Full Summary -

Dean and Sam grew up stopping by the Stilinski's house throughout the years. Then the summer after Stiles gets possessed he ends up briefly in the hospital again due to some magical beasts rolling through. Papa Stilinski, who has known about the supernatural and the Winchesters plus Bobby's involvement with it, decides to send Stiles with Dean for the summer to get properly trained. After all, he knows Stiles won't stop helping his friends and the best way to prepare him is to be trained by someone whose life is dedicated to dealing with the supernatural. Story takes place from them all as kids, Stiles experience with Scott becoming a werewolf (teen wolf season 1 through 3 loosely followed), to Stiles adventures on the road with Dean (pre-SPN season 1) and onward.

Author's Notes -

Timeline is all messed up to fit with plot. The first several chapters will be broken up by year. They'll have events that happened over the years that developed the Winchester's relationship with the Stilinski's. There will be a time leaps to move the story along. Then it will get to the "present" of Stiles heading out onto the road with Dean.

The setup of how the boys lived when they are younger diverges from what we know in canon. I have them spending a lot more time with Bobby. I figured John would have tried to give them a few stable years of staying put for an extended period of time. Leaving them with Bobby seemed like the most logical thing. Also, I dislike the John Winchester (maybe due to how he is portrayed in fic, idk). So he is shown putting hunting and revenge ahead of his own kids.

Potential Warnings - This is a slash story and there will be smut later on. You've been forewarned. I have the majority of this story written but it can be edited for who Stiles ends up with. Really, it's what you guys want. So review with whether or not he should end up with Dean or Derek. Also, the underage takes place with a kiss between a 16 year old and 21 year old. As well as several instances between a 17 year old and a 22 year old.

For the purposes of this story here is the years each boy was born in:
Dean – January 24, 1979
Sam – May 2, 1983
Stiles – June 7, 1984

Chapter 1 - 1984

August 1984

Dean- 5 years old; Sam- 1 yr and 3 mo. old; Stiles – 2 months old

Tom Stilinski had made several friends throughout the years due to his line of work. Back when he had simply been a deputy for Beacon Hills PD two men had arrived one evening after a series of frankly mysterious murders that no one seemed to be able to figure out. The two men claimed to be FBI agents. But, from the very get go Tom hadn't been fully convinced. The classic muscle cars both men drove didn't scream FBI. Tom had enlisted himself in personally assisting the two men. That decision, of butting in when it wasn't necessarily his business, lead to the revelation of the supernatural. Turns out there was a group vampires making their way through the town when they had decided Beacon Hills was ripe for the picking.

After everything was said and done the two older men revealed their identities as Bobby Singer and John Winchester. They gave him a brief and blunt explanation of the supernatural and the danger constantly lurking in the dark. During this entire conversation it had taken place in one of their hotel rooms. They had been interrupted by a young boy no older than five coming from the back room announcing his little brother needed something. John had left to contend to his children while Bobby had quickly explained why the hell two kids were tagging along with them as they hunted demons and monsters. At the end they had all shared a cup of cheap scotch and parted ways. Before they went their separate ways though Tom had told them both to look him up if they were ever near-by or needed some official police help. He too had promised to contact them if anything supernatural like seemed to pop up again in Beacon Hills. Needless to say when Tom had gone home that night he had held his wife and newborn son a little closer than usual.

Never did it cross his mind how the two small boys he had briefly seen would become such a large part of his life…

Early July 1987

Dean – 8 years old; Sam- 4 years old; Stiles – 3 years old

Tom honestly never expected to see John Winchester or Bobby Singer again. He'd called them once about a year after their meeting to let them know about some suspicious activity a few towns over. Only Bobby had swung by after to share a beer with Tom before heading on his way.

So, when Tom received a call early Tuesday morning in July from Bobby Singer he was a bit surprised. According to the older and scruffy man there was another hunter nearby. Apparently there were a lot of hunters. The unnamed hunter needed some help and Bobby had been the closest.

