ULTIMATE DISCLAIMER: Every content, character, plot etc. that anyone is able to recognize as other's property is NOT mine. I have no intention to get into any trouble involving law and money.

ULTIMATE WARNING: So far most of my stories are turning out to be SLASH and MPREG. So they may contain mature, Male/Male Relationship and not so graphic sex scenes between two men. If you can't stand these or don't want to read them, please leave this story behind!

AU, OOC. SLASH, if you look for it! :D And as you guessed I'm sure, CrossDress!Harry!

Hey, guys! I got inspired with the plotline of Whatever It Takes and I had one or two requests for Dean's and Harry's plan. I got kinda enthusiastic, so this turned out pretty long. And also I count this as prequel, but maybe this makes much more sense if you read Whatever It Takes first.

So, have fun! And hope you'll like it!

What's The Plan?

Dean was hidden in the darkest spot of the room, observing the scene in front of him. He was afraid for his brother. He was doubting everything from the moment they'd thought it out…

Dean shot up in his bed, waking abruptly from his sleep. The ongoing screams were slowly replaced by the heavy silence in the room and the darkness chased the bright red flames away from his mind. He shakily slid up to the headboard and wiped the sweat from his face. He began breathing deeply to even his inhales and exhales that speeded up from the terror and adrenaline his dream let loose in his veins.

It was Hell. Literally. Almost a year went by since he got out of that awful place and his nights were still plagued by nightmares of his failure. How he had given in to the temptation… But he was hurting so much… Dean felt his throat tighten from the all-too-familiar pressure of guilt rising in him. How could he have done such a thing? He swore that he would help people in need and now he had to suffer from the pictures of him hurting those souls down there…

Before he could have a full breakdown, though, he gathered his will to push his tears back down. When he deemed himself ready, he looked up hoping to find some comfort. He had to see his only reason to live if he wanted to survive the night… His only purpose of going through all that pain the hunting lifestyle brought him day after day, dumping it onto his hunched, too damn tired shoulders… He had to see the person, who usually slept in the next bed, guarded by his presence…

And who was currently nowhere to be seen.

"Sam?" he called out, still shaky from his nightly terrors. He was greeted with a silence so deep he thought his eardrums would pop. He felt a slight panic grip his heart tightly: his brother was missing! But as his eyes adjusted to the dark, he noticed the messy bed. He sighed dejectedly. He noticed his brother's strange behavior: short-tempered outbursts, nervous ticks like chewing on his nails and glassy gaze flitting all over the room like he was expecting something to jump out and kill him. His brother was going through withdrawal, again. So, now he had an idea where his brother could be and it wasn't a nice idea.

He felt an urge rise in his heart. He needed some comfort now, he wasn't afraid to admit it. Just a voice that kept him grounded until he got through the aftershocks of his memories. With that craving he snatched his phone up from the nightstand and hit speed dial 3. 1 was Sam, 2 was Bobby and Dean knew he couldn't go to them for help. So, 3 remained; the person only he had contact with.

"Hello?" a sleepy voice answered the call. Dean knew that despite the late hour, his friend was already wide awake and alert.

"Hey" Dean spoke, cursing his voice betraying him by trembling and cracking up.

"I'm coming" came the only answer before the dial tone. By the time Dean threw his phone back to the nightstand, a soft pop resounded in the darkness and a pair of small arms wrapped around Dean's shaking body, wordlessly pulling the man into a hug. Dean let out a long breath at that and a hand rubbed his back comfortingly.

"Shh, it's okay" his friend spoke in a whisper. "I'm here, you're okay…"

Dean took a deep soothing breath then as his body stilled and relaxed, he pulled away. One arm still stayed around his shoulders, the man glad for that banister between him and the deep, dark pit of his guilt. A minute later light flooded the room with a click as the bedside lamp turned on.

"Thanks" Dean said, feeling like himself at last and looked up at his friend, hiding a disapproving wince.

