Kaylee followed Dean to the Hunter's point and watched as werewolf 'Glen' chased down another hooker. Dean arrived and went to shoot 'Glen' but missed. 'Glen' ran at Dean and pounced on him. 'Glen' was about to tear Dean to shreds when Kaylee turned and jumped down behind 'Glen' before digging her claws into 'Glen's' neck and ripping his head straight off his shoulders. Dean shoved the body to the side before looking at Kaylee who was holding the severed head in her bloodied hands.
"It's okay now, Glen. It's over" Kaylee whispered sadly to the severed head before looking past him and directly at Dean, who flinched at the hatred in her eyes.
"Goodbye, Dean" Kaylee said bitterly making Dean's heart ache at the hatred in her voice. She grabbed Glen's body and disappeared with him, leaving Dean behind in the alleyway. Sam and Dean met up in the Impala and Dean filled Sam in on what Kaylee did as they sat outside of Madison's house in case she turned that night.
"Why do you think he turned Madison, instead of just killing her?" Dean said ignoring the glaring from Sam.
"I don't know. He kind of seemed to have a thing for her" Sam said through gritted teeth.
"Maybe his primal instinct did too. Maybe he was looking for a little hot breeding action" Dean said before Sam punched him in the face.
"Call Kaylee and beg for her forgiveness. Now" Sam snapped at him as Dean held his face.
"It's too late, she hates me now" Dean said simply.
"Can you blame her?" Sam asked spitefully before pulling out her phone and trying to call Kaylee but got no answer.
"Speaking of Madison. You liked her. Maybe…" Dean started to say trying to change the topic away from his very large and painful mistake that lost him Kaylee.
"Dean, she thought I was a stark raving lunatic" Sam said seriously.
"You saved her life" Dean countered.
"Yeah, but she doesn't know that" Sam countered back before Madison came and knocked on the car window.
"You know, for a stakeout... your car's a bit conspicuous. What are you still doing here?" Madison asked as Sam lowered his window.
"Honestly? Uh... We're pretty sure you're not gonna turn tonight... but we gotta be 100 percent. So, you know, we're lurking" Dean said offering a weak smile at the end unknown to any of them Kaylee was watching from a nearby tree.
"Look, I know this sounds crazy…" Sam started to say before Madison interrupted.
"Sure does. Well, if we're gonna wait it out... we might as well do it together" Madison said letting Dean and Sam into her apartment but before Sam went into the building he saw Kaylee watching. They locked eyes but when Sam blinked, she had disappeared.
"You were telling the truth, weren't you? About everything. What you did, it was to help me" Madison said softly.
"Yeah' Sam replied sadly.
"I did all those horrible things... when I turned" Madison said disgusted in herself.
"You didn't know" Sam offered truthfully, as Dean watched them stare at each other and it made him think about Kaylee. What he had lost because of his pig-headedness.
"So, when will we know for sure? Moonrise?" Madison asked.
"No, I don't think so. You turned middle of the night last night. I think we gotta hang in until sunup" Sam explained, wishing Kaylee was here so she could tell them for certain.
"Well, it looks like we got ourselves a few hours to kill. Poker, anyone?" Dean asked trying to break the silence and they played for hours and then stayed up the rest of the night until sunrise.
"Does-? Does this mean it worked?" Madison asked daring to hope as they watched the sunrise.
"Yeah, I think so" Sam said happily.
"Oh, God, thank you. Thank you so much" Madison said hugging Sam before Dean cleared his throat.
"You too, Dean. Thank you" Madison chuckled.
"Aw... don't mention it" Dean said before looking at Sam.
"Yeah. So, I'm just gonna head back to the hotel... and watch some pay-per-view or something" Dean said not so subtly before leaving the apartment.
"That was smooth" Madison chuckled.
"He means well" Sam stuttered.
"You mean, he thinks you're gonna get laid" Madison corrected.
"Look, I... I know I scared the crap out of you, all right? I mean, I tied you to a chair" Sam said seriously.
"That's right up there with me... scratching up your face" Madison added.
"There's just no way... we could go back, you know... before it happened" Sam said sadly.
"You're right. There's just no way" Madison said before they suddenly started kissing and stripping each other of their clothes.
…..
Dean sat in his hotel room flicking through the TV channels depressed before trying to call Kaylee again but getting her message bank.
"Kaylee… I… I'm sorry okay. I fucked up. I mean, I royally fucked up. It's no secret that I have trouble seeing… supernatural things as anything more than a monster but that's not how I see you! Not at all! And I know that doesn't make any sense! I know that okay, I'm just… I can't explain it. I see you and even though I know you are a werewolf… I don't see a monster or a killer… I see the woman I love, but I see Madison or Glen or even Kane, I can't think of them in any other way. I'm not trying to excuse what I did or said…I just… I'm sorry" Dean said into the phone, leaving a message for Kaylee as tears slide down his cheeks before suddenly someone was knocking wildly at the door. Dean wiped his eyes and opened it to reveal Sam.
"She turned" Sam said hurried.
"What?" Dean asked shocked.
"I couldn't grab her in time" Sam added sorrowfully.
"We'll find her, Sammy" Dean said grabbing his jacket and following Sam outside.
