Summary: Based off this prompt: "my friend tried to set me up with her friend but little does she know that i am hella gay and i end up falling in love with her smoking hot brother, and whenever i hang at her place we always tell my sister that it's for a date when really she's now just trying to set me up with her brother" au

Charlie is trying to set up Dean with one of her friends named "Anna", but after one date they know this was their last one. Insert a beautiful blue eyed boy and his sister Anna who loves to play matchmaker and you've got yourself an unexpected turn of events.

Tw: None.

Word count: around 3k

"Okay, what about Anna?"

"Really, Charlie?" Dean sighed, rolling his eyes at his red-haired best friend.

"Yes Dean, she's pretty and actually a nice person. Unlike the last person you dated." Charlie sassed, raising her eyebrows. She knew she was right, and Dean knew it too. That last girl wasn't that great after all, she does have a nice ass though. Dean was known as a huge flirt by the entire student body. But Dean wanted something else, somethingmore than just hook ups. That's how this whole conversation started, Dean should've known better than to tell Charlie. She was like this bloodsucker, she wouldn't let go of this new piece of information. Dean tried to change the subject multiple times, but they were dismissed every single time.

"Okay, fine, which one is it." Dean asked, searching the cafeteria as if she was magically going to pop up.

"That one over there." Charlie said, pointing towards one of the girls sitting with the football team. She had fiery red hair and a nice smile, so why not right? Dean thought, his eyes skimming her body.

"Okay, Charlie, set me up."

****

"Hi! I'm Anna, Charlie's friend." Anna said, smiling up at Dean playing with a string of hair. Dean closed his locker and turned his body towards Anna giving her a flirtatious smirk.

"Hi Anna, I'm Dean."

"Oh, I know, people here talk a lot about you." Anna chuckled, putting a hand on Dean's shoulder. "So how about that date?"

Dean smiled at her forwardness, she was already a lot better than most of the other girls Dean had flings with. "Friday, seven o'clock?"

"Okay!" Anna beamed, her eyes twinkling.

"I'll pick you up. Just text me your address." Dean said, writing his number on a little piece of paper he fished out of his bag.

"I will." Anna winked, before walking off and disappearing in the crowd.

Dean leaned back against his locker, letting his bag fall next to him. There wasn't a spark between them yet, but Dean was going to be patient. Maybe he will feel something during the date. Dean wasn't a big believer in love at first sight. Maybe if he got to know her... Still, for some reason it didn't feel right.

****

Dean parked his car in front of a big white house with a nice veranda. Dean grabbed his phone checking if this was the right house, when he was sure he swung his leg out of the car and made his way to the front door. Dean knocked and took a few steps back, patiently waiting for the door to open.

Dean heard the door knob twisting and the door being pulled open. The person in front of him wasn't Anna. It was a boy with the bluest eyes Dean has ever seen. His eyes were the only thing Dean could focus on, it was like he was under a spell, unable to look away. Dean felt this boy was staring into his soul and it should have made him feel uncomfortable, but really didn't. When Dean finally pulled his eyes away, he inspected the boys' face. His thick eyelashes, his unruly raven black sex hair and his sharp jawline. Dean didn't end there, he continued roaming his eyes over his body. He looked lean, but Dean could see the muscles in his arms moving under his tight shirt.

"Who are you?" The boy asked with a deep gravelly voice that send shivers down Dean's spine. Dean snapped his eyes up, meeting the boys' once again.

"Dean, I'm here to pick up Anna." Dean introduced himself holding his hand out for the boy to take.

"Castiel, I'll call her down." Castiel said, shaking Dean's hand. Dean couldn't help but notice the sparks running up his arm from this single touch. Something he never felt with Anna, or any other girl or boy he dated for that manner. Yes, Dean is Bisexual. But he never told anyone, only his mom knows. He has an amazing bond with his mom, knowing that he can tell her anything and she would still love him the same. Dean knows he would never have that bond with his father, even though his dad loves him Dean is still afraid to tell. He doesn't know how his dad would react to this, what if he throws him out of the house and disowns him. Dean shudders at the thought.

"Anna! Dean is here!" Castiel shouted at the foot of the large white stairs. "Coming!" A voice yelled back. Not long after that someone was running down the stairs, and appearing next to Castiel.

"Ready to go?" Dean asked, smiling down at her. She really was pretty, her long red hair flowing behind her back, her hazel eyes squinting when she smiled. But Dean found himself thinking about those blue ones instead. And he shouldn't because he was on a date with an amazing girl, however Dean knew he didn't have feelings for her. Nothing more than just friendship. And she probably felt the same way, because when Dean parked the car in front of her house again, she turned to him and gave him a kiss on his cheek. "I had fun tonight Dean and you are a really nice guy, but I think what we have will be nothing more than just friends."

Dean felt relieved, he didn't want to tell her. Afraid she might feel something for him, but luckily they were on the same page. "Yeah, I think so too." Dean smiled, placing a hand on her shoulder.

