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ANAL SEX

How to Prepare for Pegging

by MISTRESS KAY
Published: AUGUST 20, 2021
Presented by SATISFYER
Pegging isn't a spur of the moment kind of thing! Knowing how to prepare for a pegging will get your head/butt/strap-on on the right track.

Are you about to try pegging for the first time? Or maybe you're just looking to make sure that you know what to expect when you find that amazing partner who's excited to enjoy pegging with you!

Either way, there's a surprising bit of prepwork that goes into preparing for pegging. Not only is there a bit of of gear you'll need for pegging, but you're also talking about anal sex - which comes with its own host of things to know.

Safe anal sex practices prevent injury - and enhance pleasure - and having and knowing how to use your pegging gear will also ensure the experience runs smoothly - instead of turning into a frustrating mess. (See how much of a difference it made when I started.)

At a bare minimum, you'll need lube, a strap-on harness, a dildo, and any toys needed for anal prep work (like anal beads). But just owning the toys isn't enough to claim that you've passed the "how to prep for pegging" class. You need knowledge and practice with those items, too.

Of course, how you prep for pegging really depends on whether you'll be the giver or the receiver.

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Getting Pegged: Where to Start

Yes, pegging includes a lot of physical sensations, but that isn't all it includes. There's a lot of mental prepwork that can go into being ready for a pegging too.

This means having a bit of education under your belt. Have you read some of our pegging articles? The biggest takeaway: pegging should never, ever hurt. You might experience a bit of discomfort or fullness - especially if anal sex is new to you - but any sort of sharp, explicit pain means something is wrong. Pain during pegging means that something is wrong; it's not something you should "suffer through".

Pegging is filled with a whole host of seriously pleasurable sensations. There's the feeling of sharing this intimate experience with a partner. You get the pressure and warmth of their body against yours. Of course, driving it all is all of the anal sensations that the dildo can provide. The anus - and inside the booty - are all packed with nerves that respond well to thrusting (for most people). If you have a prostate, there are even more sensations to enjoy - especially if the toy rubs up against the p-spot!

You'll likely find that focusing on your body and your thoughts during this process can help a lot. Your body offers subtle cues about what feels good - and what doesn't - even when you're playing solo. Your thoughts matter too. Worrying about pain, stressing about going too quickly, or being otherwise-occupied can make the butt clench up - which can make anal sex painful. Nobody wants that!

Instead, a focus on how pleasurable pegging is - and the good sensations that are coming - can make a drastic difference in how relaxed you are, and subsequently, how pleasurable pegging is going to be. It's one of those Catch 22's. If you assume you need to "work through" pain, you'll be more likely to make it painful. If you assume everything will be orgasmic, you'll be more relaxed - and less likely to encounter issues.

All of that's to say: if, at any point during your pegging prep, if you find that you're experiencing pain, it's a-okay to avoid the pegging. There's no finish line that you need to rush to. Strap-on harnesses and dildos don't go anywhere. If you're finding any pain during the process, it might mean that it's time to stop focusing on the end goal - and instead, focus on the pleasure of prepping for pegging.

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How to Prepare for Pegging as the Receiver

Your job, as the receiver during a pegging, is to know your body, in and out: understand how it responds to anal sex, and help make the activity as pleasurable as possible for your partner. Since sensations on your end are a given (the pegging dildo goes into your body after all!) part of your job is to help ensure that your partner enjoys themselves too - especially when physical enjoyment on their end isn't a given.

First off, if you don't have any anal experience, you need to stop reading about pegging prep and just worry about getting some anal practice. The act of pegging is all about experiencing penetration in your anus.

It's all about knowing your own body - and being able to relax yourself and help yourself open up to new sensations. It's a brand new erogenous zone to explore: all with orgasmic potential! There are a lot of nerve endings inside of the butt, and spending some solo time exploring those nerves isn't just necessary: it's extremely pleasurable for a lot of people!

Doing this prepwork by yourself also makes it more likely that you'll enjoy the experience. You'll understand where the most pleasurable spots are inside of you - and you'll be able to tilt your hips to make penetration hit those spots. You'll know what sensations feel best - and how to openly communicate with your partner about what you need in order to get the most pleasure out of pegging.

If you don't have any experience with any anal sensations, how do you expect to help your partner ensure that it's enjoyable for you? It's unfair to expect your pegging partner to do all of the pegging - and all of the anal prepwork - for you.

Essentially, to make pegging as pleasurable as possible, you'll want to bring a moderate amount of anal experience to the table - at least enough to be able to communicate when your partner is going too quickly, when a toy is too thick, what diameter your ideal pegging toy should be, and what angles help hit the most pleasurable spots in you. Ideally, you'd be able to communicate what pace, angles, and dildo shapes feel most pleasurable to you.

