Dean didn't know much but he knew he couldn't let Cas die a virgin.

"So…" Dean coughed awkwardly as he spoke. Castiel found it strange that someone would do this when they were suffering no ailments but understood it to mean a signal of awkwardness. "Do you like women or men? Like...sexually...you know"

"I don't prescribe to your human concepts of gender" Castiel replied bluntly.

"Okay" Dean nodded despite being more confused than ever.

Perhaps a strip club was not the ideal location for anyone to lose their virginity, much less an angel, Dean had thought, as he escorted the trench coat clad heavenly body through the dark alleyway back to the car. "You know daddy issues are the reason these establishments exist, but you aren't supposed to bring them up." Dean said as they finally arrived at the car. Castiel sat silently staring out the windscreen at the neon lights bouncing off the wet tarmac.

"I don't think I wanted to have sexual relations with her anyway. My Father created sex as a pure and good thing. A pleasure so great yet so natural. It's the only thing humans are meant to do and have to do to survive, yet it is so beautiful. A shared human experience of pleasure. It wouldn't have been that with her, it would not have been shared in the way it should be. It would not have felt right."

Dean nodded. "I'm starting to think maybe you have daddy issue too." Castiel just frowned.

"That's true though…" Dean continued. "Sex is a lot better when your sharing it with someone you care about. Almost holy." Dean swallowed and stared out the front window, avoiding Castiel's sharp blue stare that he could feel burning the side of his face. For a moment, as the rain pounded down on the roof of the impala, as both man and Angel sat in silence staring at the strip club car park before them, a tension arose, as if something might occur in that moment that could change their relationship forever. But as the rain continued and the silence grew heavier, Dean reached for the keys and turned the ignition, and drove back to the motel, away from the feelings he so desperately feared.

February, 1996

During one of the longer stints the Winchester boys got to spend at school, Dean found himself actually enjoying himself. Though school was never his strong suit, he fell in quickly with a small crowd of guys who seemed to fit in even less than he did. Their own brand of personal trauma following them from school to school, as military brats or foster kids, left them with a shared innate understanding of each other. Despite the ghosts and demons and monsters under his bed, Dean felt, for the first time, like he fit in.

There was one kid, Ryan, that Dean found himself spending most of his time with. He was a foster kid and had been in and out of foster care since he was five, moving up and down the country every few months. Dean couldn't understand it, at first, Ryan was so respectable and well behaved. He never misbehaved in school, he kept to himself and even seemed to do well grade wise. But then, while wandering through the woods, as a way to put off heading back to the motel where his dad would no doubt be angry and drunk, Dean saw Ryan. He had a bag full of China plates and valuables. He took things out of the bag one by one, inspected it for a while, before smashing it on the ground, or throwing it in the air above him and shooting it out of the sky with an old gun he had no doubt stolen from his foster family, undoubtedly along with the rest of the valuables.

Dean stumbled as he tried to make his way past without being noticed. Ryan turned.

"Dean Winchester." He laughed. "You're the new kid from calc right?"

Dean nodded coyly. "Sorry, I didn't mean to intrude."

Ryan smiled. "Yeah...the McAllisters aren't great people, they don't deserve these plates."

Dean laughed. "Don't worry I won't tell anyone."

"Thanks." Dean went to walk off, before Ryan added.

"Hey, you wanna smash something?"

"Oh fuck yeah." Dean said. Before he knew it he was shooting commemorative plates out of the sky and stomping on small ceramic angels.

As the sun began to set the boys settled on a log beneath the navy sky, drinking beers Ryan had stolen from the fridge on his way out.

"Do you do this to all your foster families?" Dean asked.

"Only the ones that deserve it." Ryan sighed. "People don't tend to foster teenage boys unless there's a financial benefit. Child support is a great way to fund your gambling habit."

"Oh shit."

"Yeah they all have their reasons, either money or martyrdom. Ultimately they realise it's not worth the hassle and put me back in the system. Around thirteen I realised I was stuck in an endless loop and I may as well have fun with it. May as well start the fire if you're gonna get burnt, right? At least I'm not left wondering if it was something I did or if it's just me. If I'm just fundamentally unlovable."

"Oh boy do I know that feeling."

