First you need to select a starting point. What skill do you want him to learn or gain tonight? That's a choice that only you can make. Maybe you decide tonight is the night where I teach him to put his hands on my neck. Maybe you decide you want to make tonight about talking dirty to one another. Maybe you decide that you want to show you riding him in cowgirl or reverse cowgirl.

Pick one thing, tell him "this is what I want tonight". Ask him if he is comfortable trying that thing. Then in as hands on manner as is possible lead him. If you want to teach him about how much grip strength to put onto your neck, then show it by gripping his arm. If you want to teach a new position, lie down or assume the position for him and tell him to copy you. Give him the hand signals run down of what you'll do when you want to stop, ask what signal he wants to signal to stop. Have a dialog written up where you two act out a scene together. There are so many different ways to aid him in learning how to handle you.