I suggest you start by learning how to write a GUI based program at all. A good starting point is the free
Visual Studio Express. Choose the language you prefer (basic, C++, C#). Learn how to code a program that interacts with you without connecting to your µC via USB.
Once you have manged the basic skills of GUI programming you can tackle the task of communicating with the µC.
This two-tiered proceeding alllows you to tackle the different aspects (GUI programming, communicating with µC) one after the other.
It may be a good idea to buy a USB experimental kit (
like e.g. this). Make sure the kit comes with instructions and possibly sample code.