Cleanliness is essential with virtually all forms of this type of play. A bath or a shower is a great primer, and can be the start of the festivities. Once your finger(s) have been inside her anus, don’t put them anywhere else until you wash them. Carelessness in this regard can cause a serious infection.
Without going too close to her anus, explore her inner thighs and bottom with your hands and mouth. Some women have had bad experiences with anal play in their history, mostly because their partner moved much faster, or less gently, than they should have. If this is true in your case, getting her to talk about the topic is a great way to start. By learning where they went wrong, you can prevent that experience from happening again.
Make sure to have a good lubricant, use plenty of it, and start as slowly as possible. Apply a fair amount of lubricant on your finger, and start by making little circles around her anus with a finger. If you feel her clenching her anus, you need to find a way to help her relax, as progressing deeper while she is "tight" will only cause another bad experience. Kissing her on the mouth and all over her body or performing cunnilingus, are just a couple of ways to ease her anxieties. If you get a chance to put on some music and candles ahead of time, it should help her be more comfortable.
Once inside, you can start playing to see what she likes. Start slowly and gently, and make sure to pay attention to her reactions when you speed up and/or add pressure. A few moves to get you started are moving your finger in a circular motion exploring the walls of her rectum, moving in circular motions along a specific region, moving in and out, or rotating your hand to spin your finger. After learning what you can from these techniques, start mixing two, three, or more of them together. Always remember that it is a very sensitive area; so be gentle and watch her reactions before going further.
If your lover is not open to this form of sexual play, don’t force the issue! If your lover refuses, try to open her up to the idea by exploring the area more often with your hands. She’ll slowly get used to being touched around there, and it won’t seem as big of a deal. Ultimately, however, if she says “no,”then accept it graciously and try something else you both like.
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