This may and may not be a first, but a transgendered person has been elected mayor of Silverton, Oregon. Stu Rasmussen, who's been elected to the office before, was elected in while openly presenting himself in a feminine visage. He says he identifies himself mostly as male, but has breast implants and wears women's wear. I totally congratulate him for chipping away at the public stereotype. We should all be so brave.
Lyric
http://www.kgw.com/news-local/stories/kgw_110608_news_transgender_mayor.18a1f2fa7.html (http://www.kgw.com/news-local/stories/kgw_110608_news_transgender_mayor.18a1f2fa7.html)