If you aren't shakin'...there's something very wrong

Oscar Bailey. 43. Enterprising businessman. Gambler on the side.

[gamblin-boogieman]

thatwretchedsally‌:

Sally smiled at his offer. “I do have your number on my file, yes… but you’re such a busy man and I don’t want to take up too much of your time.” She told him gently, reaching out and squeezing his arm. She let her hand fall back to her side, nodding at his words. “Busy is good! Things have been busy for me as well, but that’s how I like it.” She confessed with a soft chuckle. “I’m sorry I haven’t kept in contact… we still have to make you watch The Addams Family and I simply haven’t had the time.”

He waved away her concern about taking up his time. “Nonsense. I’m in charge of my time, not someone else. I mean it, you need help, you can call me. Alright?” He gave the tip of her nose a small tap, then slipped his hands into his pockets. He shook his head as she apologized. “No need to apologize, Ms. O’Hara. I understand. Busy is good. I don’t fault you for having a successful business. But I do agree, I need to see this movie. Especially if it’s one you’re so fond of.”

[gamblin-boogieman]

caralessthanthree‌:

Cara watched the woman as she went before looking back at Oscar and then at her hand.  “Coward,” she murmured as the dealer called for them to show their hands.  She put down her hand, card by card, showing off a full house.  She took the chips she’d won and pulled them towards herself.  She’d have to play smarter this time if she’d want to drain Oscar for the pennies he was worth.  “Bankhole, asshole, what’s the difference?” she said, fanning her eyelashes at him before sighing, “Look, you’d be my ‘superior’ or whatever.  Isn’t that something?”

He rolled his eyes at her name calling, setting his hand down. He didn’t care that he’d lost, really. He frowned as she confirmed she’d meant Seth. He didn’t like that, her calling Seth and asshole. Whether it was true or not. “Yes, sure. That helps. You’d be listening to me, definitely. Do you think you could handle that, princess? Minding someone else besides yourself?”

[gamblin-boogieman]

thatwretchedsally‌:

Sally sighed quietly as Oscar’s arm wrapped around her, keeping her close to him as Finklestein rolled by. She bit her lip as Oscar looked down at her, catching her lower lip between her teeth at his expression. She missed the security of his arm around her waist, tucking a short lock of hair behind her ear. “Oh, I’m okay Mr. Bailey.” She shook her head. “I just… quite simply, I didn’t want to be seen or talked to by someone.” She expressed, forcing away her worried expression and looking up at Oscar with a small smile. “But how have you been? I haven’t seen you in ages Mr. Bailey, not since the community center opening.”

He tilted his head, frowning softly. He glanced back in the direction Finkelstein went, taking a deep breath through his nose. “Well, if you ever need a body guard for that sort of thing again, I do believe you have my number somewhere, yes?” He didn’t usually offer to be a body guard. Usually it was the other way around. He ignored that thought, instead focusing on her next words. “Ah, yes. It has been a while. Things at work have been...busy.” He lied. The casino had been running smooth as ever, nothing special happening. He’d just lost himself in the haze, really. But he didn’t want to tell Sally that, for some reason. “I’ve been just fine. How about you, dear? How’s things at the shop?”

[gamblin-boogieman]

caralessthanthree‌:

Eventually, it was just Cara and Oscar’s woman.  She upped the bid once more, and eyed Oscar, wondering if he was willing to risk the couple of hundreds that were now at stake.  It was chump change for Cara, but she knew it meant more to Mr. Bailey and those at the table.  “I want in on whatever spooky, shady nonsense you and Mr. Asshole are scheming up,” she said, flickering her eyes at him, “You both have a power around this town.  People are afraid of you and you exert control over them.  Being a high school bitch isn’t cutting it anymore, and I need a new hold.  Consider it an internship.  How to be a small town supervillain.”

Oscar watches the game go on, chewing at the inside of his cheek. He debated for a long moment if this game was worth the money he could potentially lose. He took a deep breath, resting his forehead on the back of the woman sitting on his lap, and gently tapped her wrist. She hesitated for a moment before setting the cards face down on the table announcing her fold before she stood up. Oscar took her hand, kissing the back of it, then let her go. “By Mr. Asshole you mean Seth, yes?” He didn’t like calling Seth by his last name, it felt too formal for whatever their relationship was. “What makes you think I would take an intern over some information I might not even need?”

