Title: Not supposed to pt.2

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

Word count: 3071

Published: 15 August, 2020

Author: Heloise Daphne Brightmore

Warnings: Sexual references, heated make out session

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]

You could hear your phone ringing, but you were too tired to answer it. It rang for minutes straight, and as you started getting frustrated and feeling fed up, you threw your pillow at it. Your phone ended up on the floor, silence taking over the room. You heaved a deep sigh, turned over in your bed and tried to return to your dreams, but you weren't successful. Your phone already woke you up enough to not be able to go back to sleep.

You got yourself out of your bed and headed to the bathroom to get your morning routine started. As you finished and walked out, the door bell started ringing frantically. You frowned and quickly looked into the mirror. Your pink pair of Minnie Mouse shorts and black Guns 'n' roses t-shirt were anything but appealing, however you didn't have time to change as your visitor seemed to be awfully impatient.

You walked up to the door and opened it to find the last person you have expected anywhere near your flat. Your wide eyes were attached to his green ones, his lips formed a line in anger.

"Mr. Winchester?" You breathed in surprise.

"I told you to stay put." He stated firmly, his hands crossed in front of his chest. Without hesitating, he entered your flat without an invitation.

"Sure, come in." Your voice was full of sarcasm directed at your intruder.

"Don't be cute. I told you to rest, but you didn't listen." He scolded you and for a moment you felt like a child, incapable of taking care of herself. But then you composed yourself.

"I did. I was resting in my own room, in my own bed. Which brings me to the next question. What are you doing in my flat?" You raised your brows questioningly.

"Well, you didn't pick up your phone. I don't like when people try to ignore me." He shrugged, as if it was obvious.

"Firstly, I ignore whoever I want. Secondly, I was resting just like you told me to do. Thirdly, I do not know your number and I don't pick up unknown numbers." You opened your arms as if you were offering him your explanation.

"Now you can save my number for future reference." He smirked mischievously.

"Why would I need you number?" You tilted your head in confusion, although a part of you felt perhaps a tiny bit happy about it, but you didn't dare to admit it to yourself.

"I am the kind of contact information that you need if anything happens." He stated confidently and while you knew being associated with the kind of person he was, with the kind of reputation he had, was not the best idea, you still felt drawn to him. You heaved a deep sigh and walked back to your bedroom, leaving him in the living room.

"Fine, it's saved. Happy now?" You asked as you walked back out and finished typing on your phone. He was standing there with a cheeky grin across his face, running his eyes over your body, making you frown. "What?" You asked.

"I like your outfit." He chuckled, which you simply replied with an eye roll.

"Sorry, Gucci isn't my go to brand." You shrugged as you walked to the kitchen to prepare something to eat.

"What are you doing?" He followed closely behind.

"I'm hungry. I have to make some food." You spoke, feeling as if you had to explain it to a child.

"Let's go out to grab lunch." He offered and you turned around with a skeptical look on your face. "We can call it a date." He chuckled playfully.

You had to think for a second, but you really were starving and having food ready on the table sounded better than the whole process of cooking. "Fine, but not a date." You clarified.

"Sure." He nodded with a wider grin this time.

"It's not." You argued, but he just nodded, making you even more frustrated. You groaned, feeling utterly annoyed and headed to your room to dress up and get ready.

Within half an hour, you were sitting in his expensive silver Porsche. You didn't even dare moving, fearing you'd destroy anything around you. You would never in your life earn enough to pay him back.

"You seem tense." He spoke, barely taking his eyes off the road.

"I am sitting in a million dollar car. I'm not used to it." You replied, running your eyes across the leather interior. He chuckled at your nerves.

"You look good in it though." He winked playfully, which earned an annoyed eye roll from you.

"I'm sure I do." You scoffed, but a small smile did find it's way across your face.

You arrived to a rather posh looking restaurant. Men wore expensive suits, whilst the ladies had the prettiest looking gala dresses on as if they have just left a charity event. You felt out of place with your simple red dress and cheap jewellery. You nervously put your weight from one leg to the other, looking around the elegant, dim lit restaurant, whilst your company talked to a barely older man, who seemed just as important as he was.

"You're doing it again. What's wrong?" He asked, his voice concerned as he returned to you.

"I just don't belong here. I'm the kind of person who goes to the closest little restaurant, ordering a good old burger." You shrugged.

