1-A "cheek finesser" is a modern day word for pimp. It describes a male/female that has an easy time pulling girls with no attachment.
2-The highest possible title given to a person who pulls females easily.
He is a professional cheek finesser, he'll take anybody girl.
Lady's be careful, the cheek finesser just showed up.
You know he ain't no good, he ain't nothing but a cheek finesser.
When I grow up I want to be a cheek finesser.