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I have once before. My uncle lives on a farm and one of the last times I visited, I ended up going out with my cousin to see how cows were milked. I was not good at it at all so I lasted maybe a minute before handing the job back over to my cousin, much to his dismay. XD;
I have never actually milked a real cow before. But, at one of the local fairs every year, they have a big farmers/agricultural exhibit. They have a statue of a cow, with a rubber utter on it filled with water that kids can go up to and practice milking. It's actually just like milking a real cow. So, I guess I can say that I kind of have?