The 15 Best Tips for Double Anal Penetration

Double penetration is one of my favorite things to do in bed. I don’t usually love threesomes, but I’ll happily try one if my sex partners are game to double-stuff my butt. DP can mean two penises, a penis and a toy, two dildos, or even fingers – any combination that fills your ass twice at once. Anal DP. It’s a hot, full-filling fantasy for any body.

But DP isn’t easy, and if you go too fast or skip the prep, it can hurt. Some positions are better than others, some dicks are better suited than others, and safety matters more here than in almost any other sex act. If you’ve ever wondered how to do double anal, here are 15 tried and tested tips on double anal penetration to make this fantasy happen – from someone who’s done it plenty of times.

What Double Anal Penetration Actually Means

Double penetration is an umbrella term. It means filling one or more orifices with any combination of penises, dildos, toys, fingers, or fists. There are no prerequisites: anyone can explore it solo, with one partner, or with a group, regardless of genital makeup.

This guide focuses specifically on how to double anal – two objects in one anus at the same time. That’s the most advanced version of DP, and it is not a beginner move. If you’re new to anal play, start with the basics (single penetration, smaller toys, consistent training) and come back here when your butt is ready for more.

Safety, Consent, and the Non-Negotiables

Before clothes come off, agree on a safe word. The stoplight system works well: “green” means keep going, “yellow” means slow down, and “red” means stop. If anyone’s mouth is occupied, set a non-verbal signal too – three taps on the thigh is a reliable one.

Never push through pain. Pain during double anal is your body telling you something is wrong, so listen to it. And skip the numbing or desensitizing creams – they mask the signals that protect you from injury. If you can’t feel what’s happening, you can’t stop before damage occurs. Here’s more on why anal sex shouldn’t hurt and what to do if it does.

Practice safer sex: use condoms, get tested, and never switch holes or partners without changing barriers or washing toys. The anal canal is more susceptible to transmitting infections, so anal hygiene and barrier protection are non-negotiable.

1. Train your butt.

You don’t get better at taking dick by just taking more dick. Kegel exercises, pelvic floor exercises, and regular, consistent toy play go a long way in training the butt to relax – and training the mind to become comfortable with the sensation of your butt stretching and opening. Most people need roughly 45 to 60 minutes of foreplay and warm-up before DP is even on the table.

I started years ago playing with a small butt plug – playing anal solo and sometimes with a friend. At the time I really struggled to take it. That was over eight years ago, and the toys I take now with relative ease are much larger. I specifically trained my butt for ass fisting, but along the way, I realized that DP had become easier and more enjoyable, and that’s when it became one of my favorites.

Double anal is all about girth. Progress gradually with bigger plugs and dildos over time – the Anal Training & Education Set walks you through three progressive sizes. Browse the full anal training collection to find the right starting point for your body so your body adapts safely instead of rushing it.

2. Enjoy the warm-up.

DP should not be the first thing you do in a threesome. DP is the fourth inning. I don’t know if I used that sports reference correctly, but DP is something you do after you’ve been having sex for a bit and are comfortably loosened up.

Treat warm-up as part of the pleasure, not a chore. Use fingers, rimming⁠, and a worn plug to open up gradually. A weighted Snug Plug is a comfortable extended-wear option – you can keep it in during foreplay so you’re relaxed and open by the time you’re ready for two.

3. Use lots of lube – more lube than you think is necessary.

Put lube on both cocks and inside your butt. Friction is the enemy with double the action, so use far more lube than you think is necessary – then use more. I recommend using silicone anal lube because it won’t dry out after a few minutes. Check our guide to the best anal lube for a full breakdown of what works with toys versus skin. But bear in mind that silicone lube can stain bed sheets and cannot be used safely with most toys without causing a chemical reaction.

If you plan to play with toys in the same sex session as you plan to try DP, use water based lubes instead. And here’s the part most guides skip: reapply throughout, not just at the start. A lube shooter helps distribute lube deeply where it’s needed most, especially once there’s already one cock inside you.

