Disclaimer: I do not own Dean Winchester, Sam Winchester, the Impala, or any other characters you might recognize.

Dresses, Dreams, and Dean

Holly Black. A simple, pretty name. Yeah, sure. I think my mom and I are the only ones who think I don't sound like a peasant. I do fit the profile though. I'm what you call a Plain-Jane. I wear simple clothes, modest, obviously, since I'm a klutz and the last thing I would need would to trip over my feet in heels or split my mini-skirt bending over. So, I stick to pants and long skirts and simple tops. And my black hair was always either in a ponytail or let down, where it tumbled rather prettily onto my shoulders. I knew that I could have been popular just by my looks if I ever tried, but I'd never had a reason to.

That is, until he showed up. It was the end of the school year, with just three weeks left. It was Wednesday and prom was the next weekend. I hadn't been asked, but I never had before, so my best friend, Nicole, and I were going together. We were seniors, so it really didn't matter to us if we had dates; just as long as we could go. Prom is a very special thing for a teenage girl. Anyway, it was an easy day, like the end of school always was.

Nicole and I were chatting with each other in Homeroom and everyone else was talking and laughing and throwing bits of paper around with notes written on them. Mr. Billingsly was sitting at his desk, a smile on his middle-aged face as he watched us all enjoying our last few weeks of school. He had a deck of cards and was playing, what I guessed was, a solitaire game when he walked in.

It was like a movie. Everyone in the room fell silent the moment the door closed with a small bang. The girls were just eating him up with their eyes and I was sure the guys were feeling their egos punctured and jealous rising as his green eyes glanced around the room, stopping on each and every girl there. Including me, but he didn't linger on my bland form for more than a second. I couldn't help but get chills that made their way from my scalp all the way to my toes, tingling the whole way.

Mr. Billingsly stood and looked at the note he handed him. "Alright. Class, this is Dean Winchester."

Dean Winchester. God, even his name was sexy as hell. My eyebrows shot up under my bangs at the thought. I never had thoughts like that. I almost blushed, but stopped myself, only to find myself holding my breath as he walked closer--I swear, in slow motion--and slipped into the desk in front of me. I couldn't help but finally breath in. He smelled like old leather--probably from the jacket he was wearing--and something else. Sharp, oily almost....gunpowder? My father had a gun at home and I knew the smell, but I could have been wrong.

He, Dean, settled right into the senior class. Everyone went back to whatever they were doing before. Nicole and I were both gawking at him, while the other girls around him were vying for his attention. I couldn't blame them. And if I were a different person and hadn't been wearing my most unflattering floor length skirt that day, I would have been chatting him up too. But instead, I had to live off of simply watching him, mesmorized by even the slightest of motions.

The rest of the day, whispers of Dean Winchester floated through the halls and more importantly, the girl's bathroom. I lingered in a corner by the window and sinks just to hear what the girls who actually talked to him had to say. Stacy Whipple told everyone he'd invited her to the janitor's closet during lunch. Every girl in the room--including me--felt a pang of jealousy. And Stacy never lied. Ever.

Nicole and I talked over the phone for a good five hours that night. Luckily we didn't have any homework, otherwise it wouldn't have gotten done. We both gushed over every second we'd seen him that day. In other classes, during free period, in the halls. Nicole had seen him leave the school with his little brother. I squealed over the thought of him having a little brother. Just the idea was adorable. The fact that he'd actually waited to walk home with his brother was something. Mostly if you had a sibling in this school that was younger than you, everyone else wouldn't know you were related if it wasn't for your last name.

Thursday and Friday went the same way for Nicole and I. Dean sauntered into Homeroom later than everyone else and I could swear that he looked at my both times. I did my best to pick out my best clothes those two days. I had nothing flashy or that showed any skin minus my arms, but I did my best. Even Nicole took a chance and wore the shortest shorts she was able to wear in school on Friday. During lunch, she pulled me into the bathroom and told her story through squeals: that Dean had talked to her for a full thirty seconds. Of course, then Linda Ferrel had come by in a low cut top and her boobs nearly falling out of her shirt and he got distracted. Poor Nicole; she was flat chested as a little boy, but she had great legs, hence the thirty second conversation.

That night, Nicole spent the night. Mom made us chocolate fondue and we dipped in anything we could find from strawberries and bananas to potato chips and sugar cookies. We spent most of the night gushing over Dean Winchester and laying out on my bed on our stomachs, stuffing ourselves with chocolate dipped goodness and flipping through prom dress magazines. We were both going out to buy dresses the following morning as early as we could. We should have gone sooner, I know, but we were procrastinators and so we decided to buy dresses a week before prom. Call us insane.

