Ok everyone, so decided to try my hand at some Supernatural fanfics since I just can't get enough of those lovely boys ;D This is my first time trying out a Destiel fic so please don't judge too harshly, but do tell me if I accidentally made anyone out of character. I really hate when I do that, so it'd be nice to get some feedback on that.

Set during Season 5 ep. 3 in case you didn't notice from the title lol.

Dean let out a tired sigh as he flipped through his dad's journal again, trying to think about how the hell he and Castiel were supposed to trap an angel. Sure he didn't think his dad had anything in his journal that could help, especially since Dean hadn't even known angels were real until he met Castiel, but it wasn't like he had any other options at the moment since the angel had disappeared on him all of a sudden.

Since it was really dark in the decrepit house and the moonlight wasn't providing enough light for Dean to be able to read properly he made his way over to the old table in the living room by the window just to close the journal and set it down. He looked up when he suddenly felt that familiar warmth that always came over him whenever the angel was around and he looked up to see Castiel standing in the doorway looking around.

"Where've you been?" Dean asked curiously, a little aggravated that the angel had left without so much as a word earlier when Dean didn't know what the hell he was doing or supposed to be looking for in order to trap Raphael!

Castiel looked to his charge with a shrug. "Jerusalem," he said simply as he began making his way over to the table by Dean.

"Oh, how was it?" Dean snapped a bit.

"Arid," the angel answered, completely obviously to Dean's aggravation.

"And why the hell did you go to Jerusalem exactly?"

"For this," he answered as he sat the jar he was carrying on the table.

Dean arched a brow in confusion. "And what is that?"

"It's oil. It's very special, and very rare," the angel answered as he took a seat.

"Great. We're gonna trap Raphael with a nice vinaigrette?" Dean asked sarcastically.

"No."

Dean let out a frustrated sigh. Why the hell did Castiel have to be so damn hard to talk to sometimes? It was like his mind was a million miles away or something and he was only focusing just enough attention on Dean to give him a short answer without really thinking about it. He shook his head, "Right… So this ritual yours, when does it got to go down?"

"Sunrise."

Dean nodded, "So tell me something. You keep saying we're gonna trap this guy, but isn't that kinda like trapping a hurricane with a butterfly net?"

Castiel thought about it for a second since he honestly hadn't thought something like that was possible. He shook his head, "No, it's harder."

"…Do we have any chance of surviving this then?"

Castiel looked up at the man. "You do."

Dean furrowed his brows in thought. "So odds are you're a dead man tomorrow?"

"Yes."

Dean frowned as he made his way around the angel, hoping his friend was wrong about that. He looked back to Castiel and his frown deepened when he noticed the angel staring out the window with a defeated look on his face. "So…your last night on earth… What are your plans?" he asked curiously, thinking maybe he could get Castiel out and cheer him up a bit.

"I just thought I'd sit here quietly."

Dean gave him a perplexed look, "Dude, come on. Anything? Booze, women…?"

Castiel nervously looked to him, starting to feel uncomfortable with the knowing look he saw on the hunter's face.

"…You have been with a woman before, right? Or an angel at least?" Dean asked in shock just to see the male nervously rub at the back of his neck. He shook his head and leaned down just to see the angel's cheeks appeared to be stained a light pink. "You mean to tell me that you've never been up there doing a little cloud seeding?"

"I've never had occasion, ok?" Castiel said softly, hoping Dean would just drop the subject already.

Dean tried to bite back his laughter since the angel was his friend, and after he got himself under control he nodded and made his way past him to get his jacket. "Alright. Let me tell you something, there are two things I know for certain. One, Bert and Ernie are gay. Two, you are not gonna die a virgin. Not on my watch."

Castiel's eyes widened at the hunter's words and he felt his heart speed up for some reason as Dean looked at him. He was almost tempted to ask what exactly Dean meant by what he said, but he furrowed his brows in confusion when the man suddenly said 'let's go' and made his way past him.

