This is my how-to on enjoying anal sex.
If you can't tell from my stories, I have a bit of a thing for anal. I love it, I love reading about it and I love doing it. And I think it's quite possible for EVERYONE to love doing it!
The first step is to work your way up to it. I wouldn't suggest going into your first time of anal without having had at LEAST a finger back there. The best thing to do is get plenty of lube, have your lover put one finger in... work it back and forth a little to loosen things up. When you're ready let them know and they'll slide a second finger in. At any point that you feel like you need more lube, make sure you tell them! Personally, I like a little pain with my pleasure, but I do realize that not everyone feels that way.
My feeling is that the person who is taking it needs to be the one in control for the most part. While I do write stories where the guy just slides right in and it's all heavenly... I found this to not be true UNLESS you're used to anal. In which case it is QUITE heavenly. But, when you haven't done it in awhile (or ever before) make sure the person taking it is in control. This doesn't necessarily mean on top. I like it best in the doggy position, so what that means is that he stands behind me and I moved back and forth.
Go back until it hurts, move off it a little... go back again... hey doesn't feel so bad that time... hold it, move off, go back, starting to feel pretty good... push a little more in. Do this until it's all the way in. Reapply more lube if you need to during the process. And do try to make sure that you've had something in there before you stick his dick in, although fingers are not as long or as thick as a dick they help immensely.