To boob or not to boob?
Let me first state the obvious: trans women are not born with boobs. I wish I had been, but I wasn't! Some of us may develop something of a cup size if we are on hormone therapy. But if we are hoping for boom-bang cleavage, then we need to know that it isn't coming naturally. That doesn't mean you need a boob job, necessarily — a great bra can really make a difference in the self-confidence department. I found padded bras to be much better than push-up bras (there wasn't a whole lot to push up) to give me the shape that made me look as good as I felt.
Naturally, cis women experience the same cup-sized concerns, while some trans women are perfectly happy not wanting to look like a Victoria's Secret model. I suppose it did seem a little strange wearing a bra initially, but even though I didn't have a classic hourglass figure, it definitely helped enhance my feeling of femininity.