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Cheesecakes And Whiskey

Chapter Text




June 2008

Castiel woke up slowly, keeping his eyes shut at first, taking the time to appreciate the moment. He was sleeping on his back, his body all intertwined in his sheets, just warm enough so he wasn’t neither cold nor hot. He felt like he was lying on a giant cloud, soft and warm. Birds were chirping at his window, and Castiel could feel the first rays of sunlight on his soft skin. He finally, lazily, opened his eyes and turned his head toward his alarm clock.

6:48, he thought. Better get up now.

He pushed the sheets away, shivering slightly as he exposed his body to the chill air of the bedroom. He put on pyjama pants over his Batman briefs, stretched and yawned, and pushed the button of his clock to OFF before it rang, waking the entire neighbourhood. He didn’t put on a shirt, being comfortable with less clothes on in the morning. Castiel walked out of his bedroom and down the stairs, and made a beeline for the coffee pot standing on the kitchen counter. After pressing a couple of buttons and putting water in the coffee machine, he turned and opened the fridge to pour himself a glass of orange juice. Waiting for his morning fuel to be ready, he went back upstairs to fetch his phone : as expected, he had three unread texts.

From : Charlie

You up ?

It’s almost 7AM and I'm at your front door with muffins and bagels

... I bailed again :(

Of course. Castiel rushed down the stairs, made a sharp turn to the right and walked to the front door. He could already see a small body shape through the frosted glass, sitting on the porch. He unlocked the door, and as soon as it swung open, Charlie got on her feet and turned to look at Castiel with her best puppy eyes.

"Good morning", she said.

"Good morning", he answered with a smile. He looked behind her. "How the hell did you get here?"

"Took the bus. She only lives a few blocks from here. I was too drunk to drive last night so my car slept in a creepy parking lot."

"So it got serious again last night?"

"Please don’t judge me, Cas..."

"Come on, you know I won’t. You brought breakfast" he said, smiling even more and stepping aside to let her in. Castiel noticed she was still wearing the clothes she had yesterday. "You didn’t stop at your apartment before coming here?"

"I woke up at 6:15 and I didn’t want to miss breakfast", she said, walking toward the kitchen.

Castiel followed her. It was a tradition between them to have breakfast together when they worked the same shift at the restaurant. Today would be no exception, even if Charlie had had a late one last night.

"Ok, stop killing me with the tension. What happened?" Castiel replied, taking a bagel from Charlie’s bag and pulling his cream cheese out of the fridge.

Charlie let out a weird sound, something between a growl and a whine. Castiel started eating his bagel, pouring each of them a cup of coffee.

"I don’t know! I suck so bad at this", she started, talking fast. "We went to a bar and we really had fun, honestly. We hijacked the karaoke machine and sang until our throats were soar. And then we went to her apartment and I had the best sex in my entire life and I was so drunk and so tired after that I just fell asleep by her side. When I woke up she was glued to my side and when I tried to get out of bed, she hugged me tight and told me she loved me –"

"And that’s when you put your pants back on as fast as lightning and ran out the door."

"Yep" Charlie answered, lowering her head and taking a bite of her muffin. "Why do they always do that? Why do I always find girls who want serious relationships?"

"I don’t know, dear. You must look like someone who wants something more than just sex. Or you make them believe you want more than that."

"I should wear a sign around my neck."

"That is actually a great idea. Just get a tattoo on your forehead : No Love, Just Sex in big bold letters" Castiel grinned, finishing his bagel.

"Shut up, dude. It's not worth it. They won’t read it anyway. I don’t think the girl from yesterday even knew how to read."

They both laughed and started talking about all Charlie’s 'Best Relationship Fails', a thing they’ve been doing for a while now. They talked until 8:30 before Castiel excused himself to go take a shower and get ready for work. When he came down again, all dressed up and ready to go, Charlie was sitting on his couch, feet on the coffee table, reading one of her comic books.

"Ready to go?" Castiel asked, looking at his watch. "We only have 30 minutes left before our shift so let's just stop by your place and gather your things. I'll drive you to that creepy parking lot tonight after work."

"Such a good friend you are, dropping off a girl like me in a parking lot at night."

"First of all, it won't even be dark yet. Second of all, I dare anyone who tries to kidnap you to get it done without losing half of his or her teeth."

"You're right. I'm a badass."

Castiel rolled his eyes, a smile on his face. "Come on. Put your shoes on, Black Widow,  we're gonna be late."


Dean opened a sticky eye with a groan, the sun hitting straight in his face. His mouth felt like he swallowed a whole bucket of goo and he could still taste the whiskey on his tongue. Dean turned his head to the other side, as far away as he could from the sun, rubbing his eyes. A pain shot through his head. He really shouldn't have drunk that much last night. He lifted his head a bit, gently, to look at his clock.

