Well, My life is probably going to get a lot more interesting in a few weeks...
My little sister and I have always been very close. She's 5 years younger and is my only sibling. But so far, in the couple of years since I started crossdressing, the concept of me finding and exploring my feminine aspect has yet to come up between us.
At first, I was literally half a continent away, so she would never be in a position to see me en-femme. So no reason, really, to tell her. But my 20 year old daughter and I just moved to a new house that is only an hour and a half's drive from where my sister lives, and... My sister's just volunteered to come down in a couple weeks and stay for several days, to help my daughter and I to get settled in - and also to bring a cat for my daughter...
So... my daughter and I will have the next two weeks to offload our cargo containers and get most of what is in the house unboxed and sorted out. Including a lot of boxes that are very clearly labeled as "Ceera's Clothes", "Ceera's Shoes", etc..
And even if I have all those girly things unpacked, one of my two dressers will be filled with girl clothes, and half my walk in closet will be girl clothes, and in my bathroom there will be wigs and makeup and perfume... And I can't pass them off as being my daughter's things, as she has her own bedroom and bathroom and closet on the other side of the house, and doesn't wear my size clothes or shoes.
And then there's the fact that my nails are done, my ears are pierced, and my eyebrows waxed...
So... It seems inevitable that before my sister's visit if over, she's going to find out that her beloved big brother is occasionally her big sister!
I hadn't planned on letting her know about the feminine side of me quite so soon, but... well, at least it will just be her, by herself, and not also her husband and 4 kids!
I don't plan to be hiding anything from my new neighbors. I've been en-femme at our temporary apartment and running around downtown for most of the day today, and most likely will go to the new house this evening en-femme for the first time, as my daughter and I continue moving things into our new home. I don't want to hide it from my sister, either.
I'm fairly certain that it will surprise her, but that she will accept it after the shock wears off. We love each other quite deeply, and I doubt this reveal could shake the bond between us. I hope...