Sex + Dating

The Ultimate Guide To Pegging Your Boyfriend

guide to pegging and strap ons
Thrillist/Oren Aks

In case you somehow haven't heard, pegging is all the rage right now. People are going totally apeshit over it. And for good reason! It's wonderfully liberating to have this kind of sexual experimentation making its way into our boudoirs, don't you think?

But while pegging has become a media darling of sorts (thank you, Broad City!), the act isn't as prevalent amongst everyday people as you may believe. Shocking, I know -- but turns out strap-ons aren't flying off sex-shop shelves so everyone on Earth can give the next-level sex act a good old college try.

Conquering your man's backside may be chill for you; but he might be sketched out about you "compromising his manhood" or whatever. You have to tread lightly -- which is why we've created a helpful and practical pegging handbook. Lucky you!

From bringing up the *novel idea* in casual conversation, to anal sex positions for the uninitiated, here is the ultimate guide to pegging your boyfriend.

What is pegging? A very, very brief history.

Simply put (and at the risk of terrifying you), pegging is penetrating someone anally with a strap-on. The name came from a poll hosted by columnist Dan Savage to describe this then-unnamed sexual practice. Pegging was the winning term, and the rest is... history?

Make sure everyone knows what's up

Relationships are about open communication. If you want to peg your boyfriend or your boyfriend wants you to peg him (marry him), you should be able to discuss the pros and cons in a safe way. Pegging isn't (always) about being the overlord of your boyfriend's ass! It's about trying new and exciting things together in the bedroom.

If you want to try pegging, you're going to need to make sure everyone involved is on the same page. No anal play without the green light. Don't come in hot and buy a strap-on without discussing it beforehand.

Don't pressure him

An important rule of pegging etiquette is keeping it neutral. Broach the topic with care. Pegging is an experience that has to come from a place of trust.

I won't lie to you, few guys are going to be open to pegging. It's just not that normalized in our society yet.

I won't lie to you, few guys are going to be open to pegging (my current BF included). It's just not that normalized in our society yet. If your boyfriend is not down and cannot be reasoned with no matter how many facts you present, you have to let it go. Him doing it out of obligation won't be fun for either of you -- and pressuring someone into sex acts is always, obviously bad form.

Make this experience about the two of you

Pegging is about you AND your man. Use "we" instead of "I" when you bring it up: "We should try this cool new sexual thing. It could be fun for us."

You don't want to terrify your boyfriend by acting like a Dom Queen. There is a time and place for that, but the time when you're trying to bang his bunghole is not one of them. OK?

Get professional help

I'm not talking about a relationship or couples therapist; I'm talking about a sex-toy expert. You want to start with a dildo that is simple and manageable; but finding the right toy can be daunting when you have no idea what you're doing.

Going into a sex shop doesn't have to be intimidating. Don't go to some creepy, seedy shithole with mannequins wearing leather thongs in plexiglass windows. Go to a real, upscale boutique that prides itself on providing an enjoyable customer experience.

It may seem straightforward, but strap-on harnesses come in a variety of different styles and can be a bit tricky to put on. You'll want to pick what's right for you, which can only truly be done by physically going into the store and trying one on.

harness strap on babeland
The Jaguar is an empowering harness for women | Thrillist/Cole Saladino

My favorite spot in New York City is Babeland, but you can find your own just about anywhere.

You'll typically find employees at these shops to be kind, helpful, and very well-trained. They'll be able to help you find exactly what you're looking for. And they won't make you feel weird about it.

Get your BF's input, but don't make him come shopping

Your boyfriend does not need to be included in this purchase. You should ask him what he wants and what he feels comfortable with. That's it.

I get that going to a sex shop alone might feel scary. If you really need someone, grab a girlfriend. DO NOT BRING YOUR MAN -- unless you get off on watching him hyperventilate the minute the salesperson whips out a bunch of 8in dildos.

Buy the right stuff

I like the SpareParts nylon strap-on because it has a pocket for a vibrator (clit stimulation, yay!) and has a very neutral look. It's like wearing a piece of clothing.

harness spareparts babeland
Thrillist/Cole Saladino

My favorite of ALL is the Jaguar. It looks a little intimidating, but it is literally the luxury car of strap-ons. The leather is super buttery and it is incredibly simple to use. The Jaguar is like your favorite little black dress: a classic that never goes out of style.

strap on juguar
A smaller dildo is ideal for beginners | Thrillist/Cole Saladino

Obviously what you buy depends on your price range. That said, a strap-on should be an investment. Trust me. You're talking to a girl who bought her first strap-on off Amazon. It was NOT good.

