Bobby is a character in the game Life of Holly. He is working at a local farm, his primary job is milking cows.
During daytime, he is resting in the barn, overseeing the milking. You can ask him for work as a cow, if you have got big enough boobs (visit doctor Greg at the Hospital to for boob enhancement). After a test you can work as milking cow. After finishing 3 shifts, you can ask Bobby to work as a licking cow, and after another 3 shifts as a breeding cow. These promotions will increase your pay and experience gain.
After 19:00 he hangs out in front of the supermarket in the Residential District. If you have the barter skill, you can "convince" him to buy you alcohol. The more satisfied is he with your effort, the more and better alcohol you will receive.