A/N: Hey there! I know there are probably a lot of fics with this same premise but after I watched Free to Be You and Me, I just had to write this. Cas and that prostitute was too funny. Please R/R, this is pretty much my first, and most likely last sex scene. I just found it difficult to write. Minor spoilers for Episode 5.03

"Jesus Cas!" Dean exclaimed after he flicked the light on in his cheap motel room, revealing Castiel sitting on his bed, head in his hands. It was nearly midnight and Dean was exhausted after the escapade in the brothel.

"You scared the crap out of me!"

The angel slowly looked up from the spot on the floor he was staring at intently to meet Dean's eyes.
"I am sorry, Dean."

The hunter sighed, remembering that Cas's chances of living through their encounter with Raphael tomorrow were slim. "It's okay, Cas." He dumped his duffel bag onto a chair in the room and leaned against it. "Just stop surprising me like that. One of these days I might accidentally punch you in the face or something," he said with a smirk.

"I doubt that you would do me any damage."

Dean laughed, remembering the first time he tried to punch Castiel.
"So what are you doing here anyway? I thought you just poofed off to wherever it is you angels go when you're not hanging around on Earth after what happened at the brothel."

"Dean, you know that I am cut off from the power of Heaven," Cas sighed with a downtrodden look, weariness instantly making its presence known in his features, his body posture noticeably drooping. "I cannot leave the confines of the earthly realm."

"Oh... right."

They sat there in awkward silence for a few awkward moments. Castiel went back to staring at the floor, not offering any more information as to why he was suddenly in Dean's motel room sitting on his bed after unceremoniously leaving when they were talking in the Impala. Finally, Dean couldn't stand it any longer. "I'm going to have a beer. You want one?"

"No thank you. I'm fine," Castiel answered stoically.

"Well, I need a beer." Dean got up and went to the mini fridge. He grabbed a beer, popped the top off and then went to sit down next to Cas on the bed.
Cas scooted over uncomfortably, suddenly aware of how close the proximity of their bodies was on the bed. Dean chose to ignore this, instead planning to interrogate Cas until he told him what was up.

Before he could get one word out, Cas said, "I am afraid of dying." Dean sat in silence for a few more moments, unsure of how to comfort his friend.
"I know that we have not known each other very long, but I am grateful that you tried to make my last night memorable, even if I did mess it up. It seems that human women are not really in my area of expertise."

Dean cleared his throat and spoke. "It's not your fault, Cas. In retrospect it does seem innappropriate to have taken an angel of the Lord to a brothel." He smiled weakly at Cas. "I just wanted to make your last night a good one. And come on, how could I let my best friend die a virgin?"

Cas looked up, surprised. "I am your best friend? I thought Sam was."

Dean grimaced and took a swig of his beer. "Well, not anymore." he said.

"Again, I am sorry. It seems I always end up just upsetting you." Cas said quietly.

Dean's expression softened as he looked at his friend. "Hey, you know, I actually had a really fun time tonight, even if things didn't go as planned. but they never usually do, do they?" He stared at Castiel in the dim lighting of the grimy motel room.

"Dean..." Cas said.

"Yeah?"

"I would not like to die a virgin if I can help it, and you did promise me. I would like to experience what it is like to be human at least for one night before I go."

"Well, ok, I guess we could go out again, or call an agency or something..." Dean trailed off.

Cas fidgeted on the bed. "Actually, I do not think I would enjoy engaging in sexual intercourse with a...woman." he finished.

Surprise splashed across Dean's face, and his cheeks were painted red with his blush. "Oh! Well...that's fine, Cas, it doesn't matter to me who you..um...I..uh...you should have told me earlier." Dean stammered.

"I was worried that you would find me repulsive for having such urges."

"No, of course not...I mean, we've all...thought about it at one point or another." Dean cleared his throat and looked away, his blush still clearly visible in the low light. He could not believe the awkward turn this conversation was taking.

Dean jumped as he felt Cas's surprisingly warm hand brush over his own and grasp it tightly. "What are you doing?"

"Showing affection. I have observed many couples clasping their hands together out in public."

"Cas, I don't, I mean, I'm not...I'm not gay!" Dean stared dumbly at their entwined hands on the bed, not pulling away though.

"I was not suggesting that you were. Perhaps you are bisexual because of your apparent interest in both women and men."

Dean snapped out of his stupor, removing his hand from Cas's. "I'm sorry, but I only like women, Cas."

"But you said you thought about being with men."

Shit.

"Well, I just..um.." Dean swallowed. Castiel scooted closer on the bed, worked up his courage, and took Dean's beer from him. He set it down on the small table in the room, but when he turned around to the bed, he found that Dean had retreated to the bathroom. Castiel heard the shower start up and sighed.
Some last night on earth this was turning out to be.

