I started playing chess on the web in '96-'97.
I don't think there were all that many chess playing sites around then. I was both computer and internet illiterate at the time and spent most my time trying to figure out how things worked.
The first chess playing site I found and joined was Chessmaster. It was only around for a very short time then disappeared and later re-appeared as part of a larger game site, but it wasn't the same as the original. I think it even required some downloaded program or you had to have a store-bought Chessmaster game or something.
The original site was quite beautiful. I had a 14.4 modem and it took about 3 minutes to load the site. A little blue rectangular counter would appear in the top left corner of the screen indicating how much longer it would take to finish loading. After it loaded, there appeared a walnut and maple board with ornate red and white pieces. There was a chat window, a timer window and a challenge window, I believe. It was quite stunning and waiting for everything to load was a sort of magical experience for me, not something to be dreaded. It was almost like a fanfare before the main event that got my adrenaline flowing.
I didn't do especially well playing on that site. There were some good players, of course, but mostly, I wasn't used to short-timed games as one is apt to play on the internet and, while I've always had trouble with the operational skills, it was more pronounced back then. So, a lot of my poor play was due to non-chess reasons. But, one day, the site just disappeared. The next place I found to play was FICS (the Free Internet ChessServer).
...that's another story altogether.
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