The next day, Dean came clean with Jo during another Dr. Sexy MD episode. For some reason, the show made him honest.
"I almost had sex with Cas." He said casually.
Jo choked on her beer. "W-wh-what?" She gasped, coughing.
Jo grabbed the remote and this time she turned off the television.
"Yeah." He admitted. "Almost." He added.
Jo stared at him as if he had just sprouted horns and a tail.
"What?" Dean said.
"Castiel Novak, your tutor, Charlie's obsession, and the guy who you think is so damaged you won't even let me tease him about his trench coat? You fucked him?!" She demanded.
"I said almost, Jo. We didn't go all the way."
"Dean, Christ. What is it about this guy? For one thing, Charlie says you actually show up for class now and I assume that's his doing. Secondly, I thought you were over your bisexual phase and had returned completely to women! Since when are you into men again?" Jo said.
Dean rolled his eyes. "Just because it had been a couple of years since I'd hooked up with a dude doesn't mean it was a 'phase.' You of all people should know this." He said, actually feeling rather hurt at her insinuation.
Jo opened her mouth to say something and then stopped. Dean knew he had hit her in a sore spot.
When Jo had come out in high school, everyone in their group of friends had insisted it was a phase. A few of them had quit talking to her. Until recently, her father, Bobby, had referred to that period in her life as 'Jo's experimental era.' The truth was that Jo didn't look like a "typical lesbian" with her long blond hair and affinity for sundresses, which Dean thought was a ridiculous reason for assuming someone was "experimenting." Jo was definitely into women and sometimes Dean felt like he was one of the few people in the world who was totally okay with this.
"I'm sorry." She said. "That was shitty of me."
"Yeah, it was." He said. "But don't worry, little Joey, we are fine." He said wrapping an arm around her and giving her a hug.
Jo relaxed and rested her head against his shoulder. "So, what was it like?"
"It was amazing. Jo, I think I like him, like a lot. "
"Is my Dean in lurrrrrrrve?" She crowed, returning to her usual, sarcastic form.
Dean ruffled her hair. "I don't know, Barbie doll. But it was great. It was sexy and fun and I have jerked off three times in the last day and a half just thinking about it."
Jo shoved him off her. "Oh gross! Dean! I don't want hear about you jerking off! You're like my brother!"
Dean burst out laughing. "Just paying you back for that bitch comment!" He crowed.
Jo got serious. "So you like him? You like this guy enough to date him, be in public with him as his boyfriend and to take some time away from biology and studying and all of that?" She said.
Dean stopped laughing and stared at her. Jo had a point about the 'public' part of the equation. Although Dean had screwed a few guys in the privacy of his own home, he'd never been affectionate with one in public, nor had he ever taken one home to Mom. Jo would know better than anyone what that was like.
"I think so. I think… well, yeah. I do." He admitted.
"Does he know about Sam?" She said cautiously.
"Yeah, he does. I kind of had to tell him about it that night you sent him over in your place. I told him though. I told him almost everything."
Jo's eyes widened. Outside of his immediate family, Jo and her family were the only people close to him who knew about Sammy. He had told Charlie a glossed over version of the story, but otherwise, Sam was his secret.
"So this is a real thing?" She said slowly.
"I think it might be. I don't know, Jo. I haven't felt this way about anyone in a long fucking time. I mean, it's kind of weird that it's with a guy, but in the grand scheme of things, you know that doesn't matter to me." Dean said.
Jo nodded. "What about his… um… baggage? I mean, I really only know what you've told me and what I can glean from being around him, but I'm kind of under the impression that the guy has a few issues."
Dean shook his head. "It doesn't matter to me. That's why I want to go slow with him, but I've got baggage too, so no, it doesn't matter. Sometimes it's best to find someone to share your issues with, you know?"
Jo let out a low whistle. "So, Dean-o, you are falling in love? Is that what this is?"
He just shrugged. He couldn't say that right now. This thing with Castiel had only just begun.
"Speaking of… baggage. No, I don't mean that. Fuck that. It's family. How is your brother doing, Dean?" Jo said.
This time too, Dean told her everything.
The next day, a beautiful and merciful Friday, Dean decided it was finally time to get his small, but beloved circle of friends to hang out outside of lunch. Over a series of text messages, Dean set up dinner and drinks with Cas, Jo, and Charlie. A part of Dean wanted to announce that he and Castiel were 'a thing' now, but he hadn't had the other man's approval, so he did it under the guise of the end of midterms.
The four of them met at a Mexican restaurant in the center of town. They walked because the town just wasn't that big. Sometimes Dean went on drives in his beloved Impala just to remind himself how much he loved driving. The place was popular because it was notorious for serving underage Oregonians huge margaritas.
"I used to drink here all of the time when I was a freshman." Charlie said wistfully as they walked in to the restaurant.
Dean snorted. Charlie had grown up in Plainville, so he was sure she consumed alcohol here long before freshman year.
"Charlie, I love how you're wistful for your hometown, which you currently still live in." Jo said, reading Dean's mind.
He glanced at her and she winked at him. God, he loved Jo.