You, at a very bare minimum, need to understand what inserting something into your butt feels like, what it starts to feel like when you need more lube, and what the differences between mild discomfort and anal pain are. Pegging can be extremely pleasurable - and even orgasmic! But in order to hit that point, you need to have some of the basics covered.

If you're not at that point yet, these anal sex ed articles can help you in your journey of how to prepare for pegging:

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Once you have a bit of anal experience under your belt, though, you're ready to proceed onto what you were originally here for: how to prepare for a pegging:

Regularly Warm-Up: Once the two of you have set a date or an expectation of when you'll want to do the pegging, part of your expectations now include keeping your body in a semi-ready state. If you both have discussed the dildo size you'll be using, you'll want to start practicing anal in order to slowly relax your butt and make penetrating easier when your pegging date comes around.

You'll want to do that through anal dilation. Anal dilation, at its core, is just simply engaging in anal penetration and pleasure for the purpose of relaxing the butt and making it possible to use larger items. It's pretty common, and most people who want to experience anal sex or pegging will need to do some anal dilation to make it as safe and pleasurable as possible.

Read: A Beginner's Guide to Anal Stretching

Even though your anal dilation prepwork is focused on an eventual goal, though, it doesn't mean that it needs to be clinical! There's a lot of pleasure to be found in any type of anal sensation, and focusing on how pleasurable your anal dilation is can be a great way to help your body relax for the main event. If your body expects pleasure during anal activities, it will relax more readily than if it expects other outcomes!

You might also find it helpful to add some breathwork and internal muscle control to your anal prep plans. Using conscious, intentional breath can help you better connect with the sensations in and around your booty. If you're new to breathwork, starting with something as simple as long, deep breaths can make a world of difference. Deeper breathing pushes our body to relax which, as you now know, is a good thing for getting more pleasure out of your anal dilation!

Are you someone who regularly does kegels? If not, why not start?! (We're huge proponents of kegel exercises for sexual pleasure and your health!) Doing kegels can help you consciously control the muscles around the anus. I'm sure you can imagine how that could come in handy right now! If you're finding it difficult to consciously relax your body, you might consider adding kegel exercises to your repertoire - alongside your conscious breathing.

Don't forget about the wonders of sex toys either. While you can do all of the anal dilation you need with just your fingers, using anal sex toys can help prevent muscle strain - and extend how long you can warm-up too. "Set it and forget it" toys like the Satisfyer Booty Call let you wear a plug, and slowly work on your dilation - while also leaving your hands free for other pleasures. You know, like masturbating or otherwise enjoying yourself.

Plus, sex toys can just add even more pleasure! Our bodies weren't born with vibrating fingers (boo!), so anal sex toys might be one of the few ways to get some vibrations to those ultra-sensitive nerve endings. You might want to give the the Backdoor Lover a try. Anal toys also let you reach deeper inside yourself than you could with fingers alone. Essentially, anal sex toys set you up for some serious pleasure during your anal dilation warm-ups.

I recommend being extremely gentle with your anal practice a week leading up to the pegging date itself. You don't want to push things too far and cause soreness that requires pushing back your pegging date. I also recommend that you don't do any anal practice 3 days prior to your pegging date. This reduces the likelihood that you'll have any residual soreness that might impact your ability to enjoy the pegging.

Day-Of Pegging Warm-Up: For the most pleasure possible, I recommend spending some time the day-of getting your anal on. Think of this like pregaming - but for pegging! You get a whole lot of fun while also prepping for the "main event" later on.

To share the experience with their partner, quite a few couples like to do this prepwork together - as a couple - right before the pegging itself. It can easily become part of the foreplay and add even more anticipation about the pleasure to come. Focusing on relaxing - whether that's through conscious relaxation of the muscles or through intentional breathing - can also make a great start to your pegging warm-up.

Small plugs - like the Satisfyer Lolli Plug can easily be slid into the butt to do the heavy-lifting of dilation while you both focus on other activities. You can also actively focus on anal dilation where gently opening the butt (and relaxing into the sensations!) become the main event of your foreplay.

My biggest caveat, though: don't go too rough during your foreplay! Like other parts of the body, the butt can get sore. If you end up prepping with a dildo - and get a bit exuberant with the thrusting, it can take the butt out of commission before you even reach the part where you start pegging. (I'll admit I've been guilty of this on more than one occasion!)

But hey - that just means you get to look forward to doing pegging on another day, and that's not a bad thing!

If you prefer a bit more privacy, you can certainly do your warm-up solo too! In fact, you might find it easier to focus on your breathing and muscle relaxation techniques without the distraction of another person present. While doing your day-of warm-up right before the pegging activity itself tends to provide the biggest benefit, you can certainly do your warm-up earlier in the day if you're short on time.

