Sixty years ago this past weekend, Christine Jorgensen became one of the first people to be widely known to have undergone gender reassignment surgery.
The Christine Jorgensen site:
http://www.christinejorgensen.org/ - the site's introduction page has a clip of a press conference from when Christine returned to the US after her surgery in Denmark.
The earliest know male to female transition, including surgery, was that of Lili Elbe
The first female to male trans person to under phalloplasty was Dr Michael Dillon