April, 1941

He forgot how to breath. He was lost in thought. Only snapping to reality when Sam clapped him on the back. "Ready?" He asked. He looked at him for a second, then nodded. Pushing open the door of the recruitment office, he exhaled. There were different offices for every branch. Including the national guard. "I'll be waiting out here." Sam sat down in a chair and picked up a magazine. Dean walked in to the Army office. The recruiter looked up from his computer and stood up. Dean stood in the doorway for a moment. "We talked on the phone yesterday. My name is Dean Winchester."

"Yes, I remember. Have a seat." He did as he was told. "Alright Winchester. You said you want to be a paratrooper, correct? " Dean swallowed. "Yes sir."

"How old are you Dean?"

"Twenty-one sir."

"Graduate high school?"

"Yes sir. Top twenty."

"College?"

Yes sir. For two semesters."

"What did you study?"

"Photography sir."

The recruiter looked at him, eyebrows raised. Dean shrugged. "You ever shoot a gun before son?" Dean almost laughed. "Yes sir. I know my way around almost any weapon you put in front of me." The recruiter laughed.

The interview went on longer than expected. When Dean walked out of the office, Sam stood up. Dean stopped in front of him. "June. I leave for training in June. I'll come back in around mid November. Then I wait for my orders. If I make it through training." Sam smiled. "You'll make it. Dad did." Their dad was a WWI veteran. He didn't talk much about the war. Hell, he didn't talk much at all after he got home.

Dean climbed out of his 1935 Chevrolet Coupe and sighed. He didn't know how his dad would take the news of his enlistment. He walked up the stairs, putting out his cigarette before opening the front door. The smell of cigars and liquor hit him. "Dad? I'm back." The place was a mess. "Back here." He heard from the kitchen. He walked slowly through the house. Standing in the doorway of the kitchen, he saw his dad cooking lunch. "Hungry?" He asked. Dean nodded, putting his hands in his pocket. "Where you been?" Not looking up from the carrot he was cutting. "Enlistment office." His dad stopped. He slowly looked up at Dean. "Why?" Dean though for a moment. "I don't want to work on cars the rest of my life."

Suddenly, his dad smiled. He walked around the counter and pulled Dean into a hug. "I'm proud of you son. Doing something with your life." Dean hugged him back. "Thanks dad."

June 1941

The short time before training, Dean spent as much time as he could with Sam and his dad. It was the most John Winchester had spoken in years. He was truly proud of Dean. He would boast that his eldest joined the Army to everyone he knew. The night before Dean's departure, John had taken Dean, Sam, and Sam's girl Jess out to eat. They laughed and talked for what felt like hours. When a few family friends showed up, John grabbed Dean's camera and handed it to the waiter telling him to take a picture of all of them. Bobby, Ellen, and Jo, protested at first but Dean insisted. They couldn't say no. When the picture came out, John gave it a few shakes and looked at it. "Oh that's good." He handed it to Dean. "You keep it. I know it only training, but it'll be rough. You'll miss home. And when you do, just look at this." He grabbed his glass of whiskey. "A toast!" He raised his glass. Everyone followed suit. "To Dean. My eldest son. For not wanting to work on cars your whole damn life. I'm proud of you son."

"To Dean!" Everyone chimed raising their glasses. Dean raised his bottle of beer at them, smiling. "Thank you everyone. Really. It means a lot that you're here and you're gonna see me off in the morning." He put the bottle to his lips and drained the rest of his beer. "And now...I gotta get some sleep." He hugged everyone and thanked them. He clapped his dad on the shoulder and told everyone goodnight.

He woke up the next morning early to finish packing. Putting on his uniform, he grabbed the picture from last night and put it in his pocket. The only thing left was to head to the train station and say goodbye to his family. He parked his car behind his dad's shop. Grabbing his bag, he shut the door and walked around to the front. His dad was already waiting. Dean handed him his camera so he could take a picture of Dean in his uniform. John put it on the dash of his car as they both climbed in. It was a silent ride to the station. When they arrived, everyone was waiting. They all talked for a few minutes til the conductor yelled for boarding. Ellen and Jo both said tearful goodbyes. Jess was fighting back tears and Sam hugged him tightly. Bobby patted him on the back saying "see ya kid." He turned to John. He had tears in his eyes. "Your mother would be proud of you Dean." Dean smiled. Knowing if she was here she would say so herself. John pulled him into a hug. "Stay safe. Be the best one there." He told his eldest pulling away. Dean smiled. "Yes sir." The whistle blew and Dean picked up his bag. "Well, see y'all in a few months."

On the train, he picked a window seat. He opened the window and leaned out as the train began to move. "Take care of my car!" He yelled. They all laughed waving. The train picked up speed. "I'll be back before you realize I'm gone!" He yelled waving. He waved til they were out of sight.

From the train to a bus. A bus full of recruits like him. Some engineers, some medical, infantry, and paratroopers. One paratrooper named Adam, sat next to Dean. He was younger. Nineteen. Same age as Sam, and also fresh out of high school. "Almost every man in the family has been in the military." He told Dean. "What about you?" Dean looked at him. "My dad. Army. WWI."

