Now, what does one wear to properly seduce a mob boss? Ann glanced down at her glittery gold dress, knowing that it was too good to be worn at a scumbag bar like the one she would be lurking around tonight, but it was certainly one of her more attractive options. Sequins of gold clung to her body, and although it was a slightly shapeless dress, it made her legs look a million miles long, and her shoulders look elegant. Everything was accomplished with this piece; she looked saucy, but not slutty, and that was the plan. Her hair was fluffed, her make-up was pristine, and her shoes added another mile to those lovely legs of hers. She looked damn fine, if she didn't say so herself. Armed with a clutch, she had trudged down to the bar where Gambol was supposed to be at around 11:30 pm, knowing that it wouldn't take long to locate, seduce, and then steal from the guy...

Look, she knew she was tooting her own horn, but she looked good. Her confidence was at an all time high when she strolled along the slightly off-putting street, and she held her shoulders back even when she heard footsteps scuttling behind her. She was a Gotham Girl, don't forget, and this shit shouldn't terrify her anymore. But it did. Every fibre of her being was shaking, though she managed to stay completely composed on the outside. It also helped that she was a touch drunk going into this thing; liquid courage never hurt anyone, all right? Heels clacking, muscles twitching, and a somewhat bored expression on her lips, Ann marched right up to the entrance of the club... bar... whatever. The bouncers had just let a pair of women pass ahead of her, and although they were certainly wearing far less clothing than she was, she knew she had that sophisticated appeal that was going to work tonight. Well, she hoped. She had never exactly tried to seduce a mob boss, and if she could help it, she never planned to do it again.

You see, she knew there was no way on earth she would have been able to simply steal the knife from him. No, she wasn't exactly subtle most of the time, and she knew the moment she tried to lift it off him – presumably from his belt or something... where else would it be? – the man would catch her, and then... well, she'd prefer not to think of what might follow. Gun shots. Stab wounds. Thrown out on her ass. All of these were serious possibilities, and Frank had better worship the ground she walks on when she does this and gets him back. All of this was for him. Over the course of the day, Ann had realized that Frank was one of her few good friends in this city that accepted her for exactly who she was. She never had to hide the fact that she could be a selfish snob sometimes, and he knew that. He made her laugh (at, not with, mind you), and he was the closest thing she had had to a male relationship in... a very long time. So despite the fact this was terrifying, unsafe, and might end up going to Hell within the first five minutes, she had to try. She had to try for Frank. So long as this psycho she was dealing with was good on his word, she would have Frank back by at least 3 am tomorrow morning, and that wasn't a moment too soon.

The pair of bouncers swung the door shut behind the two women in front of her, and Ann cocked an eyebrow. One held out a hand, "ID please?"

"What?" she laughed, staring at them in disbelief. Surely this wasn't happening. They served highly illegal mob bosses in here... and they cared whether or not she was legal to drink? When the man's face gazed back at her, dead serious, she cleared her throat and hastily rummaged into her clutch, producing a driver's license for him to examine. It was a few years old, so she was much more attractive now than in the picture, but it still looked like her. After both had examined it, it was handed back to her, and the door was opened, "Have a nice evening, Miss."

She faulted in her response, only for a moment, and then nodded, "... Thanks."

The smell of booze and cigarettes hit her the moment she stepped inside. It was a dark, musty club. Chatter and the soft hum of a girl singing on the stage filtered through, and she had to take a step back. This wasn't what she had expected at all. No, the way she imagined it was all handsy gangsters fist pumping to some irritating music on a dance floor, and everyone piss drunk. Therefore, imagine her surprise when she saw that many of the tables were full of men playing cards, women nearby, and the dance floor was scattered with a few couples slow-dancing to the admittedly romantic song. Hmph. It was going to be a little harder to get Gambol's attention when there wasn't this air of sex and scandal floating around. Biting her lip absently, Ann's eyes roamed the room, going from table to table until she found the man that resembled Gambol, based on all the photographs the department had of him. Plus she had seen him on TV a few times, so that definitely helped. A statuesque African-American man, probably in his early forties, Gambol was seated close to the bar, surrounded by a few other men who were comfortable enough to lounge in front of him. She wasn't particularly sure how the mob hierarchy worked, but these guys must have been pretty close to the boss to be able to play cards with him.

