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How to Peg Someone Complete Beginner Guide to Pegging

How to Peg Someone Complete Beginner Guide to Pegging

Editorial Team |

Generally speaking, 'pegging' is when a person wearing a strap-on penetrates another person anally. The urban term, however, usually refers to women who use strap-ons on men.

Exploring the world of harnesses and dildos can be fun; all you need is a partner willing to barge on the adventure with you. Between more intensive orgasms and simply the feeling of being naughty, many gay and straight couples frequently use pegging in their sexcapades.

If you're new to pegging but it is something you want to try, there are a few things to keep in mind beforehand. Keep reading to discover how to peg someone in the most pleasurable way possible!

Getting consent

Before you start picking strap-ons and thinking of sex positions, there's one major thing you need to consider and talk through - consent.

Pegging is an act between two consensual individuals that usually requires a lot of trust and vulnerability. Subsequently, by pegging your partner, you can increase the feeling of closeness and intimacy in and out of the bedroom.

However, getting consent sooner rather than later is crucial. As an act itself, pegging requires an open mind and your partner's desire to take a dildo in the booty.

So how do you start?

Talking is the journey's first step, and if you are interested in pegging your partner, exploring anal sex and anal play together is a good start. You can ask whether they enjoy it, do it on their own while pleasuring themselves, or if they'd be interested in trying it together. They will tell you their level of comfort with pegging, and you can proceed to discuss the possibility of you engaging in that act together.

It's essential to keep in mind that you should never pressure your partner and respect their decisions. People who haven't tried anal play or sex before may be reluctant to try it straight out of the bat. However, if they're willing to take things slow, you can always start with a butt plug and do some anal training or let them try a dildo on their own and take it from there.

This way, your partner will be familiar with the sensation and get more comfortable with having things in their butt. Additionally, you'll be giving them time to explore a new part of their body and discover a new way of pleasuring, which can only positively affect the pegging experience later.

Why men like pegging

Although not many men will admit it openly, a lot of them enjoy pegging and even more so have thought about trying it. But why is this subject still so taboo?

In mainstream culture, anal play or sex is still considered something gay people are into. However, the simple truth is that pegging, or being pegged, has nothing to do with sexuality and everything to do with curiosity.
Many straight men desire to be pegged because it's a different way of pleasuring that stimulates another part of your body and brings you incredibly potent orgasms. With the right dildo, you can easily reach a man's prostate gland and massage it, bringing on intense sensations and anal stimulation.

Many men also like the change in power dynamics that pegging brings into the relationship. If a man likes his partner to take the initiative and dominate him from time to time, then pegging can be a great way to tap into those kinks. Being penetrated, as opposed to being the one who's pegging someone else, is a way to break mainstream gender roles and feel pleasure on both ends.

For some men, pegging has been a new way to appreciate their sexual capabilities and give the whole act of penetrating a new dimension. Mainly, in straight relationships, men are always the ones giving it to the women, and being on the receiving end has opened their eyes to how much vulnerability it requires to let someone do that to you.

The sheer act of talking about pegging, and even more when doing it, can make your lover understand your needs in the bedroom and openly introduce other kin and fantasies into your erotic play.
Lastly, seeing a woman with a strap-on can be a big turn-on for those who don't allow themselves to get blinded by traditional gender roles. A lot of men have been intrigued by the image and, even more, have found it sexy for a woman to wear a dildo.

Which dildos are best for pegging?

The world of strap-ons and dildos is filled with various choices; all you have to do is found out your preferences and stick with the dildo that works best for you and your partner.

Although the dildo is the centerpiece of your act, there are a few things you need to keep in mind before you peg your partner. For starters, a good pegging kit has three things: a harness, a dildo, and lots of lube.

The harness is the strapping part of the strap-on and comes in numerous forms and materials. Whether you choose straps all over your thighs that look like boxers or a sexy thong harness, remember that the material should be comfortable as you might be wearing it for hours.

Additionally, you should make sure your dildo can fit in the harness. A harness with adjustable O-rings is the most practical thing you can choose, as it can be used with dildos of different sizes, depending on how to mood strikes you.

Once you've settled all that, it's time to pick your dildo. We'll go through a few key points you must remember when shopping for a pegging dildo with your partner or alone.

