Analingus and Anal Fingering

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.
Getting Started
Some men are not very open to experimentation with this body part, as enjoying it may make them question their sexuality. As stupid 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. If your partner refuses, don’t force him, but try to open him up to the idea by exploring the area more often with your hands. He’ll slowly get used to being touched around there, and it won’t seem as big of a deal. And remember, by stimulating the prostate gland as he gets close to climaxing, you can give him an orgasm three or more times as intense!
Cleanliness is essential with virtually all forms of this form 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 his 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, and start as slowly as possible the first few times.
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.
Fingering
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. The most effective use of anal play is definitely 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.
Analingus
Before engaging in analingus, make sure to thoroughly wash the area. Once clean, licking this area of the body is virtually no different then licking any other, and can be very stimulating for your partner. Like other play in this area, don’t just jump right in, build up to them and allow for your partner to get comfortable. A great way to start performing analingus is to move into it when you are performing fellatio. The area is really sensitive, so run your tongue around in circular motions, use your tongue to tickle, and when you are both ready for it, even to penetrate.
Access to his anus is a little tougher than to his penis, but there are several positions that are ideal; lying on his back with a large pillow to arch his bum up, him bent over with legs spread, him standing with you kneeling, and him upside down with his legs spread

Anal Intercourse
Anal sex is quite a different ball game than using your finger. Even if he enjoys and requests you to pleasure him there, he may be apprehensive about putting something so large as a dildo in there. The keys to success are sufficient (i.e. copious amounts of) lubrication, relaxation on his part, and a slow, gentle approach. Let him tell you when he wants it harder or faster and don't be shy about playing with his penis at the same time. For more on this please see the Anal Intercourse section.
Anal Toys
Butt Plugs
A butt plug is a toy that is inserted in the rectum. Once inserted, you can leave it where it is or move it in and out. Many people enjoy the sense of fullness that butt plugs bring, much in the same way women enjoy the fullness experienced during vaginal sex. Others enjoy the sensation of inserting something in their anus.
Butt plugs come in many different shapes and sizes. Some of the sizes seem silly, but some people are obsessed with larger toys, so the companies willingly accommodate. The most popular plugs are less than an inch in diameter, and roughly 4 inches long.
Climax Beads
Beads are some of the most popular anal toys. They range from soft to firm-textured, usually consist of four to ten balls connected with a piece of nylon cord or plastic/rubber, and there are a wide selection in ball sizes. Whichever type you are interested in, they are virtually the best toys to ease into anal play.
Climax beads are a very simple toy to use. After being covered by lubricant, they are inserted into the anus bead by bead. Most people then leave the beads where they are until near the point of orgasm, at which time the beads are pulled out one by one. This can greatly intensify an orgasm to the point that it is too intense to handle. We suggest starting with smaller balls, and then moving up, as you get more experienced.
And like everything else involved with anal play, cleanliness is of the highest importance. Make sure to clean your toy thoroughly after using it, store it in a dry dust free place, and be very gentle when starting out.