A Beginners Guide to Pegging with a Strap On

Pegging is getting pretty popular at the moment (especially in porn for women), with depictions of it in mainstream TV and media helping to squash the stigma and let more people experience the beauty of butt-boning. But although it’s tempting to just grab a harness & go for it, it’s not always as easy and smooth sailing as what is shown on the television. So here are a few tips on how to have your best first experience.

Scroll on down for the what, why and how of pegging…

Traditionally pegging refers to a cis male receiving anal penetration from a cis female partner with a strap-on dildo, but more generally it can be used for anyone wearing a strap-on and anally penetrating someone else.

Fun fact: pegging was named in 2001 in a contest held by Dan Savage after he decided that heterosexual couples needed a term for the man receiving anal sex.

Anal penetration can feel good for any butt due to the ring of nerves around the anus, but for people with penises anal penetration can also massage the prostate. The P-spot is an erogenous zone located two inches inside the rectum and can bring a new type of pleasure and orgasms. If you’re interested in exploring more of the prostate you can check out my guide to prostate massage here. However, while some people want to be penetrated for the prostate stimulation alone, others get off on the role reversal of pegging. Submissive men may enjoy the erotic power exchange that occurs when their partners become the ones with dicks. In a patriarchal society where cis-het men still hold most of the power, submitting to a woman or another marginalised gender can feel pretty erotic.

Ok, first things first, you’re going to need something to penetrate with. There are some different things to take into consideration here…

If you have a vagina, do you want to peg with a harness on and feel like you have a penis? Do you both want the dildo to look life-like or would you prefer it to not resemble a penis? Do you, as the peg-er, want to have something penetrating you at the same time? If so, there are lots of double ended options that include an internal piece for you. It’s also important to think about the shape of it, whether it vibrates, how long it is, how thick it is… No matter the type of dildo that you buy, it’s always a good idea to start small and work your way up. Finally, you should look for something made from non-porous silicone, and clean it before and after every use with soap and warm water.

If you’re not using a double ended dildo, you will need to buy a harness. If you can, buy your first harness in a shop rather than online so that you can try it on first. You can look for one that sits on the lower body so that you feel pressure on your clit as you’re pegging, or you can look for others that fit like underwear. The most important thing is to find one that you feel sexy and comfortable in.

This is very important. Butts are not self-lubricating like vaginas are, which means you need lots of lubrication to make pegging work. So slather it on, and then slather some more. This is the main difference between a hot, pleasurable experience and a painful one. Water-based lube is the best choice as it’s compatible with silicone toys and condoms unlike silicone-based lube which lasts longer and is thicker, but it can degrade latex and silicone. With all of the items that you need, shopping together for them can be a great way to build up to the experience and feel connected with your partner.

Before anything sexy happens, communication always comes first. Other than making sure everyone knows how to physically prepare, you must discuss your desires, expectations and fears ahead of the experience. It’s an incredibly intimate act and one that you need to get full consent for. And of course, it’s not a one time conversation, you should check in with each other throughout and speak about how it was afterwards.

It’s a good idea to start with fingers or a butt plug before you whip out the harness and the dildo so that your partner can get used to the feeling of being penetrated. Having the peg-ee wear a small butt plug a few times during sex is a great way for them to get comfortable with the sensation, once they are comfortable with this you can progress to pegging.

Don’t forget about foreplay! The receiver needs to feel turned on and relaxed, because if they’re tense anal sex is bound to hurt. Some couples will start with lots of foreplay, others will start with vaginal intercourse if thats an option for them, then switch to butt stuff and then to pegging. There’s no one way to do it, just take your time. Before you use the strap on, start with something small like a finger to get them in the mood and work up for it. And please, please… DON’T FORGET THE LUBE!

When you’re both ready for the actual penetration, start slow and take the lead from the partner being penetrated. Put it in a little, then stop and wait for them to get used to the feeling, then continue. Take it slow and little by little until you get into it. Remember that pegging’s main disadvantage is that the person wearing the strap-on has no sensation to guide them so go slowly and gently.

If you’re both new to this it can be a good idea to let the receiver choose the position, and to have them in one that allows them to control the depth and speed. Having them on top of you in cowboy, is good for this. Otherwise lying on their back with their knees pulled up to their chest or spooning can both be good. Doggy style is good for easy insertion but the receiver won’t have any control of the speed or depth this way, you also won’t be able to see their face to gauge how they are feeling.