Make him less timid?

So my boyfriend and I have been together officially for about a month and everything is good. But when we fool around, he’s a little timid. I am too because I’m really submissive.

How do inane things just flow a little smoother? When we’re doing stuff it’s just sometimes a little hard to move to the next step. We’re both always ready, I think we just don’t know how to lead into the next step smoothly.

We’ve done everything, I just want to get there easier if that makes any sense