“I would like to try anal sex, but I am unsure how to go about it. What can I do to ease into it?” -Anonymous
Go slow! This is the big thing to keep in mind for both partners after deciding to try anal sex. Going slow makes both people more comfortable and relaxed. It also helps reduce pain for the person receiving anal- and yes, there most likely will be pain. How much will depend on the person and process, and neither should be rushed. Because anal sex should be pleasurable, it is beneficial to do “the prep” during vaginal intercourse. It’s more relaxing and fun.
Because the anus does not create its own, the first thing you will need is water-based lube. Use it generously. The walls of the anus are thin and fragile and can tear easily. There are numbing types of lube, but I don’t think they are right for everyone, especially beginners. Pain tells you if something is wrong, and if the area is numb, you might not get the message.
Condoms are also necessary. STIs can be transmitted more easily through anal intercourse, and condoms with additional lube reduce the risks.
Get comfortable having your anus touched. Do this during sexual arousal. Have your partner massage your buttocks, then slide fingers down or around the middle crack a few times. Lightly touch the anal opening and circle it with a well-lubed finger, eventually massaging with light pressure. You can do this for as many sexual “sessions” as you need.
The next step would be getting the anus used to penetration. Using one finger (lubed), slide it in and gently circle it around the opening. Once this is comfortable, try two fingers.
There are also toys that could help you get used to penetration. Butt plugs are designed for the anus (as I’m sure you guessed by the name) and could be used after or instead of inserting fingers (again, lubed). If a plug is used instead of fingers the person receiving anal could guide their partner on pressure. It could also be used during vaginal intercourse and before inserting the penis in the anus.
When you are finally ready to insert the penis, pick a position you feel comfortable in. There are three that come to mind for beginners: doggy style, missionary, or woman on top.
In missionary, legs go back to your chest with feet on his chest, shoulders or around him to lift the pelvic area. This position gives him more control, while doggy or on top allow you to control the pressure more or completely.
Make sure a condom and lots of lube are used. Thrusting should not be fast to avoid tearing the walls of the anus or the condom.
The first time may be uncomfortable or painful, and if you don’t want to try it again, don’t. However, it may get better with practice.