Dean x Reader

Synopsis: Prompt from Tumblr. Dean is captured by Demons, along with a woman(the reader). Being drawn to her instantly, he tries everything to keep her safe, only to face heartbreak later on. *Not a very happy story**

The prompt: He didn't even know her name, yet he felt sorry for her, for the pain she was going to live through. 

Three days. That's how long Dean had  been down in this hell hole. He knew he really wasn't in Hell, for there was no smell of brimstone, and he could just make out the light of the sun peaking through the boarded up window on the far side of the room he was being held in. 

This hunt had started out easy enough. He and Sam had driven in to town, checking into one of the shabby motels they usually inhabited. After questioning the local authority and the medical examiner, they knew exactly what they were dealing with, Demons. Then it came the matter of finding the Demon's hiding place. While Sam had been researching like crazy, Dean had needed a break. Leaving to find dinner for the two of them,  he never made it back to the motel. As he  climbed out of the Impala, something heavy hit the back of his head, knocking him to the ground, his body growing lax as he fell unconscious. 

Waking up, Dean found himself in this cold room, a cell of cement with one boarded up window. Chained to a heavy metal chair, his legs and arms both wrapped tightly with no give at all. Hours passed before his captors came, evil grins on their faces and a tool chest in their hands. 

"The famous Dean Winchester." The ring leader, a man he came to know as Dageus, said in a rough accent as he rubbed his hands together. "We are going to have so much fun together."

Their fun came in the form of torture. With knives, pliers, even a torch, they tortured Dean each day, to the point of unconsciousness. With blood pooling around him, his head would rest against the wall, but he refused to give them the satisfaction of his screams. Staying silent as they inflicted their pain, Dean's eyes would stare hatefully into their pitch black ones, letting them know he would kill them the second he became free. 

"You know your brother isn't coming to save you. It's just you and us now. And we have plenty of revenge to exact. All of our brothers and sisters you've killed or tortured for your own gain. It's time you felt what they did." Dageus threatened before slamming the knife down into Dean's thigh. Closing his eyes, Dean bit his lip so hard it bled, but still, he refused to make a sound. 

Frustrated, they left, finally leaving him to his own misery. Soon, the little sliver of sun left, leaving him in pitch black, and he wondered how much longer he would survive in here. He had faith in Sam, but he didn't want Sam risking his own life to save his. He had prayed to Cas, letting the Angel know he was alive, praying for him to help Sam find him, but Dean wasn't sure if Cas was even able to hear his prayers this time.

After the third day, Dean heard the door open, his mind fuzzy from lack of nutrition and blood. Blinking his blood crusted eyes open, he watched in horror as they brought in a beautiful woman, her body laying limply in their arms as they carried her to the set of chains on the wall across from his. "We brought you company." Dageus explained happily, as they tossed her to the ground before chaining her up. Her h/c hair was in tangles, her face pale with a vivid purple bruises forming on her jaw. Otherwise she was untouched, not yet having been attacked by the brutal Demons.

"Why do you keep doing this?" Dean muttered, still pulling hard on his restraints, wanting nothing more than to kill the Demons and rescue the poor innocent girl.

"Because Hell is in chaos, and we're bored. Happening upon you was just icing on the cake. And now you get to watch us tear this girl apart." Dageus goaded, his hand running through the girl's hair, and Dean wanted nothing more than to tear the Demon's hand off. "Soon." Dageus wickedly promised the girl, before locking the door behind him, leaving the two of you in pitch black darkness.

He wasn't sure how long he sat there, waiting for her to wake up, needing to stay calm for her. He didn't even know her name, yet he felt sorry for her, for the pain she was going to live through. For he knew they wouldn't go easy on her, that they would no doubt torture her to get to him. That thought killed Dean, and he hoped his brother would hurry up and arrive, rescuing them both.

What seemed like hours later, with the sun barely starting to shine through the slit in the window, he noticed the fact that she started to come to, her body shivering in the cold air of the room. He watched her carefully, knowing she might panic as soon as she came to, and he wanted to try and calm her down before she pulled too hard on her restraints and hurt herself. 

