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Something to be careful about:
*If the person on the receiving end of anal sex is reluctant in any way, it is best to skip out on the whole experience. Not only will he/she have a hard time relaxing, but he/she will almost undoubtably not enjoy the experience. If the partner is reluctant, please remember that his/her toosh is part of his or her own body, and you must respect any choice they make that affects the body.
This situation is most popular in male/female relationships, and I blame porn. I think a lot of guys look at porn and think "Wow, those girls like it! My girlfriend will too!" But as Aladdin Sane said, everybody is different, and some bodies just can not handle items inserted rectally.
To be more on topic:
I have heard that inserting a very well lubricated pinky into the rectum while a girl is having an orgasm will open her up to the idea of anal sex.
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