If you have a recommendation about great speculative fiction which explores gender in some way, please send the recommendation to the Tiptree Award jury. They’re reading now for works first published (as a book -- or possibly an e-book) in 2015 only.

http://tiptree.org/recommend-works-for-the-2015-james-tiptre...

James Tiptree, Jr., as you may or may not know, was a woman.

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Wikipedia Entry:

James Tiptree, Jr.
Alice B. Sheldon
Born Alice Hastings Bradley
August 24, 1915
Chicago, Illinois, U.S.
Died May 19, 1987 (aged 71)
McLean, Virginia, U.S.
Pen name James Tiptree, Jr.
Raccoona Sheldon
Occupation Artist, intelligence analyst, research psychologist, writer
Nationality American
Education BA, American University
PhD, George Washington U.
Period 1968–1988 (new fiction)[1]
Genre Science fiction
Spouse William Davey (1934–1941)
Huntington D. Sheldon (1945–1987, their deaths)
Relatives Mary Hastings Bradley (mother)
Herbert Edwin Bradley (father)
Alice Bradley Sheldon (August 24, 1915 – May 19, 1987) was an American science fiction author better known as James Tiptree, Jr., a pen name she used from 1967 to her death. From 1974 to 1977 she also used the pen name Raccoona Sheldon. She was most notable for breaking down the barriers between writing perceived as inherently "male" or "female" — it was not publicly known until 1977 that James Tiptree, Jr. was a woman.