If that's actually true, it's kind of sad and creepy considering Riddle is 26 and Randleman is like 40 or so. What kind of 40 year old makes disgusting bets like that with a guy in his 20's? Trashy and disrespectful for anyone to make bets like that in my opinion. Regardless on whether he won or lost, he should feel bad about being apart of something like that and having other people find out about it, Riddle too, so I wouldn't be bragging about it if I were him.
That being said, it sounds like something out of a raunchy movie.
Riddle has a kid on the way too and goes around sleeping with women for bets. Great role model.