"You didn't seem so out of place when you were in my club." He raised a brow.

"I am good at adapting to my surroundings, it doesn't mean I enjoy it." You replied, running your eyes around the place once again.

"Do you want to go somewhere else?" He asked and you finally decided to look up into his green eyes, catching yourself off guard at his attentive manners. You were glad he offered to change restaurant so generously, but you were already there, you didn't want to just waltz out rudely.

"It's fine." You shook your head and he nodded. You walked up to a table and he pulled out the chair for you to get you comfortably seated, before he took his place too. You were given a menu by the waiter and you quickly started searching for something that sounded anything like the food you usually ate. All the french names made your head spin. It wasn't your first time in such a high-end restaurant, but you were never a big fan. Looking at the prices, you heaved a deep sigh, knowing it would cost you a fortunate to pay for it.

"You are adorable." He chuckled. You looked up at him and offered him your deadliest expression as a reply. "It was a compliment, you don't have to try to kill me with your eyes." He smirked.

"Unfortunately, trying is all I can do." You retorted, causing a wholehearted laughter to leave his lips. His joyful expression made you feel warm. You just couldn't see that dangerous side of his everyone talked about. You were rather mesmerised by his playful, but kind behaviour.

The waiter brought over a bottle of wine, which you were sure cost more than a monthly salary of yours, but you had to conclude how nice its sweet taste felt against your tongue. When the waiter returned, the green eyes looked at you with a mischievous glint, before two burgers were ordered, making the waiter hitch in surprise as he left.

"Why?" You asked.

"Because I want you to feel comfortable." He smiled sweetly, once again making you feel dizzy.

"Thank you." You nodded, biting on your lower lip awkwardly. He was nothing like you imagined him to be and it frustrated you to realise he wasn't as bad as the rumours said he was.

The waiter soon brought your two burgers over with a skeptical look on his face, but you just offered him a gentle smile in return.

"I'm glad, we can finally enjoy each other's company." Dean smiled lightly.

"Why would you think that I enjoy being with you?" You asked with raised brows and a tiny small smile hiding away at the corner of your lips.

"You see, I am very good with three things. Business, women and my hands." He smirked mischievously. You weren't sure if that was meant to be a sexual innuendo, but from what you have gathered about him, he definitely had a strong liking for pleasuring women in all kinds of way.

"With your hand?" You asked chuckling.

"I knew you would pick up on it. You are smart after all." His devilish smile forced your eyes to linger over his lips longer than it was appropriate, before you finally composed yourself.

"And how would you know?" You asked.

"I know more about you than you think." He stated suspiciously.

"And still, I barely know anything about you." You gave him a questioning look, begging silently for him to say more.

"What would you like to know?" He asked, opening his arms as if he was an open book.

"Why did you save me? And don't come at me with that bullshit about being a pretty sight and having a sweet little ass. It might work with others, but not with me." You scoffed. He stopped to think about it for a mere second, before a gentle smile took over his previously mischievous grin's place.

"Because you're intriguing. Don't ask me to explain it because I can't. There's just something about you that caught me off guard." He replied sincerely. "I had weeks to study you after all." He added.

"I am not sure if I should take that as compliment or if I am supposed to be terrified to have a creepy stalker around me." You chuckled.

"Well, are you scared?" He asked.

"Surprisingly, no." You shook your head.

"Then it was a compliment, wasn't it?" He bit into his lower lip, forcing your eyes to follow his movements.

"I guess." You replied, turning your attention back to your food.

You were happily enjoying your food and the easily flowing conversation between you. Whether you wanted to deny or not, he was definitely a pleasant company and that feeling of being drawn to him became stronger by every minute.

As you finished your food, you had a tiny argument over not letting him pay for your food, which you simply solved by taking his card from him in a childish manner and he finally agreed and let you pay for your own share. However unhappy about it he was.

"Are you still sulking?" You asked laughing whilst he drove his car.

"I am not sulking. I am pissed off."

"I won't let you pay for my food." You tried to make him understand.

"I invited you for lunch. I wanted to treat you like a lady, the way you deserve it." He spoke firmly.

"Come on, Dean..." You called out to him, realising you have just said his first name.

"Dean?" He asked with a grin.

"I mean..." You wanted to explain yourself, but he stopped you.

