Pegging can be terrifying. I mean, I'm asking you to strap on this foreign waist 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 that a lot of women refuse to try pegging 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 even thought about doing it before.

However, with just a bit of planning and some research, you'll feel a lot more prepared to give your first pegging. It can seem pretty scary at first, but after reading some articles, spending some time picking the right items, and having a supportive first partner, you'll find that pegging might not be as scary as you initially assumed. So, here I am to offer a step-by-step guide to getting ready to give your first pegging. Follow the steps if you need a comprehensive guide. You're also welcome to skip around as necessary to make the guide work for you.

Step 1 - Buy a Harness and Dildo

I don't want to cover the already-covered ground, but in order to enjoy your first pegging, you'll need to buy a harness and a dildo. We recommend finding a kit that is designed with beginners in mind, like Sportsheets Strap-On & Silicone Dildo Set. I really, really recommend against a "strapless strap-on dildo" for beginners! These kinds of kits can be difficult and frustrating to deal with even with experience.

Step 2 - Do Some Research

So, we've reached the point where you're definitely sure you're going to be pegging someone at some point. You have your harness and your dildo. You can jump straight into the next steps, but you may find that planning ahead takes away some of the stress. Planning ahead involves looking into a couple different things to be as prepared as possible.

First, do some research to grow your knowledge pool. You need to know the basics of anal sex if you're going to be penetrating anyone anally. There are lots of articles on anal sex here on Kinkly, so read them and pay attention. If you choose to forgo the research, at least choose an easily-takeable dildo size and use much more lube than you think you need. For bonus points, check out some pegging and femdomme websites and read about peoples' experiences - from both the receiver and the penetrator side. This will give you an idea of how things have went, some tips for your own use, and some ideas of what your partner might have in mind.

Step 3 - Learn How to Use Wear Your Harness and Dildo

Now that you know how to comfortably penetrate someone anally, let's talk about about the strap-on aspect. Honestly, you need to get comfortable wearing the harness and "having a penis." It's an odd suggestion, but you should wear the harness, with your chosen dildo, around the house while you have some alone time. Get a feel for how it fits on your body. When you get bored or feel up to it, slide your faux penis between the couch cushions and practice some thrusting. Lie down on the ground and practice some thrusting there. Most vagina-owning people haven't grown up with the practice of thrusting and humping motions, and it's going to take a bit to learn how to make those movements feel "comfortable" to you. So the more practice you can do with no expectations, the better you'll feel about the pegging - and more confident about what you can do with your partner.

For bonus points, purchase an inexpensive male masturbation sleeve or borrow a partner's, put a condom on your dildo, and practice penetrating and enjoying that sensation. You can even slide it between the couch cushions again for more practice that way. Again, the more comfortable and practiced you are, the more smoothly things will go later on.

Step 4 - Communicate With Your Partner

Finally, it's probably time to have a talk with your partner. I'm not sure if you're doing this because your partner initially brought up the idea. If they didn't, it's time to bring up the idea. Talk about why it appeals to you, and talk about what you'd like to do. This is also the point where you should find out what they have in mind, too. Are they imagining an intimate, romantic pegging session, or do they want to be dominated and humiliated? What are you comfortable with doing? How much anal experience do they have - and what dildos will be a good fit for them? Use this conversation to make sure the both of you are on the same page with your upcoming pegging scene.

If, for some chance, your partner expresses interest in pegging, but has never used anal toys before, it's time to put the harness away. As a beginner yourself, I strongly, strongly suggest you do not peg anyone who hasn't had anal experience. Remember that 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 loving anal pleasure with 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. 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.

There are definitely men 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. Pegging can be just as special down the line - especially when your receiver knows what's going on with their own body.

Step 5: Prepare for the Big Event

Now, let's get ready for the "big event." Unfortunately, as the "top" of this experience, you'll likely be expected to have everything ready for the experience. (If you'd like, the two of you can negotiate with your bottom bringing supplies ahead of time instead). Since I'm sure you want this to go flawlessly, here's what I'd recommend bringing to your first pegging: your strap-on harness, any lingerie/clothing, change of lingerie/clothing, your dildo (or dildos), condoms for the dildos, your choice of lubricant, multiple puppy pads/chucks, and multiple pairs of disposable gloves. If you'll be doing any anal play with your fingers, have your fingernails cut entirely down.

Step 6: Be Ready for a Mess

Let's be honest here for a moment. Depending on the diet and bowel movements of your receiver, things can be a bit more messy than you might have anticipated. If your receiver would like to do a couple enema rounds before the pegging, that will reduce the mess, but there's still a chance there will be some. For that reason, be prepared for things ahead of time. Unless you're doing deep fisting or intensely large toys, you don't need to be prepared for much. Smaller peggings may involve smears and a little bit of dirty lube. If you're not particularly bothered by a little poop, you may not take the same precautions I recommended in the previous paragraphs, but these precautions are what I'd recommend if the idea of any mess is what's causing you pause.

Step 7: Put On Your Harness

Harnesses are tricky little things. Some of them are more tricky than others, but unless you're really practiced (which I suggested you do in Step 3), it can be hard to make it look "sexy" while you're lost in trying to figure out where that damn strap goes. For that reason, if you want to look sexy while putting on your harness. Tighten your harness so that it fits you properly.

