If your partner is not open to this form of sexual play, don't force the issue! If your partner refuses, try to open them up to the idea by exploring the area more often with your hands. They'll slowly get used to being touched around there, and it won't seem as big of a deal. But ultimately if your partner says "no", then accept it graciously and try something else you both like!
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) or Sex Toy has been inside their anus, don't put them anywhere else until you wash them. Carelessness in this regard can cause a very serious infection. Make sure to have a good lubricant, use plenty of it, and start as slowly as possible the first few times. Assess their responses to your actions and react accordingly.
Be sure to clip your fingernails quite short before doing any type of penetration, especially anal. The lining of the rectum is thin, and can be torn by sharp objects. If you have longer fingernails, you can pack some cotton balls around your fingernails and put on a latex glove. Also, if you are paranoid about what could be on your finger when you pull it out, a regular or finger Condom may be a good idea.
Some men are not very open to experimentation with this body part, as enjoying it may make them question their sexuality. As ridiculous as this may sound, it is a result of the prejudice and lack of understanding in today's society. In any event, make sure to communicate with your partner to avoid bad reactions.
Once you get lubricated, you want to start by taking it really easy. Most people who have never had any anal play will tense their sphincter muscles. If they are tensing, do not try to push through, as it will cause a lot of pain and discomfort. Instead, make little circles around his anus and wait for him to relax. Once he starts relaxing, gently try moving your finger in and out a little. Start shallow and slowly move deeper, just make sure to watch his reactions and facial expressions to see if you are going too fast.
Once you get inside, you can do a variety of things, including: twisting your hand, pulling in and out, moving in large circles following the wall of the cavity, or stimulate specific spots with little circles. There are two very pleasurable spots in and around a man's anus. The first location is the anus itself; it is surrounded by a large number of nerve bundles and is very sensitive. The second is the prostate gland; it is located a few inches inside the anus towards the belly button, and often feels like a firm bulge.
The most effective use of anal play is right at Orgasm. If you have a finger inside, giving him Prostate Gland Stimulation, when he reaches an orgasm you will send him to another world of pleasure, one that he will most likely be asking you to help him revisit. By stimulating the prostate gland as he gets close to climaxing, you can give him an orgasm three or more times as intense!
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.
Using her natural vaginal lubricant or saliva may work, but we strongly recommend that you use lubricant, especially the first few times. 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, performing Cunnilingus, are just a few 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 softly, and make sure to pay attention to her reactions when you speed up and/or add pressure. A few basic techniques to get you started are move your finger in a circular motion exploring the walls of her rectum, moving in circular motions along a specific region, moving in and out, rotating your hand to spin your finger. After learning what you can from these techniques, start mixing two, three or more of them together. Just always remember that it is a very sensitive area; so be gentle and watch her reactions before going further.