Anal sex

Preparing for Pegging: 5 Steps to P-Spot Pleasure

Published: MARCH 28, 2023
Pleasurable pegging requires research, practice and the right equipment.

If you're reading this article, you're probably at least considering the idea of pegging your partner. But just like everything sexual, there are no rules that require you to peg your partner.

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So, first off, you should ask yourself: Do you want to peg them? And, if you do, what would make you most comfortable when doing it?

That's where the conversation should start, and it should continue in that vein throughout the entire process. You, your comfort level and your enjoyment are just as important s your partner's. Never let that fall to the wayside!

If you're not really all that comfortable wearing a realistic-looking dildo, don't. If you feel awkward and uncomfortable thrusting, explore sex positions where the receiving partner can do the majority of the movement. If you're worried about looking un-sexy in a harness, experiment with harness types until you find one you love -- or wear a skirt or some jeans on top of the harness and let the dildo pop out.

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READ: How to Build Your Own, Customized Strap-On Kit.

At any point, like anything consent-related, you can change your mind about pegging. Just because your partner wants you to do something doesn't mean that you are under any obligation to do it.

However, I assume you're here because you're kinda curious about how to make this happen.

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So, with that in mind, here are five steps to help you prepare for pegging:

1. Start Practicing Anal

A lot of wannabe pegging bottoms assume their first anal experience will be during a pegging.

This is a problem for a lot of reasons, but mostly because it puts all the onus on you, the harness-wearer, to do all of the work. That's not fair to either of you. You'll both come away with a subpar experience, someone may get hurt and you probably won't feel great afterwards. So let's skip that experience. (I promise, I've been there; done that.)

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Instead, long, long, long before you ever touch a dildo or harness, start adding anal penetration to you and your partner's sexual to-do list.

Essentially, you want your partner to get familiar enough with anal pleasure to communicate about it. We want them to know what's too big, when you need more lube, when you need to slow down and what angles feel best. This is likely going to take at least a few weeks of regular anal play -- and that's a good thing! The more mental "data" they can collect about how it all feels, the better they can communicate during the pegging itself, and that communication is vital!

Your anal exploration will probably look like this:

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  1. Playing with a few fingers around the outside of the anus. (Trim your fingernails first!)
  2. Inserting one finger inside the butt.
  3. Putting two fingers inside the butt.
  4. Potentially moving to three fingers inside the butt (depending on the dildo size you're looking to eventually use)

Those are the very basics. This step alone could turn into an "Anal Sex 101" article in itself, so, please, check out the articles below if anal play is brand-new to you:

2. Buy Your Dildo -- And Use It With Your Hands

Now that your receiving partner has general anal experience, it's time to buy the dildo: You know, the dildo you want to use in a harness during a pegging.

READ: Everything You'll Ever Need to Know About Choosing the Right Dildo for You.

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While you can buy dildo-and-harness kits for easy, first-time shopping, I recommend only picking up those kits if you fit into their size limitations and the dildo and harness style look attractive to you and your partner. Those kits can be easy one-stop-shops for pegging play, but they're also designed be an entry-level kit into pegging -- and you may find that non-entry-level items may make you both more comfortable with the activity.

"You get what you pay for" applies to body-safe sex toys and pegging toys too.

Once you have your dildo, instead of strapping it into a harness, start by simply using it with your hands.

Starting this way provides a few benefits:

  • The receiving partner can experience what anal penetration feels like -- and get a good idea of what feels "right" and what feels "wrong."
  • You can figure out if your dildo is too big or too small. It's very possible the dildo won't "fit" and you'll want to try again with a new option.
  • You can learn how much pressure it takes to insert the dildo into your partner's bum, how long it takes and if you need two hands to make it happen.
  • You can figure all of this out without the added pressure of the dildo being strapped onto your body. Trying to hold up your body weight in an awkward, "not-quite-sex-but-sorta-sex" position while learning all of these new things is much, much harder.

Take my advice and take the easy way out -- so you can focus on the pleasure when you choose to try out your harness!

Like step one, buying the right dildo could be an article in itself. These articles will give you even more advice in your dildo-shopping adventures:

3. Buy a Harness -- And Use It Solo

Now that you have your dildo into mind, it's time to buy a harness. If you bought a standard, flared base dildo, virtually any harness with an O-ring will work. That's pretty much all of them!

Selecting a harness is a very personal choice, and I recommend choosing a harness that looks sexy to you -- and you think will look sexy on you too! How your harness looks and feels to you is one of the most important parts of a strap-on harness; if you're still new to pegging and using average dildos, virtually any dildo you pick will fit into a standard harness, so shop for what makes you feel good.

READ: 5 Things to Know About Strap-On Dildos and Harnesses.

Once you have your harness in hand, put it on and strap in your dildo. I really recommend doing this solo, away from your partner, to alleviate any stress you have about doing something new for the first time. It can be pretty freeing to explore all these new sensations away from the expectations surrounding them.

