AN: Okay so I'm stretching the timeline of the episodes in this fic so I can have Oswald and Isabelle get closer. I've had this plotted out for months and can finally get down to it. I know exactly how I'm going to do this up until the mid-season finale. Anyway thank you guys for reading/reviewing/following and favoriting! Enjoy and please review! There are so many other great Gotham Oswald/OC fics out there so thank you for taking the time to read mine!

Playlist:

Fever Ray-The Wolf (I chose this song because obviously Mooney's a wolf and Oswald is definitely a wolf in sheep's clothing and it just works well for me as well as for the overall feel of the fic so far).

Madeline Follin-Only Lovers Left Alive OST-Funnel of Love

The Boxer Rebellion-Diamonds

Blue Foundation-Eyes on Fire

The Eagles-Life in the Fast Lane

St. Vincent-The Antidote

Bassnectar-Calling From Above

Chapter 10

Isabelle's first evening at work went smoothly. She learned the ropes quickly and Miss Mooney was more than pleased to have James Gordon's niece under her vigilant eyes.

After Isabelle finished helping clean up the bar she pulled on her trench coat and swapped her heels for her Chucks.

Miss Mooney called her over to the table she was sitting at.

"Yes Miss Mooney?"

"Have a seat dear," Fish smiled. "How are you doing?"

"Good Miss Mooney, thank you for asking."

"Of course sweetheart. You did great today. You're a quick learner, I like that. Now tell me do you know who a Carmine Falcone is?" She took a sip of wine from her glass, peering over it at Isabelle.

"Um, no ma'am I don't. Should I?" she responded.

"Oh I really didn't expect you to but I will tell you that he has an interest in you."

"Why?" Isabelle asked, feigning ignorance easily.

"Now you don't worry about that but if he comes in you are to hide. I don't care if that means sitting behind the bar for an hour, you don't come out until someone tells you to. Do you understand?"

Isabelle kept a confused look on her face as she nodded. She knew Falcone wasn't someone to mess with from what Oswald had told her back in that trailer.

Fish smiled. "Good girl. Now don't you worry, Momma's gonna' look out for you. Just be careful out there, you never know who you can trust in this city, if anyone."

"My uncle told me something similar the other night."

"Well your uncle is a smart man. Does he ever talk about his work?"

"No ma'am not really."

Mooney looked skeptical but then she smiled. "You look tired, I'll let you go. Be careful, I'll see you tomorrow evening."

"Alright Miss Mooney, goodnight," she said before rising from her chair.

"Goodnight dear."

~O.o~

The next few nights went the same, work went smoothly and she was careful to keep an eye out and her hearing sharp for any helpful information.

After the usual dinner with Jim and Barbara and a hot shower Isabelle lay in bed listening to the same song over and over as she thought of Oswald. It had been a few days since the encounter in the alley and she couldn't help but wonder when she'd see him again. She kept going from thinking about him to thinking about how ridiculous it was for her to be thinking about and even the fact that she kissed someone she really barely knew. There was something about Oswald Cobblepot that drew her in, like a moth to a flame, or perhaps it was that she knew he was a wolf in sheep's clothing. He could go from killing someone to being the most proper and polite gentleman there was. He was a bit like her feelings, one second she couldn't wait to see him again but then the next her head screamed at her to dispose of such thoughts for good. He was bad which meant he was bad for her. There was a chance she could get hurt, emotionally and physically. She couldn't help it and being too tired to read she fell asleep thinking about him.

After breakfast the next morning she decided to go to the Gotham library and apply for a library card. She dressed, donning her plain black flats and her black faux leather jacket over her clothes. She didn't carry her purse in Gotham, instead keeping a small wallet and what little she needed tucked inside her jacket. It was best not to show potential muggers she had anything for them to steal as she walked down the street.

She was unaware that Oswald Cobblepot had spotted her as she walked down the street and was now following her. As she was about to cross the street he appeared by her side.

"Good morning Isabelle," he said.

She jumped, heart racing. "Oswald," she hissed. "What the hell?"

He chuckled. "My apologies and that sort of language is unbecoming if I may be so bold."

Isabelle raised a brow at him as they stepped onto the sidewalk in front of the library. She turned to face him. "What are you doing here?"