"I don't know why you always make fun of me for being a townie. This place is amazing. There is a reason I didn't go to Portland." Charlie said, faking annoyance. Dean could tell because she was smirking.
"Don't worry, Charlie. I love it here too." Castiel confided as they sat down. "If I were a townie, I would never leave either."
Charlie looked slightly outraged, but Castiel was radiating honesty and light, clearly not understanding the dynamic between the three of them, so she didn't say anything. She simply patted him on the shoulder.
"Cas, you are such a dear." She said. "You are just the cutest thing! I am so happy you are Dean's tutor!"
Castiel just smiled, a huge smile, a smile that looked innocent, but wasn't, because he was currently rubbing his hand up and down Dean's thigh under the table.
Dean gulped and shifted in his seat, trying to look like he wasn't sprouting a huge boner at a family restaurant, with his two best friends sitting directly across from him. He knew it going to be a long night.
One margarita and two bowls of tortilla chips into night, Dean was visibly sweating. Castiel's hand had continued to paw at him under the table, at his thighs, one or two discreet swipes at his crotch, and at one point Cas had actually attempted to play footsie with him. He kept pushing his hand away, but the other man was persistent. Dean had no idea Castiel could ever be this brazen, but he guessed that Cas was just really comfortable with Jo and Charlie.
"So I'm thinking about getting a tattoo." Charlie said, running her finger around the rim of her enormous margarita to get at the salt.
"What tattoo is that?" Castiel said brightly. Too brightly, because he was currently curling his fingers around Dean's inner thigh.
"Now, don't laugh, but I'm thinking about getting Princess Leia in a slave bikini straddling a 20-sided die. Maybe on my ribs or my thigh." Charlie said, tucking a piece of red hair behind her ear.
It worked because Castiel stopped his groping to gape at her. Dean just chuckled.
Jo, of course, burst out laughing. "What the fuck, Charlie? That is the most ridiculous thing I have ever heard of, and this is coming from you!"
"I don't know you guys, I was drunk at Seattle Comic-Con last year and this guy drew it for me and I've always really liked it." Charlie said helplessly.
"Well." Dean said. "I'm sure that no one else in these Americas has that tattoo. At least it'd be original."
"See, Dean gets me. Dean, you think Princess Leia is a babe, right? What about you, Cas?" Charlie said.
"I'm more into Han Solo, myself." Castiel said, waggling his eyebrows at her. He took an enormous drink of his margarita.
"Really now?" Jo said. "Cas, I never would have guessed!"
Jo winked at Dean again and he had to restrain from pouring his drink on her head.
"Isn't it obvious?" Cas said, giggling. His tolerance was low. Dean had to remember that.
Charlie just looked shocked, but she quickly regained her composure and gave Castiel an easy grin. "Cas, I am so glad you started hanging out with us. I can't believe it took until our senior years to discover you."
"He's a diamond in the rough." Dean said.
Jo kicked him under the table and licked her lips suggestively. Dean kicked her back, harder than he intended because she actually winced. He mouthed her an apology, even though he wasn't really sorry.
"I am so happy you all are my friends." Castiel sighed, sucking back his margarita like it was mother's milk. "I've never had friends like the three of you before. You're so much fun. You're so accepting. No one has ever been so kind to me."
Charlie actually looked like she was about to cry when he said that.
"D'aw, Cas." Dean said affectionately. He reached under the table and squeezed his thigh.
Finally, their dinners arrived and Dean was able to breathe for awhile.
"So Cas, why are you so shy at first?" Charlie said through a mouthful of chicken Fajitas. "I mean, at first it seemed like you were terrified of us. Which there is no reason to be scared of any of us, except for Jo, because Jo is a bitch."
On cue, Jo through an ice cube down her shirt. Charlie squealed. Dean had never felt so at ease.
"New people make me uncomfortable, I guess. I mean, I loosen up, right? I just don't think I make the best impression. Sometimes I think I rub people the wrong way." Castiel said.
"That's weird, though, because you're, like, fucking awesome. Like, literally you're one of the coolest people I've met since I've been here." Charlie said.
Castiel shrugged helplessly, and waved down a waitress.
"I would like to order a round of tequila shots for everyone at this table." He said seriously.
"Sounds good, hon!" The waitress said. She looked directly at Charlie and gave her a huge smile. "Charlotte Bradbury! It's been awhile! How's your daddy doing?"
Charlie, for some reason turned red. "Oh, Bonnie! He's doing great. Retiring next year, actually."
"That's wonderful to hear." Bonnie said. She turned to face the table. "Isn't Charlotte here the best? She used to be so cute. So chubby as a child! You've really bloomed into a beautiful young woman, dear."
Charlie looked horrified and everyone, even Castiel, burst out laughing.
Dean had never been happier.
Bonnie brought them their tequila shots, with a round on the house because she adored Charlie. They did them one after another. Everything was bright and hazy, they were laughing so hard and the four of them were truly perfect. At that moment, Dean was convinced that this happiness was endless. He didn't even care when Castiel kissed him on the mouth in full view of Charlie, Jo and the entire restaurant because he tasted like salt, tequila, sunshine and God, Dean knew at that moment that he could fall in love with him. Charlie and Jo just squealed like old grandmothers and screamed "I KNEW IT!" and they were off to their next bar.
