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Man wondering about pegging for beginners

Ultimate Guide to Pegging for Beginners: Top Tips, Positions, Toys, and More

Picture of Lisa Welsh
Lisa Welsh

Podcaster
Sexual Health & Pleasure Educator
Media Liaison for the World Association for Sexual Health

Are you interested in exploring the exciting world of pegging? 

While pegging holds loads of benefits for you and your partner, including, but not limited to, more intimacy and mind-blowing pleasure, it can be pretty intimidating — especially if you haven’t done it before. 

Don’t fret! In this article, I’ll provide you with everything you need to know about pegging for beginners, including top tips, hygiene, sex toys and tools, and so much more. 

Understanding the terminology

Before we dive in, let’s clarify the language I’ll use throughout this article. Pegging refers to using a strap-on dildo for anal penetration. While gender and orientation aren’t fixed, for simplicity, I’ll refer to participants as a man and a woman throughout the post. 

However, please note that men can refer to individuals receiving anal penetration (with or without a penis), and women can include anyone who gives anal penetration with a strap-on dildo, regardless of gender or sexual orientation.

Why would you want to explore pegging? 

First, let’s understand why someone might be interested in pegging:

  1. Pegging can offer intense pleasure for men due to prostate stimulation. 
  1. It can empower women to give pleasure and explore their partner’s desires. Physical sensations, such as grinding against the dildo’s base, can also contribute to their pleasure. (We’ll discuss wearable and vibrating strap-on dildos later).
  1. Gives you a chance to navigate power dynamics. Pegging involves a significant power dynamic, particularly when a heterosexual, cisgender man experiences anal penetration for the first time. Thus, it can transform your sex life by offering valuable insights into each other’s perspectives.

Top pegging tips for beginners (to get you and your partner started… the right way😉) 

Below is a list of some of my top tips you and your partner can follow if you’re new to pegging. 

1. Choose the right tools

For any toy that will go into the butt, you want to look for body-safe materials and a flared base. The flared base prevents the toy from getting lost in the anus (because nobody wants to take that trip to the medical room). 

But apart from that, the world is your pegging oyster. You can choose the sizes, shape, and squishiness that feels best to you and your partner.

Start with something as small as a finger or two fingers up to relatively large and realistic-looking phallic dildos. And choose the shape that most appeals to you. Maybe you want to go for something straight or maybe something curved. A curved dildo could be great for accessing the P-spot and giving it the direct stimulation it likes.

And what about the material? You can get firm dildos or something more squashy, pliable and movable, like the Strap-On-Me Bendable Didlo

alt: Image of a strap-on dildo

So, what are your preferences? I always recommend starting smaller, starting with something squishier, and gradually building your way up. But the choice is yours, providing that it’s body-safe. So, go for it!

Now, what about the harness? You can get different kinds of harnesses. Some look like underwear that you’ll just pull on the knickers, and you can get a dildo that attaches to that wearable knicker harness. 

You can get straps, or you can get a wearable dildo that is placed inside the vagina (some of them even vibrating🤩). 

I highly recommend shopping around for these together so you can build up that excitement and anticipation and talk about your expectations. Nearly every online sex toy shop offers discreet packaging, so you don’t have to worry; nobody will know what you’ve ordered. 

2. Spend time on hygiene and preparation

My next tip on pegging the right way is to have a clean butthole. This is going to help everybody feel more comfortable. If you’re concerned that there’ll be poo everywhere, it can make everybody feel uneasy. 

However, poo could happen because we are playing with the butt. So you have to be aware that this might happen anytime you’re doing any kind of butt play. But there are things you can do to reduce the likelihood of poo being present. 

  • You can be mindful of what you eat on the day of the pegging session (don’t have anything too oily or fatty).
  • Use the bathroom, take a shower, and use a finger to clean your anus beforehand.
  • Use a douche that you fill with warm soapy water and release into the butt several times until you feel clean. 

alt: Image of an anal douche

(Image Source)

Furthermore, here are a few precautions you need to take to ensure a hygienic and safe pegging experience:

  • Ensure that you and your partner have clean hands and trimmed nails to minimise the risk of injury.
  • Remember to clean your toys with a good toy cleaner before and after use, following the manufacturer’s instructions. 
  • If you’re using condoms with the dildo, change them between partners to prevent the spread of bacteria. 

3. Lubricate… a lot

Lube is so important. 

Depending on your preferences, you can choose silicone or water-based lube. Discover the differences between water and silicone-based lube here

I prefer silicone when it comes to the back door because it lasts longer. So, if you’re choosing water-based, that’s fine, but be prepared to reapply that lube more often and be ready to use a lot more lube than you think. 

Lube is vital to reduce friction and pain and to make the experience far more pleasurable. Apply it to the dildo, to the butt, and use a lube applicator to squeeze some lube inside the anus in preparation for butt play.

alt: Image of lubricant being poured onto a banana

(Image Source)

4. Take it slow

Start by exploring other kinds of butt play. Maybe play with both butts so that everybody knows how this feels because that helps both parties understand what it takes to relax and to be penetrated anally. 

Suppose you’ve already tried putting a finger in each other’s butts, prostate massages, and anal toys such as butt plugs or anal beads. So now you’re at the point where you’ve decided, yes, pegging is happening today. 

