Title: Not supposed to pt.1

Pairing: Mobster!Dean Winchester x PI!Female!Reader

Word count: 3700

Published: 6 August, 2020

Author: Heloise Daphne Brightmore

Notes: I wrote this little piece for a tumblr challenge. It was supposed to be a one shot of some kind, but there will be 4 parts to it after all, because I kind of ran away with the story line.

Beta: Dream821 [Tumblr]

Dean Winchester was born to be a charmer.

His mere presence projected confidence.

You were not supposed to realise the mischievous glint in his green eyes looking around the people he surrounded himself with. You were not supposed to stare at the charming smirk sitting across his handsome face. Your throat was not supposed to dry out looking at the way he ran his fingers up his woman's thigh seductively. You were not supposed to feel attraction towards him.

You were supposed to be doing the job you have been hired for.

It's been weeks since you have been following him around, trying to keep a low profile. You were aware of his reputation. You couldn't risk getting caught by his man. Many reporters and investigators disappeared around him and you had a strong suspicion about where to.

You knew all about the rumours, still you followed him shamelessly to his own club. You were seated a couple of booths away from him, sipping on a passion fruit martini, whilst subtly keeping your attention on him. His hands were busy playing with the blonde woman's thigh, while he was discussing something with the other men around him. You couldn't take your eyes off the way his black suit strained over his muscles, as he firmly wrapped his thick fingers around her leg.

Your eyes wondered over to his stubble covered jawline, before they wondered higher stopping on his parted mouth. His tongue darted out to water his lips, slowly pulling it back, biting on his lower lip, satisfied by his own actions, looking over to the mesmerised woman beside him. She was shamelessly ogling his movements, causing a playful smile to grow wider on his face. She was done for. You let a small smirk appear on your face at her desperate behaviour. Oh, you knew she would be begging him to take her within minutes, wherever he wanted to, losing all her pride. If she had any at all.

Your smile died down as his green orbs landed on you. You were not supposed to reveal even your existence. Panic grew stronger in your chest, but you kept it under control. You couldn't make a mistake now. Not after working so hard on his case for weeks.

He offered you a cocky half-smile, throwing you a playful wink, certainly aware of how dashingly attractive he was. You returned the expression, lifting your glass as a gesture to enjoy his evening. He followed your movements and nodded in approval.

However, you didn't have the opportunity to watch him any longer as two suited up man stood firmly in front of you. You tilted your head in confusion, knowing you have done nothing, but drink and sit looking pretty.

The taller man bent down to your ear, attempting to be louder than the music blasting from the speakers. "Ma'am, please do come with us." His tone was demanding, his seemingly polite request only formality.

"Why would I?" You questioned his unexpected behaviour.

"We have to talk to you, ma'am." He replied impatiently, still keeping his politeness.

"I haven't done anything. Why can't I just enjoy my drink and relax? I'm quite certain this is not the service I have paid for." You tried to play the part of an entitled rich woman. If you have learned something throughout your years of experience, it had to be adaptation. You were good at pretending to be anyone, almost to a point where you forgot who you really were.

"I am sorry, ma'am, but this is not a request. Unfortunately if we have to, we will use necessary measures to be able to talk to you." He replied, his demeanour though and confident. You could feel your heartbeat quicken under your rib cage. You had a bad feeling, but you couldn't risk getting more attention than you already had. You heaved a deep sigh and stood up, smoothing the silky, black, knee length dress over your body, placing your clutch bag around your shoulder as elegantly as you could.

You didn't have a chance to look at the green eyed man, you obediently followed the two bodyguard looking man out of the club to a back alley, which you were sure wasn't the entrance you came in. You looked up at he two man as they closed the door behind themselves. You waited for them to talk and within seconds, one of them did.

"I am very sorry, but it has to be done." The one from earlier spoke, reaching behind his back, pulling out a black gun. He pointed its end towards your forehead. Your eyes widened at the sudden attack, your heart rate abnormal at this point. You could feel yourself sweating as the realisation of your death kicked in.

You couldn't let it happen. You were not weak or one to give up.

