"Thanks for taking this drive with me."

"It's not a problem," Dean smiled, lacing his fingers through hers and resting them on his knee as they sped down the lonely highway. "You seemed a little restless."

"I was. Staying in that musty motel room while you guys hunted that damn trapped spirit in the old meat packing plant..." Cailey trailed off, breeze from her open window blowing through her choppy blonde locks. She was always trying out new colors and at the moment was streaked with dark browns and reds.

"You did a lot to help, though. I'd say your research could put Sam to shame."

"I highly doubt that," she turned and pressed a kiss to his cheek before bringing her eyes back to the road. "But thank you. I wish I could have done more."

"Researching is good enough."

"For now."

"Cailey..."

"One of these days, I'm going on a hunt with you."

"Can't we take this one step at a time?" Dean questioned, sighing as he held back a frown. He didn't like discussing Cailey going on a hunt. He didn't want to think about it. The last thing he ever wanted was to have her get hurt, doing what he does. It was hard enough to let her know what he did for a living. She believed him, which caused him one Hell of a shock. As the months went on, he let her delve more into their lifestyle until finally bringing her along for the safe part of a hunt. She was a great researcher, he wasn't lying about that. He loved her too much. If she ever got hurt...

"You do have a point," Cailey finally spoke up after several moments of silence. "We'd have to wait for that."

"Say what?"

"We'd have to wait..." she trailed off, biting on her bottom lip. "Do you remember, around four months ago, when you came to visit for a weekend?"

"You mean the weekend of the bendiest, kinkiest, most random sex-filled weekend we've ever had?" Dean questioned, his green eyes lighting up. "Nope."

"Dean! Seriously!" she laughed.

"I do remember. What about it?"

"Well. We weren't exactly... careful... that weekend," her blue-gray eyes flitted to his for a moment, nervous, before looking away.

"Cailey, are you saying what I think you're saying?" The words fell from Dean's numb lips as his gaze fell downwards on her body.

"I know it wasn't what we planned, but..." she placed the hand that was wrapped around hers and placed it against her swelling abdomen that she hid behind sweatshirts and baggy t-shirts the whole time of the hunt. Dean's eyes grew wide when he felt a pressure push out towards his hand and his heart thumped loudly. "I'm pregnant."

"You mean, I'm going to be a daddy?"

"I know with all that's going on, it's not ideal, but--"

"Cailey, I felt it kick!"

"Yes, I've just started feeling it about a week ago," she chuckled, feeling his hand spread out against her abdomen and smiled when the baby kicked again, as if acknowledging its father. "...You're not mad?"

"Mad? Never!"

"Scared?"

"Aren't you?"

"Terrified! But... I think it'll all be okay. We have each other, and Sammy... Bobby... the baby will be protected. We'd be a family."

"A family," Dean smiled at the idea. He didn't know how it was all going to work out, but with Cailey, it always seemed like anything was possible. Well, besides her going on a hunt, that is. And thank God she hadn't come along to this currently finished one. "I like the sound of that."

"Really?" Cailey glanced over at him, tears of joy brimming in her eyes.

"Really," he reassured her, leaning over to brush his lips over hers, and bending down to kiss her abdomen. "Hi, baby. It's Daddy. Oh boy, is your life going to be interesting."

"You're already talking to my belly. So cute," she chuckled, running a hand through his locks as she drove down the darkening highway. Taillights on the side of the road slowly came into view, and she squinted slightly as Dean straightened up in his seat. "Look up ahead."

"What?"

"There's a car pulled over on the side of the road with their hazards on." Soon they were close enough to see it was a truck with steam pouring out of the opened hood. She slowed down and pulled up behind the vehicle, placing it in park. "Do you think it's safe?"

"Yeah..." Dean trailed off, handing her a small bottle of holy water as he grabbed his pistol to conceal under his jacket. "Just in case, put this in your pocket--"

As she put it snugly away in the front pocket of her sweatpants, her door was swung open and before Dean could react, she was outside. Screams filled Dean's head as he clamored out of the car, pistol in hand. He wasn't even able to get off a shot. A force pushed him back and he slammed into the windshield where he was stationed while Cailey was mere feet away.

"Dean!"

"Cailey!" He struggled and grunted against the demon's hold. "Let her go, you son of a bitch! It's me you want, not her!"

"Oh, quite the contrary, Dean. She is exactly what I want," the demon quipped with a sly smile that made Dean sick. The meat suit it had chosen was a middle aged man wearing overalls complete with a torn t-shirt.

