Complete Guide To Pegging

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What is pegging? Pegging, also referred to as strap-on sex, is where a female partner uses a strap-on harness & dildo to penetrate her (often) male partner.

Pegging is making its way into the mainstream of sexuality, even being referenced in big-budget Hollywood movies like Deadpool. If you’ve found this article, then there’s a reasonable chance that like Wade (or Wade’s partner) you’re thinking about pegging too. Don’t worry – we’ve got you covered.

In this guide you’ll learn about:

Broaching the subject

Unless you both meet in the hallway and simultaneously say “how about we try pegging!” – then one person is going to have to go first in terms of bringing up the subject trying pegging in your relationship.

You may be lucky in that you have an open-minded partner with whom there is nothing you wouldn’t discuss – in that case – what are you waiting for? Go ask, we’ll wait.

Realistically for many couples something like pegging may be considered a little taboo, so here are a few tips on how to bring up your interest in pegging with your significant other.

If it’s her asking him

This one really depends on the kind of guy he is.

If he’s more of a modern metrosexual leaning chap then you might be able to bring up the idea straight off, however if he’s more of a “man’s man”, and you are concerned about his reaction – then you might want to consider bringing butt-play into your relationship more slowly, perhaps suggesting a finger or a butt-plug first, then moving on to suggesting pegging once these ideas have been (hopefully) well received.

Even a stray finger during your regular love-making can do the first bit of the talking for you.

Plus you never know – he could be reading this guide as well…

If it’s him asking her

Much as with the previous answer, this again depends on the kind of woman she is. A lot of guys worry that by asking for some butt-fun their partner may see them as less of a man. You know your partner better than we do, but hopefully you’ve chosen her because she isn’t like that.

Still if you have concerns, there is some mileage to bringing it up in a joking sense, or as an “oh no, alright then” to asking her for anal sex and being responded to with an “only if I can do you too”.

The one-step-at-a-time method can also be useful here, sound her out on putting a finger or a butt-plug in your butt, and take things from there.

Discussing what you’re looking for

Ok so your partner has agreed, awesome, now how’s this thing going to play out?

People have different ideas about what they’re looking to get from a pegging experience. For some it’s the physical pleasure of having something in their butt, for others it’s the role-reversal aspect, or most often – a mixture of the two.

Elements of domination can also be added into the mix.

This is where communication is key, you’ve already opened up the channels by broaching the subject – so now let’s keep those channels open by discussing what we’d both like out of it. With a single act like pegging it’s going to be quite unlikely you will be after completely different things!

Buying a harness / dildo

Firstly, as pegging takes two, it makes sense to shop for the dildo & harness together – ensuring you will both be happy with your new equipment.

Secondly, whilst there are many “beginners” kits out there, these can made to a price-point and can deliver disappointing results. We’d certainly always recommend against kits where the dildo and harness come as one and cannot be seperated, as these just mean you have to purchase everything again if either aspect isn’t doing it for you.

The harness

The key to a good strap-on experience is for the wearer to be able to control the dildo as if it was part of her. This means it needs to be securely strapped on. Some of the cheaper / “beginner” kits have loose, elastic straps holding the dildo in place which means when she tries to pull back – the dildo will remain in place rather than come back with her.

This is just going to lead to at best having to buy another harness, and at worst a disappointing experience not to be repeated.

So we’d advise to purchase a harness that is reasonably secure, we’ve covered some great choices in our strap-on harness reviews.

The dildo

If the receiving partner is new to anal play then it makes sense to start small dildo-wise and move up from there.

If the smaller dildo isn’t doing it for you then you can always buy a bigger one, but if your first time pegging involved attempting to insert something that’s too big for you then you’re gonna have a bad time.

Dildos can get quite expensive when looking at some of the ‘realistic’ end of the market, where they are made with advanced material combinations to give them a life-like feel. We’d recommend trying sizes out with cheaper dildos, then making your purchase of a more expensive model once you’ve decided what size is right for you.

You can read more in our stap-on dildo reviews.

Don’t start strapless

Strapless dildos can be awesome, but they generally aren’t for beginners.

A lady needs to develop her technique and become confident being the giver, and this is extremely difficult to do whilst having to manage the extra difficulty of successfully keeping a strapless dildo in place during a pegging session.

Read our Strapless vs Harness Strap-ons guide for more.

Wearing the harness

With most harnesses it’s reasonably obvious how they go on, but our top tip is to keep them reasonably tight.