It felt like slow motion as his finger closed in on the trigger, deciding your fate. But you didn't let it. You jumped out of the gun's way and started running to the entrance of the alley. You heard two other gun shots being fired, both very close to your moving body.

You felt their presence behind you, hearing their foot steps loud against the ground. Reaching the parking lot, you jumped into your car. You tried to put the key into the ignition, but your shaky movements seemed to delay you.

As you finally started the car you drove out of the parking lot, straight on to the high way. You let out a deep sigh you didn't remember holding in and felt relief wash over you. But it didn't last long. You could see a suspicious black car with dark windows from your rear view mirror. You knew they were following you. They kept tailing you, keeping on you even when you went triple over the speed limit. At this point you didn't care how, but you had to throw them off.

You turned down to a fairly abandoned road, trying to get them off you by going through small little alleys. But they were fast. Wherever you drove, they were right behind you. You could see a second car join behind them and you felt your hope slowly disappearing. You weren't a race driver or a professional fighter. Face to face or in a car, either way you were losing.

As much as you just wanted to give up at this point, you had more pride than that. You would have felt disgusted of yourself for consenting to your own murder. Hell, you were better than that.

You turned down a small street, heading towards a crossroad. You didn't see the other cars following and you felt a small hope returning, thinking you successfully threw them off.

But you were wrong.

The minute you reached the crossroad, you felt a powerful impact from the side. Your airbags forced the air out of your chest, your seat belt cutting into your neck, whilst keeping you fairly in place. You hit your head into the window, feeling a warm liquid pouring down your face, before it poured back up as your car flipped over, stopping on its roof.

You were half conscious. You were gasping for air, but the only thing you felt was your blood pouring back into your nose, stopping you from regaining your breathing. You were coughing abruptly, trying to pull the seat belt away from your chest, but you miserably failed.

The door of your car opened with a loud creaking noise and you could just about make out a blurry knife cutting through your seat belt, before someone quickly caught your falling body.

You felt the hard asphalt under your back, still trying to get more air than blood into your lungs. Your saviour turned you on your side, helping you to cough up the excess blood you have been harbouring in your lungs unnaturally.

You looked up at the person and you saw the same pair of green eyes you admired shamelessly earlier that night, although this time it was all a blur. But that wasn't right. You concluded your findings to be a simple mind-game in your desperate situation.

"You idiots." You heard a deep baritone voice, but you didn't have the energy to concentrate on its owner.

You didn't want to give up the fight. You didn't want to give in, not knowing what would happen next. But you didn't have a choice anymore. Your body went limp and your eyes closed down involuntarily, sending you into an unconscious state, which you simply identified as death.

Wrongly.

You could feel your body being lifted and placed on a soft material. You wanted to scream in pain, but you couldn't hear your own voice.

You couldn't recognise your surroundings and your eyes were fighting hard against your will to open them. There was a gentle touch on your palm and a small pricking feeling on the back of your hand. You could feel it all. You were there, still far away from yourself. Your senses were reduced.

The material under your hand felt refined. You gently ran your hand through it, enjoying the feeling of its softness. You started to notice more of your surroundings. The light breathing beside you, the foot steps farther away from you, your mattress dipping under a heavy weight.

You attempted to open your eyes, but before you even had the opportunity to keep them open, they flattered close once again. It did take you a fair amount of tries before you could keep them open, against the bright light blinding you.

"You're awake." You heard a deep, husky voice from beside you. You turned your head, groaning in pain. Your spine fought hard against your movements. You looked up at the man whose green irises watched your every move eagerly. You weren't sure if you felt terrified for being this close to him or your heart was beating erratically in anticipation of his presence and sweet, woody cologne, which involuntarily found its way into your nostrils.

"Khm." You replied, feeling your throat dry and painful. You tried to clear it, but you were lacking the necessary moisture to do so. As if he understood you, he placed a hand behind your back and helped you up into a seated position, against all your painful cries. Your ribs were your worst enemy at this point, as if they tried to poke through your already scraped and sensitive skin.

Dean gave you a glass, half-full of water and a straw. You quickly slurped on the life-saving liquid, ignoring being decent, noticing how much your system has been craving for it.