Only hitch was that for some reason Bobby had John Winchester's kids with him. The older man didn't go into much detail. Simply saying the two boy sometimes stayed with him for extended periods of time. Bobby knew the hunt would take a few day and didn't want to leave the two boys alone in a motel. So, he'd called Tom asking if he wouldn't mind watching them. He had been sure to make it clear the deputy was in no way obligated. But, Tom's wife who had been listening had agreed easily to the request. Bobby and the boys would be there later in the day.

Tom Stilinski was a man deeply in love with his wife. Claudia had noticed something off with her husband shortly after Bobby and John's initial departure three years prior. Tom had told her everything, and she had easily accepted it all. It made sense that there was more in the world than just humans. It didn't keep her up at night but she was mindful of the fact there was something else out there.

Claudia's maternal instinct had fueled her to saying yes to allowing the two boys to stay with them. From what her husband had told her based on the information shared by Bobby was that the boy's mother had died and they travelled with their father. Claudia wanted to give them some semblance of normal. Even if it was only for a few days. She'd set up the guest room for them and happily chatted to their three year old son about their visitors.

The doorbell rang shortly after noon. Tom and Claudia exchanged a look before heading towards the front door. Tom opened it to reveal two young boys standing in front of Bobby. The older of the boys holding duffel bag.

"Bobby." Tom said with a nod of acknowledgement.

"Tom." Bobby replied then patted both of the young boy's shoulders. Tom had never gotten their names in the past. "Well, this here is Dean and his younger brother, Sam. They shouldn't give you too much trouble. They're good boys." Bobby informed the couple.

"I'm sure they won't. Nice to meet you all. Hello boys, my name is Claudia. I hope you like grilled cheese sandwiches and tomato soup." Claudia said in warm tone with a smile as she ushered the boys inside.

"That's Dean's favorite!" Sam exclaimed to Claudia as they walked into the house. "I like it too but sometimes when Dean makes it the cheese is not melted all the way." Sam continued as he followed Claudia towards the kitchen.

"Well I certainly hope you like mine." Claudia replied to Sam as they walked into the kitchen together.

"You can just leave the duffel by the door, Dean. We can take it up to the guest room in a bit." Tom told the older boy who still hovered in the entry hall. Keeping an eye on Sam while still looking at Bobby.

"Bobby…" The eight year old started hesitantly.

"Dean, you'll be fine. Both of you are safe here. I wouldn't leave ya with anyone I didn't trust." Bobby reassured Dean. "I'll be back in a few days. Enjoy yourself, boy. Have fun… relax. Be a kid." Bobby finished with a small smile.

Dean nodded once and grinned at Bobby before doing as Tom said, setting down the duffel bag. He quickly muttered a thanks then headed into the kitchen leaving the two adults to talk.

The kitchen was homey, painted a warm yellow color, the fridge was covered with childlike drawings that Dean often received from Sam. The smell from the food was heavenly. "Dean feel free to take a seat and I'll make you a plate." Claudia told him and Dean sat next to his brother.

"Hope you don't mind the crust cut off. That's the way my son likes it."

"You have a son? How old is he?" Deans asked curiously.

"Yes, I do. He's three. He should be down here by now." Claudia said. She down the plate of grilled cheese and tomato soup in front of Dean. "Hope you like it. If not, I can make you something else." She told him and gave him a small pat on the back. Dean stared at the food and glanced over at Sam who was happily munching away.

Dean took a bit of the grilled cheese and about died from happiness. It tasted so good and he felt like he could vaguely remember his mom making sandwiches that tasted this good. He was in the middle of chewing when he heard Claudia yelled a strange name up the stairs telling the person to come down.

A small three year old appeared at the entrance of the kitchen and stared at the two newcomers. He hesitated for a moment before climbing into his own chair across from Dean. "Hi! What's your name and how old are you?" He asked curiously as his mom set a plate in front of him. He quickly said thanks and retuned to look at Dean and Sam.

Sam answered first, "I'm Sam and I'm four." He announced proudly. "That my big brother Dean. He's eight." The three year old looked at them both with a smile.

"Nice to meet you. I'm three and my name is.." he said and even tripped over the pronunciation of his own name.

Dean frowned a bit and attempted to say the small boy's names but couldn't properly get it I out. "I'm sorry. I can't say your name right. St… il… les..a…" Dean tried again but failed. "Can I call you Stiles instead? Would that be ok?" He asked the small boy then looked over at Claudia.

