First things first, get yourself clean. Everyone knows what the butt gets up to when it's not serving you fantastic feelings, and we get it: not everyone's into that. Enter the humble anal douche. Douching isn't necessary in the vagina (in fact, it's really bad for them as it upsets the vagina's natural pH balance and may cause yeast infections), but using a douche anally about half an hour before you play can help ensure a mess-free experience for everyone. Full deets and a walkthrough on using an anal douche over here. Lube is a must for improving all kinds of sexual activity, but it's absolutely essential for butt fun. The anus has NO means of self-lubricating, which means that all kinds of slip and slide needs to come from lubricant. It's best to use a specific anal lubricant with butt plugs since they're designed to last longer and provide more cushioning than non-anal lubes. Start your adventure with exploring and stroking around the anus before inserting anything - your body will be more prepared to accept a finger or a toy once you're relaxed and aroused. You're clean, you're aroused, and you're lubed up. What next? Time to get that plug in that booty! Slowly, though. Start out by inserting just one finger or the very tip of the plug. Listen to your body: this is supposed to be fun, not painful! You may feel a bit of discomfort when you're first inserting anything, but that's okay. Because the anus is usually an exit, it may take a moment for your body to adjust to something coming in. Take a pause, have a big deep breath in and out, and when your body feels ready, keep going.