Suggested by: PrincessPeach211
Shit, Dean thought to himself. This can't be happening, not now. He blinked and rubbed his eyes, hoping the pregnancy test would turn negative. It didn't. He didn't know what to do. He was already struggling with his gender identity, and now he was pregnant. John was going to kill him. Dean hadn't even told him about his current struggle, and now this...
Dean thought about it for a few days and finally decided he would run away. It would be better for him, anyway. John sucked as a father, and Dean had enough. The only problem he would have is breaking the news to Sammy. He just knew he had to do everything as soon as possible. Luckily for Dean, John was going out on a hunt this week, and Dean casually asked to stay behind, just to watch over Sam. Giving a skeptical look, John agreed. He wasn't sure why Dean suddenly wanted to watch over Sam; the boy had been staying on his own for a few years now, when Dean and John would go hunting together.
On the morning that John was leaving, the two boys waved goodbye to their father, wishing him a safe trip and good luck.
"I don't need luck, that son of a bitch is gonna need luck," John sneered. He got into a car he'd hot wired, leaving the Impala at the motel with Dean, just in case. Dean shut the door when he heard the car drive away.
"Okay, Sammy, I have something to tell you," Dean said, turning to his younger brother.
"What's wrong, Dean?" Sam asked, sensing that something was wrong.
Dean sighed, "Look, I don't know who I want to be. I know I was born a guy, but I kinda feel like I should've been a chick, ya know what I mean?"
Sam shrugged, "Okay."
"Woah, hold up, there's more. Sammy, I—uh, I found out I'm pregnant a few days ago."
Sam's eyes widened, "Oh... You know dad's going to kill you, right?"
"Yeah, I know. That's why I have to get outta here."
"You mean you're going to leave?"
Dean gave Sam a sad smile, "Yeah, I'm gonna leave."
"Please, Dean! Don't leave me here. You know that Dad and I don't get along. I can't do this, not without you to break us up. Please, please, please let me come with you!" The boy begged in a panic.
"Woah, woah, woah, calm down Sammy." Dean put his arms around Sam while he thought for a minute. "Fine, you can come." Secretly, he was happy he wasn't going to be on his own, and really didn't want to leave Sam with their father by himself. "Start packing. We leave as soon as we can."
They were a couple states away, finally far enough away from where their Dad was living currently, when Dean saw a "Now Hiring" sign in the window of a diner. He smiled to himself and stopped at the nearest motel.
Dean walked into the office and requested a two bed room for an indefinite amount of time.
"Okay, Sammy, I need you to stay here for a while. I saw a diner down the road that I'm going to try and get hired at."
"You're going to get an honest job?" Sam laughed.
"Yeah, shut up nerd," Dean said, smiling and playfully punching Sam.
Dean dug around in his suitcase and pulled out a black and red frilly dress. Sam's eyes widened.
"What the hell?" Sam asked.
"This is what I told you about earlier. I kinda feel like I'm supposed to be a chick, and this is a good time to try out Deanna. A girl is more likely to be hired at this kind of diner."
"Well, good luck," Sam said, as Dean went into the bathroom to change.
When Dean came out, Sam was again surprised, "Actually you make a pretty good chick."
"Shut up," Dean rolled his eyes, but smiled to himself.
A while later, Dean came back, announcing he got the job.
"How did you manage that?"
"Faked it. I take orders and make coffee. That's basically all there is to it."
Sam sighed, "So we're actually going to have money?"
Dean shrugged, "Some."
"Well, you're already giving us a better life than Dad ever did."
"That's all I want."
