Can a transgender woman who had feminine facial surgery get a deductible on it and if so what documents do I need?

[AlanT]

Yes.  Gender identity disorder is listed in the American Psychiatric Association’s Diagnostic and Statistical Manual of Mental Disorders. Since it is a recognized medical condition, costs for treatment — that is, transitioning from one gender to another — are allowable medical tax deductions.

You would report your medical expenses on Schedule A, like any other medical expense.