You'll also need to buy O-rings, the round pieces of plastic that go in the opening of the strap-on to hold your dildo in place. Since you're just beginning, you'll want to buy small O-rings. The last thing you want is to have your strap-on come loose in progress. Ask your trusty salesperson at the shop for advice on which to purchase.

o-rings babeland pegging
O rings in various sizes | Thrillist/Cole Saladino

As for your dildo, pick something in a fun color like purple or black. I like the Tantus for beginners. A flesh-colored dildo is going to make him cry and he'll tighten up like a Chinese night flower.

dildos in various sizes babeland
Tantus on right | Thrillist/Cole Saladino

Put a condom on your strap-on

It's important to use condoms on your sex toys, especially if you're using them with multiple partners. But even if you're a one-man kind of lady, there is nothing sexy about scrubbing down a dildo. Most especially a dildo that's been up someone’s butt.

Make the cleanup as painless as possible by putting a condom on your strap-on (and all your other anal toys, for that matter). Condoms also help with easy insertion (read: lubrication!). Yay, condoms. Speaking of which...

Use all the lube in all the land

Lube. It's what dreams are made of. And when it comes to anal, the more lube the better. If you think you have enough lube, just add some more for good measure. It's messy, but it's better than a painful butt-sex experience.

babeland lube house brand
Babeland lube | Thrillist/Cole Saladino

Stick with water-based lubes. Silicon, while more delightfully slippery, can damage the integrity of some silicon-based toys. Be sure to read the directions on your dildo to see what kinds of lube will work best. I recommend Babeland's in-house lube. It's thicker than other water-based lubes, which helps the dildo stay lubricated.

Choose the right positions (so you don't break anything)

For anal beginners, you have to be in the RIGHT positions to make it work. DO NOT put your boyfriend into doggy-style. This may seem like the obvious choice, but it's actually a rookie mistake.

Doggy-style is actually a difficult position to pull off anally, regardless of what porn has taught you. You can wind up penetrating in a shallow way that could cause serious pain (or tearing... which also falls under "serious pain").

Instead, try laying behind your boyfriend and entering him from the spoon position. Depending on your height difference, you can put a pillow or two under his hips to elevate for easy access. And remember: TAKE IT SLOW. Now is not the time for rabbit pounding, no matter your desire for power play. (Alternative position: him on top, controlling how fast and deep he's being pegged.)

The prostate is your friend, and his!

The prostate is the key to anal pleasure for our dear menfolk. It is what makes getting it in the butt so damn wonderful. So, be sure you're stimulating it. Here is a comprehensive guide on prostate stimulation that I wrote just for you! The prostate is your best friend, my dear pegging neophyte. And a dildo with a curved head is optimal for prostate contact.

As my gay best friend/brother always puts it: "There is literally no orgasm like a prostate orgasm." This could actually be a big selling point in your initial pegging discussion (see above).

Make sure the dildo is always facing away from your boyfriend's spine, toward the bellybutton, to ensure prostate stimulation. This direction will depend on the position, but it should be pretty straightforward based on general comfort.

There will be poop

Listen, friend. I don't want to hear you complaining about poop when you're looking to peg.

dildo pegging babeland
Curved head for optimal prostate stimulation | Thrillist/Cole Saladino

I was at a bachelorette party explaining how a butt plug works and why it rocks when one of the girls asked me about the likeliness of being pooped on, "Expecting not to deal with fecal matter when you're entering someone's asshole is like expecting to avoid vaginal fluids when entering a vagina." It just isn't reasonable to go for anal and think you won't encounter some shit.

Expecting not to deal with fecal matter when you're entering someone's asshole is like expecting to avoid vaginal fluids when entering someone's vagina.

There will be poop. It may smell kind of gross, too. Be aware of these things and come to peace with them BEFORE you stick an object up there. It's not a big deal. Everyone poops. Anal rocks. The end.

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Gigi is Thrillist's Sex and Dating staff writer. Her boyfriend is not down to peg and it’s really upsetting. Follow her lovable crazy on Twitter, Facebook, and Instagram @GigiEngle.