This takes place pre-Gotham, as I wanted to try something small and AU. I was encouraged by Lola93091, thank you and this is for you!

Disclaimer: I own only the OC's and the AU plot devices you don't recognize.

He was tall, lean, and completely arcane. The color of his midnight hair ran ominous down to the base of his neck, like a murky river. He was pale like a full moon, and the surfaces on his perfect teeth were blinding as he smiled convincingly to the woman behind the front desk, charming like a worm on a hook. She responded in kind, doe-eyed and bashful.

It might have escaped others comprehension, but Oswald was not describing himself. He was a silent spectator to the inveigler at the hotel desk, dressed as smartly as him in a dark suit. The conversation he was sharing with the woman was too hushed for him to hear, like a breeze caught up in a storm, but their signals were obvious. In fact, Oswald prided himself on his ability to read people and dire situations, it served as a useful tool in his line of work. Then again, it might have been the very reason he was into his line of work at all, if one could call it that. He was still a lowly acolyte to Fish Mooney, something that was unchanging.

He was currently in the middle of a task of completing a job she had given him (one of the many), something he wouldn't have volunteered for if it had been out of his way. The reason for his being there was his own, and Miss Mooney hadn't bothered to pry, only because she was too caught up in her momentary glee that the situation had worked in her benefit. So here he found himself in a rundown hotel on 52nd street, aware of his instructions while he waited to take care of his own matters first.

He quivered when a chill ran down from his neck to his shoulders, residual water dripping from his hair after the trek through the rain to get there. His knobby knees bounced up and down impatiently, his umbrella tucked between them as he sat forward in his seat. It wasn't with anticipation that he was jumping about in his seat, nor was it with dread. He was in a bit of a hurry, considering he was finishing a job for Miss Mooney on his own time.

The philandered finally got his room card, and Oswald watched with vague interest as he disappeared down the short stretch of hallway that led away into the seedy joint. No one booking a room here was from out of town, he knew this well considering what his own intentions were. This was Gotham, and nearly everything had a crime element tied to it, or some other shady matter that one wouldn't want their mother finding out about. Oswald hadn't seen his mother in a while; perhaps he'd make a visit after this day was done.

It smelt like mold and dust, and by now he was getting tired of waiting, his frosty eyes narrowing while his thin features pinched together in a horrible twist. He felt over his crooked teeth with his tongue, savoring the spearmint taste that had lingered from the mouthwash he had used before his way over. He had been so nervous that he had swallowed half a mouthful, burning his gums and causing a canker sore or two in the process. It shouldn't have been any trouble, but he wanted to appear somewhat put together in appearance. The weather had seen an end to that, and the rest of his confidence had been swallowed away by the tall, dark and more physically appealing man from the desk.

"Chester?" His head rose at the calling of the pseudonym he had given. Oswald Cobblepot might not have been a known name around Gotham yet, but he wasn't about to besmirch it in a place like this.

He rose from his seat, and his entire person thanked him for leaving the stiff cushions of the chair. All of the fluff had long since vanished from being sat in too many times, making the chair more of a relic than an actual piece of furniture. His eyes connected with the stranger who had called for him, her blue eyes filled with false life as she ushered him towards her room. He had to remind himself this was a place where business was conducted; in and out, swift and quick. The woman gave him a flirty smile which he returned with one of his shifty ones.

"Well darling, where would you like it?" She asked while twirling a curl of her fake red hair. He gazed around the small room in accordance to her question, finding nothing appealing about the vermillion walls or the stained carpet. The woman seemed annoyed by his lack of answer, hands gripping her hips tightly as she swayed from side to side on her feet. "You look like a first timer, so I'm sure the bed will suit you just fine."

He nodded once, half expecting her to take the lead. She had all the courage he lacked, stripping herself of her robe (that belonged to the hotel) revealing the thin cotton nightgown beneath. It was threadbare, and the neckline plunged purposefully by the looks of how many times it had been tugged and pawed at. She strode her way over to the bed, crawling into the sheets from where they had already been pulled back. She beckoned him forward with a finger, and he was inclined to follow as he awkwardly walked out of his own layers, save for his thin white t-shirt and briefs. He sat down next to her, feet straight up in the air under the covers with his hands folded in his lap.

"So Chester," She said with knowing that it wasn't his true identity. He wondered how many 'Chester's' she had seen already today, but then decided it was better not to think about that. "How do you want it?"

