How to prepare for anal sex


I hope you enjoy reading this article. If you want to learn more advanced techniques, checkout my book and course, full of helpful, actionable advice.


The Best Uncensored Video Course to Master Sex Techniques

How to prepare for anal sex

Porn perpetuates a lot of lies about sex. Penises, generally speaking, aren’t that big. Bodies typically aren’t that taught, tan, and hairless. Pizza delivery guys aren’t ordinarily beset by sexual opportunity at every turn. But perhaps the biggest lie porn likes to tell is that anal sex is spontaneous. Any porn performer will tell you that prepping for an anal sex scene begins days before the cameras roll. Diets are manipulated, medications are taken to provoke and later prevent bowel movements. Enemas are administered, bloodwork panels are inspected. An unholy amount of lube is always nearby, and shit—despite what we’ve always known to be true—doesn’t happen.  

In the years before I actually got to experience what became my favorite sex act, I’d logged hours and hours of watching anal sex in porn. It was a big part of what fuelled my incessant masturbation! Imagine my surprise when I discovered that anal sex is not something most people could or should do in the spur of the moment. Soon after, I realized that proper preparation for anal sex is what can make it a fantastic experience for both partners. In this blog post, I’m going to break down the 11 things you and your partner can do—alone and separately—to increase the likelihood of both of you becoming enthusiastic analistas. 

Once you’ve absorbed the info herein, head to the anal sex module in the Sex Hacker Pro course.  

In that module, you’ll find six in-depth videos of my gorgeous assistant Michelle and me demonstrating some anal penetration hacks that you’ll benefit from. None of that butt-tastic content would have been possible had we not gone through all of the anal sex prep steps that I’m about to share with you. So let’s get to it. 

1. Think about your motivation for wanting to do anal

This is a step you can do with or without a partner because it’s more of a thought exercise. Its purpose is to get you to sit with exactly why anal sex is something you’d like to be part of your sex life. Have you had it before? If you have, what did you like about it? The taboo nature? The physical sensation? If you haven’t, but always wanted to, what stopped you? In my case, what stopped me initially was a lack of opportunity. I was a late bloomer, and my first partners didn’t always share my appetite for sexual novelty.  

Luckily, I found myself in a scene where anal was a not uncommon part of sex play. In general, my partners had a pretty good grasp of the prep required for optimal anal. Even luckier was that my average-sized penis meant that I wasn’t dismissed out of hand, as a lot of my larger buddies were!

2. Everybody’s got one, so check yours out!

If you’ve never put so much as a finger in your ass, you’ve got some serious balls to think that you should be allowed to be putting things into anyone else’s. You may not have a vagina, but you have an asshole that’s virtually identical to your partner’s. Finding out what it feels like to have something in your rectum will give you invaluable insights when it comes time to put toys, fingers, or your penis into someone else’s ass. 

The next time you’re taking a shower after having a complete bowel movement, get your fingers all soapy and start getting a sense of what’s what down there. This bit of exploration will set you up for success and lead to a little more empathy when you’re with a partner. 

3. Communicate your interest to a partner and get their take

Once you’ve got a feel for why you’re interested in anal, it’s time to broach the subject with your partner. If the statistics are to be believed, you may be interested in what they have to say. Y’see, anal sex is increasing in popularity. Thirty years ago, just 16% of women aged 18-24 said that they had tried anal sex. Now fully two-fifths of women in that age range have tried it. That’s kind of a big deal

Lest you think they are all doing it at the behest of their partners, consider a study that demonstrated that 94% of women who had anal sex in their last encounter had an orgasm. The take-home here is that when anal sex is part of people’s sexual experience, it seems to point to greater sexual satisfaction and wellness.

What I’m trying to say here is that asking about a partner’s interest in anal sex isn’t something you should be afraid of doing. I’ve had very experienced and receptive partners to anal sex. I’ve even had partners who positively prefer anal sex over vaginal sex and can come from it. 

