Set Up (Team Free Will x fem!reader x Gabriel) High school AU

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"Come on, Y/N. You'll love him," your best friend begged. You rolled your eyes. "No, Dean and I really wish you would stop," you told him with a laugh. Groaning, Dean turned his attention back to the try in front of him. "Hey, guys," Sam greeted as he came and sat down next to you. You smiled at him. Sam was a freshman while you, Dean and your other best friend, Castiel, were all seniors. "Hey, Sammy. How's it going?"

"Fine. So, did Dean talk to you?" You sighed. "Come on, guys. Why is this so important to you?" Dean shrugged, his mouth full of food. "Perhaps because it's almost the end of senior year and you haven't had a boyfriend all year? Or girlfriend. We just want you to be happy, Y/N," Castiel said as he took his seat next to Dean. He rolled his eyes as Dean stuffed his mouth full yet again.

"I am happy, guys. Besides, how do you know I don't already have a boyfriend or girlfriend?" Dean arched a brow. "Do you?" You winked and replied, "That's for me to know and you to find out." The three young men scoffed almost in unison. "You don't." You smirked. "How do you know?" Without waiting for an answer, you got up and left the cafeteria.

Ever since the end of last school year, your best friends had been trying to set you up on dates every other weekend. You appreciated their concern, but it was really getting annoying. You let out a huff before you heard a familiar voice, "Hey there, Sweetcheeks." You couldn't help but smile. "Gabe!" you cried, throwing your arms around him. Gabriel was a 2nd year college student so you didn't get to see him that often.

"I missed you," you said, your words muffled by his shoulder. "I missed you too, Sugar. Now, how about I take you out tonight? I'm in town for a few days for the upcoming holiday and I would love to spend time with my girl." You giggled and nodded. "I'd like that." Gabriel smiled and kissed you. You and Gabriel had gotten together in the middle of the summer, but you hadn't told anyone. You weren't sure your parents would approve since he was a few years older than you AND he was Castiel's older brother. A big no-no.

"What do ya say to skipping the rest of the day?" Laughing, you shook your head. "I can't, Gabe. I have a paper to turn in. But, after school, I'm all yours." Gabriel gave you a wink. "Alright, Sugar. I'll see you then." He gave you another sweet peck before he turned and left. Smiling to yourself, you went off to your locker before your next class began. For the rest of the day, you could hardly focus on your classes. You just wanted the final bell to hurry up and ring so you could escape.

You almost sighed in relief when the bell did finally ring. You gathered your books and hurried to your locker. You knew you had to be quick or Dean and the others would stop you from leaving by trying to set you up with someone else. You made your way outside as fast as you could. It didn't take you long to spot Gabriel and you smiled. He opened his arms as soon as he saw you and you ran to him. You threw your bags in his car before turning and planting a firm kiss on his lips.

"Whoa! Whoa! Wait a minute!" Dean's voice cut through your little bubble of happiness. You turned to see your best friends all standing there with their mouths hanging open. "How long has this been going on?" Sam asked. Gabriel kept his arm wrapped around you. "You didn't tell them yet?" You shook your head. "I thought we agreed not to until after graduation." Gabriel gave you a smile and kissed your forehead. "Y/N and I got together this summer. We knew her parents wouldn't approve so we kept it hush-hush. Not to mention little brother over there looks like he's about to blow a gasket."

It was true. Castiel's blue eyes were full of hurt and his face was red. "I'm only angry you didn't tell us. I thought we were your best friends and Gabriel, I'm your brother. It's not like I would have told Dad." You smiled. "It's not your dad I'm worried about, Cas. Chuck likes me. It was my parents." The boys finally closed their mouths and nodded. "Okay," Dean started, "Well...as long as you guys are happy, I guess I'm cool." Sam and Castiel agreed.

"Glad that's settled. Now come on, I'll give you guys a ride. I know Dean's precious Impala is in the shop...again." Dean frowned. "No thanks. I don't want to be witness to your chick-flick moments. I'm glad my best friend is happy, but I don't need to see just how happy." Dean shuddered, making everyone else laugh. "Fine. Take my truck." You tossed Dean your keys. He grinned and ran off, Sam and Castiel following. "Don't wreck my boy!" you called before turning back to Gabriel. "Took them long enough. Now come here and give me some sugar, Sugar."


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