Erhm. Right.

Flicking her hair over her shoulders, she strolled over to the bar, taking a seat directly across from Gambol, and ordered a martini. Dry, thank you. Clutch resting on her lap, she crossed one long leg over the other and glanced over her shoulder, eyes roaming again until she let them rest on Gambol for a moment. He hadn't noticed her, and was instead grinning toothily as he dragged in a set of chips toward him, clearly his winnings, and the surrounding men tossed their cards into the middle pile irritably. He still didn't look up at the bar, and Ann sighed, turning her attention back round to her freshly delivered drink. Then a thought hit her. Pursing her lips, she turned back around to eye the drink Gambol had; a glass of red wine. Which was nearly empty. Catching the bartenders attention again, she told him to send Gambol another glass, on her, and tell him it was a congratulatory drink for his win. There, that ought to get his attention.

She brought the wide-rimmed martini glass to her lips and took a delicate sip, watching in the mirror behind the bar as the attendant brought Gambol his new drink. The mob boss' eyes flickered up toward her when the bartender pointed her out, and she casually glanced over her shoulder and shot him the quickest of smirks. The men toasted her with his new drink, then beckoned her over with a nod of his head. With an arched eyebrow, she slid out of the stool at the bar and sauntered toward him, trying her best to remain confident and aloof, when really her insides were jelly.

"It isn't often such a pretty lady will buy me a drink," he mused when she was close enough, pushing out his chair and patting the armrest, "and I think I've found myself a good luck charm for the night."

"Oh?" she responded, keeping her voice as even as possible as she took up a position next to him, "And what's that?"

"You," he chuckled, wrapping an arm around her waist and letting it rest on her thigh. "I won after you came in, didn't I? Then I get a free refill? I'm spoiled, and you're a gorgeous charm."

"Thank you," she grinned, noting that he had a wedding band on his finger, "I'm glad to be of service."

"Deal, Mack," Gambol ordered light-heartedly, swatting the fellow next to him. Ann downed the rest of her martini, her head swimming momentarily from the alcohol. She would have to take it slow; otherwise she was going to blow this. Being a bit drunk to get herself in the door was fine, but without her wits now, there was a chance she may end up with more than she bargained for. Especially with the way Gambol was stroking her thigh. His attention was mostly on the cards in his free hand, to which she commented on in his ear whenever she had the opportunity. She had been quite a poker player in college, though she was a touch rusty. He didn't seem to mind; in fact, he found her mistakes amusing, and would always playfully correct her with a whisper to her own ear. Every time she felt his breath on her, she cringed a little, but was pleased to see that she was a better actress than most would have given her credit for. This was for Frank.

Speaking of which... She casually adjusted her position at one point, during which she caused his jacket to shift slightly, revealing a rather large knife strapped onto his brown belt. Why on earth did that freak want it? Like she had said on the phone, it would have just been easier to buy one that looked exactly like it... all of this was so unnecessary! Flicking her hair back again, she smiled impishly when he looked up at her, a winning set in hand, and she curved her arm around his thick shoulders, whispering another set of 'congratulations' in his ear when he found himself winning for the third time in a row. Maybe she was a lucky charm? Perhaps she could consider hiring herself out to help poker players win... for a certain percentage of the earnings, of course. Hmm. Shaking her head, she cleared her thoughts of anything but getting her prize, and waited patiently as the night progressed.