The angel was quiet as he followed Dean out to his car, extremely curious as to what the man had in mind exactly. He arched a brow when Dean soon brought the car to a stop and got out and Castiel quickly followed after him. His eyes widened as soon as they made their way inside and he noticed half naked women everywhere, and he felt himself start to panic a bit as they were led to a table and Dean ordered them a couple of drinks.

Dean couldn't help but arch a brow as they took a seat and he noticed Castiel looking around like he was about to have a stroke and pass out. "Uh, Cas? You ok?" he asked worriedly.

"This is a den of iniquity. I should not be here!"

"Dude, you full on rebelled against Heaven. Iniquity's one of the perks," Dean chuckled, smirking when he noticed a hot young blonde making her way over to them. "Show time," he muttered to himself as she made her way over to Castiel.

"Hi. What's your name?" the girl asked with a bright smile as her eyes raked over the angel.

Dean shook his head as he watched his friend looking as though he were struggling to breathe, "Cas. His name is Cas. What's your name?" he asked, deciding to help out.

"Chastity," the girl replied with a wink.

Ok yeah…Castiel was really starting to get uncomfortable here. He picked up his drink he'd left untouched until now just to turn it up and start chugging it, not really paying attention when he heard Dean saying something to him.

"Well he likes you, and you like him so…have fun yeah?" Dean said with a grin, laughing as he noticed the panicked look the angel was giving him as the girl grabbed his hand and pulled him to his feet. "Damn she is one lucky chick," he thought to himself as he watched them start to head off.

He jumped up when he suddenly remembered he'd forgotten to give the guy any money and he quickly grabbed his arm and turned him around just to hand him some cash. "Hey listen. Take this, and if she asks for a credit card say no. Now just stick to the basics ok? Do not order off the menu," he instructed.

Castiel furrowed his brows in confusion, wanting to beg Dean to just get out of there. Seriously, this was just really getting awkward! "Dean…"

"Go get her, Tiger," Dean interrupted. "Don't make me push you," he added after he noticed the look Castiel was giving him.

The angel let out a defeated sigh as he took the money from the hunter and he followed after Chastity. The closer they got to one of the rooms, the more nervous he became. He badly wanted to just take off, but he had a feeling that if he did that Dean would be upset with him since this seemed like it was supposed to be some kind of gift.

He let out a shaky breath as she pulled him into one of the rooms and pushed him back onto the bed just to crawl into his lap and start pulling his coat off. He grimaced as he felt her fingers tangling in his hair while her lips moved to his throat, and he shifted uncomfortably on the bed.

"Just relax, sugar," the woman giggled as she slowly ran her hand down his chest to start undoing the buttons on his shirt.

Castiel frowned as he suddenly felt something coming from the girl, some kind of hidden pain she seemed to hold, and he couldn't help it as he pulled back a bit just to look at her.

Dean was currently seated at the bar having drinks with a pretty young woman when he suddenly heard a scream coming from the back rooms and he quickly excused himself and took off down the hallway just to see Chastity standing out in the hallway and cussing the angel out.

"You bastard! Screw you! I'll kill you!" she shouted furiously as she threw something at him just to turn around and start making her way towards Dean. "And screw you too!" she snapped as she made her way past.

Dean held his hands up in surrender as she stormed by just to make his way over to his disheveled looking friend. "What the hell did you do?"

Castiel frowned, "I don't know. I just looked at her in the eyes and told her that it wasn't her fault that her father, Gene, ran off. It was because he hated his job at the post office."

Dean couldn't take it and he started laughing, "Oh no, man… This whole industry runs on absent fathers. It's the natural order," he explained just to look behind him when he heard footsteps. He grabbed the angel's arm when he noticed security and he tugged, "We should go," he told him just to quickly run out the back exit, laughing at the angel as hard as he could on the way out.

