Love triangle that's stabbing my heart

This will take a long story to explain so I'll try my best to explain and get to the point:

There's a guy that I REALLY like! He's awesome, sweet, crazy, strong but fragile, has wonderful eyes and a great smile. We share so many interests. We both like the same animes, comics, and movies. We both even want to have the same job. He's so ambitious in everything he does and he's so hard working. (I'll stop with the description of him because this could go on forever, hehe :icon_redf)

Anyways, I hang out with him as often as I can despite the distance and we are both busy. The thing is though, every time I hang out with him he talks about how he really likes one of my friends (we'll call her Suzy). Just this weekend he told me that he almost asked her out, but he couldn't get the words out. Now my friend Suzy has already turned him down before and she told me if he asks again she's still going to say no. I feel bad for him because I know how he'll feel about it. He always is saying that no one will ever accept him for him. Part of the reason he feels this way is because he's transgender. I could care less if he's transgender. He's himself, and that's all that matters. I like him for him. I like him so much, but he's completely oblivious. Whenever he says something along the lines of "if theres ever a girl that will accept me..." my mind is screaming "HELLO! I'm right here!". I just don't know what to do. I listen to him, hell, I've even got him to talk to me about things he was scared to talk about because I really wanted him to feel better. It's just that he talks about how he's going to try to ask Suzy out, but I just don't know what to do because I know she doesn't like him and I do, but I don't want to screw anything up or overwhelm him. I still really like him, and every time I hear him talk about other girls it feels like arrows are going through my chest. My other friend (we'll call her Hana) told me I should just tell him because she knows he's very oblivious. I just don't want to get shot down though. I want to tell him, but I'm afraid it will get awkward. He's still friends with people that have turned him down before, but I'm still so worried. I also don't know if I should just wait until after he gets turned down again by Suzy because the way he talks to me about it, he's so excited to try again at asking her out. I just don't know how I should go about this.

So sorry for that long story, but I don't know where else to turn. PLEASE, is there anyone that could spare some advise? Please? :help:

 

Any thoughts?