It was nearly half past midnight when she realized that it was getting late. They had been playing for over an hour, and Gambol had won several hands. Half of her wondered whether his men were letting him win, seeing as he could have them killed in a heartbeat, or if she was really just that much of a charm. However, time was of the essence, and she knew that she was going to get a call in about an hour and a half back at her apartment, one that would tell her where she could get Frank. Naturally, that meant by then she was supposed to have the knife on her, but that shouldn't be too hard. Gambol had had a few more drinks, and his hands were getting bolder. Surely she could have him whipped into submission with the promise of sex in some dark room somewhere... private, of course.

Leaning down, she whispered a proposition in his ear. You. Me. Somewhere a little more private? A few of his men were heading off to the bar to refill their drinks, while some were lighting up a cigarette, and Gambol mused that it wouldn't be a problem to find somewhere quieter than here. Soon they were up, and she had her small hand clasped in his as they navigated their way through the bar. The music had picked up now, there were definitely more people, and Ann could feel her head still swirling from a recently downed drink. Hey, she needed another dose of the courage if she was actually going to go through with this!

Before she knew it, she was being thrust into a private room off to the back of the bar, his lips to hers, his hands running along her slim frame. They were an awkward match, her skinny and he muscular, though she couldn't think about that. Don't let your mind wander, Ann! She had a difficult time keeping up with him, and when he drifted down to her neck, she sucked in a large gasp of air. It might have come across as a gasp of pleasure, seeing as he was now rubbing himself up against her, but really she was just trying to breathe, damn it! Wrapping one leg around his waist, she felt the bulky knife at his side. The dim light flickered above them, and he suddenly turned around so that his back was to the wall, and she heard the unmistakable sound of the unzipping of a zipper and the unbuckling of a belt buckle. Sliding down his body, she looked up at him and grinned, though a split second later grabbed the hilt of the knife, yanked it out of the holster, and tried to swerve round for a quick exit out the door.

"Hey!"

Unfortunately, he was faster than she could have ever hoped to be, and she screamed as he slammed the door she had only just managed to get open. Trying to duck under his arm, Ann failed miserably, and screamed again as he tucked an arm under her waist and slammed her back against the door. His hand wrapped around her throat, and she felt him start to compress her windpipe.

"You think you can come back here and try to rob me? Me?!"

"Please," she whispered, her voice strained due to the lack of air, "you don't understand! I need this!"

It actually didn't even occur to her to use the knife on him. It had already been dropped, and her hands were busy trying to loosen his grip on her throat, "He... I need it for him! He's... He's going to hurt Frank, and I need it! H-He wants it!"

His eyes narrowed, "Who? Who wants it?"

She gasped again, trying to get in as much air as she could, and she was starting to see little dots in front of her eyes. Blinking a few times, trying to make them vanish, she managed to get out, "Clown. The clown w-wants it-"

The moment she mentioned a 'clown' – which was really the only physical description she could give the guy from their brief encounter – Gambol dropped her, and she ended up in a crumbled mess at his feet. Her neck throbbed, though it was nice to finally take a deep breath again. Her few seconds of peace were short-lived, and she released a cry of pain as the mob boss backhanded her sharply, his rings coming into painful contact with her cheekbones, "You're working for the Joker?! Are you fucking kidding me?!"

"No!" she whimpered, delicately touching the side of her face as she cowered on the floor, her lip now bleeding, "No! He-"

A kick to the gut shut her up, and she cried out again. Of course this would happen. How could she possibly think that by some stretch of the imagination her stupid plan was actually going to work? Now here she was, broken and bruised on the floor, and Gambol was flipping a shit about some Joker guy. Clearly it was the wrong thing to say, but her brain was barely functioning. What with the alcohol and the new trauma, it was a wonder that she was conscious.

That was about to be remedied, much to her horror. Gambol crouched down next to her, pushing her hair out of her face, "Well, sweetheart, don't you worry. Me and my boys will send you back to your boss soon enough. You'll make a pretty and busted up package, don't fret."

"But I don't-"

Her protests were silenced as he slammed another shoed foot into her ribcage.