WHY NOT? (Feminization, Crossdressing)

Jerry wakes up one morning tired of his mundane life. So he decides to try something different: instead of saying ‘no’ to every opportunity that presents itself, he will say, ‘why not?’ He ends up quitting his job and travelling the world and he couldn’t be happier.

But his ‘go wherever the wind blows’ mentality gets complicated when he runs out of money, and he finds himself with a unique opportunity involving two rich men and a pile of women’s clothing. Will he say no, or will he say 'why not?'