Mother

Your mother has a gambling problem, and you're the 'solution', you're the boy in the picture, and so basically, instead of going into deep debt, she used you when she loses money, as the difference in money for however many days to the person in exchange for no debt. Plus, you've always looked nice in men's eyes, and without the potential problem of pregnancy or charges, cause male with male victims tend to be ignored; they take your mother up on her offers without a second thought.