Hi Josh, you're probably getting some razor burn. Lots of info here on shaving techniques. When I started shaving my head, I used Bump Patrol to ease the razor burn until my scalp got used to shaving against the grain.
Making your head shiny is alot easier than making it matte. There are products out there to help keep the shine at bay. A head that is shaved smooth and healthy will shine naturally, and for me, I love a really shiny head.