9:16. Good. He could still sleep a bit.

Wait. What ?

He lifted his head fast again, sending a vivid throb in his head.

"Shit!" he said, ignoring his aching body. "Shitshitshitshit!"

He grabbed the first pair of pants he could reach, snatched his job uniform from the hanger in his closet and ran to the bathroom. His shift started at 9:30 and he could not afford to be late again. He put his toothbrush in his mouth and started putting on his pants and walking back to his room. He had one leg in and tried to put the second one in his jeans, but he stepped on the fabric and got his two feet caught up. He jumped awkwardly, trying to free either his pants or his foot, but his attempt failed miserably and he fell on the floor, knees hitting the ground hard.

"Son of a bitch!" he cried angrily.

He rolled on his back and pulled up his pants before getting up again. While brushing his teeth, he put on a random t-shirt and two different socks, not caring a second about how stupid he looked. He went back to the bathroom, rinsed his mouth, grabbed his shoes in a hurry and ran to his car without locking his apartment door.

"Sorry Baby, no time to warm you up this morning" he said, starting the engine of his Impala.

He got out of his parking space with a screech, and burned almost every stop sign he encountered on his way to The Galleria.

Dean arrived almost on time, but wasn't late enough to be noticed. He changed in the back store's bathroom and went up front to start his shift.  The only one who gave him an exasperated look was Benny, but Dean was used to his friend's attitude.

"Got a rough one last night, brother?" Benny said, a smile in his eyes.

"What can I say? Chicks dig me", Dean smirked. "One of them kept buying me drinks. You know me, I can't say no to free booze."

"Did you bring her home with you?" Benny asked behind the counter.

"Nah, didn't feel like it. But I have her number. I'll call her in a couple of days, let her steam a bit."

"You are unbelievable."

"Usually, I get that compliment in bed, but I'll take it whenever it comes, thank you", Dean replied with a smile. "Wanna come eat with me later?"

"Thanks, but I brought my lunch. As usual."

"I don't get how you can eat the same damned pork sandwich every day of the week."

"And I don't get how you can eat at the same damned Cheesecake Factory every day of the week", Benny immediately replied.

"At least I can try something different at every meal."

"And we both know you don't."

Dean laughed. He enjoyed a lot having the same shifts as Benny. They've known each other for a long time before work, and they were still seeing each other outside of work, and Benny was one of the few people Dean couldn't get tired of.

"You know, if you'd only give it a try, you'd see why", Dean answered before turning to his first customer. "Hi, welcome to MicroCell. What can I do for you today ?"


It was 6:04PM when Castiel finally went to his locker and untied his apron. Charlie was just beside him, waiting for him to be ready.

"You are so slow, Cas, it's impossible" she said.

"And you are always in a hurry" he answered back.

"Of course I am, I haven't had a shower in 48 hours and I didn't even brush my teeth this morning."

"Ok, I'll give you that one" Castiel replied, taking off his tie. "Let's go."

They got out of the restaurant and stepped into the mall. Castiel liked working in a restaurant inside a shopping center. There were always new customers and he could go shopping on his break. But parking was a real pain in the ass. He only found a place on the other side of the mall this morning, so they had to walk all the way through.

"Geez, you parked, like, in Mordor, today" Charlie said.

"Hey, it's entirely your fault. It's not my problem if you couldn't find your tie. We didn't have time to find a better place."

They reached Castiel's white Ford Focus. As soon as they got in, he plugged his phone in, connecting the bluetooth.

"What would you like to sing?" Castiel asked, his finger tapping to find his playlist.

"How about our all time favourite?"

"Okay, here we go" Castiel laughed.

They drove to the bar Charlie went to, the music at an ear-splitting volume, screaming more than singing the lyrics of I Want You Back by Jackson 5. They've sung it so many times, they worked out a way to do it as a duet. No matter how many times Castiel did this with Charlie, he always ended up with a huge smile.

After dropping Charlie off at her car and making sure she was safe, Castiel went home, glad the day was over. He couldn't wait to trade the crisp white shirt for a normal t-shirt (or no t-shirt at all).

He parked his car in the driveway and went inside to prepare himself dinner. He took a few minutes to cook some pasta to go with the piece of chicken breast he didn't eat last night and made a ceasar salad to complete his meal. He took a beer out of his fridge and dragged himself to the living room. Castiel sat on the couch and turned on the television, looking for the only episode he recorded that day. He started eating as Ellen Degeneres danced on stage, and Castiel swayed his hips with her, following the rhythm of the music, a small smile on his face. 


