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Laughs of sheer humor escaped Dean’s lips for the first time – in a long time. He hadn’t laughed that hard in what seemed like forever and it felt good to just laugh once in a while. Opening the door to the Impala, Dean settled himself into the Driver’s Seat and simply smirked at the Angel residing in the passenger seat. He started the engine, listening to his baby ‘roar’ before heading back to the shack that had been made into a ‘Headquarters’ for this little ‘adventure’.

It was a few miles into their trip before Dean realized something. The Angel was still a virgin.

Dean had almost made it seem like a pledge, to not let Castiel die a virgin – and even though it was more so a determined statement, Dean still wasn’t planning on letting the Angel die without knowing the full extent of enjoying life.

The Brothel idea had gone up in smoke and it probably wouldn’t end up any better if they tried it at some other place. Dean could give Castiel some ‘tips’ on things not to say. In fact, it would probably be best if Castiel just didn’t say anything. The idea was as impossible as it came and so the need for a different idea arose.

Looking down at the radio clock, Dean frowned deeply. It was a little past 12, which only gave them five hours to find some solution to the Virgin problem, as well as set up for the Raphael Ritual. Castiel didn’t stand a chance with someone, at least not with the lacking knowledge that the Angel had on sex, and how to even treat the other individual during the encounter.

Dean gave a faint sigh; not wanting to give up on Castiel having one last night on Earth. That was the least he could do for the guy. After all that they had been through, Dean almost felt like he owed this to Castiel.

To Dean, it almost sounded like he was offering himself up to having sex with the guy.

…

Dean’s brain shut down for a moment as he tried to let the thought settle in, or go away. It didn’t matter which, but images of the two of them entwined together gave Dean shivers and he shook his head to rid himself of the thoughts.

“Dean?”

Castiel’s voice broke in and the Hunter glanced over to him. The Angel stared back, with a curious expression before shifting his blue eyes to the road. “Humans…drive on the right side of the road….”

The statement was an odd one to Dean, and it almost didn’t click until the blaring sound of a car horn tore his eyes away from Castiel. A dark green Honda had quickly swerved into the ditch to avoid a collision and Dean blinked. He didn’t bother stopping, else he would have even less time to figure out how to help Castiel’s sexual problems, and so he adjusted the Impala to the right side of the road before he briefly glanced at the Angel.

Neither said anything for a while and so Dean ignored that anything had happened. If something didn’t work out in Dean’s favor, he normally tried to forget about it. This was one of those occasions, and so he would simply stick to his usual plan.

Ignore it.

Dean’s thoughts returned to the idea of having sex with Castiel, and the more he thought about it, the more logical it sounded. It was more logical, in the sense that it was probably their best chance at succeeding. Though, in Dean’s personal opinion, being f**ked up the @ss didn’t seem to hold much logic at all.

It was Castiel’s last night on Earth, and so Dean felt as though he could do something like this, this ONE time. Cas was someone who Dean would consider a friend and so he obliged to do something like this.

Finally making up his mind to go through with the plan, Dean felt that he should at least pick up something to ease the burden on himself. Spotting a local grocery store, Dean pulled into the parking lot and got out of the Impala.

“Wait here.”

That was all that he said before disappearing into the building and returning only a few minutes later with a bag in hand. The plastic container was idly tossed upon the bench seat between them. Castiel stared at the bag oddly before giving Dean a questioning look.

“Don’t worry about it Cas.”

They rode the rest of the way to the shack in utter silence. Dean needed some mental time to prepare himself for the suicide attempt that he was planning. He had never considered being the submissive individual in a**l sex and would never consider it again. There was no way in hell that he was gay, and he wouldn’t dare think about switching the roles and making Castiel being the submissive one. It was supposed to be Castiel’s last night on Earth, and Dean wasn’t planning on making a painful one to remember.

Pulling into the driveway, Dean parked the Impala and grabbed the plastic bag before heading into the shack; Castiel following close behind. The bag was set down upon a rickety table and Dean took in a deep breath, reviewing all that he had gone over on their way here.

Everything made perfect sense, except the fact that he was actually going to go through with this. In all his life, he never once considered the idea of being f**ked. So it made Dean wonder if deep down he was a closet case, at least for Castiel. No one else would he have done this for and no one else would he ever do this for.

