Just Walk On By, College Boy (But You Never Did Make Good Choices)
Dean adjusted his leather jacket as he walked down Main Street towards the corner store. He needed some cereal or some other passably edible food stuff for his dorm before he died of hunger. He passed the local park on the way there and pretty as it was, there was a much more exciting sight on his journey. A Catholic private school. Plenty of girls in those plaid skirts and high socks. Dean had a deep appreciation for schools like that.
He grabbed some food and made his way back to campus, passing the school again. The students were just being released for the afternoon so Dean decided to do a bit of loitering and people watching. The uniforms were just what he was hoping for, but it wasn’t the girls who ended up truly catching his wandering eye. It was a boy, no more than three years younger than Dean himself, walking out of the school with his eyes glued to the pavement and a tan trench coat pulled tight around his uniform. Dean smirked and snorted a bit. The kid looked like the height of innocence, like he belonged at a Catholic private school, unlike the girls who pulled their skirts up so high you could see their panties. The boy heard Dean and looked up, blue eyes wide.
And weren’t those just the bluest baby blues Dean ever did see.
“Hey kid,” Dean ventured.
“He-hello.”
“I’m Dean, nice to meet you,” Dean continued, bold as ever.
“I am Castiel.”
“Well ain’t that a mouth full. Do your friends just call you Cas?”
Castiel titled his head to the side and peered at Dean, confusion plain on his features.
“…Cas it is. So Cas, ever been in a college dorm room before?”
Turns out he hadn’t been in one before and he was a curious kid. Dean had definitely picked a winner with this one. He wrapped his hand around Castiel’s, pulling him gently in the direction of the campus. Back in Dean’s dorm Cas got a quick tour (not much to look at in a small room like that) and was promptly sat down on Dean’s bed for a little chat.
“So, Cas. How old are you?”
“17.”
“And when will you be 18?”
“The end of next month.”
Dean smirked and patted Cas’ hand. He could wait.
A month of picking Cas up after school and the kid finally turned 18. They were making out on Dean’s bed, as they had for the past 3 weeks of their little relationship-esque thing and Dean got an idea.
“Cas,” Dean panted against the younger boy’s mouth. “Can I try something?”
“Y-yes, Dean,” Castiel stuttered out.
Dean slipped his hand from where it was carded in Cas’ black hair.
Skipping over the white button down and the blazer layered over it, Dean let his hand come to rest on Castiel’s belt buckle.
“Is this okay, Cas?”
The younger boy nodded after a split second hesitation and Dean undid the belt with practiced precision. Cas gasped and Dean paused, but the younger boy just nodded again, giving his consent. Dean threw the belt to the floor and slipped the button fly open, unzipping the slacks as well. He teased above the waist band of Cas’ underwear before working a hand inside them. Cas bucked off the bed at the first skin on skin contact and moaned quietly.
“You like that, Cas?”
“Yes, Dean,” Castiel said, voice breaking slightly when he uttered Dean’s name.
Dean grinned and built up a rhythm, enjoying the way Cas shuddered and moaned with each stroke. Dean let his thumb slide over the head on the next upstroke, eliciting the loudest groan yet from the boy underneath him.
“More, Dean. Please.”
Dean sped up his hand and pressed his lips to Castiel’s. He moaned into Dean’s mouth and came, hips stuttering and stilling. Cas panted and gasped as Dean slid his hands out of the black slacks, fingers scrambling to tangle in Dean’s t-shirt and pull him down for a kiss.
“Whoa, Cas,” Dean said with a smile, kissing the boy.
“I enjoyed that, Dean. Thank you,” Castiel said matter of factly, like this was a business deal and he had come out on top.
Dean kissed him again, smiling fondly at the way Cas talked about sex, and settled down next to him, slinging an arm across Cas’ chest.
“I really like you, Dean,” Cas said after a few minutes of silence.
“I really like you too, Cas.”