"No, I like that, Y/N." He smiled and the way your name rolled off his tongue made you feel relaxed for some unknown reason. You let yourself smile, but turned your head towards the window, not ready to reveal your little happy moment in front of him. But he did see it just fine from the side view mirror.

A couple of minutes later you were already walking up the stairs to your apartment, Dean following behind closely. You stopped right in front of your door and turned around to realise he was standing barely an inch away from you. You could smell his woody cologne once again, filling up your head with the attractive scent, quickening your heart beat.

"Thank you for today." You spoke, your tone low.

"It's the least I could do. You got into trouble because of me." He replied, lifting his hand and running his finger across the bandage on your forehead. "I'm really sorry about it." He said in the softest tone you have heard from anyone.

"It wasn't your fault, was it? You don't have to apologise for it." You shook your head with a gentle smile, which he gladly returned.

"Would you like to have dinner with me tomorrow?" He asked hopefully and you weren't sure how to reply. You certainly enjoyed his company, but he wasn't the best person out there. You knew the kind of things he dealt with and you didn't want to get in trouble. "I know what you are thinking. It's what I do, isn't it?" He asked and you slightly nodded. "But you feel the attraction between us. I know you do. Just give it a chance." He spoke softly and you couldn't explain why, but you wanted to give into it. His mere presence made you feel excited as if he was your own personal drug.

"Fine." You replied, making him grin happily.

"I will text you when I can come to pick you up." He stated as he hinted a small kiss on your cheek. You were surprised to realise he wasn't aggressive about forcing you to be with him, but it just made you feel even more curious about who he really was. You nodded at his reply and waited for him to leave your building, before walking into your apartment with a huge grin across your face. You were not supposed to feel so giddy, but you couldn't stop yourself.

As soon as you collected yourself, you picked up your phone and called your boss and informed him that you were able to go back to work. He told you off for not resting and put you on a mandatory vacation for another week, making you roll your eyes, but accepting his orders.

You quickly searched in your contact for your client and pushed the call button, waiting for him to pick up. After a couple of rings he finally picked up the phone and greeted you warmly. You explained to him that unfortunately you would not be able to work on the Winchester case anymore, because of your health problems. He was taken aback, but he accepted your withdrawal.

For the rest of the night you just sat in your bed, watching some random series on the telly, but your mind wondered another path. You were excited about seeing Dean once again and although your mind was screaming at you for being cautious and careful, your heart said the complete opposite. Be bold, be brave, go and enjoy yourself.

"You were sitting on the edge of his table, right in front of him. You placed your black high heels between his legs, opening your thighs wider. You could see the lustful look in his eyes as he darted his tongue out to lick across his lips.

He placed his big hands over your thighs, gently moving it upward, hinting a soft kiss on the inner skin. You heaved a deep sigh as you felt his lips touch you. You wanted to feel his hands and mouth all over your body, craving for anything he was to give you.

He stood up, towering over you. You got hold of his tie, slowly pulling him down to you just enough to feel his lips graze your own. He was impatient, fed up with your games. He wanted you then and there. Without hesitation he attacked your lips, sucking on your bottom one, making you a moaning mess. His tongue found its way into your mouth massaging yours with his own. You linked your arms behind his neck, tugging harshly on the end of his hair, pulling him even closer between your legs. He groaned at the friction of his bulging trouser against your wet core caused.

His lips found their way to your neck, harshly sucking on your sweet spot. You were completely out of it, moaning his name in pleasure. Your hands found their way under his white buttoned up shirt, caressing his toned abs with your finger nails. He bit into your neck roughly, making you scream out in pain, before he hinted soft kisses on the same spot to absorb the aching sensation."

You shot up in your bed, panting heavily. Your dream was beyond realistic. You stood up to realise your underwear was drenched. You loudly growled, feeling frustrated as if you were a hormonal teenager.

You headed to the bathroom to take a shower and get your morning routine started, which looking at the clock was rather early afternoon routine. It was fifteen past one. You hated getting up so late, but you knew you were still not completely healed, so you gave yourself a bit of a leeway.

Dean has texted you to ask you how you were doing and to let you know that he would be by your flat at 6pm. You got into a casual conversation, but you didn't feel like taking his time and your dream was still bothering you so you quickly ended it and decided to get ready.

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.