Beautified (Crossdressing, Feminization, First Time)

Tony has been looking for a summer job with no luck. He notices that suddenly, his sister has all this disposable cash and asks her where it came from. She tells him that she's started selling cosmetics and creams for a multi-level marketing company, Beautify You, and he decides he wants in on the action.
There's one catch - to be a successful representative, it's pretty much a given that you have to be a woman, so Tony gets to work, transforming himself into a woman in time for the Beautify You recruiting conference.

It turns out he's more convincing than he thought, and decides to test out his newly found female wiles on a rich out of town businessman who wants to take her for a night on the town.

How far does he take the charade?