How to ask this boy out?

I'm thinking about asking a boy out soon, but I'm scared of what he'll think of me being trans. I'm not out to anyone at school and I don't want to be out yet, and because of that I know he sees me as a girl. And he's said before that he's not gay, which sort of still gives me a chance (since he thinks I'm a girl) but I'm scared that would he would not take the 'im a trans boy' news too well. I don't want coming out to him to mean he starts looking at me different. I know that if I came out well into our relationship he'd probably accept me but it still scares me. (Canada) 

FTM in drag

I feel like I can never do drag because I'm ftm and people will say I'm cheating because I was born female.

[Alexander, Canada]
 

In love with roommate's girlfriend

I’ve fallen for my Best friend’s gf. This best friend also happens to be my roommate. My room is right next to his and I can hear them having sex almost every night. It sucks because she is so supportive of both of us and our transitions. Why does she have to be so perfect?! I just want to not be attracted to her and to go back to not noticing her.

[Cal, Canada]