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Anal Strap-On Pegging Guide

Dr. Lisa Lawless

Dr. Lisa Lawless, CEO of Holistic Wisdom
Clinical Psychotherapist: Relationship & Sexual Health Expert

Strap-On, dildos, harness, pegging


This anal strap-on guide (Pegging) will cover the basics of how to wear a strap-on dildo with harness to provide strap-on anal sex with a position guide and essential tips. Pegging is a sexual term for anal sex using a strap-on. It is performed by a cis or trans woman who performs anal sex on a man by penetrating him anally with a strap-on dildo. She may also simultaneously stimulate his genitalia.

The most important things to remember when it comes to pegging is to use a lot of lubricant and to start slowly with a small and shorter dildo and work up to thicker and longer ones to avoid causing tissue damage.

You want to ensure healthy anal penetration and avoid any damage to the anus and rectum so taking it slowly is important. To increase the pleasure, you may choose a curved dildo as it will help stimulate the prostate in a male, and if your partner is open to vibration, you can certainly opt to get one that vibrates.

Before you purchase any anal toy you will need to ensure that it is anal safe. Make sure to see our Anal Toy Guide to help you better understand what makes a sex toy qualify as anal safe. 

General Anal Strap-On Tips

To ensure all goes smoothly, make sure you have your harness on correctly and snugly and that you are in a comfortable position and angle for easy anal penetration. If your harness is not fitting well or loose, it can make penetration much more difficult, so making sure your dildo presses firmly against your pubic bone is ideal. Also, as some dildos are curved, if it moves around in the harness, it may not be pressing against the best spots (prostate for men) so make sure that the curved tip is always facing straight up at a 12 o'clock position.

When you lubricate, make sure to put some on the dildo and around the anal opening and reapply whenever you or your partner feels drag so as not to irritate. Some sex toy materials will need more lubricant than others, so always communicate about comfort levels and keep lubricated.

Go slowly and put the tip into the rectum while having your partner slowly breathe and relaxing as you gradually insert the dildo about halfway in and the slide back (not pulling it all the way out) and then slowly go further with each slow thrust. Once your partner is comfortable, you can begin to move more vigorously but always begin slowly and check with your partner to make sure they are comfortable and not in any pain.

Anal Strap-On Positions

An excellent way to start with penetration maybe with your receiving partner on their back so that you have face to face contact and can easily communicate not just with words but so that you both can read each other's body language. Having your partner with their legs up and open also allows them to relax and fully open up the rectum. From the position with your partner on their back, you can also stimulate their genitals with your hands or have your partner masturbate at the same time.

There are many sex toys that your partner can use for genital stimulation, and for women, it tends to be clitoral vibrators, and for men, it tends to be male vibrators or male masturbation sleeves. With harnesses that have vibrators in them or that offer double penetration, you can also receive genital stimulation.

Another good sex position will be the doggie position where your partner puts pillows under their pelvis or lifts their rear-end to allow access from behind. You can have them rest their head downward or have them on all fours.

Bending over can be done from a standing position, and using a chair or wall for support can help provide resistance for increased thrusting sensations.

Another position can be done with the strap-on harness wearer on their back in either a lying or sitting position allowing your partner to climb on top of you while facing you and then sliding the dildo inside them to control the penetration.

If you want to do a reverse cowboy position, which is where your partner straddles you while you sit or lay down and faces the opposite direction of you, then make sure to turn the dildo if it is curved to be upside down to allow the curve to stimulate your partner correctly.

Additional Anal Strap-On Resources

We have several articles that you should explore in addition to this one in choosing the right anal stimulation for you:

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