You look like a very young guy but it is time to make the move. I would do it now if I were you. That way, by June your head will already be "seasoned" and not look white compared to the rest of you head/face that has seen the Spring sun.And this leads to a word of caution for both you and Nassauguy. Get a good sunscreen and use it when in the sun!!
Virtual head shaves give you an idea of how you'll look, but they can't show you how you will feel. We can all attest that a shaved head feels incredibly good. Why wait to experience it?