Disclaimer: I do not own Supernatural or it's characters. Nor do I own the song 'This is My Idea' from Swan Princess - from which this story is based.
Author's Note: I know, I'm a bit cracked out sometimes. But if Bobby Singer had a daughter, I think this is a plausible scenario.
The only point on which they didn't disagree
Was that summertime was dreaded
I. If I Get Lucky I'll Get Chicken Pox.
For as long as Dean Winchester could remember, he had spent parts of every summer at the Singer Salvage yard with his younger brother, Sammy. He was only six when his Dad started taking him there, and for as long as he could remember Bobby - owner of the Singer Salvage Yard - and John would tell him that one day he and Ashton Singer would wed. Quite honestly, Dean always thought they were both insane. Ashton wasn't exactly hunter material - she liked romantic, silly things like art and music. When Dean arrived at the Singer household Ashton was infallibly drawing something; though the particular something changed from year to year. She went through periods of morbidity, cartoons, and realistic portraits. Once she attempted to draw Dean himself, but found him too antsy to sit still long enough to capture the correct emotion. Yes, every summer Ashton would sit scribbling on Bobby's wooden floor with a piece of charcoal in hand - until one summer she wasn't.
For as long as Ashton Singer could remember, those damn Winchester boys would come to her home and invade her privacy. The little one, Sammy, wasn't so bad but the older one was far too cocky for her tastes. Even when he was young he boasted that he was the best shot in three states. Every summer he would come into her home, and stare at her as if she were an alien, then turn his attention to her father's piles of books of everything supernatural. Every summer John and Bobby would tell them how one day they would love each other. Every summer, Ashton despised the fact that she had to look at that goofy Dean Winchester from the moment she walked into the kitchen in the morning to the time she went to bed at night. She hated that he preferred shooting with her father to spending time with her. Ashton hated that Dean told her that she would never be a good shot because she was only a silly girl. Yes, every summer Dean would come to the Singer Salvage yard and work on the cars - until one summer he didn't.
And undeniably they both hated that they had to treat each other pleasantly until, at least, Bobby and John were out of the room plotting their to-be engagement. When they were twelve years old, Ashton 'accidently' broke three of Dean's fingers by shutting an old Plymouth's hood on it. That same summer Dean mysteriously broke his left leg in the Salvage Yard. John took Sammy and Dean from Bobby's early that summer. Still, no matter what abuse Dean was made to endure because Ashton was a girl (and John told him that it wasn't right to retaliate against a girl which only infuriated Ashton all the more), the patriarchs of the Winchester and Singer families insisted that one day they would think very differently about each other. Both Dean and Ashton rolled their eyes in scepticism while little Sammy smiled on - believing the elders fairy tales.
When Ashton was fifteen a peculiar thing happened - Bobby made her pack in a hurry and stuffed her into the old pick-up only to rush to Ohio in a hurry. The only thing he said was that they couldn't keep John and Dean waiting. She would have protested - told her father that she got car sick and didn't want to see the Winchesters, but with their particular line of work, Ashton sensed that something was very wrong. Just as every summer, Dean and Ashton were forced to be pleasant to each other.
"But Dad!" Dean protested, "There's a –"
John simply shook his head, "Properly greet Ashton and then we'll take care of it."
And after a very brief hug that was sufficiently awkward for both of them, Dean, Bobby and John all departed. Ashton never found out what it was that John and Dean needed help with and spent two days watching movies with Sam in John's hotel room. When they came back sufficiently bloodied and injured, Ashton knew that the job had been done. That was the only time Ashton saw the Winchesters that summer and had forgotten about them until the next summer.
When Dean arrived at the Singer Salvage Yard the summer of his seventeenth year, he suspected that the stay would be short-lived. He was basically an adult now, after all, and his father needed him more every day as much as he hated to admit it. He also suspected that she would be sitting on the couch, her glasses barely hanging on to her face as she perfected a portrait or added the finishing touches to a drawing. However, when he entered the room Ambre was no where to be seen. Bobby smiled at his friends and accepted them into his home alone.
"Where's she at?" Dean asked, curiously. He peeked around the corner into the turquoise colored room she called her own. It was empty and silent.
"Out back - she's almost always out back now." Bobby said.
Curious, Dean headed out back to the salvage yard. He was awe-struck when his eyes landed on the gorgeous woman bending over the engine of an American Muscle car that badly needed a paint job. A professional-looking camera sat on the roof of the car. She was wearing short, cut off denim shorts and an old flannel that had the sleeves rolled up to the elbows. Long black hair cascaded down the woman's back like a raven waterfall. Dean wondered who it could possibly be bending over the car and was almost dumbfounded when she straightened up. The woman turned out to be none-other than Bobby's only daughter. He was almost nauseous to think that he was getting turned on by Ashton Singer.