"I already called Bobby. He doesn't know anything. Except, he knew severing the bloodline wouldn't work. Most everyone says it's impossible to reverse it" Sam explained.
"How come she didn't turn when we were with her? You put her to bed, then she wolfed out? Maybe she's gotta be asleep to turn?" Dean asked as they walked down the stairs.
"Wouldn't it be awesome if we had someone who was connected to the werewolf world? Oh wait! We do!" Sam snapped before sighing.
"What does it matter? We gotta find some way to help her. Some legend we missed" Sam said worried.
"If there was, someone we know would've known. Kaylee would have known about it" Dean argued back.
"Well then, we have to look harder until we find something" Sam snapped.
"Sammy, I don't think we got a choice here anymore. I hate to say it... she's sweet, but part is…" Dean started to say.
"Evil? That's what they say about me, Dean. That's what they say about Kaylee. So, me and Kaylee, you won't kill... but her, you're just gonna blow away?" Sam snapped knowing that bringing Kaylee into it was a low blow for Dean but before Dean could snap back Sam's phone rang.
"Sam?" Madison asked scared.
"Madison. Where are you?" Sam asked worried.
"I don't- I don't- I don't know where I am" Madison stuttered.
"Well, do you see any street signs?" Sam asked desperately.
"Um... Yeah, yeah. Middlepoint" Maddison said looking at a nearby street sign.
"All right, all right. Hold on, Maddy. We're coming to get you. Just stay where you are" Sam said as they jumped into the Impala and drove to get her. They took her back to her hotel room and sat quietly in the kitchen.
"I don't remember anything. I probably killed someone last night. Didn't I?" Madison asked in shock.
"There's no way to know yet" Dean replied softly.
"Is there something else we can try to make it go away?" Madison asked.
"We'll find something. I mean, there's gotta be some answer, somewhere" Sam said desperately.
"That's not entirely true. Madison, you deserve to know. We've scoured every source. There's just no cure" Dean said honestly.
"Is...? Is he right?" Madison asked looking at Sam. Sam turned away with tears in his eyes.
"I mean, we could lock you up at night... but you'd bust out, and some night you will... someone else dies. I'm sorry, I am" Dean said honestly as Madison cried.
"So, I guess that's all there is to it, then" Madison said sighing.
"Stop it. Don't talk like that. We have a friend, she is like you. She can help" Sam said desperately.
"Sam, I don't wanna hurt anyone else. I don't wanna hurt you" Madison said picking up the gun and hanging it to Sam.
"I can't do it myself. I need you to help me. I'm a monster" Madison begged just as Kaylee walked through the door, her eyes never landing on Dean but she did spare Sam a quick look.
"You don't have to be. You might be able to survive of only animal hearts" Kaylee said walking over to Madison.
'Really?" Madison asked hopefully and Kaylee shrugged.
"Honestly, I don't know. It's works for me but I'm also a pureblood werewolf, not a regular one like yourself. But I have a family member, who is a regular werewolf, and he has been living in the forests for the past few months. When you turn, the animal in you hunts and kills the nearest prey they find, which is normally humans because of all the cities but if you live deep enough into the forest; it can be animals. Kane has done it for the past few turns. It hasn't killed him yet but we honestly don't know how effective it will be" Kaylee explained looking only at Madison, not at the two brothers.
"I… I don't know" Madison said softly.
"It's your only option; otherwise they are going to kill you. But it's your choice. I was born this way, you weren't. I understand if you choose to die rather than live as this… monster" Kaylee explained trying to keep the hurt and emotion out of her voice because she knew she was a monster and she was only ever pretending to be normal.
"I… I can give it a try" Madison said weakly and Kaylee nodded holding out her hand. She looked over to Dean and cocked her head to the side.
"Are you going to try and stop me, Dean?" Kaylee mocked spitting out the out 'try' and 'Dean'. Dean winced but looked at Kaylee desperate to show her how sorry he was. Kaylee's eyes softened slightly but only for a second before they hardened again before turning back to Madison.
"I'll take you to Kane, he is my brother. He will teach you what it means to be a werewolf. He is the only person I trust with this" Kaylee said taking a not so subtle, insult at Dean and Sam. Madison put a hand in Kaylee's before looking back at Sam.
"It's okay. You can trust her and Kane" Sam said nodding before looking at Kaylee, who was barely making eye contact with them.
"Thank you" Sam said honestly and Kaylee nodded to him before turning around and going to walk out the door with Madison.
"Kaylee, wait… please. I'll do anything to make it up to you" Dean begged, not caring Sam and Madison saw him being so vulnerable. Kaylee spun around and pinned Dean with a glare.
"Our relationship or whatever it was between us, is done. I won't be with someone who is so stubborn about killing every damn monster even if it is the same kind of thing I am" Kaylee snapped bitterly making Sam and Dean wince at her tone.
"But… Sam is still my family and you are his family. When you have another job; call me" Kaylee said looking at Sam before walking out of the room with Madison.
"Could have been worse" Sam said softly, placing a hand on Dean's shoulder in comfort.
"She didn't even acknowledge me as family anymore…" Dean said in a whisper to himself.
"She didn't say you weren't family either. She is hurting. Give her time" Sam offered as advice.
…..