Best Pegging Positions for Beginners

A plus-size woman in dark red panties is wearing a strap-on harness and dildo. Her partner is wearing a similar pair of panties and backed up against the dildo of the strap-on harness wearer. Image for Best Pegging Positions for Beginners.

When you’re first learning to use a strap on harness and dildo, figuring out how to move your body is HARD ENOUGH. You shouldn’t have to spend time thinking about what sex positions will be best for your first pegging experience. So, with that in mind, take my years (upon years!) of knowledge and enjoy some of my best pegging positions for beginners – in addition to my advice for each position to make it go as smoothly as possible.

(And a special thanks to Kinkly for allowing me to use their sex position imagery for this post for illustration purposes. You do NOT want to see me attempt to draw out sex positions. I’m a photographer and educator – and not an illustrator – for a reason.)

Grinding on Top of His Butt from Behind

The Grand Slam Position

This is, by far, the best pegging position I recommend anytime I teach someone how to peg. That’s for a couple of fantastic reasons:

  • It makes height irrelevant. Especially if you’re pegging someone who’s taller than you – which a lot of bottoms tend to be in the femdom sphere – height can get in the way of getting sex positions to match up. It’s almost like most sex position sites expect the receiving partner to always be shorter. Since you both are doing some version of laying down with this one, height becomes irrelevant.
  • This beginner pegging position has the strap-on harness wearer taking the bottom from behind. This means you don’t have to worry about your bottom watching as you fiddle around with the harness or struggle to get things into the right position. They’re also extremely comfortable, so they’re not going to be impatient to get things started. They’re just laying on a bed. Who can complain about that?
  • This position ALSO allows for a bit of variance to keep your muscles from getting tired. Lean forward and put your body weight onto your arms when you want – or sit up straight and use just your core and hip muscles to do the thrusting motion. Lean back if you have the quad flexibility for a different angle. Easily flip back and forth without much of a delay or need to reposition the dildo.
  • Finally, if you have a vulva and clitoris, you can easily modify this position to be more of a “grinding” motion instead of an in-and-out position. This can easily let you grind your clitoris onto the base of the dildo. This is the easiest pegging sex position for me to orgasm in, and other femdoms have told me the same. It might be for you too.

The only downside? You’ll want to make sure it’s a soft surface you’re pegging on if your partner owns a penis. Some people might find grinding the penis (with two people’s body weight on top of it) into a hard floor to be unsurprisingly uncomfortable. This sensation can be exacerbated if the harness wearer is a full-bodied individual.

(Into ball busting or CBT? That “downside” may not be so much of a downside! A reader reached out to say that they love this position just because it’s so uncomfortable on their penis during pegging. Ahhh, the wonders of human sexuality!)

The final downside? You can’t see your partner’s face during this pegging position either. That one sucks a bit.


Him on Top

Image from: https://www.kinkly.com/definition/482/the-cowgirl-position

The Cowgirl Position

I find that a lot of pegging beginner bottoms don’t necessarily imagine this pegging position as “viable” when fantasizing about pegging. Something about the “pegging” is supposed to involve them laying back and doing nothing while a femdom does all of the work to “dominate them!” while the femdom gets minimal physical sensation out of it all. (Please read that with as much disdain as I feel while writing it.)

This position forces the pegging bottom to do some work – but it also makes things a lot easier on both ends of the dildo.

This position is a really simple, face-to-face position that keeps the penis and balls from getting squished under body weight. This means that the penis is available for stroking, you both can still talk and easily make eye contact (and enjoy your bottom’s lovely expressions!), and you can put your hands pretty much anywhere on their body. Since the strap on harness wearer just needs to put on the dildo and lay back, it takes a lot of pressure off of the wearer.

Since I find that a lot of pegging interest starts with the bottom in a couple, this can be an easy way to help reassure the strap on harness wearer and make the act more appealing for a reluctant harness wearer too.

At the same time, this position makes it safer and easier for the bottom. The bottom can feel where their hole is, and they can control the entire depth and speed of penetration. This makes for less painful insertion, and it ensures that the dildo finds its way comfortably into the hole. Since the bottom determines initial penetration speed, it’s much-more-likely that penetration will go at the speed the bottom’s body needs it to go – and position fatigue, excitement, nervousness, or unawareness won’t necessarily get in the way of a proper, safe penetration.

