The Chicago Tribune deserves a bit of note for publishing several articles about transpeople today. The first is called Transgender people fight for civil rights, public understanding, written by Rex. W. Huppke. It focuses on transmen Dan Charmichael, who served in the Iraq War before transitioning and goes on from there to cover a lot of ground.
Despite progress, discrimination still a problem for those whose gender identity doesn't match anatomical sex
Huppke wrote a second article, Finding their gender identities, featuring transman Andre Perez, founder of the Trans Oral History Project and transwomen Candice Hart and Nathan "Precious" Davis.
All four of the these transfolk appear in the video Being transgender, available here (sorry, there is no embed code).
An attempt at explaining transgender is available in Defining transgender, which also contains some very brief history. Huppke also addresses some of the fequent questions asked in Questions and answers and provides some resources.
For a more personal look at the transition process, transman Owen Middleton is documenting his transition on youtube. The linked article is at Unicorn Booty, but you can also access Owen's youtube channel here.
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