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Prom is the one thing you were looking forward to ever since freshman year started. You waited 3 years to go to Prom and you were going to have a good time. You got yourself a date with one of the football players. You were shocked that he asked you out since you never really talked to him. You’ve been to his games because you loved football and you had classes with him but you never really talked.
You were surprised he knew who you were. But you didn’t turn him down. You were so excited to go to Prom, you heard it was going to be at an actual castle this year. You and your best friend had a ton of fun picking out your dress. His brother even came along which you didn’t mind. You actually had a small crush on Dean Winchester. You never told Sam this because you were still in high school and Dean graduated 4 years ago so it would be weird to go out with him.
Plus, he doesn’t like you either. Why would he like some 18-year-old senior? Nonetheless, you had tons of fun with the brothers. They both knew how excited you were about this event coming up.
The theme was a masquerade ball and you found the perfect dress for the occasion.
You also found a beautiful lace mask that covered just the right amount of skin.
You couldn’t have been happier with your choices and now, all you had to do was wait.
You’ve done enough waiting and today was finally the day. Prom started at 8 pm and you got up at 7 am so you had enough time to get everything ready. You had asked Jessica if she would come with you to get your nails and hair done. She was more than happy to oblige. Your nails finished fairly quickly so now, all that was left was hair. You would be doing your makeup at your house after you finished at the salon.
“You excited?” Jessica asked and you smiled.
“Yes, I am. I can’t believe Zach asked me to go with him. I mean, I barely talked with the guy.”
“Hey, don’t sell yourself short. You’re gorgeous.” She smiled.
“Thanks. Sam must be super happy to be going with you. You know, he’s probably going to kill me for saying this but he really likes you and when you said yes, he was so happy.” You smiled.
“I’ve actually had a crush on him for a while now. He’s smart and nice and just a good man. I did well.” She giggled. The rest of the appointment went by smoothly and before you knew it, you were back at home, doing your makeup. It was getting closer to 8 and you knew Zach would be here any minute to pick you up to go to dinner beforehand. He said he would pick you up at around 5:30 and it was already 5:00.
When you were almost finished with your makeup, your phone buzzed, letting you know you got a text message. You looked at it, not expecting anything to be wrong.
Hey, sorry but I have to cancel tonight. Stacy Bingham just texted me. I’ll be going to the prom with her. You understand, right?
You had to read the message twice before you let the realization that you were dumped sink in. You got tears and normally, you would keep them in because it would ruin your makeup but now, you didn’t find it in you to care. You were just dumped on the day of Prom, something you were looking forward to since the beginning of high school. But Zach just decided to toss you to the side like trash without thinking what it was doing to you. You didn’t even know how to respond to him.
Fuck you.
You didn’t know what else to say but that was the only thing you managed to type before you started crying. You threw your makeup to the side before getting up. You passed by your dress and shoes, going over to your computer before turning it on. You needed to talk to Sam about this, letting him know you wouldn’t be going.
You decided to video chat him and luckily he answered. It meant that he hasn’t left to dinner yet.
“Hey! How’s it go–what’s wrong?” Sam answered, seeing the look on your face. He was all dressed up and fixing his cuffs but he stopped that when he saw your tears.
“Zach dumped me. Said he’s going to the Prom with Stacy instead.” You let more tears fall, not hiding how much this hurt you.
“Oh, Y/N, I’m so sorry. Why would he do that?” Sam sighed.
“Because I’m trash?” You looked down.
“Don’t say that. You’re not. Look, I’ll call Jessica and tell her to go without me. You shouldn’t be alone right now.” Sam said but you stopped him.
“No, you don’t know how excited she was earlier. Ditching her for me would be a bad move, Winchester.” You sniffled.
“But so were you. You were so excited.” Sam sighed.
“Yeah, I was. Look, I didn’t call you for a pity party. Just go without me, okay? I would love to hear all about it at school on Monday.” You were going to hang up but he stopped you.
“Wait, why don’t you come with me and Jessica? You can still have a good time.”
“I don’t want to be a third wheel to you guys. Me being there without a date would just hold you two back from having a good time. Plus, I wouldn’t have anyone to dance with. Won’t be much fun if I’m not dancing. Zach would be there with Stacy and I know she would have a great time rubbing it in my face that she’s with Zach. Don’t worry about me. Have fun.” You hung up after that and sighed, leaning back in your chair. You were so sad because Prom was supposed to the highlight of high school. A night of many memories you would remember forever.
Now you won’t get that.
You got up and walked to your bathroom before wiping your makeup off your face. After you finished, you looked at your beautiful dress and the mask hanging from the hanger. You sighed and changed out of your slip you would have worn under your dress into pajamas. You passed by your mirror and paused, looking at your hair. The stylist did a wonderful job but it was a waste of money. But you didn’t have the heart to ruin the beautiful work she did.
Deciding to leave it the way it was, you walked out of your room and to the living room to watch some reruns of your favorite show. You took a seat on the couch and sighed as you turned on the TV. You couldn’t believe this was happening to you.
You were so stupid to think that you could have this night. You were stupid for thinking Zach really wanted you. You had no idea why he wanted you in the first place but you should have known better. Guys like Zach didn’t ask girls like you out for no reason. You didn’t know what you would do on Monday morning when you saw his face.
What he did to you was cruel and it would always stay with you that he stole your prom from you.
You looked at the time and sighed when an hour had passed. Prom was in one hour but you didn’t care. You were about to start another episode when you heard your doorbell ring. Your parents were out of town, leaving you alone in the house. You had no idea who was at the door but you got up anyways and walked to it.
