(Y/n) was smart
That was evident Sam had seen her around campus. Only smart people made it into Stanford. Everyone knew who she was and that she one person no one wanted to fuck with. She was surrounded by rumors of the reason for her dark aura and shrouded in a cloud of mystery. But Sam never paid attention to her considering he was with Jesse and she was all he could ever need.
But (Y/n)? knew Sam oh she knew of Sam Winchester she knew more about him than he lead on. Sam Winchester was a hunter life escapee. But to (Y/n), Sam didn't matter he was just a number in the population of people in the school. Sam didn't interfere with her deals so he wasn't an issue for now but she kept tabs on him just in case he does become a problem. She kept tabs on everyone in the school. Nothing gets past (Y/n) not even the smallest detail. Nobody could pull a slick one on her.

(Y/n) was dangerous
That was obvious by the people she hung out with. The bad kids that smoked and bullied people to get their way. Nobody knows her past only that she is not one you want to try anything on. She had eyes in high places...at least that's what people say. When you fuck with her...you come up missing or dead.

(Y/n) was cunning
She knew her way around problems when they arose. She could manipulate anyone she pleased. Look at you with a innocent demeanor and give you a look that can shake you to the core. If anything stood in the way of what she wanted. It would be dealt with immediately. Nobody knew how though.

(Y/n) was powerful
Nobody knew how they just knew that she was. It radiated off of her along with an aura that instills fear into anyone that even looked at her the wrong way. Power and Dominance. You could tell she loved it that way. Just by looking in her eyes.

(Y/n) was a Drug Lord
Only those who dealt with her knew that.
Knew exactly how brutal she could be. How dark her soul was. Nobody knows about her past. But everyone knew that she had dark tricks up her sleeve. That nobody can double-cross her, Nobody can bring down her empire. She's got eyes everywhere and nowhere.

(Y/n) had a temper
She was well known for that in the crime circle. One minute calm and collective. Next thing you know she's shooting up a room full of people. Oh, and God FORBID she hears or sees something she doesn't like. You better say your prayers and hope that she's in a good mood. It may be the only difference between life and death for you.

(Y/n) was a sadist
She took pleasure in killing. She had many methods of murder and torture. It only exhilarates her when she remembers that has never been caught and that she never will be.

(Y/n) used to be a hunter.
That's how she met the King of Hell and struck a deal of a lifetime. She wouldn't sell her soul but she would give Crowley souls who fucked up a deal with her. That's where she got her power. But even the King of Hell deeply feared her. Knowing of her unpredictability. He stayed on her good side and got souls out of the deal.

Sam and Dean found out.
Sam was shocked when he found out the reason everyone feared her. A human who willingly gave the king of hell souls without selling her own? It had only come to their attention when they had Crowley tied up for questioning and noticed his sudden nervous demeanor.

"You were all calm a minute ago. Why so nervous? Huh?" Dean questioned.

"I have a business meeting I need to attend to immediately. I don't know anything will you idiots let me go now!?" He exclaimed.

"You were never so concerned with business before what's the rush now?" Sam questioned.

"This is a special client don't worry your well-conditioned head about it moose. Now a be a Good boy and untie me." He gritted.

"What special client?" Dean said grabbing an angel blade.

"I'm afraid I can't tell you that. I told you, boys, I know nothing about your current predicament that you've looped yourselves into. I did my part now do yours and untie me."

"Not until you tell us about this special about this client. What are you up to?!" Dean yelled.

"Doing my part in hell is all you need to know. You need to let me go now before my head ends up on a stick. She doesn't like to wait."

"Either way your head rolls so you either tell us or we find out ourselves." Dean threatens.

Crowley was frustrated and screwed either way. "(Y/n) (L/n), we made a deal long ago she's human but very very...powerful somehow." He muttered unwillingly.

Though the name rang a bell he wasn't too certain where he had heard it after all these years it could be anyone. So Sam looked it up and found that (Y/n) was a Stanford graduate! Top of all of her classes. Everyone always warned him to stay away from her. That she was trouble. It was even said that she was death in a pretty black skirt. But Sam never cared about her. That is until he dug a little bit too far.

