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Beautiful Chaos

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Chapter 1

 

Dean was fucking lit and torn at the same time. The bullshit ultimatum Ezekiel gave him was just that. Bullshit. Cas came to bat for them time and time again and having to either kick him out or possibly lose his brother… He hated himself a little bit for knowing he’d always choose Sam.

 

It was tempting to flip Ezekiel off and take his chances. But Dean knew better than to play with that fire. Instead, he made his way to the library, where Cas was sitting at one of the tables, making love to a microwave burrito.

 

When Cas saw Dean approach, he raised his burrito to him in salute and said, “Epic food. I can’t get enough.” Cas took another bite and Dean felt about a million times worse for what he was about to do.

 

Unable to bring himself to look Cas in the eye, he stared down at the table. “Cas, uh, can we talk?”

 

“Of course.”

 

He finally got the balls to make eye contact, and Cas pulled the chair next to him out for Dean to sit. Dean couldn’t bring himself to take it.

 

And then, to add insult to injury, Cas said, “Dean, you know I always appreciate our talks, our time together.”

 

Way to pour salt into an open wound. Dean moved to sit on the table. He cleared his throat and finally said, “Listen, buddy. Um… You can’t stay.”

 

The look on Cas’s face was… it was like Dean had told a five-year-old kid that Santa wasn’t real, Superman was dead, and he lied about the puppy he bought him, all at the same time. Instantly, Dean knew what he needed to do. Craning his neck to see that his brother wasn’t anywhere within sight, Dean turned to Cas and grabbed the sleeve of his shirt.

 

“Come on. We’re getting the hell out of here.”

 

Cas's expression went from completely heartbroken to totally confused in under a second, before ultimately settling on a worried expression. "Dean, what’s wrong?" Although he had asked, he instantly followed Dean in the direction of the garage.

 

“Can’t talk here, get in,” he ordered, doing a double take around Baby to make sure Sam didn’t see them or follow them. When he sat down behind her wheel, he looked at Cas. “I’ve gotta tell you something, and I’m gonna need you to listen before you interject with your opinion, okay?”

 

Cas nodded quietly, giving Dean an expectant and simultaneously worried look.

 

As Dean pulled Baby out of the garage, he waited until they were at least a mile away from the bunker before he started talking. “So, uh… when you guys got the boot. The trials… they fucked Sammy up, Cas. Like, near death. An angel offered to help us. To help Sammy. But, I… Shit, Cas. This is gonna sound terrible, but I kinda tricked Sam into saying yes to being the angel’s vessel so he could heal him from the inside.”

 

Cas gave him a shocked, wide-eyed look, but just as promised, he didn't say anything. Instead, his look changed into a questioning one.

 

“I know what you're thinking, but when you told me Ezekiel was trustworthy, I made the call.” Dean turned down a sparse dirt road until they pulled up to an old abandoned quarry. He stopped Baby and turned to face Cas. “Sam has no idea that Zeke is still in him. And knowing you're hunted, the guy is totally freaked that he'll be next for helping us. Helping you. Sammy isn't well enough yet, so he threatened to leave if you didn't.”

 

Dean sighed and shook his head. “I know it's shitty, but I wanted you to know the whole story.”

 

Cas nodded slowly and looked down at his folded hands in his lap before he quietly asked, “May I talk again?”

 

“Ye yeah. Of course.”

 

For a long moment Cas didn’t say anything. It looked like he was contemplating everything until he finally nodded and said, “I understand. It’s Sam, you didn't have a choice. I won't do anything to jeopardize Sam’s healing.”

 

Cas opened the door of the Impala and got out of the car, walking away from it.

 

Without hesitation, Dean jumped out and darted after him. “Whoa, man! I wasn't just dropping you off in the middle of nowhere to get rid of you. I just wanted privacy to figure out what we should do.”

 

Cas tilted his head for a moment. “I saw the damage to Sam’s body. It will take months to heal Sam from the inside. It's best if I just leave and you call me when Ezekiel has left.”

 

Hearing those words come out of Cas’s mouth made him feel worse about the situation. Not better. Besides, abandoning his best friend when he needed him most was not sitting right with Dean. “Look. While he's got me by the balls when it comes to you being at the bunker, he doesn't have a say on what happens when he's not around.”

 

Dean clapped Cas’s shoulder and nodded. “You always wanted to be a hunter, right?”

 

Cas nodded slowly, his familiar confused expression taking over again. “Yes, but… Dean, I I'm human now. Any advantage I had as an angel to balance out my inexperience is gone.” He looked down again, his voice broken and quiet. “Now, I have nothing.”

 

“If I recall,” Dean started as he ducked his head to look Cas in the eye. “You held your own before when Eve made you limp. Besides…” Dean smirked. “How would you feel about a crash course on bein’ a hunter?”

 

“You really think I could be a hunter?” Cas asked skeptically.

 

Dean chuckled. “You never met Garth, did you?”

 

Cas shook his head before he looked around and sighed. “Dean, I don’t want to be a liability. If you just drop me off by the road, I can try to get to a bigger city. Lay low, maybe find some work.”

 

“Dude, you’re not a liability. We’re just gonna have to be creative.” Dean looked around before turning back to Cas with a comforting smile. “When I’m not workin’ cases with Sam, we could set you up somewhere and start your training. Come on, you tellin’ me you’re not even a little interested in getting trained by a Winchester?” Dean waggled his eyebrows.

 

Cas answered with a shy smile and Dean knew he had won. “Where would I go?” he asked after a moment before his expression changed into a worried one again. “It needs to be somewhere where I can acquire money and food.”

 

Dean looped his arm over Cas’s shoulder and smirked. “Get your ass back in the car and I’ll show you the wonderful world of squatting.”

 

…. :::: :::: ….

 

Corporate America. That's what Dean called it when, after twenty minutes, they found an abandoned warehouse only a half-hour drive away from the bunker. They carefully scouted the place out and Dean made a fist pump when they found a developed attic in one of the buildings. It was clear that no one had been in the building for ages. There was dust everywhere and the window in the roof slope was so dirty that nearly no light was coming through.

 

Cas swiped his fingers over it and the beam of light highlighted the dust on the dark wood floorboards. “And you think I can just stay here? No one will come?”

 

Dean shook his head. “This place hasn’t been touched in months. Maybe even years. And even if there’s a rent-a-pig that periodically checks on this place, I promise they don’t come all the way up here. It’s perfect.” Dean smiled as he looked around again. “We’re gonna need to get you some stuff, though.” He pulled out his cellphone clearly sending a text message before he pocketed it again.

 

“Like, something to sleep on… I won’t need more than that.” Cas still felt like a burden, no matter what Dean said. He wasn't used to needing help and it bothered him.

 

“You will absolutely need more than that.” Dean chuckled and used the sleeve of his shirt to wipe across the dust caked window, letting a little more sunlight filter into the attic. He hummed thoughtfully and said, “Figure if we use a couple credit cards, we can set you up with a mini fridge, a hot plate, a wifi hotspot, a laptop of your own, and a couple changes of clothes.”

 

He pursed his lips as he looked at Cas. “As far as showers, you can probably sneak into the bunker when we’re gone. I’ll grab you a phone too, so I can text you anytime Sammy and I take off.”

 

“Don’t you think that’s too risky?” Cas asked slowly.

 

“Well, only if you leave a friggin’ mess and rob us blind, making Sam question if someone entered the place. If you just slip in, use the shower and then leave, you’ll be good. Just… make sure you use my stuff. Don’t use Sam’s fancy shit. He can always tell when I use it.”

 

“Of course.” Cas nodded quietly. “Will you… visit me once we get all this stuff?”

 

Dean grinned broadly. “Who the fuck else is gonna train you?”

 

“But what will you tell Sam? Won’t he get suspicious if you leave?”

 

“Not if we play it right. Sometimes he goes out for a run. Sometimes I go out for a drink. Or a, uh… Well…” Dean smirked and waggled his eyebrows. “If I tell him I’m off to find a blue-eyed piece to occupy my time, he wouldn’t question it. And it’s technically not a lie.”

 

Cas squinted his eyes at Dean for a moment before he understood what Dean was implying. "You're implying that you’ll go out to find someone with blue eyes to have sex with, but in reality you’ll spend your time with me. How is that technically ‘not a lie’?"

 

Dean chuckled. “Because you have blue eyes and will be occupying my time. Sammy assuming the implication that I’m getting laid is why it isn’t technically a lie.” He dusted his hand off on his jeans and shrugged. “Besides, lying is part of being a hunter and one you should probably work on.”

 

Cas scratched the back of his neck with a deep sigh. “I see... So where do we start here?”

 

“First, I say we get all the supplies and whatever you need. Once you’re set up, I’ll shoot Sam a text and you and I will pick up some dinner and get to work on painting every anti-demon and anti-angel sigil wherever we can reach.”

 

Cas lifted his shirt to show Dean his tattoo. "I think I might need a second one. This only protects me from being detected by other angels. I need to add something against reapers and I need one against demon possession."

 

Dean nodded. “Okay. I know a guy. He’ll do it cheap. Hell, if you’re willin’ to suck his dick, he’d do it for free.”

 

He didn't have any money and he needed the tattoos. Cas bit his lower lip before he looked up at Dean. "I’ve never done that before."

 

That was met with a choked laugh. “Fuck, Cas. I was kidding. I mean, I know the guy actually would tattoo you for free if you sucked his dick, but…” Dean clapped his hand on Cas’s shoulder and shook his head. “I got you. You don’t have to whore yourself out.”

 

"Is that really a way someone can make money?" Cas asked after a moment. He needed to find a way to be independent from Dean's financial aid. If this didn’t work out, he would be on his own. He needed a fallback plan.

 

“While you technically fall into the absent father category, there are other ways to get money. I'll teach you how to hustle.”

 

“Alright.” That was probably a better way. Since he had close to no experience with sexual interaction, at least with Dean teaching him a new skill-set from scratch there wasn't much that could go wrong. He still decided to research sexual intercourse as soon as he had a laptop. Just to be sure. “What will you tell Sam about where you are today?”

 

“Told him I was checking on a possible lead. He and Kevin are busy with translating the tablet anyway. I’m sure he’s happy I’m out of his Fabio hair.” Dean grinned as he moved towards the door. “Alright. Ready?”

 

“Yes.” He gave Dean a timid smile before he added a quiet, "Thank you, Dean."

 

Dean nodded. “Don’t thank me. We could save ourselves a fuck ton of work if you could just stay where you belong.”

 

“But that isn’t an option and… you don’t have to do this for me, Dean.”

 

“You’re family, Cas. We take care of each other.” He half expected Dean to smirk, or laugh to solidify his teasing nature, but his friend’s expression was serious.

 

Cas gave Dean a long look, trying to accept that Dean really meant those words, although he couldn't possibly fathom why.

 

The truth was that Cas felt lost. He wasn't an angel anymore, he wasn't anything . He felt weak, vulnerable, subjected to a million things he didn’t need to worry about before. And the worst part of it was, he felt entirely useless.

 

But maybe that would change when Dean started teaching him to be a hunter. At least maybe then he could feel useful again. So he nodded and added, "I also need something to clean this place."

 

Dean smiled as he held the door open for Cas. “We’ll pick up cleaning supplies. I’ll see what I can do about the whole electricity thing, too. I bet we can rig something.”

 

“Rig?” Cas asked. There was still so much to learn. Maybe Dean could even teach him how to steal and drive a car.

 

“Yeah. Bet we could tap into a nearby power source and leech the electricity. It’s what Sammy and I would do when we’d have to squat.” Dean carefully looked around for signs of people, before ushering Cas out of the building. As they made their way back to the Impala, Dean took note of the empty parking lot. “Yeah. I’m betting we can get you set up. And at the very least, we’ll steal you a car and you can use it to charge stuff that needs charging.”

 

“Would you teach me how to drive?” Cas asked after a moment. “And how to steal and maintain a car?” He only knew the basics, but since he had never driven a car, he lacked the practical experience.

 

Dean looked contemplative for a moment before he fished out the keys to his car and tossed them to Cas. “Fine. But if you hurt Baby, I’m dropping you off to the nearest group of angels.”

 

Cas’s eyes widened as he promptly returned the car keys, pushing them into Dean’s hand. “No. Just no. I was talking about my own car, if we steal one.”