Either way, all of that anal practicing you've been doing should help; it shouldn't take long to prep your butt for anal as long as the pegging dildo diameter is relatively slim.

Day-Of Thorough Cleansing: Before your pegging date, it's time to make sure your body is as ready as your mind probably is. This will mean different things to different people. If you and your partner discussed and agreed to an enema, that might mean a light clean-out with a few enemas a couple hours before your pegging date. If you didn't agree to that, it might entail spending extra time in the shower on your anal area - and possibly trimming any hairs that might cause discomfort during pegging.

The day of your pegging isn't the time to try new techniques, try an enema for the first time, or use a new soap. Avoid anything "new" day of, except of course the actual pegging!

How to Prepare for Pegging as the Giver

If you're going to be doing the "giving," you've probably already seen quite a few articles about how to ensure you have the "right" equipment and knowledge in order to really pleasure your partner with your pegging skills.

Read: Pegging: Everything You Need to Know to Make It Pleasurable for You and Your Partner

Essentially, preparing to give a pegging just means to make sure you have equipment that makes you happy (and you feel comfortable with!), have a general idea of what position you'd like to do, know the basics of anal safety and going slowly, and are comfortable wielding the strap-on dick and harness.

Here's the basic run-down of what I'd recommend for a giver preparing for pegging:

Know your Strap-on Harness and Dildo: Especially if the harness or dildo are new to you, get used to wearing them. Strap them on and walk around the house. If you can, try humping the mattress or between the couch cushions. Essentially, get used to how the harness feels on your body, figure out the optimal tightness and where you prefer to wear the straps. Figure out if there's a placement for the dildo that provides physical pleasure for you as well. Experimenting with wearing toys like the Double Joy while wearing the strap-on harness can also add more pleasure to the activity.

Understand Anal Safety Basics: While we can hope that your pegging partner comes with their own understanding of anal safety, the honest truth is that a lot of penis-owning partners may not have much information about pegging - and how to do it safely. They're just turned on by the idea of it. You can save you both a lot of annoying heartache by knowing some of the anal basics before you go into it. It all breaks down to: go really slow, use lots and lots of lube, stop if there's any sharp pain, and ensure that you start with smaller toys (or fingers) before slowly moving to the thicker toys.

Decide What Sex Positions You'd Like: I find that it really helps to have a "game plan" for your pegging scene before it's time to actually peg someone. Kinkly has an entire database of sex positions selected specifically for strap-on sex; look at which ones you think could be a good fit for your two bodies - and prepare for doing that position. (Make sure you have the core strength, thigh strength, etc. in order to make it happen).

How You Both Can Prepare for Pegging

Safe sex still matters here! Just like non-pegging sex, you and your partner need to discuss and delegate who will be in charge of various things about your upcoming pegging pleasure.

I first recommend an honest conversation about where you both are in your skill levels. Has the receiver ever done anything anal? If not, shelve the pegging plans and start off with regular fingers and slim toys.

What is the giver's experience level with pegging? Have they done it before, or are they requesting help to make sure things go smoothly?

Are there any specific requests that either partner would like to request - like an internal enema cleansing before the scene for the receiver or that the giver doesn't use a condom on their dildo?

You then might want to figure out if you want these items - and if so, who will be bringing them?

  • Condoms (Easier clean-up after pegging)
  • Towels or Disposable Pads (Easier clean-up after pegging)
  • Lube (Essential! Make sure you account for any ingredient sensitivities.)
  • Gloves (Easier lube application - but can become essential if anyone has long nails!)
  • Any prep toys required for warm-up

If some of these items were specifically bought for the pegging session, make sure to discuss who keeps them afterwards. On the same note, make sure to discuss whether new items NEED to be bought for the pegging. I own hundreds of dildos, but if my upcoming pegging partner says they aren't comfortable using a dildo (as sterilized and condom-covered as it may be!) that someone else has used before, we'll need to discuss the cost of a new dildo, who will cover the cost, and who will keep the dildo afterwards. These are just conversation topics that don't necessarily come up in other types of sex.

Preparing for Pegging Isn't Too Difficult!

See? Preparing for pegging isn't too difficult! While the responsibilities vary for either side of the activity, both sides have an equal responsibility to know themselves, spend time prepping for the activity, and fully bring their half of the partnership to the table. Pegging isn't a one-sided activity, and both partners provide a bit of the work - and both partners get some of the pleasure.

Happy pegging!

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Mistress Kay

Mistress Kay has a fondness for all things sexual. With a house that's quickly running out of room for all of her reading and vibrating pleasures, she spends her free time reading, writing, and learning about the sexual universe with her partners. She can be reached at Kinky World.


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