The bad thing about your front door, it didn’t have a peephole so you literally had no idea who could be on the other side. You took a deep breath and opened it but froze when you saw who it was.
“Dean…” You whispered, looking at the beautiful man in front of you. He was dressed up in a tuxedo, holding a corsage container that was meant for you.
“Hi. Y/N.” He smiled.
“What are you doing here?” You asked, having an idea but needing him to say it.
“I heard you were short a prom date. I hope I’m not too late.”
“I don’t need a pity date, Dean.” You started to say but he cut you off.
“This isn’t a pity date. You know, if I were your age, you would be the first person I’d ask to Prom.” He said truthfully. He’s always had a crush on his brother’s best friend. But he never thought you would like someone as old as he was. He was only 4 years older than you but still. He was in college and you were still in high school. He was going to wait until you graduated to ask you out but it was now or never.
“Really?” You asked with a smile.
“Really.” He winked at you. You blushed and bit your lip before opening the door wider.
“Come in.” You said and he smiled at you before walking inside.
“You know, if you get dressed now, we can make it and be fashionably late.”
“Are you really serious about this? You’d take me to Prom?” You asked with a smile.
“I would. I am if you’ll say yes?” You stared at his face, trying to find some sign that he was joking but when you didn’t find one, you smiled widely.
“I’ll go get dressed.” You smiled and felt 100% better about the outcome of your night. You left Dean’s side and walked to your room where you began to get ready. Because you didn’t have enough time, you only put on light makeup. You had a feeling Dean loved women without makeup so that is why you only put on a light layer. You put the slip back on and slipped on your dress. You smiled and looked at yourself in the mirror before slipping on your shoes. You couldn’t believe you were going to the Prom with Dean Winchester. You wondered if Sam had something to do with this but you didn’t care. You were going with Dean and that is all that mattered.
You grabbed your mask but didn’t slip it on. When you were completely ready, you walked out of your room and to the stairs.
“I’m ready.” You said and walked down the stairs. Dean looked away from the TV and to you. His mouth went dry as he watched you descend the stairs. He knew you picked this dress out but he didn’t get to see what it looked like on you. You were breathtakingly stunning and he was lucky to take you to the Prom.
When you got to the bottom, you looked at Dean, swiping some hair that fell in front of your eyes.
“Well? Do I look silly?” You asked and he walked closer to you with wide eyes.
“You look gorgeous, simply stunning.” He said truthfully. You blushed deeply and he took your right hand before slipping on the corsage he got you. It matched your dress, he made sure of that.
“Thank you.” You smiled and he held his arm out for you to take.
“We should get going.” You nodded and took his arm. He led you to his sleek black car, opening the passenger door for you. You blushed and got in, getting comfortable. He got behind the wheel and before you knew it, he was pulling away from your house and arriving at the Prom.
After finding a parking space, he opened your door after he got out and helped you out. You smiled and held out your mask to him.
“You mind?” You asked and he nodded before grabbing it. You turned around and he placed the mask over your eyes, tying it in the back.
“Does that feel okay?” He asked and you nodded, turning back around.
“Do you have a mask?” You asked and he nodded as he reached into his car before pulling out a plain black mask. He quickly put it on before placing your hand in the crook of his arm.
“We’re going to have a great time.” He said as he walked to the entrance. When you got in, the place was booming with music. You grinned and looked around at the beautiful decorations. You looked at people dancing, having a great time before you spotted Sam and Jessica by the punch.
“I see Sam.” You smiled and walked over to the couple.
“Hey! You made it!” Sam said when he saw you. You nodded and looked at Dean who looked at his brother.
“Dean saved me.” You said and Sam nodded, looking at his brother.
“Is that so? Dean, a word?” Sam said and walked off with his brother. You sighed and looked at Jessica with a smile.
“I heard what happened. I’m so sorry. Zach is an asshole who doesn’t deserve you.”
“Actually, I’m kind of glad he did. I’m here with Dean.” You blushed and he giggled.
“Y/N, you’re here,” You heard the devil say. You turned around and saw Zach standing there with Stacy on his arm.
“Sorry, but Zach liked me better,” Stacy said with a smirk. You glared at her but before you could say anything, you felt hands on your shoulders.
“Y/N, want to dance?” You looked up to see Dean standing there behind you.
“Sure.” You smiled but Zach stopped you.
“Who is this guy?”
“Yeah, I’ve never seen him before,” Stacy added. Dean took off his mask and placed it on the table.
“Dean Winchester and you’re right, I graduated. Come on, Y/N.” He said, pulling you away from the couple. A slow song began playing which seemed like perfect timing. You grinned and wrapped your arm around his neck before taking his hand with your other hand.
“You know, you didn’t have to do this.”
“That guy’s an asshole. You deserve better than him. He’s not a real man.”
“How did you know? About what happened?” You asked as you danced with him.
“I overheard your call with Sammy. No woman deserves what happened to you. I’m actually kind of glad he dumped you. I wouldn’t be here with you if he hadn’t.” Dean confessed.
“I said the same thing.” You smiled, looking into his eyes. He pulled you closer to him, leaning down as he continued to dance with you. You stared into his eyes as he got closer to you. You knew he was going to kiss you and you were okay with that.
You met him halfway and placed your lips on his. He smiled in the kiss but kept it light before he pulled away. You smiled and placed your head on his chest, moving your other hand to meet yours behind his neck. He placed his other hand on your waist and danced with you.
Dean Winchester was a perfect gentleman that night. After that, you stayed with him even when you left for college. You would always remember the night Dean Winchester became something much more than a prom date.