 

He laughed and placed them back in Cas’s palm. “Come on, you scaredy cat. Let’s get you used to being behind the wheel.”

 

“But… what if I make a mistake and I scratch your car?” Cas asked slowly. He didn’t want to die. Or worse, make Dean angry with him, possibly destroying their friendship.

 

“Then you have to be my slave for a week and do all the stuff I don’t wanna do.” Dean grinned and hip checked Cas. “Come on. It’s a big, empty parking lot. If you manage to scratch her here, then you are incapable of driving and will never be allowed to get behind a wheel.”

 

“No pressure then.” Cas chuckled nervously, remembering all of the times he had angered Fate in the past. He should have killed her when he had the chance.

 

Dean rolled his eyes and slid into the passenger seat of the Impala. That alone was a jarring sight. Cas had never once seen the man sit anywhere but the driver’s seat. It almost seemed wrong. Dean leaned over and started pointing to the dials on the dashboard. “That’s the speedometer, so you know how fast you’re going. This…” Dean touched the gearshift and continued, “Is how you shift her into gear. After you start her engine, pull this down until the marker is under the ‘D’ to drive. ‘R’ is reverse, ‘P’ is park, ‘N’ is neutral.”

 

Cas fumbled the key into the ignition with a nervous look towards Dean before he stepped onto the break and carefully started the engine. His hand went to the gearshift, for a moment touching Dean's fingers before he pulled his hand away.

 

Dean didn’t appear to notice, he just nodded and sat back. “Alright, give her a minute to warm her engine up first. When you kick it into drive, take your foot off the brake and gently press on the gas.”

 

Cas did exactly what Dean told him, trying to slow down his breathing and way too quick beating heart as he carefully started to drive through the empty parking lot.

 

“Good, you’re doin’ good, Cas. You can go a little faster.”

 

“Why?” Cas hoped Dean hadn't heard the insecurity in his voice. "I think I'm going fast enough."

 

Dean chuckled and leaned over slightly, pushing hard on Cas’s knee, accelerating to twice the speed they had been going.

 

“Dean!” Cas tried to pull away, in order to slow down. His heartbeat was bordering an unhealthy pace when he swerved in the parking lot.

 

“Shit!” Dean released his hold on Cas’s knee.

 

Cas immediately slowed the car down, breathing hard as he finally brought them to a stop before he shifted the gear into park. Cas shut off the engine and gave Dean an unamused look. “Can we do something else before my heart goes into cardiac arrest?”

 

Dean chuckled and nodded. “Yeah. That’s enough driving for today I think.” He sighed and looked at his watch. “I say tattoo first. Jerry closes shop at seven and I’d feel better knowing you got your ink before anything else.”

 

“Me, too,” Cas admitted. In his mind, he was already drawing out the symbols to upgrade the tattoo he already had, while he pondered the placement of the other tattoos. He got out of the car, noticing with surprise that his legs felt weak, so he braced his palms against door frame of the Impala to steady himself for a moment.

 

Being human was strange. There were a lot of physical reactions he still needed to get used to; like fear, or arousal. The latter happening more often than he wanted to admit to himself. It had been a lot easier to deal with it as an angel, when he still had complete control over his body. Now, his body seemed to crave everything that it had been denied over the years. It wasn’t a nice feeling. It felt like he was losing control to a hunger deep inside of him that he didn’t know how to fill.

 

“Aww, Cas, buddy, I’m sorry!” Dean was suddenly at his side. He was chuckling, but there was an airiness to the sound that implied sympathy, as opposed to mocking. Dean gently grasped his shoulders to steady him. “That was a dick move, man. I’m sorry. You gonna be okay?”

 

Cas gave him a reassuring smile. "Yes. I apologize. I guess I am a... 'scary cat'?" He wasn't sure if that was the expression Dean had used to describe him.

 

Dean laughed again, shaking his head in amusement. “You know, considering you’re a dude who’s literally thrown himself out of windows and shit, it’s kind of surprising. Not gonna lie, I kinda want to take you on a rollercoaster now.”

 

"It's easy not being scared if you know you can't get hurt." Cas bit his lower lip, wondering what else would scare him now that he was human. "I'm vulnerable. Everything feels different now."

 

At that Dean appeared to sober a little. “Shit. Sorry, Cas. I didn’t think of it like that. Come on. Let’s hit the road and you can…” He appeared to be struggling to say the next part, but he apparently found the strength. “As an apology for being all kinds of a dick today, you can pick the music.”

 

Cas gave Dean a reassuring smile. "You're not a dick. And I like your music, Dean."

 

“Bet you say that to all the hunters.” His teasing tone was accompanied by a salacious wink.

 

“I don’t like Sam’s music and I told him so. Repeatedly,” Cas answered truthfully.

 

Dean barked out a laugh as he slid into the driver’s seat. “Well, that seals that, then.”

 

Cas had no idea what Dean was saying, but he liked seeing him smile. For some reason, it made him smile, too. The first genuine smile, considering the day he had.

 

…. :::: :::: ….

 

They pulled up in front of a pretty unremarkable building in an economically depressed area of town. There were mismatched boards of plywood criss crossed haphazardly over the windows of the building they approached and graffiti on the walls. But to be fair, most of the buildings looked like that.

 

When Dean opened a rusty-looking steel door, he held it open for Cas to take as he opened a second door. Cas looked inside and was surprised at how clean the interior of the building was. Especially considering its exterior.

 

Dean barked out a sharp, “Yo! Jerry! Got a stat ink!”

 

There was a groaned expletive in a room partitioned off by stable doors. They slammed open to reveal a burly, older man with a darker complexion, broad shoulders, and a slight gut jutting out. Narrowed, dark brown eyes widened in surprise and his entire face lit up at seeing Dean. The smile on his face made him seem rather attractive.

 

“Son of a bitch. My favorite Winchester! What’s good?”

 

Dean chuckled and reached out to shake the man’s hand. Now standing closer to him, he was surprised at just how tall he was. “You know. Same shit, different day,” Dean answered.

 

Jerry laughed and nodded. “I hear that.” He looked down at Cas then, the expression on his face turned almost predatory as he licked over his bottom lip. “Who’s the pretty boy?” The question was directed at Dean, but Jerry never took his eyes off of Cas.

 

Cas turned around to look behind him, wondering who Jerry had meant before realization struck.

 

“Yeah, baby. I was talkin’ about you,” Jerry affirmed as his lips curled up in amusement.

 

Cas gave the man a shy smile before he answered, "My name is Castiel."

 

“Ain’t that pretty?”

 

Dean let out an annoyed sigh. “He needs ink. The usual. Can you cut us a deal?”

 

In that moment, Jerry appeared to become the representation of professionalism. “You know the deal. C-note for each piece.”

 

“Come on,” Dean urged, folding his arms over his chest. “Fifty a piece and I’ll buy you a couple of rounds next time.”

 

Jerry looked down at Dean with an unreadable expression for a moment. “Alright. It’s a deal, but, uh…” Jerry smirked and stepped a little closer to Cas. “Blue eyes, I can give you an even better deal with lips like yours.”

 

Cas tilted his head as he handed Jerry the piece of paper he had drawn the sigils on. “What do my lips have to do with it?”

 

Dean slammed his cash down on the counter next to the man. “Jerry. Shut up and give him a tattoo.”

 

“You didn’t even let him answer,” Jerry sneered. He took a step back, bracing his hands on the counter behind him as he raked his eyes over Cas’s body appreciatively. “Whaddya say, sweetheart? Wanna show me what that pretty mouth can do?”

 

"Are you suggesting that I suck your dick?" Cas asked slowly, the prospect was making him curious. Especially because Dean had to pay so much money for the tattoo and he felt bad about it.

 

Jerry tongued the side of his mouth and waggled his eyebrows. “If I was?”

 

Dean leaned forward and yanked Jerry forward by his t-shirt collar. It was surprising how almost comical it was, considering their size difference. “You need to shut the fuck up and do your job.”

 

"Dean!" Cas interjected forcefully. "He was asking me."

 

He turned to look at Cas, blinking a few times slowly, purposefully. Dean appeared to be waging a war within himself. “No,” he growled at Cas before letting go of Jerry with an annoyed glare.

 

“S’matter, Dean-y? You liked sucking my cock so much you’re gettin’ jealous?”

 

Dean rolled his eyes and flipped the man off. “Fuck off, Jerry.”

 

“I want to, Jerry,” Cas interjected. He was getting angry from the context of their conversation and it wasn’t fair that Dean was making decisions for him. Just because he was new at being human didn’t mean he couldn’t look after himself or make his own decisions.

 

Jerry’s eyes lit up, but before anything else could happen, Dean yanked Cas by the sleeve of his shirt, pulling him away from Jerry with a clipped, “Give us a minute.” When they reached the other end of the tattoo shop, Dean looked down at Cas with an extremely annoyed expression. “The fuck are you doing? I have the money to pay for your ink.”

 

"But I want to gain more experience with sex. You have sex with people all the time, why don't you want me to have my own experiences?"

 

“Dude!” Dean pulled Cas even closer to the door and whispered harshly, “Sex: yes! Not selling yourself. Don’t whore yourself out if you can help it. If you need to get laid so badly, I’ll take your ass to a bar and you can pick up a waitress like the rest of us.”

 

“I don’t understand the difference. Jerry and I both gain something from it. You don't need to pay and I get my experience. How is that a bad thing?"

 

Dean opened his mouth as though he was about to say something. He raised his finger and no sound came out. Instead his question was met with a mirthless chuckle and feigned smile of annoyance. The smile Dean usually had when he was trying to be patient with him, but was actually on the verge of yelling at him.

 

With a deep, steadying breath, bracing his hand over his mouth, Dean finally managed to calm down enough to respond, “I really don’t want to stand here, explaining the logistics and ethics of selling your body in exchange for goods or money. I’m gonna ask you, as your best friend, please. Please don’t suck Jerry’s dick in exchange for a tattoo.”

 

“Did you do it?” Cas asked after a moment.

 

Dean let out a huff and clicked his tongue. After a beat, he finally said, “That what you wanna hear? Fine. Yes. It was after Dad fucking sold his soul to save my ass. Sammy and me were broke, we didn’t have the kind of time to hustle the kind of cash you need for a tattoo, let alone two. So, yeah. I got Jerry to do us both for a blowjob. And I kind of hate myself for doing it. So, if that’s what you wanna do, go ahead. I can’t stop you.”

 

He scoffed and shook his head. “Fuck this. Do what you want, Cas.” Dean stormed out of the shop before he could even process what just happened.

 

Cas felt torn. He had wanted to do it, but he also didn’t want Dean to be angry with him. When he went back to the chair, he looked up at Jerry with a head shake. “I’ll pay with the money.”

 

“Could always suck my dick out of the kindness of your heart,” Jerry suggested as he placed a toothpick in his mouth and smirked.

 

“I don’t want Dean to be annoyed with me, so I have to decline.” Cas sighed deeply before he lifted his t-shirt and pulled it off, showing Jerry where he wanted the additional symbols. “I think I want the other one on my back, between my shoulder blades.”

 

Jerry grunted his understanding. “Standard anti-demon, angel, enchilada?”

 

“Enchilada?” Cas asked with a confused head tilt.

 

“Damn, you’re cute. No wonder Winchester’s hung up on you,” he said with a chuckle. “Alright, let me draw ‘em up, get a stencil. If you gotta piss, or need to do whatever outside, I’ll be about fifteen minutes. Then we’ll be set up and ready for ya’.”

 

Cas scrunched up his nose, not only because he didn't understand what Jerry meant by Dean being, “hung up,” on him, but also with the prospect of urinating. He still hated the fact that he had to. He nodded and quickly pulled his shirt on again before he went outside. He couldn’t see Dean when he went outside, so he rounded the shop to the back alley.

 

He quickly urinated behind one of the dumpsters and startled when he noticed Dean leaning against the wall a few feet away from him. He tucked himself in and went over to his friend, letting out a deep sigh. "I'm sorry, Dean. I didn’t want to make you angry.”

 

Dean shook his head. “Nah, man. It’s not my place to dictate where you stick your dick. Or in this case, where you take dick. You wanna sell yourself, that’s your deal.”

 

“I’m not. I’m paying for the tattoo with your money. But if I'm honest, I still feel bad about that."