At the same time, since the bottom is “on display” for the top, this also can feel very vulnerable and bring out feelings of submission – despite the receiver being on top. You can add even more power exchange sensations if you want – just add some dirty talk into the mix.

This sex position for pegging tends to go over best when the pegging bottom has some previous experience with anal play or pegging in the past. (But then again, I don’t recommend doing any sort of pegging with a bottom who has zero anal experience anyway.)


Him Backing Into Me While I Sit on the Edge of a Couch

Image from: https://www.kinkly.com/definition/14662/the-hinge-position

(I’m out here inventing my own sex positions. The “Hinge” position is the closest visual I can find. Imagine the penetrating partner is sitting on the very edge of a chair or couch with both legs spread wide. The rest of the position matches up.)
The Hinge Sex Position

I’ve found this to be a (surprisingly!) great position for us. When I sit on the very edge of our couch with my legs spread wide, my dildo hangs between my legs, and my partner can easily “back up” onto the dildo. It’s essentially a version of “doggy style”, but it doesn’t depend on my bottom’s thigh height and mine matching up; we just need a chair, couch, or bed that’s about butt height when my partner is on their hands and knees.

Since the pegging position includes the bottom pushing back with their full body weight, it also can add some really lovely clitoral stimulation against the base of the dildo. Since the receiver controls more of the pace, it isn’t as easy to orgasm from as some of the earlier pegging sex positions on this list, but it does still provide some lovely sensations.

Maybe it’s just us, but I’ve found that this really tends to “unleash” my partner’s “ride the dildo and feel slutty” tendencies, too. Since he has complete control over the pacing, it’s a bit like a doggy style position, but since I’m nicely supported and sturdy, he can push back as roughly as he wants without moving my body. It also leaves my hands nicely available for gripping and guiding the action, too, if you want.

This pegging sex position can be especially fantastic if the strap on harness wearer has injuries or bodily limitations that might keep them from athletically participating in pegging. This still allows both partners to join their bodies together – but it puts most of the physical “work” on the part of the pegging bottom.

The pegging bottom still needs to be on their hands and knees, though, so if the bottom’s knees have injuries or concerns, this might not be a great position. However, if the bottom has injuries, you both can take this position as gently as you want, so it allows for a lot more control for both partners – and less “flailing” around. (Keep in mind that abdomen-supporting sex shapes like the Liberator Flip Ramp could help the receiving partner last a bit longer.)


Reverse Missionary Position

Image from: https://www.kinkly.com/definition/14542/reverse-missionary-position

Reverse Missionary Pegging Position

As I’ll note below, Missionary for pegging hasn’t gone particularly well for us. We find that my abdomen and body weight on his testicles squishes them in a not-fun way. This has been our workaround for that so we can enjoy face-to-face sex while keeping the balls safe from squishing.

This is just as easy to make happen as a regular Missionary sex position though. Just get in place, and instead of leaning forward on top of your bottom’s body, you just stay mostly upright. To help make the angle easier, you might find it easiest to place your bottom’s hips on top of a Liberator Wedge – or make them pull their knees up towards their head in order to angle the hips at an angle that makes it easier to get at the butthole.

This one can be workable for grinding for clitoral pleasure. It’s not as great as the first position on this list, but you can get a bit of grinding – especially at the innermost spot on every thrust.


The Spoon Position

Image from: https://www.kinkly.com/definition/473/the-spoon-position

The Spoon Pegging Position

This pegging sex position might take a bit of trial and error to get it right. It can be a bit difficult to make the angles match up – depending on the literal width of your hips compared to theirs. But if it works for your bodies, this beginner sex position for pegging lets you both enjoy some serious cuddles with very low athleticism.

As a tip, at least for me, I find that strapping on a longer dildo helps make this position much, much easier. I find that I lose a lot of my dildo‘s “length” between my thighs, their butt cheeks, and any space between us from my body’s size.

