The Complete Guide to first time Pegging for Beginners

The Complete Guide to Pegging for Beginners

The idea of pegging is alluring and daunting in equal measure to many people. It also seems to be becoming increasingly popular with lots of people wanting to have their first pegging experience. When I first entered the sex positive community in the late ‘00s, barely anyone was talking about it. Now, pegging is so mainstream that it has featured in hit TV shows such as Broad City and The Bold Type.  

Read on to learn everything you need to know about pegging as a complete beginner!

What is pegging?

The term was coined in Dan Savage’s Savage Love sex advice column in 2001. It refers to a person with a vulva (usually a cisgender woman) penetrating a person with a penis (usually a cisgender man) with a strap-on dildo. 

Wait, straight men like getting penetrated?

Yes!

Your sexual orientation is about who you’re attracted to and has nothing to do with the specific kinds of sex acts you enjoy. Many men who have sex with women enjoy the thought or reality of being penetrated. 

There’s unfortunately a lot of stigma attached to receiving anal penetration as a man, especially as a man who identifies as straight. But this is rooted in homophobic and misogynistic societal beliefs which state that to be penetrated is inherently feminine. 

Say it with me now: wanting to be pegged does not change my sexual orientation. 

Why do people like pegging?

The most obvious reason that people with penises like being pegged is because they have a prostate. This walnut-sized gland, located between the bladder and the penis just in front of the rectum, can feel incredibly pleasurable when stimulated. Some people even find they can orgasm from prostate stimulation without any penile contact whatsoever! 

Physical pleasure is not the only reason some people enjoy being pegged or pegging their partner. It can also be an incredibly intimate, sensual, and bonding experience. 

Some people also enjoy incorporating pegging as part of their BDSM play. While this is most commonly portrayed with the person being penetrated in a submissive role, it’s also entirely possible to flip the script. Are you a dominant person with a prostate who wants to be pegged? Why not order your submissive to don their strap-on and service you until you’re satisfied? 

As with many sex acts, the reasons people enjoy pegging are as diverse as those people themselves. Instead, ask yourself this: what is it about pegging that appeals to you

How to bring up pegging with your partner

Are you curious about pegging your partner or being pegged, but not sure how to bring it up with them? I recommend raising it when you’re not already having sex or about to be having sex. Wait until you’re in a safe space and a relaxed mood, then broach the topic with an open mind and see what they think. 

If it helps you to open the conversation, you can talk about a porn scene you watched or an erotic story you read. You might also say that you read about pegging and thought it sounded really hot. 

Ask your partner what they think and really listen to the answer. They might be turned on, turned off, intrigued, or excited. They might also say it’s not for them and, hard though that might be to hear, you do need to respect it. 

If they are into it or at least curious, you can start exploring by fantasising, watching porn, or reading erotica together. You can also make a super sexy date night activity out of visiting a sex shop (or browsing one online) to choose a strap-on dildo and harness. 

How to choose a strap-on harness

The right harness is crucial to getting the most out of pegging, and lots of different considerations go into choosing the right one. Take your time to browse and see all the different options that are out there. 

Here are a few things to consider as you choose a harness:

  • Sizing. Take measurements of your waist, hips, and around your thighs. Check the measurements of the harness before you buy to make sure it will fit you comfortably. Many harnesses are at least somewhat adjustable or come in different sizing options. 
  • Aesthetic. Do you want something masculine-coded, like a pair of sexy boxers, ultra feminine, or something in between? Do you want something with a leather, bondage-inspired look, or something a little softer? 
  • Comfort. You know your body best and what works for you. You’ll enjoy your pegging adventures a lot more if you’re comfortable. 
  • Flexibility. Some harnesses come with interchangeable O-rings, allowing you to use different size dildos. I love harnesses of this type because they are so much more versatile. 

When you’ve found a harness you like the look of, take the time to read some reviews. Go beyond the product pages (which tend to show the best reviews prominently) and read what sex bloggers and adult product reviewers have to say. 

How to choose a strap-on dildo

I always advocate for silicone as a material for strap-on dildos. Silicone is completely body-safe, easy to clean in a pan of boiling water (or the dishwasher,) and feels lovely and smooth to the touch. 

If you’re new to anal play, choose a smaller, slimline dildo to begin with. Pegging can be very intense and even a small toy can create an amazing full feeling. The Apprentice and Peg dildos from Godemiche are specially designed for anal play and are a great place to start! You can always move to a bigger toy later on, if you wish. 

Whatever dildo you choose, always make sure it has a flared base. This will ensure it stays firmly in place in your harness, and is also an important safety concern. Never insert anything anally if it doesn’t have a pronounced base, large handle, or some other means of ensuring it cannot get completely sucked up inside. 

The right lube for pegging

Any kind of anal play requires lubrication, and lots of it. The anus isn’t self lubricating and without sufficient lube, you can hurt your partner or even tear their delicate anal tissue. 

A high quality water based lube is great for pegging. It is versatile, easy to clean, and safe to use with silicone sex toys. Sliquid Sassy is my favourite, but there are numerous options on the market. 

Whatever type of lube you choose, you need to use plenty of it and reapply it often. There is truly no such thing as too much lube. 

A word of caution: many “anal lubes” contain numbing agents such as benzocaine. Avoid these! Numbing the area not only means you’ll miss out on a lot of pleasure. It also means you risk not noticing if something is being torn or injured. Pain is your body’s way of telling you something is wrong, so do not cut off its access to those important signals. 

Starting slowly 

The first time you experiment with pegging, you (probably) won’t get to the point of full penetration. That’s okay! With any sort of anal play, it’s actually smart to start slowly and work your way up. This gives the receiver’s body time to adjust and get used to the new sensations. 

You can work up to pegging by inserting just one or two fingers to begin with. If that’s all you do for your first session (or more,) then that’s absolutely fine. Only move on to the next stage when the receiver is comfortable and enthusiastically ready for it. 

Another way to build up to pegging is to play with butt plugs. Plugs sit just inside the anus and help to gently warm you up and stretch everything out. You can even wear one around the house (or out, if you’re feeling extra adventurous) for a few hours before play if you need a longer warm-up. Try a Godemiche Anal Set to start you off. 

Slow and steady is the safest and most pleasurable way to get into pegging. So take your time, work your way up slowly, and don’t put too much pressure on yourself or your partner. It’s best to go into pegging with as few goals and expectations as you can. There are no prizes for taking the biggest toy or reaching full penetration the fastest!

Communication is critical

Good communication between partners is the absolute number one ingredient for any kind of good sex, pegging included. You can’t read each other’s minds, so you’ll need to get explicit about your desires and your experience. 

Check in often, especially when you’re first starting out. If something doesn’t feel quite right, pause and adjust. And if something hurts, stop straight away. Anal play can be intense and occasionally even uncomfortable, especially for new players, but it should never be painful. 

Ultimately, the only “right” way to do pegging is the way that is safe and feels the most pleasurable for both you and your partner. So explore, communicate, and keep an open mind. Most importantly, have fun!

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