 

Dean looked at him for a moment and exhaled a sigh of relief. “Thank fuck. And don’t worry about the cash. Once you learn to hustle, you can get me back, alright?”

 

"Okay." Cas took in a deep breath before chewing his lower lip for a moment. "You didn't want me to do it not because you were making decisions for me, but because you were worried?"

 

That appeared to take him aback. Dean’s brow furrowed in bemusement as he searched Cas’s face for his sincerity. “You thought I was tellin’ you what to do?”

 

"Yes. I was afraid, now that I'm human, you would think I can't make my own decisions or that... I needed protection." Cas gave him a pained look. "After the thing with April... I know why you would think that... But I don't want to stop myself from having new experiences just because my first weeks of being human have been less than ideal."

 

Dean laughed and looped his arm over Cas’s shoulder. “Now don’t get me wrong, I’m gonna worry about you. That’s what friends do. But if you’re gonna fuck someone, do it for the right reasons. ‘Cause you’re lonely, horny, or believe in love or something. Don’t do it for money. Or tattoos.”

 

"He offered that I can suck his dick out of the kindness of my heart, but I declined. Should I take him up on that offer?"

 

Dean’s expression turned serious in that moment and he shook his head. “No. ‘Cause then I’m gonna have to pop all the tires of his car and you’re not gonna want to be filled with that guilt, are you?”

 

Cas shook his head quickly before he gave Dean a thoughtful look. “I don’t understand your rules of how to get a sexual partner, but I accept your judgment about Jerry. Will you stay with me while I get my tattoo?”

 

“Why not? Curious to see if you’re a baby when you get poked.”

 

“I already got one tattoo and the pain was manageable,” Cas responded dryly.

 

Dean smirked. “Guess you don’t need me to hold your hand then.”

 

Cas squinted his eyes at Dean. “No.” He shook his head with a playful smile before he made his way back into the shop. Jerry told him to get ready once he was inside and Cas pulled his shirt off again, folding it over one of the chairs.

 

Jerry pulled out a bottle with a green liquid inside. Pouring it over a paper towel, he cleaned over the area under his ribcage next to the other tattoo he’d indicated earlier. It was cold and sort of tingled. Then Jerry pulled a piece of paper out and pressed it to the area. He pulled his chair out and pointed to the full length mirror in the corner. “Make sure the placement is where you want it.”

 

Cas got up and walked over to the mirror, looking down at his abdomen in the reflection to get a good look. “That’s exactly right.”

 

Jerry patted the chair. “Alright. Hop on. Let’s get to it.”

 

Cas sat down and leaned back against the comfortable chair, giving Dean a quick smile.

 

Dean chuckled and leaned against the counter. “Don’t be too gentle with him, Jerry.”

 

That was met with a sharp bark of laughter. “You sure got a funny way of flirtin’, Winchester.”

 

It was difficult to not smile at the way Jerry had the ability to silence Dean with his comments. Dean’s cheeks appeared to redden slightly and his response was a rather sad, “Shut up.”

 

Jerry chuckled and put a couple of sterile gloves on. He braced a hand against Cas’s torso to pull the skin taut. He held the needle over the area beneath his ribcage and looked up. “Ready?”

 

Cas nodded, biting his lip. He knew this wasn’t a very pleasant experience, but he had suffered hours upon hours of torture in his lifetime. This would be nothing in comparison.

 

He still hissed quietly when Jerry started, but it was just the initial sensation. Once the pain had reached a constant level, he managed to suppress it. He looked at Dean as a distraction, taking in his smile and the boyish way his green eyes were lit up by his amusement. Not for the first time, he caught himself thinking how attractive Dean was. It wasn’t something he wanted to think about. Dean was his best friend and they were family, but still… in the quietness of his mind, with the additional things he had to deal with as a human, like arousal, he noticed that his thoughts strayed to certain areas they shouldn’t go.

 

“Gonna get a little spicy,” Jerry warned as the needle drew closer and closer to the sensitive area under his ribcage.

 

Cas grimaced at the new painful sensation from the needle’s contact with his nerves. He needed a distraction. "Dean?"

 

“Changed your mind about the hand holdin’?” he asked with a chuckle as his voice drew closer.

 

"I just wanted you to tell me something distracting, but if you want to hold my hand, you can do that, too," Cas smugly retorted.

 

Dean grabbed the chair on the other side of Cas, pulling it up and making it a point to sit on his hands. “S’up, buttercup?” he asked, playfully batting his eyelashes in feigned innocence.

 

“I hope that isn't your new nickname for me. That’s even worse than ‘huggy bear’."

 

Jerry groaned. “Can you tone down the cutesy crap? I almost wouldn’t believe you offered to suck my cock half an hour ago.”

 

“Hey,” Dean warned.

 

The older man nodded in acquiescence. “Yeah, yeah. ‘Do your fucking job, Jerry’.”

 

When Jerry got closer to his ribcage again, Cas grimaced and his hand involuntarily slid over to Dean, grabbing his knee.

 

“If you ask me nicely,” Dean sing-songed, pulling out one of his hands and waving his fingers at Cas.

 

Cas chuckled lowly and was chastised by Jerry for the movement. He gave Dean a long look before he reached out to his hand with a smile. "Please. Would you hold my hand?"

 

Dean hummed thoughtfully, tapping his finger against his chin, before he smirked and grabbed Cas’s hand. “Only ‘cause you asked so nicely.”

 

Jerry groaned again. “You two are giving me diabetes.”

 

"I'm sure that's not how you get that illness, Jerry," Cas tried to reassure the man as he intertwined his fingers with Dean's and squeezed a little. He got a weird fluttery feeling in his stomach and chest when Dean rubbed his thumb over the side of his hand.

 

When the needle struck a nerve, he squeezed Dean’s hand so hard, there were little crescent shaped indentations from the way his nails had dug in. Still, Dean never released his hold on his hand.

 

“Gotta say, it’s not often I tattoo a guy holdin’ hands with his boyfriend,” Jerry muttered with an amused chuckle.

 

Dean rolled his eyes and ignored him. He leaned in to get a look. “How’s it comin’?”

 

Jerry continued working without ever looking up. “It’s comin’. Be patient. Art takes time.”

 

“It’s just a bunch of squiggly lines,” Dean pointed out, winking at Cas as he looked back at Jerry.

 

The older man withdrew the needle and looked up at Dean. “Keep insulting me. I’ll tattoo a dick on your boyfriend.”

 

“Maybe he’d like that,” Dean sneered in response.

 

“No, I wouldn't," Cas tried to intervene, “and I'm not Dean's boyfriend."

 

Jerry chuckled and quirked his brow. “Does that mean your pretty little lips wrapped around my dick is back on the table?”

 

Cas shook his head. "Dean told me I should only do it for the right reason." He looked at Dean with a frown. "If I met Jerry in a bar, would that be a right reason by your definition?"

 

Dean gave Cas an unamused look and turned back to Jerry. “Offer your dick one more time and I’ll cut it off.”

 

Jerry feigned a high pitched voice and mimicked Dean before returning his attention to Cas’s side. “Tell me what bar and when, and I’ll be there,” he whispered.

 

"What bars are around here?" Cas whispered back.

 

Dean let go of Cas’s hand with an annoyed huff and barked, “You done yet?”

 

“Yeah, yeah. This one’s almost done. Then the other.” Jerry was concentrating for another minute or so before he drew back and pulled off the gloves. “Wanna check it out and take a break before the next one?”

 

"I won't need a break, but I'd like to look," Cas answered, giving Dean an insecure look. He had annoyed him again and he wasn't sure why.

 

There was a sharp trilling noise that emanated from Dean’s cellphone and he looked down at the display. “Shit. It’s Sammy. I’m gonna take this outside.” Casting a look at Cas’s side as he passed by, he nodded to Cas and ducked out of the door as he answered the phone with a gruff, “Yeah?”

 

Jerry had moved over to his desk where he was bent over, writing on a piece of paper.

 

Cas sat up on the chair, giving Jerry a questioning look. “How do you want me to sit for the other one?”

 

Jerry smirked and nodded for Cas to stand up. When he did, Jerry immediately invaded Cas’s personal space. He slid the piece of paper he’d been writing on slowly into the front pocket of his jeans. “That’s where I’ll be later, if you’re serious. As for your position? I want you on your stomach,” he breathed into Cas’s ear as he trailed his other hand along the hem of his pants.

 

Cas could feel his own dick twitch at Jerry's words, a trail of goosebumps following the path where Jerry's hands touched Cas's bare skin. He licked over his suddenly dry lips and nodded before he laid down on his stomach.

 

Cas liked that Jerry was so direct. He was often confused by innuendo and references. But Jerry was very clear about what he wanted and that appealed to Cas. Made him curious.

 

Jerry chuckled. “Aren’t you obedient?” He leaned over Cas and licked a swipe up the shell of his ear before he said, “I like that.”

 

Cas gasped, his hips involuntarily rocked into the padding beneath him. He had no idea how Jerry was doing this to him. He felt embarrassed by his lack of self control, but at the same time excited because it felt so good.

 

“Well, now I’m really disappointed you turned me down,” Jerry grumbled playfully as he slid his finger down Cas’s spine. When his hand reached the hem of his jeans again, he tugged them down a little, revealing the top half of his ass. “Damn, sweetheart. You’ve got a great ass.”

 

Cas felt his face heating up. The way Jerry made him feel vulnerable and exposed somehow magnified his arousal. Jerry's hands felt strong, but gentle at the same time, and he seemed to know exactly where to touch Cas.

 

"Thank you," he whispered, bracing himself on his elbows when he looked back at Jerry. "Maybe I'll change my mind."

 

Jerry quirked his brow. “Dean’ll be mad.”

 

“Dean is not my boyfriend,” Cas repeated. “And he said it’s okay as long as I don’t sell my body for money or tattoos.”

 

He appeared to regard him for a moment before he smirked. “Then get your fine ass in the other room and show me what else you can do with that mouth besides talk.”

 

Cas looked in the direction of the door. "Dean might come back any minute. I would rather meet you later at the bar."

 

“I'm gonna want more than a blow job if you're gonna make me wait.” Jerry swiped the pad of his thumb over Cas’s bottom lip, a little roughly. “Mmm. These fucking lips.”

 

Cas looked up at Jerry, his mouth open and heart beating erratically, the same pace when Dean had startled him earlier. "What more do you want?" he whispered breathlessly, already feeling the accumulative wet spot clinging to his boxers.

 

“Sweetheart, I'll take whatever you're willing to give.”

 

Cas smiled shyly up at the other man, excited over the prospect. "Then I'll see you tonight."

 

“Don't tease me, baby,” he murmured, sliding his thumb between Cas’s lips.

 

Cas licked at his thumb that tasted very clean, which didn't come as a surprise seeing how immaculate Jerry kept his shop. He licked a second time before he wrapped his lips around Jerry’s thumb and sucked it into his mouth.

 

The groan that escaped Jerry’s lips was even deeper than his voice. “Oh, you’re gonna be fun.”

 

Cas let go of the man’s finger and smiled up at Jerry, still feeling shy, but happy about the fact that Jerry thought he was fun. He hoped his inexperience wouldn’t be too apparent. He didn’t want to go into this night unprepared.

 

“Alright, sexy. Get back in position. Winchester will assume you sucked me off if you’re not at least part way tattooed.”

 

Cas chuckled and turned around, biting his lip as he felt Jerry’s strong hands on his back. It hurt more than the other tattoo on his front, especially when the needle went over his vertebrae. But somehow all he could think about was the prospect of having sex and it made the pain much more manageable.

 

The door slammed open and he could hear Dean’s sigh of relief. “I was almost worried I’d find you guys fucking on the table.”

 

Jerry chuckled. “Not at my station. I keep this place sterile. You woulda found us on the floor.”

 

Dean rolled his eyes. “Whatever.” As he sat down in the same chair again, he gently touched Cas’s shoulder. “You doin’ okay?”

 

Cas hummed, pressing his forehead against his elbows to hide his face. "I'll survive," he pressed out.

 

Jerry surreptitiously trailed his free hand down Cas’s side, the one that Dean couldn’t see, his fingers teasing Cas’s skin with feather light touches as he got lower, and bolder. “He’s takin’ it like a man.”

