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If You're Talking About A Game I Can Win

Summary:

Benny's a regular at Purgatory; even has his own stool. The food's decent, the beer's great, but it's the people that make it feel like home. The regulars are buddies, and the employees treat Benny like family. Benny wouldn't mind making that more of a reality by dating one of the brothers, but he's not sure which one's already in a relationship.

The night he's invited to stay after to find out the truth does not go a way he could ever have expected.

Notes:

Prompt: Sam and Dean run a hole-in-the wall bar that specializes in tap beer and lots of whiskey. Benny’s there enough to have his own barstool, that the other regulars are aware not to take. He lingers longer and longer every night, spending more time talking to the brothers than actually drinking any of the beers put in front of him. Finally, Dean blushes and stutters his way through an invitation to come home with them - them, and that’s how Benny finds out they share a lot more than just a last name. - thedropoutandthejunkie
(I added Cas; hope you don't mind too much!)

Written for SPN Poly Bingo
Square: Hurt/Comfort

Written for Dean Winchester Bingo
Square: Bed Sharing

Written for Sam Winchester Bingo
Square: Sam/Benny/Dean
(Added Cas, again)

Written for SPN Genre Bingo
Square: Secretly Dating

Work Text:

Purgatory was Benny’s favorite bar. Best burger in town, limited selection of booze but it was good booze. You could count on it getting rowdy on a Saturday night, but the employees always kept things under control. During the week, it was quiet. The regular crowd all knew each other, and when the rowdiness got too bad, some would even pitch in. But what Benny liked best about Purgatory was the employees.

Dean was the burger chef. When it was slow, like now, he’d come out and talk to the customers. He was also responsible for choosing the beers and whiskeys they kept, which is what they were known for. Sam poured drinks and took orders back to Dean, and used his 6’4” intimidation power to break up fights. Dean and Sam were brothers, and you could tell they had each other’s backs from the easy way they worked together. They didn’t even have to talk to communicate complex things.

Benny wasn’t sure how Cas fit in. Officially, he was the bouncer. He also cleaned tables, helped Sam pour drinks, brought food out, and basically did whatever needed to be done. At first glance, he was the least intimidating of the employees, but it was deceptive. Every regular there remembered the first time they’d seen Cas in action. He was good. Most of the regulars were convinced he was dating one of the brothers, but there was a good-natured shipping war about which brother he was dating.

Benny had been coming here long enough that everyone knew the third stool, the one with the puncture marks in the dark red leather, was his. All of the regulars had their habitual seats, and their routines. Often, Benny got in at 7:30 to find a shot of his favorite whiskey and a burger the way he liked it waiting for him.

Tuesdays were slow, and it was slowing down. Dean came out and took the stool next to Benny’s. “Hey. What’s going on?”

“Cas had to break up a shouting match. That new kid, Kevin, got his first taste of the shipping war, and he suggested that we just ask Cas.” Benny huffed a laugh. “Bobby got a little sarcastic and fired back, and things started gettin’ a little heated.”

“I was wondering why Bobby and Rufus left so early.” Dean shook his head with a huge grin. “Why don’t you guys just ask Cas? Or me or Sam for that matter?”

Benny rolled his eyes and took another sip of his beer. “C’mon, Dean. It’s a dumb fight that ain’t none of our business to begin with. We like comin’ here. Not gonna snoop into your personal business.”

Dean walked around the counter and poured himself a Coke. “You’re curious, though. Aren’t you?”

“Well, yeah. Course I am.” More than most of the regulars, Benny wanted to know the answer. If he ever did, he was going to try to find a way to ask out whichever brother was available.

Dean looked at him for a long moment. “It’s Tuesday. When we shut down, Sam and Cas are gonna head out back and cuddle up on the sofa to watch whatever nature documentary they’re on this week. I don’t pay much attention.”

Benny could see it. “Why’s it matter that it’s Tuesday?”

Dean laughed. “We trade off who closes the place down. I get Tuesdays and Thursdays. Sam takes Friday and Sunday because those are the biggest paperwork days, and Cas does Wednesday and Saturday.”

“Oh. Makes sense.” Benny took another sip of his beer. “You realize that don’t exactly answer the question, right?”

“Yeah, I know.” Dean winked. “You’re missing some pretty important context. Sam doesn’t let most people touch him, and there’s a good reason for that. For a long time, me and Cas were the only exceptions.”

Benny’s brow wrinkled. It’s not that he went out of his way to touch Sam, but he did touch him. “He’s never said anything to me about it. I don’t mean anything by it, but…”

Dean punched Benny’s shoulder. “Calm down, man. If you were bothering Sammy, he’d’ve said. Or gotten me or Cas to talk to you. He likes you.”