It was a while ago that he'd met Harry Potter on a hunt, being saved by the young man from a vampire's nest. They'd run into each other a few times after that and Dean could get to know his new acquaintance. As time went by they'd become friends and Harry had trusted him enough to give him his all-time phone number, for any kind of emergency. During their meetings he found out that Harry's been hiding from his people in England, because they'd wanted him executed in fear of taking over the world. The young man had such powers that not even the ancients of the wizarding world understood them.

At first Dean hadn't believed him, thinking he was crazy about the whole wand-waving, potion-making, broom-flying variety of magic, but after a while he'd just gotten used to it. Every meeting they'd had so far always started in an interesting way: since Harry was hiding, he had to alter his appearance to decrease the chance of the wizards finding him. Dean had already seen him with every possible hair and eye color, a couple of times as a goth and once in hip-hop clothing. That one time he'd laughed so hard, he'd actually fell onto his ass because of it. It'd felt good for him since that was the first meeting after he'd returned from Hell. He didn't have any grudge to the rapper-attire-wearing people, but his friend had looked extremely ridiculous like that.

This time the young man wasn't faring better, it was even the worst he had seen him in. Harry made his hair grow out and it was pulled into a ponytail. The black tresses were lightened to a greyer color and he had the beginnings of a beard on his chin. His clothes were worn and dirty: he looked just like a homeless guy stumbling in from the street.

"Better?" Harry asked worriedly. Despite his scruffy outlook, his voice and touch was gentle and soothing, just what Dean needed for his frazzled nerves. He nodded and sent a grateful smile to his friend. "Where's Sam? He should be here, not me" Harry spoke disapprovingly. He had the luck to meet the younger Winchester before the whole Hell-fiasco, and ever since that he got angrier and angrier with him because of him neglecting his own brother this way.

"I don't know" Dean shrugged with a bit of disappointment. "He wasn't here when I woke up." Catching a glimpse of Harry's fury he quickly shook his head. "Don't!"

Harry huffed in annoyance but he'd already learnt to shut his mouth here. He knew Dean didn't need to hear his griping right now about the issue. Seeing that Dean stopped trembling and was much calmer, Harry let go of his shoulders but stayed in his place on the edge of the bed, next to the man.

"You think…" Dean started after a brief silence, much to Harry's surprise, "he's with that demon again?"

"What makes you say that?" Harry asked quietly.

"The signs" Dean's reply made Harry tense up. The man already told him about Sam's addiction, so he knew what he was referring to.

"Alright, that's it!" he exclaimed, although it was still silent compared to the quiet of the room. "We can't just sit on our arse 24/7, watching him destroy himself with that bloody addiction!" Dean knew his friend was angry, when he heard the much more accentuated British accent come out of Harry's mouth. He always had it, but with the years it smoothed in between the two accents.

"But what can we do?" Dean asked. "He's with that bitch again! He will get his fix of poison! He's probably chugging it right now, as we talk. No matter what we say, Ruby will always get him back on her side." At the sneer of the demon's name, Harry tensed up and his eyes widened in fear.

"Her name is Ruby?" he breathed terrified. Dean nodded and felt unease settle onto his stomach at the audible gulp coming from Harry.

"What did you do?" he asked, a bad feeling surrounding him.

"I didn't know it was her" Harry spoke quickly, tripping over his words as he hurried to defend himself. "I didn't even know what her name was, it was just a demon and I… killed her."

"What?" Dean cried out in shock.

"It was a mistake…" Harry's protest died down from Dean's hearty laugh, which was slightly on the verge of hysteria.

"I can't believe it" Dean panted as he calmed down. "I wanted to hunt her down and make her pay and you kill her by accident." Dean pulled his sheepish-looking friend into a one-armed hug. "Oh, if I didn't know you…" Suddenly a thought struck into him, halting him. "Then where's Sam?"

Harry's head snapped to the door at that then he jumped up from the bed.

"I have an idea how we could help Sam" he rushed out as he turned off the lamp. "He's coming now, though. Come out and meet me after he fell asleep!"

