I started in middle school with TI-BASIC apps on my TI-85 calculator to help me in math and physics classes. Then I moved on to VB .NET a few years later when I got to university. Pretty much I did it all with scratch-my-own-itch problems as they cropped up.
It progressed as such for me (mainly due to course progression at school):
TI-BASIC >> VB .Net >> C >> PHP >> C# >> Python >> Ruby
It progressed as such for me (mainly due to course progression at school): TI-BASIC >> VB .Net >> C >> PHP >> C# >> Python >> Ruby