Mother-once for Halloween (thinks it was a costume)
Sister-Yes and she knows
SOs-Both of them knew/know and support.
One summer when I was 21 I told a GG friend from high school that I liked to dress. She thought it would be fun to dress me. So, one time I was at her house and every one else were gone. I said to her why don't you dress me now. I shaved my face and she did my makeup. The only dress she had was a mini (I don't really like to wear minis, I would rather wear a long dress). I wore panties, a bra, pantyhose and the mini. Unfortunately, I had short hair, there was not a wig, and my feet were to big to fit into her shoes. But it was sure fun.
While in college, I did not have a costume for a Halloween party. Where I worked, they rented Santa Claus costumes. I picked up a Mr and a Mrs costume. At the last minute, my GG friend went as Mr and I went as Mrs. She lent me panties, nylons, and a bra. Another GG did my makeup and put on beautiful red nail polish, added pearls and clip ons. I still have a picture hidden somewhere. During the party, a couple of girls who dressed as guys had me kiss them on the cheeks to leave lipstick marks. After the party, we went out for ice-cream. My only regret, I wore my own shoes and did not get to wear heelshttp://www.crossdressers.com/forums/images/smilies/sad.gif
she encouraged me to wear pantyhose and matching blue leotards, it was great, she even taught me how to put them on I was in my late teens, and it was great we worked out together