Castiel furrowed his brows in confusion once they were outside and Dean was holding his sides as he laughed. "What's so funny?"

Dean shook his head just to wrap an arm around the male and pull him into a sideways hug. "I'm sorry, Cas, but wow. You're like the only guy I know of that went to a whorehouse and couldn't get laid. It's just pretty damn funny."

Castiel frowned as the two of them walked back to the car. "I'm sorry."

Dean arched a brow in confusion, "What for? You didn't do anything to be sorry for."

"You brought me to this place for a reason, like a gift or something, and I obviously just ruined it…"

Dean found his lips quirking up into a smile, "He is just too cute sometimes," he thought with a sigh. "You didn't ruin anything, Cas. Hell, I haven't laughed that hard in a long time. We'll just have to try somewhere else, after all I never break my promises."

Castiel grimaced as he got into the passenger side of the Impala and he looked down at his hands in his lap. "I would rather we didn't try anything like this again…"

"What? Oh come on, if this is about the whole iniquity thing then-"

"It's not that," Castiel interrupted. "I just didn't feel very comfortable in there. If I end up doing…that I would rather it be with someone I know and am comfortable with… Better yet I would rather it be with someone I like."

Dean frowned in thought, "Ok…well anyone you happen to have a crush on that we might be able to find you? Seriously, I'm not going back on that promise."

"Well…there does happen to be someone I find myself quite fond of…" the angel admitted softly.

"Great. Who is it? Is it someone already here on earth? Or are we gonna have to make a call to an angel?"

Castiel nervously licked his lips as he brought a hand up to nervously rub at the back of his neck. "I uh…h-he happens to be here already."

"He?" Dean asked in surprise. "Wait a minute, I thought there was this whole anti-gay rule in Heaven or something like that."

Castiel furrowed his brows in confusion. "What? No. Why would you think that?"

"Well you know what with the bible saying it's this huge sin for a man to lie with another man or whatever."

Castiel took a moment to think before shaking his head. "No, there's nothing in the bible that says that. You humans tend to get a lot wrong, mostly mistranslations I think. If you're talking about what I think you are then that was something to do with pedophilia."

"Huh… Well that's a bit of a relief. Here I thought I was gonna end up in hell again whenever I died."

Castiel canted his head to the side curiously as he looked to Dean. "Why would you think that?"

Dean shrugged, "Well…Sam doesn't know, so if I ever see him again I'd appreciate if you didn't say anything, but I've actually been with more guys than I have chicks. I just put on the charm for our cases since it helps to get information out of some of the ladies."

"Really? …So if this person I happen to be comfortable with turned out to be you…what would think about that?" the angel asked nervously.

Dean blinked, unable to really process what he'd just heard. It wasn't that he was appalled by the idea or something, hell no, but he'd always thought the angel was off limits since well…Cas was a freaking angel!

Castiel's face fell, taking Dean's silence as a rejection. "I think I'm going to hurry and head back to our hideout. I'd like to get started on sitting quietly now," he said softly.

Dean quickly reached out and grabbed the angel's arm, "Whoa, wait. Don't go disappearing on me all of a sudden. I think I saw a motel somewhere around here, so just chill out and let's go get a place with a comfortable bed at least. Seriously, we are so not doing anything in that shithole we've got set up for Raphael."

The angel looked at him in surprise. "You mean you…"

Dean grinned, "I already told you I'm not letting you die a virgin on my watch, and I'm liking your plan B."

Castiel nervously turned to look out the window, starting to feel the same panic he felt in that den of iniquity when Dean pulled into a parking lot and got out of the car just to tell him to wait there. He watched his charge go inside and talk to a woman behind a desk, feeling less sure about this whole thing as Dean came back out with a key and motioned for the angel to follow him.

He let out a deep breath as he made his way over to the room with Dean. He shuffled in after the hunter just to start feeling that sensation to flee all over again when Dean closed the door and he found himself pinned up against said door. He let out a shaky breath as he felt the man's hands divesting him of his overcoat just to jump a bit as Dean leaned in and Castiel felt a pair of soft lips pressing against his own.

