A Step-By-Step Guide to Giving Your First Pegging

Now that you mentally know how to comfortably penetrate someone anally, let's talk the physical aspect.

Honestly, you need to get comfortable wearing the harness and how it feels on your body. It's an odd suggestion but you should wear the harness, with your chosen dildo in it, 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 didn't grow up with the practice of thrusting and penetrating motions, so it may take a bit to discover how to make those movements feel "comfortable" to you. The more practice you can do with no expectations, the better you'll feel about the pegging—and the more confident you'll feel about what you can do with your partner.

READ: He Wants Me to Peg Him. Now What?

For bonus points, purchase an inexpensive penis stroker 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 or some Liberator sex furniture for hands-free practice.

The Liberator Wedge/Ramp Combo.

Not only does this help you rediscover the muscles you'll want to work with during strap-on sex, but it also can help you figure out what feels orgasmic in a no-pressure setting. If you're a vulva-owner, are there certain movements that help grind the base of the dildo into your clitoris—and seem like they could be orgasmic? How can you replicate those in some of the sex positions you're hoping to use? Do you possibly need a different dildo or harness to make those sensations happen? Hands-free orgasms from pegging aren't something most harness-wearers should expect (it's hard to pull off!), but it's possible for many.

The bottom line is this: The more comfortable and practiced you are, the smoother things will go later on.Step 4: Communicate With Your Partner

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. (This is also the point where you should find out what they have in mind, too.)

READ: The Shy Person’s Guide to Talking About Sex.

Here are some sample questions to get the conversation going:

• Is your partner imagining an intimate, romantic pegging session—or do they want to be dominated and humiliated?
• How much are you comfortable with?
• How much anal experience does your partner have—and what dildos will be a good fit for them? Use this conversation to make sure both of you are on the same page with your upcoming pegging scene.

If, by some chance, your partner expresses interest in pegging but has never used fingers or anal toys before, it's time to put the new harness away—at least for now!

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 about how to ensure pegging is pleasurable for them.

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.Step 5: Prepare for the Big Event

Unfortunately, as the "giver" of this experience, you'll likely be expected to have everything ready. (If you'd like, you can negotiate with your bottom to prep everything instead).

Regardless of who's getting it together, here's what I'd recommend bringing to your first pegging:

• Your strap-on harness.
• Any lingerie/clothing.
• Change of lingerie/clothing.
• Your dildo(s).
• Condoms for the dildos.
• Your choice of lubricant.
• Multiple puppy pads/chucks.
• Multiple pairs of disposable gloves.

If you'll be doing any anal play with your fingers, have your fingernails trimmed down.Step 6: Be Ready for a Mess

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, I do not recommend someone unfamiliar with enemas try them out for the first time before pegging because improperly-done enemas can loosen poop, which makes it much more likely (and, to be honest, watery) to encounter during pegging.

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.Step 7: Put On Your Harness

Harnesses are tricky little things.

Some of them are trickier than others, but unless you're really practiced (which I suggested you get in step three), 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.

Don't want to put that much effort into it before your first pegging? No worries! 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."

Alternatively, consider wearing your harness and dildo underneath the clothing you're wearing; your partner can "discover" your dildo when you get there. I've worn mine out to dinner at a restaurant before (with leggings and a dress) and it was a fun bit of foreplay when I placed his hands on my thigh and felt the giant erection resting there.

READ: 10 Foreplay Games to Add Some Heat to the Bedroom.

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, 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: Move Through Your Pegging Scene: Start to Finish

Ready to play? Now that all of your prep-work is out of the way, I hope so!

Step 8.1: Foreplay

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.

Step 8.2: Preparing for Pegging

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. 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.

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 session 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 as needed 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. 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.

Step 8.3: Penetration

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.

Step 8.4: Finding Your Flow

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.

Step 8.5: Enjoying the Ride

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.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 I've had the best luck when introducing newbies to pegging.

Doggy Style

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.

The Speed Bump Position

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.

READ: 6 Sex Positions for Great Anal Sex.

The Speed Bump 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.

The Grand Slam Position

The Grand Slam Position.

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

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.After the Pegging

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.