The little boy tested the name out on his tongue. "Stiles… Stiles… yea! I like it!" He stated happily. "Momma, my name is Stiles now ok?"

Claudia laughed but nodded, "Ok, Stiles it is then." Claudia said and gave her son a quick kiss on the head. She looked at Dean and said, "His name is difficult to say. It was my grandfather's name. A Polish name. But, I like Stiles. Very nice nickname." She finished a smile. Dean had been worried she'd be upset with the nickname but simply smiled at her and resumed eating his lunch. Claudia made amazing grilled cheese sandwiches. Maybe this trip wouldn't be that bad.

After some initial awkwardness of how to interact with the new strangers Sam and Dean felt more at ease within the Stilinski household. The newly named Stiles helped quite a deal. He had happily shown them all his toys and told the Winchester's they could play with whatever they wanted. They all got along well enough and soon they were spending the rest of the day running around the house making up adventures. The fun continued for the rest of Sam and Dean's stay at the house.

Three days later there was a ring at front door. Tom opened it to reveal Bobby standing on the other side. "Bobby!" Sam shouted in greeting as he ran to hug the scruffy man around his legs.

Bobby let out a light chuckle and patted Sam on the back. "Hey Sam. You and Dean behave yourself?"

Sam stepped away from Bobby, grabbed his hand, and dragged him past Tom and into the living room where there was an elaborate fort made with sheets and couch cushions. "Oh yea! We were real good. We had so much fun. Look at the fort we made." Sam happily informed Bobby as he gestured to the fort.

Suddenly Dean's head popped out from the entrance of the fort he had a huge smile on his face. "Hey Bobby! Everything go ok?" He asked in as casual a tone as possible while he climbed out of the fort.

"Yea, sport. Things went well. You enjoy yourself here?" Bobby said as he walked into the living room.

"Oh yea! It was a lot of fun. I'm glad we came." Dean told Bobby. The older man was glad to see Dean so happy and finally acting like the eight year old he was.

"Well, I'm glad. But, we gotta get on the road soon. Have to meet up with your dad tomorrow." Bobby informed them and both Sam and Dean let out complaints against leaving.

Stiles crawled out of the fort and tugged on Dean's shirt. "You leaving?" He asked sadly.

Dean turned to Stiles and nodded with a frown, "Yea, Stiles, Sammy and I have to leave now. But, we had a lot of fun with you and your parents."

A deep pout appeared on Stiles' face as he processed Dean's words, "You coming back again sometime though, right?" He asked hopefully. Dean turned and gave Bobby a questioning look.

"Can we come back sometime, Bobby? It's so much fun here!" Sam asked Bobby from his spot near the man. "Pleeaasssee!" Sam continued,

"Plleeeaasseee!" Stiles chimed in mimicking Sam.

Dean just smiled at the both of them then looked at Bobby hopefully.

Bobby then turned to look at Claudia and Tom who were standing by the couch. "It's fine with us, Bobby." Claudia told him with a smile, "We loved having them here." Tom nodded in agreement.

"Any time you boys are with me I'll make sure we swing by for a visit, alright?" Bobby caved. He would have to chat with John later about it. But, hoped the man wouldn't mind too much. As long as Bobby watched them while John was away on a hunt he didn't see the harm in bringing them by.

All three boys let out cheers at Bobby's words. "We'll come back and see you, Stiles." Dean told him with a smile.

"Good. Gonna miss you and Sammy." Stiles told him.

"We'll miss you too!" Sam exclaimed, "Right, Dean?"

"Yea, Sammy. We will both miss you Stiles."

Stiles beamed brightly at this with a toothy grin.

"Ok, boys, I packed lunch for you. Say your goodbyes while Bobby and Tom load up the car." Claudia told them. This caused the boys to give each other hugs and say their goodbyes to Stiles. Sam ran up to Claudia and gave her a big hug before doing the same to Tom and heading out the door.

Dean walked up to both adults and sheepishly said, "Thank you, both. Sammy and I had a lot of fun here…. I'm glad you want us to come back… Stiles is a lot of fun to be around."

Tom patted Dean on the shoulder and gave him a quick one armed hug, "You're welcome here anytime, son." He told him.

