Just a little oneshot of Rumplestiltskin and one of his more intriguing deals. With a bit of social realism for OUAT. Seriously guys, not every deal made with Rumple is going to be some story-changing, OUAT turning point. Sometimes, a deal is just a turning point for 1 girl's life.

So... there's a girl named Anenfel, interested in this mysterious Dark One, maybe even trying to impress him or interest him in her life by asking a specific question. She literally puts her life in his hands… just to see what he would do.
So what are you waiting for? Let's see what he does.

By Moonshine and Candleflame

"Well… That's an… unusual request you've got there,"
The Grey Dealmaker was not hesitant or taken aback in his words, as one may expect. On the contrary, they were a bit maniacal, like he was about to laugh. Anenfel was immediately taken aback by how layered his voice was, accented and tweaked beyond what was natural. It was unusual, odd, peculiar, but strangely intriguing.
"And why, my dearie," He smiled a crooked, yellow toothed smile. "would you have me make this type of decision for you?"

Anen had not needed to look far for Rumplestiltskin. Like the whispers had said, when you needed him, he just happened to turn up. You realized your only hope was the Dealmaker, and he just… found you. Strangely, even if one needed him, they'd never ever expect him. Unanticipated, he would just… Appear. Anytime, anywhere. Without warning. Even if you requested his presence, even if he knocked on the door… his predicted arrival would always turn out… unpredicted.
Out of nowhere. Behind your turned back. Right in front of you, as you blinked. Or, as poor little Anen had it, right next to you, high-pitched whispering his existence into your unsuspecting ear in the dead of night. No doubt, she had jumped. Even given a small, hastily stifled scream. Of course, he laughed cruelly at that.
Rumplestiltskin was strange. He was terrifying. But, most important for Anen, he was unpredictable in the most acute and precise of ways. Everything he ever did was done with a purpose, and he was never limited to the mind of the ordinary.
So Anenfel had gone to him for advice. Not just any advice. A question, one she was certain only he could answer in the right way. She had been thinking about it for a very long time. Brow creased, she had stared into the finger of fire in the candle flames, considering. Light captures the mind, and the drop of light was an anchor for her tired eyes as she thought. Even now, she had just been watching the light of the moon and stars from the reflection in a puddle. Then, of course, that creature had made his surprise appearance, and she spilled her undecided decision to him as soon as she realized who it was.

Anenfel had asked Rumplestiltskin whether or not she should kill herself.

