If we don't explicitly define some terms first, we're just going to continue to equivocate. Sex and gender are two different things that you are conflating, and

If we don't explicitly define some terms first, we're just going to continue to equivocate. Sex and gender are two different things that you are conflating, and masculine, feminine, male, and female describe separate things. Sex is purely genitalia. The two extremes are male and female, but this is a spectrum and not a binary. Gender is all the other shit that society piles on top of that. The two extremes in western culture are masculine and feminine, but this is a spectrum and not a binary. That this mostly lines up with the sexual spectrum is an arbitrary decision by society; society could define gender in such a way that it is orthogonal to sex. Examples of where gender doesn't line up with sex in western society include butch within the lgbtq community: http://en.wikipedia.org/wiki/Butch_and_femme http://en.wikipedia.org/wiki/Butch_and_femme. Other societies have in fact defined gender in a way that doesn't line up with sex, so this isn't just theoretical: http://en.wikipedia.org/wiki/Gender_identity#Non-Western_gender_identities http://en.wikipedia.org/wiki/Gender_identity#Non-Western_gen.... In the thought experiment he is not being rejected because of his sex. He is being rejected because of the gender he presents is not sufficiently masculine enough.