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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 stimulating his prostate 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!
