Making Custom Hardware

Ok /prog/

I want to build my own hardware for my computer but have no clue where to start.  My design will be simple game controller with 6 buttons (up, down, left, right, A, start).  I would LIKE a usb connection, but a serial port or parallel seems more simple.

I also need to program it.  What would be the best method for making custom drivers?

Are there any good tutorials for making simple hardware like this? (I'm running window XP)

Which end of the soldering iron gets hot?

This reminds me of the time I taught 13-year-olds how to solder. I plug in a soldering iron on my bench to let it warm up for the demo and start explaining the history of soldering, what metals are used, what the soldering iron is, etc. when halfway through, this somewhat retarded fat kid standing near the front tried to grab the iron from the bench by the tip and within seconds starts screaming like a bat out of hell.

As I was fixing up his burn he looked at me with a bemused expression and said quite timidly, "I didn't know it was hot."