"Really?... Well, you're very up-front about it, I can respect that." Dean replied. "But here's the thing, I'm pretty open minded and all, but he's my brother, so... that's not going to work."

She was still grinning. "Okay... Got any cute friends, maybe?"

Dean wracked his mind. He was almost surprised how quickly a certain angel came to mind. "You know what, let me go call somebody. I'll be right back."

Dean stepped outside of the bar, putting his phone up to his ear. "Cas! Hey! Listen... I uh, I need a favor. And this is a pretty big favor."

"Of course, Dean." Castiel's voice came from the other end of the line. "What do you need?"

"Just meet me at the Hapsburg Inn on 180, room 223. I'll explain when you get there."

Dean slid his key card and propped the door open with the swinging bar lock.

Castiel was sitting at the table. "I came straight here, you sounded urgent."

"Yeah, well, nothing bad, I promise. Listen, I need your help with something."

Castiel was looking right at him. Dean felt a twinge of guilt. "Oh, man, how do I explain this... There's a girl on her way here, okay? And she, um... she wants to have some fun. With me. But not just with me, she wants... uh... Extra, fun... Like..."

"Sex, but with multiple partners?" Castiel finished for him in a flat voice.

"Yeah." Dean admitted, sheepishly. "Obviously I'm not doing that with Sam, and I couldn't think of anyone else in the area."

"Dean, I may not be a virgin, but my experience is sorely lacking. This may be a bad idea." Castiel said, shifting uncomfortably.

Dean nodded, "Yeah, well, first time for everything, right?... Look, I'm desperate, man, it's been months, okay? Or I wouldn't have called. I can walk you through it, and you might learn a few things. Might even have a good time, huh?"

Castiel was quiet. "My experience with April was... very pleasant. Until the torture, anyway."

"I promise, no post-coital torture this time." Dean said firmly, before softening his voice. "So, is this okay with you? And you know, you can stop any time you want, if you change your mind. That's okay to do."

Castiel was visibly nervous, but nodded, looking away. Dean was about to attempt to say something reassuring, but there was a soft tapping at the door.

"Anybody home?" the woman from the bar ducked her head in through the door. Seeing Dean, she slipped inside, swinging the lock bar into the room. "Gosh, you didn't tell me he's as hot as you," she said with a slightly drunken giggle.

"Your lucky night, I guess." Dean said, throwing her a charming smile. "He's just a little nervous."

"Because of me? Well, I'm sure I can fix that." she said, setting her purse down, and approaching him. She started to paw at the many layers of clothing over the sides of his chest. "What's it gonna take to get you out of these?"

Castiel looked at Dean and swallowed nervously. Dean simply gestured toward her, in a 'go ahead' motion.

Before Castiel could figure out what it was he was supposed to do, she put her hand across the back of his neck, pulling him down to kiss her. After a few moments of being frozen in place, and another nervous look at Dean, he started to kiss back. She pulled slightly at the back of his collar and curled the first finger of her other hand to Dean, beckoning him, and making it very clear what she wanted, giving the collar another tug.

Dean stepped closer to stand behind Castiel, and reached in front of his shoulders, easing his coat off down his arms as she continued to keep his face preoccupied. She let go of Castiel's neck again to give Dean a clear thumbs-up, before moving to loosen his tie.

Dean took Castiel's jacket as well, since he didn't seem to mind, setting it and the coat over the back of a nearby chair, and dragged out of his own jacket and over shirt with far less care.

She broke away, taking a small gasp as as she did, catching Dean by the arm, and guiding him to stand behind her. She pulled her long, red hair over one shoulder, giving him access to her neck as she pulled Castiel close again. Dean dropped his mouth to her neck and shoulder. His forehead bumped against Castiel's shoulder as his mouth moved.

Dean ran his hands up her sides slowly, before it dawned on him that Castiel was still holding back. He took hold of Castiel's wrist and brought his bewildered hand to her ribs, dragging it slowly and gently up to cup her breast, and moving it in a small, gentle circle. After a moment Castiel took up the rhythm of movement Dean had encouraged him to take.

She took Dean's hand from her hip and brought it to the buttons on Castiel's shirt.

"Don't tell me," Dean said, dragging his lips up the side of her neck, trying to ignore the fact that Castiel's face was so close. He nipped her earlobe and spoke quietly. "You have a thing about getting guys to undress each other?"