Dean nodded, knowing his friend would see it and quickly laid back down under the covers, ready to feign sleep. A hand caressed his hair comfortingly then just as a pop resounded in the room again, the door opened.

Dean had his eye half-closed, as he listened to his brother. Sam closed the door quietly and staggered over to the beds. If he hadn't known better, he would've thought his brother was drunk. As Sam stumbled to his bed, Dean quickly shut his eyes fully. He felt a terribly shaking hand rest on his head for a moment and heard a whimper.

"I'm so sorry" Sam choked out breathlessly. After that a soft thump indicated that Sam fell into his bed. After long minutes of fidgeting, the younger man let out a strangled sob then got up and stumbled into the bathroom. As the door closed, Dean sat up, knowing that Sam would be in there for a long time, wallowing in his misery. With that Dean got his boots, jeans and jacket on and left the room with an aching heart and a new determination in his mind. As he reached Harry at the other end of the parking lot, he spoke up firmly:

"What's the plan?"

"Are you fuckin' serious?"

The shout was blown away by the wind that breezed through the parking lot. Harry just stood there with his arms crossed and his head bowed in a slight shame, as Dean snapped at him.

"He's just barely getting through one addiction, now you want to push him into another?" Dean shouted, not caring that he was practically in his friend's face as he did so.

"If you have any better ideas…" Harry shrugged indifferently.

"There has to be something else we can do!" Dean cried out, almost begged to his friend.

"Look, the other option is detox" Harry snapped in anxiousness. "And that's going oh so well…" his words were cut off as Dean grabbed the collar of his jacket.

"If you don't want me to smack that smart-ass mouth of yours, you shut it right now!" Dean snarled, but Harry just stared back at him with a challenging look. After a long minute, Dean let his friend go and began pacing in front of him.

"Look" Harry spoke as calmly as he could. "I'm worried about Sam, too. I want him to be better, just like you. But I can't see any other options here. And this does him more good than harm…"

"Giving him your blood is gonna do good for him?" Dean snapped back at him. "What makes you so sure about that?"

"My blood can counteract the demon blood Sam consumed so far" Harry explained. "If he gets enough, the taint will be purged from his system."

"And you think Sam wouldn't notice if somehow his powers just disappeared?"

"No, because they won't" Dean looked stunned by that answer, so Harry elaborated. "He'll still have his powers, thanks to the magic in my blood, but it won't affect him in any harmful way. He won't stray towards the darkside."

"How can you be so sure?" Dean asked disbelievingly. "Wizards have gone darkside as far as I know."

"If I activate the magic in the blood with the right spell, he won't."

Dean continued his pacing to think things through. He already saw the outcome for the worst in his mind: Sam killing Harry for his blood, going on a rampage with his newfound powers…

"He won't" Harry interrupted his thoughts firmly.

"Can you promise me that this won't have consequences?" Dean asked, desperate to know. "Like another addiction?" Harry's silence was enough answer for him. Without a word he turned around and began walking back to their room, flat out refusing to listen to and participate in this plan. However, as he walked into the room with Harry in tow, he was greeted with rhythmic bangs against a counter and heart-wrenching sobs coming from the bathroom. He felt a tear slide down his cheek and as he turned back to Harry, he saw the young man silently sobbing from the suffering they had to witness. He drew Harry back into his arms and whispered his consent into his ear, along with the details Harry needed to execute his plan.

The next day Dean acted like nothing has happened last night. He was breaking apart bit by bit, as he watched his brother's fatigue. The skin around his hazel eyes was swollen from crying and purple from the lack of sleep, while red blood vessels decorated the whiteness around his irises. His tanned skin was pale and he looked like someone with cancer in the last stadium: skinny, tired and in constant pain. Dean decided to ignore the small helpless whimpers behind his back for his brother's sake, but it took a lot of willpower to do so. It didn't mean, though, that he wouldn't help Sam in any way he could.

