Work Header

The Donna

Work Text:

REGINA stared coolly out the window. Behind her, Horatio blubbered and sniveled excuses. He had lost $100,000 of her money, and while normally not concerned with such a trivial amount, Regina had never cared for Horatio, and now was going to make him pay.


“Donna Regina… You must understand! I could not defend myself! The men… The men… They surround me!” Horatio sputtered in broken English.


“Shut up you fucking idiot!” Regina hissed, tired of his incessant whining. “I’ll tell you what. You have four hours to find ‘the men’ and get my money back or you’ll regret it.”


“Donna… I cannot find them. If it is my life you want in exchange for my… my mistake… then please… I do not know who they are or where they are from. I offer my life for my mistake.”


“That’s hilarious!” Regina said with a hearty laugh. “Why would I do you the favor of killing you? No. That’s too easy. You lost my money, so you get to lose everything. I won’t kill you. No. I’ll let you live so you can watch your wife and son die. And then, I’ll let you live the rest of your pathetic life alone, remembering the time ‘the men’ cost you everything you hold dear. Don’t make me destroy your happiness. Get the fuck out of here and find my money!” Regina spat. Horatio’s wails doubled at her words. Regina did not get to be the head of the Boston mob by bluffing about her intentions, and the henchman had no doubt that she would absolutely carry out her threats. The Donna’s guards drug him from the opulent office, his screams echoing down the hall. Catching the door on its swing back, her top lieutenant entered, chuckling at the unfortunate fate of Horatio.


“Come now, Regina… His son?” Cristiano scolded. The relationship between him and Regina appeared casual and friendly on the surface, but beneath that was years of trust, friendship, and respect. Cristiano had been by Regina’s side in her somewhat bloody ascension to the top of the Boston Mafia family, and there was no one she trusted more.


“I had to make a point!” Regina put on an innocent face and stirred her tea, sliding the silver spoon between crimson lips when she was done. “Besides… I spent almost the whole day without making anyone cry. I was beginning to feel obsolete.”


“Well, you do have a knack for that, princess.” Cristiano teased, pouring himself a cup of tea.


“Princess… Ugh. I like to think I would be a queen.” Regina snipped back, musing on life as a monarch with absolute power. “Yes, I think I would quite like that. Do we have plans this evening?”


“Yes. We need to go and check on the Southside casino. There’s some new dealers there, and we need to make sure our interests are being upheld.” Cristiano confirmed, consulting his phone for their schedule.


“I do love babysitting.” Regina said, rolling her eyes. She stood and smoothed her impeccably crisp white suit. She cracked her neck, trying to loosen stiff joints. She didn’t like the soreness and stiffness she had been feeling lately, the reminder that time was the only thing she couldn’t control. “We’ll stop at the docks while we’re out there. You know I love visiting those boys.” Regina said as she gathered a small clutch and strode from the office, her tall stilettos clicking on the tile floor.




Emma nearly fell as her arm was grabbed and she was yanked into a corner.


“Listen. I know you’re new, but we just got word that a VIP guest is on her way, and I want you to take care of her.” Her manager growled. Not a pleasant man, Vin was a hulking brute who controlled the casino with fear and intimidation. Emma had no doubt that he had connections to the mafia, but despite his demeanor, he took care of his employees. She’d been working at the casino as a cocktail waitress for just over a month, and in that time he’d thrown out quite a few patrons who were looking for a “hands-on” experience.


“Alright. Anything I need to know?” Emma asked, regaining her composure.


“She comes in with a big group of guys. No tab, don’t ring anything in. We’re setting up a bottle service for them. Keep your wits about you and mind your distances… I can’t protect you from her guys. Or her.” Vin added with a grin. “She likes pussy as much as any man. Fucking hot bitch.” He grunted.


“Alright.” Emma said, a little repulsed at the expression on Vin’s face as he told her about the woman’s proclivities. “I’m going to go freshen up then.”


Half an hour later, Regina and her entourage entered the casino. Vin greeted them at the door, doing his best to stand up straight and suck in his massive gut. Emma spied on them from the entry to the VIP area, chuckling at Vin’s attempts to square up to the woman’s bodyguards. The casino boss didn’t stand a chance. All of Regina’s guys were at least 5 inches taller, 5 years younger, and 50 pounds leaner than Vin. They made their way across the bright casino floor, and Emma observed as Regina scanned the activity around her. Emma decided that Regina definitely had some sort of vested business interest in the casino. She wasn’t casually people-watching; She observed the levels of drinks, watched a few waitresses making change, and scanned the bar, silently monitoring the bartenders as they made a few drinks. Satisfied, she continued towards the VIP area, Vin chatting the whole way and no doubt telling her about the casino’s numbers.


