joeyboy, I don't have experience seeing a dermatologist about my junk but I have seen a urologist twice, once for the big snip and again for a bladder scope (yeah, they actually do shove the camera in THAT way, ugh).
For me, it was far less uncomfortable and awkward with the scope being done by an older male doctor than with the younger male doctor who did the snip along with female assistants in the room.
I'd recommend finding an older male dermatologist. They've seen everything, in all different shapes and sizes. It would feel much more awkward, to me at least, to be showing my stuff to a female. Unless, of course, I'm paying her by the hour.