As a sex educator, one of the most frequent questions I get is about anal sex. It is simultaneously one of the most common fantasies people have, and one of the most common sexual encounters to go wrong. I can’t even count the number of horror stories I’ve heard about people trying anal sex when they’re some combination of young and drunk, only to have the experience go so badly it turns them off the idea for years - maybe forever. When I start to ask questions, these experiences tend to have a few things in common: lack of communication, lack of warm up and arousal, and lack of lube.

What is anal sex? Need some background reading? Check out What You Need to Know About Anal Sex and Your Top 10 Questions About Anal Play - Answered!

Anal Play the Safe and Pleasurable Way

Slow Down When Engaging in Anal Play
When done carefully and correctly, anal intercourse can be very pleasurable for people of all genders. And learning to do it safely isn’t hard. For starters, you need to slow way down. I don’t just mean engaging in penetration slowly (though I mean that too, and we’ll get there) I mean slowing down and talking to your partner at length before sex even happens.

Talk About Anal Sex Before Trying It
Talking about needs and expectations in advance is one of the best ways to prepare for any sexual experience. You want to know what your partner’s history is with having anal sex, and what they think they’ll need to make it comfortable and pleasurable. Avoid the urge to rush into the sex. If necessary, have conversations by text or in public. This ensures that the focus stays on talking. Plus, the anticipation is part of the fun and the negotiation can even work like dirty talk to get you both excited about what’s to come.

Try Anal Play or Anal Sex Toys On Yourself First
Before you ever try anal penetration with a partner, you might want to try it by yourself. Depending on your flexibility, fingers might work for this, but there are also a wide range of butt plugs and anal toys that you can use. Always be sure that anything that’s going in your butt has a large, flared base so that it doesn’t get sucked up into your body. People end up in the emergency room with things stuck in their butt with alarming frequency.

Read: Don't Have Anal Sex If ...

Even if you’re not ultimately interested in being on the receiving end of anal penetration, it can still be helpful to try it on yourself before you try it on your partner. Nothing really shows you how sensitive the area is, and how slowly you’ll need to go, like experiencing it for yourself.

The Ins and Outs of Anal Intercourse - Safety

Whether alone or with a partner, you want to start with external anal stimulation. The anus, and area around the anus, is incredibly sensitive so touch to this area can be very pleasurable. Start with an external massage, using plenty of lube, and get used to having this area of your body touched. Simply focusing on external touch can be enough for your first try, or first several tries. Adding external touch into your foreplay activities can be a great way to start getting used to the idea of anal penetrating someone, or being penetrated anally yourself.

If you’ve got a vulva, be very careful about cross contamination. Anything that has touched or penetrated the anus must be washed thoroughly before making contact with a vulva or vagina. Otherwise bacteria can cause a variety of unpleasant infections.

Using gloves for anal play can really help with this. When you’re done, you can just remove the glove and your hand is ready for other activities. Gloves have some other benefits, too. They help make sure your hands are soft and smooth, and that finger nails won’t make scratches or tears in the rectum. Tears in this area can be especially troublesome because of the presence of bacteria.

The rate of STI infection is higher with anal sex because of how thin the mucus membranes of the rectum are, and how prone they are to micro tears. Keep this in mind when deciding what kind of barriers to use.

Warming Up for Anal Sex

Ready to get started? Let’s take it step by step:

Talk to Your Partner About Anal Play
Negotiate carefully. Make sure you discuss whether there will be anal penetration or just external anal touch or analingus. Discuss safety needs, what barriers will be used, and how you’ll communicate while you’re having sex.

Get Clean
Some people worry about hygiene when it comes to anal play. Unless you’ve been experiencing stomach upset, this probably isn’t much of a problem. Anal penetration usually doesn’t go past the rectum. There’s another sphincter separating the rectum from the colon and fecal matter doesn’t hang out in the rectum. Just make sure you’ve gone to the bathroom a couple of hours in advance, and you should be good to go.

That said, showering can be a great part of foreplay, or a great way to prepare for sex, just to make sure you can be confidant and relaxed about your body. If you’re really worried, you can use an enema or anal douche, but make sure you do your research on those and only use body-safe products. I’d encourage you to just do an external wash. It can also be useful to keep some baby wipes by the bed, just in case any clean up is needed. Sometimes bodies do unexpected things. It’s helpful to be OK with that if you want to have intimate and adventurous sex. (Learn more in How can I keep anal sex from getting messy?)

Prepare Your Space for Anal Play
For added security when you’re setting in to play, you can throw down a towel. This makes sure that if there is any mess, it’s contained. And since you’ll be using lots of lube, you can keep the sheets from getting slippery.

Get Plenty of (the Right Kind of) Lube
As for lube, make sure you’ve got plenty. A body-safe water based lube is always a good choice, but many people prefer something thicker or more slippery for anal play, like a silicone based lube. This is a great excuse to go shopping at your favorite sex-positive sex toy store and find a lube you love. (Learn more in What kind of lubricant should I use for anal sex?)