[thatwretchedsally]

@sunnysidestarters

It was still a gut reaction to try and run or hide when she saw Finklestein in town. He barely left his home after all- only to go find her when she had tried to escape when she still lived there. He even had his groceries and other necessities delivered to his doorstep. At the sight of him on the sidewalk, Sally quickly sidestepped towards a person nearby. “Hi, can you just… stand still for two seconds?” She asked, turning them both so Sally would be obscured by their body. When Finklestein rolled past them and out of sight- where he was going she had no idea, she looked up at the person and flashed a sheepish expression. “Um… I’m sorry about that.” She apologized, wringing her hands together nervously. “Thank you for holding still.”

[gamblin-boogieman]

Oscar looked down as he was turned, recognizing the top of Sally’s head instantly and slipping an arm around her, brows furrowing at her behavior. He looked towards the approaching person, watching as Finklestein rolled by with a curious expression. He’d never met him, but by Sally’s actions he suddenly very much wanted to. He felt an anger bubbling in the pit of his stomach, one that usually showed up when someone he knew had been wronged. But Sally’s voice called him back, and that anger faded as he looked down at her sheepish expression. The arm around her pulled back, a hand settling on her arm. “It’s quite alright, Ms. O’Hara. Are you alright, dear?”

[ofmariesx]

As she always did the weekend of Father’s day, Marie took a ‘vacation’ to the town next to Sunnyside. She’d always proclaim she went there to visit a friend, but in reality she wanted to be somewhere she wouldn’t be questioned for shutting herself inside her room and ignoring the world. It was the one day of the year she wasn’t fully capable of pretending everything was fine. By the time she got back to Sunnyside, she hadn’t quite managed to bring herself out of her sour mood. Sighing a little too dramatically as she was handed the wrong drink order, she turned to the person behind her in line. “You ever just… Have one of those weird days where it seems like life is pranking you?” @sunnysidestarters

[gamblin-boogieman]

Oscar stared down at his phone as he waited for his drink to be announced, adjusting the sunglasses perched on the end of his nose. He glanced up at the nearby voice, raising his head fully once he realized the voice was being directed at him. He hesitated a moment, looking the young woman over for a moment, eyes narrowing as he tried to figure out if he had missed something while he was distracted by the game on his phone. Not seeing anything, he slipped his phone in his pocket, answering her question with a shrug. “I suppose I’ve had a day or two like that, yes. Not recently though.” He finished the sentence with a knock on the wooden counter top, though he figured it was probably faux wood. “What’s gotten you so down, dear?”

[gamblin-boogieman]

lionasshole‌:

Seth chuckled at Oscar’s dramatics. “Maybe I just don’t want to see you come pouting. You look about ten years younger when you do that.” He admitted with an eye roll. Seth glanced down at the pitiful cards in his own hand, not too concerned about losing to the con man. “I’ll do what I can, Oz. I do enjoy a challenge every now and again.” He added to the pot, knowing he was going to lose but also making the mental note of what he’d charge his friend as a fee later.

“Unfortunately Sunnyside’s as quiet as ever. I mean, besides the Sanders case that I won’t be involved in until or unless the SPD gets their shit together.” He raised a brow. “I… Yes, we are friends, I just know we both tend to have ulterior motives. I think that’s what drove us together if I recall correctly.” Something about the other man had always drawn Seth in, Oscar’s antics tickling his fancy and touching his curious nature. “It’s good to see you, Oscar.”

Oscar rolled his eyes. “You’re just jealous because I’m prettier than you, please.” He smiled at Seth’s addition to the pot, organizing his cards in his hand. “Do you enjoy a challenge? Well, then playing here must be very fun for you sometimes.” He chuckles. 

He snorts at Seth’s dig towards the SPD. “If that isn’t the truth.” He grows quiet as Seth talks, thinking over their relationship. He gave a thoughtful hum, “You’re not wrong about that, really. That is what brought us together. But it’s not what kept us together, is it? Be honest, you like spending time with me, don’t you?” He teased quietly, leaning to elbow him slightly, giving him a smirk. He had to put a playful twist on it, feeling...emotions coming up in the conversation. He swallowed at Seth’s confession, nodding. “Yeah...you too, Seth.”

[gamblin-boogieman]

caralessthanthree‌:

Cara wished she could put a name on the high she got from Oscar’s attention.  It was clearly not romantic or sexual, in fact the thought made her sick to her stomach.  Perhaps it was the thrill of doing something bad that sprouted goosebumps along her flesh.  She rolled her eyes as a beautiful woman came to sit on his lap at his simple beckoning.  She eyed the woman quietly, a lump growing in her throat.  Perhaps it was a type of jealousy.  She waved the thought away and focused on her cards, pleased as a few of the men at the table folded.  “I want in,” she said simply.

