I really want to try anal with my bf, and he rims me and stimulates it, but has never had intercourse that way. When we first started having sex, he accidentally hit the wrong hole in doggy style and it hurt like hell and he felt horrible about it. But that was several months ago and just getting comfortable with each other, and we were in the backseat of a car XD. So i need to know how do i get confident enough to ask him, PLUS, without dildos or anything like that, how do i make sure it won’t be suuuper painful???? thx so much