Pegging 101 - A Beginner’s Guide to Anal Strap-on Sex

Pegging 101 - A Beginner’s Guide to Anal Strap-on Sex

An article by Poppy Lepora of Self & More

 

To the uninitiated, pegging might sound like something you do when hanging your laundry out to dry. Nope! Simply put,

 

pegging is the act of having anal strap-on sex with an eager bottom.

 

The act has received a lot of attention over the past few years, being thrust (no pun intended) into mainstream awareness through references from Broad City to Deadpool (to name a few). Pegging even has several dedicated hashtags on TikTok (or PegTok as it’s so affectionately called) where videos on the topic have amassed over 324M views.

 

When the term Pegging was coined by Dan Savage back in 2001 it referred to someone (usually a cis woman) performing anal strap-on sex with their partner (usually a heterosexual cis man) - but let’s not limit ourselves with labels here. As far as I’m concerned, pegging is simply the act of penetrating someone’s ass with a strap-on. While anal sex can be gratifying for people of all genders and bodies, the pleasure potential is particularly ample for people who have a prostate (often referred to as the g-spot of the ass).

@jzyblws I’ll get the strap u get on all fours LETS GO #pegtok ♬ original sound - Patrick Murphy

Despite the act’s memeability, for many, pegging is still considered a subversive act. Somewhere along the way, popular culture adopted the idea that external stimulation is the best way to receive pleasure as a cishet man and penetration is the default way to receive pleasure as a cishet woman. As a long-standing member of the LGBTQI+, let me let you in on something that our community knows all too well:

 

the real fun starts when you throw these ideas out of the window and re-write your own pleasure rules.

 

Some people might see pegging as a dominant act, (a cocksure-attitude is a possible side-effect of donning a strap-on, FYI), but it isn’t an inherently dominant thing. Like any sexual act, it can be performed as lovingly or sadistically as desired by both parties.

 

So, let’s get into it, shall we?

 

Talk it over

Before you even think about donning that harness or spreading those cheeks, it’s important to have an earnest conversation with your partner-in-pegging about both of your expectations, desires, and boundaries. Ascertain whether they’ve indulged in anal play before and think about setting a safe word if your play is going to involve submission and domination.

 

To help relax, take a partnered bath with our soothing, luxurious tonic before playtime.

 

The Tools

To start your pegging exploration there are a few basic tools of the trade that you’ll need to get hold of: a strap-on harness, a dildo and some thick water-based lube.

 

Buying your first harness can feel intimidating but the most important thing is that you feel comfortable in it. Most sex toy stores will sell a simple pegging kit that takes the stress out of choosing. As the pegger (the top), if you’re new to strap-on play then you might want to spend some alone-time practising how to slip it on and fasten it. Wear your harness and new appendage around the house to get used to it - notice how you feel with a rock-hard dick hanging proudly around your hips and see how the dildo responds as you move in different ways. You could even practise thrusting into a pillow or the sofa to see if you can find a natural rhythm and hone your technique.

 

As for dildos, the right size and girth will depend on the bottom’s (or the peggee’s/ the person receiving the dildo) previous anal experience level. Choose a dildo that is slim and smooth for easy penetration or that has a slight upwards curve if you want to offer some extra p-spot stimulation.

 

Lube is important as the anus is not self-lubricating (and nor is a dildo) so you’ll need plenty of the wet stuff to keep things slick and comfortable - opt for one with a thick formulation as it’ll last for longer.

 

Warming up

As with any type of anal play, skipping straight to penetration is not advisable.

 

Start with all the usual types of sexual play that you and your partner enjoy - kissing, touching, teasing, talking dirty - whatever gets the blood flowing.

 

Now, time to say hello to the bootyhole. There are plenty of sensitive nerve-endings around the anus and touching and licking is a great way to begin. Once you’ve given the outside of the booty all the attention it deserves, with the consent of your partner you can begin to explore penetration. Start with fingers or butt plugs to slowly stretch the anus, only advancing to the dildo when the bottom is good and ready. Have your lube on hand and re-apply liberally whenever needed.

@polypopppy

~ subtle ~

♬ original sound - gorgeyhuns

Positions for Pegging

The missionary position (and variations of it) is ideal for first-time peggers. With the peggee (person being pegged) laid on their back, you’ll be granted easy access to both the anus and penis and a great vantage point of the peggee’s face. This is key if anal play is new territory for you both as being able to read your partner’s facial expressions will give you a greater idea of how comfortable they are and allows for lots of eye contact and non-verbal communication.

 

Placing a cushion or sex wedge underneath the bottom’s bottom will make the anus even easier to reach and will give the top a better chance of stimulating the prostate (which is located behind the front wall of the rectal passage) with each thrust.

 

If you want to add an element of power-play, then doggy-style is ideal for turning the peggee into your plaything - if they’re excited by the prospect of being restrained then tying their wrists or ankles to the bed is an excellent way to get them into the submissive mindset.

 

The Magic Word: Communication

How many times have you heard a sex educator tell you that communication is key? That’s because it truly is. Both the top and the bottom should check in regularly to give each other words of encouragement, guide each other towards more pleasure or let your partner know if something doesn’t feel right.


If you’re lost for words, then try these phrases:
You’re taking it so well, do you want more?
Does that feel as good as it looks?
That was great but I need to take a break now
Could you use more lube, please?
I love watching you fuck me, do it faster, please.

 

Make Pegging More Pleasurable for the Pegger

While there’s a great deal of pleasure to be had simply from relishing in the satisfaction you're giving to your partner, as the top you might find that you want to supercharge the experience for yourself. Here are a few ways that you can do that:

 

Slip a small vibrator into the harness, like the We-Vibe Moxie
Use an internal dildo / strap-on, like the Strap-on-Me Vibrator
Add a stimulating dildo base, like the BumpHer
Use grinding thrusts that stimulate your clitoris

And of course have fun! Sex should be pleasurable and playful and pegging is no exception to that.

 

Aftercare is an important aspect of new play and our soothing and antimicrobial salve is a great wait to soothe microtears and post play discomfort

 

Shop our trio for a full regimen

 

Poppy Scarlett is the founder and CEO of Self & More Sex Toy Boutique. She is a polyamorous, bisexual kinkster who is dedicated to dismantling the stigma that still surrounds masturbation and pleasure.

Further Reading:

Mind the Pleasure Gap: Gender inequality in the bedroom
What you shouldn’t assume about queer sex
Shedding sexual shame
Queer sex can be bad too
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