Pegging Instruction
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SEX BLOGS
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A Step-By-Step Guide to Giving Your First Pegging
1 | Your Top 10 Questions About Anal Play - Answered!
2 | An Intro to Anal Play
3 | Why is anal sex still taboo?
4 | Anal Sex Toys 101
5 | Because You Wanna Know: How to Do an Enema Before Anal Play
6 | How to Use an Anal Training Kit
7 | Anal Sex for the Mature Male
8 | 7 Anal Sex Mistakes You Don't Want to Make
9 | Anal Play and IBS - Why It Doesn't Have to Be a No Go
10 | A First Timer's Guide to Anal Sex
11 | Tossing That Salad: The Outs and Ins of Rimming!
12 | Give a Dam: Your Guide to Protected Oral Sex
13 | The Ultimate Guide to Prostate Milking
14 | A Step-By-Step Guide to Giving Your First Pegging
15 | The Beginner's Guide to Anal Stretching
16 | What kind of lubricant should I use for anal sex?
17 | 6 Sex Positions for Great Anal Sex
18 | Anal Sex: After the Entrance
19 | First-Time Anal Too Painful for Your Partner? Here's How to Help Them Enjoy It Next Time
Pegging can be nerve-racking for first timers—whether you're giving or receiving. But by following these steps, you can make it enjoyable for everyone involved.
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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 .)
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.
I don't want to cover already-covered ground; but 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.
(For my thicker-bodied babes, the Spareparts Joque "technically" goes up to a 65-inch size. Mine has easily fit a 74-inch size without too much issue. The Sportsheets Divine Strap-On goes up to a 82" hip as well. For super-slender peeps, I'd also recommend the Joque. Its unique, fold-over Velcro design instantly makes excess material disappear—as opposed to the extra hanging straps of most harnesses.)
I really, really recommend against a strapless strap-on dildo for beginners! These kinds of dildos can be difficult and frustrating to deal with even with experience. 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 :
At this point 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 having a bit of knowledge under your belt can help your pegging experience go more smoothly later on.
So, I recommend doing 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. 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:
If you do have the time to mentally prepare for your first strap-on sex experience, here are some of the must-reads I'd recommend:
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.
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.
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.
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.)
Here are some sample questions to get the conversation going:
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: Y ou 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.
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. (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:
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, 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.
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 (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.
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.
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.
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.
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
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