Summary: After an embarrassing incident at a motel following a hunt, it has become apparent that Jack does not know the facts of life. Sam, Dean and Castiel take turns giving Jack the "the talk". Hilarity ensues, plus some drama. Brotherly/family/friendship fic, no pairings.

Warnings: Some description of suggestive sexual acts, nothing graphic. Coarse language/cursing.

Disclaimer: I do not own Supernatural.


Chapter one: The incident

They were all exhausted. It had been one hunt after another. But their latest escapade had gone especially badly. Dean was driving them all back to the bunker. Sam sat stiffly beside Dean, while Castiel and Jack occupied the back passenger seats.

The impala smelt of dirt and the unmistakable smell of body odour that came with the grueling sort hunt they had all just experienced.

Sleep deprivation and semi starvation always put Dean in a terrible mood, he scowled deeply and held the wheel of the impala in almost a choke hold. "Bloody witch". He muttered under his breath. "I hate witches". Dean said for what could have easily been the twentieth time in one hour.

Sam sighed silently and pointedly stared out the window, trying to find a comfortable position. But each time he moved, his body seemed to make him aware of a new bruise.

Jack held in a groan when he realized they were still more than four hours away from home.

Sam shifted again, this only seemed to irritate Dean even more.

"Why do you keep shifting in your seat!?" Dean turned to glare at his brother. "Do you need the potty?" He asked mockingly.

Sam glowered back at him weakly. "Just drive".

"What do you think I've been doing for the past hour and a half?!" Dean shot back.

"Then let me drive." Sam said offered tiredly.

Dean looked astounded, as though he couldn't believe Sam had even suggested driving his 'baby', but before he could reply, Castiel spoke up.

"Dean, you're being a bitch." The angel stated simply.

"What was that?!" Dean viciously snapped his head back to glare at Castiel.

"I said you're being a bitch." He repeated. "Sam keeps shifting in his seat because he is hurting from his injuries."

"I'm fine Castiel." Sam asserted quickly.

"What injuries?" Dean demanded looking at his brother, he still sounded angry but there was also unmistakable concern in his voice.

"You would not be in pain if you would only let me heal you." Castiel said in an accusing voice.

"I don't need healing, these are only bruises." Sam said tersely.

Those words sparked a shouting match between Sam, Dean and Castiel.

Jack knew Sam was refusing to be healed by Castiel because he felt guilty for the life they couldn't save on their last hunt. Sam had come up dry in his research, but when he did eventually have a breakthrough, someone had already been killed by then. It wasn't Sam's fault, Jack knew that, everyone else knew that, Sam should also know that.

But Jack also knew to keep out of this conversation or rather argument. He had nothing useful to say, and even if he did, he knew if he opened his mouth as well, it would only add fuel to the fire.

After a few minutes, things had simmered down and Dean was back to muttering about witches again.

Jack hoped that would be the end of it, but Castiel spoke again.

"Sam…" He started in a slow and deadly serious tone.

But Sam was having none of it "Look at you!" Sam twisted his body to face Castiel, he winced as his body protested to the sudden movement. "You've been healing us continuously for the past week." Sam looked at the angel sympathetically. "You look haggard."

Castiel frowned thoughtfully. But before he could reply Jack interjected not wanting for there to be another verbal contest.

"We're all tired." He said, carefully pronouncing each syllable.

Without turning his head, Dean glanced at the youngest member of their troupe through the mirror. Jack sat in the back passenger seat looking like a deflated sausage dog.

"Yes, we are." Castiel admitted.

Dean stared at the road ahead for a few minutes, his brows knitted together in a light frown.

"Okay, how about we find a motel? Crash there for the night and head back to the bunker in the morning." Dean stated, it wasn't really a question and no one disagreed.

Castiel made a non-committal sound, not even bothering to hide the fact that he was sulking.

"Sounds good". Jack quipped up with enthusiasm he was definitely not feeling, he just wanted something positive to say.

Sam used his phone to look up the nearest motel, which turned out to be a good forty minute ride away.

