FREE SHIPPING OVER $50       |       FREE RETURNS       |       SHIPS FROM THE USA       |       DISCREET SHIPPING & BILLING

What is Pegging Sex? The Beginners Guide to Anal Pegging a Man

by Danny Garrett June 15, 2020

What is Pegging Sex?  The Beginners Guide to Anal Pegging a Man

Pegging—One Of Our Last Taboos, But It’s Way More Popular Than You Might Think

 

We take a look at why so many couples are giving pegging (or strap-on play) a try. We’ll cover everything from the most popular positions through to the best lubes, straps, and toys to get you started. We’ll also look into the history of pegging and some of the recent high-profile appearances it’s made in popular culture.

 

What is the definition of pegging? 

 

Let’s start with the basics. Pegging describes a sexual scenario in which a woman uses a strap-on dildo to penetrate a man’s anus—usually (but not always) to stimulate his prostate gland. To be blunt, pegging a form of anal sex—but the traditional rules about who is penetrated and who does the penetrating are reversed.

 

This is enough to put some guys off without any further discussion. In some quarters, there is still a misguided association between enjoying butt stuff and being gay. But getting pleasure from a bit of bum fun if you’re a man doesn’t mean that you are attracted to other men. Remember—if you’re pegging, you’re still having sex with a woman, it’s just that she’s the one doing the penetrating. 

 .

pegging a man

 

So let’s set the record straight. Men and women have the same nerve endings in and around their butts, and stimulating them can be very enjoyable and sexually satisfying. It has nothing to do with sexuality—it’s all about erotic zones and experiencing a close, intimate physical connection. However, pegging does raise some interesting questions about who the dominant partner is and who submits to penetration. It lets couples experiment with traditional ideas of what it means to be male or female, and also provides an opportunity to mess around with power play and gender roles—if you’re game.

 

Why has pegging become mainstream? 

People have been pegging for a very long time, but the term is quite new—it was actually coined in 2001. The earliest reference we could find is in the Marquis De Sade's 1795 book Philosophy In The Bedroom.  In it, the lead female character penetrates her partner with strap-on called Steely Dan III. If you know your music, you’ll now know where the band got its name! The book is still in print today—and available in English—if you want to read it. More recently, you might have spotted a reference to pegging in Deadpool. If you haven’t, go back and have a look!

 

There’s also a lot more pegging in porn these days—that’s probably because there’s more porn out there generally. But the increase might also be mirroring modern attitudes and reflecting more fluid sexual and gender identities. Whatever the reason, however, don’t be tempted to use porn as an instructional guide to pegging. You need a few serious conversations beforehand, and excellent communication throughout—porn doesn't really show you that side of things. Instead, there are some good books on the subject, including Pegging for Beginners and Experts and The Adventurous Couple’s Guide To Strap-On Sex, which we'd recommend. If you really want a visual demonstration, check out Bend over Boyfriend. There's some educational content and advice alongside footage of real-life couples.

 

pegging 

 

Pegging and prostate play

For the most part, guys don't just wake up one day and decide that they want their partner to strap on a dildo and stick it up their ass. It takes a lot of trust for us guys to put all the physical, psychological, and emotional barriers to one side and be penetrated by our partner. Similarly, women usually need to progress to pegging their partners. They need to feel confident that they can turn their men on and generally be at ease while exploring anal stimulation as part of their sexual adventures.

 

For that reason, pegging is usually part of a much longer journey that might have started, at least for guys, in a desire to learn more about prostate stimulation. So it's likely to have begun with some solo play and a prostate massager or anal probe. Only men (and people born with a penis) have a prostate. It’s a small, walnut-sized gland that’s located just inside your ass between your bladder and the base of your dick[1]. The prostate produces a fluid that forms about a third of your cum, while the muscles surrounding it respond to sexual stimulation and help you physically shoot your load. The prostate is also an incredibly erotic zone—often called the male G-Spot or P-Spot.

 

prostate massage 

 

Lots of guys get into pegging because it provides intense, direct stimulation to the prostate. This stimulation will give you a harder and more powerful erection and can also open up the possibility of multiple orgasms in a single session. You may even achieve the much-discussed Super-O—a whole-body, mind-blowing orgasm with tons of cum that will shatter your senses and blow your mind.   

