The Ultimate Step-By-Step Beginner's Guide to Anal Sex


Beginner's Guide to Anal Sex. Watch our sex expert Angela's video and keep reading for our best anal toys and lubes

Have you been considering having anal sex with your partner? Are either of you new to anal play? You are likely excited, nervous, and even a little bit afraid. These are all very natural reactions about having anal sex for the first time! You’ve heard it can be amazing, but it might be something new for either one or both of you.

Having anal sex is different from other types of sex in several ways, but it really is all about pleasure and orgasm too. And yes, you can orgasm from anal sex. Because the anus has many nerve endings, some of which are attached to the genitals, it means you can definitely have an orgasm practicing anal sex. And anal sex doesn’t have to mean penetration with a penis, it can also include fingers, toys, and tongues.

Communication is key with all types of sex, but especially anal sex. It’s important to talk to a partner about what feels great and what doesn’t feel so great. That and going slowly will ensure it’s a pleasurable experience for both partners are most important.

If you have done what most people do when something is new to them and Googled anal sex, specifically, “does anal sex hurt,” you have most likely read a lot of horror stories. Well, let me the bearer of GREAT news - none of them will happen if you follow these important anal sex rules. If you’re having pain, you’re not doing it right. Follow these steps to ensure anal sex is enjoyable for both of you!

1. Make Sure You're Ready

Just like with any sexual activity, you need to make sure you are honestly ready for it. No sexual activity should ever be embarked upon because you feel pressured, or because you think you will lose a partner if you do not. So, evaluate your feelings on this and make sure that you try it because you want to and you’re ready and excited to try.

Another thing you should prepare yourself for is the possibility of encountering a little poop sometimes. It goes with the territory. Sometimes there might be some poop stuck in the anal canal while you’re having anal sex. Some people prepare and clean out prior to anal sex, while others do not. Just be prepared to clean up and continue or have a good laugh because sometimes, poop does happen.

Silicone Jeweled Anal Plug

Silicone butt plug with decorative jewel

This Silicone Jeweled Anal Plug is available in 3 different sizes to suit different experience levels! You can insert one during masturbation or foreplay to help prepare your body for anal sex.

2. Trust Your Partner

Again, just like with any sexual activity you have to be able to trust your partner. With anal sex, specifically, you really need to trust your partner. You have to make sure that they are willing to take their time, listen to your bodily cues, stop if you need him to stop. Anal sex is not something that can or should be rushed. Anal tissue is very delicate and if you rush it, you could tear it, which leaves it open to infection. Anal sex takes patience and time when you first begin.

Tell your partner if it hurts, if they are going too quickly, and also tell them what feels good. Learning together what works for each of you is important to enjoying the anal sex experience. Trust and communication are key.

3. Train With Butt Plugs to Make Things Easier

Sometimes in order for anal sex to go more smoothly, a little preparation is advisable. Many people new to anal sex start with anal training sets like the one shown in the video above. These are toy sets that come with butt plugs in different sizes that slowly train your anus to accept anal penetration. The butt plugs come in small, medium, and large sizes so that you will eventually be comfortable accepting a penis. It’s also a good way to know if anal penetration feels good to you.

Anal plugs are a great way to gently open up the anal canal in preparation for anal sex. Find a small-sized plug, use a lot of lube, have your partner gently push the plug in, and then go on with foreplay getting your partner very excited. Remove the plug before anal sex is attempted – use more lube – and follow the other steps until penetration is achieved.

Make sure the anal plug has a tapered end or a ring so that it doesn’t get sucked up into the anal canal without a way of retrieving it. No embarrassing visits to the ER please! Preparing for anal sex with anal training toys is a great way to not only learn if you enjoy anal penetration but it’s also a great way to get your anus used to stretching.

Silicone Anal Plug - Provides Tantalizing Stimulations!

Tapered silicone butt plug with looped base

This tapered Silicone Anal Plug has an easy-pull loop in the base that makes this toy safe and easy to remove.