Our top picks for pegging dildos

Size does matter

If your man believes that size doesn't matter, pegging will surely open his eyes. When picking your pegging dildo, the size of it should be a shared decision.

First, you need to remember that once you put the dildo in the harness, you will lose a bit of its length. Besides, the only thing left to focus on is finding a length and girth that you can work with and that your partner will feel comfortable taking in.

As beginners, it's best to lower your appetites and start with a dildo that you both think it's small. Around 5 inches is probably a good starting point, while in terms of girth, you should go for 1 to 1.25 inches. Although the dimensions seem small, you can always choose a larger size in the future. Choosing something that would feel more comfortable on the first try will ease you into pegging and learning to love the process before putting pressure on the end goal - orgasm.

Only body-safe materials are allowed

Looking good is just as important as feeling good. When choosing the best dildo for pegging, you need to keep in mind that the materials of the dildo will play a significant role in the sensation you're giving to your partner.

Harness compatible dildos can be made from numerous materials such as glass, metal, PVC, etc.; however, choosing a body-safe is a must. Specifically, silicone dildos are the best for pegging due to their non-porous nature and durability. Moreover, silicone dildos are more flexible, somewhat squishy, and much easier to clean.

This will allow your partner to feel a robust anal sensation without being too hard during stretching.

Get The Texture Right

To give your partner a more authentic experience of what his penis might feel like, you might be prompted to look for a realistic dildo. However, opting for a smooth dildo as a beginner is a much better choice.

Since anal penetrations can easily irritate your partner's anus, it's better to keep it as simple as possible. Apart from the smoothness, you should also make sure the dildo has a relatively frictionless surface that can quickly enter small holes when paired with the right lube.

Dildos with ripples and ridges can bring extra pleasure to your partner, but you should wait and opt for them once you both gain a little pegging practice.

The right curve to hit the spot

Like the female's G-spot, men have a prostate gland. This is easily reached through pegging and can potentially bring powerful orgasms if your dildo has the right curve.

For direct prostate stimulation, your best bet is to choose a dildo with an upward curve. Depending on your sex position, you can give your partner a pleasurable prostate massage. The best part is that prostate orgasms don't usually involve ejaculations ad have nothing to do with the penis. So, you can give your man multiple orgasms while pegging him without the need to stop for a break.

Flared base to keep your dildo in place

The last thing you need to consider when purchasing your pegging dildo is picking the base. Since your dildo needs to stay put and not move while pegging your partner, it must be compatible with your harness.

The best choice is a flare-based dildo you can easily tuck into the O-ring. Additionally, even if you somehow manage to detach the dildo from the harness during anal play, the flared base ensures the toy won't remain stuck into your partner's anus.

Alternatives you should consider

If you want to save some time and quickly proceed to peg, you can always choose a strap-on with an attached dildo. No matter how rough or dynamic you get during pegging, the dildo will stay attached to your pelvis. This saves you the trouble of looking for compatible parts while ensuring maximum safety.

Another thing you might like to try is wearable or strapless dildos. While they can be tricky for beginners, wearable dildos ensure both partners will be pleasured. You can peg someone while also penetrating yourself and achieve orgasms simultaneously! And if you're feeling adventurous, you can always add vibrations to the mix with a vibrating dildo that arouses your partner's anus and stimulates your clit.

How to peg someone for the first time

After getting your partner's consent and picking the right dildo, the real fun can begin. We'll go through the steps on peg someone and what to remember through each step. When pegging your partner, try to enjoy the process and make them feel good rather than racing through it to make them orgasm. Remember that, as with conventional sex, solely focusing on the goal can hurt the experience.

Get comfortable

Before you can pleasure your partner, you need to ensure you're fully in sync with the new part of your body. You can look at it, touch it, or even wear it randomly around the house to get the hang of its movements.

The same goes for your partner. Before starting the sexual act, it's best to let your partner get used to the idea of you with a penis. You can allow them to use it beforehand and see how it feels, or at least leave them time to look at it and feel it out. This brings us to the next point.

Foreplay: the make or break point

Looking at and touching the dildo is just a start. To have a complete and pleasurable experience, avoid putting on the dildo right before pegging your partner. Instead, wear it from the start and use it in your foreplay.

While some open-minded men will like to play with it, hold it or suck it, others won't want to pay it that much attention. However, that doesn't mean you shouldn't explore your partner's anus before putting in your dildo.

