Castiel emerges from the small hotel bathroom, rolling up the sleeves of the flannel Dean has lent him, after his third shower as a human. His hair is dark brown from being wet, and sticks up at odd angles, though he pays it no mind. His black slacks, freshly laundered but fraying at the hems are a stark contrast to the casual shirt, but Dean's jeans are too baggy and Sam's are far too long. Dean tosses his stripped gun to his side, the mattress giving very slightly under its weight. He looks up and sighs, making a mental note of how he and Sammy will have to take Cas clothes shopping soon.

"Everything okay with the shower?" Sam asks from behind his laptop, surprised a trail of water has not followed Cas out this time as he glances up.

"I believe I am mastering this skill, yes." Cas' response is low and even, and if Dean didn't know any better, he'd think his gaze was still upon an unfeeling, junk-less angel.

"Did you wash the shampoo out this time?" He asks cracking a lopsided grin, while Cas simply nods.

"It is important I learn these grooming procedures – I am being courted."

"Wait, what?" Dean asks, sure he's misheard the brunette still fiddling with his cuffs.

Sam rakes his fingers through his shaggy mane, eyebrows high as he asks, "You mean, you have a date?"

Castiel looks upon the brothers, a slow realization overcoming his features. "You have reason to doubt me? From what I understand, Jimmy is – I am - aesthetically pleasing."

"Cas, no one's saying you're ugly. We're just surprised, what with humanity being so new to you and all." Dean shakes his head, pulls his duffel bag close to his feet, and unzips it quickly. Digging through the folded shirts and glossy, new copies of "Busty Asian Beauties," he fishes out a box of Trojans and tosses one at Castiel.

"Here – 'no love without the glove', right?"

Cas turns over the foil packet, and cocks his head to the side. "There are gloves in here?" He asks, bringing it closer to his face.

"Oh, boy…" Sam mutters, closing his laptop. "I'm going to head to the library to follow up this lead. Dean, you can take this one." Sam stands up, shaking his head as he stifles a laugh, and is soon out the door.

"Coward!" Dean shouts after him, even though the door's already closed.

Dean's eyebrows knit as he asks, "You seriously don't know what that is?" He gestures to the foil packet in Cas' palm, which he doesn't seem to know where to put.

Cas replies, "Should I?"

"It's a condom, Cas. You need to use it if your date gets… intimate."

"Are you referring to sexual congress? The pizza man didn't wear gloves," Cas responds, and Dean pulls a bottle of Jack out of his bag. He takes a swig, realizing he has to teach sex ed.

After a deep breath, he responds, "Cas, it's not a glove. That was just an expression. Pull up a chair – I gotta explain something to you." Dean looks around, and spots a banana on the little round table near the door. He smirks, thinking, 'Good ol' Sammy.' Taking the banana, and fishing out a condom from the box, he steels his expression as Cas pulls up a chair opposite him.

Dean clears his throat: "I can't believe I'm doing this, but here goes: Cas, this is a condom." He holds up the square packet, and takes a swig of Jack before setting it on the bedside table. "People use condoms to avoid getting diseases from sex, or to prevent getting a woman pregnant." He locks eyes with Cas, waiting for the slow nod of comprehension he usually gave; it doesn't come.

"You put on a condom before you have any kind of sex with anyone, unless you both agree not to. And the 'not wearing one' part usually only happens when you and another person have been together for a long time."

Cas cocks his head to the side, and gazes at the packet, confused. "How do I wear a square of foil?" He asks, turning the packet over in his hands.

"It's not –" He sighs. 'Poor bastard', he thinks, smirking a bit.

"The foil part is packaging. The condom is inside. But before you open it, a few tips: Check it for holes. If the foil has any holes at all in it, no matter how small, throw it away and get another one. Second, see the date stamped along the edge? That's the expiration date. Never use one that is past the expiration date. That means it doesn't work anymore."

