Perhaps smaller steps, such as wearing dresses around people you trust, would help you to feel more comfortable. I don't know, having never gone through what you are undertaking, but it was the first thing that came to mind... I suppose there is a very good chance that you have already considered this, and may indeed already have acted on it, but I thought I would mention it just the same.

Anyhow, I'm not sure if you would consider me one of those people (who you trust), but I don't really mind what clothes people wear as long as they don't contain messages of hate, and I would be happy to be there anytime you'd like. Self acceptance and understanding is a beautiful and humbling process whether one is going through it themselves or seeing someone else go through it.