You might find that the dildo is too tall or too short (from the height of where their butthole is compared to where the dildo is hitting) when strapped into a hip strap on harness. Don’t forget about other strap on harness alternatives. A thigh strap on harness (which is what we usually use for this position) might be the perfect height. You can also make the bottom (or yourself) lay on top of a couple of pillows to add a lil’ bit of height that might make penetration easier.

I don’t generally orgasm from this position while wearing the harness as the movements are very shallow and gentle, but I also get to wrap my partner in some pretty big snuggles, kiss at their neck, and enjoy having them splayed out in front of me, so I consider this position big on the “other benefits” category. (Now that we’ve been using a thigh harness for this position, though, I just squish my Lora DiCarlo Baci between my thighs, and I generally orgasm just fine with this position)


The Kneeling Fox

Image from: https://www.kinkly.com/definition/8966/the-kneeling-fox

The Kneeling Fox Pegging Position

I love how this one takes height differentials entirely out of the equation. Simply sit down on your knees, have your pegging recipient kneel in front of you, and now they can slowly lower themselves onto the dildo.

This one made it into the “Hall of Fame” for best pegging positions for beginners because:

  • you don’t have to hold your own weight up awkwardly while someone slowly slides on
  • they’re not facing you, so you don’t have to worry about looking silly
  • it’s honestly pretty comfortable, all things considered
  • you can be as rough or as gentle as you want. If you’re still timid and want them to do all the work, just sit and enjoy yourself. At any point, if you want to get rough and in the actions, both of your hands are free to grip the hips, control the action, pull hair, whatever.
  • lots of great cuddle opportunities if you want those.
  • you can easily reach around and stroke them off (or finger them off) too which can put all of their aspects of pleasure in your hands

Grinding potential sorta exists here to get clitoral pleasure, but you really gotta get the strap-on harness and dildo in the right place – and you’ll probably need to spread your knees further to provide some upward motion instead of sitting still. Not a huge provider of clitoral stimulation here.

Big caution: As the penetrating partner, your knees will most definitely go numb at some point. If you’re not used to being on your knees – and you’re on hard flooring – and your partner is noticeably bigger than you – it’ll be faster. Don’t be afraid to mix up positions and speak up if your knees are screaming. I usually only get about 15 minutes in this one.


Beginner Pegging Sex Positions that DON’T Seem To Go Well

One of the most aggravating things, I’ve found, is that a lot of the “traditional” “first” sex positions don’t necessarily work with pegging. In fact, they seem to be entirely unfunctional for me – in the thousands of times I’ve pegged people and all of the partners I’ve had.

So, while you’re free to try these positions if you’d like (and hey! I highly recommend sexual experimentation for anyone!), here are some of the beginner pegging sex positions that NEVER work for me – and why they don’t work for me.

Missionary

Image from: https://www.kinkly.com/definition/75/the-missionary-sex-position

Missionary Sex Position

This one isn’t the worst, but it really depends on the bottom and their penile sensitivity. When I’ve tried this in the past, I’ve found that the testicles can get squished between my body and my bottom’s body – which can be more painful than fun for them. We usually will switch it up to the Reverse Missionary position – one of the best pegging positions above – if that face-to-face action is what I’m going for.


Doggy Style

Image from: https://www.kinkly.com/definition/71/doggy-style-sex

Doggy Style Sex Position

I’m, like, 90% sure this position was dreamed up with heterosexual, penis-in-vagina, sex in mind. I have never had a partner whose thigh-length perfectly matched up with my own. Every time I strap on a cock and kneel behind a willing bottom, I find that the dildo hits THEM about mid-thigh. Like, it’s hilariously short and away from the “target”.

I’ve had some luck getting the bottom to spread, spread, super-spread their thighs apart (which reduces their vertical height), but this is a level of flexibility a lot of people may not have, and it does get tiring on the thighs relatively quickly. We usually give up and just switch it into a Kneeling Fox position.

Maybe I just have tiny legs.


Standing at the Edge of the Bed

Image from: https://www.kinkly.com/definition/9458/the-desk-domination-position

The Desk Domination Position

I’ll give you this: if you find the right furniture height, this position is achievable. I can get the silicone dildo into the hole. What it DOESN’T provide is any sensation for me. I find this position so aggravating because it constantly pulls the dildo away from my body and provides zero sensation. At this point, I feel like I’m doing a ton of athletic work and getting sweaty for sensations that I could easily provide by just hand-holding the dildo.

