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Sex

A Gal’s Guide to Pleasurable Pegging


Flipping the script can feel amazing for both of you

There aren’t a lot of women out there writing how-to articles about the art of pegging. We’ll call it an art, as it can be an insanely pleasurable encounter for all involved if you take it slow at first and communicate clearly with your partner throughout.

To put it simply, pegging is when someone without a penis straps on a dildo and anally penetrates their partner.

I’ve written a story about how pegging can be sexually empowering for a woman, and it’s drawn a lot of questions from readers.

Being able to talk openly and honestly about sex is what I’m about, so I’m glad there are more dialogues happening — especially when it comes to things we want to explore but maybe are a little bit nervous about.

Pegging is definitely one of those more adventurous activities people tend to be nervous to try for the first time. It can be taboo and mysterious — a type of uncharted territory where gender roles are swapped.

The woman gets to experience what it’s like to become the penetrative partner, and the man experiences what it’s like to be on the receiving end — which can lead to a stronger orgasm for him thanks to the prostate stimulation that pegging allows.

It’s a beautiful head trip for a woman like me that can bring immense pleasure in and of itself — mentally and psychologically.

For you vulva owners out there: have you ever tried penetrating your partner with a strap-on? Have you ever taken control and dominated his body, hovering over him and giving him pleasure with every thrust?

Flipping the script in this way is something I highly recommend — just to get a sense of how the other side feels.

But pegging is more than just a way of connecting mentally. It can bring a ton of physical pleasure for the wearer of the strap-on as well.

I’ve had an intense orgasm while pegging my partner, which made it all the more enjoyable for both of us.

Pleasurable pegging for her

My male partner puts pegging at the top of his list of pleasurable activities. I’m pretty sure he’d be up for it any time I offer, and it’s something he’d like to do more of.

He’s shared with me that if he strokes himself to completion while being pegged, he experiences an incredibly intense orgasm.

But it’s also possible to orgasm while doing the pegging.

There are a few ways to achieve this.

1. Use a small vibrator that you can place between the strap-on and your clit.

When you’re first starting out and aren’t sure if you’ll both enjoy pegging, try this simple and economically friendly method before investing a big sum of money into a fancy vibrating harness or a hands-free clit stimulator/strap-on combo.

A bullet toy or mini-vibrator fits snugly between the base of the dildo and your clit. When I did this, I got some major stimulation with every stroke. And when I was close to the edge, I stayed still inside him while letting the orgasm flood through me. It was an unforgettable experience for both of us.

Although the bullet worked fine for me with a basic harness, there are also versions out there that have a nice little pocket for just this purpose.

2. Certain positions and angles

The position, angle, and pace all affect the way the trappings of the strap-on and harness rub against you. For example, lying full-length on your partner’s back while thrusting slowly into his ass is a good way to get some clitoral stimulation.

Doggie style can also work well, as you can easily change the pace and the angle at which you enter him.

Or, if he’s on his back, it can be easier to incorporate more of a circular grinding motion, ensuring your clit is getting some lovely friction.

Experiment with angles, positions, and rhythms that work well for you. And remember to check in with your partner often to make sure everything is feeling good.

3. Double-ended

There are so many fun double dildo devices out there just waiting to be explored. Every woman’s vagina is different, so it can be a bit of trial and error to find the shape and size that works best for you without the device slipping out constantly.

A lot of the double-ended dildos vibrate inside you for excellent G-spot stimulation. Some have a clitoral vibrator on the outside that loves on you with every stroke. There are even harnesses that come with a butt plug attachment — for the woman who loves a little booty stimulation while she goes to town on her partner.

Take a walk on the wild side and pick something that appeals to your pleasure zones. It can be a bit hit or miss, so don’t give up right away if something ends up not working out.

4. Foreplay

Coming before you start pegging (or getting very close to it) is a great way to keep the pleasure going for you as you simultaneously give pleasure to your partner. This past weekend, he generously went down on me until I came—and this was before we even touched the strap-on.

Then, he helped me into the device and tightened the harness until it was a perfect fit. It’s easier if your partner helps with this part. Plus, getting rigged up in and of itself can be a major turn-on. And the stunning visual can do a whole lot for all parties involved.

Enhance your sex life — and strengthen your bond

Many of us get pleasure simply by giving it. Making our partner all hot and bothered can, in turn, get us aroused and ready to go.

If you’re wondering how to get your partner interested in trying pegging (whether you’re the one pegging or being pegged), start with a simple conversation. Maybe you can send them an article on the topic (such as this one!), listen to a podcast, or watch a YouTube video together that covers the basic mechanics of Pegging 101, like this fabulous and informative video from Sexplanations.

Go slow, use more lube than you think you need, and constantly check-in. If you’re the one wearing the strap-on, remember that’s it’s not actually a part of your body and you can’t feel what you’re doing when you’re inside your partner. This is where talking is crucial for safety.

Start slow and learn what your partner likes by having them guide you. Do they want you to go deeper, faster, or slower? Keep the communication going.

My partner happens to like an intense and fast pegging, doggie style, as he strokes himself. It’s one of the most challenging workouts I’ve ever experienced. Because fucking someone is really a lot of work — and it’s toning a set of muscles you’ve never used before!

Be safe and have fun while pegging. It can improve your relationship dynamic, strengthen your communication skills, and enhance your sex life.

You can find more of my work at medium.com/@holly.bradshaw


If you like what you read, you can join my mail list, and I’ll send updates from time to time on my latest creations.

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