I've just been catching up on the cable series "The Riches" at Hulu.com and only after 3 episodes have realized that one of the members of the family of thieves is a young crossdresser. The series is about a family of "travelers"-- Irish descendants who cruise the country like gypsies. The premise is that they try to settle down among upper income suburbanites. The show is very good and I recommend it.

The youngest of the family, Sam seems to wear mostly boy's clothing with feminine touches. I honestly have not determined from the story what the kid's gender is and, in fact, in the opening setup, the father says they have "a boy, a girl, and uh...".

The Advocate article below clears that issue up. In fact, one of the shows producers is openly a crossdresser himself. It says he has been "arguing to critics for years that straight ->-bleeped-<-s like himself do exist".

http://www.hulu.com/the-riches
http://www.advocate.com/exclusive_detail_ektid43241.asp