How To Peg Your Man | All You Need To Know

Quick links: Pegging Definition | Reasons To Try | How To Prepare | Step-by-Step Guide

Shakespeare said it best – to peg or not to peg, as that is the question.

Well, not exactly the quote, but the idea was there.

Most people, but men especially, are wary of anal sex when it comes to receiving. An anus is a sacred place and one that should not be touched after all.

Or is it?

Pegging has become a popular topic of conversation in the modern world, moving away from the scary taboo it once presented itself to be.

Think about it this way – even Deadpool got pegged in front of millions of people worldwide, and he seemed to have fun with it.

This article will dive into the topic of pegging and all the wonders it can do for a man who just wants to get himself off in more ways than one. Specifically, it’s all about targeting that p-spot and watching the magic happen once things get going.

Let’s strap in (or on)!

Sex Educator 101: What Does Pegging Mean?

The guide to pegging begins with its definition. The term Pegging was popularized after it was voted as the most appropriate word for the thrusting sexual practice in Savage magazine in 2001.

Ever since it’s been the go-to word for penetrative anal sex with a strap-on.

While this is typically something female partners experience with their male partners, it can also be done woman to woman. Either way, there’s a sex toy, like a strap-on dildo, and ass play involved.

Anal Play: Why Do It at All?

Now, you may be asking ‘Why would guys subject themselves to anal play?

Thing is, if there’s any sex that would benefit from pegging, it’s men. On a biological level, penis-wielding individuals have a prostate gland that is reachable only by anal penetration.

Best Prostate Massagers | Read More

Anatomically speaking, it’s located between the rectum and the penis, and this is right where the male G spot is located.

Finding and, more importantly, stimulating that spot can unleash a prostate orgasm that is much more powerful than a regular orgasm.

“Men possess a prostate gland, an erogenous zone which is often pleasurably stimulated during receptive anal sex.”

by J. Michael Bailey; National Academies Press, 2003
from from The Man Who Would Be Queen: The Science of Gender-Bending and Transsexualism

Why Explore Pegging?

There are several reasons why a couple would choose to explore pegging. Of course, it’s down to preferences, but it can be a nice adventure, especially for women.

Since most orgasms are clitorally stimulated then grinding with a strap-on can actually be pretty pleasurable for the no-dong-Johns too.

Aside from the obvious – being able to experience a prostate orgasm, that is – pegging is also a good way to switch things up with your partner.

Since most female partners prefer to be the receivers then reversing the roles can bring a lot of new and exciting sexy times into a relationship.

The BDSM Factor

The idea of power play through BDSM scenarios comes to mind. Say you buy a blindfold plus some restraints. Or a pair of cuffs and hot wax.

“BDSM or sadomasochism practitioners enjoy one or more form of “kink” as part of their erotic and intimate life, such as bondage, pain play or impact play, dominance and /or submission, fetishes, role playing, or “master/slave” or “mistress/slave” relationships.”

by Kathy Labriola; Greenery Press, 2011
from Love In Abundance: a counselor’s advice on open relationshis

Add pegging on top of that and it sounds like you have some exploration and power playing to do.

You can dive even deeper by exploring some dominant vs. submissive roleplaying. All you need is an underwear-style harness, a bottle of lube, and a whole lot of doggy style.

Anal Sex and Taking Control: The Loaded Question

No guide to pegging is complete without the ultimate question of poo. More specifically, how to prevent an accident from happening and potentially ruining all pegging experiences henceforth.

A potential shit show will be on the horizon if you’ve been eating. That’s just how the body works. With a strap on inside, it’s pretty difficult to stop bowel movements from happening.

You digest food, you wait for it to process, you need to go number two – that’s the reflex.

It’s usually recommended to avoid eating any potentially problematic foods before trying the backdoor. These include dairy, spicy foods, runny foods, and any foods that may stir up or irritate your stomach.

