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The first one probably doesn't count, as it was an accident. It was a Weepinbell. I dropped my Pokemon Red into a puddle of water. My mother helped me get it back to working. When I popped it into my Gameboy Color, I went looking through my pc and found a level 98 Bellsprout sitting in there and was like "WTF!?!?!?!"
The first time I hit level 100, without glitching or anything, was with a Pidgeot on my Pokemon Gold.
Unfortunately, I never raised a pokemon all the way to 100. I would always get bored of training and end up restarting the game that I was on.
I think the closest I've gotten was about 89 lol
My awsomesauce Blastoise a female one i got it from red version traded it to silver then again to ruby but then i lost ruby to the washing machine and i've never been able to lvl a squirtle again... but anywhoo blastoise was my first lvl 100 pokemon i still remember the moves lmao hydro pump/body slam/ice beam/surf. i miss her :'''(
My faithful Swampert in Sapphire. Oh, how many times didn't I battle the E4 and go through the credits while raising him and others...good times, good times.
'twas a Pidgey back on Pokemon Red as a joke. I refused to let it evolve because, face it, I was 10 and thought having a Lv. 100 Pidgey would be the funniest thing in the world.
My first was my Latias in Sapphire, Serena. I was so sad when I accidently deleted it in favor of a Shiny torchic >.< But I still have Flame today =) Though he is only level 90...
My Sceptile moved from Sapphire to Diamond. Thank you boosted experience! But I got impatient and used bout 3 -4 Rare Candies on it to get it from 96/97 to 100 :) It was also my first Pokemon to get an Effort Ribbon, so I thought you needed to level Pokemon to 100 to get the ribbon. I hated that woman, who said my Pokemon hadn't tried hard enough >___>