"Hey!" He called, "If you touch that car you'll break it!"
She looked up, her long hair swinging over her shoulder as she turned abruptly. It seemed as though she almost got whip-lash. She blinked a few times, "Dean?"
"No. The fuckin' candy man. Who else comes here every summer?"
Ashton sighed, "Some things never do change."
That summer Ashton tried and failed several times to get Dean to be a model for her. She claimed that it was a project for school but Dean never seemed to believe her. John and Bobby began to lose hope that they would ever have feelings for each other that weren't malicious or unpleasant. There was only one summer left until the metaphorical birds learned to fly on their own and if they couldn't learn to love each other in the eleven years they had known each other it was likely that they never would. The only one who never lost hope was Sam. It was late one night when thirteen year old Sammy stared at his brother from his spot on the floor.
"Why don't you go out with Ashton?" He asked.
Dean cocked a brow as he was staring back down at his younger sibling in disbelief, "She's not attractive that's why."
Sam could tell when his brother was lying and knew he was then, "I think she is."
"If you like her so much you should ask her out." Dean snapped.
Sam smiled a bit to himself, "Aw, Come on Dean. I know you like her!"
"I'd like her better if she'd lose when we played poker," Dean murmured.
Sam smiled a bit to himself, "Maybe I will ask Ash out."
Dean mumbled something like 'the hell you will' and rolled over. The next day Sam sincerely planned on asking Ashton out, but both of the Winchester brothers were shocked to find out that she already had a date that Saturday night. Bobby was not particularly happy about it and when Ashton left with the tall, attractive eighteen year old, she was followed by Bobby and Dean in one of the more inconspicuous of Bobby's pick-ups. They picked up a few burgers and sodas for their stake-out. Bobby was more than amused that Dean was coming with him to stalk his daughter - he was ecstatic. After all, if Dean was jealous that meant he had feelings for her and Dean was clearly jealous.
"Who is this guy anyway?" Dean asked after swallowing a bite of burger and washing it down with a sip of Coke.
Bobby swallowed a drink himself before replying, "Some hockey player that she met at school. Likes him a lot I reckon; she's been out with him a few times before this."
Dean nodded to himself as he watched Ashton with the guy. She hadn't even told Dean her boyfriend's name. The more he watched the more it pissed him off. There, in plain sight, another guy had an arm around her shoulders. He constantly snuck in kisses while no one else was watching and Ashton only reciprocated.
Bobby watched Dean rather than his daughter - he trusted that she wouldn't get herself into too much trouble - and found himself invariably amused by the young Winchester's facial expressions. There was little range; disgust to anger and back again.
"What do you think of him?"
Bobby shrugged, "Just as much of an idjit as the next eighteen year old male."
Dean looked over at his pseudo-uncle surprised. He didn't have more of an opinion of the boy his daughter was dating other than that he was a hormone-motivated teenager just like the rest of them. Wasn't he worried what would happen if Ashton told the boy what the family really did for "fun"? No, Ashton would never spill her secrets - she hadn't even told Sammy that she had a boyfriend and Dean knew that Sam called her when he had bad days.
It wasn't long before the date ended and Dean found that Bobby was speeding home so they wouldn't be caught. They were in luck, apparently, because they made it home only a few moments before her date's car pulled into Bobby's driveway. They were sitting nonchalantly on the couch talking about guns when she entered. She smiled brightly at them, "I know you followed me."
Bobby laughed, but Dean looked horrified. How had she known? It didn't matter, he decided as she sauntered into her bedroom, because she didn't seem to mind that she had been followed. She didn't seem to care in the slightest; in fact, Ashton seemed incandescently happy with herself. Dean got up and stood in her doorway, "What's his name, anyway?"
Ashton looked up, startled. She had been searching in her dresser for something when he came in. "His name is Evan," She replied, pushing her hair behind her ears and searching through the drawers once more. "Why are you asking, anyway? You've never been curious about my friends before, Dean."
He couldn't deny that this was true. Dean hadn't had the slightest interest in any of Ashton's affairs before this summer; he hadn't cared what kind of people she talked to or dated. But now he felt strangely jealous, "Just asking. What's he like?"
Ashton looked up skeptically from her search once more. Dean was sitting in her bed looking around her room now. There was a crucifix hanging above the head of her bed and a Kurt Cobain poster on the wall next to it. On the tall dresser against the wall was a huge Beauty and the Beast snow-globe that Bobby had gotten her one Christmas. Dean still found it odd that any offspring of Bobby's could be so - so feminine. There was a picture of her mother, a woman Ashton had never gotten the chance to know, next to the snow-globe. The older she got the more she started to look like the woman in the picture.
"He's ... not like you," She replied.
