Author's Note: Ok, so hi, this is my first Supernatural fanfic but deff not my first slash. This idea came to me after watching 5.03 "Free to be You and Me" and it's based on the scene just before Dean takes Cas to the brothel. Here's my little twist on that. I don't know if the concept has been done before but when the idea struck I just couldn't ignore it. Plus I really wanted to write an SPN fic and I felt like this was the perfect way to get started.

Disclaimer: Supernatural and its characters do not belong to me. I'm just borrowing them for a few minutes. I was gunna give them back. I swear.

Rating: PG

Warnings: Slash. Duh.

"Do we have any chance of surviving this?"

"You do." Castiel answered as if that would be enough to convince Dean that going through with this was going to be a good idea. But Dean wasn't buying it.

"So, odds are you're a dead man tomorrow," Dean said after a long pause. It wasn't a question but Cas replied as if Dean was asking.

"Yes."

Dean blinked and shook his head. "Wow." He took a few steps forward, stopping as soon as he reached the dooway. Then he turned back to the angel. "Well, last night on Earth. What, uh, what are your plans?"

"I just thought I'd sit here quietly," Castiel seemed pretty calm for someone who was unlikely to live past tomorrow. However, Dean wasn't about to let that happen. He had to do something to repay Cas for all he was doing to try and save the planet.

"Dude, c'mon," Dean stepped towards Cas. "Anything? Booze? Women?"

Cas shifted and averted his eyes to the floor. He remained silent.

"You have been with a woman before? Right?" Dean pried, moving closer still. "Or an angel, at least?"

Again, Castiel didn't answer. He just rubbed the back of his neck nervously. Dean leaned down next to him. "You mean to tell me you've never been up there doing a little cloud seating?"

"I've never had occasion, ok?" Cas spat out defensively. He still refused to look Dean in the eyes.

Dean now knew what had to be done. "Alright," He straightened up and walked over to the table to grab his coat. "Let me tell you something. There are two things that I know for certain," He said as he stuffed an arm into his sleeve. "One. Bert and Ernie are gay. Two. You are not gunna die a virgin. Not on my watch." Dean adjusted his collar and once again started for the door. "Let's go."

Castiel got to his feet and stood there for a few moments, unsure of what he wanted to do. He wished Dean would just let him sit here, in the dark quiet of the old abandoned house to reflect on his life thus far, but he knew that the hunter would never let him. But if this was going to be his last night on Earth, he sure as hell wasn't going to waste it.

"Dean," He sighed and called after him. "Dean, wait!"

The hunter paused and faced the angel. "What?"

"I-I can't do this," Castiel's normally strong and gruff voice was shaking.

Dean didn't look convinced. "Cas, there's nothing to worry about. You're with me, and I promise I won't let any ugly chicks near you. Trust me, I've got this." He started to walk away again and again, Castiel cut him off.

"Dean, I'm serious," Cas pleaded, latching on to Dean's wrist. "Don't make me do this."

The elder Winchester raised an eyebrow skeptically and pried the angel's hand off his arm. "Jeez, Cas. What's wrong with you? I've never seen you so jumpy before."

"I'd rather not say," Castiel shifted on his feet and once more avoided eye contact.

"Oh, c'mon, Cas," Dean smiled and placed a reassuring hand on the angel's shoulder. "You know you could tell me anything."

Castiel refused to speak, leaving Dean to try and guess what was wrong.

"Do you already have feelings for someone else?" Dean said the first thing that came to mind. Castiel swallowed hard.

"You might say that, but it's a bit more complicated than that-"

"It is Anna?" Dean guessed. "Seem like you guys might have had some history together." He winked and playfully nudged Castiel.

Cas shook his head. "No Dean. It's not Anna."

"Ok then who?" Dean refused to let this one go. "Someone I don't know?"

"I can't say."

"Why not? If I don't know her, what's the big deal?"

"Dean can't you just—"

"Is it a demon?" Dean cut him off.

"What?" Castiel looked extremely offended. "I would never even consider something so blasphemous."

Dean held his hands up in surrender. "Ok so if it's not a demon. Then who?"

Castiel's lips remained sealed and Dean about had enough of this game.

"Fine Cas, you don't want to tell me, don't. I can't force you to do anything." Again, Dean was on his way to the door. "I was just trying to help." He stomped down the hallway and placed his hands on the door knob, ready to turn it and walk out, only to come back when Castiel begged him too, when a presence behind him made him freeze. When Dean turned around, Castiel was standing right there.

"Cas, we've talked about this. Personal—"

"It's you."

Dean was taken completely off guard. So much in fact that his brain wasn't making the connection with what the angel just said.

"Uh, no. I think we can all agree that you're the one who has issue with—mmmph!" But Dean never got the chance to finish because, well, it's kind of hard to say anything what with an angel's lips pressed up hard against your own.

Before Dean even realized what was going on, Castiel pulled away and suddenly things were making a lot more sense.

"I'm sorry if I offended you," Castiel started. "But I felt that was the only way that I could prevent you from leaving."

Dean's freshly kissed lips curled up into a wry smile and again he reached for the door knob. Castiel looked confused.

"Dean, I thought I made my position quite clear."

"Oh, you did," Dean assured him, fumbling with the lock.

"Well then why do you still insist on leaving?"

"I told you," Dean grabbed Castiel by the hand and reached into his jacket pocket with the other, producing the key to his motel here in town. "You are not gunna die a virgin. Not on my watch."

A/N: Thanks for reading! Reviews are love!