to try the dildo. This is especially important the first time, but foreplay is always essential! Likewise, always ensure the receiver is ready for any change in pacing, motion, or toy. There should not be any pain associated with the experience. If pain is experienced, stop and adjust. Never try to “gut it out” or “push through the pain.” Speak up and check in with your partner frequently. Tell them what feels good!

Aftercare

Post-pegging is a vulnerable time, particularly for those new to the experience. Emotions can run high, even if the receiver thought they were completely prepared for it at the beginning.

It can also be emotional for a non-binary, transman, or cis woman who dons a strap-on for the first time. They may be in a dominant role for the first time. Asking your partner how they feel and providing support is one of the best ways to help transition from sexual activity to peace and rest.

Aftercare should always include at least a check-in with your partner and ensuring their emotional and physical needs are cared for.

Some questions to ask might include:

“How do you feel?”

“How was the experience for you?”

“What did you like? What did you not like?”

“Is there anything I can do differently next time to make it more pleasurable?”

For the receiver, there may be physical aspects of aftercare that their partner should be aware of and ready to support. If there is any discomfort or soreness, a warm or cold cloth may help, a shower together to help wash away lube can be relaxing, or a gentle back massage to relax and relieve any discomfort.

Final Thoughts:

Anal sex can be a fantastic way to incorporate a new and pleasurable experience into your sex life. However, it is important that safety precautions are taken into account in advance:

Items used should be cleaned before and after: toys, hands, etc!
Allow ample time for the experience… the anus does not stretch or relax as quickly as other parts of the body. Your partner (or you!) will need time to acclimate to new sensations.
Before you start, have plenty of lube! Always use more than you think you need. Keep an extra bottle on hand – just in case.
Be aware of issues such as bleeding, pain, sores, lumps, bumps, or discharge before or following the experience, and seek medical attention as soon as possible if something arises.
It’s okay if pegging isn’t for you! Not everyone enjoys it, giver or receiver. There are plenty of other options if you find pegging isn’t for you.

Pegging, or any type of anal play, can be a fabulous way to enhance the sexual experience with your partner. Just remember to take your time, communicate clearly, and have fun!

Additional Resources:

Ruby Ryder, Dominatrix, Educator, and pegging expert of Pegging Paradise

Submissive Guide has a fantastic new book, Exploring Anal Pleasure that is comprehensive, detailed, and fantastic! Plus, its written by a fellow colleague and BDSM educator who I greatly admire as a professional in the field.

Pegging: A Brief History and How-To