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 a person who has a penis with a strap-on dildo?

Even though many people have always pegged and been pegged, and even more have fantasized about it, the word itself is of fairly recent origin. It emerged after sex columnist Dan Savage took a reader poll in 2001, asking “what the heck should we call this thing so many of us do and more of us want?”

“Pegging” reigned supreme, though we’re old enough to remember voting for “bobbing”. And now everyone knows about it, which is great! Pegging is an amazing way to explore multiple fantasies at once, with the bonus of spectacular orgasmic potential for the peg-ee. 

But many folks, potential peggers and peg-ees alike, are still nervous about taking the pegging plunge. This article is for you.


Why Peg?

Oh, many reasons. For the recipient, pegging is a great way to get one’s prostate pounded, and enjoy the psychedelic orgasms that result. It’s also an exploration of a physically submissive role that people with prostates usually don’t get to play in, and people without prostates take for granted.

As for potential peggers, most of us have always wondered what it’s like to have a penis – and 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 the mind 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 really get into the weeds here talking about patriarchal power constructs and phallus as metaphor and so forth, but we’d rather get you two into bed – and fortunately, that’s our job.

So review our favorite blogs on anal play and anal orgasms, get familiar with the relevant anatomy, and let’s head to the store!


Pegging Toys

Pegging needs more advance planning than other advanced-amateur kinks. It won’t work as well for either of you unless both of you are comfortable, and both humans and bedroom gear come in a range of shapes and sizes.

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.) And don’t be embarrassed – they truly have seen it all!


Before you go, keep the following in mind.


Don’t cheap out. 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. Cheap harnesses scratch, pinch and slide around, and cheap dildos feel like… well, like cheap dildos. Realism is a key component of the pegging fantasy, and for that you’ll have to spend a little money – but it’s worth it.


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, they might be a little unrealistic about their capacity. Stick with dildos intended for anal beginners, or even a large plug (your friendly sex shop worker will steer you in the right direction).


Types of harnesses. Most strap-on rigs wrap around the hips, simulating the position of a real penis – and some are designed to 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 cheaper – so if you’re a pegging n00b, don’t rule out that option.


Lube and other tools. Yeah, so, you wouldn’t dream of attempting to peg or be pegged without gallons of Sex Oil, right? RIGHT? We think lube is for everyone, every time, but it’s an absolute must for pegging. And get that bottom warmed up with Intimacy Melts, for deep relaxation from the inside.


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. 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 – so take your time, speak up, and listen.

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.

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 when it comes to anal. Starting out, choose a position where the bottom has control over the speed 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. 

Masturbate! If the bottom isn’t one of those lucky folks who can climax solely from anal penetration, they will probably want to masturbate while being pegged – unless the top is extremely coordinated. And the top can (and should) masturbate too, with hands or a vibrator. 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. 


Knowing yourselves and each other is essential to explosive intimacy, and 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.

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