Pegging 101: A Top & Bottom Beginner’s Guide on How to Peg

Are you a straight, cis woman dreaming about becoming a powerful penetrator? Are you a straight, cis man fantasizing about a sexy woman with a strap-on fucking you? If so, this article is for you!*

That’s right, we’re diving into pegging!

The term pegging came about in 2001 thanks to the legendary Dan Savage, but this practice has no doubt been going on for much longer than that. In this article, we’re going to cover why this is controversial, why this is fun, and how you can be prepared to give it a try yourself.

*Though the dynamics are different, and it is no longer technically considered pegging when it’s outside of cis heterosexual relationships, the principles discussed here will also work for trans top men in gay relationships!

What’s so taboo about pegging?

Overwhelmingly, we are taught that straight sex is all about a penis inserted into a vagina.

This is laughably specific and excludes a lot of pleasure and experience from the definition. However, it’s a very persistent perspective. Many people consider anal sex for men to be exclusively in the domain of the queer world, but it isn’t. The gays just happen to have a lot of experience with it, on the (w)hole.

We also have internalized to varying degrees the idea that women are sexually receptive. So, the idea that a woman would wear a phallus and thrust into a straight man’s butt is super subversive to these ideas. Of course, you can also use a hand-held toy and it would still be considered pegging, but you might get a different sense of the power dynamic.

Taboo is subjective, and breaking taboos can be super hot and sexy ( remember the site you’re on? ). Maybe it’s the power swap that does it for you, or the off-limits male butt, BUT(T) there’s so much more to pegging than pushing social and psychological boundaries.

Straight-up biology: Prostates and nerves

One element to pegging that gives a biological basis for why this is so sexy, is the prostate. Cis men have a prostate gland that when stimulated feels super good and can even unlock big health benefits! It is best and most easily stimulated anally. The sweet spot is about a finger’s length up their anal canal and feels a bit like a walnut — just like your g-spot!

The prostate is unique to people born with a penis and testes, though there is a similar gland for vagina-havers called the Skene’s gland which is believed to be a major culprit for g-spot pleasure and has similar functions, but that’s a topic for another day! Suffice it to say typical straight, cis men who haven’t had to surgically remove their prostate will have one. Stimulating it can help reduce inflammation and may even help prevent some illnesses.

However, even if you don’t go all the way to stimulating prostates, the anus is super sensitive and has a similar amount of nerve endings as your lips. There’s actually quite a bit of biology that should allow for pegging to feel amazing!

Pro tip : If you’re going to be strapping on a toy, you can also get huge pleasure from it rubbing on your clit, or even from internal stimulation depending on your toy! It’s not just about your dude’s butt.

Everybody poops & how to avoid a “shitty situation”

Many of us believe that butts are dirty. For some, that’s part of the appeal. However, with some good hygiene, there’s no reason for concern. The anal canal is a temporary holding space, so as long as you’ve had a good BM beforehand, you should be fine. It’s also a good idea, especially if you’re nervous, to shower first, giving some extra care and attention to your butt.

Douching (rinsing inside your anal canal with water) is an option some people go with, but it certainly isn’t mandatory. If you haven’t yet gotten on the bidet train, I highly recommend grabbing yourself a simple bidet attachment and using that to clean away any lingering, unwanted bits.

Regardless of what you do, you might find that the fluids involved get a little tanned and there’s a chance that a small amount of poop might be on the end of the toy when you’re done, but I promise it’s not scary and if you just slap a condom over your toy before you start, clean-up is quick and easy! Just make sure to only use condoms with silicone, glass, stainless steel, or other body-safe toys. The oils in other toys break them down.

If you’re using body-safe toys, you can also boil them to sanitize or use a 10% bleach solution followed by a thorough rinse.

How to talk to your partner about pegging

You must talk about pegging with your partner before you do it. If you can’t talk about it, you shouldn’t do it. Full stop.

But what do you need to say? Well, you need to talk about any reservations you or your partner have. Play a game of What If and get out all of the situations you’re worried about happening, but also situations you hope might happen. It’s also a good idea (and good foreplay!) to talk about your game plan (start with light external massage, then move to licking, etc…).

Talk about speed, depth, safe words, angles, past experiences…anything that might impact your exploration together. And once you’re doing it at the moment, make sure you’re checking in and ensuring nothing is painful or too overwhelming. Good and plentiful conversation is just as essential as lube; use a lot of it and use more as you go.

If you don’t even know how to breach the subject, maybe start small with conversations about light anal play ( ie: how do you feel about a finger during a good bj? ) and eventually move on to bigger things!

Best Lube for Pegging

Speaking of lube, ANUSES ARE NOT SELF-LUBRICATING.

While you may be able to get away with penetrative vaginal sex sans lube, you most certainly can’t with anal penetration. Butts need lube like phones need charging — frequently and fully. There really isn’t such a thing as too much lube for pegging, so go hog wild on it and make that ass a slip’n’slide!