4. Remember that double anal penetration is not as easy as it looks in porn.

Porn is great, but it can often be misleading, and it can set up unrealistic expectations for how real-world sex happens. Remember: they’re acting, and all the errors, mess, practice time, and careful positioning get edited out.

Real users consistently say the same thing: it’s logistically awkward, with lots of adjusting angles and limbs. “Where do all the other body parts go?” is a question nearly everyone asks the first time. It will not be a smooth, sleek, or magically effortless experience, and that’s normal.

I tell everyone to treat DP as a fun, adventurous moment – “Hey guys, let’s try this!” – in the middle of a fun threesome rather than the main event. Even if the sex between the three of you is great, DP might not be possible because of basic anatomy, so don’t see a failed attempt as a sign of bad sex. There is so much great sex stuff to do with three people.

5. To help your butt relax, take pressure off your legs and ass.

Positions like this are ones where you’re lying down – on your stomach or back. When you’re having to prop yourself up (on your hands and knees), your muscles are activated to support the weight of the body, which usually makes it harder to relax your hole.

The best double anal penetration positions are ones where you are prone – lying down. Pair that with slow, deep breathing: as you inhale, the anus naturally softens. We’ll cover those DP positions in just a bit.

6. Find the right cock combination.

All penises are great, and I believe size overall has little to do with the quality of sex or the desirability of a top. Skill, speed variation, confidence, appetite for intimacy, communication ability, and many other factors make the great, world-class tops. But for DP, you need two fairly long dicks, because DP positions are hard (almost impossible) without above-average length.

The rigidity of the erection matters too. The more rigid the cock, the easier double anal becomes – a soft or semi-hard penis will struggle to stay in position alongside another one. A dildo plus a penis is a valid, adjustable combo when a second partner isn’t available.

ANSWERED: Is the bigger the better for anal saying true?

7. Try cowboy style.

Here’s how this double anal penetration position goes. Top #1 should lay down on his back on the edge of the bed with his legs hanging over the side. Sit on his cock and face him. Top #2 should be standing behind you. With Top #1’s cock inside you, fold over and lean into him a little bit. When you’re ready, Top #2 can start licking, sucking testicles, eating ass, playing with, and even fingering your ass with Top #1’s cock inside it.

If this is your first time, sit on the larger penis first – it’s easier for the second, smaller one to squeeze in behind. I recommend gently grabbing his dick (which should be covered in lube) and gently inserting it in your own butt. Wait, breathe slowly and deeply, and allow him to gently slide inside until they’re both in you. Once you relax, this position lets you ride Top #1 while Top #2 thrusts from behind.

EXPLORE: The best positions for first time anal sex.

8. Try on your back.

This one starts the same, but I find it’s a bit better for more advanced guys. Tell Top #1 to lay down on his back on the edge of the bed. His legs should hang over the bed, toes touching the ground. Now sit on his dick at the edge of the bed and lay back flat. Your back should be resting on his chest, and you should be facing away from him – facing Top #2.

Put your legs up so that Top #2 can see a dick inside your butt. Rest your ankles on Top #2’s shoulders. Again, he can lick, play with, or finger your butt as you desire with Top #1’s cock inside you. When you’re ready, grab Top #2’s dick and gently slide it in. Breathe slowly and deeply and let him enter. Once they’re both in, they can both thrust. Top #1 is thrusting upward and Top #2 is thrusting from the side.

9. Take a seat.

Sitting on two dicks at once is a more advanced position than the first two, and it can be complicated, mainly because people have legs that often go akimbo instead of being coordinated.

At the start of this position, Top #1 and Top #2 are both lying down on the bed, on their backs. They need to scooch in together so that their testicles are touching and their legs are intertwined. Straddling both dicks, the easiest way to do this is to face one top and away from the other and slowly lower yourself over both of them, cowboy-style.

The butthole naturally wants to stretch into a vertical oval, so having one dick to your back and the other to your front is easier than sitting on two dicks side-by-side, which requires your ass to stretch wide. But more advanced bottoms should try the side-by-side sit – it’s fun.

