A/N: On Tumblr unforth-ninawaters is doing a #WritingPromptWednesday. It's fun and you should join! The theme was Music/Musician and here was the prompt I chose:

Time to throw some shade: not only is my make up better than yours, my dress sexier than yours, my waist better cinched, my hair bigger, and my tuck perfection, I've also got the tightest lip sync in this damn city and you are going DOWN AU

And now I want to start watching RuPaul (I haven't yet. I know shame!)

Disclaimer: All Kripke's

Sorry Not Sorry

"Charlie, what are we doing here?"

Charlie grabbed Dean's hand and dragged him through the bar's door. "When was the last time you got laid?"

"Can we not discuss this?"

She wandered up to the bar and ordered them two beers. "I worry about you Dean. And Sam would too if you told him anything. That damn "no chick-flick moments" rule is bullshit. You're brothers; you should talk with each other."

Dean grabbed his beer and chugged it down. "I don't really do touchy feely Charlie and you know it."

"I do know it and that's why I think you should at least go over and visit him."

He sighed. "What, so I can say I'm lonely now that you've moved out of our apartment so you can live with your girlfriend of five years? I'm not a dick. I could always get a dog…"

"I thought your apartment doesn't allow dogs."

"It doesn't."

Charlie sighed and scanned the bar. "Okay, let's just get you someone. Mopey Dean isn't my favorite Dean."

"If it makes you feel better it's not my favorite either, kid." Dean finished off his beer and looked around the bar. Ever since Dean had moved out with Sam to California he hadn't seemed to hold a single relationship. The closest he'd ever gotten to one was with Lisa back in Lawrence, but when he announced he was headed west they both agreed long distance wasn't going to work out. Everything had been okay, he could handle the no strings attached one night stands, but as he had gotten older times had changed. He hadn't known how much until Sam said he was leaving and now Dean's apartment felt even emptier.

So far, no one in the bar was catching his eye. Some looked too fake while others too young.

"What about him," asked Charlie, her finger pointing over to the pool table.

He wasn't bad: dark hair and eyes, and in fact was a bit similar to Dr. Sexy. Still…"I don't think so."

"Well, what about her?"

The woman certainly looked fine. Curvy, blonde, but…."No."

"How am I supposed to be your wing woman if you keep knocking down all my suggestions, Winchester?"

He shrugged his shoulders. "I guess I'm just not feeling it tonight."

Charlie finished off her beer and placed a few bills on the counter. "Why don't we go back to your apartment then and have a Harry Potter marathon."

"Sure, you know this isn't a breakup."

"I know, but you are seriously moping like you are. We have got to get you out of this funk."

Dean stepped out of the bar and into the warm night air. "I'll be fine. Just give me the rest of the week and by the end I'll be fully adjusted. It's only been two days since he moved. I will be fine."

"Okay, say what you want. I care about you Dean."

He smiled and picked her up, spinning her. "Yeah, I know."

"Dammit Dean, put me down!" Charlie hit him in the shoulder, but he just smiled. He sat her back down and she punched him in the shoulder. "Screw you, Winchester."

Dean laughed. "Never gonna happen, Bradbury."

She leaned against his shoulder as they walked. "Good. How would I explain that to Gilda?"

"I don't think there is a way that could ever be explained except a shit ton of tequila."

Charlie laughed and then squealed. "Look!" She pointed at a giant display in the front of a club. The poster was huge with a larger than life image of a woman with masses of curly black hair, stunning blue eyes surrounded by silver glitter, lush pale pink lips, and Dean's eyes trailed down to the low cut of her silver dress. He looked up to the left and read the information there:

Strut your stuff at Amateur Night!

10:00 pm November 1st

Featuring an appearance by Cassie Steel!

Charlie whistled. "Damn, if I wasn't a lesbian and attached to Gilda I'd tap that."

Dean frowned and then glanced again at the poster closely, this time noticing the thick layers of makeup, the drawn on eyebrows, and the careful way the dress's cut was laid. Drag queen. Dean snorted and turned away from it. "I can contour better than that."

Charlie's head whipped around to face him. "What did you just say Winchester?!"

Fuck. "I said I can contour better than that."

She placed her hands on her hips. "And how would you know that?"

Dean walked away from the poster and Charlie and closer to where the Impala was parked. "I used to do drag."

"YOU WHAT?!"

He unlocked the driver's side of the Impala. "I did drag for a while. Entered a couple of contests, did a few performances. It helped pay for a couple of Sammy's books."

