It depends on you, your partner, and how you're feeling. Anal can feel fantastic, it can feel "funny," it can be completely neutral, or (if done wrong) it can hurt.

Using plenty of lube, having enough warm-up time, spending plenty of time learning to relax, and having two people (you and your partner) who you can trust to hold back or call it off if necessary will prevent it hurting.

In order for it to feel good you have to take time to become familiar with the sensations and separating them from "going to the bathroom" so they can become pleasurable (often we train ourselves to process anal sensations as being somewhat dirty/unpleasant). You should also be sexually excited for best results. Some people may not be wired to be able to feel the pleasure of buttplay, but it's worth a try.

It supposed to feel arousing and pleasant. If it is painful, then one isn't prepared, isn't using enough lube, isn't relaxed enough or hasn't had enough preparation or maybe doesn't want it.

What would be the point if it was "supposed" to hurt? If done right, it doesn't hurt and is very arousing.

agreed.