Winchester Family Vacations

Chapter 1

Dean wasn't the type of guy that needed a vacation. Well, that wasn't entirely true, he thought. He was definitely the type of guy that needed a vacation. He just wasn't the type of guy to actually take a vacation. Every vacation the Winchester family had ever taken through the years hadn't ended well and he was pretty sure it was just another curse brought onto his family by something with an evil and sick sense of humor.

The first vacation he could remember was the summer before his mother died. Of course, he didn't really remember much about it, but he'd heard his dad talking to Bobby once about how that had been both the best and worst summer of his life. He'd told the older hunter about their trip to the state fair and how it had turned out so disastrous that Mary vowed to never take another vacation again.

Dean had been twelve years old when he heard the story the first time and something thrummed deep inside of him at the distant memory. He really didn't have actual memories of the trip, but he definitely had a sense of what a disaster it had been.

According to John, they had driven 187 miles to the fair because Mary wanted to see the music guests- Alabama, Kansas, Charlie Daniels, The Oakridge Boys, and Willie Nelson.

John thought it was a crazy thing to do when they had a four year old little boy and a four month old baby to drag along. With the temperature almost soaring into the nineties and the average crowd size of almost forty thousand people a day, John was convinced that the whole idea was ridiculous. But who was he to rain on Mary's parade, right? If she really wanted to go, he would be there with her.

The trip had taken almost five hours thanks to a hungry baby, a carsick four year old who had eaten too much candy the night before, and not just one, but two flat tires. John was ready to turn the car around and head back home, but all it took to change his mind was one look from his wife. One look into her blue-gray eyes could usually make him do anything.

Once they'd arrived at the hotel they'd booked in Hutchinson, they were all exhausted. Dean's shirt was covered in vomit and he was extremely cranky. Sam was hungry again and was wailing at the top of his lungs at the injustice of having to wait a few more minutes to eat. Mary was exhausted, but trying to put up a good front, not wanting John to know that she was ready to turn around and go home, too. And John needed a beer.

Unfortunately, there was a mix-up at the hotel and their reservation had been cancelled. John's patience, by that time, was completely used up and Mary sent him to sit in the lobby with the boys while she figured out what to do. John was pretty sure that he got the worst end of that deal since Sam was still crying and Dean was still cranky.

Eventually, they were given a room, though, and Mary was quick to get the boys fed, bathed, and into bed. John wasn't too far behind.

The next morning was a whole new day and John and Mary met it with great expectations. Dean was in a better mood after getting a good night's sleep and Sam was back to being the happy baby he usually was, so they quickly headed for the fairgrounds. By the time they got there, Dean had worked himself up into such a state of excitement that John had already threatened to turn the car around and go back to the hotel. He also threatened him twice with a spanking when Dean didn't listen. Dean quickly settled down after that, since he didn't want the day to be ruined.

The first few hours passed without incidence and Dean was having the time of his short life. He was happiest whenever his dad went on one of the carnival rides with him and he especially loved the bumper cars.

Sam was having fun, too, looking at all the people around him and staring up at the carnival rides. The sounds didn't seem to bother him at all and people passing by the small family would often stop and smile at the smiling baby. John thought it funny when Dean would become overly protective of his little brother.

The first incident that started the downward spiral of their day was when Sammy started freaking out. Dean was just coming off of another ride with his dad when he heard his brother screaming loudly. John had been holding onto Dean's hand, but the boy quickly pulled away as he ran to his brother. By that time, John had figured out that Sam was screaming and he took off running, too. He came to an abrupt stop when he saw the look on Mary's face. Instead of looking scared or angry, she was smiling and laughing.

John quickly looked around and saw what was making Sam cry. Standing right in front of the baby was a carnival clown with a full face of clown make-up and a red wig. The man was trying to get Sam to stop crying, but it wasn't working. Instead, Sam was crying even louder.

By the time John arrived at Mary's side, Dean was already there, standing protectively in front of his brother. John and Mary watched in horror as Dean reeled back and kicked the clown right in the shin. The man barely had time to react to the pain when another kick landed on the other shin. By the second kick, John moved forward and grabbed Dean, picking him up as he apologized profusely to the clown. He could see that Mary was trying to keep from laughing at what had happened, but he couldn't do anything but try to contain the four year old that was struggling to get down.

Eventually, Mary and John had apologized enough to the clown and the man had stormed off, limping unevenly from Dean's kicks. Mary was finally able to calm Sam down and John had given Dean a bit of a talking-to for running off like he did. He didn't scold the boy for kicking the clown, though, since Dean thought that he was protecting his little brother.

