Pegging 101: The Beginner’s Guide

What is pegging?

This is likely review, but let’s make sure we’re all on the same page first. Pegging is a sexual act that refers to someone (usually a woman) penetrating their partner (usually a man) with a dildo. Most often, the dildo is placed in a strap-on harness, which allows for hands-free thrusting. Fun!

Although it may be considered taboo or kinky, pegging is enjoyed by a large number of people. And while pegging most often refers to a woman penetrating a man, people of all genders and orientations enjoy both giving and receiving strap-on sex.

In this post, we’re focusing on the woman-penetrating-man scenario. For one, it’s what we have direct experience with, and for two, it’s what most people think of when they think of pegging.

Pegging misconceptions

Before getting into pegging tips, let’s cover some common misconceptions. Even if you’re feeling gung-ho, it’s helpful do a little check for any baggage you’ll want to get rid of before diving in.

1. Being on the receiving end makes you gay

This is a harmful stereotype that’s just wrong.

It’s pretty basic. Your sexual orientation deals with the genders you find sexually attractive, not the acts you enjoy. People of all sexual orientations can enjoy receiving anal stimulation. Still, heterosexual men can sometimes feel awkward or ashamed for enjoying anal because of the stigma surrounding it.

The fact is that there are countless nerve endings in that area, and it’s not weird or abnormal for them to provide powerful, pleasurable sensations. What’s more, cis males of all orientations have a prostate. Pegging (and anal in general) can stimulate the prostate and create some very enjoyable sensations. So enjoyable that the prostate is sometimes called the “p-spot” and is roughly comparable to a woman’s “g-spot.”

For many people, anal just feels good. If someone says it feels good, respect it: don’t read into a hidden agenda.

(Of course, while everyone should feel empowered to enjoy anal as much as they wish, without shame or fear of social repercussions, it’s important to also recognize that not everyone—no matter gender or sexual orientation—will enjoy anal. And that’s OK.)

Still, this misconception is one of the reasons why being on the same page as your partner is especially important when exploring the idea of pegging, especially if you haven’t done anything like this before. Be kind and gracious to each other.

2. Women don’t get anything out of pegging

My girlfriend laughed when she saw this. But it’s true, some people may think that pegging is only done for the male’s satisfaction.

She’s told me that she feels sexy when she’s pegging me, and she enjoys how it gives her a chance to be in control of the rhythm and experience penetration in a completely different way. Pegging can be an immensely rewarding experience from the top’s perspective.

Some women also find the physical sensations of pegging pleasurable, and there are actually a lot of ways to make it more so. Depending on where the dildo is situated, thrusting can put pressure on the clitoris. You can take it a step further and buy a dildo with a vibrator in the base, or even get a harness with a pouch for one. Some couples will also experiment with strap-free dildos or double-ended dildos so both partners are penetrated simultaneously. There are a lot of creative ways to make pegging enjoyable for both parties.

Finally, even if pegging doesn’t do anything for a woman physically or mentally, she may still get something out of it. Just knowing that what you’re doing is making your partner feel good is enough to make it worth it and fun in so many different scenarios.

3. Poop is a guarantee

As with all anal sex, additional preparation is usually required. When done right, the chances of your pegging session involving poop are quite small.

Still, there’s always a chance of an accident. It literally comes with the territory. But while it’s good to consider the possibility, prepare for it, and talk with your partner about it, this possibility shouldn’t be something that keeps you from trying pegging. Nor is it a guarantee. As long as your bottom has adequately prepared for the session, you can have a high degree of confidence that you can proceed without worrying about this.

4. If he’s not hard, he’s not enjoying it

Erections are not a reliable indicator of arousal during anal intercourse. This is another reason why communication is so important! Especially as you start out, you’ll want to check in with each other often. Men: try hard to vocalize your feelings. If it feels good, tell your lady. If it feels not-so-good, tell your lady. Women: don’t psyche yourselves out if he’s not hard—and believe him if he tells you he’s digging it.

Every man responds differently to anal stimulation. Some will stay super hard the whole time. Others will go soft immediately. Some will go back and forth like a crazy pendulum.

Communicate.

Pegging 101

OK, now that that’s out of the way, let’s get to the guide. I’ve tried to incorporate tips from my own experiences to help make sure you start your pegging escapades on the right foot.

First, talk with your partner

If you haven’t ever brought up pegging before, it’s not a good move to just pull out a giant dildo and strap-on harness in the middle of sex one night, and be all, “SURPRISE!”

My suggestion is to have a conversation or two with your partner while not in the middle of sex. Some couples maintain collaborative lists with things they’d like to try. In that scenario, it can be as simple as adding it to the list, then talking about what you like about it with your partner.

When you bring it up, you can try to tie it to something that you already do together that you enjoy. That can be an easy way to broach the subject. Something like, “Remember that time I put my finger in your ass you while giving you a blow job? It seemed like you really, really liked it—and I know I did. I’ve been getting super turned on thinking about exploring things in that area a little further.” (Then explain your fantasy / why pegging interests you.)

It’s best to be open and straightforward about what you like. In my opinion, vulnerability and honesty are requirements on the road to fulfillment.

Last tip on this: the conversation is going to be more difficult the less you communicate with your partner now. Try to get in the habit of talking to each other regularly about your fantasies, likes, dislikes, etc. It will make opening up about things like pegging so much easier!