Castiel nods, attention rapt on Dean now. "So, I checked the packet, and it doesn't have any holes, and it's not expired yet. Now, I'm gonna open it carefully," he adds for emphasis. Dean gently opens the Trojan packet and takes out the condom inside. "THIS is the condom. It's really delicate, so you have to be careful not to scratch it with your fingernails or pull too hard. The condom is just like the package in that if it gets any holes or tears in it, you need to throw it out."

"Dean," Cas asks, "why do you have that banana?"

"I'm going to use the banana to show you how to put it on. Just pretend the banana is a penis, okay? Condoms are supposed to go on there." Dean pinches the top of the condom, and lays it on top of the banana. "Pinch the top like this, so that it doesn't end up being too tight on you. Keep it pinched with one hand, and use the other to roll the condom down." He looks around, finally settling for holding the banana between his knees. He rolls it down as far as it will go, and says, "That's more or less it. Oh, and only put it on after you're… standing at attention."

Cas looks confused again. "I need to be in military stance to wear this?"

"No, I meant – when you have a boner, Cas. Like when you watched the video with the pizza man, understand?" Cas' eyes widen, but slowly, he nods. Dean takes the condom off the banana and leaves it on the bedside table, as he stands up. Cas stands too, and glances at the clock.

"My date's in two hours," he announces, and puts the condom in his pocket.

"Maybe… maybe you should practice then. You know, in case it happens tonight."

"Practice? With the banana?"

"No, practice putting it on yourself. Why don't you think of something sexy, go in the bathroom, and try it out?"

Cas looks unsure, but nods. "All right…" he agrees, "I'll come out when I'm done."

Dean puts the chair away and goes back to cleaning his gun, pretending he can't hear the odd groans or latex snapping coming from the hotel bathroom. His ears perk up when it grows suddenly silent, and then Cas calls out a panicked, "Dean!"

"What's wrong?" He calls, placing his gun on the nightstand.

"I… I think I did it wrong. I'm not sure I can get it off," he responds, sounding alarmed.

Dean rubs the back of his neck with his hand, a warm feeling creeping across his cheeks. "Just roll it off," he answers back, and Cas gives an odd grunt.

"It… it won't come off. It's, uh - starting to hurt…" Cas' voice rises and he sounds panicked, which makes Dean roll his eyes.

He sighs, "Jesus Christ…"

Dean takes a long pull off of his bottle of Jack, and stands. Squaring his shoulders, he pushes open the bathroom door. "You know Cas, this sort of thing is what I was hoping to avoid. That's why I asked you to do it in the bathroom, rather than out there." He gestures to the room, and Cas looks very uncomfortable.

"I'm sorry, Dean. Please, help me…" He gestures to his cock, which looks strangled by the inverted rubber.

"You put it on inside out, and… it's too small for you?" He steps closer, and peers down. "Why didn't you say you needed a magnum?"

Squirming in discomfort at Dean's gaze, he explains, "I don't know what that is…" Dean sighs and reaches down, extricating the rubber, his fingertips brushing the underside of Cas' cock. His breath hitches and he avoids Dean's gaze, his cheeks slowly tingeing with red.

He throws the rubber in the trash, and sighs. "Put your pants on, Cas. I'll get you a magnum and if you get lucky, just ask her to put it on. If she can't, get out of there. You don't want illegitimate children from your first time."

Dean leaves the bathroom, and strides over to the bed. Behind him, Cas gives a distressed "Dean!"

He turns to face the harried man, surprised to find he has shed his pants entirely and stands now in Dean's flannel, the top three buttons undone, and a pair of white boxer shorts barely able to contain his erection. "Yes, Cas?" He underlines his statement with a what the fuck do you want? air.

"Dean, do it again. Please… I can't - it hurts…"

"What are you- ?" Comprehension slowly dawns upon Dean, as Cas' hips keen forward, the look in his eyes far-away but desperate. Dean looks at his bottle of Jack, then back to the man before him. He takes another swig, and beckons Cas forward. "Just… don't tell anybody about this, okay?" Dean's voice is rough, but has a pleading tone to it, and Cas slowly nods, his gaze now back on Dean.

