To beat him, the Chosen One needs a high Strength (about 9) and an Endurance of 8, and a bit of Luck. Not having these stats will certainly prevent any chance of winning. However, to begin this quest requires the Chosen One to be a certain level.
If Francis wins, the Chosen One becomes his gimp for the night and will wake up at his house with a ball gag in their inventory. Plus, a female Sexpert will have all the inflatable rubber dolls in the game named after them, instead of after Tandi. The Tanker vagrants and female punks on the PMV Valdez in San Francisco will also mock the Chosen One and call them names.
Francis can be fed two Buffouts to decrease his Strength and Endurance dramatically after 6 hours, improving a few chances to beat him.