After everyone was calmed down, they took a break from the rides and grabbed lunch. Once they were done eating, Mary talked John into going into the exhibit halls for a while. Dean wasn't happy about leaving the midway, but he followed along anyway.

Halfway through the art exhibit was the first time he wandered off. Mary and John were looking at some painting that had caught their eye and Dean had spotted a stand several yards away that had toys. Looking up at his mom and dad and realizing that they weren't paying attention, Dean decided he would go check out the toys on his own. He was gone all of three minutes before he was suddenly grabbed from behind by a somewhat panicked John Winchester.

"Dean! What are you doing?! You can't just walk away from us like that, okay?"

Dean looked surprised by the panic on his dad's face, not really understanding what the big deal was. He really hadn't gone that far away.

The second time he wandered off was worse. Mary had taken Sam to the bathroom to change his diaper while John and Dean were standing in line to get some snacks. John was in the process of ordering when Dean decided to walk over to the ring toss game. He didn't think it was that far away from his dad, but when he turned to go back, he couldn't find him.

It took John almost a full minute before he noticed that Dean wasn't hanging onto the hem of his t-shirt anymore. His heart started to pound painfully when he looked around and couldn't find his son. And it continued to pound, growing more erratic with each passing second.

Forgetting all about the food that he had already paid for, John moved around the area, pushing people aside as he called out for Dean. Minutes later, Mary returned from the bathroom, immediately realizing what was happening, and suddenly her heart was pounding just as painfully and erratically as her husband's.

It was almost a full hour before someone pointed them in the direction of the Lost and Found area and both Mary and John breathed a long sigh of relief when they entered the tent to find Dean sitting on a bench, an ice cream cone in one hand and a stuffed tiger in the other one. Mary rushed over to Dean, taking in the tear-streaked face and the obviously sticky hands. Dean, for the most part, looked like he was doing okay, but he jumped up when he saw his parents. Within seconds, Mary was holding the little boy in her arms, kissing his face and squeezing him so tightly that he was having a hard time breathing.

Once she was done, John took his turn, too. He held onto his son tightly, breathing in the scent of little boy-ness mixed with dirt and sweat. After several long seconds, he put Dean down on the ground, turned him to the side and placed a hard swat to his backside. Dean immediately started crying and both Mary and the young woman that had been watching over Dean sent John a scathing look.

He didn't care, though. He had had enough of Dean wandering off and he was determined to put a stop to it.

"What did I tell you about wandering off, Dean?" John asked the still crying little boy. "I told you to stay with me. I told you how dangerous it was to wander off, remember?"

Dean didn't answer his dad. Instead, he buried his face into the man's pant leg, rubbing his dripping nose into the man's jeans.

After thanking the young woman for watching Dean, John gathered him up into his arms and followed Mary out of the tent. They were both spent with the exhaustion of their fear and were ready to head back to the motel. Dean, on the other hand, was ready to go back to the midway and ride some more of the carnival rides.

After a few more tears and a little bet of begging from Dean, Mary and John decided that they would stay a little longer. Unfortunately, that decision led to another situation that would haunt them for a while.

By the end of the day, the little Winchester family was exhausted and a little sunburned. Dean was begging to go on one more ride and his parents finally gave in. John walked Dean over to stand in line for the little kid's Ferris Wheel. He was surprised when Dean still wanted to go on it after he found out that adults couldn't ride it. The boy was independent in a lot of ways, but he had yet to ride a single carnival ride on his own.

Mary and John stood under a shade tree while they waited for the ride to finish. Sam was sleeping soundly in his stroller, his cheeks a little pink from the sun. Mary was leaning up against John, obviously more than ready to call it a day. And John was keeping an eye on his oldest boy.

Dean's face was filled with awe and wonder as the little wheel rotated around and around. Every time his car came into view, Mary and John could see the huge smile on his face. Mary wished she'd remembered to bring a camera with her.

Figuring the ride was just about over, John made his way over to the exit to wait for Dean. He had been waiting for almost two minutes when he heard a loud screeching noise and someone screaming loudly. Looking over at Mary, he realized that she was staring up at the Ferris Wheel in complete horror. John turned his attention to the ride and immediately saw what had everyone so scared- the wheel was still turning, but one of the cars was hanging off of its arm, swinging violently back and forth.

John felt relief shoot through him when he realized it was a yellow car and not the blue one that Dean was riding in. That relief was short-lived, though, when he heard the panicked crying of the two children that were trapped inside.