He grabs Castiel's hand and pulls him close, nuzzling into his exposed neck. Cas' breath hitches again as Dean's lips ghost over his skin, making soft kisses up to his ear. He stands there awkwardly until Dean murmurs, "Put your arms around me."

Cas pulls him tight, feeling their hearts beat fast against their chests and his eyelids flutter close as Dean runs a hand down his back slowly. With his other hand, he tilts Cas' chin up, their lips meeting briefly before Cas utters a quiet moan. The sound reverberates in Dean's core, and whether it's the Jack, Cas' pleading look, or a combination of the two, Dean feels a slow warmth creep up his thighs. This time, when Dean leans in for a kiss, Cas' lips are pliant, giving at the slightest pressure. He kisses back, a timid tongue peeking out to touch Dean's lips.

"Okay, just sit on the edge of the bed," Dean directs, pulling back from the kiss. Castiel complies, and Dean settles in behind him, his legs straddling the half-naked man. "I'm gonna show you what to do, so you don't have to ask me next time, okay?"

Cas nods, and Dean continues, "Watch what my hands are doing, so you'll know how to do it yourself." Dean runs a hand from his hip to his thigh, and dips inward, as Cas' eyes follow the trail he's made.

"Okay, open your legs a little wider," Dean instructs, and as he does Cas answers, voice breathless, "Yes, Dean."

Dean's cock stirs at the sound, but he shakes his head hard and forces himself to focus. Dean's hand rubs along the hard outline of Cas' cock, stroking him over his boxers, as his other hand grips Cas' hip. He scoots closer to peer over Cas' shoulder, and feels Cas rolling his hips back against his groin. His bites his lower lip, stifling a shudder, before he orders, "Okay, focus on my words and what my hands do, nothing else." He clears his throat, glad Cas can't see the slow blush spreading across his cheeks, and commands, "Unbutton your shirt."

As Cas undoes the flannel, he asks, "Does having it touched over your boxers feel good? Or does it hurt?"

Cas shrugs off the flannel, answering, "It feels good."

Dean smiles a little to himself and responds, "Good. That's the first step. Only touch yourself a certain way if it makes you feel good. If it hurts, stop."

Although Dean wants to drag this on as long as possible, he knows he should probably hurry this up; Sammy had a habit of bursting in at the most inconvenient times, whether he was alone or with someone.

"Okay, stand up and take your boxers off." As Cas steps out of them, Dean adjusts himself, trying to get comfortable. Cas sits back down, legs splayed wide, with his hands gripping the edge of the bed. Dean strokes down his thigh again, and wraps his hand around his cock. As he begins a slow stroke, he mutters in Cas' ear, "Tell me how you want it. Faster, slower?"

Cas' breath hitches a little, as he answers, "F- faster…"

Dean increases his speed: "Like that?"

"Uhn … Yes," he moans in response.

"Wrap your right hand around mine, and follow my movements," Dean instructs, and he soon feels Cas' smaller hand on his. "Now imagine something sexy. Whatever got you hard in the first place, and build on that image. Make it into a movie in your mind. Get completely lost in it, and in the way touching yourself feels. Pretend it's the other person touching you…"

It's difficult for Dean not to take his own advice, for his mind not to start conjuring up ideas. He shakes his head hard again, and looks down at his hands. "Now, I want your hands to trade places with mine. I want you to touch yourself, and I'll help you out if you still need me to. Otherwise, I can get out, if you want the privacy." Dean figures this is an easy out; he could walk around town until he cools down.

Cas' hands switch places with his, and Dean rests his own on the bed until he gets an answer: "Don't go, Dean. Help me do this, please." Dean lays his hands over Cas' trying to ignore the ache of his own cock as they move, bringing Cas closer to the edge. Cas begins to moan again; "It's starting to ache…"

Dean guides Cas' other hand to his balls, and gently pulls on them. "Does that feel good?"

"Y-yes," Cas replies, his other hand gathering speed. "Dean, I feel funny…" Cas shudders, his breathing becoming more labored.

