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There was a lot that Sam didn’t know about Dean Smith. In fact, the only things he really did know for sure were that he had an affinity for suits that cost ten times as much as anything Sam had ever spent on clothing, he was perpetually on some kind of cleanse for reasons that eluded Sam, and that he drove a tiny Prius to work every morning that made Sam’s legs cramp just looking at it. He was also one of the most attractive people that Sam had ever seen, but that was neither here or there.
So when he thought about it, the fact that he knew so little about Dean meant that any new information he discovered shouldn’t come as a shock to him because it’s not like he had very many notions about the man that could be disproved, right? Or something like that, anyway.
Still, Sam couldn’t help but be surprised when he opened Dean’s office door to deliver some reports to him only to find Dean sitting at his desk (which was littered with various scraps of colorful fabric) with a couple of pins in his mouth while he focused on stitching what looked like an elaborate dress with great intensity.
Dean looked at Sam in shock with his jaw hanging open while the pins fell to the table, and it would have been humorous had Sam not been too occupied with staring at Dean with an equal amount of surprise. After a few seconds of awkward silence, Sam decided that he had one of two options: he could drop the reports on Dean’s desk and walk out of the room without acknowledging what he’d seen, or he could ask Dean why he was playing fashion designer of all things in the middle of a work day.
He knew which one he should do...but fuck it, he was actually really curious about the whole thing. Sue him.
“Are you...making a dress right now?”
Dean bit his lip and looked like he was scrambling for an excuse. “It’s part of a new campaign I’m working on,” he said finally. “I’m marketing dresses. To people. People who...wear dresses.”
Sam mentally added “terrible liar” to the List of Things Known About Dean Smith.
“Wow, that sounds pretty important,” Sam said, playing along. “People sure do need dresses. But why are you the one making them? Shouldn’t you be marketing other people’s dresses?”
“Well, if you want something done right, you’ve gotta do it yourself,” Dean replied and laughed nervously. “...are you buying any of this? Like, at all?”
Sam grinned widely. “Not even a little.”
Dean groaned and covered his face with his hands. “Is there any chance that you’ll just leave and never speak of this again?”
“I think we both know the answer to that.” Sam took the liberty of carefully removing a long piece of blue fabric from one of the chairs in front of Dean’s desk and plopping down in it. “So is this just a hobby of yours or...?”
Dean sighed and seemed to accept that Sam wasn’t leaving without satisfying his curiosity. “Look...I got really into Project Runway a few years ago when I was in college...”
“Wow.”
“...so sometimes I like to design clothes. I actually thought about going into fashion, but I figured that marketing might be a safer bet. I pretty much just do it now to relieve stress; it’s surprisingly relaxing...”
“Wow.”
“...except this job is always stressful, so now I spend an insane amount of money on fabric each month and have an entire room in my apartment filled with dresses. It looks like the hoarder’s nest of a seamstress. Or maybe the room of a serial killer who takes their victims’ clothing as trophies. I’m not sure what happened to my life.”
“Oh my God.”
When Dean finally finished his diatribe, his face was still in his hands and he peeked through his fingers to look at Sam to gauge his reaction. “I don’t think I’ve ever told that to anyone before. If you’re gonna make fun of me, you might as well do it now.”
“What? I think it’s kind of cool,” Sam exclaimed.
“Seriously?,” Dean asked skeptically.
“Yeah. I mean, I don’t know much about fashion, but I think this one looks pretty good,” he said while running his fingers over the soft, teal fabric of the mostly-finished dress lying on the desk. It really was lovely, and Sam marveled at the amount of work that must have gone into it.
Dean flushed under the praise and smiled proudly. “Thank you. High-low dresses are ‘in’ this year, so I’m really just following the trends.”
“...I’m not entirely sure what all of that means, but if you ever need help with any of this, then let me know. I’m not sure if I could actually be any help, but this looks a lot more fun than what I sit around doing at work.”
“Now that you mention it,” Dean pondered aloud while looking at Sam heatedly, “maybe I could use some assistance. After all, I’ve never had anyone to model my work before. It would be nice to see them on an actual person.”
“M-me? You want me to wear your dresses?,” Sam sputtered. “Wouldn’t they look weird on me?”
“Oh, I don’t know,” Dean said coyly, “I think you’d look fetching. Most of them would probably be a little tight across the shoulders and chest, but I could always make alterations, and you definitely have the legs for them. Plus, I’m pretty sure I have some bias-cut dresses lying around that would accentuate your narrow waist nicely.”
Sam couldn’t deny that the idea of letting Dean dress him up was doing things to him, and he fidgeted in his seat. “You really want me to model for you?”
“Well, I’ve definitely always wanted to get you out of that drab, yellow polo shirt,” Dean admitted while shamelessly checking Sam out. “So what do you say, Mr. Wesson? Perhaps you could come over to my place sometime, and we’ll see how pretty my dresses look on you...and then maybe later, we can see how they look on my bedroom floor. Only if that’s agreeable to you, of course.”
Sam’s brain short circuited and took longer than he would have liked to reply. “I find that to be more than agreeable, Mr. Smith,” he finally said.
There was a lot that Sam didn’t know about Dean Smith...but he definitely liked what he was finding out so far.