As Ilana Glazer from Broad City aptly noted a few years ago, “It’s 2015—pegging is definitely on the menu.” Four years later, the same still rings true. While pegging isn’t yet a staple in our collective sexual repertoire, it’s absolutely an option—and an undeniably intriguing one, at that. The shifting landscape has left many of us contemplating our first-ever strap-on dildo purchase (and realizing how complex the world of strap-on shopping can be).

It goes without saying that strap-on dildos didn’t get their start on Broad City. (Or in that 2013 episode of Keeping Up with the Kardashians where Kourtney offers to peg Scott Disick after he asks her to have anal sex.) The queer community has been having strap-on sex for about as long as strap-ons have existed. So the idea that strap-on dildos are only “cool” now that two of our favorite TV shows have covered them is not only incredibly straight, but also incredibly myopic.

Still, that’s no reason not to buy a strap-on of your own—or at least, to explore the option of doing so. Sexual experimentation is a wonderful and enlightening thing. If you’re interested in exploring the world of strap-on dildos—for anal or vaginal sex; for straight or queer sex; for anything, really—power to you. The first-time strap-on shopping arena can be a complicated thing to navigate. But you’ve already taken the first step: You’ve decided to learn more about strap-on dildos.

Start by shopping toys that are harness-compatible.

Strap-on dildos and dildos aren’t exactly the same thing. The term “dildos” encompasses all kinds of penetrative toys—anal probes, vaginal penetrators, vibrating dildos, etc. The term “strap-on dildos” specifically describes dildos that can be strapped into a harness or pair of briefs for wearable use.

“Strap-on harnesses or briefs often come with O-rings, which are flexible rubber circles that you slot the dildo through to hold it in place,” Sammi Cole, Lovehoney sexpert, tells StyleCaster. “So in theory, every dildo that can be held in place by an O-ring is strap-on compatible.”

But of course, not every dildo can be held in place by an O-ring. Most sex toy stores have specific sections dedicated to strap-on dildos, making it easy to find harness-compatible options. But if you can’t find that section, a good rule of thumb is to shop dildos with flared bases or balls, Cole says; the wide base will make the toy more likely to stay in place during wearable use.

Now that you’ve limited your search to harness-compatible dildos, you’re done, right? Not quite. Because O-rings aren’t one-size-fits-all. Some are larger, to accommodate girthier dildos. And some are smaller, to accommodate slimmer ones.

We’ll get to dildo girth selection and harness shopping in a second. But for now, it’s worth mentioning that you’ll eventually want to narrow your search even further than you already have. It’s not enough to find that’s harness-compatible, you need to find a dildo that’s compatible with your specific harness, Cole says. You’ll want to make sure your O-ring and your dildo have the same diameter. “It’s important to buy a strap-on dildo [your] harness fits like a shoe!” Dr. Jenni Skyler, Ph.D., Adam & Eve sexpert, tells StyleCaster.

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Figure out what size and shape is best for you.

Different dildos lend themselves to different kinds of play. Beginner anal toys, for instance, tend to be a little slimmer than beginner vaginal toys. And Skyler points out that more advanced players tend to enjoy larger, girthier toys (for vaginal and anal penetration, alike).

“As with any new sex toy, it’s always better to start small and work your way up so that the partner being penetrated can get comfortably used to the sensation,” Cole says. (She also points out that smaller dildos tend to be easier to control hands-free than larger ones.) When it comes to shape, Cole recommends starting off with simpler, smoother styles. Non-realistic dildos tend to be softer and more comfortable than realistic ones, and straightforward shapes can be easier to navigate.

But this is more of a suggestion than a hard-and-fast rule. “Shape and length really depends on what the receiver desires,” Skyler notes. “Some receivers want really small and thin dildo penetration. Others want bigger, thicker, longer.” Talk to your partner about what you’re interested in exploring—and what they’re interested in exploring—should make it easier to figure out what size and shape you should be shopping for.

Pay attention to material, too.

Size and shape aren’t the only elements worth considering. A strap-on’s material will affect both the wearer’s and the receiver’s experiences, so it’s worth minding, as well.

Both Skyler and Cole recommend starting with a silicone strap-on. “Dildos that give some element of flexibility are also going to be more comfortable for first-timers, but not too soft,” Cole notes. “You want [your strap-on] to be firm enough to penetrate, but not so hard that it could be uncomfortable.” For this reason, she recommends soft-yet-sturdy silicone.

Plus, both experts note that the material is safe, hypoallergenic, and easy to clean—a win on all fronts.

That said, make sure not to combine your silicone toy with silicone-based lube. In this case, like degrades like. So silicone-based lube can actually erode your silicone toy—which isn’t fun for anyone. If you’re planning to use lube (and you definitely should if you’re exploring penetrative anal play), opt for a water- or oil-based option, instead.

Find a harness you feel comfortable with.

Now that we’ve covered the strap-on dildo basics, it’s time to explore the other half of strap-on sex: the harness.

