First Time Pegging: A 'How To' Guide for Beginners

Written by Domina Doll, Lovehoney's Passion, Pleasure, and Empowerment Expert

Last updated 03/11/2021

Pegging (generally known as the act in which a woman anally penetrates a man with a strap-on dildo) is incredibly popular. But what is being pegged, what is getting pegged and what's the best way to go about it?

Read on in Lovehoney’s Pegging Guide to learn how to become an expert pegger.

Pegging (Sexual Meaning)

In recent years, pegging has taken the sexual world by storm. 'Pegging' is traditionally known as the act of a woman using strap-on harness and dildo kits to facilitate anal sex with a man, and indulge in female-to-male strap-on dildo sex. Pegging allows all those little sweet spots inside the ass including the prostate gland, to be accessed and enjoyed to their full potential, which many men struggle with on their own.

If our usage of the term 'pegging' doesn't fit with your gender or relationship dynamic, then we have lots of other Advice guides for strap-on play that are less specific to an m/f dynamic.

Quick Intro Guide to Pegging (and why people enjoy it)

As more men become comfortable with their sexuality and start exploring anal sex play for themselves, it makes sense to invite a partner to help you explore every inch of your body, including areas once thought of as ‘out of bounds'.

The prostate gland is a special part of a man’s body that is directly linked to his penis and testicles, which means that by stimulating this round little nub (about the size and shape of a walnut located around 2 inches in on the front wall of the anus), it will directly stimulate the rest of his genitals and result in some explosive orgasms.

But don’t forget, women get pleasure from pegging too! Using a strapless strap-on can provide her with incredible internal sensations.

Video: How to Use a Strap-On Dildo (to help with pegging for beginners)

Is it your first time pegging? Want to know more about how to peg your man (partner or husband) with a strap-on? Lovehoney's Jess and Sammi have the answers in the tutorial video above.

Pegging for Beginners: Introducing it into Your Relationship

If you’re wondering how to peg your husband (partner or lover), the best starting point is a conversation. The term pegging may need explaining to them (not everyone is au fait with it).

Once you have had the sex convo with them, ask them what their thoughts are on it. Be honest about why you're keen to try it – it could be out of curiosity, the element of submission and domination involved with pegging that many find enjoyable, or playing with gender-bending that turns you on. Or, it may be simply because there are thousands of pleasure-seeking nerve-endings in the anus and you'd like to introduce him to those new, orgasmic sensations.

If you’re a man and you want to know how to get your partner or wife to peg you, the same applies. It could be an equally daunting or exciting prospect to them. For women, doing the penetrating part of sex is still a taboo act for some people to get their heads around, so approach it gently, with honest communication and respect whatever their reaction is to your suggestion.

Your partner may need time to consider whether pegging is something they'd like to do, or they may not be into the idea at all. Whatever the outcome, respect it.

They may wish to ease into it if they have never had their anus touched. So, use plenty of lube and stimulate them gently with your fingers or small toys (such as a butt plug) to get them used to that area of their body being touched—for many it is an undiscovered part of the body when it comes to deriving pleasure from it.

How to Prepare for Pegging with Your Man, Partner or Husband

You and your partner will want to decide what products to use, but the bare minimum will be a strap-on and a water-based anal lubricant. We also recommend condoms, dental dams and latex gloves to keep your backdoor play hygienic.

When it comes to strap-ons for pegging play, you’ve got two choices: the standard jock-style strap-on harness or the strapless strap-on.

The smaller beginner's Strap On Harness Kit (around 5 inches) is great for pegging as the jock-style straps sit snuggly and securely on the body, allowing for a greater, more controlled thrust. They can also come with a small dildo that is perfectly shaped for locating and stimulating the P-spot.

Alternatively, you might like to use a double sided strap-on, such as the Lovehoney Posable Strapless Strap-On. This clever gadget will stimulate her G-spot and his prostate at the same time, thanks to the opposing ends that are both designed for internal use. It features 6 inches insertable length, which is not too intimidating for beginners.

