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Because We Know You’re Curious...

We at Bustle love giving you tips for how to tap into your sexual potential and troubleshoot when things aren’t going your way in the bedroom. But what about finding solutions to those stressful sexual health situations that inevitably crop up when you’re getting down? Emma Kaywin, a Brooklyn-based sexual health writer and activist, is here to calm your nerves and answer your questions. No gender, sexual orientation, or question is off limits, and all questions remain anonymous. This week’s topic: pegging with a strap on.

Q: I’m dating my first guy who has expressed that he is interested in checking out anal sex. This is pretty exciting for me, because I’m always down to try new things, but I’m at a bit of a loss for how to actually go about pegging him. I looked online a bit and there are so many dildo options, I’m experiencing choice overload! And then, once I have my “cock,” how do I, um, use it? I assume there’s a learning curve, but I definitely don’t want to be a bad lover! Are there things that can go wrong or be dangerous? I’m not into anal myself so I don’t even have my own body experiences to go off of here. Help!

A: There’s nothing more delicious than a lover opening up to you and asking you to help facilitate a new experience for him (or her). It sounds like you’re excited, he’s excited, and you just need a bit of information. So let’s get right down to it, shall we?

What Is Pegging?

First off, what are we talking about here? Pegging sounds more like a yuppie lawn game than something kinky and fun. Well, pegging is defined as the act in which a male-identified person is f**ked in the ass by a female-identified person wearing a dildo. Sometimes people add “heterosexual” to describe the receptive partner, but I think that’s pretty limiting so I’m going to leave it out.

Fun fact: this practice was actually named in 2001 through a contest held by none other than Dan Savage. Keep that in your back pocket for sexual health trivia.

What Is It Like?

Everyone has their own experience, so it’s up to you to make up your own mind, but there are some overarching themes that peggers report. One is that they really dig the role swap from the traditional man-is-dominating-and-doing-all-the-work and woman-is-receptive-and-not-in-control. Learning your partner’s usual experience in this way can feel not only sexy and awesome, but it can help you understand what your partner is feeling a bit more when you’re having sex (and this is true for both partners). Peggers also report that it’s super fun to be in control and watch your lover just fall apart under you, completely taken with pleasure. Rawr!

Well that sounds absolutely fun! But how do you go about actually doing it? Because it does take a bit of preparation. I’ve gone over how to prepare for anal sex elsewhere, but here I’ll go into what you as the one with the dildo should be ready to rock.

What Materials Do I Need?

Before you get down with pegging, it’s important to get all your materials in order. You will need:

Insertive Implement

Since you don’t usually have a cock, you’ll need to procure one. There are a ton on the market, and they come in a bunch of shapes and sizes. When planning a cock purchase, there are a few considerations to make. One is whether you want something inside you while you’re pegging — there are a bunch of options that include an internal piece for you. There are also dildos that vibrate, which isn’t all that realistic but hey, it feels fantastic! Another consideration is visual. How cock-like do you want your cock to be? Are you okay with something that might feel better but look less realistic (because it’s hot pink, for instance)?

Another thing that’s really important to think about is the shape of your cock. In-the-flesh cocks attached to humans are super versatile and can go in all sorts of directions. Not so much with plastic. Many toys are set at angles that are optimal for certain positions. If you feel comfortable going to a sex shop to talk about your toy’s radius with a salesperson, go for it! If you’re of a shyer nature, read some online forums to figure out what sounds most compelling to you. And of course, there’s always experimentation, because every body is different and who knows what is going to work best for you and your lover.

Harness (If Your Implement Requires It)

Some double-headed dildos are hands-free (or at least they say they are — you generally still need a steadying hand in there so one of you doesn’t slide off). Others require a harness to hold your cock in place. It should be obvious if your toy needs a harness, but if you have any confusion, ask a salesperson or look at the instruction manual.

Lubrication

Something really important to know about butts is that they’re not self-lubricating. This means you need lots of lubrication to make pegging work. Depending on what your toy is made of, you can use different types of lube.

Water-based lube is the best lube for toys, because it doesn’t degrade silicone or jelly and it’s the easiest to wash off. It’s also condom-friendly, which is good if you’re using condoms to keep your toy clean or if you want to use it on multiple partners without washing in between. Many people prefer silicone lube for anal sex, because it’s more slippery-feeling and lasts longer. Silicone lube works with certain types of toys, but it degrades silicone and jelly, and it’s not condom-friendly. Oil-based lube degrades most toys, including those made with jelly, plastic, and silicone, so don’t use it with your new cock.

Towel (If You Want It)

Lube gets everywhere, and butts are butts, so sometimes it’s a good idea to put down a towel. Because it’s really not sexy to be worrying about your sheets (or making your partner worry about your sheets) when you’re getting down.

How Do I Actually Peg?

Okay so the scene is set, the toolkit is out, now what?

Make Sure Your Partner Is Relaxed And Turned On

Even if your partner has had anal sex with multiple partners in his life and is a pro, foreplay is important. That’s because the anus is surrounded by a ring of muscle, called the anal sphincter, which is designed to keep in feces. Your sphincter needs to be relaxed to allow something to pass through it. Start with something small like a finger, get your lover in the mood, work up to it.

Get Slippery

Remember that lube we discussed earlier? Use it. Lots of it. Probably two to three times the amount you think you need to use. Spread the lube both on your partner’s butt and on your dildo. Keep the bottle close by for reapplications throughout.

Choose A Winning Position

As mentioned previously, store-bought cocks are usually best at one or two positions. So it’s up to you to decide what position works best. If your partner is new to this, it’s a good idea to let him choose the position, or put him in one that gives him as much control as possible to set the pace and stop if it gets too intense. Great options include having him sit on your lap or spooning him while you’re both on your sides. Doggystyle can be the easiest for insertion, but if you can’t see your partner’s face, it can be hard to see his reactions and gauge how you’re doing, and he’ll have no control over the speed and penetration depth.

Go Slow

When you’re ready for actual penetration, the best rule is to GO SLOW and take the lead from your partner. Your main job is to keep him feeling turned on and relaxed, because it’s when you tense up that anal sex can hurt. A good rule of thumb is to penetrate in a little, then stop and wait for him to get used to the feeling. Then continue, little by little, until you feel comfortable and hit a delicious stride.

Health Considerations

While pegging isn’t a high-risk health activity, there are some health considerations to be aware of.

Sexually Transmitted Infections

If you share toys without cleaning them in between or changing condoms, you can transmit a number of sexually transmitted infections (STIs) including chlamydia, syphilis, herpes, and HIV. Luckily, most of these can’t survive in the air for long periods of time, so your risk for getting them goes down over time. But just to be safe, wash your toys in between uses and humans.

Bacteria

This shouldn’t shock you, but butts contain a bunch of bacteria. And that bacteria shouldn’t be shared between partners, no matter how in love you are. In particular, if you get some anal bacteria into your pussy, you’re in for the opposite of a treat, in the form of a yeast infection or urinary tract infection.

The Bottom Line

If you’re down and your partner is down, pegging is a really great sex act to try. And if you like it, then you just added another fun thing to your sexy toolbox! YUM!

But, and I cannot state this enough: make sure your partner actually wants it. As with any sex act, F**K YES consent is absolutely necessary. This can get sometimes put by the wayside when power play comes into the picture, which is one of the draws of pegging. If you and your partner decide you want to peg roughly, not sweetly and tenderly, then pick a safe word and party on! But make sure that you’re both on the same page, because if not done correctly, pegging can hurt. And hurting your partner is the opposite of what pegging is all about.

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Images: Comedy Central, Giphy