 

Cas couldn't suppress a quiet moan when Jerry started to touch him, his breathing got shallow and he hoped Dean wouldn't notice the subtle rocking of his hips against the padding under him.

 

When he lifted his hips, Jerry managed to snake his hand under his stomach. A latex gloved hand then started trailing down past his navel.

 

Cas bit his lower lip hard so the moans wouldn’t escape. His whole body tingled with a desperate need. It became so intense, he probably would have let Jerry do anything to him. In fact, he needed Jerry to do anything to him.

 

“Cas, you sure you're okay?” Dean asked, his voice rife with concern.

 

Cas hummed and made an “okay” sign with the hand closest to Dean, hoping that would lift his friend's concern.

 

Jerry murmured, “He's just fine.” When Jerry’s hand cupped his erection over his jeans, Cas couldn't help but groan. He hoped Dean would think he was just in pain.

 

Dean stood up and drew closer. “Cas, do you need Jerry to stop?”

 

“Yeah, sweetheart? Want me to stop?” Jerry practically purred as he started rubbing Cas’s erection.

 

"No!" Cas nearly yelled before he cleared his throat. "I mean, no, uh… uh, um, please go on."

 

Jerry chuckled and started rubbing a little faster. Cas almost couldn't feel the pain of the needle anymore over the lust filled fog that was clouding his brain.

 

Dean cleared his throat. “I'm gonna take a leak.” He sounded a little weird, but Cas couldn't focus on that. He exhaled a sigh of relief at Dean’s quick departure.

 

As soon as Dean was out of the door, he moaned without holding back anymore.

 

Jerry stopped his gun and turned Cas’s hip up, his groin now facing Jerry. And the door. Jerry ripped off the glove and expertly opened Cas’s fly, slipping his hand through the opening in his boxers. A warm, surprisingly soft hand gripped his hard cock and he almost saw stars.

 

“Think I can make you come before he comes back?” He started pumping Cas a little faster.

 

Cas was already close, so he nodded, licking over his dry lips. "Yes. Oh, uh! Yes, please," he begged as he bucked his hips to fuck into Jerry's hand.

 

Jerry chuckled again, swiping his thumb over the head of Cas’s dick, rubbing the precome over his length before stroking at an even faster pace. “Damn, baby. You're the best kind of freak. You secretly hoping Dean walks in and sees you coming over my hand?”

 

Cas suddenly imagined Dean's green eyes on him, looking at his state of undress, flushed with arousal and need, and the fantasy pushed him right over the edge. Cas came with a gasp and a low groan, all over Jerry's hand and his own stomach. For a moment, he must have blacked out because the next thing he noticed was Jerry chuckling and wiping him down with a towel.

 

“Yeah, best kind of freak. I'm looking forward to tonight.” Jerry handed Cas a couple of baby wipes as he started re-cleaning his station.

 

Cas wiped away the last of the evidence of what they had done and smiled at Jerry. "Me, too."

 

If just a handjob could make him feel this way, what could more feel like? He intended to find out. But the fact that he had thought about Dean shortly before he came... he tried not to think about that.

 

“Ready to finish?” Jerry asked as he reapplied the gloves.

 

Cas grinned and nodded enthusiastically before he turned around. "Thank you, Jerry. That was... amazing."

 

“Wait ‘til tonight,” he promised as he braced his hand on Cas’s shoulder and turned on the gun. He leaned in close and whispered, “All I wanna do right now is feel how fucking tight you are.”

 

Cas's breathing hitched as he imagined Jerry fucking him. He knew the basics of anal sex, but he also knew his knowledge was limited. Maybe he could ask Dean about it.

 

In that moment, the door creaked open and thankfully he had the pain of the tattoo to distract him. “How much time is left? We've got shit to do, Jerry.”

 

“He'll be done in less than ten minutes. So calm your tits, Winchester.”

 

Cas distracted himself by counting to sixty, ten times in a row, before he opened his eyes and met Dean’s gaze. Dean looked away again almost immediately, but Cas didn’t have a chance to think about it because Jerry gently stroked down his spine before he shut off the gun.

 

“There you are, sweetheart. All inked and ready to go.” Jerry held his hand out to Cas to help him sit up.

 

Cas took his hand and let himself get pulled into Jerry’s personal space. He looked up at him, giving him a shy smile. “Thank you, Jerry.”

 

“Any time, sweetness.” Jerry smirked at him.

 

Dean cleared his throat in annoyance. He held the money out to Jerry. “Thanks, Jerry.”

 

“Feel free to bring him back anytime,” he said as he took the money.

 

Dean rolled his eyes and looked at Cas. “Ready?

 

“Yes, I’m ready, Dean.” Cas followed Dean outside, but not without giving Jerry another smile and a quick wave. He felt incredible. Content. The pain from his new tattoos more than manageable.

 

“Dean? You know a lot about sex, right?” Cas asked as soon as they were back in the Impala.

 

“I guess. Why?” he asked in response as he shifted the car into reverse and started backing out of the parking lot.

 

“Do you have any helpful tips for the first time with a man?” Cas asked as he tried to get comfortable without pressing his back against the seat.

 

The car came to an abrupt stop, so much so, if he hadn’t been wearing the seatbelt, he would have collided with the windshield. Dean looked at Cas in surprise. “Why would you think I’d know about having sex with guys?”

 

Cas gave him a surprised look before he shrugged. “I thought your general knowledge and experience could only be better than mine. I wasn’t assuming anything.”

 

Dean chuckled kind of nervously and rubbed the back of his neck. “I don’t think gay sex is the same as straight, Cas. I… You wanna fuck a guy?”

 

Cas shook his head and corrected, “I want to get fucked by a guy. Hopefully tonight.”

 

The look on Dean’s face was a combination of surprise and something else he couldn’t quite place. Hopefully, with more time spent as a human, he’d start to understand human emotions and facial expressions a little better. Dean swallowed dryly and put the car into drive as he answered, “Right. Uh… Wow. Okay.”

 

“You said I should do it for the right reasons. Like being horny and feeling lonely. There’s no money and tattoos involved,” Cas explained, so Dean wouldn’t get angry again.

 

“No, you’re right. I did say that. I just… I didn’t peg you for being gay,” he responded, keeping his eyes purposefully on the road. Which was actually quite unlike Dean. The man had a tendency to maintain full eye contact when they had conversations, even if he was driving.

 

Cas tilted his head and frowned at Dean. “Being gay would be if I'm only interested in a male sexual partner. But I don't care about the gender of people.”

 

Dean nodded. “Guess I can’t argue that. Well, if you’re gonna be fucking and fucked, the one thing I can tell you is, lube is your friend, and don’t fuck anyone without a raincoat.”

 

“I thought you need to be naked if you had sex. What good would a raincoat do?”

 

That was met with a bark of laughter. “We also gotta get you up on slang. A raincoat is protection. A condom?”

 

Cas rubbed his chin, suddenly feeling insecure. “Now the prospect of having sex seems a little daunting. I don’t know what a condom is… or what to do with lube. I didn’t know this was so complicated. Centuries ago people just had sex.”

 

“Well, lube isn’t really needed unless you’re doing anal. Which you want to do. A condom is like… It’s latex that goes over your dick. Before you stick your dick in an ass, or a vagina, you strap that bad boy on to prevent any STD’s… uh, sexually transmitted diseases. So, whoever you try to get to fuck you tonight, make him wear a condom, or don’t fuck him. And if it’s Jerry, maybe make him wear two.” Dean smirked at him with a challenging arch of his brow as he turned the vehicle left down a busy road.

 

“It's Jerry. He likes that I'm obedient.” Cas grinned, feeling proud of himself that he managed to get someone to like him.

 

“I bet,” Dean said with a chuckle. “Maybe next time, don’t let him jerk you off with your best friend a foot away from you guys, though…”

 

Cas rubbed the back of his neck, feeling heat rise to his face. “I apologize. I didn’t think you noticed. Not that I thought much in that moment.”

 

Dean gave him an unamused look. “I get it’s all new and exciting, but you gotta realize, things like sex in public are technically illegal, so be careful. And also, I know Jerry. I’m honestly surprised he was being that subtle.”

 

“He wasn’t subtle with me. I liked that he was very direct with his wishes. I didn't feel confused by him,” Cas explained before he looked back at Dean. “As soon as you were outside, he…” Cas squinted his eyes, not sure if there was a word that described what Jerry had done. But just the memory of it, when he had invaded his personal space and touched him so unapologetically, made his cock twitch again.

 

Cas pulled the piece of paper Jerry had given him out of his pocket. It had a name of a bar and an address on it. He sighed, realizing the mistake in his plan, meeting the man again. He had no car.

 

“He what?” Dean asked as he looked over his shoulder before merging into a different lane.

 

Cas looked up at Dean again with a confused head tilt before he remembered that he hadn’t finished his sentence. “Oh, I don’t know the word to describe what he did.”

 

Dean quirked his brow and looked at Cas in seriousness. “He didn’t do anything you didn’t want, right?”

 

Cas thought about that for a moment. “I didn’t know I wanted it until he had done it. Is that wrong?”

 

“Not technically. If you ever say no though, you stick to your guns, okay? Don’t let someone take advantage of you.” Dean pulled into a parking lot of a department store and when they got into a stall, he put the car in park and turned to look at Cas. “This is all kinda new and if you’re curious, or you have questions, you can come to me. I’ll help you to the best of my ability. Okay?”

 

“Thank you, Dean. You’ve been very helpful.” Cas chewed on his lower lip before he asked, “What if someone did something I wouldn’t have agreed to if this person had asked, but was too surprised and aroused to think about it?”

 

Dean braced his hand over Cas’s. “Okay, so don't let people touch you without asking first. That's not cool. Do I need to go back and castrate Jerry? ‘Cause I'll fucking do it.”

 

Cas gave Dean a long, insecure look. Jerry had touched him without asking and Dean said that kind of behavior wasn’t ‘cool’. On the other hand, he had been very aroused in that moment and wasn’t thinking at all. Now that his mind was clear again, he wasn’t sure about anything anymore. “I didn’t say no when he pulled down my pants,” he murmured more to himself.

 

Dean's eyebrows shot up. “I'm gonna fucking kill him.”

 

Cas gave Dean a shocked look. "Please don't! I'm still trying to figure this out. He touched me before he did that and I liked it. And when he pulled down my pants... I was surprised, but I liked how it made me feel... I... It's just now I'm confused if I should have liked it, because you said it wasn't 'cool'."

 

Dean sighed and sat back in his seat. He was silent for a moment, apparently trying to figure out what to say. “Okay. So… If you’re interested in someone sexually and you’ve both kind of acknowledged it, it’s okay if that person touches you. But, uh…” He looked out the window and pointed at a very unkempt man, greasy hair, and a surly scowl on his face. “If that guy came up to you and did what Jerry did, what would you have done?”

 

Cas squinted his eyes at the man Dean had pointed to before he realized that he couldn't see people's essence anymore. He sighed in frustration. "I would feel attacked."

 

“And that’s what it would be. An attack. If you touch someone who hasn’t given you the go ahead or you get touched by someone you haven’t expressed interest in, that’s not cool. But if for some fucking reason you’ve got a thing for Jerry… Then, mazel tov, I guess?”

 

"I don't have a thing for Jerry, Dean. I want to have sex and he is available without me having to go through all the confusing human things, like dating, innuendos, and references. My social skills aren't good enough for more. This is easier," Cas explained matter of factly.

 

Dean nodded. “I get it, man. Why do you think I only hook up with waitresses and bartenders? No strings, man. We don’t live the kind of life that includes romance, candlelit dinners, and vacations in Paris. But we’re human. We got itches to scratch. So, if you want to fuck random guys, do it. But please, be careful. If someone hurts you, I really don’t wanna have to deal with having to bury a human body.”

 

Cas nodded before he sighed deeply. "But I can't go to that bar tonight because I don't have a car yet. And maybe we should add... condoms and lube to the shopping list."

 

There was a beat of silence before Dean sighed. “Where are you meeting Jerry?”

 

Cas showed Dean the piece of paper with a questioning look. “Is that far away?”

 

Dean took the paper and looked down at it, before pulling out his cellphone. He was apparently plugging in the coordinates. He looked at Cas. “Do you really wanna fuck him?”

 

"Why not?"

