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This phrase stems from cotton fields that were tended by slaves. Pick my cotton in other words means 'do me a favor' but is not a question, it has more of a 'do it' tone. Usually the favor being asked is a simple physical favor such as turning off a light or plugging in cables. Alternatively it can be used as 'I'll pick your cotton' which is used to say, 'Yes I will do you a favor, but I hate you.'
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