Jack couldn't decide if the silence that filled the car was awkward or welcome. He desperately thought of something to say but Sam beat him to it.

"I tripped." Sam said finally.

"What?" Dean asked roughly.

"I tripped in the garden." Sam sighed at the blank look on his brother's face. "I was in the garden, I could see you and Castiel fighting the witch in the kitchen through the back window."

Dean looked at him puzzled. "And?"

"What happened?" Castiel asked softly.

"I just told you." Sam sighed exasperatedly, not looking at anyone. "I tripped. I made a run for the back door and I tripped over the garden hose and fell onto a bunch of ceramic planters."

"What?" Castiel sounded confused.

"That's why I don't want to be healed by you Castiel." Sam said quietly, but the angel heard him. "I was careless and made a stupid mistake. You shouldn't have to exhaust yourself for my clumsiness."

"Sam, still…" The angel started, looking as concerned as ever.

Sam risked a glance up at his brother. He saw Dean's frown slowly morph into a half grin. "Wait, wait, wait. Let me get this straight, you got beaten up by a bunch of plant pots?!"

"I wasn't beaten up Dean!" Sam protested, his ears turning pink. "Didn't you hear what I just said?"

"Dude that's priceless!" The amusement was clear in this voice.

Dean was openly smiling now, he looked through his front mirror at Jack, the young man looked both worried and confused. And that serious expression was what set Dean off, he burst out laughing. Sam started slowly, but soon he was almost doubled over with laughter.

Jack exchanged a look with Castiel that said the Winchester brothers have gone mad.

"It hurts to laugh." Sam said breathlessly. "Stop it Dean."

"You deserve it!" Dean shot back. "Oh man, I'm never gonna let you live this down."

"Lighten up Jack!" Dean shouted jovially, all traces of exhaustion gone from his voice.

Jack jumped up at suddenly being called out, he honestly didn't understand exactly what was so funny, but he offered a small genuine smile nonetheless. To see his brothers happy was enough to put him in a good mood.


They checked into the motel a little after 11pm. It was cheap and looked clean enough, except you couldn't quite shake the feeling that everything looked like it would be sticky.

There were eight guest rooms in total, four on the left side and four on the right side. The left and right side were connected by a large communal bathroom in the center, giving the building a U-shaped layout.

The manager had been less than happy to check in four guys that looked like something a cat had spit up, he'd clearly been woken up and so was in a terrible mood. He made his displeasure known, as he informed the group that they only had a couple of two bedroom rooms left, so Sam and Dean paired up, leaving Castiel and Jack to share the adjacent room.

"There's leftover food in the communal kitchen if you want." The manager said pointing vaguely to a room at the end of the hallway.

He paused again to take in the unkempt appearance of the men before him again and scowled in distaste. "There better not be any trouble, no funny business." He said in warning.

"Do you anticipate trouble?" Castiel asked out aloud in the direction of the manager.

"Of course not! Err…thank you for the food." Sam called out hurriedly. Dean rolled his eyes at his brother.

"Go shower, you smell." The manager replied grumpily. "But don't use up all the hot water." He called out as he dragged his feet to the managerial suite.

Castiel simply raised an eyebrow at the man then sniffed his arm pits. Jack did the same.

Sam shook his head disapprovingly at the three others.


Presently the four of them were gathered in Sam and Dean's room playing cards and enjoying greasy chips, hard sticks of garlic bread and semi-warm cheesy ravioli that Dean hadn't heated up properly in the microwave. It was all that was left in the kitchen.

After three bites Sam decided he couldn't have anymore. "Eugh. I can't eat this." He pulled a disgusted face, promptly dropping his chips. "I'm gonna head to the showers."

Sam got up and picked up the complementary towel that had come with the room. He narrowed his eyes at it suspiciously. "Hopefully the bathroom is finally free". Sam muttered to himself. He exited the room and proceeded down the dimly lit corridor to the communal bathroom at the center of the hallway.

