Supernatural: Watch Over Me Ch. 01

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A trip home proves to be more pleasure than business.
8k words
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23.4k
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Part 3 of the 5 part series

Updated 08/31/2017
Created 12/21/2009
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The characters of Dean and Sam Winchester (and Bobby Singer) are from the TV series Supernatural and are owned by Eric Kripke and the CW Network. I love to write about the Winchesters; the characters and the men that play them are so sexy! They sure make it easy to come up with story ideas.


Sam Winchester sat in the corner of the cozy coffee shop typing away at the keyboard of his laptop. He glanced across the room to see his older brother Dean leaning against the counter, flirting shamelessly with the cute blonde barista.

"I can't take you anywhere, Dean." Sam thought to himself with a smile, amused at how Dean could zero in on any female within a ten mile radius.

"Man, that chick is so hot!" Dean said as he pulled out a chair from the table where Sam was sitting. "I scored her number too!"

"Good for you." Sam replied, not looking up from the computer screen as he continued to peck away at the keys.

"Hey." Dean said, closing the laptop on Sam's fingers, forcing him to look up. "If you'd get your nose outta that computer, you'd see that there are a lot of hot women in here!"

"Yeah?" Sam glared at him, pulling his fingers out from under the folded screen. "Well, we have bigger things to worry about."

"Like what?" Dean leaned back in his chair, sipping his coffee. "We're supposed to be having some 'R&R' for a while, remember? We've definitely earned it, Sammy."

Before Sam could answer, a waitress walked up to their table. She was a very pretty brunette with deep brown eyes. "Can I refill your coffee for you sir?" She asked Sam with a lingering smile, nervously putting the end of her pen in her mouth. "Would you like a pastry or something else from the menu?"

"No, I'm fine. Thanks." He looked up at her and smiled politely.

"Ok, but let me know if you need anything. Anything at all." She said with a smile and a quick wink.

As she walked away, Dean was checking out every inch of her. When she disappeared around the corner, he hung his head, shaking it. "I can't believe you Sam. You are such a dumbass!"

"What are you talking about?" He asked, opening the laptop. "What did I do now?"

Dean looked up and smiled. "That hot waitress is totally crushing on you, and you just sit here like Mr. Clueless! She was flirting with you like crazy!"

"She was just doing her job, that's all." He replied flatly. "She gets paid to be nice to customers, that's how she makes more tips."

"I don't think so, Sam." Dean smiled a sly grin. "And I'm gonna prove it to ya. I think it's time you had some fun and stop being such a stick in the mud!"

"Dean, don't you dare!" Sam whispered, knowing his brother was about to do something really embarrassing.

When Dean saw their waitress, he waved at her trying to get her attention. When she didn't look up, he yelled across the room. "Oh, waitress? Yeah, we need your assistance over here!"

Sam wished the floor would swallow him up at that exact moment. He could feel his cheeks begin to burn slightly in a blush. "I'm gonna kill you!" He said between clenched teeth as the pretty waitress walked toward their table. "I've always wondered what it would be like to be an only child."

"Hi guys." The waitress said with a bright smile. "Did you change your minds about needing something?"

"Yes we did." Dean winked at her. "My brother and I have a bet going, and I think you're the only one that can settle it."

Sam glared at Dean as the pretty waitress put both hands on her hips. "Oh really? How can I help you two handsome guys?"

"I'm Dean, by the way." He smiled a sexy smile, extending his hand. "And this is my brother Sam."

The waitress slid her pen into the back of her ponytail and put her pad into her apron to free up her hands. "Nice to meet you Dean." She shook Dean's hand. "And it's very nice to meet you Sam." Her eyes locked on his, and he couldn't help but notice her emphasis on the word very.

"Hi." Sam said politely with a forced smile. He was still pissed off at Dean and really wasn't up for conversation.

"My name is Karen. So how can I help with your bet?" She asked, keeping her gaze on Sam. She was definitely smitten with him.

Dean motioned for the waitress to come closer. "Well Karen, we have a bet that whoever guesses what color of panties you're wearing gets your phone number."

Sam could feel his cheeks begin to burn a little hotter now. His first blush had subsided a little, but he couldn't believe what had just come out of his brother's mouth. "My brother the pervert." He thought to himself as he waited for Karen's response. Sam secretly hoped she would be so insulted she would slap Dean across the face for such a comment.