"It's a very interesting question," He rambled in that queer voice. "Well, why not?" His eyes, cloaked in shadows created by Anen's torchlight, slid over to hers. He leaned his head close to her ear, like he was whispering a secret. "Give it a go. See how that turns out for you."
Anen did not react at first. After a moment, she looked at him and smiled, almost knowingly.
"You asked I'd let you make such a decision," She remarked, slowly.
"Correct, I did." He nodded with a crooked grin. "And why is that?" Anen crossed her legs on the bed on pine needles, and Rumplestiltskin crouched next to her.
"Well…" She ran through her reasoning, seeing how to put it all into words. "You are the Dark One. The Dealmaker. You're the only one who would even consider saying 'Give it a go'. You're unpredictable. You don't have a human mind."
"You just want me directly involved with your life, dearie" He said as though he knew all along, and grew bored of her trying to figure it out. "I have better things to do."
"And I don't." Anen cut in, a bit annoyed, but sad. "I don't have better things to do with my life, that is. Anyone else would send me to a doctor so that I can get my mind forced to change what I want. You're not human. You have the ability to tell me to go ahead and do it. You're able to confirm my thoughts on… what I want."
"And what do you want?" He didn't skip a beat, Rumplestiltskin. It was as though he had prepared for her every word.
"That's why I'm asking you." The girl sighed. "It's a concept I find hard to wrap my head around. I can't really…" Her voice trailed off.
"Put your finger on it?" Rumplestiltskin let out a ripple noise only describable as a giggle as he whipped up a gnarled, pointed finger. Anen, caught up in his strange laughter, couldn't help but release a hiss of air through her teeth as she smiled. She swallowed and continued.
"I don't really want to die, not really… But I don't really want to keep on living. My world seems shaped as though I wasn't even meant to live."
"You have nothing to live for and nothing to lose." Anen looked to the Dealmaker.
"Yes exactly," Her voice was monotonous as she searched his face. Anen expected to see some sort of recognition of how she felt in his expression. That was not the case. His gnarled teeth and hollow eyes showed nothing more than their usual insanity, despite his ability to echo her thoughts so perfectly.
Rumplestiltskin saw her looking. "Don't look so surprised, dearie. You're a very open book. You trust too easily. So, how worthless is your life to come crawling to me?" Anen's eyes widened a bit, she was a bit stung by his sudden question.
"I… I don't know my parents." She began with the family. The family she wanted to have, but didn't. "I move between families. I have no real home. I will never have power or influence or even much money. I have very little friendships. I've been deciding that I'll never be truly happy in this life."
"And!" Rumplestiltskin was on the verge of another fit of giggles. "You will never be remembered! No one will mourn your death! None will suffer from your passing. So, what keeps you? Why not?!"
"But I've never really been sad, either," Anen wasn't trying to argue, but his laughing fits were a bit out of place at the moment and she was a bit amazed he could laugh at a serious topic. Unpredictable.
"But that, dearie," The words were dramatic, more pointed and forceful. And so strangely accented. "That is just it! This is an unfeeling life! It doesn't suit you. You deserve something with more substance!" He was right, Anen realized. She did. She wanted, no, deserved something better.
"I want parents," Anen smiled at the thought. She became entranced in the ideas that were being presented to her, flooded with the possibility. "I want a life with a real family. Not this. Not this life."
"And THAT'S why I'm here, sweetheart!" Rumplestiltskin zealously jumped up, bowing dramatically with a flourish of his hand. "To send you off to a better life! Like a Cinderella to the ball!"
"You can do that for me?" Anen stood as well, staring, wonderstruck, at him.
"Glass slippers and all,"
Just like every girl who had ever met the Dealmaker, she was utterly, emotionally powerless to the opportunities he offered. She was no different from any other of his clients.
Her torch nearly slipped from her hand; it was shaking slightly with fear and excitement.
"Besides, dearie, would I be here if I couldn't?" Rumplestiltskin gave another crooked grin. He knelt down; a tiny crystal bottle had appeared in his hand. He leaned over and dipped it in the small pond of water in which the moon and stars were reflected. Anen watched, curious, as the silver light from the moon seemed to slip inside the tiny vial. It was filled with the glowing silver fluid. "And a bit of this…" Rumplestiltskin muttered, his words a bit slurred, as he straightened himself up. Without warning, he thrust his pointer finger into the fire of the torch Anen carried. She didn't even have time to be startled. He drew back his grey hand, a drop of golden candle flame alight on the tip of his finger. Before Anen could really see what he had done, Rumplstiltskin had already slid the flame into the bottle. Swirling in it now were the silver and gold lights.
"There you go," He delicately dropped the bottle into her hand, making another high-pitched giggle as she hastily caught it and nearly spilled the potion. Anen clutched the bottle tightly, not wanting to drop it. Carefully, she held the glowing mixture up to her eye.
"And this will…?" Anenfel knew, but her mouth didn't want to form the words.
"Kill you," Rumplestiltskin cackled, almost offhandedly. "Poof!" He executed a quick gesture with his crooked fingers. "Stone dead, you'll be. Until, of course," His voice sobered a bit. "You're peacefully reborn in a new life. A better, happier life."
"Is that a promise?" Anen couldn't help but ask. "All of that? Promise?"
Another giggle. Another crooked smile. "I promise."

