The simple rule to remember is CLR - Communication, Lubrication, Relaxation. A tonne of each, and then some.
You have to WANT it. You have to be turned on, excited, really into it. It's ok to spend heaps of time on foreplay, y'know...
Practice by yourself. It's your butt, you need to familiarise yourself with it first, before letting someone else in there. Play with it, see what you like. With your own fingers, you have a better sense of what's going on that you do with someone else's. And y'know what? You don't have to take a whole fist up there immediately. Maybe just a finger to start with. It doesn't even have to penetrate. Just playing around with the opening can feel GREAT. Then move up to a finger inserted, and when you're comfortable with a finger up there, start moving it around a bit. Feel the texture, feel the sensations of something moving around there. Move your finger in and out, twist it around.... in short, experiment. Once you're happy and comfortable with 1 finger, introduce another. And get used to that.
Toys are great, too. Particularly butt-plugs - start with a small one, and when you're comfortable move up to a medium etc etc.
So basically, best way to play with your butt is slowly, with plenty of lube, and when you're in the right zone mentally.
Have fun, post pics and tell us all about it!!
