Prompt #4: Fake It Til You Make It

AN: Done for a prompt that wanted a reverse of the episode where Dean had to walk Charlie through flirting. This was actually really hard, because Dean is Dean. He can charm anyone and would have no problem coming off as possibly flirting with a guy if that would get him information. So I had to give him a reason for this particular situation freaking him out, to his surprise and the surprise of his friends, so I could fill the prompt.
Warning: References to past sexual harassment of a character as a minor.

It was a good thing only the front of the private gym was glass, because Dean visibly doubled over and having a panic attack would not have been good. As it was, he was ducked around the corner- hidden from anyone inside- and trying very hard to get his breathing back to normal. He was failing rather spectacularly.

He had his phone out and dialed, pocketing it as soon as his ear piece started to ring.

Sam picked up. "Hello?"

"I can't do this," Dean blurted out. Sam started laughing, the jerk. "Sam, this isn't funny. I seriously cannot go in there and-and-" He swallowed, remembering the rainbow sign above the door, the clear 'members only' lettering on the glass under the gym name. "I cannot go in there and pretend I am gay in order to get a gym membership we only need for a couple of days."

Sam was still laughing at him, despite the rising hysteria in Dean's voice. All the while, it was getting harder to breath, and all Dean could think of was being years younger and getting sized up by men entirely too old to be looking at him like that. He was reminded of unwanted gropes by strangers, and offers that had been more terrifying than appealing. The idea of what they expected him to pretend was bringing up every time he'd ever felt utterly vulnerable and out of his element, young and threatened by unwanted advances. Sam laughing at him was not helping.

"Sam!" he hissed into the phone, and that was what made his brother realize that something was actually wrong.

"Oh shit, Dean, you're being serious." His voice was instantly soothing. "Look, man, calm down. I thought you said you could handle this."

"You and Cas were still researching what the victims have in common and what caused their injuries," he wheezed. He doubled over, taking in long breathes through his nose and exhaling through his mouth.

He could hear muffled movement on the other end, and imagined Sam holding the phone between his head and shoulder. "Dude, I do not understand why you are panicking like this." And Dean would die before Sam ever found out as well. He'd made doubly sure no one ever looked at his brother the way he had been. "It's a job, Dean. Lie your way through like always. You flirted with that security guard-"

He straightened, leaning back against the building. "I was walking Charlie through how to flirt as a girl with a guy. I cannot go in there and just start flirting with some random guy-"

More muffled movement and voices and then suddenly it was Charlie's voice in his ear. "Dean? Charlie."

"Oh thank God," he sighed. "Don't laugh. Get away from Sam. I don't being laughed at right now."

"Don't worry. I've left him and Kevin in the library. I'm headed towards my room. What's the problem?"

He shook his head as though she could see the movement. "I can't go in there are pretend to be gay- no offense, Charlie, but I can't just- I mean, what do I do if the guy hits on me? Sam and I have never even joined a gym before. Everything in me wants to flirt with the girl at the counter and use intimidation with the guy to get information."

"That is so not gonna work," she said, voice changing as she put him on speaker phone. He could hear her fingers on the keys of her laptop. "Look, Dean, I don't know what your childhood trauma is-"

"What? I never said-"

"Dean," she interjected, firm but not angry. "You are not a homophobic ass, so you panicking is not that. You are freaking out from something else you are relating this to, and the fact that you don't know what to do if he hits on you, while everything wants to be aggressive in self-defense, tells me it's a childhood trauma." Her voice turned gentle, "They're just people, Dean, everyday people. It's a business; they want your business. They will be friendly, possibly charming, it's good customer service, not a threat. Be friendly and charming right back. You are new to the area, don't know anybody, looking to get plugged into the community and make friends."

His breathing had returned to normal and he was nodding, her voice reassuring and calm. Good customer service wanting his business. New in town. That was easy.

"Ask for Michael, he's the owner and manager. He's about your age, looks like a fitness trainer on TV, dark hair and nice smile. One of your neighbors down the street directed you to this gym, said Mike could tell you everything the gym had to offer and local athletic fundraisers and benefits. Be nice, you want information, he has it."

He nodded again, pausing in rounding the building to go inside. "What do I do if he or someone else does hit on me or asks about my… partner or boyfriend or whatever?"

