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Beginner's Guide to Pegging


Curious about pegging? Are you a woman and excited to learn how it feels to be the penetrator? Are you a man who wonders if experiencing penetration is as pleasurable as it is enticing? Maybe you and your partner have wanted to try it but are not sure how exactly to go about it. Perhaps you have wanted to initiate your guy to the world of pegging but are not completely sure he would be on board.

The reasons for wanting to try it and the questions about doing it are as diverse as the human race, but based on the skyrocketing sales of strap on dildos, pegging seems to be gaining popularity.

Whatever the reason for wanting to start this particular sexual journey, welcome aboard.

What Exactly Is It?

Pegging is a sexual activity practiced between a man and a woman, where the woman performs anal intercourse on the man using a strap on dildo to penetrate him. That is the basic definition. However, as with other sexual practices, there are variations to pegging as well. These variations include:

  • The man masturbating (stimulating his genitals) while he is being penetrated
  • Using a double penetration dildo where one end is inserted into a woman’s vagina and the other end is inserted into a man’s anus
  • Using a dildo that vibrates or a vibrator in between the strap-on dildo and the woman’s body to provide stimulation to her clitoris
  • Triple-ended penetration where the dildo has three parts for penetration: one for the man’s anus, one for the woman’s vagina and one for her anus.

Pegging is nothing new. Like most sexual practices, it can be traced back to the Romans. The term pegging may not have always been associated with the act, but straight men have been getting anally penetrated for centuries. And they have been enjoying it.

As with most things, pop culture has helped bring pegging into the 21st century. It has been depicted in movies like Deadpool, in television shows like Broad City, and many people think Carol Queen is the woman to thank for putting pegging out in front when she released her video series "Bend Over Boyfriend" in 1998.

Fear Is Unfounded Here

For what it’s worth, if you are a man who has thought about participating in pegging but just have not been able to pull the trigger, know you are not alone. Unfortunately, fear is one of the biggest obstacles to most consensual sexual exploration. Pegging is no different. Fear can be holding a man back for many reasons: fear it will hurt, fear that having these desires are not normal, and fear desiring anal penetration means you are gay.

What was once considered taboo is now considered trendy. Today, more people are talking about it, and more couples are definitely trying it. Gone are the stereotypes and misguided beliefs that a straight man being penetrated anally is actually gay. Pegging is not a threat to masculinity. It is only a vehicle for pleasure. It is not related to gender identity, sexual orientation or sexual fluidity. And normal is just a setting on a washing machine, nothing more.

Changing the Way We Think About Sex

So, one thing that often has to happen before someone can pull the trigger on pegging is that they often have to change the way they think about sex. That goes for both parties. Sex is not just about a penis going into a vagina, and let’s face it, many male/female couples usually end up this way even if they use oral sex or other sexual exploration as a means to get there.

Women have to open their minds to being in the dominant role and being the partner who not only does the penetrating, but for the most part is the one in control of the speed, depth and rigorousness of the actual sex. Many women have spent their sexual lives in the opposite position, and with the exception of being on top during sex, have often been in the submissive position for the majority of their sexual experiences. It can take a while to get the hang of it, and if that is the case, there is nothing wrong with that. A lot of people experience awkward moments the first few times out with a lot of sexual activities, not just pegging. Getting the hang of it can take time and effort, but patience and persistence will be rewarded. It can literally feel like you are learning how to have sex all over again, because in a way, you are.

Women also need to be comfortable wearing a strap-on harness and dildo. This is something many women never thought they would consider, prior to pegging being put on the sexual table. A harness and dildo can take some getting used to. They may feel strange at first, and it may take trying several until there is one that seems to fit the bill. That is ok. For some women, pegging has been something they have wanted to do for a while, and the harness and dildo may feel like an old friend from the beginning. That is also ok.

If women are to look at sex in a new way when it comes to pegging, then it stands to reason that men must do the same. Willfully being anally penetrated may or may not be a new concept for a man. He may have just never gone “there” when it comes to thinking about sexual pleasure. Once considered, he may find he has to get into positions he never thought he would before. These positions may actually help with what may be a man’s greatest fear when it comes to pegging: pain. Positions that can make anal sex easier for a woman can also do the same for a man.