 

Pegging, anal stretching, and domination

Other guys arrive at pegging through their love of anal stretching with butt plugs and other toys such as anal beads. They enjoy the stretch and contraction of their sphincter muscle as their toy moves in and out. With the right strap-on attachment, pegging can satisfy these fantasies too. Other guys arrive at pegging through S&M and bondage play, and the thrill of being humiliated by a dominatrix. You can read more about prostate stimulation and other anal play in the knowledge center on our website.

 

Pegging should be fun for both of you

It’s important to feel confident in all forms of anal play—including pegging—so it can make sense to start solo. That way, you can work out what you like and what you don't. When guys do bring their partners into the mix, then it's often a gradual process too. It usually begins with mutual anal fingering, some rimming, and then the introduction of some toys. If your partner is new to pegging, she might also benefit from some time wearing the strap-on alone and getting used to how it feels before you get down to it together.

 

Of course, you’ll want your partner to get the most out of pegging too. Plenty of women (and people with vaginas) get off while pegging their partner as the penetrating motions and vibrations at the base end of the dildo stimulate their clit. There’s a growing range of silicone toys for women that fit snuggly over their pussies for additional stimulation while keeping them comfortable if things get a bit more energetic.

 

pegging harness

 

You also can find strap-on harnesses with a panty-like space at the front—they’re designed to hold a clit or bullet vibrator in place. As an alternative, couples can opt for double-ended dildos so that they can experience penetration pleasure at the same time. Be warned, they do take a bit of mastering—particularly from the lady's perspective, so this might be a more advanced option further down the line. If you really want to go all out, you could both try a triple-ended dildo to provide pussy and anal stimulation for her at the same time as she’s pegging you.   

 

Popular pegging positions for couples

Pegging, like most sexual acts, isn't usually done in isolation. Guys like to jerk off while they're being pegged, and, depending on the position you pick, you can enjoy turning each other on just like you would if you were fucking her.

 

There are almost limitless possibilities when it comes to pegging positions. If you can fuck her in that position, chances are she can fuck you right back the same way. That said, if you’re just starting out, there are a few positions that will help you get your technique sorted. We've suggested four easy-to-master positions that will ensure you both have an equally enjoyable experience. These include:

 

  1. The ‘Bend over Boyfriend’ (Doggy style for dudes)

Get onto all fours—either on the floor or on the bed. You’ll be quite exposed and might feel a little vulnerable, but that’s part of the fun. She will be fully in control of the speed and depth of the penetration. So make sure you both know how to communicate clearly to each other. It's crucial in this position as you won’t be able to see each other’s faces.

 

pegging a man doggy style

 

The Bend over Boyfriend provides easy access to your dick if either of you want to play with it while you're being pegged. For extra deep penetration, put your ass higher up in the air—you can even get up off your knees and she can go in in at a much sharper angle. If you’re both turned on by reversing traditional power roles, this one could be for you. She will literally own your ass.

 

  1. On your back, legs in the air (or over her shoulders)

This is an excellent beginner's position. You can see each other's faces, and it's much easier to judge each other's reactions. You can either bring your knees close to your chest, extend them a little into the air, or put them over her shoulders.  If flexibility allows, it's an excellent position for kissing and for playing with her tits. If you both fancy it, she’s also got a clear view to watch you jerk off, or to give you a hand when you’re ready to blast your load. With a bit of practice, you can even flip positions and end up riding her while she’s on her back and, if she fancies sitting on your big hard cock, it's an effortless switch! 

 

  1. On the chair like you just don’t care…

Ask her to sit on a low chair and then straddle her, slowly lowering yourself down on to the strap-on at a speed and pace that's comfortable for you. This gives you the most control out of all the positions we’ve mentioned—and allows you to progress in your own time. It's probably the most relaxed position for long and slow kissing and to get super-tactile with each other's bodies.

 

  1. Ride her, Cowboy!

Ask her to lay on her back and then straddle her while she’s wearing her strap-on. You can lower yourself down either facing her or facing away. Facing away may be easier for beginners as the strap-on is more likely to find its way straight to your prostate gland without too much effort. You may lose some of the intimacy as you can’t see each other’s faces—and she only has a view of your ass and the back of your head. You can always switch around a few times and face each other during your session—that way, you can figure out what works best for you both.

 

Pegging can help you with Erectile Dysfunction

Over time, pegging could be a good option for guys that suffer from erectile dysfunction (ED). Regular prostate massage—and release of prostatic fluid—is thought to help clear the prostatic duct and improve your chances of getting hard[2]. In fact, before modern medicines such as Viagra and Calais, prostate stimulation was the primary treatment for ED. Regular prostate massage can also help cure painful ejaculation, improve urine flow, and treat prostatitis (a swollen prostate gland). So, there you have it—prostate stimulation and pegging could improve your health too.  