"Besides, you really seemed to like Castiel." Anna smirked, making Dean blush with those seven words.

"Ehm, I-." Dean stammered, staring out of the window to avoid Anna's eyes.

"It's okay, Dean. I have a plan. I am going to try and set you up with my brother. You just have to hang at my place and I will do the rest. Deal?" Anna said, her eyes kind and filled with determination.

"Deal." Dean chuckled, rolling his eyes. This girl sure was something.

"So how was your date?" Charlie asked excitedly, fidgeting in her chair. It was last period, meaning they had math class and their teacher was very strict. Dean didn't have any classes with Charlie earlier that day and he might have avoided her during lunch, so Charlie was probably waiting for this all day. "Later Charlie, I can't afford detention today."

"Why?" Charlie whispered, a teasing tone in her voice. "Because I'm going to Anna's place today." Dean whispered back, smiling and shaking his head when he heard a faint squeal coming from his tiny friend beside him.

He never told Charlie that he's Bi. For some reason he is too scared even though he usually tells Charlie everything. They have been best friends since they were little, when Charlie punched a kid for making fun of Dean they instantly hit it off. Their parents used to joke, saying they will end up with each other in the end. But both Dean and Charlie know they will never feel that way about each other. Dean knows he has to tell her one day, but he isn't going to makethat day today.

Charlie immediately spoke again one they were dismissed from class. "So you two hit it off, huh?"

"Yeah, we did." Dean replied awkwardly, scratching the back of his neck. He loved Charlie dearly, but he really wished she would go away now.

"Well, have fun tonight. I've got to go, the new episode of Game of Thrones came out today and I can't wait to watch it! But you do have to tell me the details tomorrow." Charlie smiled and finished with a serious, "I'm counting on it".

Dean sighed in relief and walked outside, already spotting the beautiful black '67 Chevy Impala glistering in the sun. Dean smiled faintly at the memory of getting the keys to the car for his 16th birthday, immediately taking her for a right as he already got his driver's license the week before.

Dean got in quickly and drove to Anna's house. As he almost reached Anna's house, the nerves suddenly twirling inside of him. He didn't even know Castiel personally, just his face and his name. Maybe Cas wasn't even playing for that team, but why would Anna set them up if he didn't. This stilled his stomach just the slightest bit, however, not nearly enough. He was already sweating when he stepped out of the car and knocked on the door for the second time in 24 hours.

"Come in Dean." Anna greeted Dean happily, giving him a small hug when he stepped into the hall. "Don't be nervous, it'll be alright." Anna whispered. Dean tried to relax, although not seemed to help. Anna grabbed his hand and squeezed it in reassurance as they walked down the hall and went through a large white door. The room behind the door was huge, with comfy looking couches, a flat screen and a fireplace. This presumed living room was cozy and felt homey, especially when Dean spotted the baby pictures on the shelf above the fireplace. Dean stepped forward to take a closer look, but the door of the kitchen swung open, revealing a surprised boy with stunning blue eyes Dean instantly recognized as Castiel in the doorway.

"Hey Cas."

"Hello Dean." Castiel answered with a confused head tilt Dean found endearing. "I didn't know Anna was having you over, apologies."

"For what?" Dean asked, he was confused now instead of Cas, who was starting to look a bit flustered now.

Castiel averted his eyes from Dean and focused on the ground instead, a small blush grazing his cheeks. Dean gave Castiel a one over and noticed the clothes he was wearing. A tight fitting T-shirt with sweatpants who hung dangerously low on his hips, which should have been illegal. Dean couldn't stop himself from staring at the boys' body now, getting quite flustered himself. When Dean could finally tear his eyes away, he found Anna on the other side of the room, smirking at him of all things. Dean stuck out his tongue and focused back on Castiel who still refused to meet his gaze; instead he inspected the walls, the TV, even the family photos but never Dean.

Dean cleared his throat and instantly those big blues where back on him. "It's okay Cas, really." Dean smiled, trying to look reassuring or comforting, not knowing if he was doing a good job at it. Castiel gave him a small smile back, tension flowing out of his muscles and Dean was relieved to see that it actually worked.

"So how about a movie?" Anna asked, breaking the staring contest that was still going on.

"Sure, sounds like fun. Cas?"

"Oh, I apologize, I will be upstairs in my room." Castiel said with a quick nod, almost darting out of the room. Luckily, Dean was standing close enough to grab his arm and spin him around. Of course Castiel lost his footing and slammed against Dean's chest. Dean wound an arm around his waist, holding Castiel firmly against him. "Stay." Dean said, no hesitation in his voice. The message was loud and clear and Castiel couldn't help but nod.

Dean carefully helped Castiel to stand on his own again before sitting next to Anna, who was already searching Netflix for a movie to watch.

"How about this one?" Anna asked finally settling on a movie. Dean was pleased to see she had chosen a Batman movie.

