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Oldest image I found was this old long Okayu, which I'm pretty sure I only have because I was downloading images from a /jp/ longcat thread. I remember seeing early Ai-chan threads in the catalog and thinking the nascent virtual idol thing was cute, always thought Akari was hot. Remember reading that one of the JAV studios announced they were doing a porno of Kizuna Ai, and that was either the same year or the year after she became a thing. I probably have that on a hard drive somewhere, never watched it because I didn't and still don't have a 3D headset.
Pretty wild how things evolved. I doubt anyone back then would believe where the industry would be ten years down the line, hell they'd be shocked to know that it's an industry.