Don't want to put that much effort into it before your first pegging? No worries! Just do it a bit half-way. Nobody says you need to put on the harness in front of your partner. Before your session, you can excuse yourself into another room to put on your harness and dildo. You're just "gathering what you need." Or consider wearing your harness and dildo underneath the clothing you're wearing; your partner can "discover" your dildo when you get there.

If you like the idea of giving the visual where your partner gets to watch you "tighten it all up" through the buckles (some people really like that!), consider this alternative. Put on your harness in private, do a cursory look to see what all you need to tighten, and then walk into the room where your partner is at, saying "Are you ready to go, honey?" You can easily stay focused on tightening and adjusting your harness (since the hard part of strap placement is done) while your partner gets to enjoy every visual second of it.

Step 8: Starting the Scene

Ready to play? I hope so! Now, you can choose to wait to put on your strap-on harness until you're literally ready for the pegging, but I personally prefer to wear the strap-on harness (and dildo) during all of the 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.

To start, I recommend enjoying whatever foreplay activities the two of you regularly enjoy. 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.

Now that your foreplay is in the bag, it's time to start preparing your partner. Have them get into whatever position is comfortable for them. If you're both new to anal sensations, I recommend your partner get on their hands and knees with their ass in the air. If they prefer to lie down, you can also elevate their hips with pillows or sex furniture to have access to the butt while they're on their back. I recommend putting one of those puppy pads down underneath your receiver's butt to catch any mess or lube. 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. Slowly enjoy teasing them. When you're ready, slowly slide a single finger into your partner. When they're pushing back into your fingers (or when they express interest for more), you can slip in another finger. Don't push 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 that they can take during a pegging.

Now it's time to move onto the actual pegging. Nervous about looking silly? If you're nervous about seeming silly in front of your partner, there's a simple solution: a blindfold. Make it a natural part of your scene to add the blindfold to their face. Now, any hesitations, fumbling with your harness, or other delays will just be part of their "anticipation." They can't see you, so take your time, worry less about what you look like, and just enjoy trying to figure things out for the first time. You can always remove the blindfold mid-scene if you feel more confident, or you can choose to wait until your next pegging sessions to leave the blindfold in the toy box.

After selecting which position you're going to be in, help your partner get situated and move the puppy pad to contain any pegging mess. 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 with a lot of lube. If your fingering gloves look dirty, just switch out your gloves for a new pair to apply fresh, clean lube to the dildo. If you're comfortable with it, take your time to "jerk off" all that lubricant into the right places - and put on a show for your partner.

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 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 take hold of the dildo and help hold the tip of the dildo as you push your hips into them. On 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. 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 size of the dildo.

After the dildo is inserted, you can remove the lubed gloves and toss them to 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 women seem to lean towards a grinding to start - and that's a good place 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 "extend" how far you're pulling out. Basically, if you pull out all the way, there's really no guarantee that 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, the dildo moves a bit because of the sudden release from the hole, and then you try to push back in...only to slide your dick up his 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 that the two of you may enjoy.

What Are the Best Positions for your First Pegging?

I only really recommend three positions for a beginner. You can explore any position you want (literally any under the sun!), but these are the ones that I've had the best luck when introducing newbies to pegging.

The first position is doggy style. I'm sure I don't need to explain what that looks like. This one is honestly really simple to do - but at the same time, with most female-giver, male-receiver couplings, the height difference doesn't quite work. You can try having them bend over the side of the bed and see if that helps, but it may not. This position is ideal because it allows you to see what you're doing, doesn't require you to hold up any extra weight, and it gives you the freedom of not having someone looking at you while you're learning.

The second position I recommend also shares a lot of similarities with doggy style. Have your partner lay on their tummy on a soft surface (I recommend a bed). Make sure their erection is positioned in a comfortable manner. From there, you're going to climb on top of their body. Rub your dildo between their cheeks and generally just tease them. 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 having fun and teasing, 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 - with your knees between theirs. Once again, you get the benefit of not being looked at. In addition, this 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. You also have a few ways about how you want to do this. You can stay up on your knees and just rock your hips, kneeling upright, for shallow penetration. 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. Check out the Speed Bump Position as well as the Flat Doggy Style.

The last position is the "cowgirl" position; only now, it's the "receiver on top" regardless of gender. You lie down on the bed, and you let them be on top - and be in charge of taking the dildo to a level of their own comfort. This can be pretty nerve-wrecking for people who are new to anal receiving, but it's up to the two of you whether this is something you want to do. 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 just because you get to lay there and watch, but don't forget to be verbally encouraging and to use your hands to pleasure your partner as they're on top.

Finally, with everything going smoothly, it's time to enjoy the sensation of pegging. I also wrote an article about how to achieve orgasm during pegging. For future peggings, that might be something you want to worry about. For now, 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.

Whether either of you orgasm will depend on the sensations and what's going on. Don't forget that 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. If it doesn't, that's okay too. There's no hard and fast "rule" about pegging as the final sex act. You definitely can transition from pegging to oral or anything else to ensure everyone's sexual needs are met. Just try to be conscious of the dildo and anything else that might have touched anything from the anal area when doing any other activities. You don't want to get messy lube all over your bedsheets if you can help it.

After the pegging, you can toss disposables and wash anything that was used for the anal sex. Your partner might want a shower - 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 we brought 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.

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 times in the future.