This story is based on TEDTalk!Sam from episode 14.13

"No way!" You close your eyes. This has to be a nightmare.

"You're the only person who made it to the hotel. We're all snowed in until morning, no one can get a flight out. You're going to have to staff him until I get there. His schedule is pretty light compared to what it usually looks like. Half his meetings were canceled because of the storm." Pepper rattles into the phone. She's only a year or two older than you but she's your boss's boss. She's Sam's executive assistant, in charge of the entire assistant staff and she's had it out for you since you started four months ago.

"I don't think I can do this." You gulp, shrugging your jacket off. You deliver mail and push the coffee cart around the building, the lowest rung on the corporate ladder.

"You don't have a choice." She snips. "You think this is what I want? I'm going to end up paying for this, even though it's not even remotely my fault. I can't control the weather…look I'm going to send you his schedule. Just make sure he's on time. He'll let you know if you're doing something wrong, believe me. Just keep your mouth shut and do what he tells you to do. Whatever you do, don't cry. He hates it when people cry."

"Why would I cry?" You regret answering the phone and you already know the answer to your question.

Sam Winchester is a real son-of-a-bitch and everyone knows it.

To say his reputation proceeds him would be a gross understatement. He's smart, successful, ruthless and above all, focused. You've worked for Winchester and Singer for six months and have yet to encounter him.

You've never even directly spoken to him, never seen him in person other than the monthly reviews he conducts with the entire company in attendance. Even then he's just a man on a stage.

"I'm emailing you right now. Keep a copy of the schedule on you at all times." She pauses to take a breath. "Are you listening to me?"

"Yeah, I'm listening. Have the schedule on hand, keep my mouth shut, and try not to burst into tears."

"Just don't fuck this up." Pepper is as over-worked as everyone on the executive level. You can't really blame her. This job is her life. "You need to check in with him tonight. Just knock on his door and ask if he needs anything. He'll send you away, but he expects a check in just to be sure."

"Okay." You nod to yourself in a windowless hotel room. "I can do this."

The elevator rises slowly to the penthouse floor of the Ambassador Hotel. It's nearly midnight and his flight arrived only an hour ago. He was in Tokyo last week and was rerouted during the storms in Boston.

You knock twice on his door, waiting with bated breath and hoping he won't answer. You're about to leave when the deadbolt turns and the door opens to reveal Sam Winchester with a cell phone up to his ear. He pauses for a moment, looking you over head to toe before opening the door the rest of the way and walking away chattering to whoever is on the other line.

You stand in the hallway, unsure if the open door is an invitation. On cue he turns around, eyes narrowing as his nods his head.

Already off to a rough start.

Shutting the door behind you, you follow him into the living room, standing awkwardly, waiting for his call to end. When he finally hangs up, he presses his phone against his chest, staring at you like a zoo animal. "Pepper said you're the only employee here?"

"Y-yes." You choke out. "I was visiting family in New Mexico, so I flew in from-"

"We'll have to make due I guess." He cuts you off. "You have tomorrow's schedule?"

"Ahuh." You hold up your phone, forcing a smile.

"Ahuh?" He tilts his head. "I prefer actual words. Yes or no."

Your cheeks flush hot, embarrassment settling in.

"Yes, Mr. Winchester." You correct. "I have your schedule. Pepper asked me to check in and see if you need anything tonight."

"No. I don't need anything." His stare is unrelenting. "Do you have something more appropriate to wear tomorrow?"

His question takes you off guard as you look down at the sweatshirt and jeans you're currently wearing. "I, um, yes sir."

There's a nauseating combination of shame and anger settling into your gut. He really does live up to his reputation.

"Good. You better go. We have an early start tomorrow. I won't need you until after the gym. I'll be done by 6:15 and I expect you to be here."

"Yes, sir." You nod, looking at anything but his face. You're an ant under a microscope, already feeling the heat.

"Good. You can go now." He pulls out his phone, hits a number and begins speaking to someone in Japanese as you high tail it out of the room.

You don't cry until you're in the elevator. The doors shut as you fight back the urge to turn into a sobbing mess, instead of wiping away a few tears and composing yourself.