"Interesting." Karen smirked as she looked at the two hot guys that sat at her table. She was really glad she had come into work today. There's not many days that two hotties such as these came into the coffee shop, much less sat at her tables. "But what if I'm not wearing any panties at all?" Karen leaned down and whispered in Dean's ear.

Dean swallowed hard. He could feel all the blood running straight to his cock. He took a few seconds to regain his composure and spoke up. "Well, I guess we'd just call it a draw then. My guess is that you are wearing a black lace thong."

Karen moved quickly to the back of their table. As she passed behind Sam's chair, she lightly ran her hands over his broad shoulders. "Mind if I sit here for a sec?" She asked him as she pulled out the chair in between the two brothers.

"No, go ahead." Sam replied, moving his laptop to the side so she could sit down. He gave Dean a look that could kill, but Dean totally ignored the eye daggers because he was still horny from her no panties comment.

"So what's your guess Sam?" Karen leaned in toward him, her brown eyes scanning every inch of his handsome face.

"Uh." He squirmed under her intense gaze and the question at hand. "I dunno."

"C'mon, you must have a guess at what color of underwear I'm wearing." She purred.

Sam could feel his cheeks begin to burn more violently as the moments ticked by. He knew he would have to come up with an answer or she wouldn't leave him alone. "You have on white thong panties with multi-colored polka dots."

"Mmmmm." Karen sat back in her chair. "Let's see." She whispered as she reached up under her short skirt with both hands. Sam and Dean both watched her intently as she raised slightly in the chair to pull her panties off her hips. She let the panties slide quickly down her legs and onto the floor. Dean's erection was painfully straining against his jeans and Sam's mouth suddenly went dry. Even though he wasn't attracted to Karen that much, the brazen move of removing her panties in a public place got his attention.

Dean looked over at Sam and gave him a wide-eyed look. Even Dean seemed surprised, and Sam knew his brother had seen some freaky stuff on the road.

"I've gotta get back to work." Karen took a page out of her order pad and scribbled her phone number on it quickly. She then bent over while still sitting in her chair and discreetly picked up her panties from the floor. She stood up, adjusting her short skirt on her hips. "Can't stay here all day playing with you two." She laughed, taking one finger to Dean's chin and closing his gaping mouth. "Even though I'd love to!"

"Good guess, Sam." Karen stood behind him. "You're the winner. Call me sometime." She whispered huskily in his ear, sliding her panties and phone number into his front shirt pocket.

Sam's face was on fire at this point. He looked around the coffee shop to see if anyone had witnessed the steamy display. Everyone at all the other tables chatted, read the newspaper, or stared at their computer screens oblivious to what had just happened at their table. When Karen had gotten out of earshot, Dean leaned over the table. "Well, Sammy I hate to say that I told you so...but I told you Karen was hot for you! Maybe next time you'll listen to me!"

"I am so not talking to you right now." Sam said, taking a sip of coffee and moving the laptop back in front of him.

"C'mon Sam, don't be like that! You should be thanking me for hooking you up with such a babe!"

Sam just sat there totally ignoring Dean as he continued to talk. When Dean realized that he wasn't even listening to him, he stood up. "I'll be waiting out in the car when you get through PMS-ing, Samantha."

Sam continued to peck away at the laptop's keyboard. Dean stood up and slammed his chair against the table and walked briskly toward the door. "What a jerk." Sam thought to himself as he watched this brother walk out the door and into the parking lot.

Dean could be so relentless when it came to hooking Sam up with women. He tried to tell Dean that he wasn't ready for a new relationship ever since the death of his girlfriend Jessica a little over a year ago. He just wasn't ready to let go and give his heart to another woman just yet.

He knew his older brother meant well; all Dean ever wanted was for Sam to be happy and to have someone to love. Dean met women all the time on the road, and he had no trouble connecting with them and having a good time. Sam wasn't so quick to find a connection with someone. There had to be more there than just the physical.

"I guess I'd better go on out to the car and make up with him." Sam said to himself, closing the laptop and putting it under his arm. He took one last swallow of his coffee and stood up. Out of the corner of his eye, he saw Karen standing at the counter with the blonde barista Dean had been talking to earlier. The two women stared at him and giggled. Karen waved as he passed by heading for the door, and then made a gesture with her hand for him to call her.

He gave her a half smile and a nervous wave as he threw the empty plastic coffee cup into the trash can. "What the hell ever happened to playing a little hard to get! Damn!" He thought to himself as he walked outside to where Dean was sitting in their Impala.