"Your loss" Dean said distractedly, already reaching for his brother's discarded chips.

Jack lay down on top of one of the beds and listened to Dean and Castiel. He felt tired, but sleep continued to elude him.

"I should probably head to my own room." Jack said to himself. "And I need to shower." He unintentionally let out of loud sigh.

"Can't sleep?" Dean asked, not looking up from his cards.

"Yeah." Jack admitted. He considered joining their card game, but he had already witnessed Dean cheat Castiel out of $70, and he himself didn't wish to become the next prey.

"You should not have napped in the car." Castiel added, he looked so serious, as though the cards in his hand held the meaning of life itself.

Dean smiled slyly as he proceeded to take another $20 from Castiel.

"I do not like this game." Castiel announced finally.

Dean laughed heartily and shrugged in an exaggerated fashion.

"Let's play one more time." Castiel said seriously.

"Your loss." Dean said for the second time that night.

Jack sighed at Castiel's predicament, finally giving up on the idea of sleeping. "I'm going to go check out the motel art in the lobby, maybe some walking might wear me out."

Dean looked at him like he was crazy. "Okay, suit yourself."

"Don't go outside." Castiel called out as Jack left the room.


Jack observed the art work with mild interest. There were rows of paintings of abstract landscapes. He hummed at the colour scheme in agreement, the burnt oranges, mustard yellows and cornflower blues strangely blended in nicely with the olive wallpaper of the motel.

He moved from the lobby back into the hallway to look at the paintings that lined the walls, intending to slowly make his way up to his room after that. Jack passed the communal bathroom, he could hear Sam showering in there.

"Dean is right, Sam sure does take a long time in the shower." Jack noted to himself.

Bored and no longer interested in looking at anymore paintings, he turned to leave, but that's when he heard it, a rhythmic rapping noise. Instinctively Jack went on guard and cautiously moved towards the source of the sound, tiptoeing quietly but quickly down the corridor. It was coming from one of the bedrooms. Jack stood in front of a door, and the thumping was unmistakably coming from behind there he decided.

He pressed his hands against the wall next to the door and felt the regular vibrations. "What is that?" Jack said quietly to himself. Someone moaned as though they were in pain. Jack felt anxious, "What if someone is in trouble?" He considered going back and getting Dean and Castiel for back up, suddenly aware of the fact that he didn't have a weapon on him.

A strangled gasp escaped the room and Jack decided he needed to act now. He launched himself at the door, using the side of his shoulder to violently push it open. The door spun on its hinges and noisily hit the wall on the interior side of the room.

A woman screamed in surprise.

Jack paused to take in the scene before him, he simply stood in the doorway stunned. There was an overweight naked man repeatedly slapping a woman that lay under him with his body.

Upon spotting Jack, the man paused his activity and hovered over the woman, he looked at the newcomer in shock. The woman looked terrified, she used that brief pause to hastily grab at the bed sheets and cover herself.

"Are you fucking insane?!" The man shrieked.

"Get away from her!" Jack shouted as he finally willed his legs to move. He saw the lampshade beside the bed and made a dive for it, he thought he could use it to hit the man over the head.

"Get the fuck out!" The man yelled, also making a move to get up.

Just as Jack was about to grab the lampshade, he heard rapid footsteps behind him. He spun around anticipating an attack. He was shocked to see Sam standing there, towel haphazardly tied around his waist, still dripping wet from his shower.

"Jack!" Sam spoke urgently. "Are you alright?! I heard someone scream."

"No!" Jack yelled desperately. "This man is trying to hurt this woman!"

"What?!" The man glared back defensively. "How dare you!"

Sam looked at the couple on the bed, taking in their nudity and quickly putting two and two together. Was Jack trying to say that this man was trying to force himself on this woman? His eyes darkened at the thought.

"This man is insane!" The naked man yelled back viciously pointing at Jack. He quickly covered his front with a pillow realizing he was exposing himself. "He just burst in here." He continued, giving Jack a filthy look, he might have been able to take on Jack if it had been him alone, but now there are two of them he thought sourly.