 

“It’s just…” Dean shook his head. “Nope. Not my place to judge. But, uh… You’re gonna want to...” He let out a sigh. “Like I said. Guy’s kind of a slut. Make him wear two condoms, I’m not kidding.”

 

"Do you think he has condoms? Or is it customary that I bring them myself?"

 

“Yeah, bring some just in case. Don’t rely on other people to be responsible,” he murmured as he got out of the car. Dean looked at him as they started walking towards the entrance. “Oh, man. You’re giving up your anal v-card to Jerry. I wish I could tell Sam.” He chuckled good naturedly.

 

Cas stopped in his tracks and tilted his head. “You sound like you don’t approve. If Jerry had multiple sex partners as you implied, isn’t it a good thing that he has so much experience?”

 

“Cas, buddy… If you like the guy, it doesn’t matter what I think. And just so you know,” Dean said with a smirk before he chuckled. “As your best friend, I’m allowed to make fun of you for hooking up with people I’m not a fan of.”

 

"I don't know Jerry enough to tell you if I like him." Cas scratched his chin. "Can you at least tell me why you aren't a 'fan'?"

 

Dean sighed and shook his head. “He’s a nice enough guy. Kind of a horndog, and a huge skeeze. Trust me, I wasn’t the first person to suck him off for a tattoo. And I sure as hell wasn’t the last. But if it’s experience you’re looking for, he’s more than qualified. And if you have a thing for dick size, you won’t be disappointed.”

 

"I don't know if I have a thing for dick size. I'm starting to learn all kinds of new things about what I like." Cas gave Dean an excited smile. "I apparently like being given orders."

 

“Yeah, that doesn’t surprise me at all.” Dean chuckled as he grabbed a shopping cart and they stepped inside.

 

“Why is that?” Cas asked, curiously taking his surroundings in. He wondered what Dean wanted to buy first.

 

“Kinda ingrained into you, wasn’t it? To take orders.” Dean smiled at him, it wasn’t meant cruelly, it almost sounded like a compliment.

 

Cas nodded slowly when he started to understand. "It makes me feel good, to be obedient, getting orders, because it reminds me of my life before all of this. I guess it makes sense that it also gives me pleasure as a human."

 

He walked next to Dean, giving him a thoughtful look. "Jerry seemed to like that about me. Are there a lot of people out there who like an obedient sexual partner?"

 

“Depends. I prefer it to be a little more, uh… equal, I guess. Sometimes I’m in the mood to be taken care of, and sometimes I’m in the mood to be in charge.” Dean took them down the aisle with toiletries and stopped in front of a large display of a different variety of condoms. Dean grabbed a box labeled ‘magnum’ and at Cas’s quirked brow, he muttered, “Trust me. If you’re fucking Jerry, you’ll need this one.”

 

Cas took the box from him and it landed in the shopping cart before his eyes thoughtfully roamed over the display. "And which should I get if I want to have sex with someone other than Jerry?" Some of the condoms said "ribbed for her pleasure" and he held one of the boxes up for Dean to see. "Is that guaranteed only for women, or would a man get pleasure from this, too?"

 

Dean chuckled. “It’s bullshit. It doesn’t actually feel different. The only condoms that are special that you can feel a difference is the Fire and Ice ones. Like putting Tiger Balm on your dick. It’s weird, but not totally unpleasant. Yeah, you wanna go with standards.” He grabbed a box of Trojans and one marked Durex. “In my opinion, these two brands are the most reliable for not breaking. Just regular condoms should work with any person you hook up with.”

 

He reached over and grabbed a large purple tube marked Astroglide. “This is lube. Lube is your friend, Cas.”

 

Cas took the purple bottle from him and read the fine print on it. Slip into pleasure. Gel. Personal Lubricant. He looked up at Dean with a frown because that was a very vague description. "It doesn't say how to use it."

 

“I guess it would be a little weird to have instructions.” Dean looked around before popping the bottle open and pouring a small amount on Cas’s fingers. “So, it’s used to make it… smoother when you fuck or jerk off. If you want to, of course. Just, uh…” He grabbed Cas’s hand and extended his index finger. Dean circled his fist around the digit and started rubbing the lubrication over it. “You rub it on a dick, yours or someone else’s. And for penetrative sex, you use this in the, uh… hole you want to fuck, or get fucked I guess.”

 

Cas swallowed dryly when Dean was standing so close to him, rubbing the lube over his finger. Their eyes met and Cas couldn't look away until he felt the familiar heat rising to his face again. He licked over his suddenly too dry lips and nodded slowly. "I understand. Thank you."

 

“Yup, uh… Yeah.” Dean released his hold on Cas’s hand and then proceeded to explain everything he could as they went through the store. He grabbed things like new clothes, a cheap laptop, a wifi hotspot, some cleaning supplies, a hot plate, mini fridge, and various foods that didn’t require cooking.

 

Cas actually felt tired when they were done. “I didn’t know that shopping could be so exhausting,” he said after they had loaded everything into the trunk of the Impala.

 

Dean laughed. “Yeah. S’why I make Sammy do it as often as I can. I hate it.” When they got into the car, Dean reached over to the glove box and grabbed a cellphone. He handed it to Cas. “Used to be one of my old phones, but it’ll do you for what you need. Mine and Sammy’s numbers are already programmed into it.”

 

“Thank you, Dean.” Cas gave Dean a shy smile. “I’m saying that a lot today.”

 

“Hey. It’s the least I could do after kicking you out.” Dean looked down as he started the car. The slight frown on his face spoke louder than any words either of them possessed. Dean clearly felt bad. He felt guilty.

 

Cas laid his hand over Dean's and squeezed his hand. "Don't feel bad about this, Dean. You know how important Sam is to me. I would never do anything to endanger him. And it's only temporary. Once Ezekiel is gone, I can come back... Although, I still don't understand why he didn’t just talk to me. I would have understood if he didn't want me close after everything." Cas sighed deeply, feeling sad that so many good relationships he had in the past with other angels had been destroyed because of his mistakes. "I guess he's afraid of me, like all the other angels that I once called friends. It shouldn't surprise me."

 

Dean shook his head. “He didn’t seem scared of you. More like scared of the other pigeons.”

 

Cas scratched the back of his head with a thoughtful expression. “That doesn’t make any sense. Why would he be afraid of the other angels? Ezekiel is a well-respected and loved soldier. Did he tell you why he is afraid?”

 

“No. Just that he was pretty sure helping you and us basically put a target on his back.”

 

Cas nodded slowly. “He might be right in that assessment. I’m grateful that he’s still helping you, even though it’s dangerous for him. It’s good to know that there are still a few good angels out there,” he whispered the last few words as an overwhelming sadness bloomed within his heart. He missed being an angel. He leaned his head against the window and stared outside.

 

He wished he could have been the one helping Sam to heal.

 

Suddenly, he was shaken out of his reverie when Dean swerved the car and came to an abrupt stop. “Yes!” he cried out, darting out of the vehicle.

 

Cas frowned and got out of the car, wondering what Dean had seen that got him so excited.

 

He ran in between two buildings and came back with a relatively clean looking mattress. Dean grinned. “Somewhere to sleep!”

 

Cas grinned widely and helped Dean carry the mattress back to the car when he noticed it was much bigger than he had thought and wouldn’t fit into the Impala.

 

“How do we get it in the car?”

 

…. :::: :::: …..

 

The fact that they had managed to get all the crap they’d picked up into the attic without being spotted once was a goddamn miracle, but Dean wasn’t going to look a gift horse in the mouth. Cas had been cleaning the attic, while Dean was setting it up. Making it look like as much of a home as you could when you’re squatting.

 

Dean set the mattress on the floor under the window. Grabbing a couple of flat crates to use as a makeshift box spring, he placed the mattress on top of it. There were outlets, so using wires and a few other illegal tricks he’d learned from Frank, Dean was able to supply Cas’s little corner with enough electricity to keep his fridge running and to charge whatever he needed to charge.

 

When Cas was finished with dusting and getting rid of the cobwebs, Dean grabbed a couple of paintbrushes and spray paint cans before he looked over to Cas. “Ready to redecorate?”

 

Cas took one of the paintbrushes from him before he asked with a grin, "I'll paint the angelic sigils and you take the demonic ones?"

 

“Sounds fair,” he said with a chuckle. Dean grabbed the spray paint, while Cas grabbed the black can of paint. Dean walked over to the wall closest to the bed. “I’ll get this wall if you want to take that one?” He pointed at the wall with the window.

 

Dean looked at the cans of spray paint and chuckled to himself before he grabbed the black one and wrote in big, blocky letters (reminiscent of tagging), the word: Squatting. He grabbed the red can next and started spraying all of the different protective sigils he could think of. No point in just warding against angels and demons.

 

Cas started painting the sigils on his side of the room with a concentrated frown on his face. When he was finally finished, he stepped back and looked them over with a critical expression. He looked way too serious which made Dean’s fingers itch to chuck some paint in his face.

 

And apparently, the immature part of him won. Dean grabbed the other brush and dipped it into the spare can of paint before flicking it at Cas’s face. The surprised gasp and narrowed eyes glaring in his direction caused Dean to laugh outright. Dean gave him a cheesy grin before feigning an innocent tone and asked, “What?”

 

"You did that on purpose," Cas accused as he slowly walked up to Dean.

 

“I did,” he affirmed with a smirk.

 

Cas swiped his fingers through his paintbrush before he painted a streak of black paint over Dean’s cheek with his fingers, raising a challenging eyebrow at Dean.

 

“Alright,” Dean murmured. He tongued the side of his mouth and arched his brow in challenge. “That’s how it’s gonna be?”

 

Cas answered with painting a dot on Dean’s nose.

 

“Oh, you’re gonna regret that.” Dean was lightning fast as he dunked his brush in the can and proceeded to paint stripes up Cas’s neck. He quickly grabbed Cas by the forearm and wrestled him onto the mattress, straddling his hips, holding his arms down with his knees. Who said being bowlegged didn’t have its advantages?

 

Dean snickered and leaned forward before he started painting a big, black dick on the side of Cas’s face. Might as well get used to that if he’s gonna hook up with Jerry.

 

Cas struggled and laughed the whole time, trying to buck Dean off as he arched his hips upward. "Dean! That's..." Cas started to laugh again. "That tickles."

 

His struggling came to an immediate stop before Cas gave Dean a surprised look. "I'm ticklish."

 

There was no way in Hell to stop the outright maniacal laugh that escaped. “Oh, Cas. You really shouldn’t have told me that.” Dean grinned at the wide eyed and pleading look Cas gave him as he tossed the paintbrush on the ground. Dean tilted his head in feigned contemplation and hummed, “I wonder just how ticklish you are…”

 

Cas tried to struggle against his grip again. When it didn't work, he gave Dean a wide-eyed look again. "Probably not very ticklish. I'm sure there is no reason to test it."

 

“You sure?” Dean teased as he immediately started tickling Cas’s sides. The continued struggling in between bouts of laughter brought an evil grin to his face. “I don’t know, Cas. You seem pretty fucking ticklish.”

 

"Gnnn please, Dean," Cas breathed out in between choked laughter, "Please sto-o-o-p. I'll do anything!"

 

“Anything?” he asked, tone teasing and entirely suggestive as he continued his trail up Cas’s torso, pleased to note that the dude seemed to be ticklish everywhere.

 

“Yes, anything. Anything you want, Dean,” Cas breathed out in another futile attempt to get free as he rocked his hips against Dean again.

 

That was dangerous territory. Dean laughed and released his hold on Cas. He shifted and moved to sit on the bed next to him. “Alright. But when I collect, you can’t refuse.”

 

Cas nodded and sat up on the mattress, giving Dean a shy smile as he looked up at him through dark lashes. "What do you want?"

 

“I’ll tell ya’ when I think of it.” Dean chuckled. Cas looked ridiculous. His stupid sex hair was sticking up even more than usual, his cheeks were flushed from exertion and laughter, and there was a huge black dick on the side of his face. He was pretty damn cu

 

His thoughts came to a screeching halt. Dean shook his head and moved away from Cas. Like moving away from his friend would help him escape his stupid gay thoughts. Dean forced a smile. “Come on. Let’s get you cleaned up so you can go… do whatever with Jerry.”

