Beginner’s Guide To Anal Sex


As more people are discovering, anal sex isn’t just for gay men! Anal play can be pleasurable for men and women. Of course, this hole has gotten a bit of a bad rap because of its function; don’t let that stop you because there are lots of ways around the dirty bits. Here are some very crucial things to know before getting started:

1. Stop and stay. 

The most important rule: if it hurts, pause right where you are. Do not pull out or go in farther and wait for the pain to decrease. To understand anal play, it is important to understand the anatomy of the asshole. The asshole has an internal sphincter and an external sphincter. You can consciously clench, release, and relax the external one, but the internal one has to manually be relaxed with pressure. If the internal sphincter has not been relaxed or stretched in a while (or ever), it can take quite a long time to relax.

Pain is not the game, pleasure is. The pain will stop once the muscles have a chance to relax.

2. Give yourself plenty of time

Because you need ample time to relax and stretch your sphincter, rushing is going to ruin all the fun. Give yourself plenty of time to explore and feel into what is happening in your body. If you are exploring on a partner, your partner is exploring on you, or you are exploring alone, make sure you do not have anywhere you need to rush off too in the near future. This process can take hours, and you may not get much of anywhere on the first try. Be patient and know that it is normal. It might take a few tries to actually get anything inside (getting both sphincters to relax).

3. Lube it up!

Because pain is not the game, make sure to have plenty of lube on whatever you are using to experiment with. For more information on choosing the right lube, check out our other article.

4. Hygiene & STD Prevention

We are playing in the asshole – the same place we excrete waste from our bodies. Even if you are not squeamish, using gloves and condoms (even over toys) is a great way to keep clean up easy. There is a lot of bacteria in your ass. This can potentially cause trouble, especially for folks with pussies, because contamination of the vagina with feces or bacteria from the ass can cause a bacterial infection, yeast infection, or urinary tract infection (UTI). NEVER put something in your butt and then right into your vagina without washing it well with soap and/ or disinfectant, and always be sure to pee before and after anal play to flush out bacteria that may have made it’s way to the urethra. Some people also love their assholes licked; a dental dam or saran wrap is a great way to feel pleasure while keep yourself safe from bacteria. Another nice thing to do is shower and wash your anal and genital areas thoroughly before beginning anal play.

It is important to talk about STDs especially if you are not in a sexually monogamous relationship. Because the anal tissues are much more prone to tearing than penile and vaginal tissues, it can be a lot easier to spread STDs through anal sex. Condoms can be very effective in preventing the spread of STDs during anal sex, especially HIV. Tip: You may need a little extra lube to account for the extra friction caused by a condom.

5. Fingers, anal plugs, cocks, oh my!

There are many different ways to explore an asshole. If it is your first time, using a finger is a great way to get started without having too much pressure from the tissue stretching. You could start by massaging the other person’s butt, and then slowly work your way to their asshole, gently massaging the outside of it, then slowly inserting one or two fingers to prepare the asshole for a larger object. It is important to know that your asshole does not have an end to it because it directly connects to the large intestine. Once something goes up, it will keep on going. So if you are playing with a toy, make sure it has a flat base so you do not lose it inside the body.

If you have never experienced a butt plug, Good Vibrations has many great, sexy anal toys to meet your pleasures. Start with something small that does not intimidate you or your partner (remember, they need to be able to relax). Read more from Good Vibrations about how to enjoy anal sex here.

6. Um, that funny feeling?

There is often a point in anal play where the sensation becomes very similar to going to the bathroom. This where most people often decide they need to stop because of that fear they just might need to. If you truly believe you need to go, ask your partner to stop and excuse yourself to the bathroom. Often times, this sensation is more the nerves being stimulated and our brains register it as going to the bathroom, because usually that is what is happening in the body when these nerves have stimulation. If you know that a bathroom break is not needed, see if you can relax and go slow, letting the fear wash away. Often, pleasure is right beyond this point.

The asshole has millions of nerve endings that can increase sexual pleasure for both sexes. For women, the nerves are connected to the clitoris, so if you enjoy clitoral stimulation, there is a good chance you will also enjoy anal play. And men have the incredible prostate that can be stimulated.

If you are curious to learn more about how to have pleasurable anal play, check out Charlie Glickman and Aislinn Emirzian’s book The Ultimate Guide to Prostate Pleasure. Even though the title says prostate pleasure, there is lots of great information that is useful for people without a prostate.

Happy exploring!

– Keeley

Featured image by Édouard Henri Avril, 19th c. French artist