Quickly jumping into action, John ran forward to help in whatever way he could. The young man that was running the ride looked terrified and seemed to be frozen in place. John tried to talk to him, asking where the emergency shut-off lever was, but the kid was too scared to talk. Eventually, John found it himself and shut it off. They all watched as the wheel came to an abrupt stop, causing the broken car to swing even more dangerously.

Without a second thought, John started climbing the wheel's structure, slowly and steadily making his way to the broken car. He passed by the blue car and saw Dean's wild eyes looking back at him.

"It's okay, Dean. I'll have you down in a minute, okay? Just sit still, kiddo. Don't move."

Dean nodded his head and sat back against the seat, determined to do exactly what his dad said to do.

Everyone on the ground watched breathlessly as John continued his ascent up the wheel. It only took him a few more minutes before he was walking out on the arm of the broken car, talking gently to the two kids in the car. He tried to calm them down, telling them the same things he'd told his son. "It's okay." "Just sit still." "Don't move."

Luckily the car's swinging had slowed way down. The kids inside the car watched as he precariously leaned out over thin air to open the cage door that had enclosed them inside the ride. Seconds later, he had the door open and was trying to coax one of them to move towards him.

It took several minutes of coaxing, but eventually the little girl slowly scooted over on the seat, making her way over to him. Once she was over as far as she could be, John reached out to her, telling her to grab his hand. It took several more minutes of telling her that he wouldn't let anything happen to her before she finally reached out tentatively. Luckily, she was a small girl and John was able to easily grab her and pull her to him. With her safely tucked against him, John tried to figure out what his next step was. He didn't want to have to climb all the way down with her and climb back up to save the little boy, but he really didn't know what else to do. It wasn't until he looked down to start his descent that he noticed another man was climbing up the structure. Within minutes, the man was right below him and he easily handed the little girl over to him.

Once they were on their way back down, John turned his attention back to the remaining child. The little boy was a little bit harder to convince to scoot over to him, but eventually he did. John wasted no time in grabbing the boy and after he was safe in his arms, John started climbing down.

He passed Dean's car again and was proud to see that Dean was doing exactly what he was told and was being very brave about it.

"Just a few more minutes, Dean, and I'll have you down. Hang in there just a little bit longer, okay?"

"Okay, Daddy," Dean said bravely.

John made his way down the rest of the way and deposited the scared little boy into his mother's arms. He thanked whoever might be listening that the yellow and blue cars were the only ones with any riders in them and without a single second of hesitation, he put the wheel back in motion, bringing Dean's car back to the boarding level. He opened the door as fast as he could and suddenly found his arms full of his four year old.

"It's okay, buddy. It's all over."

Dean dug his face into his father's neck and John could feel the small body trembling. Rubbing his hands up and down Dean's back, he hurried over to Mary, knowing how worried she was. Mary immediately took Dean out of his arms and held him tightly.

They were all exhausted and eager to call it a day. And once the small family settled into their hotel room for the night, they quickly realized that they were ready to call a halt to their vacation. Both Mary and John were ready to go home and put the last two days- and the Kansas State Fair- behind them.

Thinking back on that story, Dean was reminded once again how nothing ever seemed to go well for the Winchester family. He wondered how Sam could even suggest that they take a few days off from their attempts to find Dean a way out of his demon deal. Taking a few days off had never worked for them and usually led to some crazy, chaotic mess. A mess they just didn't need at the moment.

"C'mon, Dean. Just a few days, okay? I just want to go somewhere where we can get some fresh air and maybe even some decent sleep. Please?"

Sam looked up at him with his patented puppy-dog eyes and Dean felt his resolve melting. He tried one last time to talk Sam out of his crazy plan, but couldn't get past the eyes and the slightly pouting mouth.

"Damn it, Sam. You know this isn't going to turn out good. Not for us."

"I'm sick of hearing about that whole "Winchester family vacation curse," Dean. Everyone's family vacations are a mess. Not just ours."

Dean wanted to argue that it wasn't the same, but he didn't. If his little brother wanted to lie to himself, then so be it. Dean wasn't about to lie to himself. He knew. He knew that his family was cursed. And that Winchester Family Vacations were something better left in the past.

Author's note: I went on an Anniversary trip this weekend and something inspired this little story. I have no idea how long it's going to be, but I imagine at least a few more chapters. There will be a definite plot to the story, so hang in there, guys. And don't worry…. I'll be updating my other stories soon.

And thanks for reading. I'd love to hear your thoughts.