Communication

When exploring any new type of sex with your partner, it is important to have a conversation about it first. Read our guide on “How to Talk to Your Partner about Anal Sex.” Taking that one step further, you may want to agree on a “safe word” that either partner can use during play if it becomes too intense, painful, or for numerous other reasons.

Butthole Cleaning

Before any type of anal play, clean your butt! This means have a bowel movement at least an hour beforehand, don’t eat for a few hours before you play, and wash your bum with mild soap and water.

You can also use an enema or anal douche beforehand as well, but it is not necessary unless you are worried about poop or if you want to experience enema play.

Use Lube

One of the three keys to anal sex, along with communication and relaxation, is lube. Yes, lubricating the anus is that important. This is because the anus is not self-lubricating and doesn’t stretch as easily as the vagina.

Any type of anal lube will do, and the more, the better.

Foreplay

A good warm-up is also essential when it comes to anal play. This includes stimulating all the various erogenous zones that turn you and your partner on, as well as anal massage.

The Rosebud Massage is a type of anal massage developed by sex educator Joseph Kramer, and it involves massaging and stimulating the “starfish” and surrounding buttocks before anal penetration. Then, using lots of lube, you massage the derriere, the cheeks, the crack, and the anal opening with “rocking, kneading, playful spanking, cupping, gliding, and stretching.” This helps relax the mind and body in preparation for anal sex.

Get Prepared

For the pegger, you may want to try on your strap-on first to get used to it for a while before you attempt any type of penetration. It’s also a good idea to finger your partner’s anus first to get a “feel” for how the anal canal bends and where the prostate is located. Again, this is a great way to introduce your partner to how anal stimulation feels before advancing to pegging.

Start Small

Most pegging strap-ons feature a smaller dildo - for several reasons. For one, the prostate is only 2” inside the anus, so you don’t need a huge strap-on to reach it. Two, a large dildo will likely be very uncomfortable, especially for beginners, so a smaller dildo is often the best way to start.

Penetration

During strap-on sex, the person being penetrated should decide on the degree to which they are pegged. That is, they decide the depth, speed, rhythm, and force of penetration. This is where communication comes in again, which is a must during anal play.

Anal Missionary

The partner being penetrated lies on their back with their legs raised and knees bent towards their chest. They may also rest their legs on their partner’s shoulders. Having a cushion or sex pillow like the Liberator Wedge under the butt also helps to raise it higher for pegging.

Doggie Style

This is a classic anal sex position in which the person being penetrated gets on their hands and knees, and their partner penetrates them from behind. This is one of the best positions for beginners and is easy for both partners.

Reverse Cowboy

In this position, the strap-on wearer sits on the edge of the bed or a chair, and the partner being penetrated sits on their lap. This position allows the partner on top to slowly ease down on the dildo and control the angle, speed, and depth of penetration.

For Beginners

Scandal’s Crotchless Pegging Panty Set is a sexy pair of red and black lace boy shorts with a small silicone dildo perfect for pegging.

Gender-Neutral

The Temptasia Harness Brief is a gender-neutral pair of boxer briefs that can be used with any strap-on dildo with a flared base. Very comfortable and great for people who want to try out packing as well.

The Gender Fluid Enthrall Strap-On Dildo is 5.5" and will fit most strap-on harnesses. Features a non-phallic design, curved tip for P-spot and G-spot pleasure, and is made of 100% body-safe silicone.

For Vulva-Owners

The Strap U Pro Rider features remote-controlled vibrations that target the wearer’s G-spot for added stimulation while pegging their partner. In addition, the person being pegged enjoys extra vibration as well. This toy is more suited to experts, as a strapless strap-on is harder to wear because you need to have strong Kegel muscles to keep it inside. However, it can be used with a harness for training purposes.

For Beginner to Expert

The original Bend Over Beginner Kit by Tantus has two interchangeable dildos (small and medium), so you can grow into the larger one or mix and match depending on your partner or a specific type of pleasure.

For Cowboy Position

I love this Ultra Thigh Strap-On made of soft, comfy, stretchy neoprene that is adjustable to fit around the thigh and can be used for Cowboy anal strap-on play.