Penny Dessertine was a 22-year-old woman from Portland, Oregon, who was among a number of women abducted by a group of dragons.
According to what her sister told Sam and Dean, Penny was very shy and at all the adventurous sort that would fly through a lightning storm in a two-seater. She was in fact terrified of the plane, but only agreed to fly in it for Stan, her pilot boyfriend, because they were just starting to get serious in their relationship and she didn’t want to seem uninterested in him.
While taking a trip in a light plane trip piloted by Stan, the plane was attacked by a dragon. The dragon killed Stan and took Penny because she was still a virgin and thus a suitable candidate for carrying out their plan to raise the "Mother of All" from the depths of Purgatory. She had been chosen from a group of similarly describable young women who had also been abducted. She was later saved when Sam and Dean Winchester came to their rescue.
- Penny's surname is very likely a shout-out to writer Rebecca Dessertine.