A Beginner's Guide to Strapping It On

August 23, 2026

Whether you like using them or not, it's hard to deny that the image of someone wearing a dildo in a strap-on harness is evocative and powerful. When you grow from childhood to adult being told that sex and gender are a strict binary, an AFAB¹ person proudly flaunting a silicone cock held by leather straps suggests other possibilities — only one reason that they've been so taboo, and so enticing over the centuries.

A Brief History of Strapping It On

One of the hardest questions to answer about strapping is on is historical: When did the first strap-ons show up? If I were going to answer, strictly from my gut, I'd say that they were invented right after fire, when some pre-historical human started messing around with tying vines around sticks or bones and found out there was a lot of fun to be had.

But as far as the actual historical record is concerned, we can't really say except that they've been around for a looong time. They've been pleasuring people and freaking other people out for at least a thousand years. In the tenth century, Bishop Burchard of Worms (Germany) published a 20-volume collection of Church law. In Book 19, this is just one question that clergy are recommended to ask of women about their sexual "sins":

Have you done what certain women are accustomed to do, that is, to make some sort of device or implement in the shape of the male member, of the size to match your desire, and you have fastened it to the area of your genitals or those of another with some form of fastenings and you have fornicated with other women or others have done with a similar instrument or another sort with you? If you have done this you shall do penance for five years on legitimate holy days.

The church meant what it said about "sin." In 1477, a gender non-conforming woman (who would probably be transmasc by today's standards) named Katerina Hetzeldorfer was tried and thrown in the Rhine River to drown. Strangely, her actual "crime" was never named by the church or the court, and what information we have on her is a bit murky. However a woman named Else Muter testified that she had slept with Katherina, and described her using "an instrument with a red piece of leather, at the front filled with cotton, and a wooden stick stuck into it, and made a hole through the wooden stick, put a string through, and tied it round."²

The ever-valuable YesterQueers has a good, concise account of Hetzeldorfer's case if you want to know more.

The 21st Century Strap-On

In the 21st century, not only do dildos and harnesses come in a wide range of shapes, sizes and materials, but you can use them without being put on trial. So far, at least.

The one problem with the range of shapes and materials is that if you're thinking about trying out strap-on sex for the first time, it can be a little bit intimidating. It's easy to freeze up in front of all the choices. Which dildo do I want? Which harness?

And unfortunately, there's no easy answer to those questions, because the answer is: It depends. You have to choose according to what feels right on your body, to your partner, and what you're planning to do. For instance, do you want to do anal or vaginal penetration? Is there a specific kind of roleplay or atmosphere you're trying for? How much experience do you and your partner have?

Bottoms Up; Or, "Pegging"

If you're going to use your strap-on for backdoor play, pretty much all the standard rules about anal play apply: Relax and open up the receptive partner, use lots of your favorite lube, and pay attention to make sure that everyone's having fun.

You might sometimes hear this kind of sex referred to as "pegging." This came out of a 2001 contest in one of Dan Savage's columns where he had his readers vote on what you should call it when a woman uses a dildo to anally penetrate a male partner. In its original sense, pegging is very specifically focused on heterosexual play between cisgender partners, but people nowadays often use it to talk about anal fucking between trans and queer partners as well.

For your first time pegging, something like the b-Vibe Beginner's Harness is a solid choice. Not only is the harness itself a comfortable and friendly choice for your first time, it comes with a body-safe silicone dildo with a shaft that's 3.9" long and 0.79" in diameter. That's a comfortable size if the receptive partner is just starting out. The Tantus Bend Over Beginner Kit is another excellent choice along these lines, and it comes with two dildos for a little more exploration.

B-vibe beginners strap-on harness set with 5" silicone dildo-The Stockroom

Choosing a Dildo

First of all, not every dildo is going to be built for use with a harness. To work well with a harness, a dildo should have a nice flared base to secure it in the O-ring, such as the Temptasia Reina, shown below.

A teal-colored silicone dildo with a graceful upward curve on a white background.

Notice not only the base, but the graceful upward curve of the shaft, which makes it ideal for hitting the prostate or other hard-to-reach places. This is also an example of where the answer to "What's a good choice of dildo?" comes out to "it depends." For your scene, you might want something that's clearly artificial like this one, or one that's more realistic in shape and color like the Colours Pleasure model or the b-Vibe Slipskin Dildo.

Or, you might prefer the more festively-colored cocks like the Colours Pride Dildo. (You'll have to negotiate wearing that in the local Pride Parade yourself.)

But this is the beautiful thing about strapping on a cock: You get to select the size, shape, texture, and look yourself, a luxury that you just don't get when you're born with a penis. (Much to the frustration of many of us AMAB³ folks.)

One of the major things that you want to keep in mind when choosing a dildo of course, is what it's made of. You're going to find that people have made dildos out of nearly everything imaginable. Most of ours are silicone, which is always a good, solid choice: It's sturdy, flexible, and cleans easily, whether you're using the sink or sex toy cleaner.

Even so, the construction can vary. For instance, both Colours and Tantus make dual-density dildos that have a firm silicone core surrounded by a softer external layer. This gives them a more realistic feel and a little extra flexibility inside you. However, some people prefer single-density cocks for more precise control, especially when thrusting in a harness.

Harnesses

Once you've chosen a cock, you need something to wear it in. You want to make sure that it fits securely and comfortably on your hips, especially during vigorous thrusting. You don't want to have to keep reaching down and pulling the harness back up in the middle of hot fucking.

Along those lines, we've been impressed by the Minx Licorice harness, which features a corset closure in the back, allowing for a high degree of adjustability. It also has a removable ring, which is important if you have a wide range of dildos. You should always make sure that the ring fits securely around the shaft. If it's too big for the dildo, you lose control; if it's too small for the shaft, you risk damaging your nice silicone cock (or not being able to strap it on at all.)

For a softer look, we love the La Femme harness, which is made out of leather with lace trim and pink bows on the straps. It's absolutely what you need for the hard femme who likes to wear the cock in the relationship. Like the Minx, the O-ring is removable, and it comes with two sizes of metal rings. Its counterpart, La Butch, is trimmed with zipper track to give it a more industrial, masculine look.

Conclusion

Is this everything there is to know about dildos and harnesses?

God, no. We haven't even told you everything about the ones we sold. Whole volumes could (and have) been written about this, but we hope that this is enough to whet your appetite and start to explore on your own.

To help out a little more, here are a few more of our favorite items to build your pegging or other strap-on scene with.