If they are dead against it, ask them if they would like to share why. It may not get you any closer to having anal sex with them in the short term, but what they have to impart may be useful in the future or with future partners. Would this be first-time anal sex for them? If so, why are they so unconvinced about it? 

If they are open but wary, you must take things slow and work up to this gradually. Be prepared to be honest and straightforward about why butt stuff is so appealing to you and why you’d like to do it with them. If you’re both beginners, this chat is going to be especially important and useful. 

One of the reasons people are unsure about anal is the fact that the anus is the point from which poop leaves the body. So let’s address that next.  

4. Talk shit 

The anal opening has an external and an internal sphincter muscle. The external anal sphincter is much easier to control, but the inner one can also be trained to open and close with practice. Ever seen anal gaping in porn? That’s made possible by the training of both the external and internal sphincter muscles. The main purpose of these muscles is to stop fecal matter from dropping out of you at inopportune moments. They are full of nerve endings meaning that licking, fingering, or fucking the anus with a penis or sex toy can be really pleasurable when done the right way. 

Under normal circumstances, the rectum—a tubular-shaped sack that’s around 4 to 6 inches in length in most people, will be clear of any significant amount of poop. Basically, shit doesn’t hang out there in large quantities until it’s just about ready to come out. 


Suppose your partner is interested in butt play but self-conscious about the prospect of a shitty situation. In that case, there are some things she can do beforehand to lessen the chances of such an unwelcome surprise. It all starts a couple of days ahead of the prospect of anal fun and involves diet. In particular, it’s important to up one’s fiber intake and drink plenty of water. This will increase the chances of having a full and complete bowel movement and decrease the likelihood of poopy remnants being left in the rectum

In addition, your partner should multitask next time she’s in the shower, both cleaning her anus and lower rectum with her fingers while getting the lay of the land. If she makes a habit of doing this—as you should too—anal play will be a little more familiar, and she should feel a little more confident about not making a mess. However, if she wanted to go the extra mile…

5. Know thy enema

As mentioned above, an enema (also called an anal douche) are almost always used before an anal scene in porn. That doesn’t mean that they need to be used in real life but should shit happen during a porn scene, production would have to pause while things get cleaned up, and the performers do whatever they need to do to get them back in the mood. And time is money. Another reason enemas are used in anal porn is because the cocks in porn are often off-the-charts large. This means they can more easily reach the far end of the rectum, where fecal matter is more likely to be.  

But while enemas aren’t a must if your partner has gone to the bathroom and showered, she may feel more confident after the deeper and more comprehensive clean an enema can provide. 

An enema kit is a sex accouterment you can pick up at your local pharmacy. Most disposable kits cost a few dollars, while a reusable hot-water bottle-and-syringe kit may be a little more expensive. There are also multi-use enema bulbs which are a little less unwieldy and medicinal-seeming. 

About an hour before you are planning to have sex, the receptive partner will retire to the bathroom and fill the receptacle of whatever type of enema she’s using with warm water. Trust me: she really wants to check that the water is neither too hot nor too cold. She’ll put a little soap or lube on the nozzle, insert it into her anus, and squeeze the water into her rectum. She’ll hold the water until she feels like she needs to go to the bathroom and then expel it into the toilet. She’ll continue doing this until the water runs clear.  And boom! You’re all set up for anal success! 

6. Prep the space  

If you’ve taken all of the steps detailed above, the chances of unleashing an unholy shitstorm are low….but never zero.  Put down an old towel or sheet, have some baby wipes close at hand and, in the relatively unlikely event that shit happens, assure each other that a fuss won’t be made and that a contingency plan is in place. Should the worst happen, scoop that soiled towel up and get it out of the play area. Complete the clean-up operation by jumping in the shower with your partner, and administering some serious TLC.

