Some of the most satisfying moments I've had in TES involve: Completing long quest chains (like guilds). The awesomely cautious feeling I get whenever I first enter a dungeon/cave. Getting armor/weapons that are strong and I think look good on my character.
One moment of satisfaction I'm dying to feel is when I take on my first dragon one-on-one. Also, you cant beat the feeling of opening the game for the first time, or customizing your first character.
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