At 6:07PM, Dean was back to his car, driving to Bobby's garage. He was feeling a lot better and was ready to help Bobby for a few hours before heading home. Maybe working both jobs at the same time was hard, but Dean knew it was all worth it. His little brother had received his diploma a few months ago, and to see how happy Sam was just proved Dean that all the efforts he put in to pay for his brother's school were totally worth the shot. He just had to pay his debts and everything was going to be great. Plus, working with his uncle was all kinds of awesome. He'd always wanted to be a mechanic.

He parked the Impala behind Bobby's and walked in, all set for three perfect hours of cars and classic rock waiting for him.


Wednesday. Half of the week is behind me, thank God, thought Dean as one particularly insistent customer left the shop. It was almost time for his and Benny's break and he needed to eat something before he started to auto digest himself. He walked towards the back store to join Benny when suddenly, someone called his name.

"Mr. Winchester!"

You have got to be kidding me.

Dean took a second to put a smile on his face and turned around, facing his boss. Zachariah almost never came to the shop, being too busy doing some paperwork in an office somewhere else. Rumour had it that he wasn't actually doing anything, but no one could prove it. Dean hated the guy, and he was pretty sure the feeling was mutual.

"Hi Zach."

"How's the day going?"


They looked at each other for a few seconds, Zachariah waiting for Dean to elaborate, Dean certain that if he opened his mouth again, he'd regret it.

"Where's Benjamin?"

"On his break. Speaking of which, it's mine too" said Dean, turning around. "Have a nice day."

"Don't come back late, Mr. Winchester. If you take more than the hour you are supposed to, I'll take it off your pay check. Enjoy your lunch" Zachariah answered, fire in his eyes.

What an asshole, Dean thought, entering the back store. Benny was waiting for him beside his locker.

"That customer didn't want to let you go, huh?" Benny laughed.

"Yeah. And Zachariah showed up just after. We need to get out of here."

"Can't agree more. By the way, I'm coming with you. I forgot my lunch at home."

Dean smiled.

"Finally! I knew it was bound to happen. Come on, if I don't eat in the next 5 minutes I'm going to die."

They walked together to the Cheesecake factory, which was only a few steps away from MicroCell. As they entered the restaurant, a hostess welcomed them.

"Hey Dean! How are you today?"

"I'm great, thanks Tessa. How are you?"

"I had a rough morning, but I feel better since you're here" she said with a flirtatious look. "Table for two?"

"Yes, please" Dean replied with his best smile.

Tessa took two menus from under the counter and stepped to the right.

"Follow me. I can't give you your usual table today. We have a group of 16 people taking half of Jody's section, and the other half is already reserved for another group."

"Well, tell her I say hi, will you?" Dean said, following Tessa, Benny not far behind.

"Sure, sweetheart."

She dropped the menus on a small table on the far side of the restaurant, motioning them to sit.

"Enjoy your meal, guys" Tessa said, slightly brushing Dean's arm as she walked away.

Both men sat in front of each other as a waitress came to give them glasses of water.

"Can I bring you something else to drink while you look at the menu?" She said, looking at Dean.

"Not for me, thank you... Lisa" he answered, looking at her nametag.

"Ok well, I'll be back in a few minutes to take your orders. If you need anything..."

"We'll let you know" he said with a wink.

She walked away, swaying her hips way more than necessary.

"Am I invisible or something around here? She didn't even asked ME if I wanted something. She didn't even look at me!" Benny said, opening the menu.

"I'm telling you man, I can't walk around without having at least three women - or men for that matter - at my feet."

"You are so fucking pretentious, man, seriously. No wonder they can't stand you more than a night."

"Shut your face. I can get anyone I want, whenever I want, for as long as I want. You're just jealous" Dean said "and you have to try their burgers, they are delicious" he added, seeing Benny going through the menu a second time.

"I'm not jealous. If I don't bring someone home with me every time I go out, it's because I don't want to, not because I am ashamed or because I don't know how to get someone or whatever you might think. And I'll take the same thing as you" Benny said, raising his hand so Lisa could see they were ready. She raised a finger, showing she was coming in a minute. "I just think you can't actually get anyone you want. That's not how life works."

Lisa walked to them, cheeks a bright pink taint.

"What can I get you, boys?"

"We'll take two Americana Cheeseburgers. Extra cheese and extra bacon in one of them" said Dean.

"Comin' right up!" Lisa said, turning around with a stunning smile on her face.

Dean looked at her walking away, biting his bottom lip, envy in his eyes. Maybe he'll ask her when she finishes her shift. That is, if she doesn't tell him by herself.