He gently took hold of her arm and pulled her to the side. "I saw you and thought I would," he paused, looking around. "I thought I would, well, you said you wanted to see me again and I thought perhaps I should take you out for dinner?"

"Oswald Cobblepot," she whispered, "are you asking me out on a date?"

His cheeks were pink and she smiled at the adorable picture before her. He was truly nervous as he pulled at his tie and answered "yes. I am."

"I'd love to go to dinner with you," she smiled.

His face brightened immensely. "I'll be at your door at seven. Please dress formally," he said before taking her hand at the last minute and placing a kiss on top of it.

This time Isabelle blushed and she nodded.

She watched as he went off down the sidewalk, dragging his foot, until she couldn't see him anymore. She took a moment to herself in front of the library because her heart was still racing, whether that was from Oswald's surprise appearance across the street or just Oswald himself she wasn't sure.

~O.o~

She spent the rest of that day reading from her pile of library books. She'd managed to get the night off from Mooney's. She figured the only reason Fish was letting her take the night off was because she was Gordon's niece and Falcone's interest in her.

"Knock, knock."

Isabelle looked up from her book to see Barbara standing in the doorway. "Hey."

"Hey, so shouldn't you be getting ready for your date with Peter? I can help."

"Yeah, he'll be hear in about an hour. I don't have a dress though, I was hoping…"

"I've got one. Come on, follow me."

Isabelle did just that, looking around as they entered Barbara and Gordon's bedroom. She sat on the chair in front of Barbara's vanity and watched as Barbara rummage around in her closet.

"Aha! This should fit."

Barbara turned around, a dark purple dress in her hands. "Come on, try it on."

Isabelle took into the bathroom. Barbara was right, it was perfect. The silk was soft against her skin. It had a sweetheart neckline with one inch wide straps on the shoulders. The length was perfect too, not too long but not too short, stopping just below her knees.

She stepped out of the bathroom and couldn't help but smile at the look on Barbara's face. "Oh it is perfect. You look beautiful!"

"Thanks."

"Okay how about shoes?"

"Well I'll just wear my heels from work," Isabelle told her.

Barbara nodded. "You know I don't know why they make you wear heels at a café. Wouldn't flats be more comfortable at least."

Isabelle just shrugged her shoulders.

"Okay, let me do your hair. Sit," Barbara commanded.

Isabelle sat back down on the chair at the vanity.

Barbara went to work, pulling a brush through Isabelle's hair. "So are you nervous?"

"Yes."

"Peter Humboldt huh? How did that happen?"

"We just ran into each other today on the street. He remembered seeing me and just asked me out." Technically it wasn't a lie. That's exactly what happened.

"Well Jim told me you didn't do much dating at college so I'm glad you're branching out some."

"Yeah, me too."

"There," Barbara said. She'd pulled Isabelle's long dark hair up into elegant bun and had left a few strands on either side of Isabelle's face free. "All done."

"Thank you Barbara."

"No problem. How about your make-up?"

"I'll do it but thanks."

Ten minutes to seven Isabelle slipped on her heels and sprayed a spritz of her perfume. She did one turn in the mirror as the doorbell rang.

She left her room to see her uncle answering the door. "Peter? What are you doing here?" he asked, voice strained.

"I'm here to pick up Isabelle."

"Isabelle?" he turned to look at her, realization setting in as she walked up to them.

"Why didn't you tell me?"

"Oh Jim, leave her alone. Let her have some fun," Barbara said.

"I don't think that's a good idea."

"Why not?" Isabelle asked, part of her hoping he'd admit that he knew exactly who Peter was to her and Barbara so she could quit lying to them but the other half worried he would do just that.

Jim sighed. "Fine. You can go. Be back by eleven though." He looked pointedly at Oswald.

"I promise sir. Don't worry, she'll be safe with me."

The look that came across Jim's face after Oswald's words had Isabelle rushing out the door. "Bye, see you guys later," she waved before shutting the door.

She let out a breath as she looked at Oswald. Once again he was dressed impeccably.

"You look great Oswald, very handsome," she said as they walked down the hallway.