7. Use Lube 

Unlike the vagina, the anus and rectum are not self-lubricating. What that means is, when it comes to anal sex, there is no such thing as too much lube. You need to use lubelots of lube—not just to help toys and fingers and your cock slide more easily into your partner’s ass, but to protect those delicate tissues from tearing. Because the anus doesn’t self-lubricate, you have to continually reapply lube during butt sex. It doesn’t matter whether you’re inserting a toy, a finger, or a butt plug

There are plenty of fantastic lubes out there, including several that were created specifically for anal play. Just remember that oil-based lubes can cause latex condoms to degrade and break. That goes for natural products like coconut oil too. For condoms, water and silicone-based lubes are your best option, though if you’re using silicone sex toys, a silicone lube could damage them. It’s all about finding the right tool for the job.

8. Try Rimming 

As with all types of sex, a requisite amount of foreplay is generally appreciated. A rim job is oral sex for the butt and an excellent way to warm your partner up to anal touch. That’s because it prepares her psychologically for anal play. If you show you’re down to lick her pucker and put your face on it, she can relax knowing you’re comfortable playing down there. 

9. Anal fingering

After encouraging your partner to pleasure her clit and vulva, let the pad of one gloved finger rest over the opening of her anus. Breathe, wait, and feel for her anus to pucker slightly as it relaxes. That’s how you know your partner’s body might be ready for insertion. That little pucker is the first gate opening. Always tell your partner what you’re about to do so she’s not surprised by a finger sliding up her ass. Take a moment before each step to check in. Don’t persist through pain; if your partner tells you it feels painful or irritating, ask if she wants to stop and always be willing to pull back.

Pro tip: Here’s a great hack for anal insertion used by medical professionals in the emergency room. When your partner wants you to insert a finger, ask her to try to gently push your finger out as you smoothly slide your finger in. While this hack may seem counterintuitive at first glance, think about what happens to the muscles of the anus when you’re pooping. As you push out, the muscles relax and open wider.

Have your partner bear down to push out while you slide your finger to one knuckle deep. See how your partner feels, and if she wants more, repeat the hack to slide your finger in deeper. You never have to insert a finger or a toy all at once. If your partner wants, insert in small stages. Start small so there’s no struggle for your partner the first time she feels new sensations in her anus.

Anything inserted in the butt—fingers, toys, or penis—feels better when angled upward toward the belly button at a 45-degree angle. This 45-degree angle rule was popularized by Gigi Engle, an amazing sex educator colleague of mine, author of All the F*cking Mistakes

This insertion angle makes it so that pressure is applied to the G-spot, clitoral bulbs, or A-spot and cervix, depending on how deep you go. Doing this creates stimulation of the vagus, hypogastric, and pelvic nerves all at once. This is a game of calibration. It might not be exactly 45 degrees for every person; you might need to experiment with angles around that range. But when you hit the right spot, it will feel different to the receiver and should make this act way more pleasurable.

Here’s a second trick: Ask your partner to squeeze your finger as hard as she can. Have her squeeze until she gets tired of holding the tension, and then ask her to relax. When the muscles release, they usually open up even more.

You can also help your partner stretch her anus just like an athlete would stretch a muscle by using PNF stretching (Proprioceptive Neuromuscular Facilitation). This type of stretching was designed to relax muscle and increase tone or activity. This is the reason I love this hack for helping with anal play: it helps your partner develop the distinction between a clenched and relaxed anus while increasing flexibility. With your finger inserted in her anus, ask your partner to squeeze your finger and press your finger up toward her G-spot. 

Keep pressing as she squeezes her anus for five to seven seconds. When she relaxes her muscles, continue to press up even more and stretch the tissues if that feels comfortable. Then turn your finger so you can press to one side and repeat the exercise. Turn your finger, so it presses down toward her spine and repeat. Do the exercise one more time to stretch the final side.

