Worried

For as impossible as I find it to keep friends for more than perhaps a month, I've had my Best Friend since I was 12. We went to middle school together and, as is obligatory in (what used to be) opposite-sex friendships, I was in love with him for a good 3 or 4 years. We lost our virginity to each other, have gone climbing on rooftops in our hometown, and even broken into my church to play strip poker (he's the only person I've ever been so rebellious with!). I still absolutely adore the kid, and have been so blessed to get to watch him mature from the sweet homeschooler I met through his very very cruel and hurt stage to the wonderful man he is now. He speaks in riddles and sarcasm and I love him for exactly who he is. I'd reckon that, even with as little as he tells me, I know more about him than just about anyone. He recently randomly moved to Oklahoma for school, and, even though I hadn't seen him in probably a year, I feel his absence now a lot more acutely.

He grew up in a very redneck family. His father is an abusive ass, and his mother, whom I adore, keeps her mouth shut and lies low. He's nearly as racist as his father, and I'm sure homophobia ran rampant in the household. Yet, he never once batted an eye when I came out as a dyke, got engaged to a girl, and cut off all my hair. He never stopped treating me like his best friend; I'm not sure I have words for how much I value that.

He's coming back home for the holidays, and we've made plans for him to come up north to my apartment for a few days to sightsee and catch up. I'm ecstatic to see him. But good Lord am I beyond petrified. I haven't come out to him as trans. He and I, even though I'm only physically attracted to women, have always had the flirty friendship that comes with being so close to someone and having hooked up before. I'm not extraordinarily eager to change that, but how will my coming out affect it? Will this be the time his closed-minded upbringing rears its ugly head? He still very much views me as his female best friend who he flirts and cuddles with and complains about girl problems to. How do I tell him that I'm becoming some sort of a guy, who still wouldn't mind cuddling with him? I can't not come out; it's a bit obvious with my male clothes, refusal to shave, and attempting to switch to a new name. I don't see him really /getting/ it, which I suppose shouldn't seem so bad, but it's like salt in a wound every time he says "Hey girly!" I guess it comes down to whether I value his friendship or my gender identity more at this point. I can't help but feel, even if he can sweep it under the rug for now though, that it's a ticking timebomb. What will he make of me after surgery and testosterone have undeniably made me male like him? Will I still be his best friend? It terrifies me to look forward into the future without being able to guarantee he'll still be there with me.