Dean rolled his eyes, "Of course he's not like me. I'm–"
"He cares about me, more than I deserve him to," Ashton nodded sitting next to Dean and resting her head on his shoulder. It was hands-down the most affectionate she had ever been to him on her own accord. Dean realized then, that she wasn't just a pain in his ass that he had to deal with every summer for as long as he could remember. Ash was a human being just like he was - she had feelings, hopes, dreams.
"Why do you say that?"
Ashton shrugged as she grabbed a book from her night stand (The Stand by Stephen King) and opened the giant book to the middle where a bookmark saved her place. She began to read without really answering Dean at all. The next day John arrived to pick them up and, for once, Dean wasn't ecstatic to get away from Ashton - quite the opposite actually.
"She used to such an ... ugly duckling," He mumbled to himself as they drove away from the Singer Salvage Yard. John looked over at his son, one eyebrow raised in skepticism. Sammy was reading one of Ashton's Stephen King books in the backseat and ignoring the conversation.
Dean looked over at his father, "What?"
"You're mumbling to yourself about ducklings."
From the backseat Sam laughed.
"Ashton... she's –"
John smiled, knowingly, "Grown on you?"
Dean brooded in the passenger seat, "No. I'm just concerned that she's dating."
"You date," John reminded.
"He doesn't date – " Sam began.
"Shut up Sam!"
The next winter and spring passed by more quickly that Dean had expected it to and, before he knew it, he was back at Bobby's house. When he walked in he wasn't surprised to find that Ashton wasn't drawing. Bobby told him she was in the backyard shooting. When Dean asked if that was with her camera or the shotgun, Bobby replied that he didn't know. A shot rang out signifying that it was the latter. Something must have been wrong.
Dean and Sam left the house and took an excessively long walk to get to where Ashton was. She was aiming the gun to shoot again when the Winchester boys approached. She seemed angrier than usual, but was just as attractive as the last time they had seen her.
"You alright?" Dean asked.
She turned around quickly and gave herself vertigo. Ashton leaned with her hands on her knees, to regain her balance. She shrugged, halfheartedly, "Not my best, I must admit."
"What's wrong?" Sam asked. He was only fourteen, barely pubescent, and still the only real gentlemen she had ever spoke to.
She smiled lightly at him, "Just one of those days. I didn't even know you two were on your way here."
"Bobby didn't tell you?" Dean asked, skeptically.
Ashton shrugged, "I'm sure he did. I probably wasn't paying attention."
A few weeks passed and seemingly Ashton had reverted back to her old self. She was spending her time drawing every second of every day and if she was not drawing she was taking photos. Sam was much more obliged to model for her than Dean had been in previous summers. It wasn't often that she would get film developed, but when she did Dean was always curious to see what she did. It surprised Ashton when, one day, she found Dean flipping through one of her various sketch-books in awe.
"What exactly are you doing Dean Winchester?" She asked, playfully.
"You're actually talented."
Ashton shrugged, "To your untrained eyes, maybe. What are you looking at?"
He held up the book; a portrait of himself was exposed to Ash. She felt nauseous and weak in the knees, but kept her composure. Truth was, she had dreams about Dean often. Corny, stupid, romantic dreams about Dean Winchester. When she woke up, she often felt the unnerving, uncontrollable need to draw him - so she did.
"What did you do? Steal a picture from my dad?" Dean asked.
Ashton shook her head as she sat next to him, "Nope. I drew that from memory."
"I've seen you every summer for twelve years and that surprises you? I practically draw Dad from memory unless he's researching and sitting for a long time."
"What about my Dad?" He asked, flipping through a few more pages.
"I had Dad take a picture last summer when John wasn't looking." She replied earnestly, "Why are you looking through this anyway?"
Dean shrugged and ignored the question before leaving the room to go work on one of Bobby's various junk-cars. Hardly a day had passed that Dean spent without thinking about Bobby Singer's daughter in a way that he really shouldn't have been. He could hardly describe her as sexy - at least not verbally, but when he felt like being truthful with himself he often thought she was very attractive indeed. Ashton, of course, had the same feelings for Dean - though she would not admit this to herself.
"So, I've got a question to ask you," Dean began a few days later as Ashton lay in her bed reading an issue of Rolling Stone that had the Foo Fighters on the cover.
She looked over at him, smiled slightly, and said, "So ask."
In all the years Dean had been asking girls out on dates, he had yet to be nervous about it. Well, that was until now. He felt nauseated as he stood there trying to keep his cool. "Do you want to go to get something to eat and maybe go to a movie on Friday?"
Ashton seemed to have stopped breathing and blinked once deliberately before speaking or even nodding. "Dean Winchester, are you asking me out on a date?"
Dean nodded unsmiling.
"Did John or Dad put you up to this?"
Dean shook his head.
"I suppose I could go on a date with you," She replied nodding softly, "But you know they're going to follow us, don't you?"
He shrugged, "Maybe they will."
She smiled at him.