I'm going to show my age now:
- Gameboy Camera and Printer Combo
First digital camera I ever used and arguably one of the first use of augmented reality in a piece of computing hardware. The ability to print from the console was, in 1999 an absolute miracle.
- Sega Master System
I had a Commodore Vic-20 prior to this for gaming but was too young to appreciate its computing side. I had borrowed my neighbour's Atari a few times but the Master System was the first proper console I ever owned (and I still think it was miles better than the NES!)
- 2006 1st Gen Macbook
I sank £750 on this in the middle of my postgrad and it was not only the first Apple product I ever owned but also the first computer I ever had that made me interested in learning computing and doing things with command line.