Having a little sister is hard, but it does come with some unexpected perks.
Dean was just washing up in the shower after a vigorous session with some blonde beauty he’d met at a bar. How he managed to reel her in besides his dashing good looks and irresistible charm, you ask?
His expert braiding technique - which he had time to perfect while raising his two younger siblings.
Dean stood up to get the attention of the bartender, who had his back turned in attendance to someone else’s drink when his eye was caught by a woman’s hot-pink mini dress and obviously bleached blonde hair. She was damn near having a fit when Dean slid up and stole the unattended bar stool next to her, flashing her a toothy smile.
“You alright?” The woman ignored his presence at first, but then finally turned to him with a huff. “Can you help me? My hair has a knot.”
Dean held back a laugh, was this chick serious?
“Uh,” he gaped, and the blonde simply rolled her eyes, “Forget it.”
As she went to stand, Dean quickly followed suit, “No, no, I can help with that. My sister gets her scrunchie caught in her hair all the time.”
Instantly, her eyes softened, “You have a sister?” The older Winchester nodded, “Yeah, my little sister, actually. I’ve picked up a few tricks over the years, but don’t tell anyone that.”
Dean winked, and the woman further relaxed, easing back onto the stool and crossing her legs. “That’s so sweet. Most guys don’t even know how to use a hair tie.”
"When my little sister was a kid she was too short tempered to do her own hair, so being the best big brother in the world, I learned how to do a wicked braid.”
Dean leaned forward and began untangling the woman’s curls, his musk enticing her instantly. “Now, let me help with that.”
Dean’s eyes snapped open at the sound of a frightened yelp and he tripped getting out of the shower, pulling the curtain off the rack with him.
“No, no, you don’t - ” A glass shattered in the other room and Dean clumsily wrapped a towel around his waist before swinging the door open with a yell.
“Hey! Everybody just calm down!”
Sam was taking cover behind the grimy motel sofa while Dean’s hook up, Uma, held a lamp high above her head. “This creep just walked in here, Dean!”
Just as Sam was about to explain himself, you interrupted with a snide comment that went unrecognised. “This is my brother, Sam. We’re sharing this room together.”
Uma looked appalled instantly, placing the lamp back on the bedside table and scrambling off the bed to apologise. “I am so, so sorry. I thought you were, like, breaking in.”
You folded your arms over your chest with a huff, “Dean, we’ve got work in Kansas.”
Uma stood in her shirt and underwear, still as a statue, while you, Sam and Dean gathered your less incriminating belongings together and packing them into the impala. Slowly, the woman began to do the same, although rather shamefully.
You almost felt sorry for her, but she wasn’t the first nor the last you’d give the cold shoulder. You knew better than to get attached to any woman Dean slept with, it was just natural for you to be standoffish.
“What about our case here? I mean we still gotta put an end to Archie Crane, don’t we?” Dean asked, pulling the back door open for you. “Y/N and I took care of that while you were supposed to be following a lead at Bourbon’s Place.” Sam shot Dean that snotty look he hated so much before ducking into the passenger seat.
“Salted and burned the body, he’s gone.” You quickly elaborated, for your poor brother’s peace of mind.
Uma lingered at the motel doorway, watching with sad eyes as she’d already come to understand Dean was skipping town. She wasn’t usually the type of girl to sleep with strangers, but something about this man disarmed her in ways she couldn’t explain.
Through all the poetic sentiments running through her mind as she watched the impala tear out of the car park and onto the dirt road, Uma did notice how neat your braid looked.