During the first wear, focus on the feel of the harness -- and work on customizing it to your measurements. I also recommend trying the following activities to get acquainted with your new equipment:

  • Stand in front of a mirror and see how the harness makes you feel. (Bonus points for popping on lingerie and sending your partner sexy selfies to tease them!)
  • Lay on the bed with a scrunched-up pillow underneath your hips and the dildo. Try humping the dildo into the pillow, exploring what movements feel best to you. Side-to-side? Grinding? Pause and try moving the dildo onto a different spot on your body. Does that change the sensations for the better or worse?
  • If you and your receiving partner have talked about sex positions, try to replicate that sex position as well as you can by yourself. Practice thrusting or moving while in the positions you'd like to try together.

Remember: Many people practicing to peg someone for the first time are brand-new to thrusting. While most people with factory-installed penises have been humping and thrusting against things for a while now, you're at square one. It's a-OK (and expected!) if things feel weird, and it's equally as OK if your core or thighs end up too exhausted to continue.

Ready for more help on your harness-shopping adventure? Yep, there's more of that too!

4. Explore Sex Positions

Your sex position is one of the last pieces in our pegging-preparation puzzle.

Here are some sex positions that play nicely with pegging:

The Hinge Position

Hinge Sex Position: The receiving partner is on all fours. The penetrating partner kneels behind them with one foot on the ground and slides inside them from behind.

The Hinge position combines athleticism with deep penetration, providing a twist on doggy style by putting the penetrating partner on one knee. This makes it possible to go super deep, which some couples love!

Binding Spoon Position

Binding Spoon Position: Two partners lay down on their side, facing the same direction. The receiving partner lifts one leg into the air, while the penetrating partner grabs the receiving partner's chest for stability. Penetration is achieved from behind.

A variation on the Spooning Position, the Binding Spoon Position adds different levels of touch and sensation according to where each partner places their arms and legs.

Grand Slam Position

Grand Slam Position: The receiving partner lays on their stomach. The penetrating partner straddles them and penetrates them from behind, grabbing the receiving partner's shoulder for stability.

The Grand Slam Position is a fantastic choice for pegging beginners because the receiving partner is facing away, which can make the giver feel more comfortable while learning new movements.

The Kneeling Fox Position

Kneeling Fox Position: The receiving partner sits on their knees with their arms extended straight out in front of them, propping them up. The penetrating partner sits on their knees behind the receiving partner, grabbing their torso for stability. The receiving partner then

Kneeling Fox offers the benefits of doggy syle sex with a slight variation to make it less strenuous on both partners. Plus, it's great for receiving partners who enjoy deep penetration.

The Tabletop Position

Tabletop position: The receiving partner sits on the edge of an elevated surface, like a table, supporting themselves with their hands. The penetrating partner stands in-between the receiving partner's legs, facing them, and penetrates them.

The Tabletop Position offers the excitement of a standing sex position without being as strenuous as many of these positions can be. It also provides the opportunity for deeper penetration by having the receiving partner rest their feet or legs on the penetrating partner's shoulders.

See, "standard" sex positions may not be a great fit for pegging first-timers. That's because many couples may have discordant heights or weights that make their go-tos a difficult fit. (For example, if your receiving partner is a lot taller than you, you won't be tall enough to even think about penetration in the Open Pike sex position.)

Because of this, I recommend doing a "trial run" with your partner for your expected sex position. Now that you know where you want the harness to fit and where the dildo will hang, both you and your receiving partner can get into the position -- even while clothed.

When I do this with new partners, I find it usually "devolves" into play -- like dry humping them in our clothes until we both get off. A bit of prep work with a lot of fun involved? I'll take it!

READ: 10 BDSM Punishments That Segue Perfectly Into Sex.

The idea is to see how the sex position will work for both of your bodies. Can you both maintain this position, while moving, for a decent period of time?

And, most importantly, does this sex position offer enough support to provide very, very slow and patient penetration? With a dildo strapped to your hips, you won't just be sliding in and going to town -- like you practiced while hand-holding the dildo, you'll likely need to take breaks to slowly insert the dildo into the receiver.

For instance, in the Missionary position, the penetrating partner is left doing an unsupported plank in the air. Holding this for minutes at a time while slowly inserting the dildo is just unrealistic for most people. That's why you'll want to ensure your sex position allows you both to comfortably rest for long, patient breaks mid-penetration without disturbing the dildo's position.

You might need to select a new sex position -- and that's OK! Your previously selected sex position isn't going anywhere, and it'll be there for years to come when you're both more familiar with pegging and everything it entails.

READ: 6 Sex Positions Made for Big, Beautiful Bodies.

5. Have a Conversation

Ideally, you and your partner have maintained open communication throughout this entire process.

Just in case you haven't, though, I want to stress how important it is for you to talk throughout this entire experience.

READ: Sex Communication 101.

