How To Peg Someone For The First Time (And Why It Should Be On Your Sex Bucket List!)

If you are a vagina-owner who has been wondering how to peg someone for the first time, know this: pegging is more than just about being extremely pleasurable and orgasmic. Pegging is also an easy way to “reverse” the standard power roles in a cishet relationship and get to know each other on a deeper level.

Note: “cishet” is short for cisgender (and) heterosexual.

What is pegging?

Pegging refers to when a woman performs anal sex on a man, using a strap-on dildo. It was a term crafted in a contest by columnist Dan Savage and is all the rage right now, but like with any “butt stuff” it can be fraught with stigma and misunderstanding.

Unlike other sex stuff, pegging and other anal sex stuff might be more challenging to bring up to a cishet male partner. In a heteronormative world’s understanding of sex and how sex is seen as something men do or give to women, having a cishet man “receive” might be misunderstood as being feminine.

how to peg someone

In fact, a lot of women internalise this as well. The idea of bending over their male partner and giving it to them anally might feel uncomfortable – sadly, anal pleasure for men is still on the receiving end of a lot of homophobic judgment. However, if you or your cishet male partner is ready to learn how to peg someone for the first time, then read on for our guide on how to peg someone as a beginner!

Related: Strap-On Slipping Out While Pegging? Here’s Our Advice On Pegging For Plus Size Women

Why does pegging feel good?

For men and people assigned male at birth, being penetrated in the butt feels amazing because there are a lot of nerve endings in the anus or rectum. Pegging also targets the the male G-spot which is the prostate gland, which feels usually so much more different than other orgasms.

Pegging is also pleasurable for the pegger, because it plays with and switches the traditional gender roles of what men and women should be or do during sex. Pegging can be rough with a dominance play, but it can also be a loving and sensual act. It can be empowering as well as physically stimulating.

Many people also agree that pegging takes the health of your relationship on to another level, due to the deepening of trust between you and the other person. This is a vulnerable sexual act that is quite unlike the others.

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How to peg someone (Our best pegging tips!)

1. Talk it out first

No one likes surprise butt stuff, so if you want to peg your partner or they want to be pegged by you, make sure there is in-depth communication about pegging first. Share about what you are hoping to experience with them, and what about pegging turns you on. Make this experience about “we”, and less about “I”, so how it could be fun for both of you.

As mentioned, pegging can still be somewhat of a taboo for some cishet men. Even if they might be open to pegging or have thought about it at some point, they might not as open to talk about their desires in exploring anal sex. Having non-judgmental communication with your male partner can help to establish an understanding about one’s desires and kinks without any judgement.

If your male partner needs more time to warm up to the idea of pegging, you both can first explore dirty talking or sexting pegging scenarios. Being able to talk about pegging is a first good step towards doing it.

Related: What is exhibitionism kink? A deep dive into the sexual kink of consensual exhibitionism

2. Shop for a pegging strap-on dildo together

What you will need is a dildo, a strap-on harness, and lube. If he is new to pegging, bigger is not better so start with a smaller dildo. Dildo that are 5.5 inches in length and about 1.25 inch in diameter are good for beginners to anal sex.

Make sure the dildo is made of body-safe silicone and is phthalate-free, and has a smooth texture to allow for a simpler starting point. Here are some of the best dildos for pegging when you are new to learning how to peg someone:

Related: 5 Best Strap Ons For Pegging As A Couple – Reviewed

Tantus Silk Dildo

The Tantus Silk dildo is the perfect choice for a first pegging dildo. It is small enough not to push it too hard when learning how to peg someone for the first time, and it is available in three sizes for when it is time to go larger. This dildo is made from Tantus’ own unique formula of 100% Ultra-Premium Silicone, and is also easy to clean after use.

4″ Pegging Strap-On by TooTimid

This dildo with harness by TooTimid is the perfect beginners strap-on for pegging! It comes with a silicone dildo that is firm yet flexible, with a slight curve that provides amazing stimulation to the prostate. When ready for a size up, the adjustable harness is also compatible with other dildos.

Want to feel extra pleasure as the pegger? Add a vibrating bullet inside the pocket on the inside of the harness. The dildo is also waterproof, so feel free to have fun in the shower.

Tantus Strapless Strap-on Slim

The Tantus Strapless Strap-on Slim is designed to give skin-on-skin contact, perfect if you are looking for a more intimate connection with your partner without breaking the continuity of action to adjust straps and buckles. Wear the strapless strap-on by using your internal muscles to hold it in place with the bulb.

Rami Harness Strap On Dildo by Honey Play Box

If you are looking for a more realistic flesh looking strap-on dildo, then the Rami Harness Strap On Dildo by Honey Play Box is for you. The dildo is made from body safe, smooth and strechable silicone for easy slid in. It is also waterproof, so take it out for pleasure in the bath or shower.

3. Put a condom on the dildo

Any time there is butt play happening, you want to make sure that no-cross contamination happens. Putting a condom on the dildo before pegging makes the cleanup faster, plus it also help with more lubrication.

4. Use lots of lube!

Unlike our vagina, the anus is not self-lubricating and therefore needs lots and lots of lube before penetration. Foreplay is also important when it comes to pegging, as the anal sphincter needs to relax in order to make it easier to enter the back door without tissue tears.

pjur-backdoor-anal-lube-tantus

The best lube to use for pegging is lube made specifically for anal sex. Make sure to use water-based lube for silicone toys. We like the Pjur Backdoor Anal Glide water-based lube as it is smooth, long-lasting and compatible with all condoms and sex toys.

Depending on what he likes for setting the mood, you can give him a sensual massage as foreplay or get dirty with dirty talking.

5. Choose the right pegging position

For anal beginners, start with the missionary position where you have him lie on his back, or spoon him from behind. These two positions are easier to pull off anally than doggy-style if you have no experience with pegging.

6. Enter slow (like, really slow)

Unless your partner is already experienced with anal sex, take things slow if he or both of you are new to pegging. Don’t go from zero to dildo. Instead, play with inserting a finger (then two) and also explore using a butt plug.

Related: How to use a butt plug for the first time!

If you are fingering, it is a good sign once you start to feel the anal tissue softening because it shows that your partner is more relaxed and ready for deeper penetration.

For the dildo, make sure it is always facing away from his spine and towards the belly button for prostate stimulation.

7. Aftercare matters too

Engage in post-pegging aftercare and talk through what worked and what didn’t – the good, the bad, and messy. You can do this by just holding each other and checking in about what you both enjoyed or not enjoyed about the experience.

And if you are wondering about the poop: Yes, there is certainly a chance you might see some, but the right preparation can help. There is less likelihood of seeing poop if he empties his bowels ahead of time, and if you go slow.

It is also not the time to use your favorite white sheets if you are worried about poop. Make sure to have some wipes on hand as well.

Now that you know how to peg someone for the first time, it’s time to add pegging on your sex bucket list!

Because pleasure gets better the more you know what you like and need! Learn more about women sexual wellness, self pleasure tips, and more.