“Still, he coulda…” Benny narrowed his eyes at Dean. “That’s still no answer, you know.”

Dean smirked. “I know.”

“When you say he likes me…” Benny didn’t want to cause problems, and it kind of sounded like he was.

“I mean like he’s hardcore crushing on you.”

Benny’s stomach fluttered. He liked Sam. But there was one problem he wanted cleared up before he did anything. “Him and Cas… they aren’t together?”

“Oh, they are.”

Benny blinked a couple times. “Then why tell me? I ain’t gonna…”

Dean rolled his eyes. “Because they made me be the one to talk to you. Sam’s too scared and Cas… well. You know Cas.”

“I’m confused. And a little worried about Sam bein’ scared of me.” Cas crossed the room to the front door. “And you’re closing. I should…”

“You should stick around past close. Once we’ve cleared out everyone else, I’ll clear up the confusion.” Dean finished off his Coke.

Benny finished his beer, and Sam came to refill it. He then headed over to another patron, someone Benny didn’t know, to tell him they were closed. The guy got upset, pointing to Benny. “If he gets to stay, why don’t I?”

“Because he’s our friend, not just a customer. Finish your drink and get out of here, or I’ll remove you.” Sam crossed his arms and straightened up to his full height.

The guy didn’t get out. Instead, he demanded another beer. Castiel came over and grabbed him. “Come on. The man asked nicely, now you get escorted.” He hauled the guy to the front door and shoved him out, with Sam following.

Once the guy was gone, Sam glanced over at Dean. Dean gave a short nod, so Sam bent over to kiss the top of Cas’s head. “Thanks, angel.”

“Of course.” Castiel took off to start the closing chores. Sam went back to the bar and pulled the drawer out of the register to count the money, not too far from where Dean and Benny were talking.

Dean got up and poured three beers. He shoved one over to Sam, who took it with a quick smile, and set another over near Cas. Cas signaled his acknowledgement without leaving his sweeping. Dean took the third beer and came back. “Okay. You know the three of us find the shipping war hilarious.”

Benny snorted. “Yeah, otherwise you’d put a stop to it.”

“No one’s got it entirely right. Some people have it entirely wrong, the people who think Cas is our cousin or something, but most people have it at least part right.”

“Sam and Cas.” Couldn’t be that simple.

Dean smirked. “Yeah. Me too.”

“You’re with Cas too?” Well, that did explain why both sides had such convincing arguments. Dean nodded and took a swig of beer. “So if Cas gets to be with you, Sam’s allowed to have another boyfriend too?”

Sam cracked up. “Come on, Dean. You’re terrible at this.”

“Shut up. You’d be even worse, or you’d be the one doing this.” Dean glared at Sam. “I know I’m gonna have to come out and say it, but we’ve spent so long being so cautious it’s hard to just blurt it out.”

“Yeah, I know.” Sam grinned. “Maybe we should’ve let Cas handle this. He usually has no problem coming right out and saying stuff, no matter how awkward.”

Benny looked between the brothers. “What’s goin’ on here?”

Sam smirked at Dean. Dean sighed. “Sammy has another boyfriend. If this were just about Sam having a thing for you, we’d have left him to deal with this on his own.”

Sam wrote down his count and came over to Dean and Benny. “I’d have told you about Cas. And Dean and Cas. And… really, the only difference would’ve been that you’d be hearing this from me instead of Dean.”

“Hearin’ what?” Benny tried to swallow his frustration with the beer.

“Me and Sam.”

Benny looked between them. “What about you and Sam?”

“We’re more than just brothers.”

Benny’s shock must have been obvious, because Sam leaned on the bar. “We wouldn’t blame you a bit for running away, never coming back to Purgatory. We know it’s weird and a lot of people wouldn’t want anything to do with us if they knew. But please, we’re trusting you not to cause us trouble. It’s fully consensual. We’re not hurting anyone, especially not each other or Cas.”

Benny finished his remaining beer in one gulp, giving himself time to think a little about his response. “Not gonna cause trouble… or leave the bar. What you do in your own home ain’t none of my business.” Disappointed though he might be. He was a little irked at Dean for leading him on, but he understood the stalling before admitting to sleeping with his brother. Same with Sam being scared to talk to him - it wasn't him, it was what he'd be admitting to. “What I don’t get here is why you’re tellin’ me this. I’m honored you trust me, and I promise I’ll live up to it, but why take that chance?”

Tension drained out of both Dean and Sam. Dean explained. “One of the things Cas does for us is keep an eye out for potential problems. He’s got the best instincts I’ve ever seen – only been fooled once that I know of. So when you started comin’ in every night, Cas started keeping an eye on you.”

Benny shook his head. “I’m not gonna cause problems for you guys. Wasn’t gonna try anything until I knew the story, wouldn’t try anything while you’re at work, and I never see you outside of the bar.”