"Yes, anytime you want to visit or are in the area just stop by. We loved having you both around." Claudia told him with a bright grin and hugged Dean tightly before letting him go. Dean stilled for a moment. Unsure what to do before hugging the woman back briefly. Dean felt a warmth his in chest as he looked at Tom and Claudia. He imagined this is what his life would have been like had his mom not died. He was glad he was able to have Claudia treat him like her own son for the past few days. He looked forward to going back to the Stilinski household. Dean said goodbye to them all, waved, and headed towards the car.

Late August 1987

Dean – 8 years old; Sam- 4 years old; Stiles – 3 years old

Dean wasn't exactly sure how he ended up in the store in Beacon Hills with Claudia Stilinski, Sam, and Stiles. But, there they were shopping for school supplies. Sam would be starting kindergarten in a few weeks. Thankfully his dad had enrolled Sam in a school near Bobby's house. It seemed like a good idea. Dean hoped it meant they would get to spend more time with Bobby and perhaps even visit Beacon Hills again. Sam was in heaven it seemed with all the brightly colored school supplies. Even though Stiles wouldn't be attending for another year he happily trailed after Sam up and down the aisles oohing and awing over things.

He chuckled as Sam found a backpack with his favorite cartoon character on it. He was eagerly explaining to Stiles who they were. Dean, himself, lagged behind the pair keeping pace with Claudia. "You really don't have to do this you know." He told the woman once again. Claudia barely knew them yet she treated both he and Sam with such kindness. Dean imagined she was what his mom was like.

When Bobby had shown up at the Stilinski's house a few days prior with the Winchester boys in tow Claudia and Tom hadn't thought anything of it. Instead, they'd set up the guest room and Stiles had been beyond happy to see the older boys once more. Bobby had said he'd only be gone for three days, four at the most. But, to Sam, Dean, and Stiles that was just enough time for some serious fun.

Sam had happily been chatting away to Claudia and Tom about how he was started kindergarten soon and couldn't wait. The school had even sent a list of all the things he needed. Little Sammy even had the list tucked away in his pocket. At seeing it Claudia had announced that the next day they would all go school supply shopping. Which is what lead them to wandering in the store now.

Dean was aware Claudia was using her own money for whatever she bought Sam today. He was a mix of feeling grateful towards her because he knew his dad would probably forget about all of this until the last minute. But, he also felt bad for making her buy them things after all she was already doing for them.

"Dean, I'm happy to do this for Sam. He's so excited about school. Really I don't mind." She told him. "Now… what about you? Do you know what you need for the upcoming school year? Fifth grade is a big year." Claudia continued.

"I'm fine, really. I have my bag from last year and the notebook still has some empty pages. I'm set." Dean told her while shaking his head. He could be ok with her buying stuff for Sammy. His little brother looked so happy. But he couldn't bring himself to allow Claudia to buy him things as well.

"Really, Dean, it is fine. I don't want you to feel left out while Sam gets things." Claudia told him.

"Nah, I don't need anything I'm good." Dean told her earnestly.

Claudia looked at him and around the store, "You sure? A new notebook? Folders? A fun book to read?" She asked him.

Dean bit his lip and looked around the store. He had an internal battle. Dean Winchester was used to giving up getting new things so Sam could. Dean was ok with the second hand clothes from goodwill and reusing what little school materials he had for the next year. But, here was Claudia Stilinski offering to buy him something.

"It would make me feel better if you let me buy you something. Maybe just do it for me then?" Claudia added with a small laugh and smile. Dean was thankful, she was giving him a reason to say yes.

Dean finally nodded and gave her a small grin. "I could use some folders and notebooks… Last year I heard a fifth grader talking about needing folders for all the different subjects." He suggested.

"Folders and notebooks it is! Pick whichever ones you want." Claudia exclaimed and ushered him towards the desired items while keeping an eye on Stiles and Sam who were looking at lunch boxes now.