They walked down the main strip of town, still laughing like banshees. The three of them were drunk from the margaritas and tequila shots. Dean glanced over at Castiel, who hadn't stopped smiling the whole night and even though his eyes were unfocused and watery, Dean didn't worry, because he was there to anchor him. Dean knew that nothing could go wrong on a night like this.
The four of them walked into the bar, the only place in town with a dance floor, immediately ordered another round of shots. Charlie and Jo were out there immediately, putting on a show for all of the men in the bar, who just assumed they were drunken college girls trying to get men to buy them drinks, which was about half true.
Dean was drunk enough to sit in a booth located near the back of the bar and make out with Castiel, kind of glad he had a moment alone with him.
"Dean." Castiel breathed, almost moaning. "We should go to the bathroom."
"I don't hook up in public places." Dean whispered. "Just wait until we get back to my place. I promise."
"Why are you such a prude?" Cas breathed into his ear. "I just want to fuck you. I want to fuck you so hard. It's all I've been able to think about for days now. You are such a fucking prude though. What am I the first guy you've ever been with? Come on, let's get out of here."
Dean pulled away. "Cas, I said no. It's only 10:30. We have time." He said a little more sharply this time.
Cas just giggled and nipped at his ear. He drained his beer and stood up to go to the bar. Dean grabbed his hand. Cas turned and looked at him.
"Cas, I think you should chill for a moment. We're all pretty drunk. Come on, come back to me." Dean said, motioning at him.
Castiel hesitated and glanced at the bar. He sighed and sat down. He didn't try to kiss Dean again and didn't say another word about the bathroom or getting out of the bar. He just sat there, staring at Dean with those eyes of his, and Dean felt cold. They didn't say one word for the next few minutes. On cue, by the grace of some higher power, Charlie and Jo came to the booth, red-faced, hair wild.
"We really had them going." Charlie said, laughing. "I love this town."
"In Oregon, it's cool to be gay you know. Especially if you're a hot chick. One reason I never want to leave." Jo said, grinning at Charlie.
"That's actually fairly typical." Castiel said, nodding at Charlie.
"And no one hassled you guys?" Jo asked, semi-seriously. "I saw you going at it."
"Don't worry, Dean put a stop to it." Castiel said, his voice rough.
Jo's eye twitched and she shot a glance at Dean, trying to glean what had caused the change in Castiel's giddy demeanor. Dean and Jo could usually communicate without talking, but this time Dean had no idea what to say to her.
The four of them sat there for awhile, chatting about nothing, Charlie and Jo draining the drinks that two men at the bar had purchased them. Charlie bought Castiel another shot and Dean didn't say anything, because who was he, Castiel's mom? After that, Castiel began drinking freely again, downing two more shots of tequila. After that, Castiel began to get kind of mean, making sarcastic comments about the people around them, pointing out one or two students of his who were in the bar, calling them "absolute fucking morons." Jo and Charlie seemed to notice the change as much as Dean did, because every time a cruel word escaped his lips, he saw them both cringe. Minutes ticked by, and eventually, Castiel quit talking completely and just sat there stiffly, doodling on a napkin and nursing a beer. Finally, Dean reached under the table to try to hold his hand, desperate to make some kind of contact, but he swiped it away. Dean was about to ask him to come outside with him and talk for a minute, but Charlie beat him to it.
"Cas, is something bothering you? You seem like you're not having fun anymore." Charlie said.
"Dean is what's bothering me." Castiel snapped. "Dean and his fucking hypocrisy and teasing."
Dean just blinked. Jo stared at him, clearly still wondering what had happened while she and Charlie were on the dance floor.
"Dude, cool down." Dean said soothingly. "We can talk about this when you've sobered up a bit."
"Did you know that schizophrenia runs in families? Dean, was your father schizophrenic?" Castiel said, seemingly out of nowhere.
"Cas…" Jo said. "Cas, come on. Let's not talk about this here."
Charlie looked concerned, but confused. Dean thanked her silently when she didn't say anything.
"Did you know that people with schizophrenia never recover? It's the AIDS of mental illness. You're basically fucked if you receive that diagnosis." Cas hissed, his voice low and mean. "It's a death sentence." He smiled at Dean and his smile was cold, almost evil.
Dean was blinded with rage and hurt when he said that. He wanted to pummel Castiel, all of the lovey-dovey feelings that he had earlier in the night suddenly draining away. He didn't do anything though. He just sat there.
"Castiel, come on, man. Let's cool it. Let's take a walk. You and me." Jo said, standing up and tugging at his sleeve.
Castiel shoved her, sending Jo toppling to the ground. "Get off me, you fucking dyke!" He growled. "I'm out of here."
"Jo!" Charlie cried, leaping up to help her.
Castiel grabbed his trench coat and stalked out, not looking back once. Dean watched him go. He knew that if he went after him, there was a good chance he'd kill him for what he said about Sam and for shoving Jo. He didn't help Jo though. He just sat there, numb, the world a blur in front of him.