"You're close, Cas. Do you wanna feel even better?" As if in answer, Cas thrusts his hips up, fucking his fist. "Just keep going, and when you can't hold back any longer, just let go." Cas' hand begins to move at a furious speed as he bucks up his hips.

The timid moans grow in frequency and intensity until Cas is shouting, "Uhn, oh, oh… DEAN!" Dean, stunned, removes his hands from Cas as he finishes bringing himself over the edge; his eyes are glued to Cas' pulsing cock as it spills out of him, cum covering his hands and his stomach. When Cas' stroking finally stops he clears his throat and embarrassed, states quietly, "I, um, made a mess." Dean moves back from behind him and fetches a box of tissues from the nightstand. He hands the box over, not meeting his eyes. After Cas cleans himself he pulls his boxers back on, Dean taking a seat next to him on the bed.

"Cas … Remember when I told you to focus on the words and the hands?"

"Yes, Dean." He turns to look at Dean, but Dean resolutely keeps his gaze straight forward.

"Did you do what I told you, to imagine the thing that got you hard to begin with?"

Cas again responds, "Yes, Dean."

"Then why did you shout MY name just now?"

Cas cocks his head, as if the question makes no sense. "Is it not customary to scream the person's name if they give you sexual pleasure?"

Dean clears his throat, retorting, "Cas, you don't know what you're talking about. I might have showed you how to do it, but you gave yourself that feeling. And no, you don't shout your own name when you masturbate."

"Dean, I learned this 'skill' as a result of being touched by you. I came up to you and begged you to touch me. I don't know how I would have reacted, had you rejected me. I burned with lust for you at that moment, and I burn with it still."

He begins to feel hot under Cas' gaze, and his words certainly aren't helping. "I think you're confused. You only learned what sexual desire even was a year ago. Just because you're human now doesn't mean you should throw yourself at the first person you see. I know I gave you crap about being a virgin before, but sex is… a big deal. Especially the first time. It should be with someone… someone who deserves it."

"Dean, you misunderstand me. I get aroused just by thinking of you sometimes. I desire… carnal union with you."

"Uh, uhm -" Dean holds up a finger, then continues, "Just give me a minute, Cas." He stands up and walks outside the hotel room, dialing Sam's number. "Sam, it's me. What do you got?"

"Dean, hey. So that lead's hit a rough patch, and it's turning in a whole new direction. I'm probably gonna camp out here until the library closes. They have some of these reference books on pretty tight lockdown."

"All right, I'll be here," Dean responds, and flips his phone close.

'Holy shit,' he thinks. 'I can't believe I'm gonna do this.' He scrubs his face with his hand, and takes a deep breath before opening the door. He makes his way back to his bed, where Castiel is still sitting in just his boxer shorts.

"What about your date?" he asks, and Cas waves the question away.

"It is not of import."

"But getting fucked by a hunter is?"

Cas has turned to face him, his legs spread in invitation, his body a stark contrast to his deep blue eyes and guileless expression. "Dean, I just want what you will give me."

All of Dean's reservations fly out the window with that, and he growls, "Lay on the bed." He moves swiftly, scrambling onto the bed and looking up expectantly. The blonde pulls his t-shirt off by the scruff before staring Cas down: "Are you sure you want this?"

Cas licks his chapped lips before replying, "I just… want you to touch me, Dean."

He climbs on the bed, on top of the now-trembling man, taking in the sight below him properly for the first time: Castiel's skin is slightly tan, his hardening nipples a light brown, and Dean is surprised by an absence of chest hair. Although Dean himself is fairly smooth, he expected at least one of them to have some. The limbs winding around him are surprisingly muscular, and he's struck by their strength, given the man's recent terrestrial down-grade. The desperate, easy nature of Cas' want and the smooth skin before him calms the hunter, the territory suddenly becoming much more familiar.

He slots his legs between Cas', the friction of his rough denim against the thin linen boxers almost too much for Cas to bear. He reaches a shaking hand up, cupping the bulge in Dean's pants. The contact causes Dean to jerk his hips forward, as Cas moves his fingers up to the zipper. "Please," he begs, eyes fixed on Cas' hand.

