Lube. It’s important to note that you’ll need to keep adding more lube throughout the process. "Anytime what you’re doing feels uncomfortable, the first thing to do is slow down,” Silverbeg states. "Then, add more lube. Be sure to choose a lubricant that’s good for anal sex, which means it will be long-lasting, thicker, and contain no desensitizing ingredients.”
Time. Simply put, take your time when it comes to exploring your backside — your bottom isn’t going anywhere! The anus — and the sphincter muscles in particular — need time to not only relax, but get used to a new kind of stimulation. They’re not used to having things enter, after all.
Privacy. Make sure you have plenty of privacy the first few times you engage in a solo session. This way, you can focus on the sensations you’re feeling and not on when your roommate is coming home. "Don’t rush to anal penetration the first time you try anal masturbation,” Silverbeg suggests. “Take your time and build up to it even over a few sessions."