Written by Jen Schwartz, Lovehoney Editorial Team

Medically reviewed by Dr. Megan Fleming

How to Peg Someone: The Ultimate Beginner’s Guide to Pegging

Your journey towards becoming a pro pegger starts here.

In recent years, it appears that the topic of pegging has taken the world by storm, with the sex act making prominent appearances in popular media, gracing screens both big (think Deadpool) and small (think Broad City). The latter’s pegging-centric episode actually caused a surge in Google searches for the term ‘pegging’ shortly after it initially aired in 2015.

Whether the cause is better representation in film and television, a societal shift towards promoting sex-positivity and healthy sexual exploration, or a combination of the two, one thing is for sure: the act of pegging (or at least conversations surrounding it) is more popular than ever before.

What is Pegging?

‘Pegging’ describes the sex act of one person anally penetrating another with a strap-on dildo. The term was coined by author Dan Savage in his sex advice column, “Savage Love,” in 2001, initially being specific to vagina owners being the penetrators and penis owners being the ones on the receiving end. The word has since evolved, as words tend to do, to be more inclusive for all types of gender identities, anatomies, and relationship dynamics. We love a good sex glow-up!

The Appeal of Pegging

The reasons people love pegging are as diverse as the individuals who partake or want to partake in the act. Physical pleasure is a significant motivator for many when it comes to sex, pegging included. The anus and rectum consist of about a bajillion (not literally, please don’t @ me) nerve endings that feel fab when properly stimulated, which pegging has the power to do.

For some, the appeal of pegging stems more from their minds. In instances where a vagina owner is penetrating a penis owner, the role reversal can be quite a thrill, allowing both parties to explore new ways to play. Perceived power dynamics that assume penetration is a dominant action and that being penetrated is a submissive one can also be a turn-on for peggers and their partners, making the sexual activity commonplace in the BDSM community.

The Art of Conversation: Discussing Pegging with Your Partner

If you’re interested in pegging your partner, the first step to potentially living out your fantasies is to let them know! As is the case with any intimate conversation, you should be considerate of timing and setting before approaching the topic.

It’s best not to broach the subject right before or directly following sexual activity. Revealing your desire to peg your partner just prior to getting busy can result in pressure for them to agree straight away, while bringing it up immediately after sex might make them feel like their performance and your sex life as a whole with them is lackluster. Instead, choose a moment when they’re not vulnerable and the mood is not sexual. In terms of location, you’ll want to be somewhere private where you both feel safe physically and emotionally.

While it may come naturally to ramble on about how hot you find pegging and why it’s such a turn-on for you, be sure to leave room for your partner to share their thoughts on the matter. Address their concerns and answer their questions to the best of your ability.

Navigating Consent and Boundaries

Whether your partner says yay, nay, or may-bay, it’s imperative that you respect their decision and don’t pressure them about changing their mind if their answer isn’t the one you were hoping for.

If your partner says “no” to pegging:

Thank your partner for listening and let them know their aversion to pegging won’t negatively impact your relationship. Sharing fantasies can be vulnerable, but it can be equally nerve-wracking to tell your boo you’re not up for a sex act they’re super interested in. Reassure them that you respect their boundaries and don’t bring up the idea of you pegging them again unless they start the conversation.

If your partner says “yes” to pegging:

You’ll now want to have an in-depth conversation about your future pegging sesh to ensure all parties are as comfortable as possible, manage expectations, and make your first time go as smoothly as possible. Discuss what the ideal pegging experience looks like for you both, and ask what you can do before, during, and after pegging sex to make them feel most at ease and cared for.

Safety First: Precautions and Tips for a Healthy Pegging Experience

We’re all adults here, so I think we can admit that sex isn’t without its risks - this is especially true regarding anal play.

Minimizing the risk of running into fecal matter

No ifs, ands, or butts about it: when it comes to the rectum, shit happens. I mean, that’s literally what it’s there for! But you probably don’t want said shit to happen in a pegging sesh, and there are ways to prevent messy situations.

The receiver should have had a bowel movement within the last 12-24 hours pre-play. It’s important that they thoroughly cleanse their anal area after their last poop - this could be as simple as washing the exterior with water and mild soap or as extensive as using an anal douche. Either will work - the choice really just boils down to the pegging participants’ preferences and comfort levels.

If you do choose to use an enema, do so at least one hour prior to anal play or you could increase the chances of encountering fecal matter. Check out our guide on How to Use an Anal Douche for more enema tips!

Even with the best precautions, there’s no foolproof way to guarantee fecal matter or residue won’t sneak its way into your playtime. If a mess or accident does occur when you’re pegging someone, don’t be an ass about it. Clean up, reassure your partner that this natural bodily function doesn’t make them disgusting, and try again another time.

Preventing infection and STI transmission during pegging

Like all other forms of sexual activity, pegging can result in the spread of sexually transmitted infections (STIs). You can reduce that risk by taking the following actions:

  • Knowing your and your partner’s STI statuses and making medical decisions based on that information, such as taking medications like PrEP.