Three hours of sleep is all you manage. Between your nerves and being afraid you'll sleep through the alarm, you're up and showered at four and dressed by five.

Clutching a portfolio in your arms you step off the elevator. There's a full-length mirror at the end of the hallway and you stop to make sure you're presentable. You thought you'd be manning a promotional table during the conference, planned on wearing khakis and a pullover. You brought exactly one business professional outfit that you haven't tried on in a year or two. It's a plum-colored sleeveless sheath dress that's tighter than you would prefer. It looks good but perhaps a little much for this trial by fire.

"This is as good as it gets." You whisper, giving yourself a final look before finding Sam's room.

You knock and he answers immediately, holding his glasses in hand.

"You're late." He quips, turning around to gather his suit jacket and briefcase.

"I," You stop, checking your phone. "It's 6:15."

"In my world on time is late and early is expected."

"I'm sorry." You're horrified. "I didn't - I'm sorry."

"I don't want an apology. I want you to do better next time." He eyes settle on your bare shoulders, then tick down to rest of your body. It's a quick glance but you catch him. "I have files in the living room. Please make sure everything is in order and ready to go. Pack it all up, we don't want to leave anything to chance."

You wordlessly scamper around the room, carefully collecting half used notepads and countless pages of legal discourse that you couldn't understand if your life depended on it. When you turn back around, clutching his files in your arms, he's leaning against the doorframe between the entryway way and the living area, watching you intently.

Your cheeks burn hot. Sam is handsome, there's no arguing that fact, but he's also notoriously difficult to work for. You've never once heard even a whisper that he mixes business with pleasure. If anything he's known for being controlled. Everyone's heard of his type, high-level business execs that are uptight beyond belief.

But the way he's looking at you…no. It's in your head.

"I've got everything." You nod, shoving the files into your leather bag.

"Good, I want to get down there early." He checks his watch and strides out of the room without another word and you're left scrambling after him. Instead of heading to the public elevator you took earlier, he turns in the opposite direction to head toward the private lift his penthouse room offers as a perk. You stand beside him as the doors close and he pushes the button for the ground level.

He turns toward you, looking concerned. "I asked you to wear something business professional."

"I-" The humiliation continues. "I am. This is all I brought with me."

"I see." His eyes narrow.

"Would you like me to go grab a sweater to wear over it?" You ask softly.

"No." He purses his lips, head tilting ever so slightly. "I wouldn't be able to tell how tight your dress is if I couldn't see your panty line."

You nearly choke on your own spit. Letting out a nervous cough as your breath speeds up. You force yourself to look at him, trying your damnedest to determine what this is. Is he coming on to you? Just a perfectionist who's so caught up in the details that the outline of your lace underwear crosses some sort of invisible line?

"I didn't realize you could see. I'm sorry." You stare at the floor, praying to God this day ends quickly.

"Don't be sorry." He commands tone calm and even. "Take them off."

The world stops. All the oxygen evaporates out of the room.

Your eyes go wide, shooting up to meet him and his expression is unreadable. In a split second, your body reacts against your will, heat blooming between your legs, shame tightening in your chest.

You wonder if he's like a predator able to smell fear. Does he somehow know what kind of effect this will have on you? Is it the way you called him sir, or how quickly you responded to his commands?

"You want me to…" You can't finish the sentence but he doesn't need you to.

"Take them off." He repeats.

"Right now…here?" You whisper.

"Yes." He confirms, reaching out to take the bag from you.

You hesitate, but only for a second before reaching under your dress and hooking both hands in your panties. The elevator is nearly at the first floor, and sweat breaks out over your entire body at the idea of being caught.

Stepping out of your panties you hold them up, looking at him like a deer in the headlights. There's nowhere to put them, you didn't bring a purse, the conference is in the hotel so you left it the room. But Sam casually plucks them from your hand and stuffs them into the pocket of his suit pants as the elevator reaches the lobby and the doors slide open with a ding.

"Try to keep up." He hands you back his briefcase, your messenger bag of files, and steps out into the general population as you follow.