Tips for anal masturbation?

Fair warning, I have aboslutely 0 experience with anal masturbation, (kinda the same goes for gay experiences in general, I just came out as bisexual a few months ago, and I still have to get the courage needed to go to a gay bar) so I wanted to know if there were some thing to make everything smoother. I also have a good amount of extra money to spend, so I can get a few toys if needed.