Everything You Need to Know Before You Try Pegging

A beginner’s guide to pegging

Although the concept of pegging has been around for a very long time, recent pop culture moments like Deadpool, Broad City, and even a popular TikTok trend #PegAllMen2020, has brought the once-taboo sex act into the mainstream lexicon. In this guide, sex educator Lola Jean tells the KK community what you need to know (and prepare) before trying pegging. 

Have you ever heard of pegging? Chances are if you clicked on this post you’re at least a bit curious. Matters relating to the butt tend to be kept private, but odds are many individuals you know are regularly engaging in anal play. Surprise! Turns out gay men weren’t getting acquainted with the back door because it was the only hole available. Anal play and pegging specifically can be pleasurable for all parties. Whether you’re the giver or the receiver, consider this your guide for easing into the pegging rabbit hole.

What is pegging? 

Pegging is a term that only recently came into our regular sexual lexicon. After years of this act occurring, Dan Savage held a good old fashion listener poll to vote on a name for this specific act where a woman penetrates a man anally. Since then, much like our understanding of gender and sexuality, the term ‘pegging’ has broadened to define itself as an act where one person penetrates another anally using a strap-on. Whether you’re a Tom or Kitten, anyone can enjoy being pegged, though it tends to be people with penises!

While pegging can be an act of dominance and submission, it is also physically enjoyable. For some, pegging is a mentally stimulating activity, reversing the typical roles of penetrator and penetrate. For others, it is solely physically enjoyable, stimulating the prostate and nerve endings around the sphincter making for other-worldly pleasure not able to be achieved by penis stimulation alone. There is something to be said about an enjoyable sex act that takes attention away from the penis. Besides, if there is a G-spot in your butthole, wouldn’t you want to give it a whirl to see what all the fuss is about?

How to talk about pegging for the first time

I know, Toms & Kittens, it can be nerve-wracking bringing up a new desire to a partner. What if they think it’s odd?  What if they don’t want to do it? Remember that while this desire or kink may not be new to you, it could be new to your partner and require some education. There was once a time when you didn’t understand pegging either, right? Whether you are a peggee hopeful or future pegger, instead of approaching your person to engage in pegging, try first expressing your curiosity or interest. Then, give room to formulate their own curiosity before you proposition them.

Step 1

It’s best to bring up pegging—or any new sexual desire—from a neutral standpoint. I like the approach of seeding, which takes the pressure off of one person feeling like they must fulfil a certain act for the other while allowing them to sexualise or enjoy it for themselves. Use a neutral third party—like this article, our video guide to pegging, or a KK class—as a start. 

“I read in this article that pegging isn’t always a submissive act I had no idea! It kinda got me curious about how it can feel pleasurable for my body.”

“Apparently, prostate stimulation feels out of this world. Have you ever been curious about that?”

Step 2

Communicate to your partner why you are interested in pegging and how you imagine it would make you feel. Whether you are watching your favourite pegging porn, talking to other KK members about their experience with pegging, or learning about it in our explicit online class, start to think about why it is that you are interested in pegging. Are you drawn to the power exchange? Do certain positions turn you on most or is it the physical sensations you are imagining?

Quit the ‘spit or quit’

Unlike other areas of the body, the anal cavity does not naturally lubricate itself, so you’re going to need more lubricant than usual! It’s best to use silicone-based lubricants as they are not easily absorbed by the skin and, thus, last longer. If you are using latex condoms or silicone toys, you’ll need to opt for the water-based variety. Don’t be afraid to have more on hand or reapply midway through your pegging session. Lube reapplication is crucial to a pleasurable experience, both for reducing the risk of fissures or anal tears for the peggee and to create that ideal glide and slide for the pegger. 

Pegging and sex – where to start

Hold onto your dildos Toms and Kittens. I know you’re eager to start ploughing holes, but there is more to pegging than lubing up and going slow. The best way to warm up for both parties is by inserting some fingers first. By using our hands we can more easily locate our partners’ pleasure zones than we can with a dildo. This gives us more information and context to their prostate location. Aim your fingers towards the genitals until you feel something slightly harder than the rest of the material around it. Experiment with small tapping motions, moving your finger right to left or keeping static pressure on the area. After all of this tactile engagement, the engorged prostate will make any dildo penetration that follows more pleasurable and effective!

Breathe through the butthole

It’s no secret that breathing is important for Toms and Kittens alike. You’re probably doing it right now! We can use more purposeful breathing when it comes to our sphincters, too. When we take a breath in, our pelvic floor (and our sphincters) naturally engage. On the breath out, our sphincters will naturally relax. Use this to your advantage by doing any insertion on breaths out and use those breaths in to pulsate on the prostate. 

Pro tip: breathing together is a fantastic bonding and non-verbal communication tool

Pegging toys for beginners

The mistake many so often make on their maiden pegging voyage is with the incorrect dildo purchase. Typically an overeager pegger will either choose a dildo that is laughably large or the size of a baby carrot. The itty bitty baby dildos are typically not long enough to reach the prostate and prove equally difficult for the person doing the pegging. That baby carrot is going to slide out of your hole without you so much as realising it until you feel it jamming your inner thigh repeatedly. On the flip side of the size spectrum, ‘go big or go home’ need not apply to your rear end.

Trust me: if you are a person who enjoys anal stretching, you will soon find out. For your first go, it is best to find a toy that does not have a large amount of girth, but enough length to both stay internal and reach the prostate! About 15-16cm or more will be fine. You don’t have to take the entire toy inside of you, but you want to have enough room to work with, especially if your prostate is further back inside your rectum. Renee Denyer of Sh! Women’s Emporium echoes the call for getting a longer dildo than you’d want inside of you as “you’ll lose a couple of playable inches in the harness.” For added relaxation and pleasure try adding vibration either via the dildo, a cock ring, or insertable bullet vibrator. Head over to our guide to strap-on sex (link) for recommendations on the best products and positions to peg to your heart’s content. 

Pegging Complete

Pegging can last as long or short as you both want it to. Pegging doesn’t have to end in ejaculation or orgasm. As queer sex educator Gabrielle Kassell puts it: “pleasure (not orgasm) should be the goal of any sex act, including strap-on sex.” Typically, the butt will tell you when you’re complete with the act. Whether you choose to engage in further anal play, oral, or other penetrative acts, the engorged prostate will make for a very different type of pleasure or orgasm, should it occur.

Incorporating pegging into your sexual repertoire can aid your communication, trust, and capacity for pleasure. If there’s one notion we need to put to rest it is that the back door is an exit-only zone. There is much fun to be had in the rear and it’s about time we laid out the red carpet to this underutilised entryway.

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