 

“Suck his dick and get fucked,” Cas supplied helpfully, trying to rub the paint off of his cheek before he looked up at Dean. “I need your help. Not just with the paint. Can you give me advice on how to suck a dick?”

 

If he had been drinking something in that moment, he would have choked. It was like Cas lost his inhibitions along with his damn wings. Swearing, sex, and being so… open about it. Dean furrowed his brow. How the fuck do you teach someone how to suck a dick without a hands-on approach anyway?

 

Dean shook his head of his thoughts and looked at his friend. “Are you serious?”

 

“Yes. You said I could ask you anything.” He retracted his hand and looked at the paint on it with a frown. “I don’t like to go into a new situation unprepared. It leaves too much room for error.”

 

“Well, I mean… Sex is a kind of learning experience anyway. I can give you some tips, but you’re probably going to have to figure a lot of it out by trying it, you know?” Why the hell was it suddenly so fucking warm? Dean tugged at the collar of his shirt and cleared his throat. Maybe he had a fever?

 

Cas walked up right into his personal space before he handed Dean a wet towel with a raised eyebrow. "I suspect you drew a penis on my face, so I want you to remove it. And your tips would be highly appreciated."

 

Dean feigned innocence. “I have no idea how that big black dick got on your face. Maybe Jerry did it. You know, earlier, when you were distracted.” Yeah, it was official. Making fun of his best friend was one of his favorite things.

 

Cas squinted his eyes at him. “No, that was you. Jerry would have given me the real thing.”

 

“Damn, Cas.” Dean laughed. He liked this side of his best friend. He took the towel from him. “Alright, gimme your face and I'll make sure you're pretty for your man.” He grasped Cas’s chin and started wiping the paint off.

 

"You wanted to give me tips," Cas reminded Dean again with a playful glint in his way too blue eyes.

 

“Right.” Dean kept his concentration on cleaning Cas’s face. If he made eye contact, he wasn't going to be able to say what he was about to say. “So, uh… More than anything, listen to and watch how he reacts. You'll be able to tell if he's enjoying himself. Um, have you ever eaten a popsicle?”

 

“No. Why is that relevant?”

 

“Well, it’ll give you an idea.” Damnit. Dean rolled his eyes at himself and realized he needed to be less of a little bitch about things. After Cas’s face was clean, Dean took a step back and said, “Gimme your hand.”

 

Cas reached over with his right hand, giving Dean an expectant, but confused look.

 

Taking a deep breath, Dean extended Cas’s index finger. “What I’m about to do: first, take note of what to do when it’s a dick in your mouth, and second… If you ever tell anyone about this, I’ll make you spend a day with Crowley.”

 

Cas scrunched up his nose and nodded, sounding a bit breathless as his eyes were glued to Dean's mouth. "I won't tell anyone.”

 

Now or never, Winchester. Dean closed his eyes and wrapped his lips around Cas’s finger. He started circling his tongue around the digit as he gently sucked. He was pretty sure the heat in his cheeks made his face bright red. Hopefully the shitty lighting hid that. When Dean pulled off, he tapped his tongue on the tip of Cas’s finger and finally withdrew. “Uh… Like that. Something like that oughta get you there.”

 

Cas pulled Dean's hand closer to his face and extended Dean's index finger. Before he could say anything, Cas had already wrapped his lips around his finger, perfectly replicating what Dean had just done. When he tapped his tongue on the tip of Dean's finger, he tilted his head. "Like that?"

 

When did I die and end up in porn heaven? Dean shook his head in a daze. “Uh… Yeah.” Cas was a quick study and Dean wasn’t entirely ready for an existential crisis, so he took a step back from Cas and forced his thoughts to go any other direction than south.

 

To his bad luck, Cas had another question. “Should I swallow?”

 

Dean’s eyebrows shot up. “Uh… Yes, if you want? It’s not… It’s not a great taste.”

 

Cas gave him a long look before he squinted his eyes at Dean, stating, “I’m making you uncomfortable.”

 

Great. Now he felt like a dick again. Dean sighed. “Look, if you have questions, I told you I’d help you. And I mean it. But yeah, the fact that I’m giving you sex tips for when you hook up with Jerry is weirding me out a little.”

 

“Because it’s Jerry, or because it’s me?” Cas asked with an unreadable expression. Even though he was human now, and his facial expressions had a bigger range, he still had the poker face down.

 

“Definitely Jerry. Your sluttiness seems almost cute. His is creepy.” Dean’s lips halfway tilted in a crooked smile of reassurance.

 

Cas stepped closer, staring intently into Dean’s eyes. "As my friend, would you rather see someone else be my first?" There was something about the way he asked that question. An underlying implication that Dean wasn’t entirely sure he was ready for.

 

And yet, the selfish, possessive part of Dean wanted to scream, ‘yes!’, but the realistic and terrified part won out. He shook his head. “I just want you to be safe. That's all I care about.” That wasn't technically a lie.

 

Cas stepped closer, his gaze still intense. "Do you think I will be safe with Jerry?"

 

Again, the selfish part of him was daring him to take over. Instead, Dean looked at Cas and asked, “Does he make you feel unsafe or unsure?”

 

"No." Cas shook his head. "But you know him better than I do."

 

“Well, I can guarantee he's not a reaper working for the angels,” he offered with a smirk.

 

For a fleeting moment, it looked like Cas was disappointed with his answer before he suddenly turned away from Dean with a light shrug. “Alright.”

 

He went over to the mattress and pulled off his t-shirt, before he looked through his new clothing with a concentrated frown. After a moment, he pulled out a dark blue shirt and shrugged into it, buttoning it up to the top.

 

Dean crossed over to him and shook his head. “No, dude. You look like a waiter.” He started unbuttoning the first two top buttons. “You wanna play the part, you gotta look it.”

 

Cas looked up at him with a soft smile. “You think I look good enough?” he asked before he ripped open the box of magnum condoms and put two of them in the back pocket of his jeans.

 

Dean looked Cas over appraisingly. He actually looked really good. Too good for a tool like Jerry, but he was trying really hard to be a supportive and understanding friend. Granted, if Cas was living with them and there wasn’t the added guilt that he kicked him out, Dean knew he’d be far less accepting of it. It was kind of amazing how guilt makes you into a less judgemental dick.

 

“You’ll be the prettiest princess at the ball,” he teased.

 

Cas gave him a quick, lopsided grin before he frowned. “Is the bar far away from here? Could I walk back if I needed to?"

 

“No, man. It’s way too far to walk.” Dean sighed and looked at Cas. “Do you want a ride? I know Jerry can drop you back here after.”

 

Cas nodded thoughtfully. "Thank you, Dean. Maybe I can get him to drop me nearby. I don't want anyone to know where I live."

 

“Good idea. And if you run into trouble, or you need me to come get you, just call. I’ll come right back,” he assured. While he honestly wasn’t worried about Jerry Dean had known the guy for years it was the fact that he was dropping Cas off at (probably) some skeezy gay bar that wasn’t sitting right with him for some reason.

 

“Thank you. If you don’t have any time tomorrow, I will research a way to acquire my own car.”

 

Dean nodded. “I’ll let you know. Depends on whether or not we get a case.”

 

Cas went over to his bed again and searched his hoodie for something that Dean couldn't see at first. Turned out to be his wallet and angel blade. He put his wallet in his other back pocket before he grabbed the black leather jacket that Dean had chosen as part of Cas's new look. Cas was clearly trying to find a way to place his blade on the inside of his jacket. After a few failed attempts, he sighed in frustration and threw the blade onto the mattress.

 

“I need to upgrade this jacket,” he murmured, looking annoyed.

 

“It’s cooler than your trench coat, though.” Dean really liked the look, if he was honest. Cas in a leather jacket seemed kind of right. “Here,” he said as he held his hand out for Cas to give him the blade. Dean reached into the internal pocket of Cas’s jacket, ignoring the bemused smile his friend was giving him, considering he was still wearing said jacket, and found the seam of the pocket.

 

With a quick jerk, Dean ripped the seam slightly and slid the blade into the pocket, angling it to go through the hole in the seam, now resting along the internal hem of the jacket. Dean felt pretty impressed with himself for ripping a right sized hole to prevent the hilt from slipping through.

 

“There,” he said with a smile as he took a step back. “Now you’re good.”

 

“Now I’ve got protection,” Cas grinned, elbowing his side.

 

Dean chuckled and arched his brow. “Just make sure you don’t mix ‘em up.”

 

Cas winked at Dean with a smirk. “I won’t. I had a good teacher.”

 

…. :::: :::: ….

 

Jerry wasn’t there when they arrived at the bar, which wasn’t surprising because he had told Cas that he would be there at a later hour. So Cas used the time to get a feel for the bar and the people, trying to soak in as much knowledge about social interaction as possible, trying to learn to blend in.

 

To his surprise Dean had come into the bar with him, although he hadn’t been very forthcoming with a reason. He had mumbled something about waiting until Jerry was there and Cas had accepted that explanation, though he felt there was more to it. He wondered if Dean still felt the need to look after him, as if Cas was a baby in a trench coat… well, leather jacket now. It also reminded him that he should start to train in hand to hand combat since he hadn’t even been able to shake off Dean when he had tickled him.

 

It bothered him. At least he still had his angel blade.

 

Dean had pulled him over to the bar and bought them both a beer, before he sneaked him a few dollar bills for his wallet, because apparently, it was always important to have some cash on him.

 

The beer didn’t taste bad and after half of it, Cas felt relaxed and started smiling. He tried to remember that his alcohol tolerance as a human… sucked.

 

He chuckled when he used that word in his mind. He liked Dean’s vocabulary. He wanted to mimic it more often to blend in. Dean gave him a confused look, probably because he had started to laugh without any obvious reason.

 

He felt nervous about his meeting with Jerry. Very nervous and he hoped Dean wouldn’t notice.

 

“Penny for your thoughts,” Dean said as he rested his elbow on the bar and took a long swig from his bottle.

 

“I have a lot of thoughts,” Cas replied vaguely. It wasn’t technically a lie. Also something he had learned from Dean.

 

Dean rolled his eyes. “You know, every thought you share takes a penny off on what I paid for today. You’ll have less debt.” He winked at him before taking another swig.

 

Cas bit his lower lip before he looked up at Dean. "I'm nervous."

 

So much for not letting Dean know. But he still felt guilty about the amount of money Dean had spent on him today.

 

“Why?” he asked, regarding him seriously.

 

“Because I feel like there is so much I still don’t know,” Cas answered honestly.

 

Dean smiled and shrugged. “Only one way to learn, right?”

 

Before he could answer, a younger man easily ten years Dean’s junior slid in front of Dean, leaning against the bar as he looked Cas over. Cas had to refrain from laughing at the indignant eyebrow raise Dean gave the back of the man’s head as he backed up.

 

“You here with anyone?” the man asked. He was rather handsome, fair complexion, dirty blond hair, and a pleasing smile. He had a lithe and smaller frame, and spoke with a rather pleasant sounding southern drawl.

 

“Yes,” Cas answered with a shy smile. “You’re standing in front of him.”

 

When the young man turned to look back at Dean, the hunter sneered at the kid and barked, “Beat it, bitch.”

 

The young guy let out an annoyed huff and stormed away from them. Dean moved his stool back to where it had been and shook his head in apparent amazement. He looked down at himself and pulled his jacket open as he asked, “Like, you can see me, right? I’m not blending in with the background or something?”

 

Cas chuckled and gave him a thoughtful look. “Maybe they all somehow know you only like women as a sexual partner.”

 

As Dean was about to retort, an older Hispanic man sidled up next to Cas on his other side and whispered in a thick accent if he could buy Cas a drink.

 

Cas felt flattered with the attention he was getting. Finding a male sexual partner seemed to be a lot easier than finding a woman. He turned to the man behind him with a smile, thanking him before he explained that he was already sharing a drink with someone.

 

Dean leaned across Cas and barked, “You see me with him, right? We’re clearly having a conversation. Fuck off.”

 

The Hispanic guy flipped him off before he stated, “You’re just sitting next to him. No one in his right mind would sit there for over ten minutes and not kiss those fucking sinful lips."

 

“It’s called romance, you asshole. Maybe I wanted to get to know him,” Dean countered with a challenging quirk of his brow.

 

The guy tsked and shook his head. "You’re totally not into him."

