I wonder if other bald/balding men have this problem.
I first became aware of it when I started going bald - thinning on top, standard male-pattern baldness - and I had trouble getting the barber to cut the thinning hair up there. He'd do what I asked on the sides and back, where the hair was as thick as ever, but I had to insist before he'd cut the top, as well. Finally I realized that he was convinced I wanted to comb the remaining hair creatively so as to hide the bald spot, presumably because that's what he'd do.
Nowadays, I have only a few wispy strands on the top, and I go to Great Cuts instead of an old-style barbershop. (Cheaper, and no TV sets blaring sports, yahoo!) All the barbers are barberettes or hairdressers - i.e., female. Some of them still won't cut the wispy strands, and I have to repeat the request after they're otherwise finished, when they hold up the mirror and ask if the haircut is okay. Yes, except for those long, wispy hairs on the top. Cut 'em.
If I did care about trying to hide the baldness, letting those wispy strands get extra long wouldn't be my choice of a way to do it.