"Better?" He asked as he took the empty glass from you and placed it back on the night stand beside your bed.

"Yeah." Your tone was low, but nowhere near weak. You looked around and saw a gigantic room with windows from floor to ceiling, furniture with all the most expensive wood work. Even your presence didn't belong in such expensive bedroom.

"I know you've been following me." He stated without hesitation as he sat down on the edge of your bed. Your head shot up, your eyes fixed on his green ones. He definitely wasn't the type of person who danced around the bush. He went straight to the point. "Why?" You weren't sure how to reply. His eyes were looking at you as if he could read you, but you didn't give in. You knew it was a tactic. He must have had the experience to get people talking.

"Why would I tell you?" You asked firmly, with more confidence than you intended.

"Because I saved your life." He retorted.

"I didn't ask you to." You replied, shrugging your shoulders casually. It was his fault that you got into this mess in the first place. Sending his man after you was low, but you knew his reputation, you weren't surprised.

"A bit more gratitude would go a long way." He replied.

"For what? For sending your people after me? For almost killing me? Why am I supposed to feel gratitude when this was all your fault to begin with?" You questioned him, causing his brows to run high in surprise.

"I think you are mistaken, sweetheart." He scoffed with an amused look on his face.

"Don't call me sweetheart." You hissed.

"Well, sweetheart," He emphasised your new nickname. "I didn't send anyone after you. Yes, they were my people, but not anymore." He stated, making you frown.

"What do you mean?" You asked curiously.

"I was aware of you following me, but honestly, you are a pretty sight and I didn't mind your presence. My people on the other hand, decided to go on a personal mission without discussing it with me. I didn't know that they were planning go after you, up until they walked you out of my club. I knew that was suspicious." He explained casually as if he was reading a simple story from a book.

"Why did you save me then? You do not know what kind of information I have on you." You knew you were basically your worst enemy at that moment, but you just couldn't understand his way of thinking. He started loudly chuckling at your words, letting his head fall forward momentarily.

"As I said, you are a pretty sight." He let a cocky smirk take over his face. "And although you might have something on me, I do not hurt innocent people. I have a reputation, which I am very well aware of. I am indeed an awful person, but I do not hurt people who haven't done anything to me." He replied, his tone beyond sincere. You just felt the need to believe every word of his. "So? I explained to you what happened and on top of that I saved your life and gave you the medical attention you needed. I think I deserve the information, Miss. Y/L/N." He spoke with that charming half-smile and seductive voice of his. Your last name rolled of his tongue so gracefully, in other circumstances you would have felt pleased for your name to be called by him.

"You know my name..." You breathed, feeling weaker, knowing your identity has been revealed. But you didn't expect anything else. He had connections. A lot of them.

"Yes, I do." He replied confidently. "And I know much more. I also know that you are a Personal Investigator." He stated.

"Then you know why I have been following you." You replied.

"I am assuming you have been hired to gather information on me." He nodded.

"Then why are you questioning me?" You frowned, being unable to understand his intentions.

"Because I need to know who hired you, why and what kind of information you need to provide on me." He replied.

"And why would I tell you that?" You raised a brow questioningly.

"To make it up to me for going out of my way to save your pretty little ass." He leaned closer, his green irises wondering between your eyes and lips, making his intentions very clear. You could feel his breath against your lips and you couldn't deny the affects he had on you, but you were smarter than to gave into his seductive behaviour.

"Is this technique supposed to be working on every woman?" You questioned him, letting your eyes wonder over to his lips, before returning back to his eyes. A cocky grin appeared on his face as he licked the side of his lip, capturing your eyes for a moment longer than it was supposed to be appropriate. Oh how you wished to feel that tongue running through your own lips, but you were not one to just give in that easily. You needed to think with a clear head. "I am not planning on giving you any information." You clarified your stance.

"So what's your plan, then? You have been exposed already. I am planning to be even more careful than before." He smiled confidently with a raised brow, confirming his sincerity.

"I will give back the job. This way I don't have to give you the information on my client and I don't have to follow you either, knowing you would hide your tracks even better." You shrugged. He kept his gaze on you, this time no mischief present in his eyes. You didn't understand the look on his face, but you didn't have to. A loud knock broke the moment as a man in a black suit entered the room.

