Sex Elite Anal Log:
Fingering the Anus

Before fingering the anus, make sure your fingernails are trimmed tight and you have the proper lubrication. A little spit is better than nothing. You can use any finger you like, but the difference in size (except for the thumb) is not as great as you'd imagine. You're better off using a finger that you're comfortable controlling, rather than starting with a pinky. You can use many of the same techniques that you would during analingus to finger the anus. The most popular are detailed below.

Circling the Rim: Probably the tamest and easiest anal sex technique to introduce someone to anal sex is to start on the outside and slowly work your way in. Use one finger to gently circle the outer rim of the anus. A little lube is helpful here, especially if you want to lead up to some actual insertion.
Ringing the Bell: Take one finger and push on the anus, as though you were ringing a doorbell. Hold each push down for a second or two before releasing.
Thrusting: Again, make sure your finger is properly lubed, then start slowly inserting a little bit at a time into the anus. Move in and out with a thrusting motion, similar to penetration during sex.
Multiple Fingers: For the anal expert, you may be able to get two, three or even more fingers into the anus. Try wiggling your fingers in different directions once they're inside!