Sure. If you wear a plus size like I do you might want to check out Trendy Plus Size Clothing for Full-Figured Women | AshleyStewart.com If you need to figure out what size you wear, check out this link: Susan's Place Transgender Resources for Transsexuals and Crossdressers: Library: Opposite Sex Size? By the way, I recently ordered my first female shirt, until recently I've only had female accessories.
I think it's because it can be a bit scary to do it for the first time, and it helps to have other people to convince you you're doing the right things.
Yes, definitely! I don't see any reason why you shouldn't buy a dress. I have all different lengths of dresses. I have a few long summery style dresses, a few knee length (cocktail style dresses and summery dresses), and I have a few mini dresses. As for what length to go for it all depends on what you are comfortable wearing, and where you plan on wearing it. My suggestion, just check around and see what styles you like. If you like it, buy it =)
Have you thought of buying second hand? That way, you could get a few instead of one... Another advantage is it will not change its size... sometimes if you buy new you cannot tell if it shrinks a bit after the first wash or not. And often in secondhand stores, people don't look much and its not really sorted by gender... I'd buy from reputable sorces though, they usualy wash it once before they sell it.