Just after recently figuring out that I was transsexual, its made me look at other people differently, and its made me think!  Anyway, I have this friend that I have known for almost 10 years! We met since we were 5 in school, and were pretty much the best of friends. Her and I were really similar, always seen as the "tomboys" of our class

We both had short hair and wore boyish clothes to some extent. Looking back now, I remember the games we used to play during school lunchtimes. She always chose to be the male character as well. There was one time where she did some drawing of two bears in probably grade 4, of me and her. She drew her self as the boy bear and me of the girl one in the dress (I wasn't really happy about that , but I didn't say anything back then )

Now that we both go to different schools, I dont see her as often, but I still wonder, and am really curious! I remember 3 years back, her brothers friend made fun of her saying that she had said she "wanted to be a man" when she grew up. Im not too sure if this is true!  

I met up with her 2 or so months ago, she was still her usual self. Male type clothes and short hair. Im not out to her yet, she has nooo idea that I feel this way, but Im really curious to find out if she is too! I want to ask her something, but just don't know how to do it. Maybe we are both suffering from the same thing and all those years haven't noticed! I could ask her if given a choice, what gender would she have chosen? I just dont wanna make this awkward

"When you hear hoofbeats, think horses, not zebras."

It's more likely that your friend is a masculine female than transgender.  I would be cautious asking anyone outright (especially since you don't see each other as often) how they identify.  It's highly possible that a direct question would offend her.  But if hypothetical questions ("what if's") are something you guys do, your example (what gender would she have chosen) might work.

Does she know about your trans status?  If not, test the waters by telling her (if you're comfortable) and see what she thinks and feels about it.  Sometimes people need to know they aren't alone to come out.

I had a friend who's a very masculine woman, grows a better beard than me, shaved her head could easily (and does from time to time) pass for a man. But she is very much a woman and has from time to time gotten offended when someone asks if she is ftm or taking hormones to look more masculine. The point is she identifies as a masculine woman though it's easy to think that she may be ftm.

You definitely need to be careful in how you approach your friend with this subject. Because no matter how well meaning you may be she may take offense if it seems that you are making an assumption about her.