He snaps the button open and pulls slowly on the zipper, Dean's dark red boxer shorts slowly becoming visible. When he reaches the end of the zipper, Dean pulls his hand away, flopping on the bed next to him before Cas can get a word out. His hips arch up as he pulls the jeans down, his breathing suddenly erratic. He kicks them off and turns towards Cas, asking, "Okay?"

"Yes, Dean," he answers, and the blonde dives in for another kiss. When they part, Dean's hands are on the waistband of Cas' shorts, and he pulls them down. As Cas kicks the shorts off, his hands go to Dean, stroking him through the soft cotton of his shorts. Dean moans, his hard length straining against the lone button on his fly. Cas' eyes meet his, and the desperate look he conveys urges the virgin into action. He grips the waistband of Dean's boxers and pulls them off quickly, finesse eschewed in favor of immediate skin-on-skin contact. Cas rolls on top of Dean, rutting their cocks together as he nips at Dean's neck. He gasps, the soft drag of teeth on his tender skin almost too much to bear, his cock twitching against the jerky movement above him. Dean's arms encircle him and he flips them, kissing Cas hungrily. He's been on edge for a while and pushes himself up, trading the sweet friction of their bodies for a moment of clarity. He breathes hard, looking down at the squirming brunette. Cas' look is almost challenging as he stares Dean down - pupils blown wide, chest heaving.

Poised above Castiel, Dean's naked body feels hot to the touch. "I'm gonna ask again, Cas. Are you sure you wanna do this?"

It clicks in Cas' head that Dean needs permission, so meeting those impossibly green eyes, he begs, "Penetrate me, Dean."

And fuck if that isn't the hottest thing Dean has ever heard.

He lowers his body down, their skin pressing together, as Cas' eyelids flutter close again, silently begging for another kiss. Dean's mouth claims his as his arm gropes through the duffel at the side of the bed and he turns to the side, making sure he grabbed the right things: a small truck-stop bottle of lube and a Trojan. Cas looks too, the reality of the situation setting in; he stares at Dean rocking his hips against him, causing their cocks to rub together. Dean sets the items on the nightstand and buries his face in Cas' neck, rubbing his cheek against the hot skin there. His lips brush his collarbone and his tongue licks a gentle swipe over the hollow of his clavicle, tasting so many things all at once: cheap hotel soap, the slight salt of sweat, and the bitter tinge of coffee. He breathes Cas in, willing his body to move against the smaller man below, his arms slow from the soothing presence.

Cas, unsure what else to do mimics Dean's movements and buries his face in Dean's shoulder. His lips glide over freckled skin, taking in the scent of the hunter: salt and the bitterness of barley mingle in his sweat, and the spice of gunpowder clings to him. As the flat of his tongue swipes against the knot of his shoulder, he feels something burn low in his stomach, responding to the blonde's pheromones.

Dean pulls back, settling onto his haunches before rubbing Castiel's forearm soothingly. As he takes a deep breath his hands go to the other's legs, gently pulling them wider from the thighs.

Through half-lidded eyes, he sees Dean's other arm reach forward to the nightstand, grabbing the lube. He watches as a bit is dripped onto his hardening cock and his hips pull back from the cold feeling on contact until Dean's hand moves quickly, stroking up and down the entire length of his shaft. As the hand warms the slick liquid Cas relaxes into the feeling, a choked moan erupting from his throat.

Dean could watch the former-angel's flushed face all night like this, but the dull ache of his cock brings him back to reality. His thumb flicks open the bottle of lube again, and he moves his hand from the shaking brunette, slicking up two fingers. Closing the lube he tosses it aside, using his dry hand to ease Cas' knees up as his slick fingers dip between his legs. As he slowly drags the fingers back, he strokes the tight entrance, willing the muscles to relax.

"Cas, it's okay." Dean's other hand reaches for his right one, his fingers threading into Castiel's. "You gotta relax for me, so I can make you feel good."

