This is pretty dialogue heavy, fair warning.
I literally paused the show after Dean said that line so I could write these, so you gotta give me something for not procrastinating. There will be two takes of this, one where Sam comes clean to Dean, and the other where Dean walks in on him. Oh dear, let's see where this goes. No Wincest, cause I haven't seen enough to do it right. I'm only on the second season, so please forgive me if I do something wrong.
The places I mention are real; I go there all the time in the summer, even Headwater's, no matter how ironic it is. I was tempted to change it, but it isn't that important and maybe the irony works? Maybe? Boulder Junction the only remote location I'm familiar with they could actually go to. So try to enjoy? :D
I know this might make Sam a total loser, but this could have happened at least once.
"Thanks for stopping by, boys." The pretty blonde waitress, Samantha, placed her hand on Sam's shoulder, giving him a quick wink. Sam smiled and blushed, he occupied himself with the bill.
He noticed her right as the two brothers entered Headwater's Diner in Boulder Junction, Wisconsin. The pair was investigating the possibility of an angry spirit by some the old backroads. Two people driven off the road in the middle of the day, right into Boulder Lake.
Sam found her appealing, and tried to strike up a conversation as she led him and Dean to their table, the latter giving his brother quizzical glances.
They gave her their drink order, and she left them.
"You think she's cute." Dean gave a jesting smile and smacked his brother's shoulder.
Cute, but not enough to meet Dean's standards.
"Shut up, I like her… hair." Dean smirked.
"Into blondes. Nice."
The waitress came with their drinks, set them down and sat at the neighboring table. It was close to closing and they were the only ones in there.
"Thanks, Jane." Sam read her brass nametag.
"Actually it's Samantha. I'm the newest hire and they didn't bother to make me a nametag. Anyway, what brings two guys as handsome as you," she tapped Dean's shoulder, "into a town like this?"
"We're counselors at the camp down the road. I'm the archery teacher; Sammy here is in charge of Arts and Crafts."
"No I'm actually not." He scoffed it off.
"No shame, boys. I'm just a waitress. Those kids at the camp spend more for a month than I make in a year. I should work there. Maybe then I could finish paying for school before I turn fifty."
"What's your major?" Sam was intrigued. Basically any girl going through college was a desirable one.
"Pre-law at UW- Madison."
"Same with Sam here, except Stanford. Free ride." Dean teased.
"Stanford? Very nice. I'm jealous. I had to work my butt off to get into Madison, but you free to Stanford? Impressive." Sam was impressed. A good looking girl with a good head on her shoulders, now that is attractive. Sam could feel himself blush.
They continued chatting while they ate, Dean historically unimpressed, but Sam was being kept entertained.
Dean sent her for the check, and took advantage of her absence.
"Dude, give her your number."
"She's into you."
"No she isn't."
"She's blonde and smart, I promise you are never going to do any better. She's like girl you, her name brains, all that jazz. Other than the looks of course."
"I thought you thought otherwise." Samantha came from around the corner to find the Winchester boys look like deer in a headlight.
"Yeah, thanks so much." Sam paid quickly and saw no phone number, nor left his.
"Thanks for stopping by, boys."
The guys left the diner and went to their car, and drove to their hotel.
The hotel was overbooked, and the only room available was a two-bedroom suite, instead of their usual motel room. The owner gave them the room for cheap.
They made it back, bypassing the haunted road, and dumped all their gear on the couch in the main room.
Dean made straight for the shower, leaving Sam his choice of bed. The one in the studio, or the one with the door.
Door, naturally. It would be nice to not have Dean panic over him if he had one of his vision nightmares.
He grabbed his laptop and settled in to research the road.
He learned that a car went off the road in the seventies, and into the lake. Right into a canoe full of campers. Freak indeed. It must be the kid's spirit's drowning the drivers.
From the camp that Samantha mentioned.
He should have given her his number. Maybe then Dean would get off his back about never getting laid.
So he did the only viable thing a guy alone in a hotel room would do; take off his pants and pull up Google.
Dean had a thing for showers.
Every place they went to, he would compare and contrast the quality of the shower of the last place they stayed at.
This was not one of the better ones. Regardless, it was still nice to let the heat wash away the stiffness from their drive.
He stepped out, and wrapped a towel around his waist. He was still shaking his hair out as he walked from the bathroom, where he found Sam sitting on his bed, face deathly white and as though he had just seen a ghost.
"What'd they do to you?" Sam looked up then dropped his head, blushing.
Dean went through his bag, finding clothes. Sam was still silent.
"I'm a horrible person."
"For disappointing me, your family, and that waitress for not giving her your number? Yes, yes you are." Dean laughed and threw a sock at Sam.
"What did you do?"
"I should be in jail."
"For not giving her your number? You were a baby, that isn't a criminal offense."
"No, for – uh something else."
Dean disappeared for a second to go dress.
"What? Seriously just spit it out." He moved to the weapons bag and began pulling them for cleaning.
"You can tell me, Sam. It can't be that bad."
"I'm a pervert." Dean stopped and looked up. When he saw his brother was serious, he laughed.
"How, Sammy?" Still laughing.
"I can't tell you. It isn't something people talk about."
"What makes you say that? Cause from what I'm hearing, and that is only 'pervert' and 'taboo', I'm drawing some conclusions. Just say it. I've probably done worse."
"I know you have."
"This is getting ridiculous. Just say it or get off my bed."
"iwishedpen." Sam spoke fast and incoherently.
Sam rolled his eyes and exasperatedly coughed out his sentence. "I watch-watched," He put his hands up. "I can't."
Dean knew. He was internally dying. His poor innocent brother, how did Jessica manage?
"What did you watch?" He feigned ignorance.
"Dammit Dean, I watched College Babes 4 and went through the entire gallery from the wet T-shirt world championship contest."
"Eh… porn?" Dean started laughing again when Sam put his head in his hands.
"Yes, yes okay, I'm sorry. I know it's bad but I should've given Samantha my number. I couldn't help it, I thought about her. I'm a disgusting human, I'm a pervert. I need to go apologize."
"Apologize? Are you serious? What are you, twelve? You didn't feel so bad when that bitch called you a pervert for watching Meg dress in her window. What's with this?"
"I'm not you, Dean. I have standards." True, but not is not the time for that.
"Dude, it's not a big deal. If you want a case where I was worse than you, I would be happy to share. Now that, dear brother, is being perverted." Sam stood. He would not hear this.
"I still feel bad."
"Go be a pissy, self-righteous kid in your room then. I've got to get these clean. And seriously, who doesn't talk about this? Dude, you need to get out more."
Sam stood to go back to his room, fully embarrassed now. Dean was not the person to be talking about things with.
The door was almost fully shut when Dean called after him, "Was it at least good?"
Sam grabbed the nearest thing to him, a pillow, threw the door open and hurled it at Dean, who was laughing as he swatted it away.
I didn't even consider the Sam/Samantha name similarity until over halfway through. I hope this turned out alright.