Pegging 101

For the sexually adventurous, the term “pegging” seems like it’s been around forever. What else would you call a person without a penis anally penetrating someone with a penis with a strap-on dildo? Pegging is the only term we’ve ever used for that, and both the word and the sex act continue to withstand the test of time.

But let’s be real — people have been pegging each other for far longer than we’ve had a term to describe it. While people have been pegging and getting pegged forever, and even more have fantasized about doing it, the word itself is of fairly recent origin. 

The term “pegging” emerged because of noted sex columnist Dan Savage, author of Savage Love, a weekly sex advice column published nationwide. Savage took a reader poll in 2001, asking, “what the heck should we call this thing so many of us do, and even more of us want?”

The term pegging reigned supreme with a 43 percent edge over its challengers, though we’re old enough to remember considering voting for “bobbing” or “punting.” Imagine calling it that now, especially because it’s such a trending term! 

Pegging is a feel-good way to explore multiple fantasies simultaneously, with the bonus of an even more spectacular orgasmic potential for the peg-ee. 

But many folks, potential peggers and peg-ees alike, are still nervous about taking the plunge. We've got you if you’re here, reading this article with excitement and anxiety. Pull out the lube, warm up that booty, and get ready to finally let go of that stigma and get your peg on.

Why Peg?

Oh, there are so many reasons. For the recipient (the “catcher”), pegging is a great way to get one’s prostate well and truly pleasured into psychedelic, orgasmic bliss. It’s also an exploration of a physically submissive role that people with prostates usually don’t get to enjoy and people without prostates take for granted. 

We’re in the 20th century now; it’s time to switch up those outdated gender roles and stereotypes. Do what feels good!

As for potential peggers, many have wondered what it’s like to have a penis — here’s your chance. Pegging as the top is a much more common fantasy than you’d think, considering that dildos don’t have nerve endings — a fantastic illustration of the principle that themind is the largest sex organ we have

And yes, pegging is a highly gendered activity. That is a substantial part of its appeal. We could get into the weeds here talking about patriarchal power constructs and the phallus as a metaphor and so forth, but we’d prefer to get you two into bed instead — fortunately, that’s our job.

Does Pegging Make You Gay?

Alright, before we dive into the details, we have to address the elephant in the room. Does getting pegged make you gay, especially if you identify as a cis-gender heterosexual man? While the idea may make you laugh at first, it’s a very real dilemma that many straight men deal with every day when trying to come to terms with their kinks and desires.

The answer is absolutely not! Getting pegged, or enjoying any kind of anal play, has zero to do with your sexuality. After all, the concept behind getting pegged is having someone without a penis be the one doing the penetrating. 

The simple act of having something enter your backdoor isn’t gay — anyone can do it! If that’s your hangup, it’s time to let it go and get it on the way you want to without the stigma. You’re free now. 

Plus, getting a prostate massage or milking feels good! There’s a reason they call it the “P-spot,” after all — it’s like the G-spot, only for prostate owners. Your prostate doesn’t have a sexuality, so if you’re brave enough to try something new, you’ll experience it the same as anyone else with a prostate (regardless of who you prefer sleeping with).

Know Your Booty

We know you’re ready to dive in, but you’ve gotta know a few things first to make pegging work for you. Honest question — how much do you know about your booty? Likely, you haven’t spent much time contemplating how your anal anatomy works. It just does, right? 

Like every other part of the body, the booty (or butthole or anus, depending on how you refer to it) is pretty amazing! It’s the final stop of the GI system, so almost everything you put in your mouth will eventually exit here — which is why prep and clean-up are so crucial beforehand (don’t worry, we’ll walk you through it).

While we’re discussing anatomy — many people use anus and rectum interchangeably, but they’re different things entirely! The rectum is the piece that connects the colon (or large intestine) to the anus, so they’re not the same. And don’t forget about the taint (perineum) — that lovely space between the balls and the anus.