Feeling the large, rough hand in his comforts him, the nervousness slowly ebbing from his muscles. He breathes deeply as his eyes settle on Dean's intense expression: He licks his lips, furrowing his brow slightly as one finger makes its way inside Cas.

An involuntary cry escapes his lips, and the muscles tighten against Dean's finger. Dean's other hand moves to his face, stroking his cheek and jaw gently. He leans forward and pecks his lips, before meeting his blue eyes. He holds still, moving only his lips against the other's until Cas slowly lets the tension ease out of him.

"Good," Dean whispers as he drives the finger in to the third knuckle.

"Dean," Castiel breathes out, an edge of discomfort to his voice as Dean works the digit in and out of him.

He struggles to keep his breathing deep, as Dean murmurs encouragement and praise in his ear: "So good for me baby… keep it up." The finger below him adjusts its angle and suddenly, his slightly-softened cock gives a jump.

Cas's breath catches in his throat as he asks, "What did you do?"

"Felt good, didn't it? Do you want me to do it again? It will be easier to touch if you let me put another finger in."

He grabs Dean's free arm, blue gaze piercing as he orders, "Do it."

Dean doesn't need more permission than that, and gently works the second slicked finger into Cas' puckered hole. He watches the anxious expression slowly morph into pleasure, Cas' lids heavy, his lips parted as heavy breaths issue forth. Cas begins to buck up to Dean's hand, willing the fingers to go deeper.

"You think you're ready for me?" Dean asks.

Cas manages to pant out a "Yes…"

He pulls his fingers out, and meets Castiel's gaze, his heartbeat picking up even more when the former-angel touches his chest. Dean tears open the condom packet, and says, "I'm not gonna lie – this is going to hurt. At least at first, anyway." His hand gropes around for the lube bottle as he continues, "But you have to trust me here Cas – I'll do right by you, I swear."

Leaning back on his haunches, he pinches the tip of the condom, slowly rolling it onto him. Cas nods, his eyes glued to Dean's hands as he takes a few deep breaths, willing himself to relax. He lubes his sheathed cock up, and slicks his fingers again, to ready Cas. Despite Dean's previous remonstrations the brunette feels nervous, clenching as slick fingers stroke him. Dean leans down stroking his cheek with his dry hand, soothing him through touch before whispering exciting, filthy things in his ear. His silver tongue then wraps around Cas', the rapturous kiss finally relaxing him.

Dean pulls back and he lines himself up making a first, tentative push in. At this, Cas gives a pained groan, his eyes growing wide. Dean leans forward, burying his face in his scruffy neck, his hand travelling from Cas' knee to one of his balled fists, now gripping the sheets fiercely. His fingers stroking the back of Cas' hand until it relaxes, Dean instructs, "Breathe."

He wraps his hand in the trembling one below him, Cas attempting to deepen his breath until the tight feeling in his chest leaves him. He blinks back tears as Dean smiles and kisses him, gently pushing in until he bottoms out inside of him.

He lies there holding Cas close as he whispers reassurances in his ear. Even in his relaxed state, Castiel doesn't trust himself to speak, afraid he will cry out. He feels a hand squeeze his own, and Dean meets his eyes, asking, "Can I move?"

A small panic flutters at Castiel's throat, which Dean is able to ease by kissing his neck. Cas manages to nod, as Dean's eyes once again meet his. He pulls back a little, and then thrusts back in. As he moves, his eyes never leave Cas, reading his face for the smallest bit of discomfort.

Dean's gaze now seeks encouragement as he builds up a rhythm, Cas quietly gasping. He shifts his hips a little and thrusts, a low moan escaping Cas' throat. After repeating the action Cas squeezes his arm, bucking his hips up into the feeling. He runs his hand over Cas' hip, murmuring in his ear, "You like that?"

As Dean rolls his hips Cas nods, his cock twitching against his stomach. He whispers into Cas' ear, "I told you I'd make you feel good," and rolls his hips again, dragging a lustful cry from the man's throat.

