Just sometime a friend of mine and I thought up.
Disclaimer: I got nuthin
Hotels Have Two Beds
It's said that children don't realize their life is any different from anyone else's, that is, until someone tells them. In the case of Dean and Sam Winchester, they knew hotel rooms. Since Sam was an infant, they hadn't lived in an actual house. Instead, the small family (consisting of Dean, Sam, and their father, John) slept in motel rooms.
They slept in cheap motel rooms.
More often than not, the beds had bedbugs or some other parasite. The showers were moldy. The water was cold. The television only got two channels. The rooms smelled of cigarette smoke, despite the room being advertised as "Smoke Free."
When one lived on the road, living in horrible motels were sometime one learned to deal with.
Despite the numerous flawed rooms the Winchesters frequented, they all had one thing in common. All rooms generally had two beds.
Now, normally this wouldn't be a problem. However, most people didn't live on the road with two small boys. Those two boys had grown accustomed to the motel rooms. In Dean's case, he barely remembered what it was like to sleep in the same bed every night. Sam, he didn't remember at all.
Due to the circumstances, Dean and Sam often slept in the same bed during their youth with their father occupying the other. And Sam, being the child afraid of the dark, would often cuddle up to his big brother in the middle of the night, looking for support. He was always safe with Dean next to him. Being the older sibling, Dean didn't mind. He took comfort in his little brother sleeping close to him.
Most children fall asleep to lullabies. Since they'd begun their life on the road, Dean's lullaby was Sam breathing deeply, safe in dreams where the monsters couldn't touch him. And while his little brother slept, until he himself fell asleep, Dean slept with one hand on Sam, the other on the gun under his pillow.
He wouldn't let anyone – or anything – touch his baby brother. Not ever.