A Strapped-In Guide to Anal Sex with a Strap-On

There are many differences between us, but if there’s anything we all have in common, it’s an anus. Why, then, are we so confused about how to have fun with them? In our bi-weekly column, Getting Anal About Anal, a rotating cast of sex workers, physicians and self-proclaimed “bottom supremes” will share their advice and musings on the body’s most mysterious pleasure-hole. This week: Anal sex with a strap-on.

It should go without saying, but strap-ons are for everyone — regardless of what’s between your legs or who you chose to bone, there’s plenty of fun to be had with an extra appendage fastened to your waist. But while anyone can use a strap-on to  penetrate any hole, there are a few unique considerations to keep in mind when it comes to anal. So, strap in, lube up and let’s talk about butt sex with strap-ons. 

Choosing the Right Strap-On

There are two things you have to consider when it comes to choosing the right strap-on for anal sex: 1) the dildo; and 2) the harness. Sometimes, these come together in “kits.” Other times, you have to buy them separately, especially if you want something more customized. 

First, let’s talk about the dick. There are plenty of huge, girthy strap-on dildos out there, but it’s best to stick to toys designed specifically for anal play, many of which often labelled “pegging dildos.” These tend to be thinner and more curved than the average phallic sex toy, making them easier to maneuver and less likely to cause anal tears. For ass-play novices in particular, it’s best to start small. 

That said, if you’ve got a dildo you like — and it has a base that fits in your harness — you can use it for pegging. Still, it’s best to let the person being penetrated select the dildo — it’s going inside their butt, after all. They should be excited about the size, shape and texture, so make sure to communicate about what they — or you — are into. 

When it comes to harnesses, the penetrating partner should choose what they get to wear, as it’s going on their body. There are plenty of options to choose from, but if you want to narrow them down, consider what sort of aesthetic you’d like, how adjustable you need the harness to be and what sorts of sex you’re trying to have in it (for example, some harness have two dildo holes you can use for double penetration). 

Fancy fucking with your ass out? Go for a jockstrap harness — these tend to be extra sturdy, and come with straps that go around the bottom of your ass (this lifts it up a little, giving you the satisfying appearance of a rounder butt). If you’re looking for extra adjustability, go for a corset harness, which can be laced up and tightened as needed — they even come in lace, if you’re keen to amp up the seduction. 

Looking for something casual-looking, that you don’t have to fiddle around with? Plenty of harnesses are shaped like regular panties or boxer-briefs, and you can just slide them on in the heat of the moment without fiddling with laces and straps. Some of these look more “femme” and have things like lace and bows on them. Others are more “masc” and look like something you’d pull out of a three-pack of Haines. Generally speaking, underwear-style harnesses don’t have straps or adjustable belts, so they’re not always as sturdy or customizable as other harnesses, but if you’re into the aesthetic and ease, they’re a good option. 

Most importantly, your harness needs to have a hole or ring that’ll fit your dildo. If your dildo is too small, you can buy a stabilizer to keep it in place. If it’s too large, you might want to buy a larger ring or consider a different harness. When you’re pegging, it’s important that everything fits, and is both snug and sturdy — this’ll make the dick feel like more of an extension of your own body, and minimize any re-adjusting during sex. 

Consider More Specialized Options

Most people think of pegging as something people without penises do, but that’s not always the case. If you have a dick, there are hollow, sheath-like dildos you can put on over your dick, a well as vibrating strap-on toys you can use to enhance sensation. If you have erectile dysfunction or are a trans woman on hormone therapy (which can lower your sex drive and make it hard to get a boner and cum), both are good options for you. There are even double-penetrating dildo and harness sets if you want to use your dick — or two toys — for simultaneous anal and vaginal penetration. 

Not all strap-ons come with a harness, though. There are also strapless strap-ons that can be used by people with vaginas — basically, you slide one end of the toy inside yourself while the other end protrudes out. Theoretically, the vagina “grips” the internal end, allowing you to “wear” it without a harness. Then, just fuck your partner with the longer, phallic end as usual.

Clean Up Your Act — If You Like

From discharge to dick cheese, sex can sometimes be messy. But when it comes to anal in particular, preparation is key. “Douching and enemas aren’t essential steps, but they are processes that some people like to do to feel ‘clean’ ahead of ass play,” explains Poppy Lepora, a sex educator at online sex toy store Self & More.

“Some people prefer to simply have a shower beforehand or plunge straight into anal with no cleaning prep. There’s no right way to approach this; just do whatever feels right for you.” 

If you want to know more about proper anal douching, here’s how. 

Lube Up Liberally

Because your butthole doesn’t self-lubricate, you’ll want to douse your dildo and either your or your partner’s hole in lube before you slide in. According to Lepora, silicone-based lubricants have more staying power than water-based formulas, which makes them a better option for anal (this is true of oil-based lubes, too). Silicone toys aren’t usually compatible with silicone-based lubes, though — it can cause the material to wear down over time. Always check the packaging to be sure, as ruining your best pegging dildo is a costly mistake.

Lube is a particularly important step with strap-ons, as it’s hard for the wearer to gauge pain and discomfort — you can’t feel what you’re penetrating, after all. “Anal should never be painful, so take your time and communicate what feels good and what doesn’t,” says Charlotte Johnson, a kink educator at the U.K.-based sex store MegaPleasure. “The focus isn’t the force of the thrusting, but the sensation from anal penetration.” The more lubed-up you are, the easier it is to enjoy that feeling. 

Warm Up First 

Once you’re lubed and strapped up, it’s time to start teasing that hole. Again, diving straight in is never the best option — plus, why rush pleasure? “The anus is packed with nerve endings, so be sure to warm up with lots of external fingering and/or licking before penetration,” says Lepora. “When you’re ready for penetration, start with one finger, then two. Only when you feel ready should you move on to larger appendages.”

You can use other butt toys liberally here, too — from anal balloons to dainty, preparatory butt plugs, there are plenty of smaller options to warm up your butthole with before you turn to the strap-on. Typically, the more warmed up a butthole is, the better penetration feels. 

Assume the Position and Thrust Away

When it comes to strap-on sex, basically any position you’d usually use for anal can work pretty well. Being able to see your partner’s face is helpful, though.

Lepora says missionary — strap-on wearer on top — is more beginner-friendly than doggy style, where the partner is on all fours being fucked. “You get to check out your partner’s expressions to get a good idea of whether you’re hitting the right spots or not,” she explains. This gives you easy access to the rest of your partner’s body, too. 

Once you’re in, start by thrusting slowly and then build up gradually — it’s a good idea to slide inside gently and give your partner’s butthole a second to acclimate. You might want to grab the dildo with your hand to guide it inside, too, as positioning it can be trickier when you can’t feel what you’re penetrating. Also: Keep your eye on it until it’s in, as you won’t necessarily feel it if it slips out. 

Other than that, anal sex with a strap-on isn’t much different than any other type of penetrative sex. Sure, you take your dick off when you’re done, but isn’t that part of the fun?