I think giving the impression of being conservative is sometimes a safe haven for women. When I first starting dating my wife, before she knew me well, she was a lot less daring than she is now. After getting to know me, she wore a largely open shirt and no bra to a party and received a lot of positive comments from both men and women. I loved it and made sure she knew it. She almost never wears a bra and I would venture that most of my friends have seen her nipples either directly or through see through clothing. I'd say that if you give her some indication that you're enjoying the show and not judging her for it, she'll open right up. Her last surprise for me was when I had to pick her up at home to go shopping. She came to the window, threw the camera at me and said 'do you like what you see?' ... - Max