Relax
The key to anal sex...you need to relax. Open your mind and release your tension and stress. Try taking a hot bath or go for a massage, do some light stretching and clear your mind. Keep in mind the sphincter muscles around the anus won't let anything pass comfortably unless they are relaxed. If you can relax you may find out of this world erotic pleasures you never thought could exist.

Starting Out Slowly
Slow is the key word. With anal sex there is a fine line between painful and pleasurable sex. In order to make this a pleasurable experience we suggest that you begin your anal explorations slowly. After you discover what is pleasurable to your partner and where they like to be touched you will be able to move at a comfortable speed for the two of you. Remember, teasing and anticipation can be very erotic. When you begin make sure you have plenty of lubrication (you can not over lubricate when it comes to anal sex). The slightest bit of dryness can cause pain. There are many delicate nerve endings in this area. Drop a few drops of lubrication on your finger and gently massage the outer portion of the anus. This will help your partner relax. After a few moments begin to gently apply pressure on the sphincter muscle. If you are not comfortable using your finger, we would suggest a slender plug or slender probe. Again, apply lubrication to the anus area and the plug/probe. Using a smaller "toy" will help you feel the muscles contract and relax as you apply pressure.

Exploration
Proceed little by little, carefully watching the reaction of the receiver. The idea is for the receiver to relax the anus and sphincter muscles. To help assist in relaxing these muscles the receiver can breath outward during insertion. As the giver, ease each little bit in and slowly withdraw until the receiver can handle the normal and pleasurable pumping action. You may find that it will take several sessions before you can even proceed to anything more than a finger. Here is a good time to take a look at the anatomy of the anus. As you begin to become more advanced it is a good idea to understand where the G-Spots of your partner are located. Applying slight pressure to these areas will achieve orgasmic feelings for your partner.

Once you proceed to something bigger i.e., a penis, dildo or butt plug, you'll need to revisit the lubrication issue, make sure your partner is comfortable and not feeling pain. From here you can go on to selecting a toy that is right for your personal pleasure.