By afternoon Dean was exhausted from staying by Sam's side during his nausea and sickness in the bathroom. The younger Winchester was out again, probably looking for Ruby for his late fix. Dean leaned back on his bed and tried to suppress the urge to mourn his once lively brother, trying to keep his spirit up by the plan they were getting ready to execute with Harry.

Just as he was getting in the mood of going through with it, he heard a knock on the door. He stood up with a groan and opened the door cautiously. The person outside was standing with their back towards him, but what he saw filled him with blind rage and extreme confusion.

Dean was greeted by the ocean of ebony hair, the waves falling down the lean back, covering the black leather jacket. The high-heeled boots were covered mostly by the black jeans, and as the person had a hand on a bare hipbone, Dean saw the hem of a black tank-top.

"You" Dean growled angrily. However, his mind supplied helpfully: Ruby was dead! Harry killed him! Before he could do anything, though, the person turned around, giving him a hell of a shock!

"Me" Harry answered, smirking in victory. Stepping closer to the entrance door, it opened and Dean stepped back to give him space to enter. The man watched his friend with wide eyes and an open mouth, as Harry walked in with that all-too-annoying strut he saw from Ruby. Dean startled when a dark backpack landed on the floor next to a chair, and he closed the door as Harry turned towards him.

Dean looked his friend over thoroughly. Now that Harry didn't have so much layers of clothing on, he could see the shape of his body perfectly. The young man shaved himself – 'Finally' he thought – and put a little eyeliner onto himself. He even fixed his eyebrows to give them a feminine curl! In Dean's opinion, only Harry's emerald eyes would give him away that he was not Ruby.

"How much did you alter yourself?" he asked still in a little shock. Harry blushed and looked away.

"Nothing drastic" he muttered self-consciously. "Only my hair, my clothes and the make-up."

"You mean to tell me" Dean started "that you…"

"More feminine than usual?" Harry finished for the man, when he trailed off uncertainly. "Yes, I am. But I had to hide from the wizards."

"You're… just fucking gorgeous" Dean exclaimed involuntarily. Harry laughed timidly and looked down at his hands shyly. Dean then noticed the fake nails on the young man's fingers. "Wow…" he cleared his throat and steered his mind away from the gutter. "So, you found it?" Harry fished the cell phone out of his backpack and held it up.

"I'll be back later tonight" Harry spoke, his tone full-on business. Dean nodded and watched Harry shoulder his backpack and walk out the door, disappearing from sight just before the door closed.

It was dark outside when Dean woke up to a whimper. He knew Sam was still not sleeping, but he knew that the kid tried to keep quiet, thinking he was having a nightmare-free sleep. 'If only you knew, little brother…' he thought sadly. There was another strangled sob from the other bed that Sam tried to muffle with his pillow then the boy stood up and staggered into the bathroom, like always.

Dean got up as he heard a soft pop from the kitchen area. As he walked there, he noticed Harry in a dark corner watching the bathroom door intently. Dean tugged the young man in for a calming hug, knowing that they needed to act cool to sell this and fool Sam. They stayed that way, Dean doing most of the comforting. He knew why this was hurting his friend this much, but he could only offer so much to him. It wasn't him Harry needed.

They were startled out of their comforting by the buzzing coming from Harry's backpack. Harry took the phone out of it and just watched the screen lighting up with Sam's name in the middle. Soon the buzzing stopped and they heard small noises come out of the bathroom, strengthening once into a snarl. When that died away, Harry dialed the voicemail of the phone. It had one message on it; they both heard it clearly:

'Ruby…' Sam choked out. 'I need… need it… Please, get the fuck here, right the fuck now!' He lowered his voice from the snarl. 'Bring me… Blood… Want blood… Please…'

They knew that it was time. Soon Sam stumbled out of the bathroom and sat down on his bed, pulling his knees up to his chest. Harry took a deep breath as he got ready for his part then quietly snuck closer…

With a sigh, Dean retracted his thoughts to the execution of the plan.

'Whatever it takes…'

The End

So, how did you like it? I'm planning a sequel for these. What do you say? See you!