With your finger fully inside, take time to feel the different textures of your partner’s anus and the gentle S-curve shape of her anus. You can flex your finger up to massage her P-spot and G-spot. Don’t slide your finger in and out; just flex up toward her G-spot. Calibrate to find the level of pressure that feels good to your partner. I go over this stretching technique extensively in my Sex Hacker Pro Course.

As your partner relaxes, you’ll feel her anus relax, too. Continue to lube up your finger periodically. After your partner gets used to the sensation of your finger in her anus, you can try other kinds of stimulation. Your partner might like more friction from moving your finger in and out, or she might like the sensation of twisting your finger back and forth. 

You can add in a vibrator or any other kind of stimulation your partner likes so that you’re layering something she already finds pleasurable with the new sensation. If your partner wants to, you can help stimulate her clit and G-spot to orgasm, so she has the experience of linking orgasm to anal stimulation.

Once one finger is comfortable for your partner, you can see if she wants to try two fingers. Bring her to another orgasm with that level of stretch and stimulation, and then try actively stretching her anus a little more. Continue to check in about what feels pleasurable and back off if anything hurts. 

When your partner is ready for you to pull your finger out, ask her to push your finger out as you slide it out. Just like inserting your finger, the muscles relax and open up when your partner bears down, making it easier to slide your finger out.

10. Employ sex toys 

If your partner isn’t ready to try having your cock in her ass, invest in toys. You can get anal training kits with different-sized butt plugs from small to large. Always make sure to buy toys with flared bases for anal play to avoid accidentally getting a toy stuck in the anus. Your partner can wear a butt plug in her anus during vaginal sex to get used to the sensation or you could experiment with anal beads. Again, silicone lube can’t be used with silicone toys, so be sure to buy the appropriate lube. Consider buying a dildo that’s the size of your cock and give it to your partner to masturbate and practice with on her own. When she’s able to fit the toy cock in her butt, she’ll be able to look at your cock and think, game on.

11. P in A

I’d be remiss if I didn’t mention that anal sex puts people at greater risk of contracting HIV, HPV, herpes, and other sexually transmitted infections (STIs) than pretty much any other sexual activity. So, as usual, wrap it up if you feel like you’re in a situation where you should.

Whether you go to penis-in-anus penetration from there depends on the size of your cock and your partner’s comfort. One of the beautiful features I realized about my average-sized cock is that it’s anal friendly. Guys who have larger cocks will likely need to do a lot more warm-up and play with toys before their partner can increase their capacity. Don’t go from two fingers to the size of a soda can. Use toys to stair-step up with two or three stages in between. 

No matter how much butt prep you did, the anus and rectum are bound to have bacteria on and in them that don’t belong in a vagina. In porn, tongues, fingers, toys, and penises are pulled out of one hole and shoved into a neighboring one seamlessly, but IRL, that sort of thing could potentially cause a bacterial infection like a urinary tract infection (UTI). If anything goes in a butthole, it gets washed before it finds itself in a vagina. 

As this post is already pretty long, we’ll get into some of the best anal sex techniques and anal sex positions (it’s not just doggy style or spooning) in a separate article.

Everything I’ve learned about sex that is actually worth knowing


The best uncensored video course to master sex techniques like squirting, anal, oral, fingering, penetration, & multiple orgasms


Beyond Satisfied: A Sex Hacker’s Guide to Endless Orgasms, Mind-blowing Connection, and Lasting Confidence


Rock Her World & Soak Her Sheets! Master My Signature Squirting Technique, as seen on Vice

More Related Resources

Advanced Fingering Techniques

Advanced Fingering Techniques

I cover a lot of ground in the Beyond Satisfied Pro course. Something I don’t scrimp on is granular information about fingering. That’s because your fingers are the most effective, underrated tools for learning how your partner’s body responds to every different kind...

Come Hither Motion

Come Hither Motion

“To create maximum sensation on the G-spot, uncurl your fingers all the way so they press towards the back wall of the vagina. As you uncurl your fingers towards the back wall of the vagina, you’re creating more range of motion. Then you can generate more force as you...