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I Believe In Myself

Summary:

Dean, Sam, Eileen, Charlie, and Dorothy go out for drinks one night. As the fifth-wheel, Dean is feeling a bit left out so he declares he is going to find a hook up.

@TFLN (305): "Listen. I haven't sucked a dick in well over three years but I believe in myself."

Notes:

My first multi-chapter fic. Explicit rating is for later chapters. More tags coming soon.

Chapter Text

Dean is already a couple beers in and they haven’t even left yet. But why not? He's had a rough week at the shop. The customers are more demanding than usual saying they could do a better job than him. If you think that then go for it! If they know so much about cars why even take it to a mechanic?! He likes his job, but sometimes the customers are just too much.

Cracking open another beer Dean sighs as he heads into his room to decide what to wear. He doesn’t want to be a girl about tonight, but a night out with his brother, his best friend, and their girlfriends is sure to be a trying night. It's times like these that he wishes he had a partner. He's not all that into fifth wheeling. But tonight he wants to go out, drink, and maybe take out some of his frustration with an interested party. To do that he has to look good..better than his normal good. With his built body, striking green eyes, and honey brown hair, he knows he's attractive. He’s not being conceited, people tell him he's good looking all the time. All he needs tonight is to perfect the wrapping on the package.

He grins to himself as he has that last thought, reaching into his underwear drawer and pulling out his favorite pair of pink satin panties. Yes, these will do nicely as “wrapping on his package”. He’ll wear them underneath his best pair of boot cut jeans, the ones that show off his ass. Along with a tight black t-shirt, green and black flannel over that, and black boots, he has crafted, in his opinion, the perfect outfit. Downing the rest of the beer, Dean heads into the shower, whistling a happy little tune.

Forty-five minutes later Dean is washed and dressed. Stopping to put on some cologne, Dean hears voices in the living room. “Sam? Is that you?” Dean calls out as he walks out of his room and down the short hall. “Hey Moose! When did you get here?”

“I came in about ten minutes ago. I said hi, but I don’t think you heard me over your rendition of a Taylor Swift montage.”

“You’re just jealous of my amazing voice.” Dean huffs back. “Hi Eileen.” He signs, looking over at his brother’s girlfriend so she can read his lips while he speaks.

“Hi, I’m sure your voice is lovely.” Eileen signs back before going over and giving Dean a big hug.

“When ya gonna leave this big lout and run away with me?”

“Just say the word Dean and I’m all yours.” is her laughing response.

“If you’re done trying to steal my girlfriend, we should head out. Charlie and Dorothy are meeting us there right?”

“Yea. They said they’d find a table for us all. You’re driving by the way.” Sam raises his eyebrows at this statement. Dean always prefers to do the driving himself and he absolutely hates Sam’s Prius. “I’ve had a long week. I plan on doing a lot of drinking and hopefully I won’t be going home alone.”

“Well at least you’re being slightly responsible...at least about the driving.” Sam replies while rolling his eyes. “How many beers have you had already?” Eyeing the counter and the cans there.

“Just enough. I need to pregame you know. Let’s go.”