Christine Jorgensen

Sixty years ago this past weekend, Christine Jorgensen became one of the first people to be widely known to have undergone gender reassignment surgery.

http://www.bbc.co.uk/news/magazine-20544095

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.

Other sources:
http://en.wikipedia.org/wiki/Christine_Jorgensen
http://library.transgenderzone.com/?page_id=2160

Earlier cases:
The earliest know male to female transition, including surgery, was that of Lili Elbe
http://en.wikipedia.org/wiki/Lili_Elbe

The first female to male trans person to under phalloplasty was Dr Michael Dillon
http://en.wikipedia.org/wiki/Michael_Dillon