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...have you tried atWar (formerly Afterwind)?
I discovered this yesterday while I was looking for some wargames, it's basically a free to play online multiplayer risk game with a map editor and hundreds of custom maps (Game of Thrones, Lord of the Rings, spaceships, etc.) for up to 20 players. It's pretty similar to the board game except it's not grid-based. I think the map editor might be behind a paywall though.
You can play in your browser or with a game client (I think it's available through Desura too) and you don't even need to register to play if you don't want to. I remember some people organizing a Steamgifts risk game a while ago, I thought this might be of interest :D
Game trailer here
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