How To Peg: From Choosing Gear To Positions & Everything In Between

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Pegging or strap-on play is for people of all genders and sexual orientations.

via GIPHY

What is Pegging?

Pegging specifically refers to when a woman uses a strap-on to anally penetrate a male partner. The term was coined in 2001, though written descriptions of the act date back to at least 1795.

The man is often, but not always, heterosexual. Contrary to some people’s misconceptions there isn’t anything inherently gay (or bisexual) about butt stuff. Anal play can be very pleasurable due to the concentration of nerve endings in the anus.

Some people with prostates can achieve orgasm through prostate stimulation alone. Prostate orgasms have been described as more intense full-body orgasms.  Read Prostate Massager: 5 Reasons Why Your Partner Needs One.

The taboo nature of anal sex can make it exciting on its own. Perhaps you want to take on a more submissive role being dominated by a woman. Maybe gender reversal is your thing, though that is not required for pegging.

If you’ve already discovered that you like anal play, pegging might be the next obvious step to exploring your newfound love of prostate stimulation.

If you are new to anal sex you aren’t going to want to dive in headfirst with pegging. You don’t want to go from never having had anything in your butt to sticking a dildo up there.

It is better to experiment with other anal play first or it could end up scaring you off of anal all together. Check out How to Prepare for Anal Sex to get you started. 

Choosing a dildo

The receiver should have first say in choosing the dildo. Start with something smooth and slender if you are new to anal penetration.

You may want to choose a curved dildo for prostate stimulation. Anal toys need to always have a flared base to avoid the toy from getting “lost” inside the rectum. The flared base is also necessary to hold it in place in the harness. 

The man may have a preference between phallic vs. something less realistic. For some gender-bending fun go for something realistic and you can even engage in a simulated blow job. If that’s not your thing there are plenty of non-phallic dildos available. 

Some men love vibration against their prostate. You can choose a vibrating dildo or a dildo with a hole where you can insert a bullet vibe.

A vibrating strapless strap-on provides internal stimulation and vibrations for both partners. 

Silicone dildos are a must because they are non-porous and can be sanitized after each use. A quality silicone dildo can even be boiled. Do not buy anything jelly or made of TPR/TPE as they are porous and may also contain harmful chemicals.  Read The Best Way To Clean Your Sex Toys

Choosing a harness

Don’t skimp on your harness purchase. You may be tempted to buy a cheap novelty-type harness. A low-quality harness isn’t going to hold the dildo securely in place and give you the ability to thrust properly. 

A traditional harness has straps that you can tighten and customize to the size of the wearer’s body. They come in different sizes so be sure to take measurements to get the appropriate size.

You want a tight fit to hold the dildo in place. They have o-rings to hold the dildo. Make sure it comes with the appropriate size o-ring for the size of your dildo. 

Another option is a pair of specially made underwear that has a hole for the dildo. You can get a pair of boxers, briefs, or even lacy ones. Some of them even come with a pocket for a bullet vibe to stimulate the wearer.

The downside to this option is that a heavier dildo is going to weigh them down and you won’t have as much control of it. 

Check out the strap-on harness collection The Sex Shed.

Pegging technique

You may want to warm up with a smaller toy or fingers first.

Whatever you do, use lots of lube and continue to reapply the lubricant. Do not use silicone lube with silicone toys. Instead, use a quality water-based anal lube. Give How to Prepare your Partner for Pegging a read. 

Go slow at first. The speed and intensity of the thrusting should be based on the personal preferences of the receiver. Communication is paramount.

Some people prefer a light circular massage of the prostate, so she should try getting her hips moving. The best technique is to listen to what they want. 

Don’t be surprised if the man goes flaccid, especially when first penetrated.  That is quite common and not an indicator that they aren’t enjoying it. Either of you can then manually stimulate the penis during pegging if you’d like. 

Pegging positions

There are a multitude of positions for pegging. Some positions may make the man feel more vulnerable which may or may not be preferable.

Positions, where you can make eye contact can be very intimate. Other positions such as the “Bendy” can play into the submission aspect of pegging. 

The man on top positions allow the man to be more in control and can be a good way to start out. This can either be in a sitting position or with the woman lying down.

These positions allow the man to control the pace, intensity, and depth of penetration.

Doggie

• Go slowly (real slow) and use plenty of lubricant.

Surfing

• Have your partner lie down on a belly. You squat over them.
• Rest your arms on their back & start thrusting, 🙂

Strap-on Train



• Your partner can masturbate since their hands are free.

Showoff

• Position yourself on the edge of the bed.
• Use lube.
• Let your partner control the movements and speed.

Daddy

• Easy beginner postion.

Shower Peggy

• Try pegging your partner in the shower.
• Hold on to something so you don’t fall in the middle of action.

Ride Me

• Don’t forget to swtich to this one at some point. Very intimate and romantic position.

Reverse Cowboy

• Simple yet sexy as hell.

Bendy

• Bend them over and show who’s in charge of the sitiation.
• Use a pillow in order to be able to push their head down and hold onto their hands – behind their back.
• Hike your leg on the table for better control.

El Classico

• Receiver is in a submissive position.
• Great for spanking and especially if you like it rougher.

Pegging tips

The key is communication before, during, and after. Discuss your desires and boundaries. Let each other know what you are wanting out of the experience. Communicate what is and is not working for you. Don’t be afraid to experiment to find out what you like. Practice aftercare and discuss how it made each of you feel both physically and emotionally.

Many men describe prostate orgasms as being more intense, lasting longer, and being a full-body experience. Women may find the pegging experience to be empowering. It can be fun to have your own dick to swing around. 

Whether you just want to try something new or you are a simply big fan of anal, pegging can bring a couple closer together. It can be all about dominance and submission or just plain kinky. Either way, it is a fun way to try new things that may or may not become part of your regular sexual repertoire. 

Guest author

This work has been created by joint efforts of Storm Elliott, Luka from Spices of Lust & Tamara Kurtanidze(illustrator).

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