Title: A Kiss Too Many
Rating: PG-13
Ships: Dean Winchester/Castiel Novak, Sam Winchester/Jessica, Ruby/Meg Masters, Castiel Novak/Meg Masters
Summary: When Sam decides to have his grooms party before his wedding with Jessica, he brings some of his closest friends along. Dean and Castiel have been drooling over each other but when Sam sets up a plan with Meg, Dean gets a little jealous.

Sam was aware of the true feelings his coworker Castiel Novak and his older brother Dean felt for each other. It was undeniably mutual. Except neither of them had the true guts to man up and ask each other out. Normally Sam didn't intervene with Dean and his relationships, but ever since the incident with Lisa, things have been rough with Dean and relationships. Seems like it's a job for Mister Moose.

Sam arrived at one of Jess' suggested best friend's house, Meg Masters. From what Sam was told, Meg was currently dating a girl by the name Ruby, who he'd met once or twice. Being lesbian, Jess recommended her for Sam's particular plan to set up his brother and coworker.

He strode up to the door and knocked. A chick with curly brown hair that spiraled from her scalp answered the door. She scanned Sam for a minute before popping a bubble from her mouth. "Got to admit, when Jess said tall. She meant tall... Is your penis-"

"NOPE." Sam just nudged by her, refusing to continue the conversation. Meg just shrugged and invited Sam to join her at the table that was placed in the middle of her kitchen. He snuck into a seat and fiddled a hit with his thumbs. "So I was wondering if you'd be willing to help me set up my brother with my coworker. They've been making puppy eyes at each other and continue to just socialize through texting. I'm convinced that Dean just needs the extra push to ask out Cas. Do you think you can do that?"

"Like make him jealous?"

"Exactly," Sam didn't bicker, because it her idea was farther than Sam had ever gotten. He'd planted both of them in the same room together several times, but nothing happened. Perhaps Meg could knock some sense into the destined pair or lovers. He was stressed with Jess and the wedding already, and then Dean dumped Lisa recently creating a deal that Sam couldn't carry anymore. They both needed to face their one issues. Even if he had to strip them both naked and lock them in a cell with only condoms. He was willing to make this happen. Nothing mattered more then making his brother happy.

Castiel would be Dean's happiness.

*****

June 24th, 2016: 4:03 pm
Message received:

Cas: Have you told your bother yet?

Dean: haven't had the time to tell him yet

Cas: Dean, it is essential to inform your bother of our relationship. He has the right to know of our feelings as anyone else.

Dean: i'll get to it Cas. just give me some time

Cas: Are you afraid of his reaction? I'd be more than happy to oblige and inform your brother if it would ease your pain. This is part of our relationship.

Dean: you don't have to do that Cas

Cas: I don't, but I will.

Dean: forget it. he's home now, i'll let him know

Cas: Thank you, Dean. I'll see you tonight.

Dean: you too. love ya

Cas: My affections are reciprocated, Dean.

*****

Dean clicked off his phone as Sam wandered into the house, hair tucked in a bun. "Are you wearing a man bun?" Sam rolled his eyes and huffed, yanking out the bun.

"Jerk," he mumbled, tossing some groceries onto the table. Before Dean could retort back Sam continued, "don't even say it. I'm not in the mood right now. Jess is exhausted for the wedding tomorrow and tonight I have to attend a party I didn't even schedule. Bobby has been complaining that he can't wear his hat to the wedding and now Meg is breathing down my neck-"

"Meg?" the odd name didn't make a connection for a few seconds. "Ruby's girlfriend?" Sam nodded then collapsed into a dining chair. His hair draped it's way in front of Sam's face. It was obvious that needed something to get his mind off of things. As much as Sam didn't want to admit it, this party could possibly make him feel better.

"How's Cas? Assuming you guys have been flirting all day..." was the next comment Sam decided to mutter. Dean groaned a him while beginning to sort the groceries placing the cherry pie on the counter for a late night snack.

"He's fine. Looking forward to the party," Dean realized this was the perfect chance to refer his new relationship to his younger brother. What Sam didn't know was that Castiel and Dean had been dating for a few months now. He'd dumped Lisa a year ago and lied to Sam about it. Honestly, he was afraid of Sam's reaction. That was why he'd been putting it off. Sam was only aware that they'd broken up two months ago. Neither did Sam know that almost every time he "spent the night with Jess" was also a night that Dean was busy with Castiel. "speaking of the trench coat baby-"

No more words came out because the ringtone of Sam's cell was blaring. He sighed then reached into his pocket to whisper, "It's Jess, sorry I've got to take this." Without another word Sam shuffled into another room proceeding to begin a conversation with his fiance.

"Sorry, Cas." Dean mumbled then roamed into his own room to change for the party.

*****

June 24th, 2016: 5:28 pm
Message received:

Meg: Hey, "Large Penis". It's Meg. Making sure I'm supposed to meet up at the Roadhouse at 7:45?

Sam: Yep, thanks for doing this for me.

