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A Complete Beginner's Guide to Strap-On Sex

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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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.

8. Don’t be afraid to practice thrusting

Hey, we’re not going to judge you if you want to finesse your strap skills with a little training (just like we definitely won’t judge if it takes a while to find your rhythm). “I’m not embarrassed to admit that I humped some pillows early in my strap-on days,” says Lily. “It helped me get in the zone and figure out the different ways I can roll my hips. Also it was basically masturbating, so win-win.”

Speaking of, don’t forget grinding. “Speaking as a bi woman, I can say people of all genders forget that penetration doesn’t just have to be going in and out and pounding away,” says Spencer. “Roll your hips and grind that strap.”

Take It One Step Further

There are a few things you can do once you’ve tried pegging and decided that you like it.

  • Make your own harness out of rope.
  • Have your partner worship your strap on cock. This works well if you’re into femdom (get other femdom ideas).
  • Your man can perform oral on your dildo.
  • Purchase an ejaculating dildo for an even greater sense of realism.

Of course, you don’t have to go beyond the basics, and you may find that you aren’t interested in strap on play after your first time.

However, it can take a few goes for you to find your stride. After all, sex isn’t always awesome the first time, and that can include the first time you try a new activity even if it’s with a comfortable partner. And sometimes we can think that we’ll enjoy something only to find out otherwise. The important thing is to be honest with yourself and your partner. But even if you decide that strap on sex isn’t for you, it’s not a failure! After all, you’ve learned something about yourself and your partner.

It’s possible that you’ll find strap-on play brings you and your partner closer together and helps increase intimacy due to the vulnerable nature and communication that’s required. Pegging isn’t for everyone, but you’ll never know if you’re not willing to give it a try.

Dont Forget the Rest of His Body

When you’re first getting used to penetrating your man with a strap on, you’ll probably focus on that alone. However, as you get used to it and become more confident in your skill, you can direct your attention elsewhere and not just the strap on tips in this guide. This may mean reaching down to stimulate his balls, pinching his nipples, caressing his body, scratching his back, pulling his hair, or otherwise incorporating his most sensitive spots into your sexual activity.

Learn more: 13 Awesome Male Erogenous Zones

While this advice should help you choose the right strap on and develop the skills you’ll need to be a good lover, these things take practice. Things can go wrong. Or you may discover that either — or both — of you doesn’t really like strap on sex, and that’s okay. 

How to choose a dildo that fits your harness

Most strap-on harness kits have either a hole or an O-ring that you slot a dildo into. They usually come with at least one dildo to start you off. However, once you discover the joys of strap-on sex, you’ll be hungry to try dildos in new shapes and sizes with your harness.

"Don’t forget that you can use cock sleeves and extensions to give extra length and girth to your dildos." – Gyrator53

To choose a dildo that will fit in your harness, start by measuring the internal diameter of your O-ring on the harness. Make sure you’re only measuring the space the dildo will go through, not the full width of the O-ring.

To choose an O-ring or harness that will work with your dildo, measure the circumference of your dildo, just above the flared base (where it will sit in the O-ring).

O-ring sets we recommend

Easy Squeeze Cock Ring Set

Linx Tickler Cock Ring Set

Sex & Mischief Nitrile Silicone Set

Strap-On Dildos

Strap-on dildos either have a realistic penis appearance, or they’ll be designed as non-phallic. The beauty of strap-on dildos is that there are so many to pick from, so you can have a different sexual experience every time. Pick from different materials like silicone, rubber or even glass and they can come in a range of shapes, sizes and even textures.

5. Try strap-friendly positions

Your first few tries using a strap-on aren’t going to be the time to get super wild when it comes to sex positions. Stick with basic positions that feel comfortable and leave you room to adjust the strap-on with your hands if necessary, like on all fours, missionary, or standing beside the bed while your partner lies on its edge. “Your partner can always ride you if you’re having trouble maneuvering your strap,” Lily A., 22, tells SELF. “Finding what feels good and feels natural always takes some experimenting.”

