A Beginner’s Guide to Strap-On Sex

Welcome to the world of strap-on sex! New here? That's okay! That's what we're here for. This guide will walk you through the basic points of strap-on sex - including how to get started with strap-on sex, picking your harness and dildo, and some tips to make your first strap-on sex session as amazing as possible!

How to Get Started

Have you had a conversation with your partner? That's the first step. Like any sexual activity with a partner, enthusiastic consent is the first step.

While you're chatting with your partner about strap-on sex, consider bringing up some questions as well. Are realistic dildos okay or would you like to stick with non-realistic toys? Are there certain positions that both of you are uncomfortable with - or especially turned on by?

If someone is more experienced than the other person, what can be done to help "even the playing field"? Would you like to read some books - or extra articles - together before you choose to indulge? What about the selection of the harness and dildo? Will that be done together as a bonding activity too?

What if your partner isn't interested? You don't necessarily need to have a partner to experiment with strapping on a dildo! Strapped-on dildos can be used with your own hand - or even can be used with penis masturbation sleeves. Those penis masturbation sleeves can be tucked into the couch or sex furniture if you desire the act of "humping" while wearing your harness.

Going solo with your strap-on kink doesn't mean you can't play; it just means getting a little creative!

Read: How to Have a Conversation About Kink With Your Partner

Picking a Strap-On Harness

Selecting a good strap-on harness is vital for a positive strap-on experience. The harness is what attaches the dildo to your body - and an ill-fitting harness can be straight-up uncomfortable or so floppy that the dildo never really does what you want it to.

Plus, an ill-fitting harness just might not feel particularly sexy, and when having sex, feeling sexy is up there as a top priority!

The biggest deciding factor for a strap-on harness is the style. Strap-on harnesses come in a wide variety of styles - and each style has its own pros and cons. The most common styles include jock-strap style, thong-style, panty style, and boxer style. Luckily for us, understanding the differences between these harnesses is pretty simple!

Jock-strap style harnesses and thong-style harnesses are those strappy contraptions that you regularly see as a "harness". Jock-style harnesses have two straps that run along the underside of each of the butt cheeks. They, as you could guess, look like jock-style underwear.

Thong-style harnesses look like - you guessed it! - thong-style underwear. Thong-style harnesses just have the single strap that goes between the legs. The difference between the two is personal preference - though some people find more dildo stability in the jock-style harness while the thong-style harness is easier to push to the side to "take advantage" of the bits normally hidden by the harness.

Then we have the panty harnesses and the boxer harnesses. The harnesses look just like pairs of underwear - only they include a built-in O-ring for using dildos. As you can guess, these harnesses are usually much more comfortable - with some people preferring to wear their harness all day with no issues!

On the other side, their comfort comes with a bit of a loss of stability for the dildo unless you get a very-snug fitting harness. For a lot of people, that's a trade they'll take anyday - especially if you like to wear for long sessions or throughout the day!

Of course, if you're a penis-owning individual poking into the world of strap-on sex, you'll have a whole different list of considerations. Don't worry; we got you. Check out these eight steps for choosing a strap-on harness for advice tailored specifically for the penis-owning among us.

Choosing a Dildo

Before everything else, with strap-on sex, size is the most important. Normally, using a toy by hand allows for more patience and visual cues – which can allow for slower penetration and some comfortable stretching. Simply, using a toy by hand is much more forgiving.

Once you attach a toy in a strap-on harness, a person's entire bodyweight is behind the penetration - in addition to being unable to see or feel where the toy is actually "going". Unlike a biological penis, a strap-on dildo doesn't have any nerve endings to alert the wearer to what's going on, so selecting a toy for strap-on sex that's a good fit is vital.

First off, you need to consider the recipient's comfort. The length of the width of the dildo should be something the recipient can easily receive - and will enjoy. Focus on finding an awesome dildo that feels amazing for the recipient. Part of the fun of strap-on sex is the fact that you can, quite literally, use a dildo with any shape! Take advantage of that! Just make sure that it's dildo that the recipient can comfortably take. This isn't the best time for stretching sessions.

Second off, you might want to consider the strap-on wearer's pleasure and comfort. Are you looking for clitoral pleasure during strap-on sex? If so, a dildo crafted for clitoral pleasure or a dildo with a flat base might provide the best experience. Does direct stimulation feel uncomfortable during strap-on sex? Maybe you'd prefer a dildo with a suction cup base for added roominess. Either way, your dildo needs to have a flared base in order to fit in (and stay in!) your strap-on harness.