"Dean Winchester. Lover of pie, American muscle cars, and plaid, is a former drag queen. And he didn't tell me. His best friend." Charlie sat down in the Impala and slammed the passenger door.

"Easy Charlie. Baby didn't do anything to you."

"That's a huge secret. Why didn't you tell me?"

He started the car and backed it out of the parking spot. "I stopped around the time I got the job at the restoration garage. I didn't need the extra money."

"But didn't you have fun?"

Dean eased Baby down the crowded streets and thought about it. Despite always on the hunt for the cheapest makeup that could make him look the part and often using whatever he had on hand it had been…fun. He tapped on the steering wheel and thought back on that. It had been fun, completely throwing off crowds and feeling the rush of adrenaline whenever he took the stage. "Yeah, it was."

"Then why didn't you keep doing it?"

"It still cost money to do it all and I didn't want to have to explain to the guys at the garage why I had eye liner on."

Charlie looked at Dean and grinned. "You're doing it."

"No, Charlie I'm not-"

"You said it yourself you think you're better than that other guy. Prove it. Go to the amateur night and kick ass! I'll go for moral support."

"Charlie-"

"Dean, just do this one thing and I promise I won't bother you about the whole Sam thing anymore."

"Do you swear?"

She drew a cross over her chest with her finger. "Cross my heart."

Dean stopped at the red light and looked over at Charlie. "Okay."

-o-O-o-

Now that the day had arrived Dean was having second thoughts. He had bought a new slew of makeup earlier in the week since he knew there was no way the makeup he used last time could be any good and when he got home it was going in the trash. Said makeup was arranged on the bathroom counter along with two intimidating items: shaving cream and a razor. If there was one saving grace Dean could count on was that he already kept a smooth chest. Picking up the shaving cream he sprayed on a thick layer down his legs from his ankle to almost up to his hip. He hopped into the shower and began the arduous process, making sure to go slow and close to avoid nicking himself. The longer it took the easier it was for him to relax and slip back into the mindset he had once before.

Once the shaving was completed he rinsed off the excess shaving cream and dragged the stool he brought in next to the sink; it was time for makeup. He picked up an Elmer's glue stick and pressed it over his eyebrows a few dozen times each, alternating by adding a bit of powder and foundation to make a clean slate. Grabbing a makeup sponge he drenched his face in liquid foundation, keeping it in check it was all going the same direction, before patting on powder over it. He pulled out brushes and other powders and creams to begin the transformative process of contouring and highlighting. Christ, it was taking him back. When it was just him and Sammy, hot dogs every other night and the others Ramen noodles. When he'd come home late at night, grease or glitter under his nails, and Sam had fallen asleep studying. He tapped the brushes to let excess powder out and picked up a pencil and filled in new eyebrows, medium width and a high arch. Selecting a smaller brush he filled in dramatic smoky eyeshadow, paring it with winged eye liner and thick mascara. He grabbed a nude lip liner and lined his lips before picking up a sexy shade of red lip color. With a few swipes and puckered lips he finished. He washed his hands of all the makeup and off his black painted nails. He snagged his wig cap and tucked his short hair inside it, securing it with a few bobby pins. He looked up in the mirror and blinked.

It was familiar and him, yet not in so many ways. His cheekbones accentuated giving the illusion of a higher structure and hollowed cheeks. Just all of it looked so…feminine and Dean smiled. He missed this more than he admitted. Now came a part he didn't miss: tucking. With a bit of adjusting and pausing he managed to get everything in place under his panties before he rolled on a pair of fishnets. The shorts came next, cutting off at his upper thigh and made of tight leather. He left them unbuttoned and pulled a corset off of the bathroom floor and wrapped it around his stomach. He sucked in and hooked it in the front. He breathed back out and felt his stomach fight against the fabric as he reached behind his back and grabbed the strings pulling tight. He managed to tie it off in the back and he let out the breath he had been holding. He grabbed a black bra and hooked it around in the front, swung it around forward and slipped his arms through the straps. He stuffed the inserts in each cup, moving them a bit until everything was settled comfortably and secured with fashion tape. He pulled a leather tank top off a hanger and slipped it on, zipping it up in the front. He buttoned his shorts and buckled a studded belt around his waist. Dean finished it off his look with studded cuffs on wrists and a pair of worn Doc Martens. He picked up the short, platinum blonde wig and placed it on his head. He took one last look in the mirror, brushing his bangs out and fixing the sides of his hair, before he left the bathroom.

"Charlie, I'm coming out now."

