A millionaire gambles his fortune away, going down the path of a cuckold.

TheNovelist2000

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A wealthy man loses about 70% of his fortune ($133 million) in a high-stakes poker game. This isn’t his first loss—he’s battled gambling addiction for years, once worth $500 million—but it’s the largest setback yet. Returning home in his Mercedes, he realises it’s not the loss that frustrates him, but the lack of thrill. That’s why he had kept raising the stakes today, hoping to feel that high again.

Then, he sees a group of five hobos gambling on the curb. It is a simple dice game, but they are so invested in that game that a fight has broken out. He wonders why they get so excited over winning each other’s trash.

Then, it hits him. He realises that they are so thrilled because they are betting on the very last things they own. On the other hand, his wealth—the remaining $60 million—protects him from real risk, stripping away excitement. To reclaim the thrill, he stops his car and challenges all five hobos to a coin flip. The stakes: the hobos’ few possessions—the dirty mattress they sleep on, photos of one of them’s ex-wife and children, a dog, and a few other items—versus the millionaire’s company, mansion, and jewelry.

The man with the dog is reluctant; he loves his dog very much, but the other four eventually convince him. Then the coin flip begins—and the millionaire loses.

The millionaire hesitates to go through with the deal, but he eventually realises that the real thrill was in losing it all. In his heart, he wants to see how his wife and two adult daughters will react. This story eventually leads to a dynamic where the three women submit to the five hobos, and the man is cucked.
 
Or more likely the wife has an escape account that he knows nothing about, seeing as she's aware of his addiction, and blows town, leaving him to service the hobos himself.
 
It's not unusual for wives of men with "troubles" to create an escape plan. I have a friend who just 'prefers using cash' for tip giving rather than her debit card. So she would get a little cash back with every store purchase for that supposed reason. In reality she was funneling it into an escape account due to her husbands drinking problem.
 
It's not unusual for wives of men with "troubles" to create an escape plan. I have a friend who just 'prefers using cash' for tip giving rather than her debit card. So she would get a little cash back with every store purchase for that supposed reason. In reality she was funneling it into an escape account due to her husbands drinking problem.
That can add realism to the story. She has a secret escape account and offers her husband a way out, thinking he was in real trouble. The man, arrogantly believing that the grateful hobos would take care of him, calls her a thief and accuses her of going behind his back. She leaves, and the hobos eventually
turn on him.
 
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