Help. The topic is: Anal🙄🙄

My boyfriend insists on trying it. And I mean every time we have sex he messes around with his fingers but until here recently we haven't tried actually having sex with THAT hole. We tried it doggy style and oh my lord it huuuurt. Even with a little lube. Any tips to make it easier? Because I do want to try it positively 😂🙏🏼