Could it be that the friends an family you talk to have a bit of an agenda? Not in a malicious way, just subconciously wanting to see more feminine then masculine?
But to reassure what others said here: T works miracles :p I've seen before pictures of guys that completely shocked me because now they look like cavemen :p
I actually think you look pretty good in the first picture, leaning towards more male in my eyes even. I think the shorter hair really works for you. And expression does matter, I feel I pass easier when I look angry/serious then when I'm happy and smiling. However since two months I've also passed when happy and smiley :p But if you intend to get on T sometime it will defenitely help you pass a bit better. In the end I get the impression that guys on T will pass at some point, for some it takes a bit longer but I think most will pass eventually.