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I don't understand this. If losing money is painful for you, why do you continue? Sounds irrational to me.
I find this like taking revenge, since people don't want to get humiliated, they tend to retaliate. in terms of gambling, people don't want to lose so in order to recover their losses, they tend to chase their losses which in the long run incur them more losses and the loop is formed. Now the person is trap in an infinite loop until he realized that he was been trapped.
That should be the way but people tend to lose control when triggered which often happens in gambling. So instead of the plan of having a bankroll of $100, the person end up spending 10x just to chase the losses until he runs out of fund.