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How To Take It Up The Butt: A Guide To Painless And Pleasurable Anal Sex

I have a love/hate relationship with anal. There have been times when anal sex has felt like hitting the jackpot of euphoric sensations and… Other times? Let’s just say there were times I thought my asshole would never recover. And while the latter is totally enough reason for me to stop taking it up the butt, I like to think of myself as a winner — and a winner doesn’t give up. 

While I always make sure I’m lubed up before doing any sort of butt stuff, I figured that if there are times when anal sex feels really great for me, then the other times when it’s not-so-great, I must be missing some steps in my butt prep. Meaning: It’s time to update the (anal) playbook. 

“Porn and pop culture make us think that you can dive into anal sex on a whim and without any prior preparation, and that’s absolutely not true,” Dr. Evan Goldstein, D.O., nationally renowned anal surgeon, founder/CEO of Bespoke Surgical and co-founder of Future Method tells Betches

By learning the ins and outs of your asshole, what it takes to prep for butt stuff, and everything in between, you can learn how to have anal sex that’ll make you want to back it up some more. 

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Is Anal Sex Painful?

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It shouldn’t be. “If anal play is painful, then something isn’t right,” Dr. Goldstein says. “Sure, you may not find it enjoyable, and it might even be uncomfortable, but these two sensations are not the same as pain.” 

You have to remember that an anus is extremely different from a vagina, so the way you approach it has to be different too. “Any kind of sex can feel painful when there’s a lack of warm-up and lack of lubrication, but since our butts don’t have natural lubrication and are less stretchy than the mouth or vagina, they take additional prep,” Nora Langknecht, certified sex educator and brand and digital marketing manager at FUNFACTORY tells Betches. 

You can just not like anal, and that’s totally fair. But if it’s something you’ve been wanting to try but can’t seem to get past excruciating pain, it’s time to stop and regroup. 

How Do You Prep For Anal Sex?

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You can’t just shove something up your ass and think you’ll have an orgasmic experience. Just like any sex, anal sex takes foreplay. And more than that, it takes a few extra steps of preparation not only to make sure it feels good but also to make sure you don’t hurt yourself. 

“Tearing, swelling, pain, and bleeding are common if you don’t take the proper steps to ease into anal play,” Dr. Goldstein says.

But how exactly do you make sure your backdoors are open for business? Langknecht likes to break it down into a three-step process: exploration, preparation, and penetration.

No matter what type of sex you want to engage in, exploring your body on your own is so important, especially when it comes to anal play. By using your fingers, butt plugs, or even anal dilation sets, you can train yourself to work your way up to anal sex. And no matter what, use lube, lube, and even more lube. 

Preparation for anal sex otherwise can look exactly the way you want it to look. If you want to shower or douche, that’s your prerogative. But before you get to the final step of penetration, make sure you’re doing everything you can to prepare the rest of your body for anal too.

“You can’t have enough foreplay leading into any sexual activity, especially when going up the butt,” Dr. Goldstein says. While the foreplay won’t lubricate the anus the way it might lubricate a vagina, it can still help you relax your muscles, which is super important before anal sex. 

This is why Dr. Goldstein has been working with patients to administer anal botox. And before you go, “WTF?” anal botox is something that’s becoming more and more popular — and can be something to consider if you’re interested in long term solutions to making anal sex easier. 

“Anal botox is a game changer for the anal community and provides controlled relaxation,” he says. While there’s a lot of testing and personalized care involved, getting anal botox (which is very different from getting botox anywhere else) can help you relax back there and make for a lifetime of anal pleasure.

“We have three muscles in our ass, and by giving Botox in the internal muscle (called the internal sphincter), you get just enough laxity to allow for pleasurable anal,” Dr. Goldstein says. 

How Important Is Douching?

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I know you read “douching” above and were just waiting for a follow-up. So let’s get into it. 

If douching makes you feel more confident before letting anyone back there, go for it. But it’s totally up to you. I always use a bidet any time I use the bathroom, but I’m still nervous that rectum penetration is going to cause a very disgusting experience. Sometimes I’ve stopped anal mid-way because I’m scared shitless (or at least I wish) that my partner will pull out, and we’ll both be greeted by my lunch in fecal form. Excuse me while I gag. 

But Langknecht says that shouldn’t be too much of a worry. “The good thing is our bodies don’t store fecal matter in the rectum, so if you’ve had a bowel movement within an hour before play, you should be fine,” she says. 

Dr. Goldstein says that his advice to people who are worried about a shitty anal experience (literally) is to focus on consuming the right amount of fiber and synbiotics every day. “The better our poops are, the more likely we are to have a clean and ready rectum (where anal play actually takes place), which either eliminates the need to douche altogether or reduces the time and effort it takes to douche,” he says. 

Plus, douching too often can have some negative effects on your body. “The more you douche with unsubstantiated products, the higher risk of irritation, and even sexually transmitted diseases and/or injury,” Dr Goldstein says. 

And if you’re really worried about what may come out of you, you can always do a pre-anal test. Dr. Goldstein advises taking a toy that’s close to your partner’s size, lubing it up, and inserting it into your anus slowly. Then, take it out and look at it. Not only will you pre-dilate and pre-lubricate yourself, but you’ll also get an idea of whether you should douche or not. 

And if no matter how much fiber you take or how many anal tests you do, if douching makes you feel more confident, then go for it. Just make sure you’re using a douche that’s good for your microbiome

What Are Some Great Anal Sex Positions?

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So you’ve played with your own butthole, slopped on as much lube as possible, and cleaned your whole body from the outside in. Beautiful. Now it’s ready to have some good, old-fashioned booty sex. But if, before that, you’re a little nervous about what position to get into, here are some anal sex positions that are comfortable and allow you to go at whatever pace you want. 

  • Doggy Style: If you’re not the most flexible person and rather not be contorted into weird positions for anal, doggy style is a great option.  “Either partner can dictate the rhythm and depth, plus, it gives the penetrating partner a great show while you play,” Langknecht says. 
  • Spooning: “Spooning sex is also great since it allows the receiver to control the depth of penetration a little bit more, and it’s also really excellent for grinding,” Langknecht says. 
  • Cowgirl/Reverse Cowgirl: Cowgirl or reverse cowgirl makes it easy to control the speed you’re going at and leaves your hands free to stimulate yourself or your partner. 

Syeda Khaula Saad
Syeda Khaula Saad
Syeda Khaula Saad is a sex & dating writer at Betches despite not remembering the last time she was in a relationship. Just take her word for it.