Dean sat there with his dark sunglasses on staring out the driver's side window. Sam hesitated with his hand on the passenger's side door handle. Taking a deep breath, he opened the squeaky door to the car and got in.

The two brothers sat in complete silence for several seconds. Sam reached into the backseat and slid the laptop into the messenger's bag that was lying on top of his coat. Turning around in the seat, he glanced over at Dean who seemed frozen.

After several more seconds that seemed like an eternity, Dean finally spoke up. "Did you get some Midol for your PMS while you were in there?"

"Dean, we need to talk." Sam said calmly.

Dean ripped his sunglasses from his face. "You're damn right we need to talk! Here I am trying to help you out and deliver you tail on a silver platter, and you give me the silent treatment. Man, that's real gratitude, Sam!"

Sam figured his brother would react this way. He knew the best thing to do was to let Dean get it all out of his system. If it meant that he blew his top, so be it. "We've had this discussion before, Dean. I'm just not ready to meet anybody new yet. You have to understand and respect that. I'll know when I meet the right woman and the time is right."

"I just don't understand you sometimes, Sam." Dean threw his sunglasses into the console near the gearshift. "Sometimes I wonder if you were adopted. We are as different as night and day."

Sam hung his head at the stinging comment by his brother. "So are we cool now?" He replied putting on his seatbelt.

"Yeah." Dean cocked his head to one side. "I guess I have been a little pushy lately. I'll try to respect your wishes from now on about the ladies."

"Thanks." Sam smiled as Dean started the Impala and put it into gear.

"But I still want to see a copy of your birth certificate." Dean looked over, giving Sam a teasing smirk. "Oh, and you don't need to stop for any maxi pads or anything before we leave town, do you?"

"No, I think I'm good." Sam rolled his eyes.

"Hey, do you still have those panties Karen gave you?" Dean asked as they reached the outskirts of the small town.

Sam had totally forgotten about the panties in his front shirt pocket. "Yeah, I've still got 'em. I didn't want to throw them in the trash right in front of her!" He reached inside his shirt pocket and pulled out a pair of white thong panties with multi-colored polka dots.

"Well, I'll be a son-of-a-bitch!" Dean laughed when he saw the underwear. "You were right! How did you know what color of panties she was wearing? If you have x-ray vision I want in on that! I take back every bad thing I've ever said about you. There may be hope for you yet, Sammy!"

"Lucky guess?" Sam smiled a crooked smile as he held the panties up by the piece of paper Karen had written her number on.

"For heaven sakes Sam, those panties won't bite you!" Dean teased, noticing how gingerly he held the panties. "Have you at least sniffed 'em yet?"

Sam looked over at Dean, giving him a disgusted look. "Dean, that's disgusting!"

"You are unbelievable!" Dean rubbed one hand over his own scruffy chin. "Why do you think she gave you those panties in the first place. C'mon Sam!"

Sam's face flushed a little. "Well, I don't want 'em. Or this number either."

"You are totally hopeless!" Dean laughed. "Open up the glove compartment and throw 'em in there with the rest."

Sam gave Dean a puzzled look and opened the glove compartment. When the small door fell open, hundreds of panties came tumbling out. Sam quickly gathered them off his lap with the new addition of Karen's and shoved the door closed.

"That's my version of a little black book." Dean smiled wickedly. "Where's that number?"

Sam was so shocked by the underwear collection, he just handed him the piece of paper with Karen's number on it without a word.

"Hey, what did you mean back at the coffee shop that we have bigger things to worry about?" Dean asked, shoving the piece of paper into his shirt pocket for safe keeping.

"Oh yeah." Sam piped up, remembering an email he had gotten from Bobby Singer, a long time family friend. "I'm glad you reminded me!" He said, reaching into the backseat and retrieving the laptop.

"Yeah well, panties can be very distracting." Dean laughed as he watched Sam peck away at the keys, opening the email. "But not as distracting as what's in the panties." Dean's thoughts drifted back to the cute blonde barista at the coffee shop.

"Bobby emailed because our cell phones weren't getting a signal. He wanted us to know that we received a letter from the courthouse in Kansas." Sam said quickly. "Someone requested to have the land resurveyed where Grandpa and Grandma Winchester's old homestead is."

"What does that have to do with us?" Dean said, turning his attention back to the road.

"According to Bobby." Sam scanned the email. "Since we are the beneficiaries of the land, we have to be notified that the people that own the land adjacent to ours are trying to contest the boundary lines. Bobby said he would FedEx the letter over to Gramps' house."