Start by browsing the strap-on harness sections at some of your favorite sex toy stores (we recommend Lovehoney, Adam & Eve, and Babeland). You’ll likely notice what looks like leather belts and underwear—these are all harnesses (note the O-rings Cole mentioned earlier). But leather and strappy isn’t the only way to do it. There are tons of harnesses that are crafted from cloth and shaped like panties or briefs. These are just as viable as the leather options (again, note the O-rings).

While the underwear- and brief-style harnesses tend to be sized like traditional clothing (small, medium, large, etc.), leather harnesses tend to be one-size-fits-all. That said, many leather harnesses come with “straps that can be adjusted to fit practically any size,” Cole notes. So visit your go-to store in person, try on a few, and see what feels good.

Once you’ve found a harness you like, make sure it’s compatible with the size and shape of the dildo you were interested in. If not, you’ll either need to find a new dildo or a new harness. To avoid a potential mismatch, Cole recommends shopping a strap-on variety pack. These often include dildos in a range of sizes, as well as harnesses with adjustable O-rings. These enable you to explore different kinds of toys with the same harness, all the while knowing you’ll have a perfect fit every time.

Take some time to get used to your strap-on before using it.

Once you’ve bought your strap-on and a matching harness, Cole recommends taking some time to familiarize yourself with it before trying it out with a partner.

“If you’re planning on being the receiver, try using the dildo on your own first—that way, you’ll know what feels good and you can tell your partner,” she says. If you’re planning on wearing the strap-on, try it on and get used to how it feels on your body. “The more you can treat it as a (literal) extension of yourself, the better,” Cole adds.

And when it comes time to actually use your strap-on, take things slow and make sure to communicate with your partner, Cole says. “If you’re receiving, remember that your partner can’t feel the dildo, so they will need you to tell them what feels good!” Cole adds.

And be sure you have everything else you need to keep your strap-on in tip-top shape.

You’ve made it. Now all you really need to do is enjoy your delightful new strap-on—and engage in enough maintenance to keep it in tip-top shape.

For starters, you’ll want to clean your toy after every single use. “Most toys can be easily and safely cleaned with warm water and soap,” Skyler notes. But if you want to take things a step further, you can buy a sex toy cleaner. (Cole recommends the Lovehoney Fresh Toy Cleaner, $14.99. A couple spritzes should do the job.)

While it may seem tedious to post-game sex with a little cleaning, remember: Doing so will not only keep your toys as hygienic as possible, it will also help them last longer. (And since sex toys can get a little pricey, that’s definitely worth it.)

And of course, lube is basically always a good idea. If you’re experimenting with anal penetration, you’ll definitely want to use lube. (Your vagina naturally secretes its own lube, but your rectum does not.) But all kinds of play can benefit from the addition of a little lubricant. Just make sure the lube you’re planning to use is compatible with your toy. (Remember, silicone toys and silicone-based lubes do not make for a good match.)

Intimacy Suppositories with CBD

These plant-based suppositories with 50mg of broad-spectrum CBD are designed to enhance arousal, ease discomfort and relieve tension. Even better? They’re safe for vaginal and rectal use.

A few strap-on recommendations from Adam & Eve sexpert Dr. Jenni Skyler:

Fetish Fantasy First Timer’s Strap-On Set

This fun-colored strap-on set was designed with beginners in mind. (It even has “First Timer” in its name!) Though the attached dildo is slender and beginner-friendly, the harness comes with adjustable O-rings so you can explore different kinds of play.

Bound by Diamonds Harness

Shoppers looking for a particularly fun toy will undoubtedly enjoy this rhinestone-covered strap-on harness (as well as the transparent dildo that comes with it). Many customer reviews have offered the toy high marks, with one in particular calling it great for first-time use.

A few strap-on kit recommendations from Lovehoney sexpert Sammi Cole:

Lovehoney Beginner’s Strap-On Kit

“The Lovehoney Beginner’s Unisex Strap-On Harness Kit is the perfectly proportioned strap-on set for beginners,” Cole says. “This all-in-one bundle contains everything you need to start your experimentation with pegging and penetration play.” (If you’re curious, that includes a 5-inch dildo and a comfortable, adjustable harness.)

Tracey Coz Strap-On Pegging Kit

“For versatility, a strap-on kit like with a [range] of dildos and O-rings is a great place to start,” Cole says. She recommends that beginners try something like the Tracey Cox Supersex Strap-On Pegging Kit. Not only does it offer a range of dildo sizes and an adjustable harness, but it also comes with a bullet vibrator you can tuck into the dildo. That offers the wearer and the receiver stimulation in equal measure.

BASICS Strap-On Harness Kit

“The BASICS Strap-On Harness Kit is also great for first-timers,” Cole says. “A sleek, stylish and comfortable harness holds your choice of two dildos.” (Each of which offers different sensations.) “Flared bases and a set of O-rings also make it easy to change up your toys, and offers stability for care-free fun, Cole adds. “Plus, with fully adjustable waist and thigh straps, it can comfortably fit practically any body shape or size.”

from StyleCaster