Dean looked at all the choices he had. Several folders had various cartoon characters and super heroes on the covers. Finally, he settled on getting the plain colored notebooks with a folder to match them. "Very smart. Now you'll know which folder goes with which notebook." Claudia praised him casually and Dean couldn't help the big smile that appeared on his face. "You looking forward to school?" She asked him as they began walking towards the two younger boys. Claudia grabbed the necessary things off of Sam's list as well as some things she knew Dean would need. She imagined he couldn't refuse them once the items were already bought.

"Eh. I guess. It's ok for the most part. Hopefully we will stick around long enough to complete a full year. It's hard for my dad. To stay in one place for a long time because of his work. But, he signed us up at a school near Bobby's house. I think Bobby will let us stay there if dad has to go out of town." Dean rambled to Claudia being mindful to not mention exactly what his father did for a living.

"Well, I'm sure this year will be a great one and staying with Bobby should be fun." Claudia told him after absorbing Dean's words with a small frown. Claudia knew what John Winchester did for a living and that he dragged his kids along with him as he hunted for supernatural creatures. The brunette woman rid her best to not let a sour expression appear on her face at the thought of how Sam and Dean spent their days.

A smile reappeared on her face after a moment as they reached Sam and Stiles. "Now that we have everything we need how about we go find some books for you all to read?" She asked the two younger boys excitedly. Sam and Stiles shouted happily at the idea and ran off towards the books with Stiles leading Sam.

She chuckled at them as once more she and Dean trailed after the two. "I guess they really want to read something." Dean commented lightly as he kept an eye on the pair. "Sammy loves to read. Well, he likes to look at the pictures. I have to read to him still."

"Stiles loves books too. It's the only thing that keeps him still for more than a few minutes." Claudia told him, "Do you like to read Dean?"

Claudia Stilinski didn't think she was a nosey woman. But, something about Dean and Sam Winchester called out to her to make sure the pair were taken care of. Perhaps it was partially due to knowing their mother had died when they were both so young. She hoped, heaven forbid, that if something ever happened to her someone would take care of Stiles for her.

Dean Winchester seemed to always put his little brother first. That was the main characteristic Claudia had noticed about Dean during the short time she had known the Winchesters. That and he didn't know how to accept gifts. From what she had gathered Dean was used to forgoing things in order for Sam to have them. While it was admirable she wanted to try and get the older boy to act like a kid. After all, he was only eight years old.

Dean shrugged a bit, "I don't read much. Usually I just read what Sammy wants me to read to him. Nothing seems too interesting." He commented as they reached the book section where the two younger boys were again eagerly looking through the shelves of books. Stiles pointing to the ones he knew to Sam.

"Momma! Can we get this one?" Stiles ran up to Dean and Claudia holding up a picture book.

"Sure me sweet. We can get that one." Claudia told him with a light laugh at his excitement then ruffled Stiles' hair. "Sam did you find one you liked?" She asked the other boy who stood sheepishly off to the side with a book in his hand.

Sam nodded and held out a book. "Can I get this one?" He asked.

Claudia nodded and gave him a sweet smile. "Of course you can, Sam." Sam smiled brightly at her. Claudia looked around the bookshelves and pulled three books off the bookshelf. "Here, Dean. I remember reading these when I was younger. I think you'd like them." She told him.

Dean was startled as Claudia handed him some books. He read the title, 'The Boxcar Children'. He automatically wanted to say she didn't have to buy those for him but the brunette woman was already leading Sam and Stiles back towards the front of the store.

"They are a gift, Dean. Don't try and put them back. Come on, now. I think we have time to get some ice cream." She said giving the eldest boy a knowing look. Dean nodded and walked until he was back in step with her, hands clutching the books carefully. Claudia patted his back briefly as they went to the checkout counter. Claudia had Dean take the boys ahead to the car while she paid.

Dean never did find out how much she had spent on them. But, as he sat down in the living room of the Stilinski household looking at the things he got, as well as the look on Sammy's face, he realized it was ok to be happy and not feel guilt about receiving these things.

Dean spent the remaining days at the Stilinski house reading the first Boxcar Children book aloud to Sam and Stiles. He was surprised by the fact that he enjoyed the story so much. The two younger boys seemed to enjoy the story as well. Each boy sat with undivided attention as they listened to Dean read to them.

When Bobby showed up once more the Winchesters and Stilinskis said their goodbyes, yet again with the promise of seeing each other soon.