Oscar caught Cara’s quiet look over the woman in his lap, smirking quietly as he recognized the look in her eyes. He tilted his head as she gave an answer, one brow raising in curiosity. He glanced at the table as a few players folded, giving a quiet laugh as he rested a hand on the back of the woman on his lap, praising her for something that may not have been her doing. Whatever, she deserved it anyway. He’d noticed more than Cara glancing at her since she’d sat down. He made a mental note to give her a bit extra in payment at the end of the night. “In? Into what, Cara? I have a membership for my fine establishment here, is that what you mean?”

[gamblin-boogieman]

drbaileymerc‌:

The doctor wasn’t good at these things, much less accidentally flirting with patients. The blood rushing to his face wouldn’t stop as he felt more heated with every word this man spoke. “Mnngghh” Those are not words, Bailey. Chastising himself for being so awkward he looked the man in the eyes. “I uh…suppose not ha. Your given name is quite nice.” Nodding as he was given permission to touch him, he gently inspected the area. “So I’m assuming this isn’t the reason you came in today? I can carry on with the normal check up but I will tell you I want to do some xrays. This doesn’t feel so great and the bruising is spectacular.” Pulling his stethescope from around his neck, he placed it gingerly inside the man’s shirt, listening to his breathing. “You don’t have to of course, but it’s recommended. Breathing sounds good, thank you.” Wrapping the equipment back around his neck, he reached for the blood pressure set. A gentle hand placed the band on Oscar’s arm and smiled. “But I will tell you it’s most likely broken and we will have to reset it. Or you can let it do it’s own thing. You may have a slightly crooked bridge, but it’s not uncommon in unassisted healing.” Pumping the band, he finished and wrote a few things on his charts. “It may be a little nosy, but how did you come to get this lovely injury?” 

Oscar watched Bailey’s movements, shivering at the stethoscope, though it wasn’t that cold, and breathing deeply. He followed the motions of the visit, muscle memory kicking in though it had been a while since he’d gone to a doctor. He tried to keep his usual face, but the doctor’s further questioning of his nose made him falter. He debated just telling him. ‘I got angry at this fellow I was trying to convince to give me information on everyone in town, most likely including you, so I punched him! To be very fair he was being excruciatingly difficult, no one would have blamed me.’ But he held back. Didn’t want to scare the poor thing, he seemed pretty shaken up by the tiny bit of flirting Oscar had tossed at him. “Just a little scrape, that’s all. Nothing to worry about. Everyone’s fine.” The other guy ended up in the hospital, but he was out now, so. “So there is a way to fix it, then? I would like to keep it from being too crooked. Wouldn’t want to mess up perfection, now would we?” He turned his head to give Bailey a smile, raising his eyebrows slightly. “That would certainly be a crime.”

[gamblin-boogieman]

caralessthanthree‌:

Cara spotted his expression from the corner of her eye, and she felt a quirk at the corner of her lip.  She had an affect on him, and that’s really all she wanted.  She couldn’t pin point exactly why his attention mattered so much to her, but as long as she could get it, she wasn’t going to complain.  She upped her bid.  “Information for you, if you want it,” she said, still playing coy.  The giddy feeling over knowing something he didn’t washed over her.  Before anyone else could decide whether or not they were willing to match her bid, she tossed a few more chips on the pile.  “Information on a Mr. O’Malley.  I know he’s a point of interest for you.”

He tilted his head, turning away from her to mess with the cards in his hand. He wasn’t too invested in what Cara was there for, until she dropped the bomb. Information. Shit, she’d got his number. He sighed quietly, gesturing for one of the women walking around the floor closer. He handed her his cards with a smile, a silent message of ‘Here, you play for me.’ as he patted his knee. He rested a hand on her hip as she settled on his lap and kept his part of the game going, turning his full attention on Cara. “Alright. I’m not entirely uninterested.” He glanced at the game, going without his influence now, realizing how that sentence sounded. But he didn’t waver. “What’s in it for you?”

[gamblin-boogieman]

lionasshole‌:

“I can certainly attempt to do some damage control, though it’ll cost ya extra for the extra effort,” he teased. He glanced at Oscar’s cheating schemes in the form of the ace in his sleeve. “Y’know, this is why I hate playing with you,” Seth laughed. “I’ll do my best to persuade our new friend. I know it’ll be beneficial, somehow he manages to get himself all the way around the whole of Sunnyside.”

Seth didn’t understand those who socialized with everyone they met, it seemed exhausting to say the least. He preferred the quiet, especially since he was working so closely with The Pride Corporation now behind the scenes while his good-for-nothing nephew lollygagged around town as though he had no responsibilities like a child. Spoiled rotten and deserving of nothing. Seth couldn’t help but be bitter.

