1\ Try Solo Play First
"Your two sphincter muscles are not only essential to anal health but also to pleasure," says O'Reilly. "These ring-like structures control what goes in and out of your butt, so you need to become familiar with their functioning and learn to exercise control over them. When you’re in the shower or touching yourself, try sliding a lubed-up finger inside as gently and slowly as possible, and allow your sphincter muscles to contract and release." This will make you more comfortable—and help you discover what feels best back there.
2\ Breathe Deeply
"Holding your breath interferes with muscle relaxation, which is essential to anal sex," says O'Reilly. "As you breathe deeply, your inner sphincter muscle will relax to facilitate penetration." You may feel like you're in a Lamaze class, but practice your breathing while you're doing the DIY route—so you have a good breathing pattern going when you introduce your partner.
3\ Use Lube
"Most people prefer silicone-based lube for anal sex," says O'Reilly. But no matter what type of slippery stuff you choose, you'll probably want to use something to make anal more pleasurable: "Lube is a non-negotiable when it comes to anal play," says O'Reilly.