However, the star of the show when it comes to getting pegged is the anus. In theory (and in porn), anal penetration looks easy — porn stars just lube up and start going to town. In reality, as much as it would sometimes be nice for everything to be like porn in real life, that’s just not how bodies work. 

The anus has two different layers of muscle — the internal and the external sphincter — and only the internal sphincter can be somewhat controlled by conscious thought (for reference, this is the part that you squeeze when you’re running to the bathroom). 

However, we’re not as lucky with the external sphincter. You could sit and focus on your external sphincter all day long, and it wouldn’t loosen up. Getting through this layer requires physical action, specifically pressure, because its primary job is to keep your poop from just falling out when you walk around. 

Kind of an important job, right? Luckily, there’s a hack, so start with a fingertip before moving on to full penetration. 

Pegging Toys

Pegging needs more advanced planning than other advanced-amateur kinks. Obviously, pegging is more involved than simple anal sex; one of you isn’t going to have the anatomy needed to bang your partner the way they want you to. 

It won’t work as well (or be as hot) for either of you unless both of you are comfortable, which is why we’ve got to talk about pegging toys. Like humans, bedroom gear comes in many shapes and sizes.

While you can definitely browse and even buy your pegging toys online, we highly recommend an in-person visit to a reputable adult toy store with a sex-positive customer service ethos before you embark on your pegging adventure. 

(As in, not a windowless establishment just off the interstate that makes you feel a not good type of dirty walking in). The right sex store won’t make you feel ashamed or embarrassed — they truly have seen it all and love helping people have the most mind-blowing sex of their lives!

But before you head out the door, keep the following in mind.

Don’t Cheap Out 

We get it; we’re all on at least some kind of a budget these days. We’re not saying you have to blow through your entire savings, but good sex toys aren’t cheap, and cheap sex toys aren’t good. This is always true, but especially so when it comes to pegging because it involves a strap-on with a harness. 

The reality is that cheap harnesses scratch, pinch, and slide around. While this may sound like it would be annoying, it can also be painful if you get a piece of skin (especially in a sensitive area like the labia) caught between the harness and the “o-ring.”

Trust us, nothing kills the vibe quicker than having that happen, and it might even buy you a memorable trip to the emergency room (although you’ll also get a funny story to tell your friends later, too). 

But the strap-on is only half the experience; you don’t want to cheap out of dropping cash on a good dildo, either. Cheap dildos feel like … well, like cheap dildos. Realism is a vital component of the pegging fantasy for many people. You’ll have to spend a little money — but it’s well worth it. Plus, well-made, high-quality dildos last longer, so you will get a lot more bang for your buck (pun fully intended).

Don’t worry — we have a few tips! For beginners, start small. The recipient may have fantasies about taking nine thick inches – who wouldn’t – but if pegging has only been a fantasy until this point, that might be a little unrealistic. 

Stick with dildos intended for anal beginners — no bigger than five inches — or even a large butt plug or anal beads (your friendly sex shop worker will steer you in the right direction). And we know we’re going to sound like a broken record, but don’t attempt to put anything in your (or your partner’s) booty without using lube. 

Types of Harnesses 

Most strap-on rigs wrap around the hips, simulating the position of a real penis – and some accommodate a dildo that also stimulates the pegger, bonus! However, some dedicated peggers claim to achieve better control with a thigh-mounted harness. 

They are also considerably less expensive, so if you’re a pegging n00b, don’t rule them out as an option. Most shops will let you try them on, over your clothes, of course, so you can see what feels more natural to you. 

Lube and Other Tools 

We know you’ve already touched on it a few times, but it deserves its own dedicated section. You wouldn’t dream of attempting to peg or be pegged without gallons of Sex Oil, right? RIGHT? Hopefully, before you get drilled, we’ve drilled that much into you. 