Cas decides to wait on the bed. He stretches out, lying back on the pillows. Dean has to come out sometime, he thought.


Well, sometime turned out to be almost an hour until Dean emerged from the bathroom. "Oh hey, you're still here." he said, halfheartedly.

"I wanted to finish our conversation. As you know, it is likely it is my last night and I would appreciate some closure with you."

"Closure with me? Don't you have something better to do on your last night?" Dean snapped.

"Dean, I can think of nothing more important than spending my last hours with you."

Dean found himself once more dumbstruck by the bluntness of the angel. "Can I ask you a question Cas?" he asks softly.

"Of course Dean."

"What is it about me that's so special? Sam once told me that Uriel said you liked me. Why do you? Why me?"

Cas smiled uncharacteristically. "I do not know, Dean. It's just that since I pulled you from Hell,...you seem to be the only human that I feel particularly drawn to."

Dean laughed uncomfortably. "Well you're the only angel I feel drawn to." He stopped abruptly when he realized it was true. He did feel drawn to the angel. Whenever he popped up out of nowhere, Dean recalled his stomach doing somersaults. He had just shrugged it off then as nerves and stress of the job, but what if it was something more?

Cas looked at Dean tenderly. "Sorry, but I could not help overhearing that."

"Hey, stay out of my head you perv." Dean tried to laugh it off, but a bundle of nerves were knotting in his stomach. He sighed and lay down next to Cas on the bed. "Man, why did you have to make things so complicated? You could have just left me in the pit and then I wouldn't have to deal with all of this..feelings stuff."

"Please don't joke about things like that." Cas looked at him with his signature serious expression.

Dean gazed back, into those electric blue eyes. "I'm sorry." He reached a hand out and experimentally brushed Cas's hair behind his ear. Cas stared back at him hard, sliding a hand up Dean's side to his shoulder, the one with his mark on it. "You know I'm glad you gripped me tight and raised me from perdition." Dean smiled genuinely. "The least I can do is make sure my savior doesn't die a virgin." Cas gasped as Dean leaned in close and claimed his lips in a soft, tender kiss, his hands caressing Cas's face. All too soon Dean broke away for air. As soon as he seemed to regain his breath, Cas leaped on him, pinning Dean's arms to the bed. He closed the distance between their mouths quickly and engaged Dean in another kiss, this one full of passion. Dean's instincts kicked in and he rolled them over together on the bed, trying to gain dominance. His tongue pressed on Cas's bottom lip, asking for entrance. Cas acquiesced, opening his mouth for Dean's tongue to explore.

Dean's hands wandered down Cas's body, or rather, Jimmy's body, until his hand brushed against the bulge in his trousers. Cas made a strangled noise in his throat and Dean pulled back from the kiss, licking his pink lips as he stared in Cas's dark, lustful eyes.

"That's...new." Cas said breathlessly.

"You know I'm just getting started." Dean ground his hips into Cas's, rubbing their erections together and eliciting low moans from both parties.
Dean moved his hands to shrug off Cas's trenchcoat and jacket. Then he undid Cas's tie, slowly slipping it from his neck and tossing it behind him onto the floor, and moved on to the buttons on Cas's white shirt, hands shaking in his excitement and nervousness. I can't believe i'm about to do this, he thought. And with an angel, no less.

Cas grabbed Dean's hands, halting him in his task of undressing his angel. "You know you don't have to do this just to placate me, right Dean?"

"I know that, Cas. But I want to do this...I want to. I want you. It's just that...I've never done this with another man before."

"You seem to be doing pretty well so far." Cas gazed at him with a look of such admiration and raw desire that Dean could not help the groan that escaped his lips. He felt a spark of electricity pass through his body as he leaned down to kiss his angel again. His angel. His.

He finished undoing the rest of Cas's buttons and slid his hand up Cas's chest. He pinched his hard, dark nipple and Cas arched his back, pleasure overwhelming his body.

"Cas you kinky bastard." Dean smirked as he ran his thumbs over Cas's nipples, eliciting some obscene sounds from Cas's mouth.

"Let's see how you like it," Cas panted, flipping them over once again so he was on top. Taking a page out of Dean's book, he rolled his hips into the hunter's and sent another jolt of white hot heat to Dean's already straining cock. Dean whined, aching to touch himself.

He moved his hand to undo his belt, but Cas stopped him with his own. "Let me take care of that." Dean stared at him. "Cas, do you even know how to...?"

"Oh please, Dean, I'm a virgin, not an idiot." And with that, he gracefully slipped Dean's belt off and discarded it on the floor with the other clothes items. He slid his fingers inside the waist of Dean's jeans teasingly. Dean growled seductively. Cas undid his jeans, relieving some of the pressure, and slid them down mid thigh. He stared at the obvious bulge in Dean's boxers that left little to the imagination. With little warning, he pulled them down as well and took Dean's aching member in his hand.

