To gamble in a wild and high-variance fashion. Often applied to loose and aggressive play in poker, or by poker player to other forms of high variance gambling, like baccarat.
On tilt from losing in the pokergame, he decided to gambool it up at the pit to try to get even.
A word becoming common for describing a Condom / The use of a Condom in New Zealand.
A gumboot been a item of footware that is made out of rubber and completely waterproof.
Jimbo "Bro, heading to down Hamilton this weekend ay."
Kev "Ohh true, I got the clap last time I was there ay, gumboot up dude, hard!."
Jimbo "Haha, will have to double layer!"