Hygiene Matters

Obviously, make sure to stay clean at all times. This means a thorough scrubbing of every body part before sex. It includes washing your toys too – especially important for the dildo you’re gonna be using during the pegging.

You may use a sex toy or two, but you don’t want to attract any harmful bacteria to the rectum. It’s sweet loving, not a sour one.

One More Thing…

It’s important to know that the feeling – like you’re about to go – doesn’t mean that you actually have to go. There’s a discernable difference between the two, though this depends on the person’s experience and knowledge of the forbidden fruit.

See, the muscle that contracts and releases during number two is the same one that works the dildo. Chances are it will feel extremely weird, because the sensation is exactly the same.

Otherwise, if you’re still unsure, just skip the rump pumping for another time to avoid any sticky and uncomfortable situations.

A Guide to Pegging: It begins with the Strap on Dildo

The golden rule to anything sex-related (especially if there’s a partner involved) is that you have to start small when it comes to sexual experimentation of any kind.

by Robert Thomas
from Sextopedia

Obviously, no one is a fan of visiting the ER after their first time getting pegged. The act of pegging requires a lot of communication and a ton of lube.

It also calls for plenty of knowledge on how to correctly use a strap-on, for example.

Having the desire to please your partner isn’t the be-all and end-all of prostate stimulation.

Exactly What is ‘The Talk?’

We at Sextopedia (also MensHealth) suggest that the first step is knowing how to bring up the topic to your partner.

Whether you wish to be the giving or receiving partner, it’s important to talk about it ahead of time. Before showing up at someone’s door with a burning desire in your eyes and a strap-on locked and loaded.

The art and quality of pegging will depend on how close you are to your partner and how often you experiment in the bedroom.

Also, how often you use a toy and how open you are to kinks and taboos. This conversation can either be open-ended, or you may have to tinker with it before you pop the pegging question.

There’s no real way to go about this other than trusting your partner with something you’ve wanted to explore for some time. Either way, it’s a matter of open communication.

Strap in for a Strap

To minimize any unwanted reactions or awkwardness, it’s best to shop for the dildo in question together. Since this is a relatively sensitive matter for many men, having them pick what goes up their ass matters.

“Dildos can be used in conjunction with strap-on harnesses to allow hands-free use.”

by Jodi O’Brien; SAGE Publications, 2009 
from Encyclopedia of Gender and Society

It is step number one in getting them to relax about the whole ‘I got anally penetrated by my partner‘ ordeal.

What they choose to buy is up to them – but it should be something small at first. When it comes to materials, it’s best to go for the nonporous kind. Ideally, it would be a silicone dildo from a sex toy company known for creating good-quality products.

If you want to add a little spice from the outset, then try a vibrating toy (for example, a vibrating dildo). But, there are always alternative toys like vibrators, butt plugs, or even beads.

Read More | Vibrators Vs. Dildos

Or, maybe induce some other orgasms during the act of prostate stimulation.

Lube is Your Best Friend

If you think you have enough lube, you don’t have enough lube.

No anus is self-lubricating, which goes both ways. This means there are no natural bodily fluids that will help in sliding that dildo in with ease.

This is where lube comes in to save the day. But, remember that a lot of it needs to be applied for painless penetration.

Depending on the toy you have, you need to pair it with the right kind of lube. It’s always best to go for water-based lube since it’s the most toy-friendly of the bunch.

However, there are always hybrids in case you want stickier or more prolonged lubrication.

Still, be careful not to pair silicone toys with silicone lubes, as they can permanently damage the toy.

Stick to Foreplay

A giant strap-on dildo torpedoing its way straight into someone without any preparation doesn’t exactly feel sexy. Unless fear is part of your roleplaying, in which case – go to town.

For most people, the act of pegging itself is a big deal and will feel awkward at first. And the cure for any big full-body orgasm experience lies in the foreplay!

Many women prefer a lot of foreplay before any penetration because, aside from feeling good, it also relaxes the genital area.

