I have known this boy for ever and I am friends with his little sister. He is the same age as me and I really like him. Does he like me back and how do I tell him I like him without straight out asking him?

Why would you not want to straight up ask him. If you try to "read the signs," you're setting yourself up for disappointment, and getting mixed messages. If you want to start something with a guy that is not a normal friendship, why don't you start on the right foot, and do it with open, honest communication? It's exactly what is needed in a relationship to strengthen it, so why not practice now?

Just ask him, straight out. How old are you both?

Since we have no psychics here that can tell you whether he likes you or not, you're really just going to have to ask him straight out.