Everything You Need to Know About Pegging

Everything You Need to Know About Pegging

As journalist Brandy Jensen wrote in her totally lit Twitter bio, “Behind every successful man is a woman pegging him.” We at HUSTLER Hollywood admire the spirit of that sentiment, and we are pleased to see that pegging - at least, people talking and making jokes that feature it - is finally becoming more mainstream! It’s fantastic that so many guys and gals are finally discovering this magical sex act, and that it’s getting popular enough that MEL Magazine proclaimed last year that “We’ve Reached Peak Pegging Culture.”


If you don’t know what the word “pegging” means, you’re not alone. The use of the word in the way that we’re using it only started as recently as 2001 when it won a contest on Dan Savage’s popular sex column Savage Love. So we’re not only going to show you what it means, but also give you a guide with all the dirty details on how to do it or get it done to you! Here’s everything you need to know about pegging.

Pegging FAQ

What is Pegging? What is Getting Pegged?

We’re not gonna mince words with our pegging definition. The act of pegging is, put simply, a woman fucking a man in the ass.


The ladies typically do this by strapping on a harness with a dildo sticking out and getting it acquainted with their partner’s anus. Really, it’s just good old-fashioned anal lovin’, but the other way around from how you usually picture it, and with a little help from some toys.

So, Wait, is This Ga-

Let me cut you off right there, straight men who inevitably ask this. Here are a few things you should know:

  1. Sure, this word describes a man getting pounded in the ass, and yes, that isn’t a position that lots of straight men usually find themselves in. But it specifically describes getting pounded by a woman. If this is sex between a biological male and a biological woman, then it is, by definition, hopelessly heterosexual.
  2. It’s not inherently gay for a guy to enjoy any kind of backdoor action. With the right tools (and toys), any woman can pound an ass as well as the boys can! You can also appreciate a good butt-pounding and still be a man. (On that note, you can also be gay and still “be a man.” Miss me with that stereotyping!)
  3. With all that said: if you’re the type who likes to think deeply about sex, there's been quite a bit of queer theory analysis about pegging that’s pretty interesting!

Talking With Your Partner About Pegging

Like with any sex act, you’re going to want to make sure that your partner is into the idea before anything. Here are some tips on how to talk to your partner about it:

Make the Subject Come Up “Naturally”

Depending on the kind of person your lover is, you may not want to just bring up the idea of pegging out of nowhere, But you also shouldn’t count on your partner to just mention it, even in casual conversation - straight couples can go their whole lives without talking about switching spot during sex.


That’s why you’ve gotta take the initiative and figure out how to bring it up in a way that doesn’t feel forced. Here’s a couple of lines you can use to get a conversation about this started:

  • Remember that scene in Deadpool when Ryan Reynolds gets pounded in the butt by his girlfriend?
  • Wanna hear something interesting? I just read somewhere that apparently, girls using a dildo on their boyfriends is a thing.

They may not be the most subtle ways to do this, but they’re something!

Address Their Concerns

Women pegging men can be a ton of fun for everyone involved, but not everyone thinks so at first. Straight women might not see how being on the giving end will get them off, and straight men might be a bit nervous about being on the other end of penetration. Throw in some outdated ideas of gender roles during sex and the whole thing can just be uncomfortable.


You can try to convince them not by being totally dismissive - that’s just plain rude - but by hearing them out and responding:

  • This one’s specifically for the ladies: you probably already know how penetration can hurt a little and how it can feel really good. If your boyfriend’s worried about getting hurt, assure him that you can be gentle and start slowly.
  • If you only just started going all the way, you might want to give your partner a little more time to get comfortable with you before suggesting this.
  • At the very least, you can try to tell your partner that they don’t know how much fun it can be unless they give it a shot.

Obviously, if they definitively refuse to consent, you’ve gotta drop it. But an open conversation with open minds is worth a try!

what is pegging

Getting the Equipment You Need

Pegging is all about that strap-on. Luckily, we also have a handy-dandy guide for finding the right strap-on! Here’s some of the advice from there that’s more relevant to this:

Harnesses

Girls, there are so many kinds of harnesses out there. Some have actual straps that you tie, clip, or buckle on. Some can be put on like panties. Some even attach in ways that get you in on the fun, such as the Pipedream Double Delight Strap On. This wide range of choices means you’ve gotta find the one that gives you the best sense of comfort and control.