Dean put a hand on Benny’s shoulder. “Took Cas all of two minutes to work out that you were gonna keep to thinking and looking at us. Thing is, we kinda…”

Sam swallowed. “If anything, this is my fault. I’m the one who caused this problem. I don’t know if you’ve noticed, but I keep my distance from most of the customers, even the regulars. You, I let in closer. Usually when I do that, I end up having a breakdown that one of these two have to get me through. Not with you.”

“Cas and I started watching you even closer when we realized it had been a month or so and nothing bad was happening. We don’t mind someone stepping out, but we want to be sure that when they come back, they’ll be in one piece. Usually it’s me. At first, we were just screening for Sammy before we gave him the okay to talk to you. Didn’t stay that way.”

Benny looked over to Cas, who smiled at him when he noticed. He looked back at the beer Sam had refilled for him. “Still a bit confused.”

Dean nodded. “See, now you know what you need to if you’re gonna respond to getting hit on. Kinda thought some of this might make a difference to you. Not the kind of thing you wanna find out after you’ve fucked Sam’s brains out.”

Benny took a long drink. “So I am getting hit on.”

“Yep.”

“By who, exactly?” Sam didn't need his big brother to do his hitting on people for him, Benny was sure of that. But the conversation had been oddly focused on Sam for it to be Dean.

Dean laughed at that. “Committee. All of us like you. You can pick who you want, and if that changes sometime, just talk to whoever’s relevant. Or you can have us all. One-night stand or full integration into our relationship. That’s what we want, for you to be family. But it’s your call.”

“Wow. I, uh…” Benny had never even dreamed of this. “Gonna take a while to sink in here.”

Sam grinned and he ducked his head. “Take as long as you need.”

Benny took another drink of his beer. “Sam? Can I ask…?”

Sam’s smile faded, and he dropped his head. “Yeah. Give me a minute, it’s hard to talk about, but you deserve to know.”

“I’ll start it, Sammy.” Dean got up and went over to Sam and put an arm around him. “Sam and I are brothers. Everyone knows that. Cas moved in down the street when I was twelve, Sam was eight, and Cas was ten. The three of us became nearly inseparable until Cas left for college. Cas was already in love with us both, and we both loved him. I was the one who mustered up the balls to say something before he left. Sam took it pretty well, considering.”

Sam took up the story there. “By which he means I stayed their friend, but decided to go to college as far away from them as I could get. Give myself some time and space to get over Cas, give Cas the time and space to get over me. It was working, too. I met a guy. Luce.”

Cas came over to them then, cleaning forgotten as he took Sam’s hand across the bar. “Dean probably mentioned my instincts have only failed us once. Luce is the once. I wasn’t happy when Sam showed up for Christmas with a boyfriend in tow, and I hated Luce immediately. Under any other circumstances, I’d have told Sam that and Sam would have trusted me, but given the situation… I didn’t speak up, because I thought it was jealousy, and even if I had I certainly couldn’t have blamed Sam for ignoring me thinking it was jealousy.”

“Wait, you all knew Cas was in love with Sam too?”

“Did by then.” Dean shrugged. “If I’d known before I took my chance with Cas, I wouldn’t have, but by the time I worked it out both Cas and Sam told me it wasn’t going to be a problem and that I shouldn’t break up with Cas just so Cas would be with Sam. The idea of doing what we are now didn’t occur to us until after Sam left for college and we realized just how much we missed him, and by the time we'd worked that out, Sam had Luce.”

Sam chuckled. “As it turned out, we all wish it had. Luce turned out to be seriously abusive. After Christmas, I didn’t speak to Dean or Cas for nearly a year. Next time they heard from me, I called Dean and begged him to come get me. Dean was pissed at me for not calling, but when he heard Luce hit me for calling…”

“Dean grabbed me and we hauled ass to Palo Alto. The whole way there, one of us drove and the other slept if he could and cursed ourselves and Luce if he couldn’t. I spent most of the drive there in tears. I blamed myself for not speaking up and making Sam believe me.”

Sam swallowed hard. “I thought it had been bad before, but it was terrible, those two days between calling Dean and them arriving. You’re probably gonna call me overdramatic, but if Dean and Cas had been five minutes later, they’d probably be in jail for murder.”

“Pretty sure most juries would let us off for justifiable homicide, coming in and finding my little brother dead,” Dean snarled. Cas shot him a warning look. "What? The assault charges got dropped soon as the bruises around Sam's throat became obvious! Doc said there was enough force to kill!"

Sam shot Dean a glare, too, and Dean backed off. “At first, I wouldn’t let them touch me either. Too scared, after Lucifer. It’s why I usually stand back and let Cas handle the fighting. I can fight, when I need to, but I pay for it afterwards.”