"Quickly," He responded while keeping the shrill crack from entering his voice. "Just quickly ma'am."

"A quickie for your first time hmm?" She teased, and he flinched as her thin digit trailed down the dove grey skin of his arm. "If we're moving ahead with this, you're going to have to call me something other than ma'am. That makes me feel like a grandmother."

"What s-should I call you?" He asked, cursing at the small stammer in his speech.

She leaned into him until he could smell the soap she had used previously during her shower, evident by the wet tips of her short hair. He wasn't attracted to her in the least, but then that was why he chose her to begin with. Unimpressive and unassuming would keep him detached from the event.

"Who do you want me to be?" She whispered huskily, making her sound more like she was a heavy chain-smoker than a lustful seductress.

He trembled as she moved astride him, looking up into her foggy eyes as he thought about his exceptional morning. "Rosalie." He replied in a breathless whisper.

Six hours earlier…

"Oswald honey," Fish Mooney called as she entered left from the bar in her nightclub, dazzling in a violet gown that sparkled like the midnight sky. "Come here for a moment."

He pushed himself out from the bar stool and away from the paper he had been reading. Gotham's headlines didn't really differ from day to day, especially if one had lived there their whole life. For Oswald it was the same old story, and he was brought comfort by that fact. This was home.

"Yes Miss Mooney?" He asked dutifully. Butch was at her side, his thick neck covered by a black turtleneck that he had on beneath a sky blue dinner jacket. He was sending Oswald a sideways smirk, the likes of which he was accustomed to seeing on the man's face.

Mooney surveyed him critically, and as always he shifted from such scrutiny. "I've got a little task for you, something I would only entrust to my Penguin."

Butch snorted like an animal beside her, and Oswald felt himself grow cross-eyed with anger. He did his best to keep reserved, but something about the pig noises coming from that man's mouth made him silently seethe. If he was a Penguin, then that made Butch a hog. "Anything you request Miss Mooney." He replied with airy politeness.

"We have a guest, someone I've been given to entertain for a week, but you know I get so busy, and I need someone to step into the role when I'm otherwise . . . occupied." She stated her words in drawn out sentencing, adding the odd pause for a mysterious effect. It always seemed to work too, at least on her goons. Oswald fancied himself a cut above the rest.

"You want me to?" He asked with an air of incredibility.

She threw her head back with a laugh, brushing the fuchsia fringe from her eyes as she gazed at him with the type of hunger she viewed the world in. "There's no one I trust more." She said while giving Butch an icy look. It helped to reassure him that Butch and the others weren't fit for the task.

"I won't d-disappoint you, on the contrary, it would be my genuine pleasure to do this for you," He said, tacking on sweet praise with a hint of brownnosing. "When do I start?"

"Right now," She retorted. "Frankie, bring her here."

Oswald felt his heart fall down like a lump of coal in his chest. It hadn't crossed his mind that he would have to be in the company of one who was of the opposite sex. Beside Miss Mooney and his mother, he was a bit stilted around the female species.

Broad Frankie appeared at the doorway, keeping his hands to himself while he brought in the woman beside him. Gotham's dank weather had not affected her skin in the least, for Oswald could not remember ever seeing a richer olive tone. Her caramel hair was wrapped into a smooth twist on the back of her head, and her coffee colored eyes were cast down to the floor in the most demure expression he had ever seen in the club. Her attire was neat, all white in a pencil skirt and blazer. Even her heels were pearl white, perhaps to match the chain of beads tied around her neck, collar tight.

"Oswald, say hello to Rosalie Scangarelo," Miss Mooney spoke, gesturing with her hand to the young woman who was now looking at them—or rather through them. "She is Mr. Falcone's niece, and she'll be residing with us for the week."

Oswald tried not to let his eyes widen more than he was certain they already had. "It's a p-pleasure to m-make your acquaintance ma'am." His hand was suspended in the air between them, waiting to bridge the gap of strangers, and getting clammier by the second when she didn't immediately respond to the gesture. When her eyes shot up to his he nearly flushed, but was saved the humiliation because of the dim club lighting.

"Hello." Her voice was soft and drab, a sign of her weariness and melancholy.

Their hands met in a brief shake, and then there was the embarrassing moment when she made to pull back, only for her fingers to snag as his brain still hadn't functioned to give the command to let go. He half smiled an apology, and she only winced back at the sight.

