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Now I don't think it's out of bounds for a person to not tell someone this at the start of dating, because first impressions are very big, and one has more to offer than the details of their gender.
I would have to very strongly disagree.
Not that I'm in the market anyway, having been married now for nearly eighteen years, but if I was still in the dating scene, I would have to consider it a very serious breach of trust for someone who is not really female to pass himself off as female in order to deceive me into initiating a dating relationship with him. No matter what he calls himself, no matter what anyone else calls him; a man who has been surgically-mutilated to appear female is not female, and not in any way a suitable romantic interest for a heterosexual male.