Cas' breath is heavy and uneven as he tries to press their bodies together, needing friction on his once – again hard cock. Although still achingly tight, Cas has opened up a little more, and Dean heeds this sign to quicken his pace. With each smooth roll of Dean's hips, Cas can feel his control waning, his head swimming. Dean's also struggling to hold back, as each sound he forces from Cas' lips makes his cock twitch.

Cas' eyes widen, a look of panic sweeping across his face. "Dean, I-" He starts, cut off by the sound of another small groan escaping his lips. He licks his lips and looks down, rolling his hips against Dean's stomach.

A small smile plays at the corner of Dean's mouth as he asks, "Are you getting close?" He bites his lip, his brow knitted as he nods in response. With that, Dean shifts position, thrusting shallowly and wrapping a hand around Castiel's aching cock.

He begins to stroke in earnest and soon has Cas puffing out shallow, erratic breaths. "Come on, Cas," he coaxes, wrapping his other hand in Cas'. "It's okay, just let go…"

The roll of his hips hitting Cas' prostate once again, Cas gasps out loud as his hips arch off the bed. "Come on Cas, cum for me," he urges.

His skin slick with sweat, he thrusts up into Dean's hand. "Come on, Cas," he pleads, and he watches as blue eyes grow wide.

He pulls Dean closer, the grip on his bicep tight. Dean moves his hand as Cas starts, "Dean, I'm going to…"

Moving his hands to Dean's shoulders, his nails digging into his back, Cas cries out, "Dean!"

Rutting up against him, his whole body tenses as he moans throatily in Dean's ear. He twitches as he comes, the warmth rubbing between their stomachs. Cas rides out his orgasm forcefully, and slowly begins to sink into the bed, exhausted.

Growling "Fuck, Cas," in his ear Dean thrusts deep, unable to hold on any longer. Dean trembles on top of him, his arms scarcely able to hold him up as he rides it through. His eyes fly open, his amazed gaze focusing on Cas' blushing face, cumming hard.

Finally, the jerky rutting of his hips stops. Arms trembling and breathing hard, he sits back, carefully pulling out. The hand that's holding the base of the condom carefully rolls it off and stuffs it into the condom wrapper, before tossing it in the trash. He stretches out onto his back next to Castiel and looks over at him, smiling. Dean watches as a slow smile creeps across Cas' face, and huffs out a breath.

He sits up, searching for his boxers. Finding both pairs tangled in the covers, he tosses Cas' over, before standing up, about to step into his own. Cas regards the undergarments for a moment before balling them up in his hand and slowly sitting up. He makes his way to the bathroom and starts the shower. Dean looks down at the boxers in his hand, and then slings them over his shoulder. Quickly making his way to the bathroom, he asks, "Can I join you?"

Cas walks out of the bathroom, toweling his hair dry as he walks around the hotel room, shirtless. He walks over to the window and opens it, trying to clear the room of the smell of sex. Dean pads out of the bathroom towel slung across his hips, and glances over at his bed. He shrugs his shoulders and makes the damn thing, tossing the bottle of lube back into his duffel. Cas sits at the table, just watching Dean dress with a goofy smile on his face. Dean tosses Castiel's shirt at him; and as he does the last button up, the knob turns.

Dean kicks his duffel under the bed as the door swings open, and Sam strides through the door. "Hey, Dean. Cas? Aren't you supposed to be out on a date?"

He looks down to check the time on his phone, as Cas replies, "She cancelled."

Sam kicks off his shoes, and sits down on his bed. "Bummer. You okay?"

Cas gives a small smile, answering, "Yeah. To be honest, I guess I didn't like her that much."

Sam nods and looks over at Dean. "Guess all that 'birds and the bees' stuff was for nothing, huh?"

"I don't know about that," Dean replies. "I'm sure Cas will get another chance."

Sam chuckles at Dean, and Cas begins to blush. He quickly excuses himself and leaves the room. "You embarrassed the poor guy," Sam chides.

"He'll be fine," Dean responds, and turns over. That night, Dean sleeps for eight hours – the first time in years.