Mobile Phone - 1996, a colleague sold me a Nokia 2110 for a one time fee. Whilst I filled out the contract, I feared the source was rather questionable; even though the item was completely new, boxed etc. I think I made about three calls in total (2 were test calls) during the duration of the 'contract' and never received a bill? I was terrified that I would incur horrendous fees and be arrested.
Computer - 1991 a Packard Bell 386. Computers were considered mystical objects, and my Dad bought a PC with the aim that I learn and then teach the rest of the family. My parents took one look as DOS and fled.
Taught myself completely from scratch. I was seriously computer illiterate having never owned a computer up until that point. I remember investing in a sound card, speakers and a CH Flightstick all to play Aces of the Pacific. Imagine my horror when installing, Aces did not work! With much head scratching and messing about working out himem.sys and EMS memory; it burst into life. Words cannot describe the moment - Just epic.