Sex & Relationships

Anal Sex 101 (You're Welcome)

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We at Bustle love giving you tips for how to tap into your sexual potential and troubleshoot when things aren’t going your way in the bedroom. But what about finding solutions to those stressful sexual health situations that inevitably crop up when you’re getting down? Emma Kaywin, a Brooklyn-based sexual health writer and activist, is here to calm your nerves and answer your questions. This week’s topic: what you should know before you try anal sex for the first time.

Q: My boyfriend has been talking to me about trying anal sex. I'm open to the idea, but I want to know more about it first. Like, do we need to use a condom if we're monogamous, or can I get infections if I don't? How can I make sure it doesn't hurt? What can I expect it to feel like, and how can I make it as much fun for myself as possible?

A: Trying new things is always exciting, but can also be a bit intense, because there is so much you don’t know when you're preparing for anal sex for the first time. Will it hurt? Will you like it? You won’t know until you check it out!

Your anus has thousands of sensitive nerve endings in and around it that can give you pleasure. Most of these nerve endings are concentrated around the opening, but the outer part of the rectum also has them. With the inner part of the rectum, what feels good during sex is mostly the pressure and fullness that comes with being penetrated.

While most people need their genitals to be touched during anal sex in order to orgasm, some people can orgasm just from anal penetration. Researchers think that this comes from contractions of the pelvic muscles, as well as from the psychological excitement of what’s going on. So get excited! And see what happens.

Here's what you need to know before you dive in to the wide world of anal sex ...

Preparing For Anal Sex

As with any new experience, you need to know how to prepare. Here are some things to consider:

Learn Yourself First

You may have noticed that your anal canal, called your rectum, is very tight. Going straight from not having anything in there to having a full erect penis inside it can be intense, and even painful, if not done correctly. We’ll talk more a bit later about how to make sure anal sex feels pleasurable, but something you can do beforehand is get used to having a larger item up there. General practice is to start with a finger (yours or your partner’s) or a thin sex toy, and work your way up. Starting on your own is a great way to become comfortable with new sensations and be able to communicate to a partner what feels good and what feels … like too much.

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Feel Free To Clean Yourself

One of the first misconceptions about anal sex is that it’s unclean because it involves butts. In actuality, your anus has natural bacteria that helps fight infection, and if you clean your body regularly, your butt is as clean as the rest of you. So you don’t need to wash yourself right before you check out anal penetration, although by all means, do so if it will make you or your partner more comfortable. However, you should definitely wash whatever implement you're using (a toy, a penis) so that it doesn't infect you with anything.

Prepare Your Space

You may want to put down a towel — again, to make you feel more comfortable, but also because you’re definitely going to use a lot of lube (more on that later), which, by its slippery nature, gets everywhere.

Lubricate, Lubricate, Lubricate

Something really important to know about your anus is that, unlike your vagina, it’s not self-lubricating. All that slippery goodness that coats your vagina when you’re turned on, and makes sex feel great while protecting your vaginal walls? Not naturally present during anal sex.

Luckily, humans are improvisational creatures, and have invented lube (which is also fun and super useful for vaginal sex). Make sure you have lots of lube on hand when experimenting with anal play — even if you’re using smaller implements, like toys or fingers. It will make everything feel much better and be much safer for your body. Just make sure if you’re using condoms that your lube is water-based and not oil-based, since oil-based lube degrades latex.

Shibari Premium Water-Based Lubricant, $10, Amazon

Doing The Deed

So you’re lying there with your partner and some lube. Now what?

Step 1: Get In The Mood

The most important thing is to get really turned on and comfortable. Your anus is surrounded by a ring of muscle called the anal sphincter, which is designed to keep in feces. Your sphincter needs to be relaxed to allow something to pass through it. So do whatever works for you to get yourself feeling fantastic. Some people say that having an orgasm before you try anal sex is a good way to get super relaxed. So get down with yourself, or solicit your partner to help you out!

