Both originate from tiny mindless pencil doodles. I'm in the habit of doing those, especially when I'm talking on the phone (at work or otherwise) and I am never conscious of what I'm drawing until well after I've stopped.
For the first I have this odd idea of a soul (despite its grotesque appearance, I have positive, compassionate feelings about that figure) floating at the end of a string like a balloon, leashed, unable to find release. I even considered adding balloons around it, a tragic/cheerful/scary mix. But I think I won't. It doesn't fit.
In the second, this could well be Charon (from Greek mythology), ferrying a soul across the subterranean river Styx (or Acheron, in different sources).
I don't know why I have been coming up with these concepts lately. Like I said, it's not conscious. But they are very emotionally laden. I was worried about my father a lot lately, who was facing serious health problems. He is much much better now, but the notion of our mortality is still heavy on me.
At any rate; now, to find time to actually finish them. And I have many, many more unfinished paintings in my hard drives, gathering digital dust. They'll rise up and eat me one day. D: