Okay, anal. Do you enjoy it? Why or why not?

My boyfriend & I have been together 2 years, he's always begging for it. So I told him he could try tonight but go slow. Which he did. He barely got the head in and I was hurting. So I told him to stop. Then I breathed a bit and we tried again. Then he went inch by inch. He finally got all the way in and one stroke I was DONE. like I was crying in pain. Real tears. He felt like a total asshole. Hahaa! I reassured him it was okay and we can try again another time. Anyways, will it always be like this?! I want him to enjoy it, but I want to enjoy it too. HELPPPPP.

P.S.

we used a ton of lube