"It's about time you got your ass out here Winchester," she remarked. Dean took a deep breath and stepped into the living room. Charlie's mouth dropped and her eyebrows rose on her head. "Holy shit you're hot!" She stood up and ran over to him getting a closer look. "It's like Debbie Harry and Joan Jett had a daughter!"

Dean laughed. "Thanks."

"Seriously, this is fucking cool. Hey! What's your name?"

Dean rubbed the back of his neck. "Um…Em Paula."

Charlie gave him a look. "Did you really use a play on 'Impala' for your drag name?"

"So? Are you ready to go?"

Charlie smiled. "Yes! It's time for you to rule the night, Winchester. Be fierce."

He lightly punched her on the shoulder. "Just go get in the car, Bradbury."

-o-O-o-

Dean felt completely out of his element. Most of the drag queens around him where more flamboyant, and brightly colored than he was. He felt like he was standing out because he wasn't bright and instead someone had picked him up from the punk rock era. He lost Charlie when she found a group of drag kings to talk with and now he was stuck nervously waiting and regretting every decision he had made. "I don't think I've seen you around here. Here for amateur night?"

He turned around and was face to face with the drag queen from the poster. Tonight her dark hair was done up in large, dramatic curls, one rested on her forehead. Her blue eyes were framed with cat-eye eyeliner and silver glitter with a touch of blue eyeshadow. She was sporting plump, deep red lips and had a beauty mark high on her cheek. Dean's eyes followed down her neck to her plunging cleavage-Jesus how did he pull off that neckline?-where her shimmery silver dress clung to every curve from her breasts to her waist to her hips. The dress was long, but had a slit clear up to her hip on one side and her stiletto heels were killer high causing her to look down at Dean. "You're from the poster. Cassie Steel."

She laughed and her deep voice threw Dean for a loop, but he rolled with it. He didn't change his voice when he was in drag either, so he couldn't judge. "I am. Nice to see I have an admirer. Who are you?"

"Em Paula."

He smiled. "Cute. You don't look like an amateur."

"I don't do this often. Haven't really for a year, but at least my makeup still came out good."

Cassie Steel raised an eyebrow. "Is that so? And is that supposed to mean anything?"

Shit, but if Dean was already started… "Well, yeah. If you let me doll you up I could help soften your jawline and tweak a few other things too."

She smirked and looked down at him. "Of course sweetheart and I can help you with this." She picked up a piece of his hair. "Can't have you walking around wearing a bird's nest." She patted one of her luscious curls. "I'd be glad to help."

Oh fuck it was on. "Sure and if you every need help with a corset let me know. It can be pretty hard getting them tight enough by yourself, but then again not everyone can be gifted with the skills like me."

Cassie Steel crossed her arms. "And if you ever want a dress just call me up. It can be a little intimidating trying to pull off something like this," she gestured to herself, "but I understand not everyone can pull off something as sexy as this."

Dean stepped closer to her and got up into her face. "Yeah, well at least I know my tuck is so damn perfect I can wear these."

He saw the color rising in Cassie Steel's face. "Well I've got the tightest lip sync in this damn city, bitch, so why don't you back off."

"You wanna bet? I bet you're all just hot air."

She pointed her finger into his chest. "You wanna bet? Fine. You, me, lip sync off."

Dean smirked. "See you on the stage then."

Cassie Steel gave him a smug look. "I'm looking forward to it Em Paula." She sauntered off and damn was that a nice sight.

Once she left Dean let go of a breath he didn't know he was holding and suddenly the weight of what he just did settled on him. He was having a lip sync off with a queen who was fucking headlining tonight. He ran through the crowd looking for Charlie's ginger locks and found her talking with a leather clad drag king. She caught a glimpse of Dean and her eyes lit up. "Dean! Meet Meg. She's super cool."

He sat down next to Charlie and nodded to her companion. "Em Paula."

She smirked. "Demon."

"Nice." He turned towards Charlie and grabbed her beer.

"Hey, I was drinking that!"

"I am royally fucked."

"What did you do?"

Dean sighed and let his head rest on the table. "I accepted a challenge to a lip sync off."

"From who? Can you even do it?"

"Cassie Steel."

Meg raised an eyebrow. "Cassie? You really must have pissed her off."

Dean cringed. "I may have told her that her makeup, waist and tuck were…substandard."

Meg shook her head and finished off her scotch. "You don't know what you've started. Cassie hasn't lost so far since she started here."

"Fuck."

Charlie grabbed him by his shoulders. "Do not let her beat you, Winchester. You are fierce and going to kick some serious ass, got it?"

