The guy pictured in the photo is Richard Branson, aka the boss at Virgin. Just search his name on Google Images to get the humor.
The terms were such that the loser had to serve as a flight attendant on the winner's airline. The photo is of Branson fulfilling the terms of the bet.
http://news.yahoo.com/richard-branson-swaps-suit-skirt-honor...
Apparently some people are taking offense or something? I'll just leave this here: for whatever reason, the Brits (and Richard Branson is one) think dressing up as a woman is funny (in a harmless way) in and of itself and they have thought that ever since I've watched Benny Hill and Monty Python TV shows (ie, since the 1970s anyway). No big deal here.
Like you say, no big deal here.
Richard demanded that they go and put pressure on the boat guy. They went. There was a storm. Richard and his wife decided to swim to safety.
Everyone else died.
Now that I think about it, in the book, Richard also forces other people to do things they don't want, and mentions breaking someone else emotionally.