He shivered as he felt the man slowly unbuttoning his shirt, Dean's fingers lightly brushing against his flesh. "D-Dean? I…I don't know what to do…" he mumbled when the man's lips moved along his jaw and up to his ear.

"Just follow my lead and try to mimic me," the man whispered just to lightly nip at the angel's ear.

Castiel hesitantly brought his hands up to start pulling Dean's shirt up and over his head, gasping when he suddenly felt the man's calloused hands slip into his open shirt to start running over his flesh.

Dean smiled against the male's flesh as he trailed kisses down his angel's neck, his hands quickly undoing Castiel's tie and getting it out of the way. He slid his knee between the male's legs and pressed himself closer as his hands traveled down Castiel's sides to rest on his hips.

"Ah! D-Dean," the angel whimpered as he felt a strange stirring low on his body. He gasped as he felt the man's teeth running along his neck and he found himself tilting his head to the side to give the hunter better access. He tried to focus on copying Dean since he didn't want the man to be doing all the work, and he brought his hands up to slowly start running along the man's chest.

He lightly raked his nails down Dean's stomach just to nervously nibble on his bottom lip as his fingers came into contact with Dean's belt. He wasn't sure what he should do next, but all thought flew from his mind when Dean suddenly captured his lips again and he felt hands tugging at his own belt. He tried to focus on the feel of Dean's lips when that same feeling of panic started to wash over him and he tried to move his lips with Dean's, shivering when he suddenly felt the man licking at his lips.

The angel hesitantly parted his lips and he gasped when he suddenly felt Dean's tongue sliding against his own. His breath hitched as he felt a hand slipping into his pants and he let out a low moan as he suddenly felt those calloused fingers wrapping around him. He let out a soft whimper, his head falling back against the door as he felt the man stroking his aching flesh. "D-Dean…"

Dean shivered at the beautiful way Castiel moaned his name, and he quickly finished stripping them both down just to pull him over to the bed and lightly push him down on it. He licked his lips as he looked his angel over, unable to resist taking a moment to appreciate the sexy male in front of him.

"Is something…wrong?" Castiel asked nervously just to take a shaky breath as he felt the man sliding a hand up his thigh.

"Just enjoying the view," Dean said with a smile before he slowly crawled between the male's legs. He lightly gripped Castiel's hips and pulled them close, slowly grinding against the angel and licking his lips upon hearing the beautiful moan he ripped from his throat. He leaned down to nibble and suck at the male's lips, his eyes slipping closed as he felt Castiel's arms going around his neck.

Normally Dean didn't take his time like this, so he found himself a little impatient to get to the good part, but this was Cas… He wanted to make this just as enjoyable for his angel as it was to him, and honestly it was rather nice to take things slow for a change. He didn't get to do this much with someone he actually cared about after all.

He quickly pushed those thoughts aside since he didn't even want to start thinking about what it was he actually felt for Castiel, and he slowly started to nibble his way down along the male's throat. He grinned as he heard a whimper escape the angel as he started kissing down along Castiel's chest, his tongue lightly flicking over one of the male's nipples just to lightly nip and suck at it.

Castiel's body was reacting strangely to everything Dean was doing to him, and he found himself arching up into the man as Dean thoroughly teased his chest. He tightly clenched the covers under him when he felt those lips continuing their trail down his body, a shaky moan being pulled from him upon feeling the man's lips sliding along his length.

Dean smiled against the hard flesh before teasingly flicking his tongue out to lightly trail over the male's balls, sucking them into his mouth as he listened to the angel mewl and moan in pleasure. He wasn't exactly used to this kind of thing since he was always the one on the receiving end of a blowjob, but he wanted Cas to have one hell of an experience.