"If he hits on you, subtly bring up your boyfriend, or your girlfriend if you want to tell him you're bi, but dating a guy will just be easier. Or flirt back, pretending he's Cas if you can't flirt with him on his own merit."

"How would pretending he's Cas make it easier to flirt with him?" he demanded.

She scoffed. "Dean. You flirt with Cas all the time. You are so heads over for him that it's not even funny, just completely adorable! Poor fallen angel is probably all confused because of it."

"Why is that?" he asked warily, heart hammering against his ribs for a new reason.

"Because you shamelessly flirt and tease him, leaving him flustered and flushed, and then you never follow through on it, so he probably thinks he's just imagining it, rather than it being something you are actually doing, which you totally are. The two of you have no personal space. And you touch him, all the time, like he'll vanish if you don't. You flirt with Cas, so if it makes it easier to grease the wheels with a little harmless flirting, pretend the guy is Cas."

He snorted as he rounded the building and slipped into the welcoming air-conditioned interior. The guy behind the counter had to be Michael, both he and the young girl looked up and smiled at Dean's entrance.

"How are you today?" questioned Mike in greeting.

The girl went back to filling out forms, brows pinched as she scribbled in boxes.

"Good," answered Dean, head bobbing as he let his gaze do a quick sweep of the mostly unoccupied gym. "I, uh, just moved to town. Some neighbors directed me here when I mentioned looking for a gym. Said to ask for Mike?" he said, letting the last part come out as a question as his gaze returned to the man and then down to his name tag.

The other man's smile broadened, and wow, yeah, Charlie was right, he totally looked like TV trainer. "That would be me," he affirmed, offering his hand for Dean to shake. Dean took the proffered hand while Charlie murmured assurances in his ear. "Mike Turner."

"Dean Winchester," he greeted, internally wincing as he gave his real name. Charlie was soothing him immediately, fingers flying over the keys of her laptop, assuring him she could feed him another Winchester's information to put on the membership forms.

Hand falling away, Michael loosely crossed his arms over his chest. "So what exactly are you looking for in a gym? We don't have classes here, but we do offer fitness training and advice if you'd like, we always have a fitness trainer on hand during regular business hours."

"Ask him for a tour of the facilities," Charlie prompted.

Dean made a circle in the air with his finger. "Can I get a walk-through? Sort of get a feel for the place?"

The other man immediately nodded, stepping out from around the counter and motioning for Dean. The hunter fell into step with him as Mike walked them through the gym, pointing out the different equipment and what it focused on, the newest machines they had gotten, ones they were going to replace with newer models. Dean asked questions and nodded in all the right places. Mike led him into the locker room, and pointed him toward the shower stalls, changing rooms, and toilets, told him they recommended people bring their own locks for the lockers and other various information.

As they were making their way back up to the front, Mike asked, "So what kind of membership are you looking for? We have several packages-"

"My boyfriend and I don't always keep the same workout schedules," Charlie said in his ear, and Dean parroted it back, "so we would need two cards to come in at different times. Do we have to get two memberships or do you have a couple's package?"

Mike nodded. "We do. We also have a family package as well, if you'd like to have up to four people signed up."

Blinking with a start, Dean frowned. "Up to four? Where are we gonna get two other people?"

The other man chuckled and waggled his head back and forth. "Well, if either of you have children over the age of fourteen, housemates also use it, or if you have a workout partner, or a sibling-"

Dean scoffed and waved him off. "Sam can get his own membership." Both Mike and Charlie laughed, and Dean grinned.

"You would not be the first to feel that way. You said you and your boyfriend don't always keep the same schedule?" Dean nodded, and Mike gestured toward the glass doors. "Well, we're open twenty-four seven, but for safety reasons, after ten the door locks and you have to have your key card to get in, someone will be here, of course, but not just anyone is allowed in. What do you and, uh…" He gestured towards Dean.

"Cas," Dean said automatically, and nearly winced. "My boyfriend's name is Cas."

God, he was so glad Sam wasn't on the phone with him anymore because he'd probably would hurt himself laughing at Dean. Meanwhile, the elder Winchester could feel his face heating in embarrassment at the statement. Cas would probably just roll with the lie had he been there. He'd gotten pretty good at improv.

Mike nodded, head angling curiously. "If you don't mind my asking, what do you and Cas do that brought you here and keeps you on different schedules?"

