Guiding or no guiding??

So me and my bf keep having this hilarious little moment where he can’t just penetrate straight away, takes a minute cause he has to guide himself in, once it’s done we’re good but I’m wondering if that’s common or not and maybe what, if anything, I can do to fix that? We both laugh at it but sometimes it’s a little annoying when we can’t just get to it. 😂😂🤷‍♀️🤷‍♀️