Anal?

My boyfriend and I have been together for over a year and everything is wonderful. We enjoy fooling around and having sex (with a condom). He brought up anal to me and we have tried it once but it was absolutely horrible for me. I told him it was very painful for me and he said he was sorry and he wouldn't do it again. He says he's not interested in anal anymore, but I think he just doesn't want to hurt me. Any tips on how to make it feel good for me? Or will it never really feel as great as vaginal sex?