why does anybody enjoy this

my boyfriend and i have tried anal twice, once on accident because he pulled out on accident and instead of check which hole to put it into again, he went for it (insanely painful btw) and then we tried it again yesterday but it hurt too much for me to let him go in more than just the tip. we've tried lube and it still hurts terribly, how do people find it enjoyable? how do i make it hurt less?