 

In that moment, the man from earlier walked past them, obviously having overheard their conversation. He nodded at the Hispanic guy. "Right? I totally got the best friend vibe from him, like he’s just the wingman or whatever."

 

The Hispanic guy gave Dean a smug grin. “You’re clearly not his date.”

 

Cas followed the conversation with curiosity up until the point the Hispanic man had stated that Dean wasn’t interested in Cas. He had no idea why that comment had left a painful sting in his heart. It was probably the reason for his next words, “He actually is my date and I’m only interested in him. So if you both would excuse us.”

 

Dean poked his tongue out at them before they left, because apparently his best friend had the maturity level of a six-year-old, and then smiled at Cas smugly. “Attaboy, Cas. Now that’s how you say no.”

 

Cas rubbed the back of his neck in embarrassment, knowing that he would have said yes to that first guy in a heartbeat if Dean hadn't been there. “That only worked because you were here.”

 

“See? I’m good for something.” Dean clinked his beer against Cas’s and finished it before wiping the errant drop he spilled with the back of his hand. It was almost distracting.

 

“You’re good for a lot of things,” Cas murmured before he took another swig of his beer, licking absentmindedly on the rim of the bottle for the last drop.

 

“Dude,” Dean groaned. “You tryin’ to get every guy in here to buy you a drink?”

 

Cas tilted his head in confusion. “Why? Did I do something wrong?”

 

He chuckled and shook his head. “Nevermind.” Dean nodded at his now empty bottle. “You want another?”

 

Cas looked at his now empty bottle thinking that it was the reason people wanted to buy him drinks. He still had so much to learn. He would drink the next one slower. "Yes, thank you." He smiled at Dean before he frowned when his gaze fell on the clock on the wall. Jerry would be here soon. "Are you sure you want to wait here until Jerry arrives? You already did so much for me today."

 

He felt guilty for stealing so much of Dean's time.

 

Dean smiled. “Think of it as a favor to me. If he doesn’t show, then you aren’t being stranded.”

 

Cas bit his lower lip, wondering if he was hoping for Jerry to show or not. He was still nervous, but he was also horny. He wanted to have sex. But a big part of him had wanted Dean to talk him out of it before they left. His musings were interrupted when Dean put a second bottle next to him on the counter. He startled slightly, looking at the clock again, only to see that just three minutes had passed.

 

“Have you ever been nervous before sex, Dean?” Cas asked finally.

 

“Course. Anytime you try something new, man. Nerves are normal,” he assured as he sat back down. “The more you do it, the less nervous you get.”

 

A treacherous thought reminded him of the fact that this wasn't the first time he had wished he could have a new experience with Dean instead of someone else. Not just because Dean was the most important person in his life, but also because he felt… safe with him.

 

But even he knew he couldn’t just ask Dean to have sex with him. And not just because Dean was exclusively interested in women.

 

He took a swig of his new beer, hoping the alcohol would help with his nervousness. Unfortunately, the only thing it had done for him so far was cause the need to urinate.

 

“Excuse me,” he murmured before he left Dean at the bar to go to the bathroom.

 

The bathroom was empty and he went to one of the urinals to get it over with, feeling slightly better when he was done. He washed his hands and looked at himself in the mirror, rifling his hand through his hair when he noticed it was a mess. He tried to get it straightened out, but his fumbling was only worsening it.

 

"Need some help, handsome?" an unknown voice suddenly asked from behind him.

 

Cas looked up and noticed a very attractive man in the reflection of the mirror. He reminded him a lot of Inias. Dark hair and piercing blue eyes, a gentle smile playing around his lips. In that moment, he found he missed Inias very much. And that thought made him feel even more lonely. He returned the stranger’s smile, trying to remind himself that the man wasn’t Inias. Just someone who shared a lot of similarities with his vessel. “My hair seems to have a mind of its own.”

 

The man laughed. It was a deep and pleasant sound. He slid to stand next to Cas, still looking at him through the mirror. “So, this look wasn’t earned, huh?”

 

Cas didn't understand what the man was talking about, forcing him to curse his inexperience once again. "I think I have to blame the wind outside."

 

“Don’t know if that’s a good thing or a bad thing,” he said with a sly smile.

 

Cas was sixty-seven percent sure the man was flirting with him, so he took a leap of faith and attempted to flirt back, hoping it would work. He gave the man a shy smile and rifled his fingers through his hair again, giving him a questioning look. "What do you think?"

 

The man’s smile turned into an outright smirk as he swiftly grabbed Cas by the hips and flipped him around, now crowding him against the counter. “I think I wanna try that.”

 

Cas's breathing hitched as he tried to understand what was happening. The man was using too many innuendos for Cas to get a clear idea of what he wanted. Maybe he just wanted to help him with his hair. He frowned before he tilted his head. “What do you want to try?”

 

That was met with a chuckle as he raked his hand through Cas’s hair before tugging it slightly, bringing his face closer. The man tilted his head slightly, purposefully licking his lips as he blatantly stared at Cas’s. “You a kisser?”

 

"Yes?" Cas answered, sounding as insecure as he felt, wondering if the man wanted to kiss him. He didn't even know his name.

 

“Good,” he murmured as he closed the gap between them. His lips were slightly chapped and it was weird when he thought about the fact that they were basically battling each other’s face. His thoughts returned to the time he kissed Meg, like the stranger was kissing Cas. He’d enjoyed the sensation very much, but it was just as bizarre to him as an angel as it was to him now as a human.

 

The man groaned and stuck his tongue in Cas’s mouth. He bit back the gasp of surprise and went with it, assuming that it was what he was supposed to do. Cas mimicked what he’d done to Dean’s fingers earlier and was rewarded with another pleased moan. The guy started frantically undoing Cas’s pants, never breaking contact.

 

Cas wasn't sure what to do. This was all going so fast, but he could already feel his erection straining against his jeans. The man was very handsome and he felt attracted to him because he looked like Inias, but...

 

He stopped kissing the man and pulled back. “What’s your name?”

 

“Whatever you want it to be,” he murmured as he gripped Cas’s hips and guided him into the stall behind them. He latched the lock and pressed in again, resuming his unbuckling of Cas’s pants.

 

Cas was hard now. He loved being manhandled, recognizing this as one of his weaknesses. He reached over to help... Not-Inias with his jeans, opening them up and pulling them down. "What do you want?" he asked, feeling breathless from the kisses and the way Not-Inias was pressing him against the wall.

 

“You prepped?” he asked, voice husky and deep.

 

He didn't know what that meant and for the second time that day, Cas wondered why he thought it had been a good idea to go into a situation without the proper research. "I... um... I don't know what that means."

 

Not-Inias smirked. “That means no.” He leaned in and licked along the seam of Cas’s lips. “Good.” Without hesitation, he flipped Cas around, his hands now bracing the wall. Not-Inias gripped Cas’s pants and pulled them and his underwear down to his calves.

 

He dropped to his knees and spread Cas’s cheeks apart. “Fuck. You look unused.”

 

Cas had no idea why Not-Inias's words aroused him so much. What he was doing with him felt incredible and made his knees weak. "I'm new to this," he admitted breathlessly.

 

“Seriously?” he asked, leaning around his side to look up at Cas.

 

Cas nodded, feeling his face heating up. "Is that... a problem?"

 

Not-Inias shook his head and groaned outright. “Fuck no it isn’t. That’s fucking hot.” He returned his attention to Cas’s ass. Strong, deft fingers kneaded his cheeks as they were spread. Not-Inias leaned in close enough, Cas could feel the man’s heated breath against his hole.

 

When the man’s tongue suddenly started licking his rim, Cas groaned outright at the sensation. Not-Inias proceeded to lick and slurp at his hole until his tongue snaked its way inside.

 

Cas gasped and moaned loudly, pressing his forehead against the wall. He had no idea sex could feel this mind-blowing. "Uh, yes... um, oh... fuck," Cas gasped out uncontrollably.

 

Not-Inias started circling his tongue as his lips cupped Cas’s entrance. As the pleasure shivered through him, Not-Inias suddenly pulled away and Cas had to refrain from outright whimpering at the loss of contact. He could hear a little fumbling and a cap being popped open before a slick, wet finger replaced the man’s lips.

 

The way he teased his hole, Cas realized why humans could get addicted to sex. Not-Inias slipped his finger inside and the combined pressure and slight burn was both a little strange and immensely satisfying. He wanted more.

 

His instincts were thankfully starting to take over as he rocked his hips back, against the man's finger to get him to push it deeper. He didn't expect the overwhelming jolt of pleasure to course through his body as the man crooked his finger inside of him. "Fuck," he gasped out. "Oh, uh, please do that again."

 

Not-Inias chuckled and purposely tapped that spot again, almost whiting out his vision. It felt so incredible, he almost didn’t realize when the man had gotten another finger inside of him. Now there were two fingers tapping that spot in between a burning, widening stretch when he scissored his fingers.

 

It hurt a little, but it was nothing in comparison to the immense pleasure he was feeling. Like he was melting under Not-Inias’s capable hands. He felt like he was losing his mind, his only anchor being the way he braced himself against the wall. Cas was unable to stop moaning, thinking that he would do anything for this man should he ask for it. “Please,” he breathed out brokenly, though he didn’t know what he was begging for.

 

“I’ll give you what you need, don’t you worry,” Not-Inias said as he carefully slipped a third finger inside of Cas. He started pumping his fingers in and out, the man’s breathing coming out in ragged pants, hitting his dampened skin and causing a shiver to course through Cas.

 

He had no idea how much longer he could take it. He had never felt anything even remotely similar, and even that one time having sex with the reaper paled against what this man was doing to him. He was incredibly thankful that Not-Inias seemed to know what Cas needed and that he was more than happy to give it to Cas.

 

When his fingers pulled out entirely, Cas almost growled at the loss. Not-Inias chuckled and stood up. Cas could hear the man’s pants being unbuckled and dropped as well as the sound of foil being ripped open. He craned his neck to look back and was almost mesmerized as he watched Not-Inias slip a condom onto his dick before coating himself in lube.

 

Not-Inias drew closer and guided the head of his hard cock to Cas’s entrance. “You want it?”

 

Cas looked back at the attractive man and smiled. He was happy his first time happened with someone so capable. "Yes," he breathed out. "Please."

 

Without hesitation, he carefully pushed in. Cas let out a sigh when the head of the man’s cock breached him and sunk inside. It was much bigger than the man’s fingers, intensifying the burn. Not-Inias let out an appreciative groan as he slowly pushed in, deeper and deeper. “Fuck… I forgot how good a virgin ass was.”

 

Cas felt so filled and stretched. It hurt more now, but Not-Inias's praise about his ass made him groan. He wanted to give him as much pleasure as he had given to Cas.

 

Not-Inias continued to slowly sink in when the man’s right hand wrapped around Cas’s erection. He started pumping his cock as he began whispering filthy things in his ear. “You’re so fucking tight. A cunt could never beat your fucking ass.”

 

Cas choked back a relieved sob when Not-Inias started to stroke his erection. The man was completely inside of him and when he slowly pulled back, his dick rubbed directly over that magical spot. He leaned back against Not-Inias, desperate to hear his voice whisper more filthy things into his ear.

 

“You like that, baby? You like your tight hole being stretched on my dick?” Not-Inias pulled out halfway before slamming in and striking the spot again, his hand never once faltering as it continued to pump Cas’s erection.

 

"Yes! You feel so, uh! Uh, good," Cas panted, rocking his hips back. It stopped hurting now and he just felt stretched, and filled, and oh, so good. He squeezed his eyes shut, taking the assault of pleasure when Not-Inias started to fuck him hard, fast, and deep.

 

Heat was pooling in his groin, his balls started to tighten and he knew he was close. He couldn't stop moaning. "Uh, Uh, I… I'm so close."

 

Not-Inias panted out between groans, “I bet you are. I love virgin whores. The kind of whore who gives up his ass for the first time to a stranger in a bar bathroom.” His pace never relented through the litany of insulting compliments.

 

Cas had no idea why that last comment brought him so close to the brink. He gasped and moaned, desperately trying to stop himself from coming.

 

“Mmmm,” Not-Inias moaned as he chuckled. “Somebody liked that. I could feel you clench. You’re gonna be a needy little whore.” He started thrusting faster. “Can’t wait to have this ass again… mmm… after you’ve ridden every guy in town ‘cause you fucking need it, don’t you?” Not-Inias started pumping Cas’s dick in time with his thrusts. “Tell me how much you need it.”

