Well, we don't really plan ahead for it like that, it tends to be more spontaneous! All I can really suggest is that you may want to be sure you've had a dump that day before you do it...
It can leave your hole a bit sore for a few hours afterwards, not seriously so but you will feel it. So every night may not be the best idea! I'm sure it varies from individual to individual, so it's really up to you to try it and see how it feels for you personally. Like most things, I imagine you get better at it, and less sore, with more practice...
Thanks, now do you know what your wife does to ensure there is nothing in the anus before having sex? (I mean, stuff does come out of that hole..how do I make sure none of that is there?) My husband would have us do this every night if he could...but everything I have seen at the pharmacy says you can't use it that often! :)
Well, first off, anal sex won't give you AIDS unless the person you are having it with has AIDS, and I'm assuming you already trust that your husband doesn't - so this isn't a problem.
As for other health issues, the main thing is not to have anal sex and then move back to vaginal (or oral for that matter!), at least not without cleaning the penis well, so you don't introduce germs where they shouldn't be going. I have heard that you shouldn't go directly from vaginal to anal without cleaning either, for fear of introducing a yeast infection to the anus, but that's never troubled my wife and me yet...
Yes, anal sex can be fun, and feel good, for both partners. Not everyone enjoys it, but plenty do.
As for how - first up, use plenty of lube (preferably a specific lube such as KY jelly, available on the shelf of all chemists shops), since the anus does not produce the natural lubrication the vagina does. You need to relax. "Doggy" position is probably best for your first try. Probably best to start with a lubed finger, that will help open up the hole and let you feel what it's like to have something inserted. With the penis, he should start by going in bit by bit, not all at once in one big shove, then increase depth with each stroke.
If you get adventurous you could try putting a vibrator in the vagina at the same time - that feels great for both parties...