@Belle1x12,
So you like something but don't want to pressure him into doing something you think he might not like. It seems he likes something but doesn't want to pressure you into doing something he thinks you might not like. That is a communication issue.
Clearly you have been thinking about anal sex. Why not tell him you would like to try it again some time? If you talk about sex, then it's easy to talk about what you like, what you would like to try, and by the way, what you have tried in the past and would like to experiment with again.
It's hard to give advice without knowing the relationship you have. You could just suggest it while in the process of having sex. Talk dirty. Tell him to do it. Beg him to do it.