Choose something you both like and that fits your needs. A strap on harness with an O-ring that lets you change dildos, like the Lovehoney Advanced Unisex Strap On Harness Kit, is a wonderful option as it lets you customize your fun.

If you’re new to anal play you will want to choose a small strap on dildo, however, if you’ve explored anal play before and would like something a bit bigger, you can easily try a larger attachment without having to buy a whole new kit.

Recommended pegging products

How to Peg Someone: 5 Tips & Pegging Advice

You’ve got your toys together and have gathered your courage and a sense of adventure, and you are now ready to dive into some exciting anal sex pegging play.

Wait! Before you begin, follow this pegging advice to make sure your sexy time stays sexy. There is nothing worse than an eager first time pegger getting too enthusiastic and potentially causing a painful or awkward situation to arise. So, follow these tips and it will be smooth sailing into his backdoor for you both.

Let’s go!

1. Turn on the Foreplay

With any type of sex, it is important to include foreplay to warm up with first. This is especially true with butt play, because it is not quite as straightforward as vaginal penetration.

In fact, the anus is slightly curved, and the prostate is located on the inner wall just above the perineum. You may have to slightly tilt your angle of penetration to hit the prostate directly, so keep that in mind.

Start out with all the sexy stuff you would usually do—making out, some kinky roleplay if you are into that, oral sex.

2. Lube it Up

Lube is your best friend when it comes to any type of ass play. Make sure to have your sex lubricant handy both when you begin exploring his anus and during sexual penetration as well. You will mostly likely need to reapply the lube a few times during your sex pegging rendezvous. This is because the anus is not a self-lubricating organ like the vagina, so the more slippery stuff the better.

To get him super slick on the inside and avoid the mess of applying lubricant manually, we recommend these trusty lubricant applicators. Simply apply your favourite lube exactly where you want it with a lube tube applicator syringe to avoid messy situations, spills and leakage.

3. Explore First with Finger Play

Now that you’ve applied the lube you are ready to go.

Not so fast, cowgirl!

Explore his ass and inner rectum first with a bit of finger play. Start by donning your latex gloves, add lube to the fingertips, and begin with a rosebud massage on his anal starfish. You can warm up his bum cheeks first, to help him relax and get in the groove, then gently use your pointer finger to massage around his ass hole in a circular motion. You will notice him relaxing with pleasure if his anus starts winking at you. Once he is warmed up enough, you can start applying pressure to his backdoor button (with his permission of course!) so you can attempt to slowly enter him.

His butthole should open naturally and allow you entrance if he is sufficiently ready and aroused. If not, continue to massage his rosebud until he lets you inside, where you will meet the first sphincter muscle. With the tip of your finger inserted, gently (yes, always gently) move your finger up and down and around to slowly stretch the opening and help him relax even more.

Let his anal muscles slowly accommodate your finger as you slide in deeper and deeper with slow, controlled penetration (not thrusting in and out just yet), until he accepts your entire finger. At this point you may want to try two fingers to stretch him a bit wider, so he is ready for the pegging dildo.

4. Using Your Strap On

Now, if he is ready, it is time to sport that strap-on and get down to business, ie: penetrating your guy.

Apply lubricant to the head of your dildo, and as you did above, begin to penetrate his ass hole slowly, bit by bit. It is important here that he sets the speed and depth of penetration. Once you get the tip of your dildo inside, he can back into it, or thrust his hips up if you are penetrating him missionary style. Once he has a rhythm he likes, you can meet him with the thrusts, angling your hips backward so your dildo hits his prostate.

You may also like to reach beneath his balls and massage his perineum which can stimulate the prostate externally, by pressing up on the sweet spot just behind his balls and before his anus. This is a very sexy erogenous zone, full of pleasure-seeking nerve endings.

Continue to communicate throughout your play time for the best experience. Make sure to stop when he says so, and allow him to control the penetration.

