Generally speaking, pegging is when a cis-women penetrates a cis-man with, typically, a strap-on and dildo. But it’s not like this is some long standing term in the sexual lexicon, it was actually invented as part of a Dan Savage naming contest in 2001 (shout-out to contest runners-up ‘bob’ and ‘punt’). Name origin aside, there’s absolutely no reason that anyone penetrating anyone anally with a dildo can’t refer to it as pegging or benefit from this intro guide. So let’s get started!
1) Open The Lines of Communication
Like with any new sexual act, you need to make sure that everyone is (enthusiastically) on board. If you’re already using fingers and butt plugs in your play, that’s a great moment to mention your interest in taking it further. Even if you and your partner regularly use a strap-on, using it anally is a completely different act and can never, ever be assumed. Explore your reasons for wanting to try it out. Are you interested in shaking up pre-prescribed sexual roles? Is it about exploring prostate stimulation? Get it all on the table.
2) Start (Really) Small
Before you get to strapping on a brand new cute dildo, you’re going to want to start with smaller toys and fingers. A rimmer toy is great for warming up and then a slightly larger butt plug will help you discover new sensation and boundaries. If you’re already well versed in the joys of wearing a plug you can move on to step 3.
3) Shop Together
If you were one of the many people introduced to pegging via that episode of Broad City, just know that that large, undulating green dildo is not exactly what we would recommend you start with. You’re going to want to find a slim, slick, preferably silicone dildo to start. If that goes well, you can move onto larger toys or harder materials if you’d like. We carry a toy made exactly for this purpose, The Pegging Probe is a slender 1” across and 5” long with a slight curve, perfect for reaching the prostate.
4) Strap In
You don’t necessarily need to use a strap-on to penetrate your partner, you can also do it manually. But if the body thrusting motion is part of the appeal for you (as it is for many) then you’ll want to get yourself a nice little harness. A low-cost strap-on with a jockstrap structure, is the perfect place to start. Then, if you find you want something more robust for enthusiastic play, you can look into a more structured option. Learn everything you ever wanted to know about strap-ons for beginners over here.
5) Warm Up
Don’t toss those plugs and rimmers aside, you’ll still want to start with them to help relax the area. The muscles surrounding the anus are incredibly strong and they take some sweet loving to relax. Don’t rush, use warm, lubricated hands and simply play around until they give you an enthusiastic thumbs up.
6) Lube, lube, lube, lube, lube
However much lube you think you should use, double it. Heck, triple it. When you’re playing with the booty you need to remember that it doesn’t self-lubricate. In an ideal world we’d be able to use a beautiful silicone toy with the most slippery silicone lube, but unfortunately silicone lube and silicone toys don’t go together (more on that here). So if you’re using a silicone toy, you’re going to need a (really) nice amount of water-based lube. Water-based lube absorbs and evaporates rather quickly, so keep it right next to you and reapply often. Really, really often. Have we made our point? LUBE!
7) Be Gentle
This can be a totally new feeling and one that can take some getting used to. So go very, very slow and shallow to start and work your way up based on feedback. Introduce a safe-word before you start, if you don’t already have one, and if you hear it, stop IMMEDIATELY. If done slow and steady with lots of lead up, this is often a very enjoyable experience, but everyone is different and you need to 100% listen to your partner.
8) Add Some Vibration
So, you’ve tried it, both really liked it and want to give it another go. This time, try adding a small vibrator for the wearer. Many harnesses have an interior pocket perfect for a small vibrator like the Mini or Fin. This way every time you thrust, you apply pressure between you and the toy. It’s a super win-win situation!
9) Don’t Forget After Care
Anal penetration can be an incredibly sensitive topic and experience. It can be physically extreme and also a bit of a mind trip for people getting over deep rooted societal hang ups, so make sure you take the time after for some love and care. Cuddle, make out, whatever helps to ground you both and then talk about your experiences.