Title: I'll show you how to do it
Fandoms: Supernatural
Characters: Dean, Sam
Genre: Humor
Prompt: An old ruin is the location, insecurity is the theme. A desk is an object that plays a part in the story.
Join my writing game here
The light of the flashlight trembled. Dean hit it with his hand and the light beam stabilized, then he pointed it while looking around in that empty room. "I've always hated school," he said. "And this creepy place isn't helping."
"You didn't hate school," Sam said, behind him. "You had fun, admit it."
Dean frowned. "The only funny thing was the broom closet, where I could make out with girls," he replied, then sighed. "Those were the good times. I haven't kissed somebody since a long time… ugh!".
"You can kiss anyone you like, you know that," Sam replied, looking into a metal closet.
Dean turned towards him, confused. "W-what?".
Sam looked at him. "You know what I'm talking about." Dean still looked confused. "Cas," he explained.
"Why in the world are you talking about Cas?", Dean exclaimed.
Sam sighed. "Look, I know it's been tough for you, but you have to figure it out! Every time you look at each other, it's like you want to rip your clothes off. It's becoming… uncomfortable."
Dean was still staring at him, squinting.
"Let's do this," Sam said, approaching. "Just pretend I'm Cas and ask me out for a date."
Dean sighed as he looked at his brother. "I can't do that," he said.
Sam took a look around, looking for the blackboard, but he didn't see it. There was almost nothing in that room. It wouldn't have taken long for that school to just collapse on itself. That building was just an old ruin. The only thing he found was the teacher's desk. He took it and leaned it vertically on the wall. He found a marker on the ground and drew a big stickman on the top of the desk. He added a pair of big eyes, dark hair, and drew some kind of clothing on his body.
"Is that a… trench coat?" Dean asked, pointing his flashlight towards Sam's drawing.
When Sam finished, he pointed at the desk. "Just pretend this is Cas. Now go, Dean."
Dean stared at that horrible stickman. "I-I don't know, man," he stammered. "What if he doesn't like me in that way?"
Sam shrugged. "You will never know if you don't try."
Dean approached to the desk, trying to see that horrid stickman as the real Cas. He smiled, embarrassed, while his brother stared at him.
Sam couldn't bear it no longer. "I'll show you how to do it," said, before taking Dean's face with both hands and placing an open kiss on his lips.
So, okay. I want to say that I don't ship wincest, so I don't know how this thing came out of my mind, but I couldn't help myself. And yeah, the thing of Sam looking into the closet is deliberate. Like "coming out of the closet" and all that stuff. Maybe Sam was looking for Dean's heterosexuality and of course he didn't find it.