Dean didn't get the chance to help her like he wanted. As soon as he started to speak, hoping she would understand and calm down, Dageus was back, heading straight for her while his minions went to the hellish toy chest. "Finally." Dageus exclaimed, grabbing her hair and pulling her face up. With the lights on in the room, Dean could tell her eyes were a beautiful e/c shade, her pupils wide with terror. 

"No, you Son of a Bitch! Leave her alone!" Dean exclaimed, his wrists turning bloody and raw as he pulled against the chains holding him to the chair. 

"Finally. He speaks." Dageus remarked as he pulled the frightened woman to her feet. "I knew bringing in another person would break that tough exterior of yours."

"Fine. I'll speak. Just torture me, not her." Dean pleaded, and for a second he thought he had won. With a chuckle, Dageus reared back his fist, smashing it into the soft skin of her belly, and Dean cringed at the mangled cry that left her lips. 

"Damn it!" He yelled, wishing he could do something to help the poor nameless girl. Again and again Dageus brought his fist down, ignoring the knives held out to him as he pounded on the girl. Her cries turned to moans, and she tried to cover her body, trying to get away from the brutal attack but it was useless.

After what seemed like forever, Dageus left along with his henchmen, and Dean turned his attention back to the girl who lay panting on the ground, obviously in pain.

"Shh, I know it hurts." Dean tried calming her, not knowing what to do too much in a situation like this. "Don't worry. My brother is on the way. He'll be rescuing us soon."

"Your brother?" She muttered through her split lip, her voice as smooth as honey. "Why hasn't he come for you yet?"

"He's still trying to find out where I am. But he will come, I know it. And he will save the both of us." Dean promised the girl, who shivered as she curled into a ball on the ground. 

"I'm Dean." He informed her, trying to take her mind off of the pain she had to be going through. 

"Y/N." She replied softly, her head lulling back as her strength waned. 

"Beautiful name." Dean whispered, but she was already asleep and he sat there, his body sore and battered, but his heart a little lighter as he stared down at the strong beautiful woman in front of him.

________________________________________

The next day brought much of the same. Dageus was gleeful, positively cheerful that he now had two victim's to torture, moving back and forth, slicing and dicing both of you. It wasn't just the pain that was hard to deal with. The worst part for Dean were the games Dageus seemed to enjoy playing. Holding a knife to Y/N's neck as she pleaded, her eyes on him while Dageus promised to spare her if Dean begged.

Dean could count the number of times he begged on one hand, and they usually all pertained to his brother Sam. But with Y/N's beautiful eyes pleading with him, he couldn't help but beg to save her, to torture him instead. She held some sort of hold on him, and he would gladly take the pain to spare her.

Each and every time Dean begged, Dageus would take a step towards Dean, removing the knife from her neck. With a devious glint in his eyes, Dageus would nod, letting one of his minions take another knife to her, while Dageus slashed Dean at the same time.

Soon the two of you were covered in blood, your bodies weary and beyond sore. Pausing for a break, Dageus left the room, promising to return with new toys to try out. Hearing sobbing coming from Y/N, Dean felt useless, unable to do the one thing he was good at. Saving the damsel in distress, killing the monsters. Yet here he was, watching as Y/N lay bleeding and broken on the ground, the Monsters running wicked and free. It was infuriating, and Dean banged his head against the wall, needing to find a way to save her, and himself, before Dageus could do anymore danger.

"Dean, please. I need you to do something for me. If you make it out of here and I don't." She pleaded through blue tinged lips. 

"No, we are not going to do this!" Dean heard himself yelling her way. "We are both going to get out of here, I promise you."

"But I'm so cold." She chattered. "And I feel so weak, so tired."

"Y/N, you can't sleep." Dean ordered, knowing they had bashed her head at least twice and he was worried about a concussion. 

