How to anal train

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If you have decided to try going in through the back door, there are a few things you have to know first. When having anal sex, it has to be said that preparation is key. You don’t want to hurt yourself while you are trying to have fun, so you need to go about preparing for anal sex carefully.

The guide on this article involves using fingers. You can also use our anal training butt plugs to train your self for anal sex, refer to this guide on how to insert and remove your butt plug. To learn more we also have our butt plug guide, and don't forget this if you're curious on how a butt plug feels.

Starting out

Assuming your rectum is relatively clean, the first step to any anal encounter would be to stretch out your anus. Many people who are just starting out with anal sex dread this step, but it is very simple and painless if done correctly.

The lube

You should have a good quality lube on hand for this step. Find a lube that suits you and doesn’t irritate your anus. Refer to our guide on lubricants to pick out the one that suits you best. Apply the lube to your anus, and to the area directly around it.


Relax your self with your finger

Many people will find it best to start the stretching process by simply rubbing their finger around their anus in a circular motion, like a massage, in order to get accustomed to the feeling.

Get them involved

Lots of couples practice anilingus (rimming, ass licking) before anal sex in order to relax the sphincter and allow the anus to open up. Rubbing your anus with your finger produces a very similar effect to this.

Time to insert your finger

Then, once you are satisfied that your anal massage is done, try slowly inserting a finger, preferably your index or middle finger, just a centimeter up your rectum.

This shouldn’t hurt at all, as you haven’t really touched any of the tricky areas which come after, but it will help you get used to the feeling of having something inside your anus, no matter how shallow. 

Time to get deeper

All these preliminary steps are designed to help loosen up your sphincter in order to get your fingers inside with as little pain and discomfort as possible. So, once you feel ready to proceed, apply light pressure to the narrowing that’s just beyond the 1 cm mark. Your finger should slide in slowly and at an even rate.

Making sure it's all lubed up

It might be a good idea to pull your finger out a few times before you do this step, and then put it back in, so you bring more lube into the cavity itself, rather than just have it around the outside of your anus, where it serves no purpose at all.

Work it

Once you get past the sphincter, release the pressure, and keep the finger in place without moving it much for around a minute or so.

Your sphincter may start to contract and tighten on its own. This is could be due to anxiety, but you should focus on releasing it consciously. It is advised that you push out with your rectum while you do this, as though you were having a bowel movement. Remember, your finger and your sphincter must work in synchronization.

When you are used to having a finger up your rectum, and the muscles of your sphincter are fairly loosened up, you can push your finger further up the rectum, into an opening just beyond the sphincter.

This shouldn’t hurt at all, in fact you shouldn’t be able to feel it, unless you’re rubbing your prostate, or the other side of the vaginal wall. Go around the opening and feel it out with your finger, just so you know how much space there is in there.

Repeat with two fingers

Once this is done, carefully and slowly remove your finger, making sure that the sphincter does not clench up while you’re doing it. Now the procedure is repeated, but with two fingers.

You can use either your index and middle finger, or your middle finger and ring finger, whichever feels better for you.  Start pushing them in slowly, with even pressure, and at a continuous rate, just like before.

Try to hold them together firmly, so they don’t change positions relative to each other, as the point of this step is to start stretching your anus enough to take a penis or penis-sized toy.

When they have passed through the sphincter and into the opening, wiggle your fingers around in there a little bit. This should feel quite good, and help prepare you for the feeling of being completely filled afterwards.

Repeat with three fingers and you're ready

For some people, this will be the final step. However, it is recommended that you try to repeat this with three fingers as well, especially if you are going to have anal sex with a penis or a penis-shaped sex toy right afterwards. If three fingers are too much, and you feel pain and discomfort, go back to two fingers, and try again later.