Before I dressed as myself infront of family members, I showed them pictures of me dressed up first so they had an idea of what I looked like and it wasn't as much of a shock for them. To me it was kind of ridiculous on why they are so shocked or whatever but it is what it is. I guess even if it's uncomfortable at first just don't act like its a big deal because then it will seem like a big deal. The first time I dressed infront of the family members I'm not close to I kept it classy but also made sure I showed my feminity, this showed them that I was ment to do this. After the first time dress however the hell you want and they shouldn't have anything to say bevause if they do then anybody can point fingers at others for how they dress trans or not so it shouldn't be an issue. Some people feel excited the first time some people feel awkward it just depends on if the person is open or closed minded so don't take it personal! I have had people in my far side of the family give me the stares but I just kept in my mind that I'm happy I'm brave enough to be myself and I love myself that I'm transitioning, this kept me in a positive mind frame. Good luck !