Well considering its male/male then I don't know for sure about the pain. There are many threads on anal sex and how to prepare yourself... main things are to "relax" and have plenty of lube!
Having had anal sex once or twice I know that yes plenty of lube is important... and taking it very slow... no need to rush! for me it hurt at first but once it was in.. I was ok.
As far as knowing if u are ready? I mean if you feel comfortable w/ that person and feel ready to share something intimate w/ them... then I think its ok... have you guys done other stuff to each other? If not whether male or female.. no need to jump right into intercourse.. can always enjoy oral or mutual masturbation.. etc.
Good Luck!
