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Let Me Be Your Wing Man

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Dean smiled to himself as he drove down the road. Sure, dad was missing and that was of the most import, but there was nothing he could do while driving. Instead, he decided he’d play twenty questions with Sammy. Starting with the smoking hot girlfriend he was living with.

“So… Jessica, huh?” he smirked and turned towards his brother.

“What about Jessica?”

Ah, so little brother was going to play it close to the chest. Alright. He could work with that. “You know… your girlfriend?”

He watched Sam out of the corner of his eye as he saw the eye roll. “She’s not my girlfriend.”

“Not your – why the hell not?!” He was so shocked he gunned the gas a bit. Catching himself, he slowed and looked quickly over at his brother.

“She’s really not my type.”

“Not your type? What is your type then? Misguided co-eds with daddy issues?” He still couldn’t wrap his head around the fact that Sam would pass up an opportunity to hook up with a girl that looked that good.

He felt Sam’s eyes on him before he spoke. “Ok, one, that’s mean. Two, no, that’s not my type either.”

He had a feeling his brother was hiding something from him. Maybe he had a girlfriend he was embarrassed of or something. But, then again, Sam would never do that… he was too nice. “Well, then, Jess available?”


The tone was so harsh Dean was taken aback. “Why not? Don’t trust your brother or something?”

“Hit it right on the head.”

“Seriously, man, you diss your own brother? Your flesh and blood?”

Sam sighed. “Jess is a really good friend of mine. She actually is dating someone, but even if she weren’t… Dean, you don’t stay in one place for more than a week, if that. I’m not introducing you to someone so special to me for a one night stand.”

He shrugged to himself. “Ok. Fair point there. So, if Jess isn’t your type, then what is? I mean… we gotta find you some action.”

“I can find myself my own action, thank you very much, but since you asked so nicely… they have to be tall.”

“Tall. Ok. That makes sense since you’ve grown up to be a giant. What else?”

“Shorter hair. Preferably shorter than mine.”

Dean scrunched his face up “Shorter than yours?” he pondered “well… ok. Pixie cuts are kinda cute. So we got a tall girl with a pixie haircut. That definitely limits the pool, but I’m sure there’s enough out there for us to choose from.”

“Dean, ‘we’ are not finding me someone to date. I told you, I can do that on my own. Plus they have to be a little… muscular.”

That threw him for a loop. Now Sam was just being ridiculous. “You’re not talking body builder type, are you? Because if you are, I’m no longer related to you.”

He heard Sam laugh. “No. Absolutely not.”

“Alright. So, we're talking obviously goes to the gym, but not like, hardcore?”

“Yeah. Yeah you could say that.”

Dean smirked. He now knew what kind of girl to look for while they were on the road. Sam may say he didn’t need any help, but he was sure he could find the perfect girl for him.

“There’s one more thing.”

“Seriously?! Dude, your down to 1 in, like, 10,000 right now.”

“They um… have to have a penis.”

Dean slammed on the brakes and whipped his head around to stare at Sam. “What?!”

“I’m… gay.”

“Are you dating anyone?”

“What? No…”

“But, you know, you’d tell me if you were, right?” Dean continued to stare at his brother.

“Yeah, I… I guess so.” He watched as Sam started to really get confused.

“Good.” He lifted his foot off the brake and started putting pressure on the gas again until they were going the same speed they were before.

“Dean, I –“

“Cause, you know, if you were, I’d have to check him out. Make sure he was good enough for you. Make sure he’s not crazy. Shit like that.”

“Um… ok?”

“After all, I am your big brother. I mean, I could even be your wing man if –“

“Stop. No. Never. You will never be my wing man.”

Dean was offended. “And why the hell not?!”

“Dean… and don’t let this get to your ego… lord knows you don’t need it… but you ooze sex. I mean, every girl when you were in high school… they were all after you. You come into a gay bar with me and I become invisible.”

“I ooze sex, do I?” Dean smirked and wiggled his eyebrows.

“I told you not to let—“

“Then you shouldn’t have said it. Man… oozing sex. Love it, man.” He smirked and could practically feel Sam roll his eyes.

“So… I’m guessing you’re ok with this?” Sam asked tentatively.

“What? You being gay? Of course. After all, it just means more chicks for me.”