Meg: Not doing this for you. Doing this for Ruby who is adamant that I start being nicer to people. Starting with your large self who can't even talk to your older brother's feelings, just gets other people to do it for you.

Meg: Ruby said that last text wasn't kind... Sorry?

Sam: Apology accepted. Just please don't upset Dean tonight. He's not fun to mess with when he's drunk.

Meg: Can do.

*****

June 24th, 2016: 6:11 pm
Message received:

Jess: How'd the thing with Meg go?

Sam: Went well. I think Dean and Cas will finally be getting together. After all of the struggle Dean had with Lisa I think Cas can make him happy.

Jess: That's one of the reasons I really love you Sam Winchester ;)

Sam: Oh really? ;)

Sam: What are the other reasons?

Jess: You have a large penis.

Sam: You're no longer allowed to text Meg anymore.

*****

Castiel arrived at the Roadhouse at 7 pm on the dot. Dean, Sam, Benny, Balthazar, Aaron, and Adam were all seated in a large booth in the back. A seat was saved for Castiel next to Dean, who linked his fingers with Castiel when they snuggled up in the booth. Everyone ordered a beer while Castiel sipped on tea. Jokes along with pickup lines were being scattered throughout the men while they munched on cheese fries provided by a "sexy waitress" as Benny continued to refer to her as.

"So Sam, this is your last night as a free man. Planning to do anything before then?" Balthazar spoke once the laughter died down.

"Don't think so, Balth. Jess said it was important to get a good amount of sleep tomorrow." Sam replied then sipping at his beer.

"You better get some sleep, son. She'll keep you up all night long on your honeymoon." Dean sputtered his beer as Adam released the joke. Everyone burst into a laughing fit, including Castiel who found Dean's action quiet amusing.

"How about you Castiel?" Aaron piped from the opposite side of him.

"What about me?" Castiel asked, bewildered.

"Any girlfriend?" Aaron questioned.

"No, relationships that include me often don't last." Castiel lied while watching Dean's eyebrows furrow in puzzlement. "my social skills are also a little rusty."

"Well it seems that girl doesn't need social skills to get in your pants." Benny nodded towards a girl Castiel had seen before. Meg was it? She was obviously raking her eyes along Castiel's figure. His throat closed in, breaths uneven. He noticed green eyes boring into his eyes when he whipped around to find Dean scrutinizing his every move.

"Not my type," was Castiel's response when he dove into a fry.

"Oh come on Cas," Sam urged, "she's hot."

"No, I don't think-"

"Cas! Cas! Cas!" the party began chanting his name, excluding Dean who was practically breathing smoke from his nose.

"Fine!" Castiel gave up, "I'll just talk to her." he attempted to reassure Dean who's face was growing abnormally red by the second. Everyone clapped the blue eyed man on the back before he waddled over to Meg who was beaming when he scrambled into a seat beside him at the bar.

"Hi," Castiel grumbled, faking a smile.

"What a pleasure. Clarence is it?"

"It's Cas- Castiel." he corrected her, biting back his tongue that was absorbing all possible colorful words and puke.

"Well, Clarence, I believe there's more ways I can get you to say your name tonight. How about we head over to my place?" she was now licking at his ear. Castiel abruptly zipped his head away, cheeks flaming with embarrassment.

"No thank you," he noticed the movement of Dean who was dashing into the men's bathroom while he other men were making kissy faces at Castiel. A deep pang of guilt grazed his heart as Dean slammed the door behind him.

"How about you tell me about yourself, Clarence." Meg offered while he began stroking Castiel's thigh. Her legs were now drenched across his lap. He couldn't find his voice to tell her to get off. Before anything else happened he saw the bathroom door launch open and then Meg was smashing her lips to his, dragging her tongue across his bottom lip. He froze and clutched the counter when he heard the faint sound of stomps.

"HEY! WHORE! GET OFF OF MY BOYFRIEND!" it was Dean. He snatched Castiel from the bar stool and swept him behind his back.

"I'm sorry. I didn't-"

"OF COURSE YOU DIDN'T KNOW! YOU WERE SUCKING ON HIS LIPS SO MUCH HE COULDN'T TALK!" with that, Dean was dragging Castiel out of the bar. Sam was hollering at Dean and Castiel but Dean was too caught up in the kiss.

"Where are we going Dean?" Castiel wondered when he yanked Castiel into Dean's Baby.

"I'm going to screw you like no one has ever screwed anyone ever before, Cas. Better start on your pants so I don't have to take longer when we get to my house."

*****

Let's just say that Dean lived up to his promise. Castiel was so horse from screaming Dean's name that he couldn't talk at the wedding the next day, let alone walk comfortably. Sam and Jess ended up getting married and Dean later admitted all of what had been going on with Castiel and him. Dean's favorite part of the wedding was watching his brother say his vows. No, he didn't cry. He sobbed, as Castiel claimed.

While Castiel's favorite part was catching the bouquet.