“I do hope this wasn’t the only reason you called me here.”

“I would ever so appreciate it, Seth. Tack on whatever extra you like, you know I’m good for it, darling.” Oscar put a bit of a posh twist to his accent as he reached and gave Seth’s shoulder a squeeze. He rolled his eyes as Seth called out his cheating, dropping the changed voice. “Oh, please. You know I’m like this, yet you keep playing with me. I don’t think you hate it as much as you like to complain.” He nods as Seth agrees to help with the O’Malley situation, quietly rearranging his hand. “Good, good. Yes, that’s why I wanted to go after him. Especially considering he’s somehow found his way into Bonfamille’s bed. Having him in that neighborhood will be very nice, I think.”

He chuckled as Seth mentioned why he called him there. “It was a big part of it. It was also a sort of...check in? See how things are going with you, if there’s anything interesting happening. Any new things to drink about, either good or bad. Can I not just want to hang out with you from time to time, Seth? We are friends, aren’t we? I think that’s what friends do, if my memory is right.”

[gamblin-boogieman]

ohtcmmy‌:

Tammy’s eyes narrowed for a moment at the males first question. “Maybe I don’t.” She responded, shoulders lifting in a quick shrug. “Well, you’re not really missing out. It’s.. strange. Not a good version of the sweet and savory thing.” His next words caused her to let out a sigh of relief. “Lit is almost as bad as, uh, yeet, is it? Lit at least makes sense. Kids these days are coming up with the dumbest things.”

He gave a chuckle, “Well, that’s good to know. I’d hate to be missing out on something.” He took another look over the menu, honestly at a loss. He wasn’t lying when he said he didn’t eat pizza often, but he couldn’t be bothered to cook dinner that night. He was very low on ingredients, but he also couldn’t be bothered to go grocery shopping. So something fast and easy it was. “God, don’t remind me.” He groaned as Tammy started talking about more lingo. “I absolutely abhor ‘yeet’. It’s a ridiculous word. What does it even mean? It’s just a noise when you throw things. You’re right, lit actually makes sense. I don’t know what’s wrong with the word cool, but eh.” He gave a shrug, sighing. “Kids, y’know?”

[wxhwtne-deactivated20200528]

Dimitri had walked away from a deal with a smirk on his face as he counted the bills in his hand. Stowing them into his wallet and shoving it into his back pocket, he looked up at the face in front of him. “What a gorgeous face on such a beautiful day. And who am I supposed to thank for that gift?” @sunnysidestarters

[gamblin-boogieman]

Oscar caught sight of Dimitri’s smirk, recognizing the expression of a deal gone well. He watched him counting the money in his hand, moving into his path quietly and waiting for Dimitri to notice him. Dimitri’s words brought a smirk of Oscar’s own to his face. “Well, then! Aren’t you bold?” He extended a hand toward him, smiling widely. “Oscar Bailey.” He leaned in closer, lowering his tone. “That looked like it went well. What was that all about, hmm?”

[gamblin-boogieman]

talkingxfishbone‌:

He tried to keep the fear from his face. He really, really did. But he knew it was probably a failed attempt. Oogie looked too smug—but then again, when did he not? He knew that anything the man was involved in was something Hadley wanted to stay far away from, but here he was, now indebted to the creepy guy. “Um, yeah, of course…..I’m kind of useless though.” He nervously rubbed the back of his neck.

Oscar gave a slow smile, the fear on Hadley’s face and in his actions giving him a boost. He clicked his tongue as Hadley called himself useless, slipping his hands into his pockets.  “Oh, nonsense, Hadley. I’m sure you could be plenty useful, once you apply yourself. Don’t you worry, dear, I’ll find something that will suit you just fine...”

[drbaileymerc]

@gamblin-boogieman 

Just a normal day in the office for Bailey, fixing up the wounded and trying to keep sane while also fending off the hungries. The doctor was at the tail end of a twelve hour shift, and everything seemed to be coming to an uneventful close. That was until he was shuffled into his last check up of the day. “Hi, I’m Dr. Mercado and I’ll be doing your check up. Your chart says we haven’t seen you in a while, routine visits are important to maintain a healthy lifesty-” pausing as he looked at his patient’s information. “Uh, Mr…Bailey?” Inquisitive eyes met the other’s, thinking aloud something one should definitely keep inside one’s very professional and lawsuit vunerable head. “Funny, that’s my first name. If we got married I’d be Bailey Bailey. Hah.” An awkward shift, and then a cough. The guy was handsome, debonnaire as some would call it. ‘His cheekbones could cut vibranium’ Bailey allowed a thought that Fred would most certainly be proud of before remembering the strange comment he’d made and broke into a furious red blush.  “Hm.. I… well. Can I take a look at that bump on your nose? It’s pretty swollen, and might be broken sir.” Bailey got closer to the man and pulled up a stool, swiviling on over next to the exam bench. “Someone gotcha good,didn’t they? On a scale of one to ten can you tell me how much pain you’re in if I touch it?” he reached for the other’s nose, looking over for approval . 

