So there you are, a young guy in the employ of an eccentric multi-millionaire (as a personal assistant or whatever), and out of nowhere the dude dares you to dress up as a woman—head to toe, from the skin out—and try to pass yourself off as an Avon lady to friends and family back in your hometown. On the line: a cool million simoleons. So what’s a poor cross-dresser to do? (Hey, don’t ask me WHY the old guy wants our hero to do this; it’s just something you have to accept at face value in order to enjoy the caption. Think of it as something that might happen in Bizarro World—although when you think about it everybody and their dog must cross-dress there.)
For those of you who are paying attention (and kudos if you are), I actually did use this picture once before, in a vignette from last year: “Compulsion and the Cross-dresser“. It’s quite different from this caption.