"What the Hell are you talking about?"

"Oh, I think you already know," was all he got as a response while the demon trailed his hands down Cailey's sides and rested on her abdomen. Dean's heart leaped with fear and realization dawned on him. They knew. How?! She had just told him minutes before they caught sight of the truck. Obviously he hadn't kept Cailey as hidden as he thought he had, and now yet again he failed. "The question is, what shall we do about this little problem?"

"You're not going to do anything, because I'm going to kill you!" Dean hissed, struggling against the binds that held him.

"Wrong answer," he held out one hand and a force pushed his head against the windshield hard enough to crack the glass. Blood flowed from a wound in the back of his head. The demon turned to Cailey and cooed softly while cupping her cheek. "Don't worry, Love. It won't hurt that much as long as you don't fight it. This is all for the best, you know. Having another Winchester child out there is just too much for the world."

"Go to Hell," Cailey spat, turning her head away from his oily touch.

"Tsk, tsk, tsk. Been there, done that. You should already know that kind of response doesn't really affect us."

"I could care less."

"Human beings are so stubborn," he chuckled with a click of his tongue. "Stubborn yet ultimately fragile. Dean, you may want to say your goodbyes now."

"Go screw yourself--"

"Again with the wrong answers! Your father would not be proud of this moment," he interrupted Dean, his hand turned towards Cailey, palm out. Slowly, his fingers closed into a fist and pulled back towards his own body.

"Oh-oh, G-God..." Cailey stammered, looking down to see streamlets of blood course down the front of an old, raggy white Metallica t-shirt that Dean had given her. It had been one of his favorites and she wore it whenever she could. "D-D-Dean!"

"CAILEY! Leave her alone! Stop it!" Dean hollered, using every bit of strength to try and break free.

"Such dynamics. This is getting interesting," the demon smirked, clenching his fist tigher to bring forth more wounds.

"Oh m-my GOD!" Cailey screamed, her back arching in pain as the t-shirt turned crimson. A deep torrent of blood suddenly gushed from her abdomen and she screamed again. "Not o-our baby, PLEASE ST-STOP!"

"CAILEY! NO! YOU SON OF A BITCH, STOP IT! PLEASE!" Dean was demanding, damn near begging as he watched helplessly while Cailey was tortured. Tears of anguish poured down his cheeks as he was forced to watch her be tortured. It was so much like when he had been by Azazel while he possessed his father.

"This is meant to happen, there's nothing you can do--"

Finally, a car drove by with its brights on. It stopped and a figure climbed out. It was Sam. Before the demon could react, Sam had the Colt pulled out and a single shot rang through the air. A smoking bullet hole appeared in the middle of his forehead before he fell to the ground. Cailey was about to follow when Sam caught her. Finally, Dean was freed and he scrambled off the car.

"Cailey!"

"D-Dean... I'm s-s-sorry," Cailey trembled while in Sam's embrace, the blood continuing to pour from her many wounds.

"Don't be sorry, Babe, you did all that you could. None of this is your fault. You're going to be just fine, I promise," Dean soothed, running his hands through her sweaty locks. A cough wracked her entire body, blood running from the corners of her lips.

"Dean, this is bad," Sam murmured as he hefted Cailey up and walked towards the Impala.

"She's going to be fine."

"Dean--"

"Shut up, Sam! Just shut up and get us to the hospital."

This couldn't be happening. Hadn't he promised that she would always be protected from anything and everything that lurks in the dark shadows? Of course he did. But then again, it wouldn't be typical of Dean Winchester if he didn't fail someone he cared about.

"Dean..."

"I'm right here, Cailey. We're going to get you to a hospital. It's going to be alright. You and the baby will be alright," he ran a trembling hand through her damp locks. Bleeding... God, she was bleeding everywhere. He looked up and locked eyes with Sam through the rear view mirror, who pressed his foot harder on the gas. The scenery outside began to blur. How did it get to this? Holding a dying woman in his arms? A woman he had actually allowed himself to fall in love with; who was carrying his child. How...

"I'm cold," she whispered, shivering within his arms.

"Hold on," with slight difficulty, he was able to slip off his leather jacket while still keeping her close and placing it snugly around her broken body. "There we go."

"It's bad... isn't it?"

"No, it's not that bad. Once we get you to the hospital, you'll be fine. The baby will be fine," Dean could barely keep his emotions at bay as he tried to keep her mind off the seriousness of her injuries.

"Dean, don't lie to me."