Step 2: Get Slippery

Once you’re feeling in the mood, it’s time to get lubed up. Remember that if you were about to have vaginal sex, your body would have been busy preparing you by getting all wet and juicy. Since your anus can’t do that on its own, give it a hand! (But actually, you probably want to start with a finger.) Put lube both inside and around your anal opening and on whatever implement you’re planning on using — whether it’s a finger, a toy, or a penis.

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Step 3: Go Slow

When you’re ready for actual penetration, the best rule is to GO SLOW. This is why it’s important to trust the person penetrating you. You need to be relaxed so that you don’t tense up your muscles, which is what can cause pain. Have your partner penetrate you a little, then stop and wait for you to get used to the new feeling. Once your muscles have relaxed, your partner can continue, little by little, until you feel comfortable with the whole thing. There’s absolutely no rush.

Step 4: Positioning Is Everything

Try a position that gives you as much control as possible — such as sitting on your partner’s lap. Many experts recommend starting off lying on your side and being spooned. Doggy style can be the easiest for insertion, but if your partner can’t see your face, they won’t be able to see your reactions and gauge how you’re doing, and you have no control over the speed and penetration depth.

Step 5: Don’t Forget To Stay Slippery

Remember that during the experience of anal sex, even if you are having the most mindblowing time of your life, you aren’t making any of your own lubrication. Drying up feels not great, and can actually cause pain and tearing of your anal tissue. If you’re feeling a bit dry, tell your partner to grab the lube and reapply. It will only make everything feel even better, so don't feel bad about taking multiple lube breaks.

Health Concerns To Keep In Mind

While anal sex is definitely safe, there are some health risks to consider when you’re getting down in this way.


Many male/female couple pairs enjoy anal sex because you can’t get pregnant with it, and it’s true that pregnancy can’t occur if ejaculation happens in your ass. However, if some ejaculate gets into your vagina, there is a risk of pregnancy.

Sexually Transmitted Infections

The biggest risk of anal sex is the transmission of STIs. Basically, anything you can get in your vagina, you can also get in your anus — including HIV, chlamydia, gonorrhea, syphilis, herpes, and HPV. In fact, because your anal tissue isn’t lubricated, it’s more likely to get tiny tears during sex, which let bacteria into your body more easily than vaginal tissue does. So the risk of catching an STI is actually higher with anal sex than vaginal sex.

If you’re practicing anal sex with someone who has an STI, or someone who may have an STI, consider using a condom. If you’re concerned that you may have gotten exposed to an STI, it’s a good idea to get tested — tell your doctor that you’ve engaged in anal sex, so they can check for infection there.

Vaginal Infections

Another thing to pay attention to is getting bacteria from your rectum into your pussy. Your vagina has lots of bacteria living in it, in a symbiotic yet tenuous balance. Disrupting the balance can lead to yeast infections and all sorts of other netherparts challenges. Additionally, anal bacteria in your vagina can result in a urinary tract infection, which can be painful and unpleasant.

To make sure you don’t share bacteria between your fun parts, either clean the insertion implement (finger, penis, toy) between uses, or just switch condoms. It’s also a good idea to remind your partner to keep track of hands and toys in this regard — maybe he can designate one hand for touching your pussy and clit and another for anal play, so he doesn’t accidentally get you sick!

Muscle Weakening

Finally, since your anal sphincter is a muscle built to keep things in, if you routinely insert large objects through it, it can get stretched. This can make it weaker, which can make it more difficult for you to keep feces inside you until you want to push it out. If you notice this is happening, don't worry! It's a muscle we're talking about, so you can strengthen it. The way to get this muscle stronger is to do kegels — in fact, it's a good idea to do kegels when you're preparing for anal sex, regardless. It will make everything feel even more delicious.

The Bottom Line

The most important thing about anal sex — and actually the most important thing about all sexual acts — is to make sure you’re actually excited about experiencing it. Don’t just do it because your partner wants to, or because you think you should. The sexiest thing you can give a partner is your complete and utter consent — a F&%K YES shouted to the world! If you’re not feeling that, then take a moment and consider whether checking out this new thing is the right thing to do at this moment. No one should be forcing you — if someone is, that’s not consensual sex.

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