"Well, I guess we're heading back home, Sammy." Dean said reaching for his sunglasses and sliding them on his handsome face.

♥ ♥ ♥ ♥ ♥ ♥ ♥ ♥ ♥ ♥

It was early afternoon when the brothers reached the outskirts of Lawrence, Kansas where they had grew up. Both brothers sat in silence as the sign declaring "Welcome to Kansas" whizzed by in a blur. The sign reading "Lawrence 2 mi." glared at them in the distance.

"So do you wanna go out there or not?" Dean looked out the driver's side window, then turned his attention back to the road. He knew his brother knew exactly where he was talking about.

Sam turned to look at Dean. "Yeah, I think we should before we settle in for the night at Gramps' place. It would be kinda bad if we didn't at least ride by there."

"Agreed." Dean replied, then turned the radio up full blast.

For the next two miles they let the blaring rock music fill the car. Sam knew this was Dean's way of telling him that he didn't want to talk about it.

Neither brother wanted to even bring up the painful memories of what had happened over 22 years ago.

When Dean made the turn to head up the road to their childhood home, Sam felt his stomach drop a little. Dean turned the radio off as he saw the old house looming in the distance. The house had been rebuilt since the fire, and someone else was living in it now.

Dean stopped the car just short of the mailbox, parking along the curb. Both brothers sat in silence as a flood of memories came rushing back. The only sound that penetrated the humid air was the growling of the idling Impala.

"So, you ready to head on over to Gramps' place and maybe get some grub, bro?" Dean choked out. Sam looked over to catch Dean making a quick swipe across his cheek. Sam felt several tears building up in his eyes too.

"Yeah, let's go." Sam replied, quickly wiping his own eyes.

"The people that live here now might think we're stalkers and call the cops on us." Dean laughed, trying to lighten the mood. "And that's the last thing we need."

"Yeah." Sam smiled. "They're probably dialing 911 as we speak."

The brothers rode on in silence for several miles until the old farmhouse where their grandparents had spent many years of their life came into the distance. The old ranch style house was a bit run down, but still in good shape. Sam and Dean's grandparents had left them the house and land in their will.

"This place sure brings back a lot of memories, huh Dean?" Sam asked as they crossed the one lane wooden bridge that carried them over a small stream. The bridge was the only way to gain access to the house unless you crossed onto the neighbor's land.

"Yeah, it sure does." Dean smiled as the old bridge creaked, and the loose boards strained under the weight of their car.

"It's a miracle this old bridge has held up all these years." Sam laughed, hanging his head out the window. He noticed how the boards slightly raised up as they rolled slowly along.

"This old bridge barely survived us!" Dean laughed. "Remember when we rode our dirt bikes across the bridge trying to see who could knock the most boards into the water?"

"Yeah, Dad was so pissed at us! He and Gramps spent a lot of hours fishing loose boards outta that stream! But I don't think Gramps minded it too much. He just laughed about it."

"I sure miss the old guy, and Grandma too." Dean replied as he pulled the Impala up the winding driveway and stopped in front of the old house where they had spent a lot of their childhood.

"Me too." Sam sighed, feeling a rush of nostalgia. "I can almost hear Grandma yelling for us to come into the kitchen for a peanut butter and jelly sandwich. She was always trying to fatten us up."

"You didn't need fattening up, Pudgy." Dean snickered as he put the car in gear, taking off his sunglasses.

"I had a thyroid condition until I hit puberty." Sam snapped back.

"Oh, you've finally hit puberty?" Dean replied getting out of the car, then bent down to smirk at Sam. "I hadn't noticed. You still act like girls have cooties!"

"Bite me jerk!" Sam huffed as he opened the passenger's side door and got out, slamming the door.

"Whatever bitch!" Dean shut his door and stretched. "All this talk of peanut butter and jelly sandwiches has made me even hungrier! But I could really go for some pie right about now!"

"I could go for a juicy double cheeseburger and fries myself." Sam said, squinting from the bright sun as he scanned the front porch and doorway for the envelope Bobby was supposed to send.

"Let's go inside and see if there's anything we can eat in the cupboards." Dean said as the two brothers approached the house.

"Here's the letter." Sam bent over to pick up the white FedEx envelope the carrier had left against the front door. He quickly tore it open as Dean reached behind one of the posts on the front porch and retrieved the front door key.