This is basically a study of Dean and why his bisexuality shoved so damn far back in the closet. Seriously, it is buried under leather jackets and blue jeans. Here's hoping I got the timeline right as far as Canon goes.
Dean was twelve years old the first time he kissed a boy. His name was Nate McAvery and they kissed behind a boarded up gas station in Brooklyn, in October 1991. Nate's lips were chapped and he tasted like pilfered cigarettes but he didn't sock Dean in jaw afterwards. Instead, he blushed something hardcore and asked Dean why he did it. Dean didn't have any better answer than "felt like it" and Nate kissed him back.
Dean couldn't explain why he liked Nate so much. Maybe because they had the same taste in music and cars or maybe because Nate had spiky black hair, too long in the back. He was the hottest boy Dean had ever seen. Dean didn't usually notice boys, at least not as much as he noticed the girls. He liked girls in a different ways, because they were soft and smelled good. They yielded gently and blushed when he stole kisses. Kissing Nate was like getting into a fight after school. They pushed hard into each other's lips, daring the other to back down first and Dean loved it. He loved kissing Nate, holding his hand as they ran through the city, sneaking secret glances in shop class for a week.
They were in Dean's hotel room, watching the Adult movie channel that Dean managed to descramble. Sammy was eight and unable to appreciate the older boys' taste. He'd taken refuge out on the balcony. Dean was only half watching anyway as Nate climbed up next to him on the bet and begun making out with him. Dean didn't mind. In fact he was ecstatic. Between Nate's tongue and Jenna Jemmison's bouncing breasts, all he needed was a Zepplin soundtrack to convince himself he'd landed in heaven.
He should have known it couldn't last. The door slammed with a loud crack as John Winchester barreled into the hotel room, pinning Nate down to the bed and shoving Dean into the wall. Dean gasped, trying to rationalize whatever was happening, while his father pressed his pistol to Nate's head.
"Whatever deal you made, call it off now, you son of a bitch!" John growled dangerously. "I don't know how you got in here but you're not getting out!"
Nate sobbed with terror, wildly glancing around for help. It took Dean a moment to register what his father was thinking.
"Dad!" He shouted. "It's okay!"
"Shut up, boy!" His father glared at him, angrier than Dean had ever seen him. Dean swallowed hard, fighting the urge to keep his mouth shut and obey.
"Dad, he's not a demon!" He said, trying to pull his father off the shaking twelve year old. John glanced at him, than back at Nate, rage fading into confusion. "Please, Dad, let him go!" Dean begged.
Begrudgingly, John let Nate go. The black haired boy lay shaking against the headboard, too scared to move. Dean sighed. At least, no one got shot.
"Get out." John ordered, pointing at the door. "Go home!"
Nate didn't need telling twice. He scrambled off the bed, grabbed his backpack and took off running. Dean watched him go, a dark pit growing inside his stomach. Nate would probably hate him now. He turned back to John, staring him up and down.
"Did you make any deals?" He demanded.
"He wasn't a demon, Dad." Dean protested. "I checked him with holy water, there's salt on all the doors-"
"Did you make any deals?!" John shouted.
"No!" Dean said. He wasn't stupid, after all. He'd just wanted to kiss a boy.
John sat down on the bed, rubbing his eyes with on hand. The pistol was still tight in the other. He'd been hunting a wendigo. Dean knew it was filled with rock salt bullets. His father sighed.
"Dean," John said. "Don't you ever scare me like that again, boy."
Dean nodded, staring down at the floor, ashamed. "Yes, sir."
"I'm serious. If I catch you pulling anything like that again, I'll gank you myself." John stared at him intently. "You get me, boy?"
"He wasn't a demon." Dean offered weakly. "He was just a kid from school. Just a normal kid…"
"I said, do you get me?" John asked again, his anger resurfacing.
Dean nodded, "Yes, sir."
"Don't know what passes for normal these days." John muttered. "Where's your brother?"
Dean pointed to the balcony. He wondered how much Sammy had heard. The walls were thin and John yelled loud.
"Jesus." John shook his head and called to the balcony. "Sammy, get in here! Now!" He turned back to Dean. "When I tell you to watch your brother, you watch him, got it?"
"Yes, sir." Dean nodded hanging his head in shame. Whenever his father yelled at him, he felt sick to his stomach. Sammy pushed open the sliding door, his book tucked under his armpit. He glanced quickly at Dean, trying to make sure he was alright, before looking again at Dad.
"Get your stuff packed." John ordered. "We're heading out. You too, Dean."
"Yes, sir." Dean nodded. Sammy said nothing, but went to get his clothes out of the dresser. John turned and stalked into the bathroom, taking his gun with him.
"What happened?" Sam asked quietly.
"Nothing." Dean said, refusing to look at his brother. "You heard Dad. Get packed." He shoved dirty clothes and toys into a battered suitcase.
"Where's your friend?" Sam asked.
"Shut up." Dean warned. "Get packed."
Sam obeyed.
Dean never saw Nate McAvery again. He made no effort to contact him at all, even though his mind wandered back to that day often enough. The poor kid was probably traumatized enough as it was, having a gun pointed to his head, without Dean dredging up the memory. Neither John nor Sam ever mentioned the incident again and eventually Dean did push it down beneath his subconscious, never to be spoken of or examined. He'd already disappointed his father enough. He learned his lesson. Boys didn't kiss other boys.
Oh, John Winchester, I blame you for everything wrong in Dean's life.
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