I have been known to grump at pornography that shows Dommes primarily using this pegging sex position in all of their videos. There’s just no physical stimulation in it for the harness wearer for me – or any of my femdom friends I’ve talked to.

It does, however, film well, so at least there’s that – and probably why it’s selected so often.

It’s very possible you might enjoy the position if you’re not necessarily trying to get any clitoral grinding pleasure out of your pegging position.


Pegging Tips to Go With the Best Pegging Sex Positions

While you’re here, let me recommend a few tips to make your first pegging experiences go as smoothly as possible:

Don’t be afraid to experiment with pegging positions before the dildo and harness come out. Take the best pegging positions for a “trial run” with dry humping. Don’t actually intend to slide anything anywhere. Just get into these positions with your partner and try grinding against one another. Not only is this a fun tease that can build anticipation for what’s to come (“Let’s see how many different ways I could fuck you if I felt like putting on the harness. ;)” ), but it also lets you try out a wide range of angles and see how your bodies fit together. You might find that variance in height or body size might make some of the pegging sex positions you had in mind a poor fit. It’s much better to figure it out now before you have a naked partner in front of you.

Put on the dildo and harness in private long before you actually peg a partner. While this certainly isn’t required, I’ve found that a lot of people can “work out the kinks” if they’ve given their dildo and harness set a try long before they actually go about trying to slide that dildo into another human being. Putting the set on allows you to figure out how tight/loose you want it to be, and practicing humping a couch cushion or pillow lets you identify and practice the (probably not-often-used) muscles associated with humping something. I highly recommend this if you have the chance.

Ask your bottom to openly communicate with you. I’m not sure where some pegging bottoms got it in their heads that femdoms are born with an innate skill at pegging. I’m going to guess it’s probably because a lot of those same bottoms are used to years of penetrating things, and they don’t necessarily think much of it at this point. Ask your bottom to communicate openly with you. Is the dildo in? How close are you to the hole? Do they need you to go slower? Especially during initial insertion, this can be so helpful. I’d ask my bottom to tell me where the dildo is (“Go a little lower to get there…”), when the dildo finally popped inside (“Oh, there it is!”), and when they were ready to proceed (instead of me pushing forward at my own pace: “A little more please…”). Since I can’t see or feel the dildo, this helped me drastically. I highly recommend it. (And recommend the OhNuts, too, if you find you’re constantly going too deep without realizing it.)

Don’t be afraid to try different dildos. One of the cool things about strap on sex is that you can change your dildo – literally in seconds. USE THAT. If the dildo keeps falling out in a certain position, get a longer dildo. It’ll fall out less. If penetration feels too shallow, get a longer dildo. Solved. If you keep hitting internal spots that are too deep, get a shorter dildo – or toss some OhNuts on that dildo. Unlike bio-penis-in-vagina intercourse, your aftermarket attachments can swap out. Take advantage of that! You can strap on a freakin’ rocketship if you want. USE IT.


Resources to Make These Best Pegging Positions Even Better

You got the positions – now learn some other ways to make pegging even more awesome. Here’s some of the pegging help I’d recommend:

A plus-size woman in dark red panties is wearing a strap-on harness and dildo. Her partner is wearing a similar pair of panties and backed up against the dildo of the strap-on harness wearer. Image for Best Pegging Positions for Beginners.

Updated: September 2023, May 2023.

Mistress Kay
Mistress Kay
Sex toy reviewer, kink educator, and weirdo who is constantly staging pretty photos for sex toys.

Related Articles

Ultimate List of Online Service Submissive Activities (All Free!)

0
Maybe you've always played online - or maybe this is a first for you - but delving into the world of online domination, an...

Fantastic Shops!

Learn More!

How to Make Your Own BDSM Magnets

If you've met me, you know that sex and...

Everything You Need to Know about Saran Wrap Bondage

Bondage in saran wrap or bondage in cling wrap:...

Tips for Having Sex in the Water

Looking for tips for having sex in the water?...

Stay in touch!