I've gotten used to masturbating with a buttplug, and if I know I'm going to do anal I'll put my buttplug in beforehand. Sometimes when I'm feeling extra naughty, I'll even wear it to school! Then once I'm actually with a guy, I make sure to get lots of butt-play in when we're fooling around. Rimming is good, even if you aren't going to do anal! And I need to have at least one or two regular orgasms before anal. After that, he eases his cock in and it's smooth sailing from there!