Pegging can be terrifying.
I mean, it's essentially asking you to strap on a foreign, weird harness you've never used, attach this odd appendage to your body and then make it pleasurable for your partner—who's probably been fantasizing about this for a long, long time. What part of that sounds not scary!?
It's no wonder a lot of people refuse to try strapping on a dildo at all at all; it's a whole lot of responsibility and expectation to put on someone who has probably never "penetrated" anything else in their whole lives—or possibly even thought about doing it before.
However, with just a bit of planning and some research, it's possible to feel a lot more prepared to give your first pegging. It can seem pretty scary at first, but after reading some articles, picking the right items and having a supportive first partner, you'll find that pegging might not be as scary as you initially assumed. (Trust me; I've been where you are—to the point where my first pegging session ended in tears.)
READ: Pegging: Everything You Need to Know to Make It Pleasurable for You and Your Partner.
So, here I am to offer a step-by-step guide to getting ready to give your first pegging. You're welcome to skip around this page as necessary to make the guide work for you.
It's your information. Make it work for you.
Now that you know how to prepare for it, let's talk about how to make it all come to life.
To enjoy your first pegging, you'll need to buy a harness and a dildo.
A kit designed with beginners in mind, like Sportsheets Strap-On & Silicone Dildo Set, is an option, but those kits generally cut costs when it comes to the strap-on harness. In a dream world, you'd get an expensive, well-built harness and dildo for your first exploration—but it's hard to justify a $200 expenditure on a new activity.
So, while beginner pegging kits can be a great, cost-effective way to get all of your gear in one stop, keep in mind that their harnesses are generally subpar—and if you like the idea of pegging as you try it, consider upgrading your harness as you go.
I really, really recommend against a strapless strap-on dildo for beginners! These kinds of dildos can be difficult and frustrating to deal with for practiced peggers! That said, many bottoms fantasize about these types of double-sided dildos—so make keep in mind you can always explore them later!
Kinkly already has some amazing guides on buying a strap-on harness and dildo. (I'm probably a bit biased since I wrote many of them, but still.) Check out these pegging gear guides:
You need to know the basics of anal sex if you're going to be penetrating anyone anally. Especially if you've never penetrated a butt before, this is stuff you need to know. If all of that is "TLDR" for you, the basic must-knows are:
Here are some of the anal sex must-reads I'd recommend:
Now it's time to have a talk with your partner.
I'm not sure if you're looking into pegging because your partner initially brought up the idea. If they didn't, it's definitely time to bring it up with them. Talk about why it appeals to you; talk about what you'd like to do.
READ: The Shy Person’s Guide to Talking About Sex.
Here are some sample questions to get the conversation going:
As a beginner yourself, I strongly, strongly suggest you do not peg anyone who has never had anything up their butt. Remember: You have no sensation in your faux penis. This can make it hard to judge what's going on. When your receiver also has no idea what's going on with their own body...well, that's when things get dangerous.
Instead, take some time to enjoy some anal pleasure with anal sex toys and fingers for a month or two. Give your receiver time to learn what anal sensations feel like—and what they shouldn't feel like. Ideally, you want your receiver to be able to tell you when things are going too far or give you tips to help you pleasure them.
There's a line between "pleasurable stretching" and "painful stretching." Someone who has never done anal will not be able to tell you the difference—and won't be able to provide any feedback.
READ: Anal Sex Toys 101.
There are definitely people out there who refuse to do anything anally until they've been pegged by a woman for the first time. Please use caution if anyone demands this of you.
Not only does this present a high risk for harming someone, but it's also a red flag of someone shirking their own responsibility for pleasure and safety during sex.
Pegging can be just as special after going down the path of anal stretching to get ready for strap-on sex—especially since the receiver will know what's going on with their body.
Unfortunately, as the "giver" of this experience, you'll likely be expected to have everything ready.
Regardless of who's getting all the gear together, I'd recommend:
If you'll be doing any anal play with your fingers, have your fingernails trimmed down.
Let's be honest for a moment. Depending on your receiver's diet and bowel movements, things can be a bit more messy than you might have anticipated.
If the receiver is experienced with enemas, they could do a few enema rounds before the pegging. However, improperly-done enemas can actually loosen poop, which makes it much more likely (and, to be honest, watery) to encounter during pegging. Only try enemas if you're practiced and experienced in doing them.
Unless you're doing deep fisting or using intensely large toys, you don't need to worry about much poop if your receiver regularly has solid bowel movements. Pegging with slimmer/shorter dildos may involve smears and a little bit of dirty lube.