"Sorry. That was deep. Too much beer I guess. It's just nice having someone I feel like I can be honest with. No offence, but you seem just as damaged as I am."

"You don't know the half of it."

"Cheers to that."

Dean and Ryan became inseparable after that night. The months Dean spent at Jefferson High were spent mostly with Ryan. Neither had stable parental figures and so both the motel and Ryan's foster home were empty most of the time, meaning they could hang out, eat junk food and dodge the cops easily. Ryan had taken a penchant for public service and he and Dean would often get caught up in fights with men Ryan described as the town bigots. After a particularly bad encounter, Dean and Ryan slashed the tires on every car parked outside a seedy bar after several homophobic slurs were thrown their way upon entering. By the fifth car it was clear someone had called the police, and by the last the blue flashing lights had begun to illuminate the damage. Ryan and Dean fled into the night and found themselves in the motel room.

With Sam spending the night at a friends, and his father off hunting, the room was empty. Ryan ran his hand through his shoulder length blond curls as he lay on the floor next to Dean, breathing heavily and still stinking like beer and cigarettes from the bar.

"Do you think they'll track us back to here?" Ryan asked.

"No way. We used fake names, fake ID's. And we outran those fat ass cops so easily." Dean chuckled.

"Maybe we oughta disguise ourselves." Ryan sat up suddenly, his eyes sparkling as he spoke with excitement. "Dye our hair or something. In case they're looking for us."

"That's so stupid you re so drunk." Dean laughed.

"Yes! Exactly! I am young and stupid and drunk! Let's act young and stupid and drunk!" He grabbed Dean by the shoulder. "Where's the nearest drugstore?"

No more than an hour later, and two bottles of whisky down, both boys were sat on the end of Dean's bed, staring at themselves in the motel mirror. Dean reached his hand up to his head, his dark blonde hair now pink at the ends. He turned to Ryan, tracing his finger along his hair line, where his blond hair once fell so gracefully to his shoulders, now spurted softly upright from his head in a bleach blonde buzzcut.

"You look really good." Dean said, his whisky soaked tongue heavy against his lips. "I thought you looked pretty like a girl with the long hair but now I think you look pretty like a boy."

Ryan chuckled. "Thank you " He smiled sincerely, his face flushing pink. "You always look pretty like a boy." He licked his lips.

Dean could feel his heart pounding in his chest, his mind racing and his hands shaking, but his body telling him only one thing, kiss the boy. And so he did.

Ryan's lips were soft and his hands were strong when they traced up Dean's spine and cupped his face, leaning into the kiss. Maybe Dean had known all along this was where it was leading, maybe he wished he'd done this months ago, but maybe he knew in his gut it was a bad idea.

The door to the motel slammed open suddenly. Dean jumped up, adrenaline and fear sobering him up almost instantly.

"Dad." He said. "I thought you were away til the weekend."

"Whoever the fuck you are get the fuck out of here right now." John said. Ryan looked at Dean, his eyes filled with fear and concern but Dean just nodded, assuring him he should take his fathers order.

"See you at school." Ryan said quickly before running out the motel.

"What the fuck is wrong with you? You bring some kid in here with all our research, all our weapons and shit just laying about, you think that's okay? You think that's safe? He could be anyone"

"I'm sorry, sir."

"And where the fuck is Sammy? You send him out into the night just so you can do...this? You disgust me. Do you even know where Sam is? Do you even know if he's safe? -"

"- yes, sir he's-"

"-I can't believe I raised someone so… You are not a man… that is not what men do. You better grow up and grow out of whatever the fuck you think you are doing and you better do it quick. There's no fucking way you are going back to that school tomorrow. Pack your fucking bags, Dean."

Dean just nodded and started packing.

"I'm gonna go find Sammy. Then we're leaving."

John slammed the door shut as he left. As soon as the roar of the impala was out of earshot Dean picked up the phone and dialled the number he knew off by heart. He got the answering machine.

"Hi, Ryan. I...uh... I won't be seeing you again. Ever. I don't even know if you'll get this message. I don't even know if you should. I think...I think I might have loved you. But I need to get over that. I need to be a man. For Sammy. Goodbye. I have to go dye my hair now."