Anal Tips

So, my SO and I have slowly been making our way to anal. Both of us were weirded out by the topic, but now we're somewhat eager to try it. The most we've done is 2 fingers in the booty - which felt amazing, but I find that I can only really enjoy it if I'm either tipsy or drunk. Nevertheless, I know I need to get more comfortable with the idea before I dive into it, but do any of you have any tips or experiences you'd like to share for first time booty sex?