Castiel's eyes flashed to Dean before assuming he was supposed to mimic Dean's avoidance, and he looked away, delving into the loose red curls, finding her jawline.

"It wouldn't be much fun for me at all if you guys just ignore each other the whole time." She said, her voice deepening with stifled moans. Dean shrugged one shoulder and went to work on Castiel's buttons, starting at the top.

She slipped one hand behind her, palming him through his jeans, as her lips met with Castiel's collarbone. Dean let out a comfort hum at the warmth of her hand.

With his free hand, Dean moved Castiel's hand from her breast to her ass, and slipped his own hand into the top of her dress, pulling the strap down her shoulder. She shuddered and gasped against Castiel's skin as Dean found her nipple, her hand giving Dean a squeeze.

Dean reached the last button at Castiel's waist, and leaned back a bit, unzipping the back of her dress slowly, his eyes following the curve his hand made along her spine. When he looked up, Castiel's head was tipped back, and his eyes closed. Her mouth was still on his chest, and her hand slowly making it's way to his belt.

Dean leaned in, reaching past her, and unfastened Castiel's belt and pants before she could get there, before dropping his hand to her thigh, running up it slowly, curling his fingers just to the inside of her thigh as she reached into Castiel's pants. Whatever she was doing was certainly working for him. Dean just hoped it wasn't working too well.

Dean stroked over her pubic bone, continuing up to her tight stomach, as she bucked back against him. Yep, that was definitely the back of Castiel's hand against his crotch. Dean tried to block it out.

"Cas, why don't you go ahead and get on the bed? Clothes off. I gotta get something." Dean said, letting go of her and stepping back to peel off his shirt, kicking out of his boots.

Dean considered the box as he pulled it out of his duffel, and a conversation about protection Castiel hadn't understood. He hadn't even gotten this woman's name at the bar... And if he had to explain this to Castiel, or worse, tell him how to put on a condom right now, she would probably bolt. He felt guilty for not having this discussion with Castiel sooner, but it paled in comparison to what could occur without it. Dean wasn't sure angels could contract anything, but he asked for his help. This was on him.

Dean slipped his jeans off and headed to the bed. Castiel was sitting in the middle of it, and she was guiding his hands to remove her dress as she continued to kiss him. The dress came down over her bare ass, leaving her in nothing but her strappy gold heels. She moved to the far side of the bed, climbing over Castiel as Dean sat down.

"Cas... lean back, I'm gonna put this on you." Dean said quietly.

Castiel picked up a hint of concern and leaned back as she shifted a pillow behind him.

She got up onto her knees, guiding Castiel's hand between her legs as she alternated kissing him and turning to watch. Dean opened one of the condoms, and torn between watching Castiel for permission and pretending this wasn't happening, he gingerly applied it, pinching the tip, ignoring Castiel's pleasured flinching and shuddering as he unrolled it slowly down his shaft.

Dean looked up to see her leaning into a kiss on Castiel's mouth, his fingers playing gently between her lips elsewhere, and in a moment of snark, declared, "Okay, honey, hop on."

Suddenly she swung a leg over Castiel's body, turning to face Dean. "I'm actually really close right now, if I get off fast, I'll be able to go longer after."

Dean nodded, "Okay, sounds good, let's do that."

She lowered her body onto Castiel's, impaling herself with his hard length, giving a moan. "You gonna help me with this? Touch me?"

Dean got up on his knees, moving to kneel between Castiel's legs and kissed her deeply, the thought briefly crossing his mind that Castiel's tongue had been in the same place moments before. It was starting not to bother him.

Dean pressed her back, laying her down over Castiel's body, careful to hold his weight off both of them. He worked his way down her torso quickly, but still giving her body plenty of attention as he moved lower.

Dean pulled her knees up from the bed, and dropping his lips down to her slick folds, began to unbuckle her shoes. He lipped and licked at her outter lips, swirling his tongue between them for a moment before taking a mouthful of flesh in to give a strong, brief suck before getting a little more selective.

Her hips were rocking at this point, not by much, but noticeable. Dean spared a glance upward at the sound of a particularly good moan to find Castiel's hands wandering her body. One fell to her hip, flexing fingers encouraging her movement as his lips made his way along her neck.

Dean shook away a thought, wondering what it felt like. Good, if the sounds coming from her mouth were any indication. He took her clit between his lips, rasping his tongue over it quickly before moving it thickly over every inch of her he could manage.