 

Cas panted loudly from the way he felt on the edge again. An edge Not-Inias seemed to pull him away from with a soft shift of his hips and staggering of his thrusts. Cas thought he was losing his mind with the lust and need he was feeling. In that moment he wanted everything Not-Inias had said. He wanted to have all the cocks he could get, and he wanted Not-Inias to fuck him again after. He moaned, his breathing came out in short gasps when he whimpered. "I need to get filled. Please. I need your cock."

 

“Fuck…” he groaned out as he started fucking into him even harder. The sound of skin slapping against skin was unmistakable.

 

When he heard the door of the bathroom open, he gasped and braced his hand over his mouth to stifle himself.

 

Not-Inias let go of Cas’s cock to grab his hand and yank it away. “Don’t censor yourself. Let ‘em hear how badly you need to get filled.” He began thrusting into Cas, pace unbidden and rough as he fisted Cas’s cock again. “Come on, baby.”

 

Cas couldn't have stopped himself even if he wanted to. The pleasure was just too much. He moaned loudly, losing himself completely in the way Not-Inias made him feel. "Yes, please, please, uh," he moaned, "please, I need your cock."

 

That was met with a chuckle before Not-Inias started practically pounding into Cas. His breathing was heavy and Cas knew there would be bruising from how tight Not-Inias’s grip was on his hip. “Oh, fuck… Fuck… Yeah, baby. Milk my fucking dick.”

 

The orgasm hit him with such a surprising force that he nearly blacked out. There was only pleasure and nothing else and, for a moment, Cas felt light, as if he was flying.

 

Not-Inias moaned as his hips stilled. He could feel the man’s cock twitch as he spilled into the condom. Not-Inias pressed his forehead against the back of Cas’s neck as he steadied his breathing. A moment later, he let out a deep exhale and pulled out of Cas.

 

Cas winced for a moment when Not-Inias pulled his cock out of him. That had hurt a little and his hole felt like it would probably start hurting in a few hours, too. But fuck, it had been worth any pain that would follow. Cas turned around and smiled at Not-Inias as he was still trying to catch his breath. "Thank you."

 

Not-Inias chuckled as he pulled off the condom and tossed it into the toilet. “You were a great fuck. Lookin’ forward to seeing how much of a self-fulfilling prophecy you become.” He pulled up his pants and pressed a kiss to Cas’s lips. “I’m usually here on weekends. Hit me up if you want another round.”

 

Cas nodded, still smiling from the high of endorphins coursing through his body. “I will.” He bent over and carefully pulled up his pants, tucking his shirt back in.

 

Not-Inias nodded and opened the door of the stall, disappearing back into the bar before Cas had even buckled his belt.

 

Cas concentrated on fumbling with his belt, suddenly feeling too relaxed to do anything. He chuckled again as he finally managed to buckle his belt and left the bathroom to go back to Dean.

 

Before he sat down next to Dean, his gaze fell on the clock and it reminded him coldly that he had forgotten about his “date” with Jerry. His gaze wandered through the bar, but he couldn’t spot Jerry anywhere, so he went back to Dean and sat down next to him.

 

“Hey,” Dean greeted as he handed him back his beer. “Bad news. Jerry shot me a text. He’s not gonna make it tonight.”

 

Cas felt relieved by that news and nodded. "I'm sorry for making you wait here all alone."

 

Dean shrugged. “Got hit on a couple of times. So I guess somebody’s not the only pretty boy in the bar.”

 

Cas chuckled at Dean and gave him a soft smile. "I could have told you that."

 

“Well… You wanna call it a night? Give punching your v-card up until next time?”

 

“Actually…” Cas scratched the back of his neck.

 

Dean’s eyes widened and he barked out a laugh. “I’ll be damned.” He shook his head in amusement and moved to stand. “Come on, then.”

 

Cas chugged the rest of his beer and stood up as well, following Dean outside with a huge grin on his face when he remembered how nervous he had been, and how amazing his first time had turned out to be. Unexpected, but still amazing.

 

As soon as the door shut behind them and they moved towards the parking lot, they turned at a sharp bark of, “Hey!”

 

When they turned around, the first guy who had hit on Cas that night was approaching them.

 

Dean stepped in front of Cas and waved his hand at the guy. “Buddy, he already told you he’s not interested. You’re bordering on pathetic now.”

 

The guy sneered at Dean. “Well, he’s not interested in you either. He was fucking some other guy ten minutes ago in the john. Thought you’d like to know your boyfriend is a huge slut.”

 

At that Dean chuckled and used his height to intimidate the man. He stepped up to him, gazing down. There was a good few inches in height difference. “Doesn’t matter. Either way he’s comin’ home with me.” Dean turned back to Cas and gently palmed his lower back to turn them away from the guy.

 

Dean craned his neck to look back at the guy over his shoulder. Cas watched his every move in curiosity. Dean winked at Cas and moved his hand lower, cupping his ass and grabbing a firm handful in obvious display for the stranger’s benefit. He then waved at the man with his other hand.

 

Cas closed his eyes for a moment, letting out a soft moan with the feeling of Dean's hand on his ass.

 

At that Dean let out a genuine laugh. He shook his head as they reached the Impala. Releasing his hold on Cas, he looked at him with an amused smile and said, “Slut.”

 

"I think Not-Inias called me a whore," Cas replied dryly before he went to the other side of the Impala to get in.

 

“The fuck was the guy’s name?” Dean shook his head as he slid into the driver’s seat and started the engine.

 

"I don't know his name. He said I could call him whatever I wanted," Cas tried to explain before he leaned back in the seat of the Impala. His tattoo didn't hurt as much in that moment. "I was attracted to him because he looked like Inias. But other than his appearance, he was nothing like him, so I called him Not-Inias."

 

Dean looked at him, his mouth agape, expression entirely amazed. “Your first time was in a dirty bar bathroom with a guy who’s name you never got?”

 

Cas nodded with a grin before he tiredly replied, "The new me. That's apparently how I roll."

 

The expression on Dean’s face instantly changed from stunned to pained. He almost looked broken. Before he could ask, Dean braced his hand on Cas’s shoulder and licked his lip before using his other hand to emphasize his words. “I’m gonna need you to listen to me very carefully, okay?”

 

Cas squinted his eyes at Dean before he nodded. “Alright.”

 

Dean took a deep breath before he squeezed Cas’s shoulder and said, “I know you used to belong to a much better club. I know that there’s a part of you that feels broken… useless, because you don’t have your wings. But that couldn’t be farther from the truth. You aren’t my best friend because you’re an angel, or because you could use your mojo to help me and Sammy. You’re my best friend because of this…” He pointed to the left side of Cas’s chest.

 

“The part of you that helped us when it was against orders. The part of you that risked everything for me and my brother time and time again. So you don’t need to drown yourself in sex, or drugs, or decadence. Indulge, sure, but don’t get lost in it. Because the most valuable part of what makes you, you? No one can fucking take that away. So please, promise me… Don’t lose it.”

 

Cas stared at Dean, his heart painfully skipped a few beats before he looked away as his eyes started to burn. He pressed his lips into a thin line, unable to look at Dean.

 

With a few words, Dean had managed to pierce through the wall he had built up over the years. A wall made out of insecurity, worthlessness, and staggering guilt. He just couldn't deal with the mess that laid in its wake. Dean had said everything he longed to… No, he needed to hear. But he didn't feel ready for those words.

 

"I want to go back, Dean," he whispered after a long moment.

 

Dean nodded and let go of Cas’s shoulder. Bracing his hands on the wheel, he started pulling out of the lot, back onto the road. Cas had no idea how long it had been before Dean finally broke the silence between them.

 

“So, I thought you never did any cloud seeding in Heaven?”

 

Cas turned his gaze away from the blackness of the night that was rushing by them to look at Dean with a tired, confused gaze. "I never had sex with another angel."

 

“I dunno, man. Fucking a rando ‘cause he reminded you of an old friend. Not sure I believe you.” Dean had a smirk firmly in place as he glanced over at Cas.

 

Cas turned to look through the windshield. He smiled softly when he thought about Inias. "Inias and I were more than friends. But we never had a sexual relationship."

 

Dean smiled back. After a beat, he stroked his chin and said, “Alright. I gotta ask. If you didn’t even get the guy’s name, did you even get a good look at him? I mean, did you guys even speak?” His tone was light hearted and teasing.

 

Cas turned to look at Dean. "I was so nervous, but what this man did to me, Dean... I don't know. I think I finally understand why so many angels chose to fall for this." He chuckled as he shook his head slightly. "We didn't talk much and he turned me around to fuck me, so I can’t say I got a good look."

 

“Damn, Cas,” Dean breathed out in a laugh. “You really are a slut.” The way he said it didn’t sound anything like an insult.

 

Cas shot Dean a questioning look. "Not-Inias did that a lot. He said things to me that sounded insulting, but didn't feel that way. More like the opposite."

 

Dean looked at Cas in surprise. “Like what?” he asked hesitantly.

 

"He liked to call me a needy whore and that he couldn't wait to have me again after I've ridden every guy in town." When Cas repeated the words, he felt his cock twitch again and almost chuckled how easily those words had such an effect on him.

 

Dean let out an almost impressed scoff. He smirked at Cas. “You’re kind of a freak, Cas.” He nodded and added, “I like it.”

 

Cas chuckled and shifted in his seat to look at Dean fully. “I think I really like sex. And now that I have a comparison between sex with a woman and a man, I think I will stick to men.” Cas scratched his head, before he added, “I just don’t get kissing.”

 

“What do you mean you ‘don’t get’ kissing?”

 

Cas shrugged, scrunching up his nose. "It feels nice every time I kiss someone, but it's not... it's not what I thought it would be. It’s always described in literature and movies as something that feels amazing and special, but... not with me."

 

Dean nodded as he looked over his shoulder to merge onto the highway. “Some people just suck at kissing. Once you get a good kisser, you’ll know.”

 

Cas thought about it for a moment. He couldn't imagine that Not-Inias had been a bad kisser. "Are you sure about that?" he asked skeptically.

 

“Trust me. I’ve had plenty of bad kissers myself.”

 

"I don't think Not-Inias was a bad kisser. He seemed to have a lot of experience. Maybe it's me." Cas tilted his head before he nodded. "It's probably me."

 

Dean chuckled and shook his head. “It’s not.”

 

Cas raised an eyebrow at Dean. "You don't know that, Dean. And it would make sense. I haven’t done much kissing in my life."

 

“Dude…” Dean braced his arm along the backrest of the front seat and gave Cas a pointed look. “You left a friggin’ demon in a lust-filled daze from a kiss. There’s no way you’re bad at it.”

 

"It may have felt good for Meg, but it didn't feel special to me." He chuckled when he thought back to that time. "I only kissed her back because I thought that was the appropriate response to what she had done. I mimicked what I saw on TV because I thought I had to. Nothing more."

 

Dean laughed and shook his head. “Typical. That kiss probably rocked her little demonic world and you thought you were being a gentleman.”

 

“So it’s just the others?” Cas asked slowly, still not really believing it.

 

“Yeah, I promise. When you get kissed for real, you’ll know.”

 

"So theoretically, I just need to find a good kisser to experience a great kiss?" Cas hummed with a flirty and playful grin in Dean's direction. "Where would I find one of those?"

 

Dean rolled his eyes and pushed Cas’s face away. “Slow your roll, sex fiend. I ain’t that kinda gal.”

 

Cas chuckled again, still noticing the effect of the two beers and how relaxed he felt after he had sex. “So, Dean… what kind of girl are you?”

 

“The wine and dine kind. I don’t put out until the fifth date,” he countered without missing a beat.

 

Cas hummed before he shook his head. "Another reason why I should stick to men. No dates. No attachments. Just sex." He sat up in his seat before he looked at Dean again. "You’ve been doing the same thing for years with women. Does that mean you're a slut, too?"

 

“I like to think of myself as worldly,” he said haughtily as he straightened an invisible tie.

 

“You’re a slut, Dean,” Cas repeated, just because it was true and he could.

 

“Well,” Dean said as he smirked at him, “takes one to know one, Cas.”