"Work," Dean told him. "Work brought us here and keeps us on crazy schedules. I restore cars, mostly classics…" He licked his lip, and then smiled. "Cas is retired military. He does a lot of research work now, really ought to publish books with all the stuff he knows."

Mike's brows shot up. "Impressive."

The smile on his face turned fond, thinking of his friend. "Yeah, he is." He huffed an embarrassed laugh and scratched the back of his neck. "He's kind of perfect. I have no idea why puts up with me, and don't have a clue what I'd do without him."

Charlie chuckled in his ear. "Look at you gushing your love for the man to a complete stranger. You're embarrassing me, Dean. Ask him about the recent incident. One of the other neighbors said there was just some trouble and someone got hurt."

Dean asked, questioning Mike about the crime in the area or any hostility towards the LGBT community or the gym specifically.

The gym owner assured him they had had no such problems, that it was a quiet community, and everyone got along.

"Ask him if there's an app to track how often you log into the gym for fitness purposes, and if it can be used by all the people on your membership," Charlie instructed. Dean nodded along as Mike told him about a marathon the gym was going to take part in to raise money for the local children's hospital, suggesting that Dean and Cas might like to join up in order to meet people and help the cause. Dean smirked as Charlie scoffed. "What am I talking about? I can just hack their systems and cross-reference all the members comings and goings. Forget I said anything. Don't ask him that."

They talked for a few more minutes before Dean signed up for the gym, Charlie giving him a fake social security number and bank account. Apparently she set up fake identities for them using their real identities given that they had a permanent address now.

"You know," she began conversationally, "you really ought to ask Cas out on a date." He snorted lightly. "I'm serious. He'd say 'yes'. It wouldn't have to be a date-date, just you and him getting time alone. You make time to do stuff with Sam, and with me, and even check in on Kevin, but you never pull Cas aside and say, 'Hey, let's go get coffee, or go to my room, I have lube.'"

Dean coughed loudly, fighting the urge to glance around to see if anyone over heard that, before glaring at his paperwork again and clenching his teeth. She would bring the subject up when he couldn't actually snap back at her.

She cackled with delight in his ear. "Oh I'm just teasing, though I still think he'd be game for that last one as well... Though, not on the first date. Actually date him a while before you go there. He matters more than your previous relationships."

Dean gave a hum of agreement, and could practically see her grinning.

"What would you do without me, Dean? You'd combust is what you'd do. I'm the sister you come to with all these things you can't talk to Sam about."

He made another sound of agreement.

"Seriously, though. Ask Cas out, just go do… normal stuff, rather than letting his every earthly experience be about hunting. Take him for coffee, people watch at the park, go see a movie, go shopping at the local farmer's market for groceries together. You don't have to call it a date unless he specifically asks, then give him the option for it to be a date or not. Guy's in love with you, too, which you have clearly failed to pick up on."

Finished with the paperwork, Dean shook hands with Mike, grinning and accepting the two key cards, before heading out to the parking lot.

"Y'know," he told Charlie, glancing once over his shoulder at the gym, "we actually could just maintain these memberships. I mean, we live fifteen minutes away and it would give us an excuse to get out of the bunker for a while, give us a break when we aren't on cases."

"We'd need more than the couple's membership. We'd have to upgrade to the family one," Charlie pointed out. "It should be fine so long as we don't all plan to go to the gym at the same time, and Sam seems to prefer running outside unless it's flat out raining. I think Kevin is allergic to anything more athletic than track."

Cranking the car, Dean let it idle a moment, gaze focused on the distance. "Hey, Charlie?"

"Yeah?"

"Thanks."

He heard her smile again. "You're welcome, Dean."

The next morning, he watched as Cas made his way into the kitchen, greeting the other occupants of the Batcave before heading toward the coffee pot. Dean caught him before he got there, clapping a hand on his shoulder.

"C'mon, Cas, you and I are going out for coffee." The former angel blinked, surprised, and frowned. Dean swallowed, casting only the briefest of glances over Cas' shoulder at Charlie who was giving him a double-thumbs up and a wink. He looked back at Cas, ignoring the confusion on his brother's face. Kevin was too busy trying not to fall asleep in his breakfast to notice the rest of them. "You want to?"

After a moment's consideration, Cas inclined his head and smiled. "Yes, I'd like that."

Dean grinned. "Awesome."

Please don't forget to leave feedback! We love when you love our work, so please let us know!