  • Using safer-sex barrier methods like condoms and dental dams for your bodies and any sex toys you use together.

  • Not sharing porous strap-on dildos with different partners or sticking exclusively to non-porous dildos that can be disinfected.

And STIs aren’t the only type of infection you can get from sexual activity, either, which is why it’s important to thoroughly wash your sex toys before and after each use.

Pain and injury prevention

Pegging doesn’t have to be painful for the receiver - in fact, it shouldn’t be! Plenty of lube (that’s compatible with the materials of your strap-on dildo), patience (don’t go 0 to 100), and an appropriately sized sex toy for the receiver’s anal experience level will help keep your pegging experience healthy and pain-free for all parties.

Though it may be tempting for nervous first-timers, avoid using numbing agents that reduce sensitivity. Pain and discomfort are your body’s way of telling you to stop or slow down. By ignoring those signs because you aren’t aware of them, you could sustain an injury.

Gear Up: Essential Items for Your Pegging Journey

While it’s up to you and your partner to decide which intimate products you’d like to bring to the pegging party, you’ll, at the very least, need a strap-on and lubricant to play.

Strap-on harnesses

There are two main options when it comes to strap-on equipment: traditional harnesses (paired with compatible dildos) and strapless strap-ons.

Harness-style strap-ons are a better option for newbie peggers as they’ll securely keep your dildo in place so you can thrust away without worry. Naturally, you’ll want a harness that fits your body type, so be sure to check the product’s dimensions and size guide before committing to one. Your harness must also work well for your anatomy, so don’t forget to check whether a certain style will work with what you’ve got going down below the belt.

The best traditional strap-on harnesses

Some strap-on harnesses come with one or more compatible strap-on dildos. These convenient bundles are known as strap-on kits and are a great fit for beginners looking to quickly build their pegging toy collection. Strap-on kits may also appeal to those who get overwhelmed by choices and would rather spend their time pegging than researching which individual harness and individual dildo they should get for said pegging.

The best strap-on kits

Strapless strap-ons allow peggers with vaginas to easily achieve their own stimulation from the vaginal insertable portion of the sex toys. This strap-on style is also ideal for realism as it makes the strap-on dildo feel like an extension of the wearer’s body.

The best strapless strap-ons

Strap-On Dildos

A strap without a dildo is like a library without books - pretty damn useless. The main difference between standard dildos and strap-on ones is that strap-on dildos will have some sort of flared base that allows them to insert into harnesses. That being said, not all strap-on dildos are compatible with all strap-on harnesses - their compatibility depends on the size of the harness’s O-ring or other opening and the girth of the dildo’s base.

Just as the case is with dildos as a whole, there is a wide variety of strap-on dildo styles available to suit your needs - vibrating, realistic, non-representational, petite, large, hollow, solid, and curved for G-spot and P-spot stimulation, to name just a few. Pegging beginners will likely want to start with a small strap-on dildo, as it will be easier for the wearer to wield and for the receiver to take.

The best strap-on dildos for beginners

Lubricant

Since the booty is not a self-lubricating orifice, it needs a little (actually, a lot) of help achieving the slickness that’s required for healthy, comfortable penetrative sex. Failing to use lube can make your pegging sesh painful at best and physically harmful at worst (hello, anal fissures!). Since it’s unlikely that pain and injury are on your pegging wishlist, be sure to coat your strap-on dildo and the receiver’s hole in a generous heap of lube, and don’t be shy about reapplying mid-peg! The best lube formula choice for pegging will be long-lasting and compatible with the materials of your strap-on dildo.

Preparing for the Main Event

Before you and your partner get to heavy petting and beyond, you should first have an open dialogue regarding pegging expectations and preferences. Discuss what you hope to both get out of it and what you can do as a couple to make each other more comfortable during the moment.

Next up comes the touchin’! While foreplay is crucial to the enjoyment of both parties, being properly aroused and warmed up is particularly critical for those on the receiving end of a pegging session. In order for their booty to safely and pleasurably accept a strap-on dildo, the receiver and their b-hole will need to be super relaxed. Consider giving them a full-body sensual massage that eventually transforms into an anal massage to set the mood and prepare their ass for pleasure.

Once you’ve moved onto ass play - whether that be through massage or other foreplay techniques - be sure to give their booty plenty of lovin’. Rimming, anal fingering, and anal massages are all great tactics for pre-pegging anal stimulation.

How to Peg Someone

Now that you’ve got consent and the tools of the trade on hand, you’re finally ready to turn fantasy into reality.

Step 1: Strap up

We’re not gonna lie to you - putting on your strap-on harness and attaching your chosen dildo to it can be a little awkward as it’s not a seamless process, especially if it’s your first time doing so. You can make the whole experience a little bit sexier by looking at your strap-on equipment as a form of functional lingerie and putting it on pre-play so your partner doesn’t see you fumbling with your strap-on in the event that you have a little trouble with it.

