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ANAL SEX

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

by MISTRESS KAY
Published: SEPTEMBER 20, 2021
Presented by KINKLY SHOP
These common barriers often keep couples from enjoying pegging - but they don't have to.

[Editor's note: Pegging is the term used when a strap-on is used to anally penetrate a partner. Generally, it refers specifically to a woman wearing the strap-on and a man as the receiving partner. We have used gendered pronouns to reflect how the term is used, but we know body parts don't equal identity!]

For heterosexual couples who have delved into the world of pegging, it's hard to turn back. After all, aside from being extremely pleasurable and orgasmic, it can be an easy way to "reverse" the standard power roles in a relationship and get to know each other on a more intimate level. He'll get more experience on the receiving end of pleasure while she'll get more experience on the "providing" end. And, of course, it can feel fantastic for both partners!

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Read: Power Play: The Difference Between Tops, Bottoms and Switches

Now, if you do try pegging, I want your experience to go as swimmingly as possible, but things happen. Especially with a sex act like this, where there are multiple variables that most couples are unfamiliar with, things can feel frustratingly difficult. With that in mind, here are some common barriers that keep heterosexual couples from enjoying pegging - and how to fix them.

All of these are written from the point of view of strap-on wearing woman who will be pegging the butt of a penis-owning human, but suggestions could apply to couples of all sexes.

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He's Terrified It'll Make Him Gay

This seems to be a common complaint, and it's one that's mostly in someone's head. This is usually something he will need to come to terms with on his own, but it can help to regularly reassure him that it isn't the case . (Or, you can send him over to sex blogger JoEllen Notte's piece: If Anal Sex Makes You Gay, Do Tacos Make You Mexican?)

Read: 5 Rules of Anal Play for Straight Men


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We're Scared about the Mess

Yeah, shit happens. You're messing around in a part of the body that is regularly used for waste. Similar to the vagina (and the blood that happens) this is just a regular, biological function that this area is used for.

However, it's still something that freaks a lot of people out to the point that they may avoid anal sex or pegging entirely because of this fear! Well, that's no good! Aside from accepting that it's going to happen on occasion (and it's going to happen at some point if you engage in enough pegging sessions), it helps to do a few things:

First, make sure the receptive partner is eating a good diet - and having solid bowel movements. The time to play with pegging isn't after he's been sick with the stomach flu. Having your partner eat a full, fiber-rich diet and choosing to only play after he's had a solid movement within the last 4-6 hours can really help.

(This, of course, assumes that solid and firm bowel movements are physically possible for him. If that isn't the case, pegging is still very much on the table for most people, but you might consider using more barrier methods because of an increased chance of mess. IBS and Anal Play: Why It Doesn't Have to be a No-Go has some great tips.)

Second, some people really enjoy using enemas to clean out the area before play. After an enema or two, the interior of the body could be near-spotless, and you're much less-likely to run into anything that might offend the two of you. (Need help on how to do an enema? I got you.)

Third, you can always use barrier methods to keep your contact of any "mess" to a minimum. Puppy pads or medical chucks can protect your bedding and provide an easy, disposable place to place "dirty" objects. Gloves keep any mess off of your hands - and make it easier to transition between cuddling and pegging. Condoms mean that any potential "mess" can easily be stripped off the dildo and tossed into the garbage without needing to handle it.

Read: How Do I Prepare for Anal Play?


We're Not Sure Where to Start

Weirdly enough, a lot of couples get stuck before they even attempt pegging. After all, this is a whole new type of "sex" - and it's a type of sex that requires a lot of gear! This can make it extremely, extremely difficult to know where to start.

This is where beginner pegging kits can come in. If you've been around for my other pegging advice, you know that I generally recommend purchasing your strap-on harness and dildo separately. Not only does this ensure that you're more-likely to get something that works for both of your bodies, but it also means you can customize your kit to exactly what you need.

At the same time, having the knowledge you need to actually make educated, informed, and right-for-you decisions about dildos and strap-on harnesses is something that comes with practice, experience, and knowledge.

It's a Catch-22 - and not a fun one at that.

That's where a beginner strap-on harness kit can really come in. Especially since they're on the lower-cost end, these kits can give you a starting place to start to experiment with pegging - and figure out what you like in your strap-on harness and dildos. This gives you a jumping point to figure out what it is you actually want when you want to upgrade your equipment.

A beginner's strap-on harness kit can help you answer some questions like:

  • Where do you want your strap-on harness to sit on your hips?
  • What dildo size can the receiver comfortably take?
  • How long does the receiver want the dildo to be? How long does the giver want the dildo to be?
  • Do you need specific dildo sizes and lengths for specific positions?
  • How do you wash your strap-on harness? Do you wish it washed differently?

Plus, even after you "upgrade" parts of your strap-on kit, the dildos included in your beginner's kit can still be very functional. They can become your warm-up toys - or they can be just-as-easily used in your new strap-on harness too!

One of the latest pegging beginner kits to get the scene is the Sportsheets New Comer's Strap-on Special Edition kit. Everything about this kit was designed to be simple for beginners to use. The interchangeable O-ring is fastened on by Velcro straps - which makes it a breeze to swap out. The included dildo is extremely slender and designed to be your first introduction to anal play. Plus, the harness fits hips up to 72"!