"So tired." She whispered again, and Dean cursed as her eyelids closed and her body relaxed on the floor.

He was weary too, his body much weaker than he would care to admit. His eyes grew heavy and leaning his head back, he kept whispering over and over that help would come, that he would get Y/N out of this mess if it was the last thing he did.

Grunts and screams filled his ears, waking him up for his exhausted slumber, his neck popping in pain as he straightened his head. Glancing down at Y/N, his heart stopped for a moment when he noticed she was still out cold even with the loud noise coming from outside their door. It was when he noticed the slight rise of her chest he let himself relax, waiting to see what was happening.

More screams filled the silence before the door was shoved open and a bloody and sweaty Sam filled the doorway, his chest heaving from exertion. "Dean!" He exclaimed, rushing forward but a quick shake of Dean's head had him stopping in his tracks.

"Her first. Save her." Dean prodded, pointing his head over to the unconscious Y/N laying on the ground. Nodding quickly, Sam moved, kneeling down and undoing the chains with the keys he had taken from Dageus. Leaving her laying on the ground, Sam came over, unlocking the chains around Dean's ankles and wrists. Without the support of the chains holding him up, Dean almost fell, if it wasn't for Sam reaching out and catching him. 

Just then Cas came in, a bloody Angel Blade in his hand as he surveyed the small room. "They are all taken care of." He announced.

Leaning down, Sam helped Dean to his feet, moving to leave the room. "No, not until she's taken care of." Dean pleaded, and Cas strode over, leaning down and picking her up gingerly in his arms. Making sure Cas went first, Dean limped along, using Sam to support most of his weight.

"Took you guys long enough." Dean muttered as Cas pushed the door open, the bright sunlight blinding to Dean's eyes.

"They were well hidden. It was only when Cas showed up that we could find out where they had taken you." Sam explained, as the Impala came into sight. 

"Thank god." Dean exclaimed, running his hand along the smooth exterior of the car. "I was afraid I might never see you again Baby."

Sliding stiffly into the backseat, Dean motioned for Cas to slide Y/N in with him. Letting her head rest against his lap, Dean stared down at her, seeing her truly for the first time. She was beautiful, even with the gashes and marks along her pale skin. Skin that was probably vibrant and beautiful was pale from blood loss, dirty and covered in blood. Her eyelashes were dark and long against her cheeks, but he couldn't wait until she stared up at him with her e/c eyes once again. 

"Dean, maybe we should drop her off at the local hospital." Sam suggested as he drove away.

"No. She stays with us. Cas can heal her." Dean ordered, and Cas looked into the backseat, studying Dean carefully.

"Dean, I am still weak. I can heal only one of you right now. She needs to be dropped off at the hospital." He explained, but Dean wasn't having any of it. He needed to know that she was safe, and cared for, and he didn't trust the hospital. He trusted Cas.

"Heal her. I will live." Dean argued, and the ride turned silent, neither man wanting to argue with Dean when he was that set in his decision.

It was about a thirty minute ride to the motel, and a couple of times Dean felt himself start to nod off, only to wake up to make sure he didn't startle Y/N. During the entire ride she didn't move, and Dean was starting to worry that they may be too late. As soon as they arrived, Dean made Cas carry her inside, while he hobbled along behind. 

Almost falling into the first chair he came across, Dean waited impatiently for Cas to begin. "Please Cas. She's been unconscious for hours now."

"Dean, please reconsider. You are hurt, you need my help." Cas tried arguing, but Dean would have none of it.

"No. Heal her." Dean ordered once again, and with a startled look to Sam, Cas leaned down, pressing two fingers to Y/N's cheek. As he worked, Sam came to stand next to his brother, his hand a comfort on Dean's shoulder. 

"Dean, why is she so important to you?" Sam asked quietly as the bruises and cuts began to fade away, her skin returning to her natural shade. 

"I don't know." Dean admitted. "As soon as they brought her in, I felt drawn to her. It killed me that I wasn't able to protect her, that I had to watch her suffer at the hands of those Demons."