Silicone and oil-based lubes are going to be best to prevent hurting that delicate tushy! Just make sure you’re not using a silicone-based lube with a silicone toy, or an oil-based lube with condoms. You can also use water-based lube, but you’ll need to be even more proactive about reapplying.

What happens if you don’t use enough lube? Anal tearing — which increases your likelihood of contracting an STI/STD and will take some time to recover from. Plus it increases the likelihood of sex being painful. Don’t take the chance: lube up!

For a more in-depth look at which lube to get, refer to our handy guide

Finding the best toys for pegging together 

There are lots of toys you can use for your pegging. But be careful: butts like to slurp things up, so if your toy doesn’t have a sufficiently flared base, you run the risk of it getting stuck. You really don’t want to have to go to the emergency room for this, so be careful! Not all dildos are made for anal play.

Ladies: this is your time to choose your very own penis! Oh, lucky day! With so many options of colors and styles, you can find one that feels uniquely suited to you.

But don’t just choose one that you like. Choose your toys together. After all, it’ll be going up his butt, and he’s bound to have opinions about it. Size, shape, texture, and design can all make a big difference. Take the time to consider clean up, too. You’re going to want to clean your toys, and some will be easier than others. 

If you’re new to butt play, start as small as possible. There are even anal training sets ( this one will even fit in a harness! ) you can get to gradually work your way into it. This is not a go big or go home kind of situation.

There’s a lot to consider with this step, I know.

Fortunately, we’ve already put together a handy guide to help you and your partner choose the right pegging toy & harness for you.

Warm up and go slow

With all the excitement around being the penetrator, especially if it’s your first time, it can be super tempting to just get to the thrusting right away. Please don’t do that. An anus is not a vagina and everybody has their own tolerance. Listen to any directives your partner gives you, but also keep in mind that the more relaxed he is, the better it will be for everyone.

There are actually 2 different sphincters that need time to relax before you can get deep in there. One can be relaxed intentionally through relaxation techniques like deep breathing, and the other is connected to the autonomic nervous system that can’t be relaxed simply by telling it to relax. However, if you can stimulate them both simultaneously and gently, it can have a down-regulating effect that prepares your body for more orgasmic pleasure than if your body is aroused simply through fight or flight.

This takes time.

Massage, licks, and shallow penetration are all great to do for quite some time before getting into thrusting if you get there at all. It might take multiple sessions to get to a comfortable place for thrusting and you might never get there, and that’s ok. You don’t have to love it just because you wanted to try it. You also can always change your mind, at any time, about whether it is or isn’t for you. Just make sure you communicate that to your partner!

The best positions for pegging

There are a lot of positions to choose from, and the best ones for you and your partner will depend on your bodies.

Generally speaking, doggy style can be a great option.

It allows you to see what you’re doing as well as allowing your partner to back into you, rather than you thrusting into them.

In doggy style, for more pinpoint prostate stimulation, the top should raise themselves to lever the dildo down.

I know we talked about the subversive nature of women being the penetrative partner, but this is an especially sensitive and often times scary experience, and letting him take the lead, especially at first, can make all the difference.

Relative height might make doggy style a challenge. Another great option is to have him lie face down on the bed, maybe with a pillow propping up his hips. Again, this gives you a lot of control, so if the domination element is fun for you two, this could really trigger those exciting feelings. Keep in mind, he will have less power in this position, which means you have more responsibility to take care of his well-being.

For more intimate and complete sexual stimulation, face-to-face is a fantastic option that is often overlooked.

Regardless of who’s on top, his penis and testes will be more accessible and easier to play with while also letting you see his facial reactions. Being able to monitor his facial reactions will give you a better sense of how it’s feeling for him.

To stimulate the prostate further, the top should lower itself so the dildo levers up.

Standing on the floor while he is on the edge of the bed can make this position easier and give you more control over your thrusting. If he’s on top, he can also stay in control of the experience, which can be a great tool for you to learn what he likes.

Remember, if you want to focus on your partner’s prostate, avoid going full depth unless you’ve got a shorter toy!

Gotcha Pegged!

So there you have it! Pegging can be super fun on so many levels and there is so much to explore: toys, positions, and techniques. We hope this guide has at least given you a good, solid (and flared!) base to work from and stoked the flame of desire.

If you or your partner aren’t having fun, take it down a few notches or pause entirely and figure out why. Understanding when things go wrong can sometimes even bring you closer together than when things go right. It’s a journey you’re going on together that can foster a greater sense of empathy for one another. The pegger gains an appreciation for the challenges of being a penetrator, and the peggee gains an appreciation for how delicate and sensitive he should be when penetrating his partner.

It’s a win-win. If the two of you can enjoy and grow through this experience together, that’s a green flag if I ever saw one. Leave no man’s pegged behind!