the things i'm about to say go for kitty cave or booty hole relations for the most part and are things i think people need to be aware of.
first-the first time either way shouldn't involve blood, tearing, or severe pain. booty hole specifically should be a gradual process in which you work your way up from fingers using different kinds of toys along the way.
second- GO SLOW. this is not a race! this is for your pleasure and you should be gentle with your body. sometimes things don't go right. if you find it difficult take a breather and see if more lube helps. which reminds me
third!- LUBE IS YOUR FRIEND (especially for booty hole) if you have never used a toy in either orifice i highly suggest lots of lube and arousal in addition to relaxation. it makes it easier for larger toys to slip inside the smaller holes you're aiming for.
fourth- if you feel uncomfortable STOP! DO NOT PASS GO. DO NOT COLLECT TWO HUNDRED DOLLARS. don't force yourself into doing anything that feels off. if something isn't going in easily DON'T force it! if you're a kitty cave-owning-human and you're having trouble with getting a toy to go in just take slow deep breaths and let the muscles in your pelvis relax, and remember that the toy you are using is there for you to /feel good/ it can't hurt you unless you make it!
now for videos
for the kitty cave owners in the audience-
kitty cave health care basics
hope you enjoy! ^-^