He pulled back after a few moments to lick his way up to the tip, his tongue playing with the slit and ripping some extremely arousing sounds from the angel's throat. He shivered as he heard Cas moaning his name and he slowly started to take him into his mouth just to start to bob his head, taking in a little more of the male each time and sucking a little harder with every inch.

Castiel was a mess, his nerve endings on fire as he felt Dean's hot mouth around him, sucking him so amazingly he was practically seeing stars. He let out a moan in his true voice when he suddenly felt the man's teeth lightly dragging over his shaft and he tightly clenched the covers under him at the sensation.

He gritted his teeth when all of a sudden everything stopped and he noticed Dean pulling away. He wanted to beg the man to go back to what he was doing, though he furrowed his brows in confusion as he watched him lean over towards the table by the bed just to open up the drawer.

The angel panted heavily as he watched him pull a small bottle out of the nightstand, and his body trembled as Dean leaned down to capture his lips. His eyes fluttered closed as he parted his lips and felt Dean's tongue slip past to slide against his own once again. He was curious as he heard something make a soft clicking sound, but he paid no attention to that since Dean was keeping him rather distracted with the heated kiss.

He gasped as he suddenly felt something slick and cold around back of him, and he flinched as he felt one of Dean's fingers slip inside of him. His body tensed up on reflex, only relaxing when he felt the hunter soothingly running a hand up his thigh. He gritted his teeth, a pained groan coming from him when he felt a second finger join the first.

Dean tried to be careful as he prepared the male, searching for that spot that would have his angel forgetting all about the discomfort. He smirked as Castiel suddenly arched up into him, his name spilling from the angel's lips as he did so. He could tell Cas was about to ask him about it, but he didn't give him time to do so and instead captured his lips in another kiss as he continued to assault the male's prostate.

Castiel was so overwhelmed with pleasure that he didn't even notice when Dean slipped in a third finger, and he even started to hesitantly move his hips as his head fell back in bliss. In all of his life Castiel could never remember feeling anything like this before. It had him wanting more even though he wasn't sure how it was possible to feel much more than this.

He let out an involuntary whimper in protest when he suddenly felt the hunter pulling his hand away, and he wasn't sure exactly how to ask for more of that blinding pleasure. He nervously licked his lips as the man situated himself in between his legs and he felt his cheeks heating up when he noticed something pressing up against him that felt bigger than the man's fingers.

Dean offered a soft smile when he noticed the angel tensing up once again and he brought a hand up to softly caress the male's cheek, his thumb lightly trailing under his eye. "It's ok, Cas…"

The angel's eyes fluttered closed as he nuzzled into the hand caressing his cheek. He tried to stop the nervousness he was feeling since it didn't appear that Dean was going to continue until Castiel got himself under control, but it was rather difficult to do since he'd never done anything like this before.

He found it helped that Dean was littering his neck with kisses while his hands trailed down along his body. Castiel arched into the touch, his own hands making their way up Dean's chest and around to his back when he suddenly felt the man lifting his hips a bit. He gasped, his nails digging into the hunter's back when he suddenly felt a sharp pain in his backside. His body was on sensory overload at the moment so he didn't even think to use his grace to dull the pain he was feeling.

Dean gritted his teeth as he felt the angel's nails digging into his back, and he tried to resist from letting himself go and just roughly taking the male. Once he was completely seated inside he gave Castiel some time to adjust, taking the moment to distract his angel with another passionate kiss.

Castiel was glad that Dean seemed to be giving him a moment since he didn't think he'd be able to really handle if the man started moving just yet. He was also glad that the hunter seemed to be trying to distract him from the pain he was feeling by kissing him breathless, and his eyes opened a bit when Dean suddenly broke their kiss.

The angel felt his cheeks heating up as he noticed the man watching him intently, and he wasn't sure why but it was making him feel a bit uncomfortable. It was odd really but Castiel just felt so open and vulnerable under the man's gaze at the moment. Of course this new feeling it caused must've replaced the pain he'd been feeling since he was only reminded of it when Dean gave a small roll of his hips.

