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There's no two ways about it: if you're going to look female you've got to have a bustline. Unless you're fortunate enough to grow your own, you'll need some way of simulating breasts. Either way you're almost certainly going to need a bra or two in your feminine wardrobe. If you have breasts or breast forms, you'll need one to hold them up; if you've got enough up front to make some cleavage, you'll need one to help lift and shape.
Buying a bra generally involves three problems: determining the right size, selecting a suitable style and actually going and buying one.
Filling your bra is another matter entirely. Assuming for the moment that your cleavage is not a naturally occurring phenomenon, there are a number of ways to produce a pleasing, convincing bust.
We'll tackle each of these step by step: