The Australian: Sir Richard Branson gives passengers a serve on AirAsia flight from Perth (including video)
He lost a bet against Mr. Tony Fernandes, the CEO of Air Asia, about the winner of F1 racing 2 years ago. He carried out this performance as the penalty of their gambling.
He seems to be high-spirited as if he had a habit of transvestism. At least his funny behavior was successful to advertise the name of Virgin Atlantic.
As to bet for dressing as a woman, I remember an episode in The Romance of the Three Kingdoms.
Sima-Yi, one of the generals of Cao Wei, was prepared for invasion of Shu at a borderline. His boss was doubtful that Shu would overrun the border and he was not concerned about the defense. Therefore Sima-Yi invited his boss to bet whether the army of Shu would come. Sima-Yi said that if they did not come he would dress as a woman. The boss laughed at him. The result was victorious of Sima-Yi. He responded quickly to the invading army of Shu and overcame it. The boss was disappointed by his own lack of insight.
Sima-Yi is my favorite person in the Three Kingdoms era.