READ: 10 Things to Know About Fisting Before You Even Think About Trying It.
Most people don't start to encounter large amounts of "mess" until they're doing really rough play, having long sex sessions, or using giant toys.
Harnesses are tricky little things.
Some of them are trickier than others, but unless you're really practiced, it can be hard to make it look "sexy" while you're trying to figure out where that damn strap goes. For that reason, if you want to look sexy while putting on your harness, practice ahead of time. Get it tightened up and close to your body measurements beforehand. Pre-load the dildo and have the straps laid out in a way that makes sense when trying to put it on.
On the other hand, nobody says you need to put on the harness in front of your partner. Before your session, you can simply excuse yourself into another room to put on your harness and dildo. You're just "gathering what you need."
Ready to play? Now that all of your prep-work is out of the way, I hope so!
You can wait to put on your strap-on harness and dildo until you're mid-scene and ready for pegging; but I personally prefer to wear the during foreplay as well. Not only did I spend a pretty penny on my harness and want to show it off, but there's a certain bit of added anticipation if your partner can constantly see the toy you'll be pegging them with later.
READ: This Inexpensive Sex Toy Is My Go-To Foreplay Tool.
To start, I recommend enjoying whatever foreplay activities the two of you typically like. If that includes an intense make-out session, then do that! If that usually includes some sort of kink activity or service activity, do that.
If you're feeling confident, you can include your dildo and harness in your foreplay as well. Have them "jerk off" your cock for you. If you both are into it, you can “force” them to give you a blowjob. You can slide your harness to the side and allow them to orally pleasure your actual naughty bits. It's really up to what you're comfortable with—and what the two of you enjoy.
Once your partner is ready, slip on a glove and lubricate your fingers thoroughly. Start off with one finger and gently tease the entrance. You can use your other hand to stroke their genitals or you can just let them focus on the anal sensations. Draw this out as long as you'd like.
When you're ready, slowly slide a single finger into your partner. When they're pushing back into your fingers (or when they express verbal interest for more), you can slip in another finger. Don't rush things. If your partner isn't ready for more, that's fine. As long as your partner can comfortably get two fingers in during a warm-up, you'll be able to find a dildo they can take during a pegging. That's one of the benefits of strap-on sex over "biological" penis-in-vagina sex: you can pick a different dick at any moment.
READ: Everything You'll Ever Need to Know About Choosing the Right Dildo for You.
After selecting which position you're going to be in, help your partner get situated. Once they're in place, you can go ahead and stand in your partner's field of vision (or ask for their help) to get your dildo nicely lubricated. If your fingering gloves look dirty, just switch out your gloves for a new pair to apply fresh, clean lube to the dildo.
Once you're sure things are really lubricated, it's time to take your place behind your partner. This is honestly the hardest part for me. Getting your dildo lined up in the "right" spot takes a bit of trial and error. It helps if you take your lubed hand, probe the hole, and then directly hold the dildo to control the tip as you push your hips into them.
In particularly difficult positions, I'll even use my other hand to hold the back of the dildo (underneath my harness) to ensure the dildo is going in the direction I want.
Slowly, and patiently, push into your partner's butt. This is going to be harder to do than you think. Your initial instinct is going to be to slide all the way in and get comfortable, but that can be jarring for receivers—and possibly painful. So go in slowly and well-controlled.
This may leave you using core muscles you haven't used in years—and you might need to pull out just to give yourself a break from the odd position you've been holding. Even if your muscles are holding up OK, be prepared to stop and possibly pull out if your partner shows any discomfort. Most of the time, the receiver just needs a bit of time to get accustomed to the dildo's size.
READ: The 5 Rules of Anal Play for Straight Men.
After you insert the dildo, you can remove your lubed gloves and toss them onto a corner of the bed. Now your hands are free of lube and any mess and free to explore your partner without worry about spreading any stickiness.
With your dildo inside, I recommend you do whatever movement feels most natural for you to start with. Most vulva-owners seem to lean towards grinding to start. Try grinding and see how it feels. Once you're feeling more comfortable, pull out a little bit—just a bit!—and slide back in. Get used to that.
From there, you can experiment with how far you're pulling out. If you pull out all the way, there's no guarantee the dildo will go back into the hole—especially if you're using a very flexible or very small dildo. So you might end up pulling out all the way, see the dildo move a bit because of the sudden release from the hole, and then try to push back in...only to slide your dick up your partner's back. This happens more often than you'd think. And because you have no physical sensation inside the dildo, you may not even know until your partner goes "Ummmm." Then you have to repeat the earlier instructions to slide it back in.