"Yeah," he drank more of Charlie's beer. "I'm gonna kick some ass."

"Can I have Em Paula come up on stage? Em Paula?"

Dean slid Charlie's beer back over to her. "Wish me luck."

"You've got this Winchester."

Dean strode up to the stage and followed the steps up to backstage. There, Cassie Steel was impatiently tapping her fingers against her arm. "This is how it's going to work. You pick your song. Kevin-," she pointed her thumb at the young college student manning the sound booth, "will play it. Any questions?"

Dean crossed his arms. "Yeah, who goes first?"

She smirked. "I am so everyone knows what good lip sync looks like. And I expect you to be front and center in the audience."

"Bitch," he muttered under his breath as he walked back to the front and to the seats. He sat down in one with a huff and the lights on stage turned on.

"Ladies and gentlemen we a have a treat for you tonight! Cassie Steel has challenged Em Paula to a lip sync off!"

There were cheers and hollers from the crowd.

"Now, without further ado, Cassie Steel!"

The music started, soft and slow, and Dean was transported back to his childhood, oh fuck. Cassie Steel slinked out from behind the curtain as the lyrics started.

You had plenty of money, 1922.

You let other women make a fool of you.

Why don't you do right, like some other men do?

Cassie sauntered out to the middle under the light, hand on her hip.

Get out of here,

Get me some money too.

She kept walking to the left and walked down the short steps and into the crowd. She sat down in a man's lap and took off his hat.

You're sittin' down wondering what it's all about.

If you ain't got no money they will, put you out.

She pushed out of his lap and slinked through the crowd before finding Charlie and leaning into her; her breasts up in Charlie's face.

Why don't you do right, like some other men do?

Charlie grinned and grabbed Cassie to pull her closer, but she just smiled and pushed away, wagging her finger back and forth in front of her.

Get out of here,

Get me some money too.

She strutted down the middle of the rows and Dean had to admit she was amazing at performing and lip syncing.

Now if you had prepared 20 years ago,

You wouldn't be a wandering now from door to door.

Why don't you do right, like some other men do?

Dean's neck was craned trying to keep an eye on her and he didn't even notice she was next to him until she grabbed his face. She trailed her fingers across his jaw and she looked smug.

Get out of here,

get me some money too.

She let go, walking away, giving Dean a full view of her ass.

Get out of here,

get me some money too.

She turned back around to strut towards Dean. She stopped right in front of him and sat down in his lap her arms wrapping around his neck. Her face close to his.

Why don't you do right, like some other men

She leaned in, their lips almost touching, until she pushed herself up and away from him.

do?

She walked back up to the stage and slinked back behind the curtain as the crowd cheered and wolf-whistled, the last smoky notes echoing.

Dean was breathing hard. Holy shit was she good. He hurried back stage and found Cassie Steel next to Kevin at sound. She grinned. "Good luck out there." She walked off leaving Dean blinking.

He shook himself out of it and skimmed through the lists of songs quickly finding the one he wanted. He told Kevin and stood back stage.

And that was our lovely Cassie Steel! Can her competitor match up? Put your hands together for Em Paula!

The music started fast and loud and Dean grinned, running out on to the stage. "Are you ready to rock?"

The crowd cheered and clapped and Dean smirked as the lyrics started up.

I don't give a damn 'bout my reputation

He mimicked playing air guitar along with the rift.

You're living in the past, it's a new generation

He strode over to another part of the stage.

A girl can do what she wants to do and that's what I'm gonna do.

An' I don't give a damn 'bout my bad reputation

Oh no,

He played the rift on his air guitar up against the curtain.

Not me

An' I don't give a damn 'bout my reputation

He jumped off the stage and landed in a crouch.

Never said I wanted to improve my station

He lifted his leg up on a table and used it as a guitar.

An' I'm only doin' good when I'm havin' fun

An' I don't have to please no one

An' I don't give a damn 'bout my bad reputation
Oh no,

He looked out in the crowd in search of Cassie Steal as he walked through the tables and chairs.

Not me, oh no, not me

Bingo. She was sitting on Dean's left her face expressionless.

I don't give a damn 'bout my reputation

Instead of playing the rift, Dean flipped Cassie off, getting a lot of rumbled 'oh's' from the crowd. .

I've never been afraid of any deviation

Dean grabbed his breasts and pushed them, making the crowd laugh.

An' I don't really care if you think I'm strange

I ain't gonna change

An' I'm never gonna care 'bout my bad reputation

Dean ran through the crowd, pulling people up and getting them to stand and dance.

