To spend alot of money on a girl. As in thousands of dollars.
When a guy has a large amount of money he will usually carry it in a rubber band. When he spends his money, on a girl, He is "poppin a rubberband"

the whale tail is the shape formed when a g-string rides up high over a womans trousers

to fuck a very pretty girl with a condom

1. im gone pop a rubberband on her
a good fuck with a condom

To break a condom while having intense or rough sexual intercourse, as in only a rubberband is left from the once intact condom.

to use a condom, or "rubber", while having sexual intercourse with an attractive girl.