Thanks for the advice! And oh yes,always fun to watch heheSex and the Kitty wrote:
You're probably tired of hearing it but ... use lots of lube! For real, dude. It's super helpful.
As most others have said, just start small with your fingers and really work things until she's ready. It'll probably hurt a little the first time. Just go REALLY SLOWLY and keep checking in with her to make sure she's doing alright, giving the OK to go forward, etc.
I'd say start with a toy first and let her use it on herself. It'll make it easier because she can control exactly how fast it goes and how deep, etc. It'll also be hot to watch her ;)
If it's safe for vaginal then it'll be safe for anal - the only real difference is that anal lubes tend to be thicker due to the 'mechanics' of it all (so the dedicated lube may not be as suitable)