The same goes for the butt. Clenching hard before a pair of lips, fingers, or a dildo draws near will not make for the most exciting of prostate orgasms.

This is where some arousing but relaxing foreplay can really help – and open up a whole new world of anal exploration.

Add some nipple stimulation, bring on the vibrations, get the dick going, throw in some dirty talk – anything that floats your boat goes.

Fingers First

Before a dildo can come anywhere near the butt, have something else penetrate it first. More than likely, this will be a finger – but it can be a tongue too.

The idea is to help relax the area of the body that has naturally been designed to push things out and close up when something tries to go the other way.

To do this, you can simply use some fingers. This is how you can go slow and establish all the important boundaries. Meaning, what to lick, where not to touch, and where to definitely apply the pressure.

All control must be in the hands of the peg-ee, not the peg-er.

The Plug Route

Otherwise, a small butt plug always remains an option. The thing is, butt plugs are created for the purpose of stretching out the butthole.

So, having one on hand is not bad, even if you’ve already dabbled in some anal fun and games before. It causes some minor expansion, so it becomes easier to add things in and lubricate the area.

Positions Matter

If you’ve ever received a penis, dildo, or any other penetration tool, you will know the drills. Especially, the problems that come with finding the right position before it feels good.

Pegging works the same way in that no man will feel comfortable getting pummeled into the floor from the get-go.

Most people think anal + pegging = doggy, but it’s actually one of the worst positions if you want to feel any sort of pleasure.

In fact, anal penetration done the wrong way can cause some serious pain. It can also lead to tearing, bleeding, and possibly, never pegging again.

The most comfortable position is when the receiver can control the pressure, speed, and pounding level. 

It’s then understandably best to do it from a spooning position. Here, there’s enough intimacy to make it a little more romantic, but it makes for easy access as well.

This goes without saying, but this is not the time for a rabbit pounding – take it slow.

Ignore the Pressure for Orgasming

Any first-timer will know the pressure that comes from being expected to climax during fourth base. Sure, porn makes it look easy.

But, it’s completely unrealistic to expect an immediate full-on, rolling of the eyes in the back of the head, and body-shaking climax.

Both parties should be honest with their expectations for each other, especially when it comes to orgasms. The only goal should be pleasuring each other.

The one receiving the dildo needs to have a good time throughout the entire endeavor, not just anticipate the end goal. The end goal of doing the nasty is having fun, after all.

The same goes for when you’re introducing a strap-on into your bedroom.

Be Prepared for an Accident

While nobody exactly likes accidents, they still tend to happen. Especially for those who are just dipping their toes (or a dildo) into some unknown territory.

Any physical mess can be sorted out easily. But, it’s also down to having the mental ability to check, communicate, and deal with any unwanted aftermath after the fact.

This is where having a solid relationship can help. Remember, it’s also about moving past awkward incidents through mature communication.

As I and any other sex educator would have you know, if you’re not ready to deal with an accident, you’re not ready for intercourse in general.


The goal of pegging should always be to please both people involved. And, decision-making should always sway on the side of the receiver.

Still, the act is about shared satisfaction, a sexy fantasy come true, and a new and exciting way of parking in the rear.

Once things are comfortable for the both of you, strap on for the ride and follow some mighty fine advice from Abbi straight out of that one Broad City episode. She said it best,

‘Plow him (or her) like a queen!’


  • Robert Thomas

    Robert Thomas is a sexologist, researcher, and writer who loves to explore and investigate everything that is related to bedroom action. He strives to improve couples' sex life by challenging the advice given in research papers, books, magazines, and on the internet in general. Robert loves to write about sex, BDSM, as well as tips & tricks on how couples can introduce new sex toys to their relationship. He has been proudly featured in Healthline, Bustle, Cosmopolitan, Self, AskMen, MelMagazine, Kinkly, Jack&Jill Adult, and in many other publications. Learn more. LinkedIn

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