While you’re shopping, be sure to avoid any numbing agents that are sold for anal sex (or deepthroating.) Pain is your body's way of telling you something is wrong. You need to be able to hear those signals. Numbing the pain only to find bleeding or tears later is a terrible idea. Plus, numbing products imply that anal sex will always hurt - which is simply untrue. So stick with arousal, lube, and going nice and slow, rather than using numbing agents as a short cut.

Read: 7 Tips for Having Anal Sex That Doesn't Hurt

Start With External Anal Massage
Once you’ve got your lube you’ve got to get it in place. This will be a multi-step process. Using your fingers, you’ll want to spread lube on the outside of the anus. This is a great time to do some anal massage to help with arousal and relaxation.

Moving Toward Anal Penetration

When it comes to anal penetration, especially for the first time, let the person being penetrated control the action. Let them move their body onto you or the toy or fingers that are being used and make sure to keep communicating through this process. The anus is such a sensitive area that even tiny movements can be felt intensely, and moving too quickly can be very painful.

You’ll want to keep adding lube so that the fingers or toys are totally lubed up before they go in, and so that they deposit lube inside the body too. Each object that’s being inserted should be lubed up each time.

The person being penetrated should be both relaxed and aroused. Make sure you’ve done other activities first - massage, making out, whatever works for you. As for relaxing, some of it can be done consciously and some not so much. The external sphincter - the one you’re looking at when you look at your anus - can be consciously controlled. But there’s a second sphincter an inch or less further inside that can’t be controlled by choice, so you really do need to be relaxed for this to not only be possible - but feel good.

You can try some breathing exercises to help your body relax. And it helps to be confident that this process won’t hurt. As soon as there’s pain, your body will clench up, and it’s hard to convince it to let go once that’s happened.

Anal Sex Positions

When you’re deciding on what anal sex positions to try, it’s best to focus on the comfort of the receiver. For this reason, letting the receiver be on top can be a great way to go. That way they can have full control over the pace of penetration, and the pace of any thrusting that may follow. Receiver on top also leaves both partners with hands free for genital stimulation, which can be really helpful for staying turned on and enjoying the experience.

Read: 6 Great Positions for Anal Sex

The classic missionary position works well for many people. This position also leaves your hands free for other things. I’ll emphasize this again, because being aroused is so important, it can be really helpful to stimulate yourself with hands or toys during penetration and all through anal sex. That way you can get exactly the kind of touch you need and your partner can focus on what they’re doing, and on going slowly. If the penetrated person is on their back, having some pillows or a Liberator Wedge under their hips can be a huge help to get the angles to line up just right.

For some folks, doggy style will be the natural fit. There’s some evidence that this position helps the body open up a bit. But be cautious, because in this position it can be easier to slip and go deeper and faster than intended. Even in doggy style you want to let the receiver slowly back up and control the speed of anal penetration. This position can make it a little more difficult to use hands or toys for additional stimulation, but it does allow a lot of freedom of movement.

Once you’ve picked a position and you’re comfortable with penetration, try moving a bit, but slowly. You’re going to need to go a lot slower than you would for vaginal penetration. In fact, you may never work up to those speeds and that’s OK. The anal area is so sensitive you don’t need hard thrusting for the feeling to be intense.

Prostate and G-Spot Stimulation During Anal Play

If the receiver has a prostate, that’s an area you can aim to stimulate during anal penetration. If the receiver has a G-spot (or more accurately the urethral sponge area) that’s also an area you can aim to stimulate. The membranes between the vagina and rectum are thin enough that stimulation to the whole clitoral complex can be felt. For some people, it’s even more pleasurable, because direct stimulation can feel too intense.

Don’t feel like you have to keep at it until one, or both, people orgasm. Anal orgasm is possible for many people, but anal sex can also be one of several things you do during a sexual session. Feel free to mix it up with other forms of play (as long as you’re looking out for cross contamination.)

What happens after anal sex?

Once you’re done with anal sex, everyone involved will want to clean up. It can be especially nice to bring your partner a warm, wet washcloth, but having a bath or shower together can be nice as well.

Make sure you get some snuggles and aftercare. Trying something new can be intense, and you want to give yourself time to recover and connect. After some time has gone by, or the next day, have a chat about what worked well and what could be improved. That way, you can ensure that the next time you try anal sex will be even better.

But what if I don't like anal sex?

Have you tried all these tips and still find you aren't into anal sex? That’s OK! Anal sex isn’t for everyone and if it just doesn’t feel good to you there’s no need to push yourself or feel bad about it. Never let a partner pressure you into doing something you don’t want to do. There are so many different things that bodies can do to feel good. You’ve got plenty of other things you can explore.