This enables the wearer to have maximum control over their ‘equipment’ and leads to a more pleasurable experience for both.

The wearer might also want to practice how they are going to thrust beforehand. Whilst amusing to watch, this does prepare them for a type of movement they may well have not experienced before. Some of those muscles might be getting a bit of a workout the likes of which they’ve never seen, so some preperation can be beneficial just so you know what to expect and how long you think you can last in full-on thrust mode.

Getting things started

We’ve got this far friends, congratulations. The act is nearly upon us, how do we get things rolling? Top-tip – don’t just stick it in.

Foreplay

Just as you would with regular penetrative sex, some foreplay can get you both in the mood and help you relax.

The foreplay doesn’t have to involve the dilo, or it can, up to you. Our advice for newbies might be to save the dildo for the “main event” on your first occasion, but that depends on you.

Lube

There are no two ways about it, lube is most definitely your friend here.

Invest in a quality lube – we’ve got some great recommendations in our lube reviews – and you won’t regret it.

We’d recommend having a cloth or towel on hand to wipe the lube off your hands after applying.

Take it easy

This one is for the wearer – whilst having the dildo dangling between your legs might make you feel like you now have a penis, just remember you can’t (unfortunately) feel anything through it. When you can’t feel – start off slow. Talk to your partner, they’ll be able to let you know how you’re getting along.

With anything anal related it’s often said that “the first inch is the worst” – bear that in mind that it might hurt a little getting in, but once in and she’s started moving gently in and out, the feelings should become much more pleasureable. Then you can pick up the pace should you so wish.

Pegging Positions

For both of you you’re going to be on the other side of the looking-glass for this one! Here are some of our top positions to try.

Missionary

This is a great position as it allows the reciever to really experience the role-reveral aspect of pegging, having her on top of you taking the lead can be quite exciting.

For beginners – she’ll likely have a bit of a hard time trying to find your butt hole in this position, so we’d recommend trying a sex wedge to raise the receiver up a little to make things easier the first few times.

Doggy

A classic pegging position.

Doggystyle makes it easy for her to find where she needs to put it, and gives her the opportunity to grab the receiver’s hips while thrusting, even (hopefully) well-earned reach-around.

Just to bear in mind – if the wearer is shorter than the receiver – the receiver might have to squat down somewhat, or try it with the receiver on the bed and the wearer standing on the floor (depending on the height of your bed of course).

Cowboy

This is more of an advanced position – and is what it sounds like – the wearer lies down whist the receiver riders the dildo. Just as with other positions taxing muscles that the wearer might not have used before, this could be the case here for the receiver.

As with all these positions – practice makes perfect – if your first time isn’t like the pornos you definitely haven’t watched already – then don’t worry, think of all the fun you’ll have getting it right. Communication also really helps when getting these positions perfect, keep talking – let him / her know what feels good.

Again to remember that the wearer won’t have any sensitivity in the dildo, so you might have to let her know that she’s on course when it comes to putting it inside you!

Make it good for her

As we just mentioned, there’s no physical sensation for the wearer – so is pegging just a one-sided deal? Absolutely not.

Pegging gives the wearer the opportunity to take the lead & be the one in charge – for some women, just that thought is enough to get them off. That combined with the gyrations of the harness could be enough to push her over the edge.

However there’s a large chance that she’ll need some extra stimulation to get her off. So you have a few choices. She can get off first, or she can get off after – some communication and experimentation here can help you choose which is best for you.

Or – you can try and get off together (with a little help). Many harnesses come with small pouches in which you can place a bullet vibrator (even if they don’t the tension from the harness may be enough to hold on in place anyway – although if using a vibrator is important to you, it might be an idea to make sure you harness has this).

Strap-on & oral

Strap-ons aren’t just for anal. A fun piece of role-reversal can include the receiver giving oral sex to the strap-on. This is another different dynamic than either of you may be used to, and gives you both a unique experience and a great, unique view for her.

If you want to take things a step further, rubbing some flavoured lube on the strap-on can give a sense of achievement – “i’m going to put this in you once you’ve licked it clean” – for example.

Pegging as part of female domination (femdom)

The pegging we’ve discussed here would be mostly classed as ‘vanilla’ pegging, as despite the reversal aspect there’s no BDSM style power-exchange. This doesn’t have to be the case of course, and we’ll be covering pegging in our upcoming female domination guide.

Complete Guide to Anal Sex & Butt-Play

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