This is my wife of 15 years and a mom of 10 who has been very shy and reserved most of her life. So when we had a chance to get away by ourselves for a weekend I tried to get her to open up.
After a swim I was able to get her to loosen up and let me take pictures of her body in her one piece bathing suit.
Feeling good that day, she even took her top down while she tanned but kept her boobs pressed down to the chair. A very good start for her.
Hopefully with your help, she will be more willing to show next dare.