For anal in particular, Cobb recommends having the receiver start on all fours too. “This is one of the most common pegging positions,” she says. “On the bed, couch, or wherever, you get on your hands and knees and have your partner enter you from behind.” She also shouts out lying on your stomach as a similarly newbie-friendly pegging position.

Step Two: Preparing For Strap-On Play

Lube is especially important during anal because the anus doesn’t lubricate itself in the same way a vagina does. Lube also reduces friction and the last thing you want to do is tear up anyone’s anus. I repeat: Never ever have anal sex of any kind without lube and definitely use lube for vaginal sex, if needed, too. Just always use lube, okay? Promise?

If your dildo is silicon, you’ll also want to steer clear of silicon lubes, as they can corrode the toys. Instead, try a  that has all the staying power of silicon, without the corrosion.

(Image credit: Design by Monica Park)

Another tip: Don’t buy anything too phallic if your partner is a cis-male. It’s all up to your comfort level, but Saynt recommends sticking to dildos that look like sex toys rather than penises to prevent your partner from getting hung up on his sexual identity.

Before you launch straight into pegging, Saynt also suggests starting with a well-lubed finger and massaging the anus to relax it. Here, you’ll want to go slowly (seriously). From there, move on to butt plugs and small anal toys. Make sure you check in with your partner regularly to ensure they feel safe and comfortable.

For vaginal stimulation, lube up the dildo well before plunging in and if you’re engaging in butt stuff, prepare for some poop. Pretending there won’t be any fecal matter—or worse, fearing it so much you won’t even do butt stuff—is silly. Trying an enema before anal play can expel any waste from the rectum, but that’s totally up to you, too. Enemas aren’t dangerous, as long as they’re conducted properly. Saynt recommends the Tom of Finland hot douche for those who want to cover their bases.

How to Buy a Strap-On

Here’s the bad news about strap-ons: Getting a proper harness and dildo combination is an investment, both of your time and your money. It can take a while to figure out what you like, and sometimes you won’t learn until after you’ve made a purchase and tried it out. You also really get what you pay for when it comes to harnesses and dildos, so I don’t recommend skimping (especially if you think strap-on play will be a big part of your sex life). It takes some time and patience, but the payoff can make it all worth it.

If you have a nice sex shop in your area, I highly, highly recommend shopping in person. A knowledgeable sales person can walk you through the entire process. Many stores even have strap-on workshops. Being able to look at and touch your harness and dildo makes a huge difference in the buying process. If you have to shop online, read as many reviews as you can. Reviews can provide surprisingly detailed and informative information about your options.

Here are some harness buying tips:

  • Make sure to get an adjustable harness made out of comfortable material (typically leather or nylon). The harness should be pretty snug, to ensure you have maximum control over your dildo. Adjustable straps will help you get the fit just right.
  • Some harnesses can be used with a variety of dildo sizes, while other harnesses can only be used with specific dildo sizes. Make sure you understand which model you’re buying.
  • You can get a harness with a bullet vibrator attachment, which delivers vibrations against your clitoris. Since you won’t feel any physical stimulation from using the dildo itself, a vibrator can be a nice addition.

And some dildo tips:

  • If you have a consistent partner, you may want to allow them to pick the dildo, since they will be the one getting penetrated with it.
  • Make sure your toy is made from body-safe material, typically silicone. A lot of sex toys are made out of porous materials that can release chemical compounds called pthalates. You can read more about this here. If it doesn’t explicitly say body-safe, don’t get it.
  • If you really connect with wearing a dildo, from a roleplay or a gender perspective, you may also want to consider purchasing a soft dildo that you can wear all day. (This is often referred to as “packing”.) These types of dildos are meant to resemble non-erect penises.

Using the Strap-On With a Partner

Once you’ve gotten comfortable with your gear, you may feel ready to start using it with your partner. Here, again, I recommend going slow. Let your partner see you in your new purchases. Wear your harness and dildo as you and your partner make out.