We strongly believe that lube is for everyone, every time, but it’s an absolute non-negotiable for pegging. You can even take it a step further and get that bottom warmed up with Intimacy Melts for deep relaxation from the inside. 

Intimacy Melts are especially helpful if it’s your or your partner’s first time with penetrative sex. And remember, if you’re using a silicone toy, opt for a non-silicone lube. Silicone-based lubes can degrade your toys, which is no fun.

On to the Action!

As tempting as it may be to jump right in and start thrusting, that’s a great way to crush a pegging fantasy before you’ve even had a chance to enjoy it. Plus, ouch! All the usual Sex Rules about patience, communication, and paying attention to your partner’s body appear here in enormous, bold type. 

Getting pegging wrong can hurt, and not in a good way, even leading to serious tearing and injury – so take your time, speak up, and listen. We’ve said it before, and we’ll say it again — lube. Lube, lube, lube. Never peg without it. 

Start With Sex by Hand

Explore with fingers first (and lots of lube), and work up to a small handheld toy or plug (and even more lube) before strapping it on. An inexperienced peg-ee may have underestimated how much prep anal play can take for the recipient, so don’t skimp. If they say stop, stop.

Go Slow and Let the Bottom Take the Lead

The pegger doesn’t have the advantage of physical sensation with penetration here, so they’ll need to be extra-conscious of how the peg-ee is responding. Insertion can be especially tricky because “ohhh yes” can turn into “OH NO” fast with anal. Starting out, choose a position where the receiver can control the speed, depth, and angle of penetration.

How the Pegger Can Get Off Too

Remember how we mentioned that there are strap-on harnesses specifically designed to accommodate double-headed dildos? If the pegger loves penetration, there’s your answer. 

If clitoral stimulation is more their jam, slip a bullet vibe into the harness for an “ooooh” with every thrust. While many people enjoy pegging their partner as an act of selfless love, why not get something out of it too? Double the pleasure, double the fun, right? We’re all in.

Masturbate! 

If the “catcher” isn’t one of those lucky folks who can climax solely from anal penetration (which is only about a third of people, at most), they will probably want a little extra help while getting pegged to get off. 

Unless the person doing the penetrating is extremely coordinated and flexible (if you are — good for you!), this will have to involve the receiver masturbating while you’re going at it. But don’t let your peg-ee have all the fun! If you’re the one wearing the harness, you can (and should) masturbate too! 

Use your hands, a vibrator, or even invest in a strap-on with double-sided potential like we discussed. Pegging already smashes taboos, and “masturbation is strictly a solo activity” is a hangup we can’t wait to see fall by the wayside.

Communication 

People have pegging fantasies for many reasons. It is rarely as simple as getting a good angle for a prostate orgasm. The act of penetrating or being penetrated comes with a ton of cultural narratives, which are probably key to why y’all find the idea hot – so discuss! 

Find a quiet moment when you’re both relaxed and explore your stories. Quality communication — before, during, and after sex — is one of the best ways to expand your intimacy and deepen your relationship with your partner. 

Plus, being able to let your guard down and be vulnerable is actually super sexy and a huge turn-on for people. How else will you help them find the right spot that makes you scream without communication?

Knowing yourselves and each other is essential to explosive intimacy. At the intersection of dirty talk and “am I doing this right” lies pegging nirvana — sought by many and, we hope, soon to be achieved by you. 

Conclusion: Ready To Peg?

Take the time to review some of our favorite blogs on anal play and anal orgasms, make sure you’re familiar with the relevant anatomy, and head to the store with our strap-on buying tips in mind. 

You’ll have your own mind-blowing pegging sessions in no time — just don’t skimp on the lube!

Sources:

Internal anal sphincter: an anatomic study | PMC

Prostate‐induced orgasms: A concise review illustrated with a highly relevant case study - Levin - 2018 - Clinical Anatomy | Wiley Online Library

Why Women Engage in Anal Intercourse: Results from a Qualitative Study | PMC

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