"What deal?" Dean asked.

"She gets me souls and I get rid of bodies I'm afraid that all I can tell you or she'll have  my head I've already said too much!"  He fumed.

"Now, Now boys...be civil." A female voice said in a teasing manner. The voice sent a shiver down Crowley's spine. Shock and horror took over his features as he looked ahead to face the only human he's ever feared. Even more so than the Winchesters.  Sam and Dean turned around confused at how anyone got into the bunker.

"(Y/n)! You found me!" Crowley nervousness chuckled.

"Of course I would pal." She said with a smile before cocking her head to the side. "I always find you when I need to. Speaking of which...I see why you're late to our little meeting." She said looking at the boys. "Caught by the Winchesters again, I see." She said walking towards them. Dean pulled his gun out immediately.

"I wouldn't do anything stupid, Dean." She said calmly as 6 men heavily armed with automatics walked behind her. "I hope you didn't mind that let myself in." She said walking toward Crowley with a gentle smile. As if nothing was wrong. She then noticed a very familiar face. "Sam Winchester, my god look at you!" She said in awe. "You have changed so much. Mm, your hair got longer and you've gotten undeniably hotter. You're still a giant." She chuckled before sighing. "Now, I would love nothing more than to play catch up. But as Crowley so foolishly divulged...I have a business meeting." She said before staring him. Crowley shriveled as her eyes bored into his soul as she makes calm strides towards him. unlocking Crowley and grabbing him by his tie. "Crowley, Crowley, Crowley." She said in a scolding tone. "I thought we agreed that business between two...should stay between two...yet now...it's between 4?" She questioned. "Momma doesn't like the sound of that." She said shaking her head slowly.

Crowley was stuttering and choking on his own words in search of an excuse. (Y/n) had a very low tolerance for excuses and tardiness.

"Hmmm, we'll discuss this later." She said as she drags him out of the bunker with her goons following her out. Before she could completely leave she turned back to the youngest Winchester.

"Oh and Sam?" She questioned. "I don't like you burying your nose where it doesn't belong. You stumbled upon some old bones that were meant to stay in the ground...keep that little tidbit of information to yourself, Sammy..." She said before leaving Sam and Dean dumbfounded of what just happened.

Sam had become obsessed. Ever since that day he dug a little too far and found out darker things about her. He didn't understand why he kept digging but he did.

One late night during his guilty pleasure sessions of Dark Web searching for more lore on the mysterious woman he didn't notice that the woman herself was present in his room watching him in the corner of his room with her arms crossed leaning against the wall.

"Winchesters don't listen...." She sighed and Sam turned around completely shocked by her sudden presence." I should have expected nothing less. When I told you not to bury your giant nose in the corner... But you. kept.digging..." She said gritted. "I get notified every time somebody searches my name...and you..." She said slowly pacing the floor as she points as him. "Just keep searching.... and digging." She gritted through her teeth. Sam sent to stand up and then she pointed a gun at him. "Ah, ah ahhh~ Sit down Sammy..." She said motioning to the chair he was recently in.  Sam sat down swallowing the lump in his throat. She pulled his hair back roughly and put a gun to his temple. "I don't like snoopers Sammy Boy. They become a threat to me and my empire a little bit of information they can hold over my head to try and control me." She gritted through her teeth as she stared into his eyes. Upon looking into his eyes she saw something in him that sees in the mirror all the time and she suddenly felt what she had been feeling for the past week since the first encounter. She hated that fucking feeling. She let go of his head and groaned as she walked away.

"You want to find the demon that killed your Family...We can help." Sam said making her stop dead in her tracks with a snarl then she laughed.

"Sammy. Sammy. Sammy." She said shaking her head before turning on the balls of her feet and slowly walking toward him. "I like you." She said pointing the gun at him before letting it drop to her side. "Your brother is all happy go lucky with a gun shoot first and ask questions later- You however...the the 'good cop'," she said giggling. "Everyone has an angle Sammy....what's yours huh?" She asked cocking her head to the side. "What you gonna catch the big bad drug lord and the king of hell? Huh?"