A rookie mistake is to go right for Doggie Style. Yes, it seems like the obvious choice but:

1. It is not as easy as porn makes it look.

2. It can lead to too shallow of penetration, which can cause tearing and pain.

Try having him lay face down with pillows under his hips to elevate his bottom. While he may have to get used to a new perspective, that doesn’t mean it’s a bad thing, and he may thank you for it later.

It is important to remember that no one is under any obligation to try pegging or any other sexual act. If it is not your thing, it is not your thing. That’s ok. Sex should always be judgment-free and a safe zone.

However, if it is something you think you might want to try, then there are some great benefits to it:

  • Pleasure - There are some serious nerves around the anus that can give intense pleasure. Pegging can take it to the next level.
  • Prostate stimulation - Pegging can really “hit the spot” when it comes to stimulating the prostate, which in turn leads to incredible orgasms.
  • Role reversal - Ever wonder what sex is like from the other person’s perspective? Are you a woman who has been curious to know what it is like to be the penetrative partner? Are you a man who really wants to know what it is like to have someone be in control and be on the receiving end? Pegging allows for all that.
  • It helps you learn how to please your partner. It can help you be more in sync with what your partner needs during penetration.
  • Pegging can improve sexual communication between partners. When roles are reversed, each partner has to learn to experience sex differently. That can make each person feel vulnerable, and increase talking about exactly what you want to happen and how. Think about what you are going to do if one person wants to stop.
  • The power switch can be a real turn on. Pegging takes a lot of trust that she won’t hurt you, and that is what women who are penetrated have to do when they are penetrated, especially by a new partner. There is a great deal of intimacy in that aspect alone.

Shopping for the Perfect Strap-On

So you have to talk about it and agree to it and all systems go. There's just one thing left to do, and that is to buy a strap-on. If it is your first time trying pegging, consider a smaller dildo and one that reaches and stimulates the prostate. Make sure the harness is snug but not so tight it is uncomfortable or cutting into the wearer’s skin, no matter which dildo you choose, there is certainly a plethora to choose from.

Vac-U-Lock Supreme Strap On with 6 Inch Realistic Black Dildo

The Vac-U-Lock Supreme is a great choice for beginners and experienced users. The dildo part is only 6.5 inches long so it is not too overwhelming for first-timers. The harness is very user-friendly and adjusts to fit the user. The Vac-U-Lock feature holds the dildo in place which is very important. No one wants to have it fall out at a crucial moment.

The Universal Lover Rider Harness is a must have. This harness is compatible with just about any dildo out there so it is a good investment for your pleasure.

Universal Lover Rider Harness

Once you have the Universal Lover Rider Harness, the world of dildos is at your feet. There is something for just about everyone’s taste. Here are just a few:

Tantus Pack and Play No. 2 Realistic Silicone Dildo

Tantus Pack and Play No. 2 Realistic Silicone Dildo

Tantus Feeldoe Stout Vibrating 7 Inch Double Dildo

Real Feel Deluxe No. 1 Realistic Vibrating 8.5 Inch Multi-Speed Dildo

Try one that vibrates or one that had double penetration. Start small and go up to large. There are no rules.

When it comes to lubricant, look for a lube that is designed for anal play, and remember to use it early and often.

Anal Ease is phthalate-free, and it's a lot of folks' go-to anal lube.

The Original Anal-Ese

Anal Lube has a thicker consistency and is longer lasting.

Anal Lube In Original Formula By California Exotics

A Word About Poop

Just a quick word. If you expect to engage in any type of anal play, including pegging, and never come in contact with poop, you are barking up the wrong ass. Yes, there are things you can do to lessen the chances; poop before sex, do an enema before sex. But it still may and probably will happen at some point. So, use gloves for finger penetration, wash dildos and all sex toys properly for that matter, wash the harness and never put a dildo that has been in someone’s ass in someone’s mouth or vagina. Just don’t do it. If some poop slips out, clean it up and carry on.

Some Things to Remember

Pegging can be very pleasurable for a variety of reasons. But it is no joke. It takes trust, willingness to be vulnerable, communication and sometimes a good safeword. Remember to use lube liberally. Remember to go at your partner’s speed. One of you may be ready to jump right in on full throttle, but the other one may need to take it slow and easy at first. Think about starting with some finger insertion and working up to the strap on. There is nothing wrong with speaking up for what you want and what you need.

Some people add pegging to their regular sexual routine, while some put it on the menu only sometimes. Whenever and how much someone does it, it should be consensual, safe and pleasurable.