I've never seen a Lollipop Lady like this, but I keep looking.
I did this sketch using my Wacom tablet and GIMP. It was an attempt to draw a semi-realistic pin-up babe. I'm very pleased with her, she feels sexy in her skimpy outfit but retains a comic feel. I'm pleased with the way the cartoon underwear looks especially with the patterns on her smalls. The lace top was very easy to do on GIMP.
I might try some more ladies in different poses and outfits soon.