Disclaimer: I don't own Supernatural
Trigger warning: Major Character Death; Loss of a child, and a significant other.
When Sam Winchester was nineteen he moved into an apartment with his girlfriend Jess.
They had been dating since they first met fall semester freshmen year, back when they were both eighteen, and they hadn't thought of separating once.
In fact they hadn't been away from each other for more than a week at a time since then.
So they had rented an apartment on campus from a group that catered to college students, figuring it would be easier and cheaper than switching off between dorms and apartments every few nights like they had been doing before. Sam and Jess had both gotten jobs to pay for the rent and they had formed a cozy little nest of their own, that they were proud to call home. When the time came for summer, they had visited her parents but decided to renew their contract and keep the apartment for the upcoming summer, and year instead of moving back into the house Jess grew up in.
Sam Winchester was twenty one when he got engaged to Jessica.
It was a week before the summer had ended that Sam asked for the blessing of Jess' family in proposing to her.
Jess' mom had been ecstatic, and had made Sam cry in happiness.
He had fallen back on his old talent of hustling pool so that he could bring in enough money each week to keep paying for everything while still saving up on a ring.
Eventually he had bought an old one from a small store in Palo Alto with vintage jewelry, and had been given a surprisingly good price.
So despite having only known each other for three years, Sam asked Jess to marry him and she had said yes without hesitation. They had agreed to a long engagement, deciding to not get married until they were done with their initial four years.
Sam Winchester was twenty two when Jess told him she was pregnant.
They hadn't been expecting it and it wasn't the best of timing, but they knew they could raise their baby, loved and happy and that's what mattered to them.
Sam started hustling pool again as often as he could, this time for the house they were going to eventually need.
They asked to be surprised on the gender during their appointments, and decided that if it was a girl they would name her after Sam's family, and if it was a boy they would name him after Jess'.
Sam painted their second room yellow and grey, and built a rocking chair from wood he got cheap at a lumbar yard.
A week later his brother showed up, and despite his worry about his fiancé Sam went to search for his father.
They both chose to ignore the dreams that Sam kept having, Sam believing he was projecting his mental image of his dead mother onto his pregnant fiancé, and Dean knowing better than to ask.
But then Jess was on the ceiling burning, and Dean was dragging him out, and all Sam could think of was the horrible tearing pain in his chest as he saw his world go up in smoke.
It was only later that Sam told Dean about the baby, Jess and him having agreed when they found out that they wouldn't be telling anyone before the end of the second trimester.
Dean had to hold Sam as he yelled in pain over his lost family, in the parking lot of his burning apartment building.
Jess' parents found out about the baby after the autopsy. They told Sam it wasn't his fault, that they were glad that their daughter hadn't died alone, and that the two, would have been amazing parents. That they were glad that they got to be grand parents.
The day before the funeral Sam made Dean drive him to the OBGYN that Jess had chosen.
Sam Winchester was twenty two when he found out that he had lost a daughter with his beloved Jess.
He ended up curled up around Dean for the rest of the day.
Dean cried with him.
Sam Winchester was twenty two when he buried his fiancé and his baby.
The baby they had loved so much, so soon. The baby that Sam still kept finding himself wondering about, and who's ultrasound pictures made their way into all the Winchester wallets and through out the Impala.
Mary Deanna Winchester never reached one year old.
I may add a spin off of this in which Mary lives and the boys take care of her but I haven't decided yet. Let me know what you think of this story and my secondary idea in the reviews!