We fell asleep about one in the morning and woke up at seven. Mom left for work just as we stumbled down the stairs. She left me money on the counter for my dress before reminding me to have some fruit with breakfast and then she was off.

"Know what I wish?" Nicole asked as she slipped her skinny self onto the counter next to the sink.

I leaned against the island in the middle of the kitchen and looked up from the magazine Mom had left open. "No, what?"

"There were enough Dean's for all of us," she finished with a dreamy sigh.

I sighed right along with her. "That would be Heaven. Imagine...one of him for every girl in school...and and, one of him that liked everything about every girl. You know?"

She nodded, red hair falling into her face. "Oh totally, Holly. I mean, the guy is gorgeous and obviously a good kisser because Stacy won't shut up about her closet rendevouz, but how come he's never spoken to you? You're one of the prettiest girls in school!"

I rolled my eyes. "Riiiight. I think it has to do with how I dress. I'm like a nun." I stood and let my hands fall to my sides, palms slapping against thighs. Even my pajamas were modest. A ripped t-shirt and apartment pants.

Nicole hopped off the counter and opened the fridge, peering inside. "Well, that's what you get for dressing like that! Why don't you ever show some skin? You're stunning and if Dean could see that...oh damn, I bet he wouldn't even look at the other girls again." She stood up and winked at me.

"Stop getting my hopes up," I mumbled, walking around the island to pull a banana off from the bunch.

"What's that mean? You're going to get all sexy come Monday?" she squeaked, nearly jumping up and down.

"Whoa-ho." I held up my hands, palm out, which was rather hard since my left hand was holding fruit. "I didn't say that. Because you know I don't even own a bathing suit for that reason. I don't like showing...skin." I bit off the top of he banana.

It was Nicole's turn to roll her eyes. "You, girlie, have to get over that. You should have been kissed by now and you would be if you weren't so freakin' self-doubting."

I sighed and thought for a moment. "Alright. Here's the deal...I'll let you pick out my prom dress and do everything to me prom night." Her eyes widened and she gave a mischievous chuckle. I realized what my words sounded like and blushed. "Not that! I mean, hair and make-up and teaching me to be the...belle of the ball. Got it?"

"Got it," she replied, with humor still on her voice.

x-x-x-x-x-x-x

"I can't believe this was my idea." I was hiding in my bathroom. It was Saturday. Prom day. Nicole and I had both found dresses a week earlier. Well, more correctly, Nicole had found our dresses. I hadn't thought much of the dress when I'd first put it up, but after a week of soaking in Dean-filled thoughts and thinking of how I supposed to wow him come prom, I was suddenly hating my deal.

"Come on, Holls! I bet you look gorgeous. And I still have to do your make-up and hair so get your ass out here!" Nicole exclaimed through the door.

I took three deep breaths and nodded to myself. I reached out a hand and pulled open the door. Nicole's eyes bugged out of her head and her hand slapped againt her face as her palm covered her mouth. "What?" I asked panicky, holding my arms out to my sides.

"Oh my GOD!" she squealed, jumping up and down and clapping her hands. "You. Look. Amazing! More than amazing. Simply drop dead gorgeous!" She giggled and clapped her hands again.

I took a breath and looked down at the dress. It was stunning in itself. A pretty teal-green color, it was skin tight. Low cut on the top with a swooping back, one thin strap on the left side kept it up while the other side was kept up with a sleeve that was tight down to my elbow and then flowed out for four inches. The dress hugged curves in my waist I didn't know I had and flowed out from about half-way down my thigh to form a night, flowing skirt part. And surprisingly, I could even walk in it.

"You think so?" I asked sheepishly, running my hands over the shimery material.

"Absolutely," Nicole replied with vigourous nodding. "Now, since you helped with me earlier, it's your turn." She put her hands on my shoulders and went right back into the bathroom. She forced me to sit down on the toilet seat and pulled out a bunch of makeup to put on the counter. "Know what? Take the dress off, I don't want to ruin it."

"What?!" I squeaked.

"Take the dress off. I know you're wearing a bra and panties girlie," Nicole said with chuckle.

"Ex-ney on the bra-ney. Did you see the back of the dress?" I stood and showed the back of the dress, or rather, the lack of one.

"Oh right. Forgot. Well, go put on a robe and I'll get started."

I complied. The dress was set ever so carefully next to Nicole's on the bed. She was wearing my mom's robe. I snatched mine out of my closet and then went to allow my best friend to make me the stunner she said I was.