"I want to help you....."

(Y/n) chokes back a laugh before letting it fall out. "Help me?" She questioned "Sammy boy! I am completely sane." She said tapping the barrel of the gun to her temple.
"I'm just a little higher on life than the rest. How could you...help me hm? You wanna strike a deal?" She mocked.

"If that's what allows me to help you...yes."

She stared at Sam before going into a laughing fit. "You look at me like I'm insane, do you hear yourself?"

"You and I are alike the only difference is you didn't have. A brother or anybody to guide you. I did you were left to fend for yourself when you were only 7 hence why you started hunting then going into the dark places in order to make a living. Yes, I want to help you..."

She started huffing and growling and Sam noticed that she was beginning to shake like the anger was consuming her.

"I don't need your fucking help." She growled before walking out of the door.

(Y/n) was infuriated.
Her henchmen were quivering in fear when they witnessed her storming through the hideout into her room without a word. Screaming and crashing could be heard in her room. She had a reputation of taking her anger out on her disposable henchmen or if they were lucky the outside world.
She ripped the room door open with a sadistic smile as her chest quickly fell and rose and she let out rabid giggles she ran out of the room with her gun in her hand as she made her way to one of the henchmen.

"I held the gun to his head." She said in a shaky voice, pulling the henchmen back in the same position she had Sam in with the gun to his head. "I HELD THE FUCKING GUN TO HIS HEAD AND I DIDN'T PULL THE FUCKING TRIGGER! It would have been so easy. Just a couple of measly seconds and boom!" She yelled as she pulled the trigger and the henchman dropped to the floor dead. "JUST LIKE THAT GEORGY!" She said letting out a maniacal laugh. "He should have been dead. But I walked away..." She said laughing before growling. "Aaaah it would have been too easy. He was too caught off guard.... I wanna see...him when his guard up...." She groaned with a malicious smile. "Wanna play a few games with my new toy...Clean this shit up!" She yelled. "Have some decency gentleman we aren't animals..." She said kindly before storming back into her room. Slowly but surely as (Y/n) has been Sam's guilty obsession. Sam had so quickly become hers. She couldn't stop herself from thinking about him. Wondering about him every second of the day. She was smart enough to know Sam and Dean would be prepared for her arrival anytime soon. So she simply kept tabs on her new little obsession.

Sam was curious if she was ever going to take him up on his offer.
He had become far more infatuated with her. Dean took notice of this.

"Please don't tell me you've fallen for the psychopathic drug dealer!"

"Dean, I want to help her. She was just like us but worse. She lost her entire family to a demon and now she wants revenge. She's hurting but she doesn't know how to deal with it so she takes it out on the world."

"Sammy, she's a person pass saving. She's made her decision."

"If it were me Dean....you know you'd never stop until I broke through."

"That's different Sam you're all I have."

"And what does (Y/n) have?"

"Her fancy hideout and dirty money. She doesn't need our help. She's a lowly criminal."

"With a hunter background. She used to help people, Dean."

"Yea? well so did Ted Bundy. Do you see him walking around?"

Sam gave Dean that look.

"No, stop with that..that look with the puppy eyes," Dean said turning away before looking back. "....Dammit, Sam..." He sighed. "We can't track her...how will you find her?"

"I have a way," Sam said smiling.

That night searched her name a couple of times in hopes that she would pop up but she never showed. A month had passed and she was a no show. Sam was beginning to lose hope in her appearance.

They had just gotten back from an exhausting haunt. Sam flipped on the light to reveal (Y/n) laying on his bed in a fitting black dress with a slit exposing her right leg.