Oh no, not me, oh no, not me
Pedal, boys!

He ran back up to the center of the floor and landed on his knees, dramatically performing the short guitar solo.

An' I don't give a damn 'bout my reputation

He grabbed someone's drink and gulped it down.

The world's in trouble, there's no communication

He wiped off the liquid that was still on his face, smearing some of his makeup.

An' everyone can say what they wanna to say
It never gets better, anyway
So why should I care about a bad reputation anyway?
Oh no, not me, oh no, not me

He continued to rock the air guitar and everyone in the crowd was on their feet as he made his way back up on the stage.

I don't give a damn 'bout my bad reputation

He looked back out in the crowd for Cassie Steel, having one last surprise planned. She had moved to the front now and had a frown on her face. Perfect.

You're living in the past, it's a new generation

He started to run off the stage.

An' I only feel good when I got no pain
An' that's how I'm gonna stay

He jumped the steps and ran towards Cassie Steel.

An' I don't give a damn 'bout my bad reputation

She looked confused, but he just grinned and pulled her up.

Oh no, not me, oh no, not me

Not me, not me

He leaned forward and kissed her, makeup and sweat smearing across their faces. But Jesus was she a good kisser. He leaned closer and brought his hands up to the edge of her wig and he pulled at the real hair under the wig cap. Cassie Steel groaned and Dean took advantage of it by letting his tongue duck inside before she pushed him away. Her eyes were wide, but a smile tugged at her lips. "You're good Em Paula."

Dean smiled and pushed his bangs away from his face. "Thanks, you weren't so bad yourself. Jessica Rabbit was my first crush."

She grinned. "Well, I can't help it. I was drawn this way."

Dean laughed and rubbed the back of his neck.

"Let's give a hand for Em Paula."

The crowd clapped and cheered.

"Now it's your time to vote. Whoever votes for Cassie Steel, give her a hand."

The crowd was loud and chaotic.

"And what about Em Paula?"

The audience became raucous and there was foot stomping and whistling.

"I think we have a winner….Em Paula!"

Dean beamed and glanced over at Cassie Steel. "Honestly, you did well."

"Thanks you did too." She placed her hand on her neck. "You know…"

"Dean that was fucking fabulous," gushed Charlie.

Cassie cocked her head to the side. "Dean?"

He groaned and punched the red head in the side. "That would be me. I'm Dean Winchester."

Cassie smiled. "Castiel Novak."

Dean blinked before laughing. "Castiel. Cassie Steel. You punned your own name!"

He smiled. "My brother thought it was funny."

Charlie looked between the two and smiled. "I'm gonna call Gilda. She might have a friend I can set Meg up with. See ya later bitches."

She left and Cassie, well Dean guessed he could say Castiel now, cleared his throat. "I wanna sort of apologize for earlier. I can get pretty bitchy when I'm in drag. You probably wouldn't even recognize me if you met me in the streets."

Dean raised an eyebrow. "You wanna bet?"

He smiled. "Sure. I'll be waiting outside of here tomorrow night at seven."

"I'll see you then."

-o-O-o-

Dean parked the Impala outside of the club and waited. It was ten minutes to seven and he was getting nervous. For some reason he was more anxious about meeting Castiel when he was out of drag than when he was in drag. A dark haired man in a trench coat was walking down the sidewalk and Dean decided he should just get out and wait for the other man. He shut the door to the Impala as the trench coat man looked around and leaned awkwardly in the doorway of the club. No way, this was Castiel?

As Dean got closer he took in the man's untamed hair, blue eyes, stubble on his chin, and strong jaw. He was wearing a suit with the tie on backwards and the trench coat over it. He cleared his throat and the man turned his head. "Castiel?"

He openly wandered his eyes over Dean's body. "Dean?"

He smirked. "Yep. You clean up pretty well."

He nodded. "You too."

Dean held up his hands to show his nails still had traces of nail polish. "Mostly." There was an awkward silence as the two didn't know what to say. "You wanna go get something to eat?"

"Sure."

Dean nodded over to his car and Castiel stared at it. "What?"

"It's an Impala."

Dean got in the driver's seat. "Yes…"

"Em Paula?"

He sighed and turned on the car. "You and Charlie both."

Castiel smiled. "I think it's clever."

"Thanks." He pulled out of the parking lot and away from the club where Cassie Steel and Em Paula met as he went on a, hopefully, date, with Castiel.

A/N: Songs "Bad Reputation" Joan Jett and the Blackhearts & "Why Don't you Do Right" by Peggy Lee, but performed by Jessica Rabbit.