"Sure, I could do with some Batman. How about you Cas?" Dean asked, turning his head so he could look at the smaller boy beside him. Castiel looked like he was in his own little world, just staring at nothing with a distant expression. "Cas?" Dean asked again, startling the boy who now wore a deep scarlet color on his cheeks, spreading to his neck. "Y-yeah, sure." He answered, focusing on the screen. Dean smiled at the adorable boy next to him and focused on the screen as well.

They weren't even 15 minutes into the movie before Anna sprung up, her phone in her hand stating she had to go to Charlie's house because of a fandom emergency. Apparently something happened in this week's episode of Game of Thrones and Anna had to go there immediately. After asking if it was okay to leave, she bolted out of the house, leaving Dean and Castiel in an awkward silence. They continued watching the movie, but the (sexual) tension could be cut with a knife. Dean couldn't help but stare at Cas and Cas himself was trying to focus on the screen but failing miserably. Somehow they ended up staring at each other, roaming their eyes over each other's faces, bodies, involuntary scooting closer. There were close, way too close, Dean could feel Castiel's breath fanning over his face. This was too much, he didn't have enough self-control to back away, and it was too late now.

Dean captured Castiel lips in a sweet kiss, one that only lasted a second, before moving away. Cas wore a shocked expression on his face, but no hint of disgust. Suddenly Castiel's lips were on his again instantly deepening the kiss. Their lips passionately moved against each other and it wasn't long before tongue and teeth were involved. The only thing that Dean could think were "Cas" and "more", so Dean moved his hands to the hem of Castiel's shirt, spreading his fingers under his shirt and up his chest. Castiel moved away from the kiss and ripped his shirt from his body in one fluid motion. As soon as the clothing article was removed, Dean mouthed Cas's neck, nipping at the skin. Without moving his lips off Cas's neck, Dean carefully pushed him down, crawling on top of him. Dean's lips moved to the spot between Castiel's neck and shoulder, sucking and biting the tanned skin, leaving little red marks all over his neck and collarbones.

"Dean wait-." Castiel said, out of breath with a panicked look in his eyes. Cas pushed at Dean's chest, but Dean was already moving away looking down at him worriedly.

"Shit Cas, I'm sorry. Did I do something wrong?" Dean asked, panicking as well. He could not lose Cas, not when he never actually had him.

"Yes, No, I don't-."

"Talk to me Cas, please." Dean begged, his eyes pained.

"What about Anna?" Castiel asked, his eyes a mix of horror from his supposed betrayal and sadness looking the other way, thinking this was a mistake and Dean was going to pick Anna anyway.

"Cas, please look at me." Dean whispered, gently taking Castiel's chin in his hand and forcing him to look in Dean's eyes. "Anna and I aren't and will never be together. Yes, she is a great girl, but I don't feel anything for her and she doesn't feel anything for me. I was a player but after a while I was done with the mindless hook ups. I want a relationship. Especially one where I can feel a spark, this ineffable attraction. And I feel that way about you Cas, that's why Anna was playing matchmaker and trying to set us up together. I like you Cas I want to get to know you."

"I would like to get to know you too Dean." Castiel said, smiling softly, then giving Dean one last lingering kiss before moving away.

"How about a date?" Dean asked, winking at Castiel smiling when he saw the boy flustered again. Castiel nodded excitedly and threw himself into Dean's arms hugging him tightly.

****

To say that the date went well was an understatement and both of the boys were happily together now. Dean felt a bit bitter knowing Castiel went to a different school than him, but was determined to spend every free second with his new boyfriend. But before everything, he had to tell Charlie; he can't keep it a secret from her any longer.

"Hey Charlie, can we talk, maybe?" Dean asked, suddenly very unsure of himself. Charlie wasn't going to hate him, right?

"Of course Dean, are you okay." Charlie asked, concern written all over her face. Dean nodded, not trusting his voice right now and lead them outside to the bleacher behind the school. It was a beautiful day, the sun was shining brightly and the grass seemed greener than usual.

"I have to tell you something..." Dean began, but trailed off inspecting Charlie's eyes, but found nothing else than concern and a sisterly kind of love.

"You know you can tell me anything right." Charlie said, gently placing a hand on Dean's shoulder, giving him one of her soft smiles that always made Dean feel at ease whatever the situation.

"Okay, here we go." Dean sighed before letting the word flow bursting out of his mouth. "I'm Bi and I've known for a while and nobody knows except my mom and Anna and Cas now as well. I wanted to tell you, but I was too scared to lose our friendship and I'm so sorry, you can leave if you want to, I mean I get it if you don't want to be friends anymore and-." Charlie cut Dean off with a big hug, giggling in his chest.

"What's so funny?"

"I'm gay Dean." Charlie explained, continuing before Dean could utter a word, "I was too scared to tell you too."

"We are a bunch of idiots." Dean laughed, playfully hitting Charlie's shoulder.

"Yes, we are. Now, tell me all of the details! And don't you dare leave something out."