"You simply couldn't resist, hm?" She teased as she got up. "Searching me ten times a night like a forbidden celebrity sex-tape is basically the equivalent of lighting up the bat signal- or making a spell to lure Crowley into a devil's trap. You summon me." She said smirking as she got up.  "What do you want hm? Have a sudden hankering for a little bit of Demon's blood." She teased as she circled him. "Mmmm, some old habits are hard to kick huh?" She asked. "I can get you the high you're chasing after but uh I ain't no demon pretty boy." She teased.

"I'm not searching for drugs or demons blood. How's you know about that?"

"Honey, there is a book series on your life. It's easy to find out. Plus, I have my ways of finding out things the same way you do." She teased. "So what is it? Hm? In search of some info on a lackey? Maybe a drug dealer gone demon? Or maybe you want a simple loan-"

"I don't want your money."

"Don't you know it's rude to interrupt someone when they're speaking!!" She said offended.  "You're wasting my time Sammy boy and I don't like people who waste my time." She gritted to her teeth. "Time is money! So tick tock. tick tock-" she said tapping her expensive diamond Rolex. "What is it hm?!" She asked irritated.

"I want to help you."

"You don't give in do ya? You are such a damn optimist. You give your brother hope when all else fails huh? What you wanna be my hero Sammy?" She asked laughing. "Hmmm yes~" she purred. "This'll be fun....I'll humor you Sammy boy...besides what's life without a little bit of fun?" She said before walking out of the door.

Sam and Dean took (Y/n) hunting.
Dean wasn't so happy with the idea of this seemingly psychopathic drug dealer going along with them. She found hunting to be fun. a game. But to Sam and Dean, this was serious. They had a plan, meanwhile (Y/n) went in guns blazing laughing like a crazed maniac...it got the job done. But, not I'm the way they would have liked it to be.

They found the Demon that killed her parents.
Once they had successfully tracked and hunted the sucker down. (Y/n) was relentless. Chaining him to a chair and using every brutal method in the book. Soon she grew bored and ended the poor bastard's suffering. She vanished leaving Sam and Dean to clean up the mess.

Sam was sleeping later that night when he noticed a figure at his side. He turned on the light to realize it was (Y/n). She was staring at the wall with a dazed look on her face.

"I went home to celebrate." She said simply without looking away from the wall. "I've waited my whole life for this moment and now that it's done....it seems...." She started laughing.

"You laugh to hide pain don't you?"

Suddenly (Y/n) snapped her head over to Sam. "Why don't you fear me? Aren't I a big bad psychopathic drug selling serial killer? Hm? I kill  the people you aim to protect." She asked crawling toward him before they were face to face

"Though we work on different sides of the fence but the shade of grey is that we both kill to protect something and survive." Sam said. Suddenly the energy between the two began to heat up.

"Stay still." She said as their lips got closer and they connected. The kiss fired up an emotion (Y/n) was unfamiliar with. Lust was there, need and greed she knew those all too well. But what was this other feeling? She couldn't help but wonder.

Normally she was on top but Sam took the lead and (Y/n) felt....... OK with that. Sam wasn't gentle but neither was he extremely rough. But it was enough for both of them.

Sam was starting to become a liability.

There was something about him that stirred up a storm in her. She didn't see the boys often but when she wasn't she would wonder about Sam. Nobody talked about what happened that night. But there was something between them that much was undeniable and (Y/n) didn't know how to react to it. So instead She didn't. She stopped visiting the boys.

Sam was falling for (Y/n).
He finally realized it. But didn't know how (Y/n) would react. But she never came around anymore. He wished she would.
He started doing what he knew would get her attention. Yet, nothing.

(Y/n) couldn't stay away.
He always plagued her thoughts. She craved him again. She wanted something from him. She knew what but she fought it. She tried to and her advances stopped working.
She gave in and snuck into his room as she always did.

"Where have you been!? I was-" Sam exclaimed.

"Worried?" She teased before laughing.
"I sneak in your room, put a gun to your head and you're worried about me!?" She laughed. "How fucked in their head are you?"

"I guess enough if I care for a dangerous psychopath," Sam admits.