Already having your strap-on on when it’s time to get saucy can also be a turn-on and allow you two to utilize it in foreplay. Think of how hot it could be to pull down your pants or lift up your skirt to reveal your ready-to-use strap! You can even have your partner treat it as if it were your cock, stroking, kissing, and sucking on it before getting down to business.

Step 2: Turn up the heat and stretch that butthole

Foreplay, and especially anal foreplay for the receiver, are a key element of mutually satisfying pegging experiences. Pegging is not on the list of quickie-friendly activities, so take your time to arouse both yourself and your partner before enacting full-on strap-on anal sex.

Keep in mind that the strap-on dildo should not be the first thing to enter the receiver’s anus. Start slow with a well-lubed finger and consider having them wear a butt plug during foreplay to prepare their butthole to safely and enjoyably accept larger objects.

Step 3: Penetrate and peg

Once everyone is revved up and rearing to go, you can move on to the moment you’ve been waiting for: pegging your boo! Before actually inserting your strap-on dildo into their booty, be sure to apply a liberal coating of lube to the sex toy and their anus. With your dildo and their hole slick and slippery, begin by very slowly penetrating your partner’s butthole with the head of the dildo. Let the dildo remain stationary for a minute or two, allowing their asshole to adjust to the girth of your toy. You can then progress to sliding more and more of the dildo inside them, again letting it rest for a few moments once they’ve taken as much as they want or plan to before employing any thrusting action. When it comes to the thrusting itself, go slow and let the receiver set the depth and pace of penetration.

How to Increase Pleasure for the Wearer

Strapless strap-ons aren’t the only way for peggers to add some stimulation for themselves! Vibrating dildos are a fab way to add some buzz for both parties, or you can place a vibrating cock ring on your dildo to instantly transform it into a vibrator. Vagina owners may enjoy positioning a strap-on dildo’s base over their pubic mound to indirectly stimulate the internal portion of their clitoris or adding a stimulating strap-on cushion to the base that rubs against their vulva. And then there are sex toys you can add that are unrelated to strap-on play, like butt plugs and nipple clamps.

Toys to please peggers

Pegging Tips for Beginners

Want to peg like the best of them? You gotta start slow before you can go pro!

TIP 1: Practice makes perfect

Wearing and yielding a strap-on can take some getting used to. You’ll likely feel more confident (and be more successful) in your pegging adventures if you do some solo exploration first. Try on your harness and adjust the straps to your comfort level so there are no set-up surprises when you get to the real thing. Don your strap-on equipment around the house and familiarize yourself with how it feels to wear and move about with it on. The more comfortable you are operating your strap-on on your own, the more comfortable you’ll be operating it around others.

TIP 2: There’s no such thing as too much lube

Lubrication is critical in all forms of penetration, and since the booty doesn’t produce any naturally, you’ll want to make sure you have plenty of the store-bought kind on deck for pegging sessions. Apply a hefty amount of lube to your strap-on dildo and your partner’s anus pre-peg and reapply throughout as needed.

TIP 3: Start small

Ain’t no shame in the giant dildo game, but you’ll want to choose something much, much smaller for your first few trips to Peg City. An XXL dildo can be both intimidating and painful for pegging newbies, so be conservative in size choices when starting your pegging journey. You can always move up the size ranks later as you and your boo gain more experience!

TIP 4: Be patient and gentle

Pegging is a journey, not a race. No matter how excited you and your partner may be, it’s important to take your time, engage in plenty of foreplay, and be slow, smooth, and gentle when it comes time for penetration. Your first foray into pegging isn’t the time for power thrusting! Trust the process; you’ll get there when you’re both ready.

TIP 5: Talk it out

No, we don’t mean dirty talk (though you can incorporate that, too!) You should communicate with your partner before, during, and after pegging fun to ensure safety and comfort for all. Discuss what your expectations are before you begin. Check in often during the act and ask if they want you to change anything about your technique. Have a chat afterward to determine whether you two would like to explore pegging again. The more communication you have, the more joyous your sex life will be!

Don’t Forget Aftercare!

Your job isn’t done when the pegging fun ends - a healthy pegging session requires a few actions after the fact to keep all parties feeling their best, both physically and emotionally.

In terms of physical aftercare, cleanup is key. Thoroughly wash any sex toys used and yourselves to get rid of any lingering bacteria that may cause infections.

For emotional aftercare, reflect on the experience with your partner and discuss what they liked and disliked about it. Be sure to ask them how they’re feeling and if there’s anything you can do for them. Being on the receiving end of pegging can make someone feel quite vulnerable, so soothe your partner with words of affirmation and snuggling if they’d like you to.

Peg On (Or Don’t!)

You may find out post-peg that the sex act isn’t right for you or your partner, and that’s totally okay! There are still plenty of passionate play types left on the menu. But if you two do thoroughly enjoy your first foray into the world of pegging, get excited because there’s much more to explore! Once you’re comfortable with the act itself, you can experiment with different types of positions, harnesses, and strap-on dildos - the options are endless. Just remember not to rush through to next-level pegging toys and practices - the best things in life are worth waiting for.

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