Complete Guide to Anal Sex

Complete Guide to Anal Sex

Anal sex is an exhilarating experience, but lots of people are very hesitant to try it out. You almost definitely have some opinions about anal sex, even if you’ve never tried it. In fact, sometimes the people with the strongest opinions have never even tried it.

If you do it right, anal sex can be amazing for both partners. You just need to make sure you have a complete understanding before you get started. With this guide, you can step into the world of anal play with all the preparation you need.

Step One: Communication

Communication is important with sex in general, but it’s especially important when you’re dabbling in something new. 

Don’t Jump It On Them

Before you introduce anal play in the bedroom, you need to introduce it in a fully non-sexual context. When you want to introduce anal sex to your partner, you’ll want to sit down before you actually try anything and tell them that you’re interested in trying anal.

Lead in with something like, “I’ve always been interested in anal sex, and I wanted to talk about trying it out in the bedroom.” If you’re completely at a loss, you can’t go wrong with, “I saw an article on HUSTLER® Hollywood about anal sex and it made me really interested in the idea.” Then, open the conversation up for questions.

Ask the Right Questions About Anal

So, what questions should you ask? The conversation will probably flow smoothly once you get talking, but here are some important points you’ll want to touch on: 

  • What made you interested in anal play?
  • Why haven’t you tried before now?
  • What concerns do each of you have?
  • What are you hoping to get out of anal play?
  • Do you want to penetrate the other partner, be penetrated, or both?
  • Are there any medical issues that might impact anal play?
  • Do either of you have trauma related to anal sex?
  • What are your specific boundaries with regards to anal play?

Always Be Ready to Hear “No” 

This is crucial for any conversation about sex, but you should never, ever push your partner further than they feel comfortable with. It’s nice to move out of your comfort zone a little bit, but only if you’re the one deciding to do so.

If your partner says they’re not interested in something — whether that’s anal sex as a whole or just certain parts — don’t try to coerce them. Respect their boundaries and consider having another conversation about it later.


Step Two: Preparation

Once you’ve decided that it’s time to try things out, you should make sure you’re prepared. Try these on for size before your first anal session.


Some people like to be squeaky clean before they engage in anal. Although you don’t necessarily need to do an enema, there are a few reasons you might want to.

An enema makes sure things are as hygienic as possible, which is important in dispelling some of the taboo surrounding anal. It also allows you to try out fun things like rimming, which involves using your tongue for anal. Enemas can even be sexually fulfilling, which is a good way to start getting in the mood. 

If you do decide to use an enema beforehand, it’s a good idea to get an enema kit. Buying a special kit helps make sure you’re doing it right and staying safe.


If you’re really concerned about pain, you may want to consider an anal numbing jelly or cream. These are specifically made to numb the anus a bit, so you can relax and not worry about whether or not you’re going to feel pain. Just make sure you use them sparingly. It’s important to have some sensation down there; it’ll help you get satisfaction out of the experience. Besides, if it does start to hurt, something might be wrong, and you need to be able to feel that.

Step Three: Lube, Lube, and More Lube

The right kind of lubricant gives you the best possibility of having anal sex with no pain or significant discomfort. Vaginas lubricate themselves, but anuses don’t, and if you go in dry, there’s a serious chance that you can actually hurt yourself. You generally have two choices: water-based and silicone lube.

Water-Based Lube

Water-based lube is the lube of choice for many people who are planning on using anal sex toys. They’re compatible with silicone, which is a popular material for sex toys due to its softness; if you’re using an anal toy and it’s made of silicone, you need water-based lube.

However, it’s not as “slippery” as silicone lube, and while its ability to wash away with water is great for many circumstances, it’s not as useful if you want to try some things out in the shower.

Silicone Lube

Silicone lube is a more slippery form of lube that’s often more helpful for people trying anal for the first time. It’s also likely to last longer than water-based lube, because water-based lube can be absorbed into the skin.

The main hang-up with silicone lube is that it shouldn’t be used with silicone sex toys. It can also stain your sheets, so keep that in mind when making your choice. 