 

ED and pegging a man

 

Bringing your prostate into play for some additional and mind-melting sexual stimulation can also get you harder than you thought possible. As we’ve highlighted, pegging also stimulates some super-sensitive nerves that play a part in triggering erections—so it should  

stack the cards even more in your favor and turbocharge your dick even if you don't have ED.  

 

It’s also worth keeping in mind that you don't have to be hard to have a prostate-induced orgasm. You can experience all the intensity—and then some—without worrying if you’ve got a boner. Trust us when we tell you that your whole body will be alive with sensation just before you have a prostate-induced orgasm. You'll be moaning and writhing with pleasure—and the last thing you’ll be thinking about the rigidity (or otherwise) of your dick.  

 

ED can also be caused by performance anxiety—the pressure to perform sexually. It’s particularly common for guys in the build-up to penetrative sex. Pegging can help here too as takes the emphasis away from your dick. You're no longer the only one in charge of the penetration during your encounters. If you still find you're struggling to get hard, then why not grab a strap-on kit of your own—plenty of guys do, and their partners love it. 

 

How to safely enjoy pegging

If you’re new to pegging, it’s sensible to start with a smaller strap-on and gradually build up. Remember that you don't have to pick a strap-on that looks like a dick (unless you want to). All strap-ons are designed to quickly locate your prostate and deliver maximum stimulation, so pick the style, size, shape, and feel that you're most comfortable with.  

 

One of the most significant barriers to enjoying anal sex of any kind—including pegging—is anxiety about being a little dirty down there. So, make sure you wash with soap and water beforehand. Use an anal douche or enema if you like, but make sure you get all the water out before you start. Some couples—even when they’re in long-term monogamous relationships—put a condom over the strap-on. It offers an added layer of protection, but it also makes cleaning up after a little easier.

 

Remember that lube is an absolute must. You should have plenty of it to hand and, we’d always suggest having a spare bottle on stand-by just in case. Many people believe silicone lube to be the best option for all forms of anal play. Silicone lube is thicker than water-based lube. This means it will last much longer and needs less reapplication. The extra thickness also offers some additional cushioning and protection.

 

If you’ve been experimenting with prostate massagers and other anal toys or have full-on anal sex with your partner, you've probably got some in your bedroom. But—a word of warning here—most strap-ons are made of silicone, and you can’t use silicone lube with silicone toys. If you do, they will start to lose their structural integrity, become porous, and stop being body-safe (another reason to use a condom on them, if you want to). For that reason, we recommend using a water-based lube for pegging. There are some really thick, long-lasting water-based lubes on the market today that are just as good for anal as silicone ones.  

 

Conclusion

We've talked a little bit about power play and the physical role reversals that are introduced by pegging. These new experiences can have a profound effect on how couples engage sexually. Most immediately, men have the opportunity to understand what it's like to be penetrated—and get an insight into the amount of trust, respect, honesty, and emotional commitment that's needed to let it happen. Let's be honest, it's probably not something a lot of us have thought about.

 

For many women, pegging can be about empowerment and taking back some sexual control—it offers much more dominance than just sitting on top of your dick. It also gives women the chance to see what it's to be the penetrator. They can experience the actual physicality, full-body coordination and full-on commitment that’s necessary to fuck someone properly. The theory goes that these new experiences and perspectives should make both partners much more rounded, communicative and attentive lovers. 

 

So, what are you waiting for? Are you up for giving pegging a try with your partner?

 

 

 

[1] Yes, There's a Male G-Spot— and Here Are 7 Things You Can Do to Find It

[2] What You Should Know About Massage Therapy and Erectile Dysfunction

Danny Garrett
Danny Garrett

Daniel Garrett is a certified sexual wellness expert through the Eldorado Sexual Health Board where he graduated with honors. Daniel's specialty is helping marriages as well as other relationships which struggle with having a healthy sexual presence. When a man is uncertain about his manhood it leaves him with a sense of self-doubt which typically will start to deteriorate any sexual relationship he may have with any partner. By helping men overcome their interpersonal self-doubt issues regarding their penis size and sexual function, Daniel is able to help heal relationships and help take these same relationships to the next level. Daniel's writing can be found on such websites such as The Enhanced Male, Marriage.com, as well as many others. Daniel has helped develop such relationship tools as silicone cock rings to help men achieve lasting results in bed.