A/N: So probably best to describe the set up just in case it confuses anyone. The story is basically the ramblings of a dying man and he's remembering instances in any old random order and since he wrote them down as soon as he remembered them, so they will be uploaded accordingly. So I thought I'd start with the letter to set the scene for the rest of the story. Anyway here's a detailed Summary although it begins to make sense as the early memories of 27 year old Dean come into it: Sam and Dean were able to stop the YED, but Sam became de-aged and was to have no memory of the hunting life whatsoever, Dean had to raise him again and make some new decisions. One being that he would become the now baby!Sam's father.
So on to the formalities. I do not own any of the supernatural characters, I however do own Robert Steven Winchester (No matter how much like the older Bobby he seems), Jasmine, Katherine and Jacqueline.
Dear Son,
If you're reading this, then I've died. Don't be too upset, it's not the end of the world, I've seen enough to know that there's a flip side. When I came to be your primary carer at 27 I was quite honestly terrified. I remember freaking out and simply running to the woman who I knew could help me, she had always had that maternal instinct, she was like the real world version of Monica, a mother without a child. I'd expected her to be married with at least one kid, but I was only half right, she had the child, but no husband. Turns out his father was a deadbeat and quite honestly the sort of guy that I wanted to wring his neck for leaving her to raise the kid alone. To be fair to the woman, she'd done an amazing job with raising the boy. It's thanks to her that I became the father I did, behind every good man there's an even better woman, remember that.
I knew I was dying a few months ago, I was more tired and I just knew it was time for me to be going soon. I decided to write down everything I could remember about me raising you, even right through your bratty teenage years, perhaps in small part so you know how to deal with it with your own son. That's another thing, the Colt 1911, MY colt 1911, it's yours, keep it away from your son though, I still remember when you stole it that time, how could I ever forget? You were never a bad kid, just hard to handle sometimes. Thing is, I remember worse arguments between my father and younger brother, although to be fair John Winchester was a dick even if he managed to get my record cleared and have it put down as a mistake. If any of what you learned about me and also yourself really makes no sense, please find Chuck Shurley, he's still probably hiding under the name of Carver Edlund. I swear kiddo, you had better find him or I will haunt your ass!
When Ben's away look after the girls and Bobby. I still can't believe your sister had a little boy that had the infamous Robert Steven Singer patented scowl at birth and for the love of all that is vaguely holy, make sure Ben doesn't find his father and put a bullet in him. Like I told the kid, the Jerk isn't worth the jail time, but you know how stubborn the guy is. He did make it to staff sergeant after all, not entirely sure if that's stubbornness or stupidity, probably both to be frank with you.
Always your dad,
Dean John Winchester (Yes I still detest that damned middle name)