Hey! So this is my first multi-chapter fic, although this is more of a two shot. I based this off of a tumblr prompt that I saw, so if it looks familiar that's why. Also please no comments saying that I stole it, i swear that I am just using the idea. I apologise if this is hard to follow or confusing, or if there is bad grammar.

Dear Sam

Look I'm not Homophobic. God, a month and a half ago I would never imagine that these words would exit my lips. I am not saying this phrase like those asshats carrying the confederate flag say it. I don't call people slurs when they are in a moment of weakness only to say that it is just an expression. I don't say I am not gay but… I don't bully people who are gay. I. AM. NOT. LIKE. THAT. I swear.

I even have a gay best friend. God! that doesn't make me sound any better. It makes me sound like someone who couldn't possibly be homophobic because they know a gay person. ' like omg how can you call me gay. I know at least four gay people' Uggggg. I am not like that either I promise.

Charlie is truly my best friend. We met in kindergarten. Well, met is used loosely. She kind of just latched on with a 'sup Winchester, we are best friend now' and that was that. Let me tell you, it wasn't easy. I was a pretty angst filled child. But i'll be damned if she didn't help me through some tough times. And I did the same for her.

That's why I am so confused right now. Charlie is my best friend, I don't care that she is gay, like at all. Hell I even helped her accept herself when her parents wouldn't. I remember her sneaking in and us staying up for hours. I was just always there for her, and things went on as normal.

And i just can't be homophobic. Charlie and her girlfriend are always over my apartment. Omg they are adorable too. They are both so firey and perfect for each other. I have never seen Charlie glow as bright as she does when she is with Dorothy. Funny story, I actually met Dorothy first in class. We were project partners, and she wasted no time in telling me that she was gay, exclusively gay, and only gay, and that if I tried anything that she would break all of my fingers. Then she goes on to list all of the hand bones in the human body. I couldn't help myself. I laughed my ass off.

Now I know what you are thinking. Dean stranger danger run away! But that was not going through my head at all. What I was thinking was, wow this nerd would be perfect for my geek, and they have been together ever since.

This kind of stuff has never bothered me before. Charlie and Dorothy kiss in front of me all the time. Wait, no! That doesn't sound good either. Now I sound like a bastard who fetishizes lesbians, but I swear to all things holy that it is not like that.

Now, once again you may be asking yourself, ' well Dean you sound as un-homophobic as possible, what makes you think otherwise'. Well, its not Charlie, it's Cas. Well Castiel if you want to be technical. Well Dean ' who is Castiel.' awesome question. He is my roommate, and yes, he is gay.

Now this is no problem. I actually asked him if he was okay with gay people, as you know, part of the interview process. And yeah, I know that the question is personal for the first interview, but you have no idea just how many people went on ten minute rants about the filth that is ruining marriage, or about how hot lesbians are. I took great pleasure in absolutely shredding those applications. And setting them on fire. And letting your dog shit on them. Thanks for that by the way. And then lighting that on fire. So yeah I am not homophobic. Just to clarify.

Anyway, I was asking for Charlies benefit. I would never, ever, ever want to make her uncomfortable with being herself under my roof.

So, back to Cas. When I got to that question, he couldn't have had a more perfect answer, it wasn't until I was narrowing down to my top two applicants that he confided that he himself was actually gay. At first it was fine, I mean cool, gay roomate. I don't really care. You do you.

But like I said, at first it was fine. But then he brought his boyfriend over. His boyfriend was a reasonably nice guy. Always polite, always making sure everything was okay with me. Like when they would bring friends over. It was all fine. Hell, even Charlie liked them. They would go on double dates at least bi-weekly. And it was all fine. Okay, maybe I was a little lonely but I swear to jesus that that was it.

About a month in to Cas living here they broke up. Cas was devastated. I mean truly devastated. He wouldn't eat, he wouldn't sleep. He wouldn't even come out of his stupid freaking room. I was just so angry at his boyfriend. But still, not in a homophobic way. More like in a you screwed with my friend, prepare to die way.

The homophobic part came in about two weeks after the break up where Cas started, um, dating around. At this point he was one of my best friends. I didn't want to see him get hurt. I get it, I do. Rebounding is a completely normal way of getting over a long term relationship. I've done it, Charlie has done it, you have done it. Again, it is completely normal.

But then, whenever I would see Cas, um having relations with guys, oh not that you perverts! I mean kissing. I would get these feelings. It's like a hot, white anger in my stomach. It makes me feel sick, and disgusted, and just itching for a fight. And it just gets worse every time he does it.

Is this some kind of deep rooted homophobia that my dad gave me. Is it possible for it to kick in later in life? Is it genetic?

And I have been so rude to Cas. I've been snapping at him, and just overall being a shitty roomate. Everytime he has a guy over I just slam the door to my room. I just can't help myself. Everytime I do I just feel so bad, but I can't stop.

God I should talk to him about it shouldn't I. If I am having ugly thoughts about him he should know. That's it! Tomorrow morning I am talking with him about this. I need to fix this

Dean

Chapter 2 will explore the conversation between Cas and Dean. It will be written in present tense in Dean's point of view. Thanks for reading. Once again this is based off of something that I saw on tumblr so please don't comment that you have seen this before, or that I am stealing this. I am just using the idea.