Once you get yourself a harness, you should break it in on your own before you break it out with your partner. Wear it while sitting down and watching TV. Have it on while walking around your home. Touch yourself while reaching under it. Do this until that strap-on feels like a part of you, and you’ll feel like you have better control in the bedroom.

Dildos and Anal Toys

Like with anything involving dildos, you should make sure to get one that wasn’t made with phthalates, and like with anything involving strap-ons, you should make sure your weapon of choice fits in the harness’s hole. But for pegging in particular, you’re going to want to start thin if your boy-toy isn’t used to fake toys. As much as you might want to tame your man with a monster dong, you have to wait until he’s ready to take that. On the bright side, this kind of training is fun is the kind that both of you can enjoy together!


If you’re interested in other possibilities besides the standard strap-on, there are ways to experiment! Why not give your man a workout and peg him with the Hustler Fetish Thigh Harness? Why not bring him to his knees (and hands) and show him the other end of doggie style with the Hustler Fetish Doggie Style Support? If you’re up for it, and he’s up for it, you can even lose the straps and get more hands-on with your pocket rocket. Pegging is pegging, and as long as you’re both having fun with p-spot probing, you’re doing it right.

Don’t Forget the Lube!

Of course. If you’re doing anything involving ass play, definitely use lots and lots of lube. Our favorite is the Wicked Anal Jelle. This baby’s thicker than your average lube, and that makes anal penetration smoother and easier. It’s also water-based and compatible with all sex toys.

how to peg a man

Tips for Maximum Pegging Pleasure

If this will be your first time pegging someone or your first time getting pegged, you’ll definitely want some advice on how to do it right and without that much pain. If you’re already experienced, some professional advice from HUSTLER Hollywood might teach you something new. Here are our hot tips for maximum pegging pleasure.

Start With Some Fingering

Maybe the man in the relationship hasn’t had the pleasure of getting something put in his hiney before. The anus, fragile and sensitive and tight as it is, needs a little training before you can start inserting jumbo dildos inside. Otherwise, pegging will be ridiculously painful, and not in an erotic way.


Maybe the simplest way to start anal training is if the woman in the relationship gives her man the finger. Whether you slap on a latex glove or go in bare-handed, learn how to play with his prostate using your pinky, the thinnest of your fingers. Get a feel for how to maneuver inside, what he likes and dislikes and really likes. You can try adding another finger if you’re both feeling adventurous, and then maybe you can graduate to a sex toy (but start with a thin one!).

Get Relaxed

First-timer fellas, this one’s for you. You might be desperately dreaming of getting a good reaming, but once that strap-on looms large and takes aim at that special and sensitive area, you just might feel a little intimidated.  Like we said earlier, we totally get that, and you shouldn’t be hard on yourself if you get a little nervous when the moment comes.


Of course, you can’t have much fun if you stay nervous, and that’s why you have to get yourself feeling calm. Ladies, you can help assuage your man with some romance beforehand - a little kissing, a little caressing, a little foreplay. If turning off the lights and setting up scented candles would help him lose the tension, then, by all means, go for it!


Remember, lads: you know that you want it (that’s why you and your lover talked about this!), and you know that it’ll feel good. And if you and your partner make some fumbles along the way, just laugh about it and keep trying!

Be Slow and Gentle at First!

We cannot emphasize this enough to women, or anyone about to perform anal sex: please please please don’t start pounding immediately! Men getting pegged for the first time are super sensitive. Instead, get your boyfriend used to having the dildo inside him. Insert it slowly, bit by bit, until he shows that it’s not hurting. Once you’ve got a lot or even all of it inside, give him a moment to take in the feeling.


Once he’s ready, get ready and start rocking back and forth a little. Both of you should go slow, at least at first. As he gets more used to it, he will likely start picking up that pace gradually, and you can start to get a feel for what he likes. Read his signs, have some fun, and go as slowly or as quickly as he wants. You can totally touch yourself if you’re stimulated, and you can reach around and touch him. And that is how to peg a man.


These are all the tips we can think of for a perfect pegging experience. We hope our advice helps you and your fuck buddy get some intense, rippling orgasms in a way that neither of you might have ever considered before. If you’re looking for the right tools to make this dream a reality, check out HUSTLER Hollywood’s massive online collection of dildos, strap-ons, and anal sex toys!