So this weekend, I (21 female) am trying anal with my boyfriend. I have done research on anal; taking it easy, using lots of lube, using condoms, having an orgasm before hand to relax, etc. Even though I've done research, I still have questions about a few things. I got a set of three butt plugs that are different sizes for anal prep, and I don't know how to start. I tried the smallest one a few weeks ago and it felt weird. How do I use butt plugs? Also how do you even shave your butt crack? It's very hard to shave there since I cannot see. Any other tips and advice would be great as well!

For context: I haven't had anal with anyone besides myself. I used to love anal play until a couple years ago when one time, it went badly and it hasn't been the same since. I would like to get back into it because it feels good.