And here are some other beginner strap on kits:


Pegging Hurts Him!

This is a big one for many couples, and it's usually caused by a couple of different things.

First, he could be nervous. Like any other muscle around the body, the butt tends to tighten up when the person is nervous. This can make penetration of any sort much more difficult. The solution here is to ensure he's relaxed, engage in lots of foreplay, and start extremely small - maybe even with just a finger - to show him that things can feel pleasurable. He'll start to relax from there.

Second, it could be your dildo size that's the problem. One of the big benefits of using a strap-on is that YOU get to choose your own dick size. Want to be gigantic? Done. Want to be slim with a p-spot curve? You got it. You can strap-on and change your "dick" every time you play. With that being said, even on a day-to-day basis, what a person will be able to comfortably "take" may change.

Read: 8 Tips to Picking a Dildo That Will Rock Your World

If your partner is experiencing pain, consider going down to a smaller dildo. Especially if you're both new to this, some of the dildos included in "beginner" pegging kits can be surprisingly large! Consider a slim dildo with a diameter of less than one inch if he's having problems. Nobody says that your anal sex has to include a dildo of biological human size. Again, the fun of pegging is that you can use a dildo that's barely thicker than a finger! And of course, remember to do a thorough warm-up with lots of foreplay and using your actual fingers beforehand.

Here are some of my favorite beginner dildos to choose from:


The third and final factor when it comes to painful pegging is amount and type of lubricant you're using. Lubricant tends to dry up over time, and with that, it'll start to become uncomfortable. Especially if using a water-based lubricant, take the time to pull out on occasion and slather your dildo in another layer of lubricant. I personally like to keep gloves on-hand for this. I'll pull out of my partner, snap on a glove, use the gloved hand to re-lubricate the toy, then slide back in and take off the glove. That way, there's no lubricant/mess on my hand, and I can go right back to gripping onto my partner.

Read: What are the Best Lubes for Anal Sex?

Here are some of my favorite lubes for pegging too:



We Can't Figure Out the Best Pegging Positions

Now, this can be a tough one for some people. After all, you're basically trying to insert an inanimate object - that you can't feel - into your partner's butt. To top it all off, many strap-on wearers don't have experience being the penetrator. That's enough to give anyone performance anxiety!

First, consider blindfolding your partner. It's a small step, but knowing that his expectant eyes can't watch you can honestly help quite a bit when it comes to finding your groove.

After you've done that, it'll be time to experiment with a few different positions. You're, essentially, looking for sex positions where you can control the rate of penetration, you might be able to grind for clitoral pleasure, and any height differential won't matter. Turns out, a lot of sex positions are specifically designed for the penetrator to be the taller partner!

To start your journey, Kinkly has an entire section of strap-on friendly sex positions. It's really a great place to start.

One of my favorites for beginners is the Bound Love Triangle Position. While it's shown with Liberator sex furniture here (and that makes it really easy to achieve), it can be done with a well-positioned bed, couch, or ottoman too.

Bound Love Triangle Position. Doggy Style position with receiving partner kneeling and propped up on sex wedge and ramp.

Another great option is the Mermaid Position. With the receiver's legs resting on the strap-on wearer's shoulders, this eliminates any height difference and makes it easy for the strap-on wearer to control depth. It also can feel a bit more intimate as you watch the receiver's face contort in pleasure. This can easily be done on any piece of furniture that happens to be at the strap-on wearer's perfect hip height.

Mermaid Sex Position

There's also the Reverse Missionary Position. This one might be a bit more advanced - since the amount of flexibility required can leave your receiver feeling vulnerable. It also makes the strap-on harness wearer a bit more of the "center of attention". However, it leaves a lot of space for grinding and feelings of control - which can be a whole lot of fun!

Above all, realize that getting good, working sex positions is just a matter of experimentation and time. You just have to give things a try! If that's still proving frustrating, consider purchasing a longer dildo for your harness. A longer toy can offer easier penetration and more sex positions.


The Harness Doesn't Fit Right - I Don't Feel Sexy

Well, boo! Nobody wants to feel unsexy during a sex act! No wonder you're having some problems.

First, it could be in your head. After all, this is a whole new type of "attractive" that you've never really seen before! How often are women featured in powerful positions wearing strap-on harnesses in the media? It's even a niche in porn! It can be hard to pull together your current definition of "sexy" - and make it fit with wearing a strap-on harness and cock.

What's in your head definitely matters, of course, but it may be worth asking your partner to reassure you about how you look in the harness - or practice taking some sultry selfies in your harness and see how positively he reacts when you send them to him! Consider wearing some of your prettier lingerie underneath the harness if you want a little boost of confidence.

If that isn't doing it, the next solution is just to honestly purchase a new harness. This may not be in the cards for everyone, and high-quality strap-on harnesses can be expensive - but it can be worth saving up to ensure that you feel hot and aroused during this sexual activity.