Step Four: Comfort and Enjoyment

Anal play is all about enjoyment. Contrary to popular belief, it’s not just enjoyable for the penetrating partner; it’s very much enjoyable for both parties. To make things even more enjoyable, consider these important points. 

Arousal Is Key

Most people consider arousal largely in the context of vaginal sex because arousal causes the vagina to self-lubricate. However, it also causes a loosening of the pelvic muscles, which makes penetration less painful and more comfortable.

That same concept holds true for anal sex. Arousal makes you much more receptive to penetration and less likely to get hurt or have a bad experience. Don’t be afraid to engage in foreplay for even longer than usual just to be safe.

Don’t Endure Discomfort

A consistent myth associated with anal play is that it’s inherently uncomfortable and doesn’t really have any benefits for the penetrated partner. That couldn’t be further from the truth. If you feel pain or even just start to get uncomfortable, that’s a sign that something’s wrong. You need to stop your partner and try something else — more lube, a different position, increased foreplay, or whatever else makes you feel more comfortable.

everything you need to know about anal play

Anal Play for Women

Many people talk about anal in the context of men; after all, that’s the demographic that most benefits from anal, right? Wrong! Women can have just as much fun with anal as men. 

Anal Orgasms

Most women don’t have a prostate, but that’s actually not the only way to feel pleasure from anal sex. There’s a sort of triple threat when it comes to having anal sex, even without a prostate.

First off, the clitoris; the clit is actually sort of wishbone-shaped, and the “clitoral legs” near the anus can be stimulated during anal sex. Anal also indirectly stimulates the G-spot. Lastly, there’s a spot located deep inside the vagina near the back that can have similar effects to the G-spot, which is also indirectly stimulated.

With all three of these happening at once, you can absolutely have an orgasm just from penetration.

Double Penetration

If you want even more, you can try double penetration. If you’re having sex with one partner, it’s usually achieved with a mixture of sex toys and natural penetration; sex with multiple partners can naturally lead to double penetration as well. There are also double penetration dildos that are shaped perfectly for the job.

Pegging and Strap-Ons

If your partner is interested in being penetrated, you can also do that with the aid of a strap-on. Strap-ons often have a feature that stimulates the vulva and clitoris as you thrust, making it feel even more natural. There are strap-ons specifically meant to stimulate the prostate, ones with a more traditional dildo attachment, and even ones created to facilitate double penetration.

guide to anal play for men

Anal Play for Men

It’s often taken for granted that a man will be the penetrating partner during anal play. But in fact, with the right toys, you may find that you like penetration as much or even more than penetrating someone else.

Prostate Massagers

The all-important prostate is one of the things that makes anal sex so wonderful for men. A prostate massager is specifically shaped to help hit the prostate as easily as possible. You can let a partner have at it or do it yourself; just feel around toward the front until you feel it.

What does “it” mean? You’ll know when you feel it. It’s similar to the feeling you get right before you ejaculate, and can be an amazing thing to feel for an extended period of time.

Other Anal Toys

Prostate massagers aren’t the only thing you can benefit from when it comes to anal sex.

Anal beads are a great option if you like the “full” feeling, especially because it allows you to take in whatever you’re comfortable with and stop when you’ve had enough. Butt plugs can also be a fun option, and can be a great way to introduce anal play in the context of otherwise normal vaginal sex.

Have a look at the different anal sex toys available and see if you find anything you like.

everything you need to know about anal sex

Never Be Afraid to Try Something New

For many people, anal play is a brand new sensation, and that can be a scary thing to experience. However, you should never be afraid to experiment in the bedroom. Whether that’s introducing some kinky toys or cautiously trying out anal sex, you should always feel comfortable with trying something new.

It doesn’t matter if this is the first time you’ve been wondering about anal or if you’ve been interested for years, but been too shy to say anything. You should talk to your partner about trying anal. Who knows — maybe they’re interested but have also been too shy to talk about it. It can only improve your sex life.