He gasped a bit in pain, his nails biting into the hunter's back once again just to furrow his brows in confusion when Dean started shifting his hips around. He was about to ask him what he was doing when the man suddenly hit that spot inside of him that he'd found earlier with his fingers, and suddenly any remaining pain Castiel still felt had vanished.

His head fell back in ecstasy as his legs tightened around the man's waist, and he let out a loud moan as Dean focused on that spot and gave a sharp thrust into him.

Even though it was obvious Castiel wasn't focused on the pain anymore, Dean still tried to be careful as he slowly thrust into the male. Of course it was getting more and more difficult to keep from losing what little control he had when he felt those nails raking down his back and those legs tightening around his waist and pulling him deeper. God he'd never seen Castiel like this before…and honestly it made him wonder why the hell he'd waited so long to do this.

He kept his movements slow and loving since he didn't want this to be over too soon, and he also didn't want this to be classified as just another fuck when Castiel meant more to him than that. His hands trailed up over the male's soft skin, his fingers lightly brushing over the angel's nipples as he nibbled down his throat and littered it with love bites.

Castiel moaned loudly as all these sensations washed over him, and he almost couldn't stand it because it was all too much. Dean's lips trailing over his skin, his hands running over sensitive areas on his body, the way the hunter was slowly moving his hips and hitting that spot in him that was driving the angel so close to the edge he started speaking in Enochian.

He gritted his teeth as he felt the pressure building, and he let out a shocked moan as he suddenly felt the man's calloused fingers wrapping around his aching length just to start stroking him in time with their movements. He leaned up and bit into the hunter's shoulder as he felt something in him starting to break.

Dean gasped, gritting his teeth a bit when Castiel suddenly let out a loud, sharp sound in his true voice that had the windows threatening to break, and he quickly covered the angel's mouth with his own to silence his screams as he felt his lover's warm release on his stomach, giving a few more thrusts of his own before he followed the male over the edge.

They were both breathing erratically as Dean brought a hand up to caress Castiel's cheek, pulling him into another soft kiss as he carefully rested his weight against the male since he wasn't exactly wanting to move just yet. He smiled into their kiss as he felt Castiel's hands moving up just to feel his fingers tangling in his hair as he kissed him back. He let out a soft sigh when he finally broke their kiss and he moved back a bit just to get a good look at his angel, smiling as he noticed how relaxed Castiel looked for once.

"So…how was your first time?" he couldn't help but ask.

Castiel felt his cheeks flame at the sudden question. "It was…amazing. If I knew it would be like that I would've done it a long time ago," he admitted.

"Yeah well, I'm kind of glad you didn't."

Castiel canted his head to the side in confusion. "Why's that?"

"Because if you had then we most likely never would've ended up doing this," Dean laughed.

Castiel smiled, "I suppose you're right… I'm glad you were the one I did this with, Dean…" He let out a soft sigh as he moved to softly nuzzle Dean's neck, suppressing the sudden urge to materialize his wings and wrap them around his hunter.

Dean felt his cheeks heat up a little, feeling just a little uncomfortable since this was starting to sound like a chick-flick moment, but this was Cas so he decided he could put up with it just this once.

Once he had his breathing under control he carefully removed himself from the angel and laid down next to him just to pull him close as his fingers lightly trailed up the angel's side. "…Cas?"

"Hmm?"

"You'd better not die tomorrow…"

Castiel smiled brightly. "I'll be careful… I'd like to have the chance to do this with you again," he said as he moved his hand up to lightly cover the handprint that was branded on Dean's arm.

Dean shivered as he felt a spark shoot through him at the contact, and he leaned in to rest his forehead against the angel's as he felt his heart start to race. "…Same here," he whispered softly, a smile of his own tugging at his lips as his eyes slipped shut.