Either way, the main problem with this entire plan, was how to go about doing it. He normally just went with the flow on things, but at the moment, there was no flow in that direction.

Castiel had probably long forgotten the idea of getting laid, and some how that made Dean’s job a little easier. He wasn’t sure how, seeing that if he jumped the Angel and demanded sex, Castiel might retaliate, being caught off guard and all. Then again, slowly working his way into the situation didn’t really suit Dean; especially with Castiel.

The Angel always seemed to be asking questions, or at the very least, asking ‘why’. For some reason, Castiel couldn’t accept something as a statement or an answer, there always had to be a further reason to things and as funny as it seemed before – that the Angel was so curious about how humans thought and acted – right now, Dean didn’t feel like answering the ‘why’s that he knew were coming.

Dean was on the verge of ‘rock-paper-scissoring’ in his mind, though he ended up just deciding on his own. He took a step towards Castiel, followed by another and then another, until they were mere inches apart.

Castiel didn’t seem to mind this in the least. His face held a slightly curious expression and as Dean leaned in further, the expression went blank. More surprised rather than blank, but it was a Deer Caught in Headlights surprised.

No matter how close Dean got, Castiel didn’t back away. It was only at this point that Dean grabbed Castiel by the edges of his coat with one hand and led him gently against the nearest wall. He was certain that if the Angel had any opposition to this, that Castiel would voice them.

The one inch difference between them made it easier to deal with noses and other practicalities, and Dean held Castiel’s jaw between his fingers, letting the other hand remain clutched within the beige trench coat, while he gently let lips touch against lips.

It was at the first touch of lips that Castiel’s hands shot up to grab Dean’s forearms. He didn’t push the hunter away, nor did he pull him closer. Castiel only held Dean in place as their lips molded together.

The formation of the kiss – was more so a ‘warning’, a hint in the direction that Dean wanted to go and if Castiel was at all opposed, then he should stop the situation from being directed any further.

Lips against his became a breath less stiff after initial resistance and Dean took this as a sign to continue. He didn't think that Castiel would run off now - or rather, punch Dean through the wall and then run off. He inched his body closer, making sure to telegraph each movement well in advance and to move slowly.

Castiel immediately tightened his grip on Dean’s arms; his fingers flexed slightly, as if curious yet cautious about testing the extent of their involvement, and the lips finally shivered beneath Dean’s.

Dean tilted his head and opened his mouth. His hand drifted from Castiel’s coat to his hip, where he started kneading a slow pattern with his thumb; trying to get him comfortable to the idea of being this intimately close to another individual.

Slowly, Dean let his tongue come into play, first against Castiel’s lips. Castiel’s fingers clenched in surprise but the Angel didn’t pull away. So, Dean went further, slowly but surely, nudging Castiel’s lips apart and taking a quick swipe inside. It tasted like nothing in particular, probably because Castiel never ate. Dean would actually have found it weird if the Angel tasted like anything more than tongue and a hot mouth.

Breaking away, Dean changed the angel of the kiss, before sliding his hand further up Castiel’s jaw, fingers nudging the spiky black hair. Dean shifted his grip on the edge of the coat before settling the hand on Castiel’s shoulder and pressed their bodies firmly together.

Castiel was surprisingly warm through so many layers of clothing and Dean leaned into that chest like a wall; his fingers appreciating the sheer solidity of Castiel’s body as they felt along the Angel’s tensing shoulders.

The moment that Castiel became comfortable with how things were moving, was the moment that Dean moved a step further, which made Castiel tense again. Moments would pass before the Angel was comfortable once more and then Dean would move to more intimate terms.

It seemed like an endless cycle between the two of them, but for some reason, Dean wanted to remember this. He couldn’t convince Castiel that trapping Raphael was foolish. Such an attempt on Dean’s part would be foolish, and so he did the next best thing. He was making something out of the Angel’s last night.

Beneath Dean’s cupped palm, the pulse at Castiel’s throat was going at a rapidly healthy pace. The heat, the closeness, the shivering power in the muscles against his body, made Dean’s cardio-vascular system pick up in pace as well.