Originally Posted by Sands

Depends on whether you define gender in mental or physical terms. Psychologically, transsexuals are the opposite gender and seek to change their physical makeup to reflect that. To further complicate the question, imagine you meet and fuck a post-op transsexual. You never find out that he or she used to be a she or he. Are they a man or woman? The Turing Test creates a standard to define "intelligence" when dealing with machines. If a person can't tell that a machine is a machine through the course of a conversation, then according to the Turing Test, that machine has intelligence. If you can't tell you're fucking a transsexual, have they passed some sort of gender test? Can you argue that there's a concrete, non-subjective reality in which they will always be considered their original gender? Some may offer simple answers like, "Yes, once a [gender], always a [gender]," or "You are what you think you are," but the real question to be asked is a question that GFY has been asking since it's creation:

Would you hit it?