Practicing

The bottom (the guy being penetrated) should be comfortable playing with his own butt before someone else plays with it.

Here are some reasons why:

1. This familiarity will help communication immensely. Especially at first, a ton of communication is important. If all the sensations are unfamiliar, he’ll have a much harder time telling his partner what’s happening.
2. It will give him a basic understanding of what angles, positions, etc. feel best him, and help him learn how to relax. The more practice he has before trying it with his partner, the better he’ll be able to work with his body to make sure it goes fantastic.
3. If he’s never played with his butt, a little training is likely required before jumping to even a small dildo. He’ll want to make sure he can handle the pegging toy comfortably. That often means training and working up to it.

I don’t recommend people jump into pegging until they’ve done a bit of lighter anal exploration together, either. So even if you have a lot of practice playing alone, it’s a good idea to introduce anal play in a lighter way first—perhaps with some fingering during intercourse.

Get the right pegging equipment

Dildo

Get a silicone dildo—none of this jelly crap. Not only do cheap, jelly dildos pose health risks, they can also ruin the mood in the moment by causing burning sensations and irritation. Bite the price bullet (and really, nice toys aren’t that expensive) and get toys that are safe.

Size: that’ll vary. Honestly, the first time my girlfriend pegged me was with a rather large dildo—but I was very experienced and we’d even done a bit of fisting before then. For your first time pegging, you’ll want to choose a dildo that you’re familiar with and comfortable taking on your own—one you’ve mastered. Whether that’s one inch wide or three is your prerogative. (Something like the 1.1″ wide Silk Medium from Tantus would make for a good first dildo. And it’s only $40.)

Harness

I have a good amount of leatherwork experience and tools, so I made my harness out of leather. That’s not going to be the easiest option for most people, but fortunately harnesses are easy to find at most sex stores. Initially, you may just go with an affordable option (I have no experience with their harnesses, but Tantus’ Vibrating Velvet Harness would surely hold up for long enough to determine whether or not you’re into this, and it’s only $30.)

You can always upgrade to something higher quality later, after you know more about what you want in your harness.

If price is really an issue, you could also try making a harness out of rope.

Lube & other preparations

I’d suggest a water-based lube (Sliquid’s Sassy gets good reviews!). You can also experiment with coconut oil. I personally find the staying power of an oil-based lube super helpful with anal, but YMMV.

It’s also absolutely worth it to make sure you have a towel. We’ve found that it’s very helpful to put one down underneath us during pegging sessions. It allows you to be generous with lube without worrying about making a mess, and it’ll also catch any drips/ejaculation.

Plan a time

I recommend planning your pegging session in advance so that everyone can prepare as they need to. For the bottom, that will likely involve a bit of clean-up/preparation so that no accidents interrupt the first scene. For some, this may be as simple as making sure they’ve had a recent movement. Others prefer having a couple of days to monitor their diet, etc., but most people will probably want to use the restroom and give themselves an enema before they play. I also like to do a bit of solo-play before a pegging session, and also shower: it helps me relax.

Planning ahead isn’t just about giving yourselves time to prepare physically. Doing so also allows you to block off a big chunk of time for the pegging session—that way you know you’ll have plenty of time to relax, get into it, and take care of each other afterward. It also gives you time to get into the right headspace before playing and gives you a window of time for flirting/teasing to build anticipation.

Go for it—it’s time to try pegging!

A few reminders and tips:

• Use a lot of lube.
• Warm up first, using fingers, smaller dildos, butt plugs, etc. before moving to pegging.
• Be OK laughing and if things don’t go quite right. For many people, pegging requires relearning how to have sex. Everyone will have a learning curve.
• Try different positions to find the one that’s best for you. Most people gravitate toward doggy style, but there’s a lot to be said for laying side-by-side: this can sometimes help for easier entry.
• It can sometimes help to have the top reach around and give a bit of a hand job during pegging. This extra bit of stimulation can help ensure that it’s an enjoyable experience.
• Be in a comfortable, familiar environment, and make sure it’s warm.
• With time, she will get better at thrusting—it turns out that while it feels so natural for men who have always had erections, it’s not always so natural for all women. Getting that hip roll isn’t always so simple!
• Men: even if you’re used to playing with yourself, but you’ve never had someone else enter your butt, well, this a whole different ball game. Don’t worry if you struggle to relax more than normal.
• Have a backup plan / don’t worry if it doesn’t go perfectly. If you only are able to try it for a little bit, but then have to stop for whatever reason, that’s OK! Don’t be afraid to transition to other sexy acts that are more familiar, and come back to pegging a different day. It can take practice!

Above all else, COMMUNICATE. Tell each other what’s working and what’s not.

I’d plan to try it a few times before making a judgment call about pegging. There’s just so much going on with the idea. If you’re open to the idea, it’s worth giving it a fair shot.

Aftercare

Even if goes absolutely swimmingly (and I bet it will!), pegging can have a draining effect and put people in funny moods afterward, especially if it’s still new. Whether it’s cuddling, drinking a beer, watching a movie, or just going to sleep, it’s important to set aside some time for aftercare.

You’ll also want to talk about your experience together. What went well? What did you feel? What parts did you like best and what parts could you do better next time? This kind of recap conversation can help make your next pegging experience even better and bring you closer to your partner.

What are your best pegging tips and stories?

Share in the comments below—I’d love to hear them. And you never know: maybe you’ll help someone else!