She stared at him remembering what they had done a month ago before she went silent on him. She remembered what that foreign feeling. She wanted to feel it again...she jumped into his lap and forcefully kissed him and Sam forced her to the bed and she let him. Why was she letting this happen...she was always on top.  She didn't let him have complete control. NEVER  would she let that happen.
But she gave him enough for it to feel different.

The next day Sam woke up alone again. Like the last time.

(Y/n) was changing.
She was still a "cold-blooded killer" in the streets. Nothing would change that. Nothing kept her from making sure her name held fear in this dirty world. She found that killing lowly humans to become..boring...they were so predictable. Nobody dared to fuck her over anymore. People didn't always meet deadlines and she took care of those people the same way she always had. She longed for something different.

They had finally confessed to each other.

After a year of beating around there bush and (Y/n) trying to figure out what she was feeling they finally confessed. The confession being Sam saying how he feels and (Y/n) replying.

"I don't let just anyone fuck my brains out Sammy boy...you figure out where that leaves us.."

Dean found it somewhat funny how blunt she was on the subject. But upon remembering who she was it made sense. He wasn't too happy about the pair but couldn't deny the changes that Sam brought about in the drug dealer.

(Y/n) was done
After being with Sam for a year and a half she realized how tired she was of her other lifestyle. There was no point in it anymore. She had it all. The power, the money, She gave her position to her most trusted henchmen and stepped down from her blood-covered thrown. She continued hunting with Sam and Dean. Working with people was never her thing. But she cooperated....barely.

Sam and Dean became family.
She wouldn't dare confess it aloud. She struggled with saying I love you. But Sam knew she did. (Y/n) would willingly protect Sam and Dean. After all this time it was apparent that they would do the same for her.

(Y/n) went to hell.

It was an instant thoughtless decision.
Some foolish yet vengeful human found a way to open the gates of hell. They tricked the Winchesters into coming there. They've wanted them gone.
(Y/n) didn't have anything or anybody Sam had Dean. So she threw herself in the hole and brought the foolish human with her.
When she got there it was unlike anything she had ever seen. But she made sure that the person responsible for her being there suffered a great deal.
When she made it back she was undoubtedly not the same person Sam and Dean know.

(Y/n) was not the same anymore.
Whatever torment she endured down there changed her. Sam and Dean both knew first hand that being down there was not a trip to Disney. But getting (Y/n) to open up about it was difficult. Almost impossible but one night Sam woke up to (Y/n) rocking herself either her hair stuck to her face as she was crying and whispering unheard things. 

Sam sat up and placed his hand on her shoulder causing her to jump and she cried out backing away and fumbling out of bed to get away from a possible threat.

Sam got up and put his hands up. "Hey, hey hey...You're safe...(Y/n) look at me....It's really me. You're not..." He swallowed. "You're not down there anymore..this isn't a mind trick...It's really me."  He slowly moved toward her and she hesitated as she moved toward him and she held onto him tightly and Sam hugged back as her hyperventilating began to slowly come to a stop. 

"You're safe, c'mon...(Y/n) talk to me." 

"They caged me...made me fight...treated me like an animal for wild fights...they tortured and attempted to break me." She said in a shaken tone as Sam soothed her by running his fingers through her hair. 

"You can't close yourself off, you don't have to anymore...you're not alone anymore." He said to her.

She found it hard to let them in completely.(Y/n) was used to being closed off...with power came loneliness and the cold, brave face she had to put on to mask the unhappiness that she suffered when she was all alone. She went insane and began coping with overzealous fits of laughter that she experienced as she killed. But now she wasn't alone and she was far from insanity, however, she couldn't find it in herself to open up. She knew she had family she knew she did. But opening-up..even speaking of the pain and suffering she went through in hell was hard. She found to give in and tell of the deepest and the darkest fears that crept in the corners of her mind....would make her weak. 

"You don't have to be in charge anymore....you don't have to put on a brave face to scare others off..." Sam explained to her. 

She began relaxing in his hold and slowly nodded. She was willing to give-in...for him she was willing to give up power....she was willing to try.