5. Let’s Talk About Poop

Let’s address the elephant in the room: poop. Unfortunately, fecal matter is a normal aspect of any type of ass play. To prepare for this, he can eat a light diet 12-24 hours before anal exploration and go to the bathroom just before play.

A hot soothing bath and a thorough cleaning both inside and out should put you both more at ease. If you are really worried, he can also try an anal douche to get him squeaky clean. Use a condom on your toy to keep it free of any mess and make clean up easier. Lay down a sheet or barrier to protect your bed linens, use gloves and also a dental dam if you are planning any mouth to ass play.

How to Get Pegged

The real trick to how to get pegged is finding the right pegging positions.

To find the best anal positions for your peg-fest, check out our guide, which includes styles like the cowboy, missionary, and the doggy pegging position that will point you in the right direction.

More Pegging Tips

Aside from a sensual ass and rosebud massage, there are lots of other ways to turn his backside on and prepare him for anal pleasure.

Spanking: Try a bit of playful spanking as a warm-up to get his behind nice and red, bringing the blood flowing to his butt cheeks. Increased blood flow helps warm up the entire area, adding to sensation and arousal.

Rimming: Rimming, or tossing your salad, (otherwise known as analingus) involves ass to mouth play, which could entail anything from kissing, licking, tonguing, sucking, and yes, “eating” ass. Not only does it feel amazing, but it is also a sexy taboo you can cross off your bucket list. Be sure to use a dental dam though if you are worried about fluid bonding and STIs/STDs.

Talking Dirty: Anal pleasure is even more hot if you add in a bit of dirty talk during your erotic play date. Try telling him how sexy he is, how hot this is making you feel to see him taking it up the ass, how wet you are getting, moan lots and throw in a few f-bombs as well. Say whatever feels natural in the moment. Usually, providing a verbal play-by-play of the actions and giving him compliments are a win-win and are sure to get him to go over the edge.

Roleplay: To make your foray into backdoor play even sexier, try mixing in a bit of roleplay for good measure. Play out a kinky fantasy you both have been wanting to try but have never attempted IRL, such as a make-believe threesome, a Domme and slave fantasy, or exploring gender role reversal to play with feminine and masculine archetypes.

Wielding a Strap-on: Sporting a strap-on for the first time may not be as easy as you think. Make sure you try it on for size (literally!) before you begin and get all the straps adjusted so it is comfortable, but won’t slip during sex. You may want to dance and prance about with your new faux penis in front of the mirror to get the hang of it, and practice pumping your hips so it starts to feel like a natural part of your anatomy. With a bit of proactive rehearsal, you’ll be a penis strutting pro in no time.

More Anal Toys: While strap-ons are the name of the game, you can also try other “warm-up” toys to get him in the mood. Anal beads are a much less intimidating way to get him into anal play for his first time. Butt plugs are also a great way to try “anal training”, which is getting your booty used to the idea of having something other than the usual suspects inside there. Prostate toys are perfect for hitting that P-spot for amazing orgasms, and what’s even cooler, he can use his sphincter muscles to control the toy with most models.

Guide to Pegging for Beginners: Summary

We hope you have learned lots from this beginner’s guide to pegging. As always, when trying any kind of sexual exploration for the first time, take it slow. There is no rushing anal sex. The more you practice the better you will get, making your peg sesh an orgasmic occasion for everyone involved.

Pegging Tips & Advice for First Timers & Beginners to Remember

1. Remember to reapply lubricant whenever necessary!

2. Start small and work your way up - you don't want to terrify your partner by wagging a huge dong at them for their first pegging adventure.

3. Slow and gentle wins the race—diving in, strap-on first, will only lead to problems so make sure you take your time.

4. Communicate before, during and after to avoid any unwanted surprises. Talk about what you're going to do, ask if they're enjoying it or if they'd like you to go slower, faster or even stop altogether, and be sure to have a post-peg chat to see if it's something you both want to do again.

That brings us to the end of this pegging tutorial. As always, play safe and have fun!

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