Anal Fingering & Analingus

Before you start poking around her backside, make sure that your partner is ok with it. Some women are not, and won’t react gently when they feel an “intruder”. If you want to try, but your partner doesn’t, don’t try to force them to do it. You have a much better chance that she will try to do it if you have her cooperation, rather than arguing with you. Bring the topic up gently on occasion, and help her open up to this experience by getting her comfortable in the area and with the idea.
Without going too close to her anus, explore her inner thighs and bum 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.
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), penis, or sex toy has been inside her anus, don't put it anywhere else until you wash it. Carelessness in this regard can cause a very serious infection.
Make sure to use a good lubricant (and plenty of it!), and start as slowly as possible the first few times. Assess her responses to your actions and react accordingly
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 it and allow for your partner to get comfortable. A great way to start performing analingus is to move into it when you are performing cunnilingus. 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 her anus is a little tougher then to her vagina, but there are several positions that are ideal; lying on her back with a large pillow to arch her bum up, her sitting on your face, her bent over with legs spread, lying on her back pulling her legs back, and her upside down with her legs spread.
Anal Fingering
Using her natural vaginal lubricant or salvia may work, but we strongly recommend that you use lubricant, especially the first few times. 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. 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 bum, 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.
Anal Intercourse
Anal sex is quite a different ball game than using your finger. Even if she does enjoy your finger pleasuring her there, she may be apprehensive about putting something so large as your penis in there. The keys to success are; plenty of lubrication, relaxation on her part, and a slow, gentle approach. Let her tell you when she wants it harder or faster and don't be shy about playing with her vagina at the same time. .
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.