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When you try to fart but end up shitting in your pants.
Carlos and I were hanging out in the hotel room when Carlos lifted a cheek and squeezed one out. Unfortunately it sounded wet. Carlos gambled and lost.
When one has "gambled and lost," they have tried to fart, but in the process, some fecal matter has come out. Usually resulting in a "shower of shame." Opposite of "gambled and won."
Rory: Hey, where's Jake?
Brian: Oh, he gambled and lost and now he is taking a shower of shame.
I just cut a big fart and I gambled and lost. My pants are in the washing machine.
When you push out what you think is a fart but turns out to be a turd.
Dude, after that Mexican food I gambled 'n lost. I had to run home and change.