"Oh, Castiel."

Cas slowly stroked Dean's length, savoring the sight of Dean writhing and whimpering beneath him.

"Ok Cas, ok." Dean grasps his arms. "How do you want to do this? You're calling the shots here apparently."

Cas lowered himself until his mouth was on Dean's ear. He whispered dramatically, "I want to feel you inside of me."

"Oh God," Dean choked. "Sorry," he added. "Force of habit."

"That's fine. Hurry up and fuck me already." he said, deadpan as usual.

"Boy, you really are something different. I never thought in a million years I would be doing something like this." Dean rolled out from under Cas and went to his bag for a condom and a bottle of lube. He pulled his pants and boxers off completely along with his t-shirt. Cas could not help but stare unabashedly at him, drinking in his toned and muscular body. He noticed that Dean had accumulated some new scars since he had raised him from Hell, and of course, there was his mark on Dean's left shoulder, he noted, pleased.

Dean stalked back to the bed. "Hey, come on, am I gonna be the only one naked during this? Cuz I don't think that's gonna work." Cas sat up and Dean eased his shirt off his shoulders. Cas then fumbled with his belt, eager to be with Dean finally. he gave up and let Dean do it, his hands seeming to not want to work properly for him at the moment. Dean laughed at him again, a beautiful, mirthful laugh. Cas had never heard Dean laugh so many times since they had met a year ago. I'm the reason for his happiness. Me. This thought filled Cas to the brim with his own happiness, and he pulled Dean to meet his lips yet again as he slid his trousers down and his boxers as well, leaving nothing between them. Just skin on skin.

Dean opened up the condom and slipped it over his rather magnificent cock, in Cas's opinion, and then he smeared some lube onto his hands and newly sheathed cock. He then grasped his new lover's cock and lightly slid a single finger up and down Cas's length. With his other hand Dean lifted up Cas's hips to get a better angle and fingered Cas's entrance. "Ready?" he whispered. Cas nodded, unable to find any words at the moment. Dean slid his forefinger knuckle deep into Cas as the angel hissed in pain mixed with pleasure. "Is that okay?" Dean asked. "Just keep going. Don't stop." Cas pleaded. "Ok you asked for it."
Dean pressed in all the way, moving in and out in time with his hand on Cas's cock. He slid in a second and then a third finger, working Cas's entrance until he was confident that the angel was ready. He removed his fingers and shifted up Cas's body, positioning his cock right against Cas's hole.

"I need to feel you in me NOW Dean." Cas gripped his lover's hips almost as tightly as he did when he raised Dean from Perdition, and Dean eased himself slowly into his angel, enveloping himself in the tight heat that was Castiel. "Wow. Ugh, Cas. This feels amazing."

Cas thrust upwards, unable to control his body. "Please move, Dean. Please."

"Of course, my angel," Dean said playfully.

"Bastard." Cas moaned as Dean snapped his hips sharply, ignoring his original promise to himself to go easy on this virgin and decided to just ravish the sexy angel, with his messy black hair and his adorable, breathless cries.

Dean continued to pick up the pace, mercilessly pounding into Castiel as he rocked up in order to meet Dean's thrusts. All of a sudden Cas cried out as Dean hit his sweet spot. "Good God what was that!?" he exclaimed. "I'm guessing your prostate." Dean panted. He was so close, the pressure building up in his balls quickly. Cas moved his hands up to Dean's ass and pulled him impossibly closer each thrust in, hitting that same spot deep inside Cas each time. "Dean I feel...something's happening. Oh God Dean Dean DEAN!" Cas came and white, hot liquid shot from his cock, coating Dean's stomach. After a few more thrusts, Dean went over the egde as well and came deep inside of his angel, crying out his name as he did so.

Dean slumped over the spent Cas, utterly exhausted. "Dean...what was that?"

"Congratulations, Cas." Dean pulled out of him and lay down, resting his hand on Cas's chest and feeling his racing heart. "You just had your very first orgasm."

"Thank you, Dean. That was...indescribable."

"You don't have to thank me, Cas. I should thank you. I think I would have regretted not having sex with you of you...you know, die tomorrow."

"Well, you don't have to worry about that anymore."

"Oh, why not?"

"Because there is no way I am dying now that I am sleeping with the most beautiful man I have ever met."

Dean smiled, still amazed at Cas's candidness and honesty. He grasped his lover's hand and promised he would never let go as he drifted off next to the one being who made him happiest in the entire world.

"Don't worry, Cas, " he mumbled drowsily. "I won't let anyone take you from me. I'll move Heaven and Earth, if I have to."

"I know you will, Dean," Cas said quietly with a soft kiss to Dean's cheek. "I know you will."