To get ready for anal sex, the first thing the receiver needs to do is relax. A hot bath or a massage beforehand is always a good idea to get prepared. The sphincter muscles around the anus won't let anything pass comfortably unless they're relaxed.
Discuss the limits, expectations and techniques of your anal experience beforehand. There's nothing worse than surprises during anal sex. Make sure you and your partner are on the same page every step of the way.
It's a good idea to have a bowel movement about an hour before anal sex, to make sure you don't run into anything you don't want to. You should also bathe the area, to remove any traces left by regular wiping. An enema is nice - and very thorough - but is not necessary for clean anal sex
Start Slowly
Because there is a very fine line between pain and pleasure during anal sex, we suggest that you begin your anal explorations very slowly and proceed at a leisurely pace that will allow to experience and appreciate each level of insertion.
It's a good idea to start with some external stimulation, either using a finger or with a little analingus. Make sure you have plenty of lubrication, as even the slightest bit of dryness can cause a very painful snag.
Begin insertion by using a finger or other small object. Proceed little by little, carefully watching the reaction of the receiver. Do everything you can to keep it pleasurable. You may find that it will take several sessions before you can even proceed to anything more than a finger.
Once you proceed to something bigger (ie., a penis, dildo or butt plug), you'll need to revisit the lubrication issue and be even more careful with the speed. The key for the receiver is to relax the anus and the sphincter - breathing outward during insertion can help quite a bit here. The more the receiver relaxes, the easier insertion is. As the giver, ease each little bit in and slowly withdraw until the receiver can handle normal sexual