April 22nd excerpt: 

“Didn’t we go over that I’m not that big for a human?” Dean asked, poking Bowman in the side. “I don’t cause earthquakes if I fall over!”

“Hey, watch it, giant!” Bowman groused, rustling his wings irritably. “You are plenty big for a human! You’re over six feet tall!”

“And don’t you forget it, small fry,” Dean shot right back, grabbing a few more chips in his hand. “It feels good to be the tallest.”

April 21st excerpt:

Dean grabbed a water bottle out of the fridge. He was definitely thirsty. He managed to down most of the bottle before he dropped it down.

Jacob stepped back from where the tower of clear plastic landed. At least there was one advantage to being the smallest one there. When Jacob’s eyes widened slightly at the sight of how much water Dean had gulped down in one go, no one noticed.

April 20th excerpt:

Sam drove the final nail in the coffin of his stubborn resistance. “Dean,” he said gently, sitting on the edge of his book with his legs dangling off. “None of us can drive the Impala. If you run yourself into the ground, we’ll be helpless. Please, just eat something.” His eyes, even as small as he was, were wide and round, staring up at Dean beseechingly.

April 19th excerpt:

Dean tried to glare at all of them, but it didn’t work while being ganged up on from three different directions. Sam on his own was bad enough. “I’m fine,” he repeated stubbornly, digging in his heels from sheer cussedness. “I’m just… not hungry, alright?”

His stomach disagreed with him, grumbling in aggravation. Dean glared downwards, annoyed with the internal betrayal of his stubborn stance.

Traitor.

April 18th excerpt:

Later on, Bowman had to dodge a surprise projectile, a small ball of paper crumpled up and flicked at him by Dean, seeking a momentary reprieve from the constant tedium of research. Bowman, naturally, was easily riled up by this action and retaliated by retrieving the paper and lobbing it right back at the human, much to Jacob’s entertainment.

Sam rolled his eyes as Dean, a mischievous glint in his eyes, snatched the paper right out of the air, snapping it back at Bowman before the sprite had time to recover from his own throw. Bowman lucked out this time, the shot going wide and missing by a good few inches.

April 17th excerpt:

The ride was uneventful. Jacob remained in Sam’s bag, finding it simpler than trying to climb out only to be rolled around in the pocket by every little movement. Despite feeling silly huddled in the satchel, he felt a lot more secure that way.

Even if it meant he was stuck on Sam’s lap while he dozed, fluffy brown bangs covering his eyes.

April 16th excerpt: 

Jacob looked up in awe. Dean’s boot alone would be impossible to see over. Hell, just the rubber sole was almost as high up as Jacob’s current stature. The towering, jean-clad leg above the boot stretched high overhead. Jacob could scarcely imagine what it’d look like to see Dean standing from a view near his feet. The thought almost gave him vertigo and Jacob had to stare at his knees for a few seconds to let the moment pass.

Unbothered by the size of the boots and the limb before him, Sam came right up to the heel and started the easy climb up to Dean’s knee. He scrambled up the towering leg, fingers easily finding purchase in the thick threads. Jacob was amazed by how quickly Sam climbed up that tower of denim. It was practically second nature to the guy after spending a year around humans. Jacob could even recall a time or two when Sam had climbed up his leg like that.

April 15th excerpt: 

He looked over and saw that Bowman was smiling faintly at him. “Oh, what? You’re just jealous you don’t have a portable Jacob to carry around,” he quipped, earning a tired snicker from the sprite.

“Oh, it’s really too bad we can’t make your picture. Rischa would just shriek if she saw this,” Bowman teased.

April 14th excerpt:

There was more than enough room for Jacob inside, but Sam took a few extra items out, leaving his journal along with the spare key for the panic room tucked inside the pages like a bookmark and a few other small supplies.

Jacob pursed his lips at the bag while he considered it. Sam was offering, but Jacob was fairly certain it’d be insisted upon, based on the conviction in his eyes. He couldn’t refuse; he was sore as hell and walking around did not sound very appealing. Every step for Sam or Bowman took three or four of Jacob’s. He had a lot of ground to cover just to get out from under the seat.

According to the timeline I was thinking of, Bowman would be about 20. Putting Jacob at 18 or 19. My characters are younger than the bros, and though Bowman doesn’t really care about age at all, it leads to a dynamic with Jacob looking up to the Winchesters (no matter what size everyone is).