The bus came to a halt and instructors stormed it. Yelling at everyone to get off. When Dean stepped off the bus, their stuff was already thrown everywhere. Dean, Adam, and a few others already standing at attention. "Well I can tell who comes from military families." One said. He walked up to Dean stopping an inch from his face. "What's your name son?"

"Winchester sir."

"What are you here for Winchester?"

"Paratrooper sir."

"Very honorable son."

"Thank you sir."

"Your daddy a trooper?"

"No sir. Infantry. 22nd. WWI sir."

"Wait a second, Winchester. Your daddy John Winchester?"

"Yes sir."

"Well hell boy, your dad's a fuckin' hero son! Good man." He looked over his shoulder. "Put Winchester in the 101st." He turned back to Dean. "Grab your bags kid. You're with me."

His days were filled with marching, weapons training, physically training, and parachute safety training. They didn't get to actually jump out of planes until the second month. Dean passed everything with flying colors. Then came the mission training. They had to jump out of a plane, find cover under fire, and provide back up to an infantry unit that had been pinned down by the enemy. They weren't firing live rounds, though the blanks hurt like a bitch. Sargent said Dean was a natural like his dad. Dean and Adam became good friends. Dean would always help Adam and thought of him as his little brother. Always making sure he rigged up properly. Dean had also become the platoon leader by unanimous decision. There was no denying he was the best. He graduated top of the class and was promoted to private first class. He couldn't wait to get home.

November 1941

The train came to a stop. He grabbed his bags from over head and stepped off the train. Looking around, he saw Sam towering over the crowd. Pointing at Dean. He smiled and shook his head. "Damn kid just keep growing." Just as everyone got to him, he heard a voice behind him. "Dean!" He turned to see Adam hanging out of the window. "I'll see ya man!" He waved. Dean smiled. "Take care little brother!" He waved back. He turned to his family and friends. They all hugged him at the same time. "Come on guys. Get off." He laughed. In the back of the crowd was John. Dean walked to him. John smiled and gave his son a hug. "Welcome home Dean. Let me look at ya." He looked Dean from head to toe. "Promoted to PFC." He beamed. Dean nodded. "Top of the class. The best. Just like you asked sir." John pulled him into another hug. Saying how proud he was. Dean knew he would boast even more about how his son was top of the class and promoted. "So how was it?" Sam asked. Dean smiled. "First I need a damn burger. The food there sucked." They all laughed.

That night they went to Dean's favorite burger joint. He was grateful to be in regular clothes after wearing a uniform for four months. He told them everything. About training, about the platoon and how they would get rowdy at times, about Adam. He heard the bell chime as someone walked in. He looked up to see a man with dark hair and gorgeous blue eyes. Dean's whole world seemed to stop. The man only ordered coffee and walked out. Dean grabbed his leather jacket and stood up. "Smoke break." He explained. Lightning his cigarette, he looked at the man who now had a map open. "Lost?" Dean asked. The man turned and Dean's breath caught. He was absolutely beautiful. "You could say that. I was just passing through and got turned around." Dean walked closer. The November air made his breath visible with a cloud. "Where ya headin?"

"Anywhere."

"That's pretty vague."

He offered his hand. "Names Dean."

"Castiel. Call me Cas."

"Well Cas, you just gonna point to a destination on that?"

"Pretty much. I'm traveling the country."

Dean nodded, flicking the ashes of his cigarette. He pulled the pack out and offered one to Cas. He took one and Dean lit it for him. "Thanks."

"You hungry? We ordered plenty of food."

"Looks like you're celebrating something. I don't want to intrude."

"Nah, just my homecoming. Just got back from training. Army."

"Oh, well congratulations."

"It's no big deal. My family thinks it is. Come eat. I'll point you in the direction of a hotel after."

"That would be great, thanks."

After everyone was full and Dean ran out of stories, they decided to call it a night. Dean was the last to leave. He shrugged into his favorite leather jacket as he stepped out of the diner. Cas was standing there looking at his car. He turned to Dean. "Yours?" Dean pulled a cigarette out and lit it. "Yeah. High school graduation present from my dad." Cas nodded. "Well, thanks for the food." He turned to walk away. "Hey!" Dean called after him. "Can I give you a ride somewhere or something? A hotel? If you want to save money, my couch is free." Cas turned. "Offering a stranger cigarettes, food, and I ride. Not planning to kill me are you Dean?" The way he said Dean's name sent a chill up his spine. Cas closed the gap between them an inch away from Dean's face. "Or...are you queer?" Dean swallowed. He laughed and shook his head. "Well, I offered." He started for his car. Cas followed and stood at the passenger side. Dean looked up at him. "Hey, you offered." Dean shook his head and got in. Opening the passenger door for Cas. He climbed in and Dean started the car. "Where to?" Dean asked. Cas thought for a moment. "Your couch is free?" He asked in reply. Dean nodded. "Free it is then."