Dean closed his eyes, letting his hand wander into his boxers, enjoying the grip of two hands tangled in his hair, trying not to think about the fact that they seemed to be attached to two different people.

She was certainly right about being close, it was no time at all before she tightened down on Castiel, strained moans broken only by her panting breaths.

Dean pulled away as she sat up, tugging him closer, kissing him, running her tongue over his lips. "That was nice... I'm sure he's good and wet now, I want to get you in here for a turn."

Dean nodded, "Yeah, I can't wait..."

He helped her lift her weight off of Castiel, shifting to take him in further back. It took a little longer for her to settle herself this time, and Castiel made a tiny noise in the back of his throat as she did.

"You okay, Cas?" Dean asked over her shoulder as he took off his boxers.

Words failing him and lower lip thoroughly caught between teeth, Castiel gave a few quick nods.

Dean soon had a condom on himself, and leaned her back again, gently. Castiel stroked her hair away from his face as she went, craning to kiss the side of her neck.

Slowly, Dean lowered his hips to hers, sliding into her carefully. She moaned quietly, but against the hand he had on the mattress, he could feel Castiel shiver as he moaned against her neck. Dean wondered at the fact that she felt tighter than what he was used to, but as he started to move, he realized what he was feeling was a firmness below him that had to be Castiel.

Castiel had pulled his knees up on either side of Dean's hips, and although mostly weighed down, was attempting to move. Dean couldn't tell if he was trying to match his rhythm exactly, or compliment it, but it didn't seem entirely voluntary.

As Dean began to pick up speed, she wrapped her legs around his waist, reaching back to grasp Castiel's shoulder. There was more freedom of movement now, as she lifted some of her weight to Dean's hips, but there was a discrepancy he could feel. There was far more friction between her and himself than what was happening below him. If it were just the two of them, it wouldn't have been an issue.

Dean shifted his thrusts, burying himself inside her, and rocking against her, hard, moving her up and down Castiel's length.

Castiel moaned deeply at the change, echoed by the woman between them, his hands frantically searching her flesh with some unknown goal. Between panting, Dean could hear it, a few muttered words in Enochian... that was probably a very good sign, but a very bad idea, given present company.

Dean shifted his weight to one arm, continuing to thrust, in much longer movements than he was used to, as he attempted to get Castiel to shut up. He only knew what worked for him. He ran his hand up Castiel's ribs, slipping under her shoulder to find his nipple, rolling it between his thumb and finger.

'Crap, now he's even louder...' Dean thought, thankful she was distracted, and not being too quiet herself.

A string of Enochian words were cut off by a strained, open mouthed moan. He could tell without a doubt Castiel was close. But the glow in his friend's eyes- and she was starting to turn as though to look for his face. Crap... And the Enochian was getting clearer...

Dean thrust harder, lowering his head over her shoulder, claiming Castiel's mouth, swallowing his moans, and... 'Damn, he's actually a good kisser... Holy crap, I'm fucking Cas... through a girl, but, still...'

Castiel's hand grasped Dean's upper arm in the same place he'd marked him years before, as he climaxed, biting down gently on Dean's lip and giving a broken whimper as he shook slightly. Waves engulfed Dean, grasping and pulling at him inside her.

Dean pulled back rather surprised at his own actions to find another face looking up at him. Dean suddenly realized Castiel wasn't the only one he'd brought to completion, but the only one he'd been focused on pleasing.

"Oh, that was incredible..." she moaned. "That was so good... but you're not done yet, and I'm getting sore. Let me up, I think we both owe you one."

Dean slipped out of her as she untangled her legs from his torso. Sitting back on his heels, he watched as she slowly slid Castiel out of her body, quickly grabbing the condom from him before it could become an issue, muttering an apology at Castiel's surprised yelp before tossing it into a wastebasket near the bed.

She guided Dean to lay back, his head on the corner of the foot of the bed, running her hands over his muscles, damp with sweat. She waited until Castiel had righted himself, sitting up and moving one of his legs out of the way before turning to him.

"Pay attention, because I'm going to test you on this." she giggled. "You pass, and you get a treat, got it?"

Castiel nodded, obviously confused.