So for that reason, I really recommend starting out with small, shallow thrusts until you learn the length of the dildo. Once you know where that "sweet spot" is (that spot where you only have about an inch left of the dildo inside them) you can enjoy the longer, fuller thrusts the two of you may want to try.
Finally, with everything going smoothly, it's time to enjoy the sensation of pegging. (To that regard, I wrote an article about how to achieve orgasm during pegging. For future peggings, that might be something you want to worry about.)
For now, though, worry about getting comfortable with a strap-on harness and dildo. If your dick slips out, don't stress! It happens all the time. Just slide it back in and continue...and enjoy the whining sounds your receptive partner will make when it happens ;)
READ: What Your Sex Noises Mean.
Whether either of you orgasm will depend on the sensations and what's going on.
Don't forget you can "command" your receiver to touch themselves; or you can touch their genitals for them. All of the combined stimulation will likely lead to orgasm for the receiver. But if it doesn't, that's okay too.
There's no hard and fast "rule" about pegging as the final sex act. You can definitely transition from pegging to oral or anything else to ensure everyone's sexual needs are met.
Just try to be conscious of any of the butt bacteria hanging around your strap-on dildo and harness after you pull out. You don't want to get messy lube all over your bedsheets if you can help it.
I only really recommend three sex positions for a beginner. You can explore any position you want (literally any under the sun!), but these are the ones I've had the best luck when introducing newbies to pegging.
The Doggy Style Position.
I'm sure I don't need to explain what doggy style sex looks like.
This one is really simple to do—but at the same time, with many pegging pairings, the height difference doesn't quite work. You can try having the receiver bend over the side of the bed and see if that helps, but it may not.
That said, when it does work, doggy style is great for pegging because it allows you to see what you're doing, doesn't require you to hold up any extra weight and gives you the freedom of being outside of the receiver's field of vision—which is especially helpful when you're new.
This position shares a lot of similarities with doggy style—but it will be unique to the two of you in its exact angles and placement. (The Flat Doggy Style tends to be good variation on this position.)
Have your partner lay on their tummy on a soft surface (I recommend a bed). If they have a penis, make sure it's positioned in a comfortable manner—especially if they're erect. From there, climb on top of their body, rub your dildo between their cheeks and enjoy the tease.
How you choose to achieve penetration is up to you, but you'll probably find the "best" position for you while you're playing around (that's why I recommend the teasing.) As you're making them shiver with anticipation, you'll likely find how you like to hold yourself up in this position.
I personally like to have the receiver close their legs together while I place my knees on either side of their body. You can do it the opposite way—with your knees between theirs—it's up to you.
With this position, you once again get the benefit of not being looked at. In addition, the Speed Bump Position allows you to see what you're doing and also tends to lead to shallower penetration—making it less likely you'll accidentally push in too far and hurt your partner.
This feels like a good time to remind you to change up your pegging position anytime you want.
For example, getting into the Grand Slam Position is easy from the Speed Bump: Stay up on your knees and just rock your hips, kneeling upright, for shallow penetration without putting body weight on your partner.
You can lean forward and support your upper body on your hands and do more of a "humping" motion. For added closeness, you can even put your entire body weight on your partner and "grind" against them.
The Cowgirl Position.
If you want to lay back and enjoy without doing so much of the work, consider the Cowgirl Position—which puts the receiver, regardless of gender, on top.
You lie down on the bed, and you let your partner be on top—and be in charge of taking the dildo to a level of their own comfort. This can be pretty nerve-wracking for people who are new to anal receiving, so make sure you discuss this ahead of time. You'll get to enjoy the experience of "laying back and watching" as someone else fucks themselves on your appendage. This one is pretty simple to achieve—all you have to do is lay there and watch—but don't forget to verbally encourage your partner and use your hands to pleasure them while they ride you.
Once you're done, toss any disposables and wash anything that needs it.
Your partner might want a shower (and you might, too). Depending on what you were wearing during the pegging, you might find your shirt and underwear covered with bodily fluids or lubes—that's why I recommended bringing a change of clothes. Your receiver can expect to have a bowel movement or two after the pegging (because of the excess lube and air), but again, it just depends on how rough the two of you were.
READ: 5 Tips For Practicing Intentional Aftercare.
Once everybody is clean, you can go right back into basking in the afterglow of your hot-as-fuck sex. (OK, so it might have been "pretty hot, but could use improvements.")
But, hey, it's your first time, and that's a-OK! You've practiced, you've learned more and it's going to be even hotter next time. You got through your first time—and, hopefully, you're ready and excited for a lot more in the future.
