Bottoming will hurt at first, but it shouldn't tear or bleed, at best it's minor discomfort because the hole isn't used to having a thing inside, the muscle will tense up for both genders, preparation would help, but you aren't gonna avoid that little pain at first.
For women, it slides easier than with a guy, the front is easier than the back, if you ever wanna do it I suggest going for the front at first, and ofc no roughness at first or else you will bleed, overall the pain is meh like I said its minor discomfort if your prepared well.
try using sex toys first before doing it w someone. experiment w diff sizes and types of stimulation. helps u to know what and how you like it.
in my case, vaginal penetration is hundred times enjoyable for me than anal. the latter is a bit tedious and hurts more for me even w enough lubrication. i often feel sore near the opening and my tailbone after it

This is a question so Anybody out there who are sexually active, I wanna ask. Does it hurt? After doing it once do you want to do it again?
I just want to know because someday I want to experience how you experienced it YK? It's for future reference (๑•ㅂ•)و✧