Archive of Our Own

Chapter Text

Dean liked the atmosphere on East Broadway. He could slide into any one of the five bars and find a willing dealer. Pocketing the coke, he spun on his heel and headed back for the exit of the joint. The throngs of bodies dancing to music from half-blown speakers and sweating alcohol from their pores was not the kind of environment he wanted to get high in.

Walking the busy street, he caught the city bus right as it pulled up to the curb and dropped a couple dollars in for fare before finding a seat in the back. In his usual apparel of ripped up jeans and worn out hoodie, no one ever seemed to bother him. That day was no different, and he tweaked nervously at his wire frame glasses as he watched the city pass by outside.

He had just enough time to get back to his studio apartment and snort a line before getting dressed for his ‘job interview’. Hopefully in the haze of an upper giving him a high, he could land the job.

Rent was due on Tuesday.

Dean had just spent his last two dollars on a bus ticket.

“Do you know what we do here, Mr. Winchester?”

Dean’s left hand twitched nervously and out of habit he wrapped his forefinger and thumb around his right wrist. The women sitting on the opposite side of the oak desk had auburn hair and a pretty smile. She looked to be in her mid-thirties and didn’t fit in with what his brain had supplied for ‘runs a prostitution ring’.

“Supply prostitutes for high-paying customers that like things kinky?” When her perfectly manicured eyebrow quirked up, he added quickly, “Miss McKenna.”

“We supply a specific type of escort to meet our clients’ needs. Our escorts are submissive in every aspect of their role and enjoy playing the part.” Her brown eyes danced up and down his body, sizing him up in seconds. “You don’t fit the aesthetic of what I usually hire for my submissives. To be quite honest, Mr. Winchester, you don’t seem like you’ve followed a direct order once in your life.”

“To be fair,” Dean shrugged, “you don’t fit the… aesthetic for running a company like this.”

She didn’t respond right away, and suddenly Dean worried that he had blown the whole thing… until a ruby red lip quirked up slightly and showed the smallest hint of a smirk.

“Not all of my clients are women,” Miss McKenna continued. “Will this be a problem?”

“I have no preference one way or the other. Male, female, doesn’t really matter when they pay the bills.”

She nodded. “Good. On Saturday one of my regular clients will be in town on business. He owes me a favor, so I’m sure he wouldn’t mind testing your will in a trial run. Talk to my receptionist on the way out and she will provide you with a dress code form, our safety and liability handbook, and a location for your first meeting. As I’m sure you’re aware — promptness is one of the aspects of our business that we pride ourselves on. As is appearance and hygiene. If I hear from my client that you failed in anyway on these points, your employment will not be continued.”

Dean left the lobby of the Marriott by the airport feeling more than a little unease in his stomach. His ass hurt and he simultaneously felt like crying and throwing up on the sidewalk, but he had survived Miss McKenna’s first client.

Walking slowly, he made his way across the hotel’s carport area and felt a little better when he spotted a familiar scratched up Jetta sitting in the parking lot. He opened the passenger side door and ducked his head down to see the driver — not quite ready to place his sore ass on the torn up seat.

“You got a smoke?” He asked over the sound of Metallica playing on the car’s radio. A small hand held out a package of Camel’s and a Bic lighter with Yoda on the side of it. “Thanks.”

Dean stood back up, pulling a cigarette from the package before tossing it back into the car. As he lit up, his eyes tracked along the six story hotel building and he tried to pinpoint which room his ass had been whipped in. After a couple of quick puffs, he finally figured it out and used the cigarette to point top left-hand corner. “That one.”

The radio was turned down by a few notches and a voice called out from in the car, “You talking to yourself again, dipshit?”

He finished the smoke and tossed it to the ground, quickly stomping out the flame with his shoe. Carefully, he climbed into the small car. Just as he had expected — his ass hurt like hell as soon as he sat. He fought back a grimace and turned to his best friend. “You’re lucky I love you, Charlene.”

“Nobody is lucky you love them, doofus.” She started the car and held out her hand — waiting until he had given back her precious Yoda lighter before shifting into reverse. “So… screwing for money now?”

“One hundred and thirty dollars an hour, my dear.”

Charlie nodded in approval and he watched her red hair bounce one side of her head — the other side had been shaven just a few days prior.

The Jetta headed towards his apartment in the Hollywood District. Halfway, stopped at a light on Fremont, Charlie looked over at him. “So Lisa decided to throw a bitch-fit again. My shit’s in the trunk — is it cool if I crash with you for a couple weeks?”

The up and down and sideways adventures that were ‘Charlie’s love life’ was a story that Dean knew well. They had been friends for almost three years, and Dean had long since adopted the spunky punk rock lesbian as his little sister. Despite the size of his apartment, he knew that it wasn’t the first time and wouldn’t be the last time that they shared a bed. “Just don’t hog the comforter this time, okay?”