4. Use Lube

Lube, lube, lube, and more lube. Good quality, long-lasting lube. Lots of lube. Hey, did I say lube? Listen, the anal canal is not self-lubricating and, in fact, is quite dry and fragile. This means if you do not introduce lubrication to the anal party you stand the chance of tearing the sensitive lining, causing pain, and having a natural drag that is unpleasant to both of you. It’s best to use lots of lube to keep things moving along.

If you begin with an anal training set or toys, be sure to use a lubricant that is compatible with your toys. Silicone lube used with silicone toys will degrade the toy over time, so if you have silicone toys, use water-based lube. If you are just doing penetration with a penis, lots of people prefer silicone-based lube.

Lubing both the anus as well as whatever is penetrating it is important. So be sure to lube it UP! And remember, always lube anything that has come out of the anus that you want to insert again. Use lube liberally to keep things going smoothly.

5. Slow And Steady Wins The Race

I am sure you are both excited! The tendency to push in fast and furious is tempting, but you need to realize that it takes time to work the penis (or toy) into the anal canal.

The canal will stretch to accept the penetrating object, but it doesn’t happen instantly. With lubrication and patience, the canal will open. Furthermore, as an exit-only orifice, it takes time to train the muscles to relax and accept the insertion. Just a little bit at a time – inch by inch – and once it is all the way in, then you can speed the pace.

Tapered Anal Beads - Extremely Flexible!

Silicone anal beads with tapered tip

Try using a toy with a beaded shape like these Tapered Anal Beads. These flexible silicone anal beads have a tapered tip and you can insert just one bead at a time and move up to the larger beads when you're ready!

6. Push Out To Get It In

First-timers do not understand this very important trick which will make anal much more pleasant. When your partner is trying to push IN – you push OUT. Yeah, you heard me. When we are trying to open the anal canal to accept the inserting object it works best to push out (like you are having a bowel movement) and this relaxes the anal muscles, allowing insertion to go much more smoothly!

So, when the tendency is to pinch and tighten the muscles, you need to follow the reverse and push OUT. Don’t go crazy, but you have to have the feeling of pushing out a little bit, so the muscles are more relaxed. Having relaxed anal muscles will make penetration easier and more pleasurable for both partners. It sounds weird, but it really does work.

7. If It Hurts - Stop

The chance that you will have some pain or at very least discomfort with anal sex is pretty high. If you follow the above steps then the likelihood of any real pain is very minimal, however, if you do experience pain – STOP right away and make adjustments.

If you experience pain, ask your partner to stop – hold still – and wait for the pain to pass. You can add a little more lubricant while you are waiting and then start slowly again. If you can’t get the pain to stop, then you should stop and try again another day. The saying ‘no pain, no gain’ does NOT apply to anal sex. Pain is a major indicator that things need to slow down or stop.

Things to Remember

If you penetrate your partner anally with your penis or toys, do not then penetrate vaginally without cleaning the penis or toys. Going from anal to vaginal sex without cleaning off allows bacteria from the anal canal to enter the vagina which can lead to infections. Always wash off before re-entering the vagina or having oral sex.

Communication and consent on both sides are important in any relationship. Make sure you both are communicating about what feels good and going slowly.  

Anal sex done correctly should not bring pain. Any pain means you need to stop immediately and try again or stop the session if it continues.

Have You Ever Used Anal Toys? Let Us Know In The Comments!


  • M

    I am really curious about doing anal. It will be my first time. I’m pretty excited about it. I have heard many horror stories about it but I’ve also heard great amazing orgasms stories about it too and I think the pros outweigh the cons. But I see it’s something that you need to be comfortable with and I think I’m ready to experience it.

  • Sara

    I’m new at anal and I wanted to know when the feeling of having to go will stop. I experience anal about 3 days ago.

  • Melanie

    I’ve had a couple really unconscious experiences with anal and then some ok, until omg, a bigger, but better lover came along and wow, he knew what to do and I’m in live with it! Gentle I’d important until it isn’t anymore!

  • Jerkman

    Nancy you just have to go slow and use a lot of lub trust me you will stretch then you can have fun.

  • Jerkman

    Well Dickie I wish I was there to help you have more fun.

Leave a comment

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.