How do you take it slow? 

Start by preparing the environment: 

  • Is it warm and comfortable with beautiful music? 
  • Does it smell good? 
  • Are there pretty things to see? 
  • Have you got snacks and treats and privacy? 

Both you and your partner need to feel as comfortable as possible. 

Foreplay

Then you’re going to warm up with lots and lots of foreplay, incorporating the entire body and erogenous areas. Don’t forget the penis, the nipples – and of course kissing, hugging, and making out — whatever feels good. 

You don’t have to go straight to the main act. This is one of the reasons why pegging is so great because it will teach the man that penetration isn’t something you necessarily want to rush into, whether you’re penetrating an anus or a vagina.

Furthermore, foreplay will help the man to relax, breathe deeply, and release any tension they may be feeling. This will allow the anus to relax. 

From there, the woman can massage his anus by inserting a finger or two and getting him to a point where he’s comfortable with the feeling. You’re going to have so much lube, remember, and you’re going to slowly allow that sphincter to relax. It almost welcomes you in after a while. 

You might not be aware that after entering the initial sphincter, there is also an inner sphincter, a little bit deeper. So the woman needs patience once her finger/s has entered this far in.

alt: Illustration of male sphincter

(Image Source)

To get past this sphincter, the woman needs to maintain that pressure and stimulate with a little bit of circular massage — all while encouraging her partner to relax so that muscle can relax too. This isn’t a voluntary relaxation. It happens when the body feels safe and calm.

Remember to communicate throughout this entire process, asking, “How is that for you?” or “How does that feel?”.

You’re going to be reading their body language as well. Notice whether they’re tensing up or moving away from you. 

It’s vital to keep the arousal high so that this continues to be a satisfying and loving experience.

Best positions to do pegging the right way

Contrary to popular belief, pegging can be a gentle, affectionate, and passionate experience. It doesn’t have to be super rough. I’ve often seen it portrayed in porn as quite a wild activity, but it doesn’t have to be like that at all. So keep this in mind as I talk about these positions.

Also note that the positions you choose will likely differ from other couples since there are several factors to consider, such as height differences, mobility differences, etc. 

1. 69 position

You might be surprised because this is generally an oral sex position, but it can be done where the man is lying down, and the woman is lying the other way over him. So oral sex is happening both ways. 

Now the woman will have her man’s penis in her hand or mouth. From this position, she can reach over and stimulate the anus with her fingers or a sex toy. 

This is an excellent warm-up move. 

2. Missionary 

Missionary with the man on his back underneath and his legs up in the air. This means he is lying almost folded in half, and then the woman is on her knees between his legs, and she can either hold his ankles or his feet, or he can hold his own feet, and she can hold his penis. You can mix that up.

alt: Illustration of missionary pegging position

(Image Source)

This then allows her to penetrate his anus with the dildo very slowly and gently while maintaining eye contact and being close physically to him. In this position, she can control the penetration’s depth and pace, ensuring it’s comfortable and pleasurable for both partners. 

It also allows easy access to stimulate his other erogenous zones, such as his penis, testicles, or perineum.

3. Doggy style

The man is on all fours in this position while the woman kneels behind him. 

She can use a strap-on dildo to penetrate him from behind. This position provides deep penetration and gives the woman a good view and control over the movements. It can also be a more dominant position if that’s something both partners enjoy.

4. Seated position

The man sits on a chair, or the edge of the bed, with his legs spread apart, and the woman straddles him. She can then control the penetration and rhythm while using a strap-on. 

This position allows for face-to-face intimacy and eye contact and can be adjusted for comfort and pleasure.

5. Spooning position

Spooning involves the man lying on his side with his knees slightly bent and the woman lying behind him, on her side. 

This pegging position allows for intimate closeness and a more relaxed and gentle experience. The woman can use a strap-on or her fingers to penetrate the man from this position, and they can both adjust the angle and depth of penetration as desired.

alt: Illustration of spooning pegging position

(Image Source)

6. Cowgirl position

In this pegging position, the man lies on his back while the woman straddles him, facing towards him. She can then guide the dildo into his anus and control the movements and depth of penetration. This position allows the man to relax and enjoy the sensations while the woman takes the lead.

7. Reverse cowgirl

The reverse cowgirl position is similar to the cowgirl position, but the woman faces away from the man. 

It provides a different angle of penetration and can be stimulating for both partners. The woman can lean back and use her hands for support or reach around to stimulate the man’s genitals while penetrating him.

8. Standing position

This pegging position involves the man standing and leaning against a wall or a sturdy surface while the woman stands behind him and penetrates him with a strap-on. It allows for a different level of control and can be exciting for both partners.

Ready to explore the exciting world of pegging? 

Communication and consent are vital to any sexual activity, including pegging. Talking openly about desires, boundaries, and comfort levels is essential before engaging in this exciting endeavour. 

Each couple may have their own preferences and variations to these positions, so feel free to explore and experiment to find what works best for you and your partner.

Lastly, always prioritise safety and hygiene. Be sure to use plenty of lube, choose appropriate-sized toys, and clean them thoroughly before and after use. 

Enjoy the experience, have fun, and continue to build trust and intimacy with your partner!

And if you want to take your learning to the next level, check out Beducated for a wealth of practical resources to get you started with butt play.

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