Manufacturers now make a large variety of different types of harnesses. Try to steer clear of the cheaper ones for a better fit. Spareparts, in particular, makes some sultry-looking harnesses - including some that look straight-up like a lingerie strap-on harness!

If your harness doesn't fit correctly, though, again, it might be an issue of purchasing a new harness. Different harnesses fall differently on different body types. Some harnesses are going to sit high on the hips and near the hip bones. Others will rest right along a straight line around the thighs from the pubic area. Depending on your body and how you carry your weight, you might find some harnesses more comfortable than others. When purchasing your harness, especially if you're larger or smaller in frame, make sure to pay attention to the manufacturer's maximum or minimum guidelines.

In general, if you're a bigger person, "one size fits most" harnesses tend to end at about 42" hips. Some stand-out strap on harnesses that are size-friendly include the Sportsheets Divine (up to 82" hips), Sportsheets Sunset Lace Corsette (up to 72" hips), and the Sportsheets Pleather Harness (up to 72" hips).


I Have Problems Putting on the Harness

This one can be a tough one, and it's honestly something that only gets better with time.

To get started on solving it though, though, start practicing putting on the harness in private - without your partner around and not during sex. Adjust all of the straps to the perfect adjustment for you. This includes the smaller ones and the below-the-butt straps. Now that you have things perfect (and this is a fun time to take photos of yourself!), just undo one of the fasteners - usually one of the hip ones works best – and step out of the harness. Next time you're ready to play, just slide in the dildo and step into the harness, then fasten up that single buckle. Perfect fit!

However, if the idea of stepping into the harness still makes you nervous, consider putting on your harness before you initiate sex entirely. After all, it'll be a great surprise if you come out from the bathroom with the dildo hanging between your legs and ready to go. Talk about a lovely visual!

Another solution is to purchase a harness that's easier to put on. Panty-style strap-on harnesses can just be slipped up the hips like a regular pair of panties. The Spareparts Joque uses the magic of Velcro to fasten onto the body in seconds.

If you're having issues with all of the buckles and fasteners, remember that leather-crafted harnesses tend to be the most complicated of the harnesses out there. Since leather doesn't really stretch, it relies solely on buckles and fasteners to get it to the perfect fit. This can lead to a hot visual (when it's on), but it also takes longer and is more complicated to put on than other alternatives.


Strap-On Play Does Nothing for Me Physically

This is also a common complaint for many strap-on wearers with vulvas. They enjoy the experience of pegging and want to do it with their partner, but they just aren't getting the physical stimulation they need to get off. (This was a large part of my problem, too, before I found some alternative ways to enjoy myself).

The problem usually lies in a couple of places, so it may take some investigation and experimentation to figure out how to solve it.

First, the issue could be the harness. If the harness has the dildo sitting somewhere away from the clitoris, your body won't experience the pleasure of having the base of the dildo rub up against the clit with every thrust. Fix this by finding a strap on harness that rides lower and positions the dildo on top of the clit.

Second, the issue could be the position itself. Some positions will lend themselves better to pushing and grinding the base of the dildo into the body. Fix this by experimenting with positions - and finding positions where your receiving partner still gets some pleasure while you're grinding against the dildo's base.

Third, it could be the dildo itself. Some sex toy bases are going to be too large or concave to provide regular stimulation to the clitoris. To help fix this one, consider adding a dildo pleasure attachment to the base of your dildo like the BumpHer, Honeybunch, or Shagger. You could also get a dildo that comes with a built-in base for clitoral pleasure like the Wet for Her Fusion.

Finally, not everyone gets off by grinding against their dildo. If that's you, adding some vibrations can really up the pleasure potential. See if your strap-on harness includes built-in pockets for bullet vibrators. Sliding something like the Tango X into your strap on harness can add additional vibrations for more sensation. If you're a fan of internal stimulation, it might also be time to consider adding a dildo, Kegel balls, or a strapless strap on like the Strap-on-Me Vibrating Bendable Strap-On toy to add more stimulation during the act. You also might consider a vibrator like the Enby by Wildflower to add additional vibrations.

That being said, pegging is still not likely to be something that will provide an "effortless" orgasm for most. You might consider engaging in a lot of foreplay beforehand so your body is already worked up and ready to go.

Finding sex positions that allow you to stimulate yourself can help even out the orgasm potential here. Pick a sex position that doesn't require the use of your hands then loosen up your strap-on harness a bit. Now, you can reach your hand between the two of your bodies to pleasure yourself while still moving your hips to peg your partner. This can take a bit of practice, but the ability to pleasure yourself can be worth it!

You also might consider relocating the dildo entirely to somewhere away from your clitoris. Using a thigh strap on harness leaves all of the vulva open for pleasure - which means you can be having strap on sex while also using your favorite wand vibrator (like the LELO Smart Wand Medium) at the same time. This is a great way to ensure everybody gets an orgasm.

If you prefer, you can also accept that pegging won't be a physically stimulating experience for you. There are lots of other ways to get off after you've finished pegging your partner - or before! Consider making your partner "earn" his pegging by getting you off beforehand. People engage in lots of intimate acts that don't offer self-stimulation at every given moment - such as oral sex. This might just be another one for the two of you.

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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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