"Ms. Scangarelo, I can guarantee you will be in good hands with Oswald. He's very obedient." Miss Mooney cooed his praise, but he doubted if it was winning her over. "Is there anywhere you would like to go pigeon?"

Rosalie shook her head while she held onto her small clutch purse with both hands. "For now I think I would like a drink."

"A good idea," Fish agreed with a chuckle. "Frankie, get us something, but not too strong for this one. Her uncle wouldn't appreciate that."

Frankie computed with a head nod, not using his words like the lurch he was. Rosalie turned and followed to one of the bar stools, Oswald watching her all the way until he noticed the calculated look Miss Mooney was giving him. "I-is there anything else ma'am?"

Her full lips bloomed into a sinister smile, and he swallowed thickly in fear. "Now my Penguin, don't be getting any ideas in that silly little head of yours. I'd be helpless without your company."

"Of course n-not." He agreed.

"It looks as though I don't need you right now," She remarked, inclining her head back to glance at Rosalie who was sitting with her legs crossed, a tantalizing vision with an amber drink in hand. "But there is another problem that needs tending to. Ralphie ignored the warnings. I must not have been clear enough the first and second time. Could you be a doll and go pay him a visit?"

With no other answer plausible, he took her instructions, agreeing to the test.


He didn't feel any different after the deed was over. The woman had already left his side, fussing with her hair before the cracked vanity mirror while he straightened his waistcoat and tie. He hated the smell of the room from first entering, and it was something worse now; dirty and sinful. Fastening the button on his jacket, he stood from the bed, slipping into his shoes, belonging on his feet that appeared too long for his body. He dug around in his pockets for money, pulling out crumpled bills that he had haphazardly tucked away before making his excursion into the city.

"How much?" He asked quietly.

She looked at him through the mirror, not bothering to face him again now that she was back in the nightgown and robe. "For a first time, I charge three hundred."

Three hundred for his virginity; that seemed like a pricey business venture. It was worth it though, to at least rid himself of one of the ridiculous titles that plagued him. He tossed the amount onto the side table, and not a cent more as he made for the door with his umbrella in hand. He didn't particularly care for the way she had stepped on it while on her way to the bathroom when they had first finished, and he dusted it off and inspected it for any damage. There was no need to carry the marks of this place with him, and he wouldn't be seeing her face again anytime soon hopefully.

The door shut behind him in a cold and final manner, and he found himself back in the tight hallway of the hotel on 52nd street. He did not move from his place, looking out into the lobby where the woman behind the desk gave him the go ahead, locking the main door to the lobby while she pointed to the room door before his sight. He nodded his appreciation before she made herself scarce, and he was left alone in the hallway for his next task that needed completing for Miss Mooney. Raising a hand, he formed a fist and knocked on the door, waiting a moment before the familiar sound of footsteps came to answer the call.

The dark and handsome face of the man from the lobby appeared. Handsome Ralphie; the one who didn't pay what he owed. "What do you want?" He asked rudely, judging Oswald with his gaze as he looked him up and down.

"Hello Ralphie." Oswald said, sneering in delight.

Ralphie's eyes widened with the realization that he had been found out, and he tried to quickly shut the door and barricade himself in his hotel room, only for the door to catch on the end of Oswald's umbrella that he stuck through the threshold. He shoved back at the door, knocking Ralphie onto his back inside the room. Moving quickly, he stepped onto both of Ralphie's hands, the best way to overpower him before he could get aggressive and take the upper hand.

"Please, what do you want?" He cried, struggling like a squirming animal on the dirty rug to shove Oswald aside.

"It's too late for that," Oswald said, his voice black while he fixed the sharp end of his umbrella over Ralphie's left eye. "Miss Mooney sends her regards." And he pushed down with all of his strength, awakening a terrible scream. Ralphie shook and trembled until he went silent.

Oswald loved silence.

Well that's chapter one. I don't expect this will be a really long fic, mostly because I don't have time for it. I will carry it until it intersects into where the show started, as I don't like writing for canon material. Hopefully I got Oswald in character. I see him as feeble but nefarious, evil lurking beneath the shell of a boy. He may have a bit of a crush on Ms. Rosalie too, and that's what I want to focus on. I do plan for it to be more M-rated, but I didn't want to make a lemon out of him with a total stranger, so this chapter will start at T.

Comment below and let me know if you want to see more :)