I agree that Bobby is at his best on the bottom, which position he assumed most of the time in his first
Broke Straight Boys run as a teenager. In his second
Broke Straight Boys run in his later twenties, Bobby is clearly topping more. Just as the older models were all fucking him when he was a twink, so the older Bobby wants some twink ass himself. I guess he has earned that to an extent, but he should not give up bottoming completely, particularly after this scene where he told Max that his ass "felt like a pussy." After that remark, Bobby deserves some other models saying that his ass feels like a pussy. That would meet your "Give him something that girlfriend can't do for him" test.