It can also be incredibly hot to have your partner jack off your dildo or give it a blow job, if you’re both comfortable with those activities.

If you want to use your strap-on for penetration, the most important piece of advice I can give you is to use a ridiculous amount of lube. Make sure your partner knows to tell you any time they need you to stop and apply more lube. Remember: Never use like with like when it comes to lube. If your dildo is silicone-based, you won’t be able to use silicone lube with it. Use water-based instead.

You may not ever have had to use thrusting motions during intercourse before. If that’s the case for you, thrusting is going to feel supremely weird at first! You just don’t have the muscles that thrusting develops. A lot of people go comically overboard trying to figure out how to thrust, but I recommend trying to keep your movements more subtle until you get the hang of it. If you have a male partner, ask him for a thrusting lesson. Doggy-style is a great beginner’s position — it tends to be easiest for thrusting newbies, as it doesn’t require the same level of hip strength. Or you may want to try missionary, where you can focus more on grinding against your partner.

If you’re penetrating a female-bodied person, you may get to play the surprisingly difficult game, “Where’s the Hole?” Before you start feeling like a lost teenager desperately trying to lose their virginity, use your fingers to find the vagina, then guide the dildo there.

Communication is always key when it comes to sex, and strap-on sex is no different. Ask your partner to give you a lot of feedback about what feels good to them. Go nice and slow until you both get the hang of it.

How to use a strap-on and get the most pleasure out of strap-on sex

Whenever a new sex toy arrives it’s tempting to dive straight in and give it a go. But if you don’t fully know how something fits, looks or works then chances are it could ruin the intimate moment if you’re trying to figure it all out mid-session.

Get the most out of your strap-on sex experience by following these simple tips for a more pleasurable first (second, and third) time.

Get to know your strap-on

If having a dick is a new experience for you, then before jumping between your partner’s legs, spend time getting to know your strap-on set up one-on-one. From a practical point of view trying on your strap-on before the big moment means you’ll be familiar with the harness and how best to adjust it for the perfect fit.

From an erotic viewpoint, the most powerful sex organ is the brain. While you can’t feel your strap-on in an anatomical way, you can learn to imagine the sexy sensations and build up a connection with your strap-on. Think about how you would like it to be touched, kissed or sucked. Would you want it done differently or the same way as your partner touches your other erogenous zones?

While the wearer may not get much physical stimulation out of their strap-on unless it vibrates or the harness includes an internal plug for the wearer – it can provide a lot of sexy arousal through your state-of-mind. The better you know your new appendage, how it moves, the weight, the texture, then the more likely you are to deliver very satisfying stimulation when with a partner.

Communicate with your partner

Communication during any sex act with a lover is important, but if penetration or pegging is something new to your sexual repertoire, then it’s even more important to communicate during strap-on sex. The harness wearer won’t be able to feel the sensation they’re like you can with the mouth, fingers or penis, so you should ask whoever is receiving how it’s feeling. Perhaps you need to go slower, or the dong is too hard, or the position not comfortable. The more you know, the more satisfying your experience will be.

Practise your thrusting

Maintaining a rhythm when thrusting isn’t as simple as it might seem. If this is a movement you’re not used to, then you may find it tiring when doing it for a sustained length of time. Spend some time practising your thrusting and don’t worry if you find it tricky the first few times when with your partner. Practise really can make perfect.

It’s also worth bearing in mind that ‘thrusting’ doesn’t mean going at it like a jack-hammer. Dildos can feel a lot firmer than an actual penis and may not bend as easily. Going slowly will allow your partner to adapt to the sensation, as well as give you the chance to build up a steady, maintainable tempo.

Lube up

This is especially important if your pegging, because the anus isn’t self-lubricating. Make sure you use plenty of water-based lubricant on the dildo and insert slowly.

Even if you’re not using your strap-on for anal sex, lubricant can help ease unwanted friction between the dildo and your partner, providing extra satisfying glide. Just remember to clean the harness as well as the dildo after play.

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