"Ok, you know what?" Benny blurted out. "I am so done with your attitude. I've been putting up with it for years and I can never rub it in your face. I am ready to bet a whole lot of money that you can't get everyone. Next person that talks to us, is the one you have to make fall in love with you. If you do it, you win."

"That's too easy, man, that girl is already so into me, if I make a move, she'll come home with me tonight without hesitation."

"I'm not talking about sex, Dean. I'm talking about love. I'm talking about waking up in the morning and wishing you could stay in bed with that person instead of running away as silently as possible. I'm talking about someone who can deal with your ostentatious self for more than 24 hours and enjoy doing so."

"You can deal with me for more than 24 hours."

"First of all, I'm not into men -"

"Give me one night, darling" Dean cut with a wink.

"- And second of all, I know you, and I know it's just a cover for all your insecurities" Benny continued without flinching, accustomed to Dean's salty reply.

Dean suddenly got serious. He'd known Benny for a long time and they both knew talking about Dean's feelings was risky. It was like defusing a bomb : one wrong move, and you and half of the building you were in could be obliterated from the surface of the earth. He looked Benny straight in the eye, all fun erased from his face.

"Fine" Dean answered. "What are the stakes?"

"If you succeed, I'll help you pay your debts. You know I have the money. I can help."

It was true. Benny's parents gave him a huge inheritance when they died. The only reason why he was working was because he got easily bored and wanted something to do on weekdays.

"And if I fail?"

"I put your precious Baby on lockdown for three months. You can't drive her, you can't polish her, you can't even look at her."

"Are you planning on stealing my car?!" Dean exclaimed, outraged.

"Not stealing. Confiscating."

Dean looked at him, his forest green eyes wide with shock.

"You can't be serious."

"Oh believe me, I am."

"how would I get to work?"

"I can drive you. We did it for a while in college, it was fun. I don't mind doing it again."

Dean thought about it for a few seconds. He still had fifty grand in debts, which was a lot, and Benny paying a part of it, even if it was only a thousand dollars, would be a miracle. He also knew Sam would help him whenever he'd get a job, but the guy just got a house with Jess and Dean would feel like shit to ask his brother for money. It was Bobby's and Dean's decision to pay for Sam so he could live his dream, there was no way he'd crush his perfect life right now.

"How much time do you give me?" Dean asked.

"Let's say... six months?" Benny answered hesitantly.

Dean bit the inside of his cheek.

"You got yourself a deal. The next person that talks to us, women, men, whatever. I'll get him or her."

Benny looked surprised.

"You know you'll lose, right?" he said.

"Watch me" Dean answered with a predatory look.

The two men were so concentrated on each other that that they didn't noticed the waiter arriving at their table. He cleared his throat.

"Sorry to interrupt. Two Americana Cheeseburgers, one extra bacon and cheese?"

Dean and Benny looked up at the same time, surprised to hear a male voice. The waiter was wearing the Cheesecake Factory uniform, of course, but it looked... different on him. That's what Dean thought anyway. His white shirt was tensed over his strong arms, his colourful tie was hanging just the right way from his neck. He had the hands of a pianist, long and soft, and Dean thought for a second about holding that hand, and how comforting it would be. He had a strong squared jaw and he had stubble just the way Dean liked it. His hair was a dark brown, almost black, which only made his eyes look even brighter. They were a gunmetal blue, a color Dean only saw on cars until today, which was oddly exciting. And his lips.

God, his lips.

That was probably the most arousing thing Dean had seen in his entire life. He couldn't even describe how bad he wanted to kiss those lips and make them his. He wanted to bite them and make them swollen, and to continue until they both couldn't take it anymore. They looked so kissable, so perfect, like Dean's mouth was made to touch the waiter's. He couldn't stop staring. 

"Huh... I... Guess I got the wrong tab -"

"NO!" screamed Dean, Benny and him getting out of their numbness. "No no, sorry, the extra cheese and bacon is mine, thank you."

"Extras for you, and here's for you. Enjoy your meals" he said with a dazzling smile.

Oh Lord, my heart.

The waiter clapped his hands together and walked away. Dean let his gaze follow him until he couldn't do so without breaking his own neck. He turned back to Benny, to see his friend had the biggest grin he'd ever seen.

"You are so going to lose this thing, brother" he laughed, taking a sip of water. "I can already see you crying at my door to get your car back."

"Shut your face" Dean replied. "I'm gonna make it happen."

"Dude, I've never seen you that awkward in front of anyone. You completely lost it."

"I... It wasn't... I didn't... Oh, you know what, fuck you. I'll show you" Dean said, taking a huge bite from his burger. 

"You wish" Benny answered.

This is going to be a whole lot harder than I thought it would.