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my first lvl. 100 was my blastoise back in firered. sadly i was dumb and gave it terrible moves with low pp so i could never beat the elite 4 because he was always my last living pokemon but all his moves would run out and id have to struggle into death.
I'll be point black honest. My first level 100 was my Charizard in Blue.. along with the rest of my team after I got a bunch of Rare Candies via the 'M glitch. :7: Back then I was stupid and didn't know about EVs and base stats and things like that. Those were fun but silly times. My first Pokemon that I actually leveled to 100 without cheating didn't come until a few years later in Crystal. It was my Meganium. :7:
Mine was Blastiose way back in my very first Pokemon game, my Blue version. I remember training it just as much as I could because I didn't know what the level cap was at the time, but I soon realized it once I couldn't grow anymore.
I've never leveled a Pokemon up to 100. :<
Normally not long after I beat the league, I stop trying to level up so much. I'll go through the league several times beating them but it doesn't ever result in a level 100 and I'm not sure I'll ever reach that level without "help". But aw well, I don't got time fo' dat.