I'm going to just skip a lot of stuff and jump to the point:
If you are going out in public wearing dresses (sexy or not), you are going to need breasts, butt and hair. A man in a dress looks like a man in a dress, period. Buy yourself a good pair of appropriately sized breast forms. Buy your self a good pair of hip and butt pads. Buy yourself a realistic looking wig.
Learn how to shave and cover your beard shadow and learn how to select and apply makeup.
Note: Buy your breast forms and hip/butt pads before you buy your clothes. What fits without the padding won't fit with the feminine figure you are creating.