To relax the spot and give them a taste of the feeling, you can start slowly massaging around the anus before putting in a finger. You can feel them out and add as many fingers as you see fit.

Lube is your best friend

Skin frictions and irritations are the last things you desire when pegging your partner. To make sure they're comfortable and feel the least amount of pain possible from the start, you need to come prepared with lots of lube.

Keep in mind that there's no such thing as too much lube. You can put it on your dildo and your partner's anus, and for extra ease during penetration, you can also use lubricated condoms. However, ensure your lube is compatible with the materials of your dildo. For example, if you've headed our advice and purchased a silicone dildo, it's best to pair it with a water-based lube for the most slippery feeling.

Using silicone-based lubricant with a silicone toy can degrade and lose its texture over time. This will make the dildo unsafe for body use and can potentially harm your partner.

Take it slow & communicate at all times

Once both of you are aroused, and your dildo is lubed-up, you can move on to pegging your man. Put in the dildo slowly and gradually while checking in with your partner about their pain level and comfort.

Once your partner feels comfortable with the size, you can increase the rhythm of your penetration and bring them the tingling sensation of prostate massage. Don't rush the process; give your partner time to adjust to the girth and length. Re-apply lube as much as you want to minimize friction.

You can switch positions and take breaks depending on the situation. The most important thing is to communicate about your state and listen to your partner, avoiding any accidents and unnecessary pain.

Tips for using a pegging strap-on

Safety is just as important as pleasure when pegging your partner. Apart from choosing a dildo from body-safe materials and using lots of lube, there are a few things to remember before entering the bedroom. Here are a few extra tips:

Mind the fit of the harness

If you opt for a strap-on dildo for pegging, you need to pay attention how your harness first. While choosing a harness with fewer straps might look prettier, it can be less safe. Namely, if your harness doesn't fit your body properly, it will reduce your control over the dildo and might cause unexpected injuries during sex.

The same goes for learning to put on your harness correctly. Thrusting into your partner is a dynamic activity, and you'll want your dildo to be strapped as tight as possible to your body while also feeling comfortable.

Anal training before penetration

While using a few fingers to relax the anus before pegging might be enough for some, you can also suggest anal training to your partner. They can wear a butt plug beforehand or try pleasuring themselves with a small prostate dildo before letting you do the same to them. After they've gotten comfortable or feel stretched enough, you can peg them.

Keep it fresh and clean

While pegging sounds fun, it involves playing with a part of our body that excretes waste. This goes both for the dildo and your partner's body. To avoid spreading bacteria or infections, you must ensure everything is clean.

As the person being pegged, they must have a bowel movement beforehand and thoroughly clean the area. As the pegger, you should ensure the dildo you're using has been washed and disinfected correctly. Cleaning the toy immediately afterward is a must so you can safely use it again. For bigger safety and less demanding aftercare, you can also use condoms.

Best Positions

Communication is necessary to find the proper position for pegging. However, a few positions are generally practiced and favored for this sex act.

  • Doggy style: Most couples prefer doggy style for their first try as it feels most familiar. Have your partner sit down on all fours and stand behind them. You can also do this position standing up; however, if you're a different height, you might need to wear high heels.
  • Spooning: Another popular choice is the side-by-side pose. Your partner will lay on their side while you peg them from behind. This position is intimate and will allow you to spoon your partner during sex.
  • Missionary: If you want to explore the benefits of the missionary pose, have your partner lay on their back with their legs in the air. This is a great position to stimulate the prostate gland while also sharing the intimacy of eye contact during sex. Additionally, you can lay over your partner and give yourself extra support with your arms while trusting.
  • Cowboy: For beginners who need to get used to the necessary hip movements, sitting on top while the partner lays on their stomach may be the most precise position for pegging. Your partner can relax underneath while you peg them and get a nice view as a bonus.
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Final thoughts

If you're hungry for new sexual experiences, pegging should be on your “to-do” list. It allows you to experience what having a penis would feel like and give your partner a quality pounding.

The orgasms can be extra powerful, and the whole sex act is entertaining. Both you and your partner get to explore a new side of yourself and indulge in different energies and power plays.

Ultimately, the pegging experience is a journey of exploration. You get a better insight into what you like and don't like while sharing incredible intimacy and newfound trust with your partner.

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