"Oh I am nothing compared to you this evening. You are the most beautiful young lady I have ever had the honor of setting eyes on," he complimented her, his nervousness showing through in his voice.

Isabelle blushed profusely and looked down, "thank you."

After dinner at one of the fanciest restaurants in Gotham, which was also at the opposite end of the city from Mooney's, they were walking down the street. Oswald had chosen to sit in one of the darker booths near the back of the restaurant, being careful not to be seen by anyone that might come into the restaurant who may recognize him.

They walked down the street, Isabelle's arm hooked in Oswald's, who was being gentlemen as ever. They could hear music thumping; getting louder the further down the street they went. Isabelle could see they were nearing the entrance to a club.

"You know I have never been in a club like that before," Oswald said.

"I did once," Isabelle said.

Suddenly she grabbed his hand in hers, surprising him, and walked ahead pulling him along with her.

"Isabelle what are you doing?" he asked.

"Let's go in."

"Wh-what?"

"Well you haven't been to one and when I did go to one it wasn't the best experience so let's go together."

"I-I don't think that's such a good idea."

"Don't worry Oswald I'm not much of a dancer but I'm in a particularly good mood tonight and I'm not ready to say goodbye to you just yet this evening either."

Oswald didn't know what to say to that. A girl had never said anything like that to him before, much less wanted to go to a club with him. She wasn't ready to say goodnight to him and she wanted to spend more time with him. He wanted the same.

"Wait," she said, stopping abruptly and turning to face him. "Take off your jacket and your vest."

Oswald took a step back. "What?"

"You can't go into a club wearing a full suit like this."

"Oh," he relaxed a little and slowly did as she said. "How's this?"

"The tie too."

He took it off folding it over his arm with his jacket and vest. Isabelle reached up slowly and unbuttoned the top two buttons on his shirt. "Okay much better."

Oswald smiled, his heart beating in anticipation of the prospect of dancing with Isabelle within mere minutes.

There was a short line so they didn't have to wait long. Isabelle made her way to the bar and took Oswald's garments from his arm. "Excuse me," she said to the male bartender. "Could I set these down under here?" she asked, pointing to a shelf underneath the bar.

"Sure thing sweetheart," he smiled at her and took the clothes from her. "Can I get you anything?"

"Um," she bit her lip. "Two tequila shots please."

He nodded, smiling at her.

They took in the club. When they entered Oswald immediately noted the smell of cigarettes and other substances clashing with the perfumes and the colognes that the patrons wore. The red lights that flashed on and off gave the place a sort of weird ambiance as he looked around.

"Thank you," Oswald said as they sat down. "For making sure my clothes are taken care of."

"Of course."

They downed the shots and Isabelle asked for another. After they downed those she got off the bar stool and grabbed Oswald's hand.

He followed her out into the throng of gyrating bodies. Instead of backing up against him like a lot of the other young ladies seemed to be doing with their men she faced him, wrapping her arms around his neck, her face close to his. He placed his hands on her waist and swayed to the rhythm of the song with her.

"Thanks for asking me out tonight Oswald. I'm having a great time!" she yelled over the music.

"It's my pleasure I assure you. Although I wasn't expecting this part," he chuckled.

"Well neither was I," she said careful to keep some space between them.

Oswald was feeling absolutely elated. It was a combination of the alcohol in his system from the shots and the wine from the restaurant and the atmosphere in the club but mostly because of Isabelle. He could smell her perfume, a light floral, fruity scent with a hint of vanilla. She was intoxicating, he thought, as he pressed his nose to her neck and inhaled her scent, pulling her closer.

He figured he did what he did next because of his senses being overwhelmed, her scent, and her arms around him, how she felt in his arms and just the elated feeling he was having. He stared at her for a moment, the pulsing red lights illuminating the light sheen of sweat on her shoulders and collarbone. Her hair was coming undone; more tendrils falling down to frame her face and brush her shoulders and back. She was beautiful to him, the most precious thing he'd ever held in his arms and she would be his. Together they would rise in Gotham, be revered and feared. He would give her everything. He surprised her by leaning down and initiating a kiss. He was more enthusiastic than the last one they'd shared, taking control as he pulled her against him. When they broke apart their breathing was elevated.