10. Try the porn split.

This double anal penetration position is the hardest to do, and it tends to feature prominently in gay porn. In this position, Top #1 is supporting your upper body, usually with their arms under your shoulders, while Top #2 is supporting your lower body, usually with your ankles on their shoulders. The idea is that your weight is spread over both of them so that you’re not too heavy.

LISTEN PODCAST: Can we learn buttstuff from porn?

Standing, they slide both their dicks inside you and take turns holding the bulk of your weight so the other guy can thrust for a bit. If both their dicks are long enough (and if you’re small and bendy enough), they can both hold your weight while simultaneously thrusting in you.

If you can achieve this position, it’s hot – but it is maddeningly difficult and always runs the risk of throwing someone’s back out.

More Double Anal Positions Worth Trying

The four double anal positions above are the classics, but there are three more worth trying once you’ve got the basics down.

Side by side

Both tops lie on their sides facing each other, and you lie between them with your back against one. This is a slower, more intimate setup – it gives everyone easy access for kissing and touching, and the pace naturally stays gentle. Good for when you want to feel full without the acrobatics.

Double doggy

You’re on all fours, and both tops penetrate from behind. This one feels familiar if you’re used to regular doggy style, but it demands some coordination from the tops since they’re side by side. It helps if they alternate thrusting rather than trying to go at the same time.

Lower yourself down between two tops

Both tops lie on their backs facing each other, and you slowly lower yourself down between them. Gravity does some of the work here, and you control the depth and pace entirely. This is one of the positions real users recommend most for a first-time double anal attempt because the receiver has full control over how fast things progress.

11. Whatever position you try, let the tops do most of the movement.

DP is rarely an “active bottom” position. You want to be as relaxed and open as possible, and if you move around too much, you’ll encounter a frustrating situation where one top (or both) keeps slipping out.

LEARN: Lessons from bottoming that made Zachary Zane a better top!

When I do DP, I picture myself as a human jackoff sleeve – neutral, static, just a hole. The receiver sets the depth and pace at the start, but once both cocks are in, let the tops handle the rhythm. Use your safe word or stoplight signal for real-time adjustments. With this approach, power bottoms need to chill and let the tops take over.

12. You don’t need a threesome to enjoy double anal penetration.

I love when, after great sex, a top wants to push my limits and slides an anal toy in my butt alongside his dick. This is still DP! I’ve done DP with two dildos, solo and with a partner, and some of my best DP sessions have been with a dick and a dildo. There are dildos on the market designed to be used for DP with a penis – some are fitted with cock rings and loops so the dildo can be “attached” to a dick.

But set realistic expectations for solo double anal with two dildos: it can be work, and it may not feel dramatically better than one. A partner plus a dildo is a lower-pressure way to practice the sensation and figure out what angles and sizes work for you before you involve a second person.

13. Skip the numbing creams and stay present.

Numbing or desensitizing creams are one of the worst things you can use for double anal. They mask the pain that tells you something is wrong, and if you can’t feel what’s happening, you can’t stop before damage occurs.

Relaxation and warm-up do what chemicals pretend to do, safely. Instead of reaching for a tube of benzocaine, spend that time on breathing, external massage, and progressive stretching with toys. Your body will tell you when it’s ready – and that honest feedback is what keeps double anal pleasurable instead of injurious.

14. Set a safe word and check in often.

Before you go any further, agree on a safe word. The stoplight system (green, yellow, red) is simple and works under pressure. Add a non-verbal signal – three taps on the thigh – for moments when talking isn’t an option.

Checking in doesn’t kill the mood. It builds trust. Ask “color?” regularly, and read body language: tensing up, holding breath, or going quiet are cues to slow down or pause. Communication during DP is what separates a great experience from a regrettable one.

15. Don’t get frustrated if DP just doesn’t work.

Some body shapes and dick sizes aren’t optimal for double anal penetration. Frustratingly, two wonderful tops may just not fit together. DP is one of those rare, awesome sex things that require factors to come together – along with some skill and luck – to happen.