"Come, let's try to clean you up." Sam suggested, leading a weary Dean into the bathroom. As Sam worked on stitching Dean up, Dean made sure he could see the beds, wanting to be there when she awoke. 

Much later, after his cuts had been clean and stitched, Dean lounged on the bed, staying close to her side, waiting for her to wake. Sam and Cas had left, going back to burn the building, wanting to make sure nothing was left for the Demons to return. Dean continued to watch her sleep, wanting nothing more than to run his hand down her smooth cheek, to learn everything about her. 

It was only seconds later he noticed her eyelids fluttering, as she slowly came to. He watched as her gaze fluttered around the room before landing on Dean. "Dean?" She whispered, her voice still smooth and sweet, music to his ears.

"We're free. The bad guys are dead, and we are safe." Dean assured her, helping her to a sitting position, wincing as the movement jarred his sore body.

"This isn't a dream? We're truly safe?" She muttered, before a smile broke out on her face. "But my body. It doesn't hurt anymore. The cuts are gone!"

"I have a friend who helped." Dean answered staying vague so he didn't upset her anymore than needed.

"Thank you so much." She exclaimed, before frowning. "But Dean, I need your help."

Grasping her hand, Dean nodded, ready to give her anything she asked for. He wasn't expecting her next words however, and Dean felt his whole world shatter in an instant.

"My husband. He has to be so worried. Can you take me to him? I feel horrible asking because you've done so much, but I need to see him!"

In an instant Dean felt himself doing what he did best. Shutting himself back in, putting on a fake smile, pretending everything was okay. Even though inside he was shouting at himself for being so stupid. For thinking that for once something would go his way, that maybe he could get the girl. "Of course. Let's go."

Standing up on shaky legs, Dean waited for her to climb out of bed, giving her his arm for support. Making their way outside, Dean was grateful Sam and Cas had taken Cas' car, leaving the Impala behind. Pulling the spare key from the fender, Dean started the car, his face a mask as he pulled out of the parking lot, following her directions towards the middle of town. 

Glancing over occasionally, he watched as a tirade of emotions crossed her face. Worry and relief, hope that her family was still okay. He wished for a moment that those emotions were for him, that she was rushing to return home to him. It was foolish, but he still felt drawn to her, wishing they could have met under different circumstances.

The drive wasn't long enough, and soon Dean was pulling up to a nice suburban home. Parking outside, Dean said quietly and calmly. "There you go, home at last." Keeping his gaze on his hands, and not on the beautiful woman next to him, knowing if he glanced into her sparkling eyes, he might admit to things he would regret later.

"Thank you Dean." She told him softly, reaching over and grasping his hand with hers. Her lips ghosted across his cheek, before she slid out of the car, rushing up the sidewalk throwing open the front door to her house. Forcing himself to watch, Dean saw her through the front window, a tall, handsome man with dark hair throwing his arms around her, holding her tight. Wishing it was him, Dean tortured himself more, watching as she stood on her tiptoes, pressing her lips to her husbands, threading her fingers through his hair. 

With a groan, Dean started the Impala, gunning it down the road, and out of the subdivision. Slamming his hand against the steering wheel, he finally allowed his mask to break, letting a single tear slip down his cheek at the thought of what could have been.

By the time he returned to the motel room, Sam and Cas were back, waiting for him with questioning gazes. "She's home now." Dean announced, walking straight over to his bag, pulling out a bottle of whiskey. Downing a big gulp, Dean let the warm liquid burn down his throat, the burning a welcome relief to the pain his heart was filling.

"Dean, what happened?" Sam asked, noticing how quiet and reserved his brother was being. Even more so than normal.

Dean downed another shot before answering his brother. "She woke up, needing to get back to her husband, so I took her. That's it."

Laying down on the bed, Dean took another sip, wanting nothing more than for the alcohol to erase the memories of the e/c eyed girl that had easily stolen into his life before leaving him with a gaping hole in his heart.