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Learn how to safely double anal penetration the butt with these tips from DP expert Alex Cheves
#Anal Play Advice#Partner Play

The 15 Best Tips for Double Anal Penetration

Last Updated: Aug 14, 2023 / By Alexander Cheves

Double-stuffin' the butt is a hot and full-filling fantasy for many, but without the right precautions, it can hurt or even cause injury. Seasoned DP expert Alex Cheves shares his tried & tested double anal penetration tips!

Double penetration — DP — 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 involves taking two dicks up the ass at the same time. 

But DP isn't easy, and if you go too fast or don't use enough lube, it can hurt. Some positions are better than others for DP, and it's just a fact: some dicks are better for DP than others.

Here are 15 tried and tested tips on double anal penetration and how to make this hot fantasy happen:

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 very long way in training the butt to relax — and training the mind to become familiar and comfortable with the sensation of your butt stretching and opening. I started years ago playing with a small black butt plug — playing anal solo and sometimes with a friend. In retrospect, the plug was pretty tiny, but at the time I really struggled to take it.

How to train your ass for double anal penetration

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.

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 and ready to take things to the next level.

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

Put lube on both cocks and inside your butt. I recommend using silicone anal lube because it won't dry out after a few minutes. But bear in mind that silicone lube can stain bed sheets and cannot be used safely with most toys without causing a chemical reaction, so plan ahead. If you plan to play with toys in the same sex session as you plan to try DP, I recommend using water based lubes that you can mix with powder, like J-Lube, K-Lube, X-Lube, Fist Powder, and other similar lubes.

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, fuck-ups, messes, practice time, and careful positioning get edited out.

Porn makes every sex act look easy, but DP is actually pretty hard, and most DP positions are difficult to do for long stretches. I tell everyone to treat DP as a fun, adventurous moment, an attempt — "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 failure in DP 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. 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, prowess, 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.

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 out with 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.

Best DP sex position to do double anal penetration

EXPLORE: The best positions for first time anal sex.

Some folks suggest fingering at this point to warm up a butt for a second dick, but I don't like fingering unless it's several fingers — one finger just feels like a pencil poking me — and several fingers can be hard to do at this point with one dick already inside you. If this is your first time doing double anal penetration, 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.

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 slid 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.

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: 6 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. With this position, 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 that are 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.

13. Chemical help... helps.

DP has worked best for me when I've had a drink or two, gotten a little stone, or popped a magic mushroom.

14. Gotta have my pops.

Poppers are a common inhalant that has been widely and recreationally used for gay sex since the 1970s. Although poppers are mostly harmless, they are not without health risks. They are dangerous for folks with heart conditions to use, and they cannot be used with medications that thin the blood, which include most pills for erectile dysfunction (Viagra and Cialis).

Poppers are generally made of chemical compounds called amyl nitrates and similar variations of them, which relax smooth muscle tissue (like the tissue of your anus), increase heart rate, and cause a brief, euphoric high. But this must be said: poppers are an unregulated market and many products sold in sex shops as poppers are fakes and knock-offs. Some can be made of toxic chemicals very different from standard poppers.

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.

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.


Found these tips on double anal penetration handy? Read our most popular guides on anal cleaning, prostate orgasm training, or visit our Anal Academy for the latest info on butt stuff!

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