Anen realized.
"What about payment? You'll want something in return, won't you?" She looked at the bottle, wondering the cost. A sane man would want gold, but the Grey Dealmaker never seemed to want gold. He was always after something more… bizarre.
"Smart girl," Rumplestiltskin smiled wider. "You got there before I did. Yes, all magic comes with a price. But you," He leaned closer to the dark haired girl, tilting her chin up with the crook of his finger. Anen shivered, but she had a feeling it wasn't just fear that made her do so. "You have nothing in this life. Nothing of any value to me. Nothing of my use. But, in your next life," He tapped the bottle, and it clinked lightly. "you can owe me a favor, kay? Promise?" He took her earlier words with a tricky, pleased-with-himself smile.
"Promise." Anen nodded, looking at the ground. "But will I remember any of this?"
"Nope!" Rumplestiltskin shook his head, his voice cracking up in near-laughter. "But that's why we have these," Anen watched him draw a scroll of parchment from... out of nowhere, really, and throw it open with a wave of his hand. The sheet unrolled dramatically. His other hand offered a large white quill.
"And you just happened to have one ready for me? Anen smiled, mock incredulous. "I'm flattered."
"Don't be, dearie," He voice was light, but surprisingly laughless as she plucked the quill from his hand. "I've a contract for every occasion."
"A contract for every occasion," Anen repeated to herself, thoughtful.
"Now, sign on the dotted line,"
"Yes. Right. Of course." She pulled herself back, raising the quill. Without another thought to it, she signed Anenfel with a golden flourish. She hadn't even needed a surface to write on.
"Thank you very much," The Grey Dealmaker rolled the contract back up in a very businesslike fashion, tucking it away as quickly as he had brought it out.
"I should be thanking you," Anen whispered gratefully, holding the bottle to her chest. Her closed fingers could feel her heart beat incredibly fast through the thin cotton of her dress.
Rumplestiltskin nodded, a hint of the word yes hissing out of his mouth with a hasty breath. He lingered for a moment, almost... unsure.
A feeling that she was messing with something unfathomably bigger than herself jabbed Anen in the side. It quickened her pulse, and gave her that sinking feeling in her stomach. She was nervous. She had signed a contract with Rumplestiltskin, the Dealmaker himself. He had given her a potion that would... kill her. And if it worked the way he said it would... Anen's mind couldn't even comprehend the idea.
"Thank you," Anen nodded to the Dark One, smiling one last time.

"Before I'm off on my merry way," Rumplestiltskin, who had turned to leave, looked back at her. "I am required to ask, what will your name be, in the lovely new life of yours?"
"Anenfel," She told him, not even aware she could choose something like that. Dipping her head a bit, she spared another quick curl in the corners of her lips. "Always Anenfel."
"Then I'll be seeing you again, Ms. Anenfel," He turned and started off through the woods, on no apparent trail. Anen listened, almost desperately, to his voice, hearing it get quieter. "Eighteen years time, you'll owe me a favor!" It was the last voice she'd ever hear with these ears.
Anen sat down on the pine needles, looking into the dark trees, trying not to ponder on the consequences of her actions. She could not risk wondering what her death may leave behind. So, without anymore hesitation, she lay down on the forest floor.
In the cool night, she would die under the moon and stars. In the quiet peace, listening to the crickets, Anen decided she would like to lay in tranquility. It was a dramatic, even poetic, place for her body to rest.
"Goodbye, and good luck," In the distance, she heard his voice one last time, and with all her willpower, she held onto it. Replaying his words in her mind, Anen looked to the star-sprinkled skies.
She had no goodbyes to write.
She had no loose ends to tie up.
Anenfel was ready to go.

A foolish, thoughtless wish came to Anenfel, as she brought the tiny crystal bottle to her lips.

Fleetingly, she wished Rumplestiltskin had stayed with her until she died.

Yep.

There you have it. Sorry if you didn't like Anenfel. I can understand if suicidal characters don't play well in some people's minds.

This is just a oneshot, but if enough people like it, I can consider it a prologue to a slightly more elaborate story. With the favor in eighteen years time, etc.
I don't know what the setting would be, though. My original plan was to keep it in FTL, but maybe it might makes sense to bring Anenfel (probably namechanged to Anna) into modern times. Idk.
I know it wasn't a light, funny story (you know, the kind any person can handle), but I hope you liked it!