Sam ignored the man and addressed the woman. "Are you alright miss?"

"Of course I'm not alright!" She cried angrily.

Jack could see she was shaking under the sheets, he took a step towards her protectively, ready to jump into action any second.

"What is wrong with all of you?!" She seethed. "This is a private room! I'm here trying to enjoy a night with my husband, when you just barge in here! How dare you?!" She looked angrily between Jack and Sam.

"So you're okay?" Sam asked uncertainly.

"I will be when you all get the hell out of our room!" She replied venomously.

Jack looked at her with concern.

"If you don't leave right now, I'm going to call the police." Said the angry naked man.

A horrifying realization began to dawn Sam, as he swept his eyes over the woman, the naked man and Jack, he felt his mouth hang open.

Jack noticed Sam turning red. "Sam are you okay?!"

Sam numbly tugged at the hem of Jack's shirt. "Jack we need to leave." He said calmly.

"What?! We can't just leave! He was hurting her!" Jack exclaimed.

"Now listen here young man." The naked man said sharply, though still not moving from his spot on the bed.

"Jack we need to leave now!" Sam said more firmly.

Jack noted the seriousness in his voice and looked back at the couple dumbfounded.

"But…l" Jack started.

"We're so sorry! This has all been a terrible misunderstanding!" Sam stumbled on his words as he pulled Jack towards the door. He used his other hand to secure the towel around this waist, his own partial nudity adding to his embarrassment.

At this point Sam was practically pushing Jack out the door, much to the other's annoyance.

"Fucking unbelievable." They heard the man say as Sam shut the door.

Still clad in only a towel, Sam stopped at the bathroom to pick up his clothes.

"Why did we just leave?" Jack questioned him, clearly still upset.

"We can talk some more once I put some clothes on." Sam shot back irately. It was rare that Sam would speak to him in that way, Jack couldn't help but feel a little hurt. It must have showed on his face.

The older man softened his gaze and sighed heavily. "I'm sorry, I didn't…" Sam started, not sure of what to say. "Jack…do you know what that was?"

"He was hurting her." Jack said sounding sure of himself, glancing back at the room they had just left.

"No…he wasn't." Sam said slowly, he sighed again as the other tilted his head in confusion. Jack's answer confirmed Sam's theory that Jack didn't know what sex was.

"Jack listen." Sam tried again.

Jack looked up at Sam expectantly, for the first time noticing the bruising on his torso from where the older man he had apparently fallen in the garden.

"Look I'll tell you what, why don't you shower up?" Sam said causally. Jack let himself be nudged towards the cubicle. "There's some soap and shampoo in there. I'll bring you a towel in a bit."

"Okay." Jack said uncertainly, he turned back to the older man. "Did I do something wrong?"

"We can talk more later." Sam replied reassuringly. He paused at the doorway and looked back at Jack who had still not moved. "I'm not mad." Sam said and offered a small strained smile.

Jack also smiled back, but he was undeniably and thoroughly confused over what had just occurred.


Inside Sam and Dean's room, Dean's voice roared with laughter.

"I see, so that's what happened." Castiel said seriously.

"Oh man, I wish I had been there to see that!"

"Dean this isn't funny!" Sam glared at his brother.

"No its fucking hilarious!" Dean almost fell off his chair wheezing. "I almost feel sorry for him!"

Sam could feel his lips twitching upwards, aching to join in the laughter but he forced it down. "Stop being so damn immature. We're lucky nothing more happened."

Dean sobered up slightly, taking in his brother's expression. "Look, its not a big deal. Someone just needs to teach the guy about the sweet old birds and bees!"

Simultaneously, both Sam and Dean's heads turned to face the angel in the room.

Castiel stared back helplessly.


A/N: And that's chapter 1! Its kind of a mix of humour and drama I guess. Anyway, hope you enjoyed it!

As always, please excuse any grammar/spelling errors.

NEXT CHAPTER: "Chapter two: A talk with Castiel"