“Sure thing, snugglepuss.” She grinned. “I stole Lisa’s pot stash. We can get high and you can tell me what that guy did to your ass for a hundred and thirty dollars.”

“Pretty sure I blacked out after the spanking.”

“Ohhh kinky shit. We might need popcorn.”

Dean missed seeing the world outside. It really shouldn’t have come as a surprise that ‘hell’ didn’t have windows, but that didn’t keep him from dreaming about blue skies and green grass.

“Food,” the voice called.

Dean looked up to the solid concrete door that sealed of their prison and watched the six inch by twelve inch slot on the bottom slide up. A tray of food was shoved inside the room, followed by two bottles of water.

He waited for the slot to close back, before moving across the room to sit down next to the tray. Sammy followed a couple moments later. His pace was slower thanks to the bruising running along his rib cage.

Examining the tray, Dean quickly set out to separate the sandwich into two equal servings, parted the stale chips into two identical piles, and set the apple aside to be savored last as a special snack.

Dean held out the half of a sandwich that looked slightly larger to Sam. “Eat up, Sammy.”

Sam shoved his messy brown hair behind his ears and took a tentative bite of the ham-on-plain-bread sandwich. “Dean,” he whispered.

The topic that was about to be brought up was one that Dean had already heard a dozen times. He quickly shook his head and took a bite of one of his chips. “No, Sam.”

“He told us how to end this.”

Dean shook his head. There was no way he was going to take their kidnapper for his word. “Sam, someone will come for us.”

“It’s been two months, Dean.”

“I’m not doing it, Sam.”

On Monday morning Dean stepped into the non-descript office space that held Miss McKenna’s prostitution… ahem, escort, company and nodded as the receptionist waved for him to go in. His new boss sat behind the solid desk and finished a phone call before looking up at Dean.

“Mr. Winchester… have a seat.”

After everything that had happened Saturday night, there was no way he was going to be intimidated by the woman before him. Not unless she pulled out a whip collection.

He sat down in the chair across from her and found the nerve to ask, “Was the client happy?”

“He was. He said you lacked the technique and skill of a well-polished sub, but you took direction well and did everything he asked. I’m curious — how was your experience?”

Dean remembered the way his ass had burned the next morning once the drugs wore off. There was no way he was divulging that information. “It was a job.”

“Very good.” She nodded approvingly before opening a draw and bringing a file out to lay on top of her desk. “On occasion, Mr. Winchester, I partner my clients with a sub on a permanent regular basis. It just so happens that I have a new client that would like the services of a submissive escort that lacks prior training — like yourself. The way this arrangement will work is that you agree on a set day each week that you meet with the same client. On top of that, I will also have various jobs that arise for you to do on your free days. Sound doable?”

“Yes, ma’am.”

Miss McKenna smiled and nodded her head. “Good. Our client has offered his own instructions for the sub and requested a specific wardrobe be worn at each meeting. You are not to bring drugs or alcohol of any kind onto his property. You will wear a three piece tailored suit, undershirt, and a pair of silk panties — the color of which does not matter.”

Dean immediately frowned. The suit he could manage but… “Panties? Is this some degradation bs?”

She pursed her lips and stared him down. “Do you think it’s degrading to be a woman, Mr. Winchester?”

“I, uh…” Dean quickly shook his head. “No, ma’am.”

“Do you have a problem wearing silk panties to meet your client?”

“No, ma’am,” he repeated as he ducked his head. “Of course not.”

“I should hope not. Stop at the receptionist’s desk on the way out. She has your paperwork on the new client and an advancement check to help cover the costs of your new attire. Anything else?” He shook his head once more and stood to leave. Miss McKenna’s voice stopped him before he could leave the office. “If you have any issues with this client, Mr. Winchester, please don’t hesitate to let me know.”

Outside of the office the receptionist handed him a thick manila envelope and a smaller envelope that held his check. As he stepped back out onto the busy street, his curiosity got the better of him and he opened the top of the client folder.

Clipped to the top piece of paper was a smiling photograph of the man that would be dominating his life — quite literally. He stared at the piercing blue gaze and wondered why a guy like that couldn’t just date normally without having to pay.

Maybe it was because he had a panty fetish…

Dean walked towards the nearby bus stop with the client’s name on repeat in his mind.

Castiel Novak… Castiel Novak… Casti…

He had no idea how to pronounce ‘Castiel’ and prayed that he didn’t make a fool of himself immediately.

Pulling his phone free from his pocket, he opened up a new text message to Charlie.

Take a shower.gotta buy new panties.

The response was almost immediate. Do I wanna know?