QUOTE(TheCheshireKhajiit @ Oct 7 2018, 08:49 AM)

Khajiit can’t even remember his first online purchase.
I've not felt up to a lengthy full investigation. Searching SHOULD have been relatively easy. I've logged all non cash purchases into a searchable computerized account ledger since 1992, after all. That predates my joining the internet by roughly four years. It's possible I ordered sometime while still accessing the web via BBS, but suspect any such transaction would be ordered via a company's online site (if they were called that back then) and paid for by check send via snail-mail. Not ruling that scenario out, but for now I'm concentrating on debit card purchases.
So far as I can tell, I didn't start using a debit card until circa early spring 1996. For the first some years I apparently didn't know the proper way to enter debit purchases into the ledger. They're all there, but entered in such a way as to make searches all but useless. I therefore have to expand each entry one at a time and hope for the best. Makes for tedious work.
So far as I can tell, my first debit purchase occurred 4/15/1996. The memo field says I bought Strategu Plus / IE Magazine for $6.99. (Surely Strategu is a typo of Stratego?????) Amazingly I did NOT note the payee!!!!!!! As I see it, this had to have been two magazines or one mag and something else bought locally rather than online.
On 9/27/96 I paid $40.95 by check to "3DO Direct" for the first "modern" MMO, Meridian 59. This is almost certainly local despite "3DO Direct" being listed as payee. Also, I'm fairly sure I bought M59 at our local Babbages.
On 11/22/96 I paid $9.95 by debit card for "Meridian 59 monthly fee." This would have been my first M59 monthly payment, and very possibly my first online purchase. I distrust it solely because it's what I suspected I'd find. Too pat, in other words. For now it stands.
On 4/11/97 I paid $259.08 by debit card for a 2.5GB hard drive. The payee is listed as "Midwest Micro." I'm pretty sure this is/was NOT a local establishment. If so, it's the earliest online purchase of a PHYSICAL product I've unearthed thus far.
Of possible interest, on 8/26/1996 I paid $19 by check for "Daggerfall." The payee is listed as "Bethesda Softworks." This has me stumped. It can't be for the the game itself, which would have sold for full price at the time, and in any case was acquired locally. $19 was, I believe, the cost of a PC strategy guide back then. If I ever owned the DF strat guide no physical evidence remains.