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The final mouthful taking by a competitive eater or, more crudely, the pay off at the end of oral sex
Dave grabbed the chunk of kielbasa to ensure he had the winner's mouthful ahead of Jane, Peter and Samantha.
A group of friends or individuals that cannot stop winning.
You already know were part of the winners circle...
A feeling of never being satisfied no matter how successful you are in your life in regards to money, wealth, power, status......
"Chris is already regarded as a top 100 richest in forbes magazine but he wants to crack the top 10. he has winners syndrome"
To fill a vagina/ass with an object or food and have sex with the person with the objects or food in them.
Juan: I love doing the Urban Winner....
Mark: Have you done it with ice?
Juan: Have you ever tried a Popsicle at the same time?
A double winner is a person who is afflicted with both mental illness and substance use disorder.
Hi, my name is Brooke and I’m an alcoholic and have bipolar disorder. I’m a real double winner!
When you get tired of WINNING.
Eric was suffering from winner fatigue so he let that bitch ass Gabriel win.
The 'n' word for white people. It's also conveniently a positive thing to describe your mates.
"What's up my winners?"
"Take the strap-on off my winner"