[gamblin-boogieman]

Oscar sat on the exam table, kicking his legs slightly as he waited. He took a deep breath, leaning his head back to stare at the ceiling. He’d counted the tiles once already, and didn’t really feel like doing it again. He really could use a cigarette, he even reached up to pat at his jacket pocket to feel the pack there. He’d been putting off this visit for longer than he needed too, he knew that, but he just hated doctor’s offices. He hated the clinical feel and the awful lighting. That and the memories that it brought crawling to the back of his mind. Just as he was about to hop off the table and call the whole thing off, the door opened. He sat up straight, putting on his usual smirk as he listened to Dr. Mercado’s opening lines. Oscar’s smirk grew when Bailey noticed his last name, the marriage comment making him laugh quietly. “That would be quite an interesting married name, Doctor. Though I think that could be avoided. Oscar Mercado.” He hummed in thought. “That has quite an interesting ring, don’t you think? Not quite as classic as Oscar Bailey, though.” He gave Bailey a smile, which fell as he pointed out his nose. He frowned, reaching up to touch at his swollen nose, flinching. He looked up at Bailey, glancing at his reaching hands. Taking a deep breath, Oscar looked around the room. Everywhere but at Bailey, and gave a very small nod. “Very well then, go on Doctor. It’s...about a seven, I suppose. When I touch it, that is.”

[gamblin-boogieman]

caralessthanthree‌:

Cara had a dirty secret.  When Cara turned eighteen, she downloaded an online poker app and spent more money than she would admit playing.  She didn’t have any skill in the game, but she blamed her deficit on not being able to see the other players face to face.  Here, in the flesh, it was much easier to read the other faces at the table.  She quietly played, looking at her cards, face completely blank.  Usually, she wore her heart on her sleeve, but now she seemed to be made from ice.

“You’ve managed to bring style to what’s essentially a finished basement.  I’m impressed,” she hummed, eyes looking at her cards, as she tossed in a number of chips.  Her dark eyes flickered towards him and then back to her hand, decidedly not letting anything show.  “Information,” she said simply before holding her hand up and snapping at one of the waiters as they passed until they stopped.  “Gin and tonic, heavy on the gin.”

Oscar watched her face as she looked over her cards, narrowing his eyes a bit at her blank expression. That wasn’t like Cara. She usually was so expressive and emotional, leaving everything on the table for him to see. Now she kept it all back, which made him extremely curious. 

He rolled his eyes at her words. There she was. Couldn’t have a conversation without insulting something, could she? His ears perked when she mentioned information, and he turned his head towards her again, both eyebrows raising in curiosity. “Information, huh? What for?” He caught the eyes of the waiter, giving them a small nod to order his usual drink. “What sort of information?”

[gamblin-boogieman]

talkingxfishbone‌:

Hadley, already crouching to gather everything he’d dropped, flinched as he saw the phone clatter to the pavement. He glanced up, ready to apologize profusely—and quickly looked back down. Gods, why did it have to be Oogie? The man had scared him every since he was a kid. He stood slowly, scared to see how bad the damage was. His heart sunk when he saw the spiderweb of cracks in the glass. “Oh, god, I’m so sorry, I didn’t….I can pay you for that,” he said, swallowing thickly. He couldn’t afford it, and there was no way he could ask his dad for the money. But he couldn’t just leave the damage without doing something. “I, uh…” He leaned down and grabbed a pen—one of his favorites, now scratched, which was nothing compared to the damage of Oogie’s phone. “That’s everything. I’m so sorry…”

Oscar raised an eyebrow as he watched Hadley glance at him and then look down again. He saw the recognition in his face. Ah, so he knew who he was. Good. Oscar smiled slowly as he watched the fear in Hadley’s face as he stood and caught sight of his phone. His offer to pay made Oscar chuckle, rolling his eyes. “Oh please, don’t bother. I can easily get a new phone. No need to worry your head over it. Just...consider this an IOU, how about that?” He tilted his head, smirking. “I’ll just uh...let you know when I need a favor.”