Curiosity and anal.

One night I was pretty drunk and I brought up anal to my SO.. he doesn't drink so we ended up not doing anything. He brought it up the next day- I was very embarrassed. But I was and am very curious about it.. I've read good and bad stories. I know lube will be my best friend.

But how do you even begin?

How do you go about cleaning up?

Do you recommend using a condom?

My SO pulls out so will that hurt doing anal?