Curious

So I have tried anal sex a few times with my ex and it was always painful except this one time when I was a bit liquored up. I still want to try it and I'm curious about it because I love getting my ass licked, stimulated and to be honest I sometimes feel like I want someone to give it to me from behind. However, I'm also scared shitless if it being painful and I'm also freaked out about the mess it may make. I'm a clean freak and the thought is just so nasty to me. Should I start using anal plugs and beads? Help me with suggestions and tips please.