This is how I did it. I had changed *a lot* when I got confronted by any of my family. My sister asked me I had breasts, and had women's clothing on eventually :-) . My parents were, seeming, still however extremely shocked by it. They said I had never been femine (despite my having long hair and nails throughout my childhood), which was quite funny as they had just failed to spot that their make up wearing, women's clothing wearing, jewellery clad, high heeled, noticeably breast displaying 'son' had gender issues. lol. I didn't really *trust* their trans spotting opinion as such! lol
I Anywhooz, at home I wore whatever I liked but publicly, I started with nail polish, then, eyes, femmed my clothes, and accessories and slowly started emphasising my breasts, then full make up with contouring. I came out to my friends at different stages throughout and let my family ask (as I wanted to get them used to it - like you). Finally I came out at work. I was surprised by the fact there were a good few who hadn't figured it out and thought I was just 'eccentric'.