Thinking it might not work is no reason not to try it. If he is more experienced don't you think that he has done this before? You are more experienced now than when you tried it before.
With this position you can get good clitoral stimulation as well as vaginal. Don't try to go up and down like a man does in missionary position. Instead kind of rocking or forward thrust going, it' hard to explain but easy to do, you want the kind of movement you get moving forward rather than up and down and more from the gluts and PC muscles than the legs. On top you can easily get more of an orgasmic wave going rather than the little "explosive" orgasm you may be more used to. Once you get that wave going you can ride it for 5-10-15 mins. Just experiment and see what you can do. Don't take as you have start doing one particular thing and keep doing it.