You awoke to the drone of an alarm beeping. Turning over you could barely see the clock as it read, 9:00 AM. You turned onto your back and stared up at the ceiling. Before you knew it you were thinking about Dean. It was impossible to get him out of your head. Last night was the most amazing, yet confusing night of your life. The regret of kicking Dean out weighed heavily on your mind. You reached towards your nightstand feeling for your phone. The screen declared your lack of messages. Your heart sunk, since the moment you had woken up you hoped Dean would have called or texted you. You padded off to the bathroom to shower and hopefully forget about Dean….

Dean rolled over onto his side and checked his phone. Nothing. He opened up his contact list and scrolled to your name. He stared at your name unsure of whether or not to call. He tossed his phone onto the nightstand, and rolled over with a groan. Dean couldn't figure out why you had kicked him out last night. He couldn't keep you out of his mind, and it was driving him insane that he couldn't call you.

Once you were out of the shower in your bathrobe you shuffled around in your purse until you found an energy bar. Breakfast of Champions. You checked your phone again. This is ridiculous, you thought, shut off your phone, and tossed it onto your bed.

After getting dressed you sat down on the couch only to remember last night, and move to sit on the bed, flicking on the TV. You were just about to settle in to watch whatever show was on until you heard a pounding at the door.

You walked over to the door, and slowly unlocked the it. You opened it, and found a nervous Dean. You ran your eyes over him; his hair was still wet like he just got out of the shower, he was only wearing a white T-shirt, jeans, and mismatched shoes.

Seeing your confusion Dean began, "I'm sorry, but I just had to talk to you," he paused, "I'm so sorry about last night, but just let me make it up to you. Come on a date with me…." he trailed off waiting for your response.

"Uhh, um… right now?" You asked pointing at his shoes.

Dean looked down at his outfit, "Right," he snapped his fingers and pointed at his shoes. Dean looked back up at you, "How about later tonight? 7 o'clock?"

"Uh, uh, yeah, yes, sure," you stammered.

"Sounds good," he said with a smile, "I'll pick you up at 7 then."

He stood awkwardly in the doorway for a moment then began to say, "I should go now."

At the same time you spoke up, "Do you want me to call a cab?"

He laughed a little, "No, I'll just go, see you later Y/N", he said stepping away from the door.

"Yeah, see you later," you waved awkwardly as he retreated down the hallway.

You shut the door and stood facing your hotel room. Dean was so confusing, but you were going out with him. And you had nothing to wear. You grabbed your suitcase, and threw it open, ruffling through your clothes. You sat down on the bed, frustrated, until you decided to get some food and go shopping. After ordering room service, and scarfing down the food you ordered, grabbed your purse, and flew out the door.

Dean couldn't stop smiling the whole ride home. He couldn't believe you were going out with him again, and he couldn't wait to see you dressed up for a date.

As soon as he got home he tossed himself onto the couch, and tried to drown you out of his thoughts with some mindless TV.

The first store was a bust, so was the second, and the third. As you walked into the fourth shop you vowed you would find something here. After at least an hour you found an outfit that was decent enough. Thanking the woman at the checkout counter you walked back to your hotel.

You had three more hours to kill until Dean came to pick you up, so you pulled up your laptop and began to look over some of your projects for work. Before you knew it you were Googling 'Dean Winchester'. You shut your laptop immediately, "What the hell" you thought. You glanced over at the nightstand the clock read, 5:30.

After a few minutes you resolved to open your laptop and not stalk Dean. After half an hour you managed to get some work done without any cyberstalking, and decided to get ready.

You were finishing the last touches of your outfit when there was a knock on the door. Glancing in the mirror one last time you went to open the door.

"Hey, Dean! Come in." You said with a smile as he stepped into the hotel room. He looked good wearing a dark blue dress shirt with the sleeves rolled up to his elbows and black pants.

"So where are we going?" You asked grabbing your purse off the bed.

"There is this great little bistro-type place around the corner I thought we could go to…" he trailed.

You smiled, "Sounds great! Lead the way."

"Here let me get that for you," Dean said as he pulled out your chair for you.

You both sat in silence for a moment until the waiter came to take your orders. After ordering Dean spoke up, "Y/N, Listen I'm so sorry for what happened…"

You put your hand up to silence him, "It's OK. Let's just forget about that."

Dean smiled and chuckled, "Alright, sounds good."

After that you two were able to openly talk and the night no longer felt awkward. Once dessert time rolled around you excused yourself to the bathroom to "freshen up"

Staring at yourself in the mirror you could only think one thing, "I'm falling for him." You shook the idea out of you head. What were you going to do anyways he lived here, and you lived in LA. This would never work, but he was still out there and you had to finish this date.