She lowered her head, taking Dean into her mouth, sinking down around him before coming all the way up to run her tongue in circles over the tip. Dean moaned at the warmth and let his head fall back. He grasped at the sides of the mattress as she ran her hand from the inside of his knee down his thigh, making him gasp as she fondled his sac.

Heat building throughout his body, he whimpered as she suddenly pulled away. She pulled the condom off him, starting to reach for the box. "Your turn."

Hot, and wet... Very hot and wet. And moving...

"Well, someone's an eager beaver. Guess you don't want this..." Dean looked up out of his haze. She was stroking Castiel's hair back from his face, another condom in her hand. She turned to look at him. "Let me know when you're close, sweetie, I'm going to make it good."

Dean barely nodded before surrendering to his nerves. He felt Castiel pull up and risked a glance. "Holy..." he breathed, as Castiel moved his tongue over Dean's bare flesh just as she had shown him. Dean shook hard, panting as he lowered his head to the mattress again.

With a few more strokes, something changed. More intense. Dean felt Castiel's hand moving up his body in a shaky manner, barely making it to the bottom of his ribs before clenching slightly, as he gave a nasal gasp, trying to keep his rhythm.

Dean gathered what wits he had left, as most of them had migrated into his dick, and consequently into Castiel's mouth, and raised himself onto his elbows.

Dean had felt it as Castiel moved between his legs after he started, but he hadn't expected seeing his friend's naked body working solely on his pleasure to be this big a deal. Dean's eyes made their way further, and found what had changed. Her hands were between Castiel's legs, having guided him to lay his hips to the side, and lift the upper knee. Her fingers seemed to be everywhere at once. Dean wondered vaguely how Castiel could continue to focus on him so thoroughly, considering.

Eyebrow wiggle... what was happening now?

She had taken a condom out, and somehow gotten it onto her slender fingers without stopping. She reached out of Dean's line of vision, and he was sure he knew what was happening, but not whether Castiel was agreeable to having it happen.

As she entered him, Castiel clamped down on Dean with his mouth, tongue firm to the roof of his mouth, squirming, and moaning around him. Dean was about to tell her to stop, but his words were cut off as Castiel began to suck at him furiously, fingers fanning over Dean's ribs. Dean watched as Castiel's hips rocked against her hands, and moaned louder around him. Hot, wet, and vibrations...

Dean stroked the back of Castiel's hand, staying up on his elbows, watching the entire thing. He wanted to see this. Needed it.

Castiel's rhythm improved as she sped up, giving him something to match. Dean shook slightly as Castiel brought him close, unable to keep quiet as a loud, open mouthed moan escaped him. This only seemed to encourage Castiel. There was no question, they were both on the edge, and it was only a matter of moments. The thought crossed Dean's mind, who would finish, or more correctly, be finished, first?

"Wow..." she said quietly, still intent on her actions concerning Castiel's body. "Doesn't he just have the prettiest eyes?"

Castiel, shaking hard, now, looked up, meeting Dean's gaze, clenching suddenly at his ribs. It was too much for both of them.

Dean's body exploded hot within Castiel's mouth as said mouth, still moving frantically against him loosened, and he began gasping through his nose. Dean shook hard, watching every movement, slips of white escaping Castiel's lips, swallowing against him, glimpses of his tongue, at the same time shaking as he coated her hand.

Dean barely held it together as she pulled her hands away, causing Castiel to jerk before he rolled over Dean's leg, stretching out on the bed, a fresh fucked mess and a thing of beauty.

He heard something fall into a wastebasket, and the sink ran for a few moments, indicating she had left the bed. He could almost track her as she crossed the room.

"Well, I've got an early meeting, so I have to go, but... daaamn, you guys were a lot of fun." she said, pulling her hair out of the neck of her dress as she pulled up the zipper, grabbing her shoes and purse, and making her way to the door. She paused to take a lollipop out of her purse, just enjoying the sight of them stretched out over the bed, before turning to leave, "I'll see you around, fellas..."

As the door closed behind her, Dean's gaze slowly drifted to Castiel's spent form. "Dean, I... I hesitate to ask, but-"

Dean wrapped his arms around Castiel, pulling him into a snug, but gentle embrace.

"Better?" Castiel nodded against his shoulder, wrapping an arm around Dean's waist. "Yeah, me too."

Outside, in the hallway, she shifted into a form they both would have recognized.

"'Bout damn time! Heh. Losers." Gabriel smirked, popping the candy back into his mouth as he walked away.