"Cail, I'm not-"

"I understand," she took a deep, rattling breath and shuddered hard, arching against the pain. "God, it hurts so much..."

"Cailey? Cailey, c'mon, I need you to stay awake. Stay with me," Dean instructed, cupping her cheek and pressing a kiss to her clammy forehead. Her eyes fluttered open and she tried to smile, placing a bloody hand on the top of his.

"I love you."

"Don't say it like that."

"What?"

"Like you're not going to fight. Don't give up!"

"I'm trying. Something is pulling... pulling me away-"

"You weren't meant to die like this!"

"Don't know that."

"But we were supposed to have a baby together."

"I know, Dean. I know... I can feel... feel it dying... I'm sorry..."

"Please... don't leave me. Either of you," Dean begged, his voice breaking as her blood continued to soak through his leather jacket.

"Sweetie, don't have a choice," Cailey wiped the blood from her lips; her breathing became shallow. "Can... can you please... kiss me? One last time?"

"Cailey-"

"Dean. Please." The look in her eyes made the words dry up in his throat as he nodded. Leaning down, he pressed his lips against hers. Even now, they were as soft and smooth as when he first kissed her. It was bittersweet to the point where it felt like his heart would break into pieces as they pulled away.

"I love you," he whispered, kissing her once more, briefly.

"I know," she offered a small smile, a blood splattered arm reaching out to touch Sam's shoulder. "Sammy?"

"Yes, CC?" he placed his hand atop hers. Even though she couldn't see his face, she knew he was crying.

"Take care of... your brother... for me."

"Don't. Just... just hang on."

"I can't. It's... it's..." she trailed off, licking her lips. "Take care of him, Sammy. Promise me."

"CC, I-"

"Have to promise."

"Alright. I promise," he squeezed her hand for a moment before bringing it back to the steering wheel.

"We're going to get you to the hospital. They're going to patch you up, and then we'll go see Bobby. He'll know what to do," Dean replied as she turned to look at him. It took all he had not to break down in front of her. If she saw weakness... he'd lose her. He had too much loss in his life. He couldn't handle much more.

"Dean..." she sighed softly, her hand against his cheek once again. A cough shook her entire body and she tensed up with pain, her head turned away. When she faced him he could see blood had coated her lips. "It's okay."

"No. I shouldn't have told you. What Sammy and I did. It was too dangerous, and now I got you hurt-"

"It's okay. I'll take care of our baby."

"Cailey-"

"It's... okay..." she trailed off, smiling softly as her gray-blue eyes looked up into his green ones. Her breath flowed out slowly and the hand that was on his cheek fell down onto her chest. Dean watched anxiously, waiting for it to rise again.

"Cailey."

No response. Her once beautiful eyes, which now saw nothing, stayed open and vacant.

"Cailey!" he shook her gently, but enough to at least rouse her.

No response.

"No. No, no, no. NO!"

"What? What is it?!" Sam shouted from the front seat.

"Pull over. PULL OVER!" Dean shouted as he continued to shake the younger woman. Without hesitation, Sam veered the Impala onto the side of the road. Slamming it into park, he got out and ran to help his brother carry Cailey outside and onto the ground.

"Cailey... No... She... She's gone..." Sam whispered as he watched Dean hold her stiffening body.

"She's not gone!"

"Dean-"

"Sam, I swear to God, if you say that again, I'll kick your ass!" Dean shouted as tears poured down his cheeks. "She's too strong, she wouldn't-she couldn't-"

"Dean."

"No. Sammy, please. No..." Dean whimpered with a shake of his head as Sam came and wrapped an arm around his shaking shoulders. "She's not..."

"She is."

"Cailey," Dean began to sob, for once not caring that Sam saw any true emotion coming from him as he pulled Cailey up to cradle against his chest and buried his face in her locks.

"Dean, I'm sorry. I'm so, so sorry," Sam whispered against the side of Dean's head, tears forming in his hazel eyes and falling down his cheeks.

"No... No..." was all Dean could muster between sobs. First his mother. Then his father. He had almost lost his brother. Now he lost the woman he was going to raise a child with, and though he knew of the dangers others couldn't imagine, he wasn't scared of being a father. It actually thrilled him. No one had made him want that before her. Now, she was gone and it was more than Dean could take. Something built up in his chest and before he could stop it, a long, wounded cry escaped his trembling lips. Leaning down, he pressed them against Cailey's cold forehead as his tears fell into her locks. "Cailey..."