[SwiFtHD]

I think this is a good idea. All you are missing is a maximum number of games to play or that could vary with difficulty. I personally did 20 matches and I only lost four. (Better at Blackjack than most)
Example: 20 matches (moderately increase risks,involving leaving the door unlocked or partially opened, calling a friend over and telling them to let themselves in in an hour) Stuff like that.
25 Matches: (Getting more risky, maybe involving cross dressing or dildo play)
30 Matches: (Extreme, maybe have homosexual porn on the computer, something very risky and humiliating)
Getting naked and bounding yourself while being erotic and not so risky I think is good for beginners. But I think another part of the stimulation of this is being caught for some people so maybe a variation of difficulties would be good. Just an idea. It's a great dare and although I didn't have the high loss results I enjoyed it and am planning to play it again with more matches or a higher difficulty bot.