If it stays painful, back out and keep training with plugs and dildos. Not every body will enjoy or achieve double anal, and that’s perfectly fine. Progress is slow stretching over time, not a single session.

Let’s face it: DP is very much a porn thing. It looks hot on camera. But it can be great in real life too, so long as you set reasonable expectations, go slow, use plenty of lube, and enjoy the fun and camaraderie of trying something new in sex. Like all sex, chemistry and communication are necessary to make this happen – and these qualities in your playmate matter more than whether or not they can do double anal. Bang good folks and the double-stuffed fun will follow.

What Double Anal Feels Like for Everyone Involved

Most double anal guides focus entirely on the receiver, but DP creates unique sensations for everyone involved.

What the receiver feels

While a single penis stretches the hole in every direction, two penises stretch it vertically – a sensation experienced bottoms specifically enjoy. That fullness, combined with pressure against the prostate⁠, can trigger hands-free orgasms. Double anal dramatically increases the chance of a prostate orgasm for any body with a P-spot, because the combined girth and pressure leave very little room for the prostate not to get stimulated.

What the tops feel

For the penetrating partners, double anal creates a sensation you can’t get any other way. You feel the length of your penis stimulated against the other cock while the girth is squeezed by the hole – described by real users as like “fucking and frotting at the same time.” Both tops report heightened sensitivity from the friction and tightness.

Aftercare and Recovery

Your body just did something intense, so take care of it. Expect some soreness – sex may be off the table for a day or two, and that’s completely normal.

A warm bath with Epsom salts helps relax swollen tissue. Stick to gentle cleaning (no harsh soaps), drink plenty of water, and apply a soothing salve or aloe-based lube to ease any tenderness. If there’s any lingering or sharp pain past a day or two, see a healthcare provider. Recovery matters as much as preparation – rushing back too soon undoes the careful training you put in.

Read more about anal sex aftercare and post-play anal cleaning to set yourself up right.

Frequently Asked Questions

Does double anal hurt?

Only if you rush it. With proper warm-up, training, and generous lube, double anal should feel intense, not painful. Pain is a signal to slow down, adjust, or stop – never push through it.

Can you orgasm from double anal?

Yes. Many people do, often hands-free. The combined fullness and prostate pressure can produce deep, full-body orgasms that feel very different from single-penetration climaxes.

Do I need two partners?

No. You can do double anal solo with fingers or two dildos, or with one partner using a dildo alongside their penis. A threesome is one option, not the only one.

Is double anal only for experienced people?

It’s not beginner anal play, but you don’t need years of experience either. What you need is progressive training – working up to larger sizes gradually – and a patient approach. The Anal Training⁠ & Education Set is a structured way to build up.

What lube should I use?

A generous water-based lube works with all toy materials. Silicone lube lasts longer but can’t be used with silicone toys. Either way, reapply throughout – not just at the start – and consider a lube shooter to get it where it needs to go.

More Guides to Train for Double Anal

Guide to Using Realistic Dildos

Realistic dildos with a flared base are a solid training tool for double anal, especially for solo practice or partner play with one cock and one toy.

How to Use an Inflatable Butt Plug

An inflatable butt plug lets you increase girth gradually in a single session – useful for warming up to the stretch that double anal demands.

Meet Your New Best Butties!

The Butties collection offers beginner-friendly plugs at an accessible price point, a good starting place if you’re building your training toolkit from scratch.

Double Anal Is a Journey, Not a Checkbox

Double anal isn’t about conquering a challenge or checking a box. It’s about experiencing a sensation that nothing else replicates – the fullness, the intimacy, the trust it takes to get there.

The formula is simple: train your butt gradually, use more lube than you think you need, communicate constantly, and never push through pain. Slow, consistent practice pays off.

Ready to start the journey? The b-Vibe Anal Training & Education Set gives you three progressive sizes, a lube applicator, and a guide. Pair it with the Anal Academy for expert-backed education on every stage of prostate orgasm training and beyond. You’ve got this.