(I always wondered about Cas' hair cut in S5, I mean obviously it was Misha but hey…It's my fanon so… PS this was written on my iPod so sorry for any mistakes ahead of time)
Castiel notes with great interest how much a human's opinion and judgment weigh upon appearance. The clean cut, bright men and women with lupine smiles and a prowl to match seem to control those with the frumpy appearances and lost expressions upon their puckered and drawn features. Castiel falls into the latter category, he just knows it, but it's Dean and Sam that hold him captive always.
He's seen them in suits much more crisp and sharp than Jimmy's own rumpled and worn down one. Shoes that shone like oil slicks across water. Ties that stood stark and bright across their chest much unlike his own that lay askew and knotted like a child's. Other times the Winchester brothers made statements in boxed, familiar plaid and worn thin jeans with frays and rips that share stories Castiel couldn't interpret with all his celestial knowledge. It's just not clothing, either, Castiel knows. It's the way Sam's teeth peek out oh-so-playfully whenever he laughs or smiles as bright as the sun. Or it's the way Dean's eyes crinkle when he speaks and his eyes turn up and shine. The way Sam let's his hair fall to his shoulders and Dean keeps a fine layer of stubble across his strong, firm jawline.
So Castiel will look at Jimmy and try not to fidget and tear and pick and pull and fix. He'll try to ignore the hang of the trench coat across his slender shoulders. The way the tie hangs uselessly at his neck like a long forgotten noose. The way his lips are torn and sometimes unable to form the right words. How his brow furrows and leaves more lines upon his tall brow. Even how his eyes seem to drill through the glass of the mirror and back at him. Lastly, Cas will try not to muss at Jimmy's hair. It's an utter mess, all wind blown and tangled into wicked knots. It sticks up and makes its own statement and leaves Castiel in a state of dismay and shock.
Cas really can't help it when he hunkers into Dean and Sam's shared hotel room, eyes averted, and a pair if safety scissors in his calloused palm.
"Cas?" Dean gives him a side long glance and shoots Sam a high browed look that Sam returns with a sheepish shrug.
"I request you help me perform the art of hair shearing." He says as tensely as he stands, grip tightening on the bright thing in his hand.
"Christ, Cas, you want a hair cut?" Dean chuckles and Castiel must resist the urge to condemn Dean on his blasphemy. Instead he nods almost shyly and thrusts out the scissors to Dean. "Why me?" He asks incredulously.
"I prefer your hair over Sam's." Castiel replies honestly "His seems problematic." Dean snorts at that and Sam rolls his eyes before grinning at Dean.
"Come on, Dean, you always cut my hair when I was a kid." Sam gives Castiel a meaningful look he cannot understand or interpret at all. "Stop bitchin' and do the dude a favor."
And that's how Cas finds himself sitting on the motel room toilet with Dean's fingers in his hair. Dean has nice fingers and Cas should know. He kind of remade them for his Charge. They're long, warm, and calloused as they comb carelessly through this locks. "I have the scissors…?"
"Put those away, dork, I've got my clippers." Castiel pockets them and looks at Dean, hoping he isn't pulling one of those intense looks he's seen himself give to himself in the mirror. Dean sighs and shakes his head, smiling in a way that leaves Cas wanting to see it more. "Trench coat off…" Dean orders and Cas pulls it off, suddenly feeling naked.
"Now…?" Cas begins to turn his head but suddenly his face is boxed by Dean's hands, still warm and soft and dry and pure Dean.
"Now you sit there and I make you look pretty." And for some childlike reason, Cas finds himself closing his eyes and holding his breath. Even if he trusts Dean with all his Soul and with all his faith in the Father, this is just a bit too much. The slight press of the clip to the skin just above his ear almost made him flinch, and the whir was left ringing in his ears for hours later. But Dean was humming something foreign and it calmed him down, and that lasted till at last the contraption was lifted from his skull and Dean was sighing to himself.
"Dean…?" Castiel ventured, and suddenly the hands were brushing at his face delicately, almost tenderly.
"Man, am I good." Dean breathes before pulling Cas up onto uneasy feet and in front of the mirror, where he can finally see what exactly Dean has done. It's short like his own, cropped and close to his skull and he loves it. And he's smiling like none other at his expression, because for once…it's not Jimmy's sullen face looking back at him. It's his own bright face…and Dean's right there to share it with him. "So, Uh…" Dean starts, own smile growing and Cas feels dizzy and drunk off it.
"It's fantastic, Dean…" He bows his head, air sliding and sweet across his freshly shorn nape. "Thank you." That hand finds his neck, tender and soft like a lover.
"It's nothing Cas." But it's everything to an Angel who gave it all up for the man with him now.