Before jumping into pegging, I recommend an open discussion about:

  • How you'll communicate during the experience. Promise to be upfront with one another. Depending on your comfort level around discussing sex, this may look like making secret "code words" to communicate needs mid-play.
  • How you're feeling about the experience. Nervousness is totally normal!
  • How you're going to make sure the harness-wearer has a great time. While pegging provides a lot of sensations to the receiving partner, it can occasionally leave the harness-wearer low in the "physical sensations" department. Make sure you have a plan.

See, pegging is one of those sex acts where the penetrating partner likely has no sensation in the object they're using. Unlike hand-holding a dildo, where the holder can at least see the dildo, in a lot of pegging sex positions, your harness-wearer may not even be able to see the toy!

This means pegging relies even more on open communication than other sex acts might. Did the dildo fall out? Is the penetrating partner sliding further in even though they're trying not to? Would a slight tilt of the hips allow the penetrator to hit the p-spot?

All of these things require open communication and minute-by-minute adjustments.And that's a good thing!

If you and your partner are comfortable enough to communicate, it means your pegging experience has the best chance of being amazing for both of you!

Once you've had a chat (or, ideally, several) it's time for the "big day." You're ready to play with pegging as seamlessly as possible!

READ: A Step-by-Step Guide to Giving Your First Pegging.

How to Actually Peg Your Partner

By following the steps above, you should be fully prepared to deliver a pegging full of serious pleasure, fun and success.

As for the pegging itself? It's going to go down like this:

  1. Enjoy foreplay. Depending on how long you have been looking forward to it, the anticipation is already quite a bit of foreplay. But I always recommend more! I especially encourage lots of physical sensations for the harness-wearing, partner as pegging can be light on physical play for them.

READ: 10 Foreplay Games to Add Some Heat to the Bedroom.

  1. Put on your strap-on harness and dildo. You've already adjusted it to fit your body and figured out how you want to wear it, so this will be a breeze! If you're feeling it, you can let the receiver watch -- and be as teasing as you want to be!
  2. Use your fingers (or a smaller warm-up toy!) with lube on the receiver. This can help pre-stretch the body to get ready for the dildo you have strapped on -- and the visual of wearing your pegging gear while simultaneously penetrating them with another toy can be super hot!
  3. Get into your chosen pegging position. Now that your partner's body is primed and ready for more, you can get into the sex position you've already explored. Since you both know it works for your bodies, now it's just a matter of adding the dildo into the equation.
  4. Add lube. While your partner's butt is probably already lubed up from the warm-up play, more lube never hurt anyone! Add more lubricant to your bottom's entrance and squirt a ton of it onto your dildo. Feel free to make a show out of stroking up and down the dildo's shaft. (If you don't end up dripping some lube onto the bed beneath you, you probably didn't use enough!)
  5. Press the tip of the dildo against the entrance. Instead of you leaning forward, encourage the receiving partner to push back against the dildo. This lets them take the length at their own speed. Expect it to take at least five minutes to get the dildo in, and if it's faster, that just means you get to the fun faster! Exercise serious patience to avoid anyone getting hurt.
  6. Apply the lightest pressure to the dildo. If your partner is unable to push back -- or reaches the limitations of how far they can push on their end -- use the lightest bit of pressure to push the dildo into the receiving partner. If you want, you can slip a hand under the harness and push against the base to push the dildo inside and better control the pressure. Avoid using your bodyweight as the pressure point, as it can be hard to control how much pressure you apply with your entire body.
  7. Ask for feedback. Throughout the entire penetration, you should be talking back and forth. It might only sound like "Yes, deeper," or "Oh, that's good," but this is the most difficult part of pegging -- and active participation on both sides is really helpful!
  8. Start movement! Once the receiving partner is as far down the dildo as they'd like to be, you can start moving! Depending on your comfort level, this may not be all the way to the base of the dildo; it depends on your dildo's width and length. Instead, go to where it's comfortable -- and then move in ways that feel fantastic for both of you! This may be full, in-and-out thrusts, but it also may be grinding motions with micro-movements that target the p-spot or push the dildo base into the clitoris. It's all about what you enjoy.

That's really it, though! You're pegging someone! You did it!

Pegging Sex Toys

As you explore the world of pegging beyond this first time, you might consider adding some sex accessories like the:

These toys can help add pleasure (and reduce pain!) during pegging. However, they can add a bit of complexity at first, so I recommend going without them for your first few peggings.

Once you're comfortable, though, they can be great ways to add more sensation and functionality to your pegging play!

Conclusion

Pegging is a popular sex act for good reasons: It can feel amazing, look amazing, help you experiment with power dynamics and open up a whole new world of pleasurable possibilities for you and your partner! However, like anything you're trying for the first time, preparing to peg your partner requires planning, practice and -- most of all -- good communication.

For more advice on how to prepare for pegging and make it go smoothly, I'd recommend these articles:

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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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