The 011/ADV-P Kyogre ex from CoroCoro comics in PSA 10. Graded myself (It was in a batch with other cards but this one had the lowest cert number, so that makes this the first.
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PSA 10 full art Tauros GX from Guardians Rising for $20 on auction. Such a great playable card. Still own it!
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1st Ed. PSA 9 Base Porygon for $16.
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1st Ed. Jungle Flareon PSA 9 and 1st Ed. Fossil Articuno PSA 9 around the end of July 2018. Won the Flareon on an auction for $45 shipped and Articuno was $60 shipped.
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PSA 6 Unlimited base Zard $50
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My first PSA cards were a local purchase.
They were a PSA 9 Unlimited Dark Charizard Holo and a PSA 8 unlimited Base Set Charizard.
I still have the Dark Charizard although I cracked it out and put it in a binder collection and the Base Zard I sold.
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PSA 10 unlimited Jungle Pikachu. My favorite card 
PSA 9 blastoise EX, FRLG. Followed shortly by a 9 venusaur EX, I wish I hadn’t sold them 
some great cards
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Psa 8 shadowless haunter for 6$
I bought it when just looking for a shadowless copy of haunter in general
Got me into graded cards
Dark Typhlosion 1st edition PSA 9. I was sick of getting beat up copies when ordering raw ones, so i dug into that as my first for 90usd. Still have it to this day and even bought a second to go with it!
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PSA 8 Shadowless Blastoise (what a surprise)
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My first card was a shadowless Blastoise PSA 6 for 105€ which i bought from TCA Gaming this year. Now I’m addicted to pokemon cards.
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PSA 8
1st edition Dark Dragonite!
It became by far my favorite card when I was a kid when I first saw it so it felt like the right choice.
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PSA 9 Neo Genesis Lugia Holo. One of my favorite pokemon, and I had a lot of nostalgia for that card!
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PSA 10 1st Edition Fossil Dragonite- $250
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This guy of course, March 2017
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PSA 10 Gym Heroes Lt Surges Magneton Holo in 2016 or something like that - still have it!
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Psa 9 shadowless ninetales. Sadly I sold the card when I started buying 1st ed. I would’ve kept the card as a sort of memento of my pokemon collecting journey if I had known I would get so involved in collecting. I don’t even have a picture of the card 
I do consider myself lucky to have most of my childhood collection though, as most of my friends are bummed they don’t have theirs since they were either given away or thrown out by parents.
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Just checked my old eBay confirmation e-mails, and apparently my first ever PSA card was a PSA 6 Japanese Misty’s Tears in 2015 for £9. Slightly embarrassing, but i’m going to claim that I was just looking for a raw copy, found that and thought it would be worth a little more for the novelty of a graded version. It was definitely a gateway drug though.
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PSA 10 1st Edition Rocket Jolteon
I’m simultaneously sad and happy that this card is a non-holo. Sad because this card would have looked fantastic with a WOTC holo pattern, but also happy because I wouldn’t have been to afford it if it were holographic 
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