Halfway through, when my makeup was done and she was working on my hair, a chilling thought reached my head and my heart dropped two inches in my chest. "Oh my god," I whispered.

"What?" Nicole asked, catching my tone. She looked at my intently in the mirror. She was standing on a little stool behind me so she could work. "Hol, what's wrong?"

"What if he's not there?" I breathed out, clutching the edge of the sink.

"Oh hun!" She let the hair in her hand drop and hugged me around the shoulders from behind. "He'll be there. Think he'll miss a chance to pick from a whole room of pretty girls in dresses for someone to go back to his car or hotel room and do it? Come on, he's a guy!"

I frowned. "That didn't come out very comforting," I told her matter-of-factly.

Nicole waved a hand in the air and went back to my hair. "He'll be there."

It was almost time to leave by the time both of us finally slipped into our dresses. My black hair had been curled even more than it naturally was and set into a messy, yet pretty tangled bun with a few pieces of hair framing my face and a few waves covering the back of my neck. The shoes, thankfully, weren't very tall and I could walk in those too. Nicole was a genious. And she was gorgeous in her own way too. Her dress was a pretty yellow, starch contrast with mine, but it worked nicely with her red hair and fair skin. Not that I wasn't white as paper, making my dress and hair stick out more, feeling like I was overshadowing her.

We got downstairs and Mom went beserk, talking photos of us like she would have if I had a date. We managed to escape the constant snapping of photos and hurried out to Nicole's little red sports car. She drove, while my heart attacked my ribcage. I felt like I was going to throw up, especially when I saw the school and all the people in dresses walking around. Not to mention guy's in suits and tuxs and anything that could pass for formal.

Nicole pulled into a parking spot and shut off the engine. "I don't think I can do this," I managed to get out, gripping the handle on the door.

She let out a breath and turned me towards her, putting her hands on my shoulders. "You'll be fine! You're gorgeous and you will own this night, babe! It'll be a night to remember from your high school days."

I nodded and took a deep breath. "You're right," I said, nodding. I said it a few more times before a smile appeared on my face. "Come on," I said, excitement filling my voice as I swung open the door and stood up all in one motion. At that same time, there was a slight screeching of brakes and when I saw what car had almost hit me and the car door, my heart stopped. It was black, shiny and otherwise old. And who was behind the wheel other than him, Dean Winchester. Our eyes met--corny I know, but it's true--for a few seconds that seemed like hours and then he half-smiled and raised an eyebrow, eyes scanning down to the door. Realizing what he meant, I blushed and shut the door quickly, glancing at Nicole across the roof of the car and taking a few steps backwards to the grass by the front of the car.

Feeling powerful and not at all like my usual self, I gave Nicole a smile and she nodded, walking to the school by her lonesome, leaving me standing by the front of Dean's car as he parked. My legs felt like jelly, but I stayed standing with--what I hoped was--a coy smile on my face as my hands clutched at the sheer shawl that drapped down my back and was coiled around my arms. My heart was once again thumping against my chest as he got slowly out of the car--damn slow motion hotness again--and closed the door behind him.

He took a few steps around the front fender, hands sliding into the pockets of his pants. "Hey, do I know you?" he asked and my heart skipped a beat. He was actually, posatively talking to me! ME! Miss peasant, Plain-Jane, Holly Black! I could hardly believe it. I owed Nicole big time.

"Uh sort of," I replied. "I'm Holly. You sit in front of me in Homeroom."

His eyebrows rose and for the first time in my life--I have to admit it--I got checked out. Harsh words that don't even seen right to put with Dean, but it's true. He lookd me up and down and I didn't even blush or anything. It was nice to finally be seen. "Wow." The word seemed to slip out from his lips but he composed himself. "You know, I was just going to crash the party and ditch, but since you're looking so nice, want me to take you in and show you off?"

I couldn't hardly process the words. I nodded and he grinned--I swear it--and came up beside me, holding out his arm like he'd probably seen in the movies. I let a smile fall on my face and slipped a hand through the crook of his elbow and we started towards the school.

I felt like a goddess or princess or something, floating more than walking. I'd never been seen as dating material by anyone but the school geeks and I'd never had a whole room look at me--although mostly with jealously from the girls and a strange look from the guys--and I could care less. This was more than just about Dean, although, that had a hell of a lot to do with it, but I was being seen for the first time in my life. I was young and beautiful and I sure as hell was flaunting it.

Not to mention the guy I came in with was a total stud and I didn't even care if he forgot about me the next day. It was prom, the biggest night--pretty much--in a high school girl's life. And I, Holly Black, was now the envy of the school.