He had been so sure of himself.  He thought there was no way the Cubs would win the series, They had been a losing team since 1908.  He made outrageous bets, knowing he could not lose.  Then the unthinkable happened and Chicago beat Cleveland 8 to 7.  Now he had to pay up on all those bets.  His “friends” were the first to collect.  Bending him over his couch and taking his ass cherry. He begged and pleaded with them, but they just kept laughing and saying “a bet is a bet….bitch.” The five of them were just finishing the first round of breeding, when the doorbell rang and ten guys from the bar down the street came in to collect their winnings.  They brought with them a red, white and blue jockstrap with the Cubs logo on it. He had been so focused on losing his ass on a baseball game that he forgotten about the other bet.  He had to wear the jockstrap, and nothing else, down to the bar and buy a round of drinks for everyone there. They put him in the jock, then the ten newcomers train a train on his ass.  All those big, thick cocks pounding against his prostrate, made him cum twice in his new jock, before the group was finished.  

His reputation as the neighborhood cum dump was firmly established as he walked into the sports bar wearing only a jock stained in the pouch with his jizz, while his ass was dripping the loads of fifteen men.