Transgendered halakhic challenge

TEMPLE MOUNT WATCH: Transgender woman denied entry to Western Wall. After being denied entry to the women's section of the Western Wall, Kay Long approached the men's section only to be yelled at and told to enter the section that had already rejected her (Dr. Ruchama Weiss, YNetNews.com). Life in the twenty-first century is complicated. I wonder what the Talmudic sages would have made of this story.