"Boss. We've got a bit of a problem." He spoke hesitantly, not knowing if you were supposed to hear his words. Dean nodded at the man and stood up from the edge of the bed.

"Look, you can go home when you get better, but for now, just stay put and rest. The doctor will be here in about 2 hours to check on you. Until then if you need anything, just pick up the phone and press the star key." He spoke as he pointed at the vintage looking phone by the nightstand. "One of my staff will pick it up and help with whatever you need." He concluded. He started walking to the door, but before he closed it behind himself, he looked back at you. "Rest and don't try to act though. You are not healed yet." He gave you a light warning, almost as if he cared about you. His gentle, worried act definitely confused you. You just couldn't see the mean killing machine people have been talking about.

Either way, you didn't plan on staying. You forced your aching body to move and placed your feet down on the ground, whining in pain. You took a couple of deep breaths, trying to get your body used to the uncomfortable feeling it provided.

You looked around the room, searching for your cloths, before finding it on a chair at the other end of the room. You were currently wearing a black t-shirt which seemed to be double of your size and a black pair of shorts, which silky material screamed how expensive it must have been.

You forced yourself up into a standing position, limping over to the chair, holding your weight on whatever you found on your way, be it the end of the bed frame or the wall beside you. As you reached your cloths, you realised they were completely intact. You were sure they were partially destroyed in your accident. You picked up the black silky dress to reveal a label attached to its side. You frowned hard at he revelation. He bought you a new dress. You just couldn't explain why he was so... kind to you. He was supposed to be anything, but. You shook off the confusing thoughts and dressed up, breathing heavily as your pain returned ten times stronger.

You picked up your clutch, checking if all your items were in it. You took your ID card out, letting a scoffing sound leave your lungs. Of course he knew your name. You shook your head, feeling silly, before you walked out of the room.

The place was huge and majestic. It screamed elegance and you just felt so out of place. You hurried down the corridor, searching for the stairs. At the end, you finally found it with a nicely carved wooden door leading you towards the exit.

You were almost out, when a voice stopped you.

"Miss?" You shot up, meeting a fairly wrinkled old man, his blue eyes looking at you questioningly. "Where are you going?" He asked. He was wearing a black and white butler costume, one that you have only seen in movies.

"I am going home." You replied confidently, attempting to hide the guilty feeling of being caught out.

"But my Master said you would stay until you are healed." He explained, suspiciously eyeing you. "Ma'am, you don't seem to be healed just yet." He stated, making you want to roll your eyes.

"I am perfectly fine. I have to go. I have to take care of things." You explained.

"Would you like to leave a message for my Master?" He asked, but you just quickly shook your head.

"No, no, it's fine. Thank you for everything." You nodded and left the mansion feeling uneasy. You just couldn't cope with the huge building, its expensive exterior, having a butler and someone being called Master. It was just emotionally overwhelming on top of your physically exhausted and painful state.

You walked out of the huge driveway, surrounded by beautifully cared for gardens and exited through the few meters tall metallic gate. You pulled out your phone and ordered a cab, wanting to get out, before Dean decided to appear unexpectedly to drag you back into his house.

The cab took a good fifteen minutes to arrive, but before you knew it you were seated in the back, heading home finally, wanting nothing but a good shower and your own, overused mattress.

As you arrived home, you threw your shoes and bag off by the door and headed straight for the shower. You didn't take longer than ten minutes, realising that your rumbling stomach might not have been well fed recently.

Up on finishing soaking your body, you quickly made a ham and cheese sandwich, not wanting to bother cooking. You brought it to your room, eating above a plate, seated in your bed, whilst watching some silly tv series to get your mind off the recent events.

Before you knew it, your slumber took over your tired body and mind, letting you enjoy your well deserved rest.

Notes: If you enjoyed it, don't forget to like the chapter. Thank you :) I am also taking requests. If you have any, please just let me know.

I do not accept requests with suicide, suicidal thoughts and self-harm. I'm sorry, but those are subjects, that I do not cover for personal reasons. Anything else, let me know.