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Will has to get "milked" at least twice a day. It’s encouraged that another person supervises to ensure that none of his cum is being wasted. Obviously his family wasn't going to do it, and they didn't have the money to hire anyone. They could have ordered a fancy machine that jerked Will off all on its own, but the idea of it made him feel so much like a lab experiment that it sent a shudder down his spine. He decided that he wanted it to be a friend who helped him.
So Mike supervises. Mike supervises a lot.
In the wake of a bizarre government mandate, Mike and Will do their chores.