The first instrument that was given specifically to me and not rented through school was the http://equipboard.com/items/casio-sk-1 that my folks got me for x-mas in 2nd or 3rd grade. I learned basic chord theory dickering with this little toy while I was studying viola and violin in school. I loved it dearly until someone gave me a bigger Yamaha kids keyboard.
My 1st gear purchase that I selected myself was a used MIJ Squier strat, black with a white pickguard and rosewood fingerboard. I purchased it from the little brother of the best sax player in Jr High jazzband around 1992 with some of my own paltry funds and some money my dad gave me on the grounds that I join the jazzband (since I had just quit orchestra). Dad also bought me a chord encyclopedia at the time, explained the modes to me (he had taught me a major and minor scale by then, so it was a short step to getting all those scale variations) and told me I could figure it out or quit, but that any time I wanted to take lessons he would split the cost with me if I could find a reputable teacher with a classical or jazz guitar background (good luck with that in the 'burbs, I coulda found a guy in Philly proper, but if I was going to Philly it was about punk rock -which we called grunge then- and getting into trouble, not jazz lessons).
Well, I really bonded with that great beginner strat and kept it until the early 2000s (even though I got plenty of other guitars, I still played her). It was the best student guitar I've ever played. Those Japanese squiers were just fabulous. After I got mine a bunch of other kids saw me playing it at school events and got their parents to buy them squire strats, but theirs were new Korean models and really sucked. Most of them got discouraged and quit. I would like to pretend my musical family, diligence and talent is what kept me at it, but I suspect the fact that my 1st guitar was built to a very high standard o quality had a lot to do with it too.
Anyway, I kept that strat until 'one foggy christmas eve' I heard that a good friend's 12 year-old son, Clifton, was learning guitar and needed an electric that wasn't a struggle. His mom was perpetually short of cash like we all are and around that time I had bought 2 more strats... so I slapped a bow on her and gave my squier to Cliff for x-mas and he's still playing it down in Memphis as far as I know. I sort of wish I had kept it for my little boy, Lucian, but I was over a decade from fatherhood then. Who knew? Anyway, I have plenty of great electrics, when he's ready he can pick one or I will trade one of mine for anything his heart desires :-) No entry-level guitars for Lu!
Anyway, that's my story.