When you sat down at the table Dean began talking, "Have you ever been the the Empire State Building?"

You shook you head slowly.

"What?" he said in disbelief, "How have you never been to the Empire State Building? You know what this means, right? We're going."

"What? Now?" You began.

Dean waved over the waiter and asked for the check. "I'm taking you to the Empire State Building, and you are going to love it," he enunciated the last part as he signed the check.

Before you could say anything Dean was up, and getting ready to go. You shot to your feet as he turned on his heels to walk away.

"Hey! Wait up!" You cried after him, grabbing your jacket off the back of the chair.

Dean was waiting for you outside the restaurant on the sidewalk, "Ready?" He said in a low voice.

You nodded your head and stepped in stride with him. After a few steps Dean's arm snaked around your waist pulling you closer to him. You let out a quiet sigh reveling in his warmth.

The lobby of the building was almost empty with the occasional security guard strolling past. Dean paid the fee and the two of you headed towards the elevator. Inside the elevator you were alone with him, and you could feel how palpable the tension was between you two. Dean inched towards you, and pulled you close to him. You looked over at him and found his bright, emerald eyes looking deeply into yours. One of his gently calloused hands reached up to cup your cheek. Before you knew it his lips were crashing down onto yours, and he brought his other hand up to hold your face closer to his.

You could feel your heart pounding against your ribcage. Dean's lips were soft against your own, and he pulled away for half a second before gently kissing your jaw. You let out a small sigh of pleasure which cause him to pull away and smile while you blushed.

The elevator dinged to an end. You pulled away from Dean when the doors began to slide open adjusting your jacket, while Dean cleared his throat. Once the doors were fully open Dean offered you his hand, which you took and stepped out onto the outside top floor of the Empire State Building.

You and Dean walked to the edge of the observation deck. You stood there for a long time while Dean pointed out the different buildings in the skyline, even the building in the distance that he worked at. After walking around the deck holding hands, talking, and admiring the view, Dean offered to go visit Times Square, which you gleefully agreed to.

The traffic near Times Square was so bad Dean payed the cab driver and you both hopped out of the car and headed towards the lights. Dean pulled you closer to him as the crowds thickened in Times Square. You and Dean stood beneath the NBC Jumbotron as Dean wrapped his arms around you and tucked you closely into his chest.

Dean leaned down and whispered into your ear, "Do you wanna go back to my place, maybe?"

You knew it wasn't the best idea but you were tired of walking around, and just wanted to be somewhere private with him. You nodded in response

You looked up at the tall building as the taxi pulled up next to it. Dean led you to the elevator which you took up to the top floor. Once on the top floor you gasped, "You live in a penthouse?" you asked incredulously.

Dean chuckled, "Well I guess you could say I'm a playah," he said while unlocking the door.

You made a face, "Please, don't say that ever again."

He opened the door and motioned for you to enter. You smiled and gave him a nod as you stepped into his house.

You looked around the sleek and modernly furnished penthouse. Dean noticed your aghast stares, "What?" He asked laughing a little at your shocked look.

"Are you sure this is your house?" You replied, point at the giant wall of windows portraying the beautiful New York skyline, "We didn't just break into Hugh Hefner's New York home?"

"What? You don't believe me? I live here," he said in a convincing tone, "Look!" He pointed at a picture frame on the fireplace mantel.

You walked over to it and studied it closely. There was a picture of Dean laughing with another guy who had long, dark, brown hair. "Well, I guess you just lived in a crappy apartment, or gross motels." You said, still studying the picture. You heard Dean laughing in the background. "Who is this guy, anyways?" You asked, pointing to the picture.

Dean walked over to you, "That is my brother, Sam." He walked back to the open layout kitchen, "Do you want something to drink?"

"Yeah sure," you waved your hand behind you, "You never mentioned a brother…"

"What in the 48 hours we have known each other," Dean chuckled.

"Whatever," You said dully, turning around to see Dean holding two glasses of white wine. "Wine? Dean, you are an enigma…" You took the glass in his outstretched hand.

"I'll take that as a compliment." He tapped his glass against yours and took one big gulp. "How about some whiskey?"

You laughed, "OK, maybe you're not an enigma."

Dean turned around and walked to the mini bar and poured two whiskeys. You walked over and plopped down on the couch.

After a few more drinks you and Dean were laughing and sitting a little too close to each other for your own good. Dean was leaning in close, and you could smell the alcohol on his breath, but you couldn't help yourself. Before you knew it you were pressing your lips onto his.

Dean brought his hand up to the back of your head pushing you closer to him and not letting you leave his lips. Dean was slowly moving to lay down on the couch while you adjusted to straddle his hips, still locked in a kiss.

You pressed your hips down and felt his hardened, growing member as Dean let out a low groan.