“Me and Cas, we felt so guilty and scared, we let him set whatever boundaries with us he needed to…. Right up until I noticed he wasn’t sleeping.”

“I couldn’t sleep," Sam admitted in a whisper. "Every time I closed my eyes, I saw Luce’s face, felt his hands on me.” Castiel came over and wrapped his arms around Sam.

“So one night I decided enough was enough, and I shoved in bed with him. After the initial panic attack, Sam actually fell asleep with me holding him. Cas tried the next night, and it worked with him, too.”

“Dean and I would switch off, but then I got stupid. I didn’t exactly plan it, but I knew it was Sam with me and not Dean when I started kissing him. To this day I don’t know why Sam let me, but I slept with him.”

"I let him because I was so tired of fighting... fighting the memories of Luce in my head, fighting the feelings that had never really gone away and came flooding right back when they saved me, I knew it would probably make Dean mad but I just didn't have it in me to say no, not when I wanted it so much."

“They confessed first thing in the morning. I kinda knew, or at least figured it was going to happen, even wanted it to. But hearing them say it made me mad. So I got revenge. Took my turn holding Sam that night, and I slept with him too. Wasn’t until the next morning that I realized the full extent of what I’d just done. I mean, cheating on Cas, I knew I was doing that. My brain just kinda skipped right over the part where I was sleeping with my brother.”

Sam laughed a little. “I knew I was sleeping with my brother. It’s just that after he saved me from Luce, I no longer cared. At least I could trust my brother not to hurt me. And I just assumed he knew what he was doing.”

Benny choked down the bile. He wanted to hunt down Luce and rip his head off. “Luce in jail?”

Sam shook his head. “Actually, his sentence would’ve been up a couple years ago. So he’s probably out now.”

“No, he’s not,” Cas growled. “He keeps getting himself in trouble, bad enough that they add time to his sentence. I think he’s currently up to five more years. I know you’re not worried about him, Sam, but I am. I can still see his hands around your throat when I close my eyes.”

Sam gave Cas a soft smile and planted a kiss on his temple. “You know the only reason I don’t worry about him is that I know you’re keeping tabs on him and I’ve got you and Dean between me and him even when he does get out.”

“Wow.” Benny stared at his beer. Everything Sam had been through, Dean and Cas made sense, they were old friends. No matter what happened here, Benny would always be honored by the trust Sam was showing in making this move. “And I really don’t set you off, Sam?”

“You really don’t. If you choose a one-night stand, I can hold it together even if you do start when things start getting more intimate. Relationship I’m probably gonna want to take a little slower than either of these two would, but I’ll get comfortable quickly if I’m not to begin with.” Sam reached out and took Benny’s hand. “If you did set me off, I’d have talked to you about it.”

“Good.” Cas drifted off to get back to work, as did Sam, and Benny blinked. “Wait a minute. Aren’t you and Cas supposed to be…”

Sam ducked his head and laughed. “Yeah, but if we’re curled up out back watching Cosmos, we’re not out here to hear how things go and answer questions if you have them. Besides, we kind of owe Dean for making him do most of the talking.”

“True.” Benny watched them go about their work, Dean now getting up to help. “If I come in, I mess up your plan. You’ve got it figured out.”

Dean shrugged with a grin. “We’ll have to work out days, but the easy solution is that two of us close while the other one takes off with you. Closing really doesn’t take all that long, plenty of time for date stuff after we finish. Only reason we’re usually here as long as we are is so that the other two can have some time without us. And, well, you’re here almost every night anyway, so even if you don’t start coming by on Mondays to see some of us, we’ll still get to see you most nights.”

Benny got up and headed over to pour himself some more beer, which made Dean chuckle. “Just curious… what do you think I’ll do?”

Dean shrugged again. “I know you’re interested in Sammy, pretty sure you’re interested in me. Haven’t seen you looking at Cas, but I always figured that was because you were pretty sure he was taken. You never picked a side in the shipping war, but you also never joined the side of neither. But predicting how someone responds to the suggestion of a poly relationship? Never easy. One of the reasons Cas and I didn’t call up Sam and ask him was that I was pretty sure he’d say no. Even after we’d both slept with him, I thought he’d say no.”

Sam looked over with a huge grin. “And then I went and brought it up myself. Second scariest day of my life, because I needed that support system and it was falling apart and I didn’t know if my suggestion would help put it back together better than ever or crack it apart so badly that I lost it. Thankfully, it worked out, and now we’re here.”

“Well, you’re not wrong,” Benny admitted. “Had a thing for both of you, and wouldn’t mind givin’ this a shot, long as you’re sure I ain’t gonna mess up your balance. Let’s do this, then.”