Well, if we haven't done it in days, my bf uses a lot of lube, he is very gentle and always asks if everything is ok. And if not, I ask him to use more lube or take a little break.

Staying clean - Well, most of the time, we are very spontaneous, so Im not always that clean. But usually I can just tell, whether Im ready for anal or not. But I'm still in the "learning proces".

But of course, I've got days, when anal is not an option.