I know the original question of this thread has already been pretty much solved, but it's a boring night here so I'm just going to answer as if this were a general discussion sort of thread.
Honestly, I feel like this is an individual issue. I will tell you, though, that the prevailing school of thought in the drag and male illusionist community is that if you are performing as a male, always wear a penis. This is kind of an exclusionary school of thought, because honestly you don't need a penis to be a man, but I can see where it comes from.
I personally have started wearing a packer, though honestly, it's not for any aesthetic reasons, I just don't feel comfortable presenting as a man if I don't have it dangling about, but I think this stems from me being trans and now wearing the packer en homme. There are occcasions where I won't wear it because it looks silly or feels weird. My Petyr Baelish costume would be impossible to wear the packer with, because I can't wear boxers with the leggings because they bunch, and without boxers I have nothing to hold the packer in place (the leggings aren't tight enough of on their own, being historic leggings). But you mostly can't even tell if I'm wearing it.
Ironically, the only costume I've ever worn where it actually shows is when I've cosplayed as David Bowie. XD
"I don't have to conform to the vagaries of time and space...I'm a LOONY for God's sake!"