Most likely not, if by shemale you mean a male who takes estrogen and resembles a female but still possesses a penis. I'm not gay, not that it really matters. I fully support gay rights, I'm just not interested in sex with a person who is physically a dude.
If a person of the male sex had trans-gender surgery to become, for all intents and purposes, female, then yes, I would have sex with aforementioned person.
If a person of the male sex had trans-gender surgery to become, for all intents and purposes, female, then yes, I would have sex with aforementioned person.
What falls away is always, and is near.
Also, I am not pretending to be female, this profile picture is my wonderful girlfriend. XD