Third, don't forget about the rigidity of the dildo. Super soft dildos are likely to “bend” under pressure – and guess what? There's a lot of pressure behind a person's body-weight while strapping that dildo on. You want a dildo that's moderately or very-firm in rigidity. This helps make penetration easier and reduces the likelihood that it will “crumple” under pressure and constantly slip out.

If you're looking for a dildo that can pull double-duty, don't forget to choose toys that will have a good use for you outside of the strap-on harness too!

Read: 8 Steps to Picking a Dildo That'll Rock Your World

Tips for Your First Strap-On Sex

Just like anything in life, the first couple of times you do it, things are going to be new - and might not go as smoothly as you'd like. That's just part of learning something new! At the same time, nobody wants their sex session to feel awkward or be fraught with lots of problems. Let's see if these five tips can help out, eh?

1. Practice Your Harness and Dildo Solo

Using a strap-on harness and dildo can be a whole new experience. The harness, especially, can feel confusing or awkward on your body at first - especially as you're making all of the initial adjustments to get the harness to fit you properly. (Don't want to adjust straps? Consider a panty-style harness.)

We recommend taking some of the pressure off yourself by pulling the harness and dildo out of the package ahead of time while you're by yourself. Give them both a good wash and let them dry.

Afterward, slip the dildo into the harness and slip the harness on. See how it feels. Make adjustments to the straps as necessary. Walk around for a while with the new appendage and see where it feels best on your body. Consider stroking it a few times to figure out the best placement for the base of the dildo. Some people like to place it right above the clitoris for added sensation while other people prefer a higher placement as direct pressure in those sensitive spots can be too much.

Without the stress of another person watching you adjust to wearing this pseudo-strappy lingerie, you have a bit more space to make it work best for you – and add some confidence for when you whip it out in front of your partner next time.

2. Try Non-Penetration First

Nobody says your first use of your new strap-on needs to be for penetrative sex. Especially if you aren't used to penetrating another person, the angles required to achieve penetration can require a whole lot of experimentation!

Instead of focusing on figuring out the penetration angles, consider making your first partnered strap-on session a strictly "no inserting" session. This allows you both to enjoy the feeling of the dildo, naturally find positions where it would comfortably insert if you only shifted your hips a bit further, and draw out the tease of eventually slipping that strap-on cock into someone. It allows you to build your exploration and discovery time into a sensual and teasing bonding experience. That's hard to say no to!

3. Playful Sex is a Great Introduction

There's definitely a time for hot, passionate sex where every second needs to get you closer to sharing intense pleasure with your partner. That time, however, is probably not during your first strap-on sex sessions. As mentioned before, learning the angles and movements will take a little bit for the two of you, so a playful viewpoint on your first strap-on sex sessions is highly recommended.

Be prepared to laugh, communicate about how best to do things (the words "Uh, you fell out" happen almost every time I have strap-on sex!), and enjoy sharing this new experience with each other. The hot and passionate parts can come later when the two of you have established more of a rhythm and have learned how to best enjoy strap-on play with each other.

4. Use a Familiar Dildo

Half of the "battle" of strap-on sex is in the dildo itself. Using an unfamiliar dildo makes that battle a bit worse. If you're familiar with your favorite dildo, you know exactly how much pressure it takes to bend the dildo - and have a feeling for how "long" your factory-added dick is.

If you're trying strap-on sex for the first time, try to use a dildo that's been a favorite for a while. You'll have a general grasp on how long it is (reducing accidental slip-outs!) and will have an easier time getting it initially slipped into your partner.

5. Ask the Receptive Partner to Do the Work

The other half of the battle of strap-on sex is the actual thrusting. If you're new to wearing a strap-on harness and penetrating someone, doing the thrusting is a new motion for your body to learn - and you might find it way more exhausting than you initially imagined.

Worried about looking silly or feeling nervous? Ask that your receptive partner do most of the work. They're likely used to "riding" something - where you may not be used to being the "ridden" one. Person-on-top positions can be perfect if you're new to strap-on sex.

Not only can you enjoy a view you rarely ever seen, but the receptive partner can control the angle of penetration and enjoy the strap-on experience without bringing your nerves into the equation.

Read: Strap-On (Fore) Play

Strap-On Sex While Plus-Sized

Have a larger body than your partner - or just worried that some sex positions aren't going to work well for your strap-on sex? We have you covered there too. These ten tips will provide even more ways to make strap-on sex as fun and stress-free as possible as a person of size!