Mar 8, - requires comfort and patience. The best way to prepare for pleasurable anal sex is through anal masturbation. Here's a step by step how to guide. Rear view of man and woman; butt acne. Photo: Maskot / Getty Images. Dec 16, - This is the first in a multi-part series from After Hours about anal play. Your asshole does not self-lubricate the way a vagina does, so you.