Condom Use
Condoms are another necessity. Enemas, douches and other cleaners will not be able to get all the germs and bacteria out of the rectum. Not only is anal sex facilitate the transmission of STDs better than any other form of sex, it can also cause urinary tract infections and other bacterial diseases. Latex protection is essential, and can offer additional slickness. If your partner is not 100% familiar and safe you should by all means use a condom. Many couples use one during anal sex regardless of how much they know each other.

Finger Insertion

Postillioning is inserting a finger(s) into the anus, and may include massaging it and the rectum. The index or middle finger is best used, being long and strong. The finger must be well lubricated with spit or oil or lubricant (don't use any thing with soap, this will have an enema effect), and then placed at the anal opening. The outside can be caressed in circles and mild probes. You can trace warm wet rings around the outside of the anus. This is usually a very warm experience and helps relax the area. Make insertion by pressing gently and firmly inwards, wobbling the tip of your finger a little as necessary. 

After inserting a finger you can massage by pressing outward in a circle, tensing and calming it, trying to curl your finger around its side, feeling its touch through the skin. While you’re being explored push out, like you are going to take a shit, this will intensify the feeling.

Once inside feel the thick, strong, muscular ring which is the anus and beyond it the soft sides of the rectum. Keep your fingertip beyond the anus, or contraction of the muscle will cause the finger to pop out. Once your finger is inside you can explore around, pushing it in as far as it will go, curling it around the anus, flicking it back and forth.  Next you can insert two (or more) fingers, seeing how far you can bend them apart. Push them apart inside as a way to stretch and loosen the anus. Just having the finger(s) positioned inside while sucking on her clit or fingering her pussy can be very orgasmic. Sliding them up and down in her ass at orgasm can double or quadruple the intensity of the orgasm.

Extreme finger fucking can become fist fucking, which is insertion of the whole hand while rapidly thrusting your fist and arm into the anus.

Once you have successfully penetrated with a finger a number of times then you can move towards something that is a bit larger. Practice stretching, tensing and calming your anus around the finger until it can be widened easily and painlessly.

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