Authors note:

About half an hour ago I just had this urge to write some of my memories down, only I wanted the speckled and embellished with Winchesters. I think there was this pull because thinking back to certain times in my childhood I realized that there were quite a few times where I found myself in company of either two brothers or two boys who were as close as brothers. And each time one was light haired an the other dark haired. It's all probably a coincidence due to me moving around so much, but when I watch the Winchesters now I let my imagination do the work.
All the things I mention here, some pleasant, some not. Have happened to me at some point in my life, the only difference is I am substituting the people with the characters we know and love.

This is my first time doing anything like this so please let me know what you think about it in the comments and if I should stop or keep it up.

Chapter 1: He didn't have to smile at me twice

I realize now, they probably moved around as much as I did, if not more. The first time I ran into them I was seven, and since that day they have come and gone from my life unexpectedly, randomly and surely unintentionally?

Back then I rarely ever took the right way home at the end of the school day. You know, the one that all the normal kids walked, through the town. Instead I would take a dead end road, hop a measly fence and find myself on a hill overlooking the small town and the river winding under it. To me being up here was breath taking, and I didn't mind trekking through knee high grass and over the sloping hills which followed the curves of the river below.

I was feeling so cross that day, and over what? Homework of all things. The assignment? Draw a picture of your school route. I did. And then I got no credit. Why? My picture was of a beaten path overlooking the town, while all the other kids had streets and buildings in theirs. "Imagination is nice", the teacher said, "but don't let it run wild."

Run wild?! I silently fumed as I walked. The entire time holding up the drawing in front of my face, comparing it to the things I passed. "But I even got that stack of hayyoooww!" I yelped after stepping on a hidden branch only to have it snap up and smack the side of my leg. I bent down to toss the branch away when I heard a hiss, and you don't have to hiss at me twice. I probably started running before my brain even fully computed that I was dealing with a viper.
I slowed down when I came round the bend of the next hill. I knew this spot. If I plop down just to the left of the overgrown path I will land smack dab in the middle of a strawberry patch. "Hmmm don't mind if I do" I huffed out, still winded, as I went to sit down and then I froze.
I ran right past him. I didn't even notice him lying there, in the grass, his arms folded behind his head.

Time stood still as I took him in. He wasn't handsome, I didn't even know what handsome was at that age. No, not yet... but he would be, he'd grow into it.

All my childish brain could tell me, in my frightened state, was that he was soo cool, of course he was, he was older! I thought as I mentally approved of the ripped jeans and the faded old shirt. There was a metal head of some sort hanging off the chord around his neck, I wanted to reach out and grab it. He had freckles scattered across his face... it was so still.

I must have stood there staring for a few seconds at least but he hasn't moved a single muscle. He must be asleep... right? "Oh my god! What if he is dead?!" I didn't realize my thinking had turned into whispering. The crunch of the paper as my fist tightened around it must have snapped me out of my haze.

Suddenly I felt fear again, at the fact that he had startled me, the fact that there is no one else around and why was he still asleep? Surely I would have woken him up by now? And then pure panic set in as I watched his face, his eyes still shut, but his mouth had turned up into a smile.. and well, he didn't have to smile at me twice. Once again I was running. I looked back once, when I heard him say "Hold on kitten", only to see a crop of messy blond hair sticking out from the grass as he sat up. But I didn't stop, I ran faster.