“And this is Emma. Emma will be taking care of you this evening. Emma, this is Regina. Please make sure that she has anything she wants.” Vin introduced as they approached.


“My pleasure.” Emma said, softening her eyes and lingering on Regina’s dark brown irises. Regina was truly stunning, and Emma figured that, based on what Vin had told her earlier, a little flirting wouldn’t hurt. “We have a full bottle service provided for you, and I will be happy to make you whatever libations you desire.” Emma added. She could tell from the flicker in Regina’s eyes that the woman enjoyed the power play. Emma smoothed her jade green dress as she waited for Regina to decide her drink.


“Bourbon. Neat.” Regina finally said, the words rolling off her lips. Emma nodded and crouched, the slit in the dress falling open and exposing soft, lightly tanned skin. Regina took in the view as Emma deliberately and slowly poured her bourbon, enjoying the interplay between the two of them. She was positive that Emma was running a gambit, but the brunette decided she didn’t care. Emma was sensual and sexy, and Regina was happy to have her presence.


“Hey sweetheart! How about a few for us?” One of the massive men jeered. Emma fired him an icy stare and her lips curled to a wicked grin.


“You’ll have to ask your boss. I’m at her service this evening.” Emma replied, putting him in a position of not being able to win: If he argued, he was disrespecting his boss. If he conceded, he was letting a cocktail waitress tell him what to do. He snarled at Emma before he shrank back into his seat, ending the brief standoff. Regina laughed and slid down the large couch, displacing another bodyguard.


“Sit, I’d like to get to know you better.” Regina said, tapping the couch next to her. Emma accepted the invitation, crossing her legs and again allowing the light green dress to show copious amounts of skin.


“What would you like to know?” Emma asked, tossing her hair and letting the blonde tendrils cascade over her shoulders.


“First, I’d like to know what you drink.”




The hours passed quicker than Emma could keep track of, as did the glasses of bourbon. She found Regina fascinating, and easy to talk to. It wasn’t long before her playful flirting had given way to genuine interest and engaging conversation. When Emma excused herself to the restroom, she was shocked to see that she had spent almost 3 hours completely rapt in conversation with the beautiful brunette. Her shift was supposed to end at 3am, but she had a feeling that despite it being 2:30am, she was at Regina’s service until the woman went home. She took advantage of the break to stretch out stiff muscles, touch up her makeup, and spray a bit of perfume. Satisfied, she returned to the VIP area. Regina was standing, and some of the bodyguards were starting to make their way to the front of the building.


“Calling it an evening?” Emma asked, surprised that she was lamenting the other woman leaving.


“Not hardly... I think I’d like to play some cards.” Regina mused, again surveying the casino floor. Despite the late hour, the venue was still crowded, and Regina seemed satisfied to see the number of people still playing games and spending money. As if on cue, Vin appeared out of nowhere.


“We have the High Roller room ready for you, ma’am. Do you have anyone in particular you would like to play with, or would you like me to select some of our high rollers who are here?” Vin offered, showing Regina and her remaining bodyguards to the private playing table.


“I want to play with her.” Regina said, turning to Emma and raising an eyebrow.


“I can’t possibly afford the buy in…” Emma said, flattered at the invitation.


“I’m sure we can figure something out. Cristiano, you may go home. We have a lot of work to do tomorrow. I’ll call Sal when I’m ready.” Regina instructed coolly. One of the men nodded and then accompanied the others out of the casino. Vin swiped his access card, granting access to the small, intimate room with a few couches and a beautiful card table in the middle. Emma had heard of the High Roller room, but had never had the privilege of entering.


“$500,000 in chips, Vincent.” Regina said, seating herself at the table and not looking at the man. Vin scrambled away to retrieve her chips, the door clicking behind him. Emma realized the room was soundproof, for as soon as the door shut, a pin drop would have been deafening in the silence.


“So, Emma…” Regina said coyly, running her fingers over a deck of cards. “Do you play poker?”


“I.. Umm.. I do… But like I said… I don’t have that much cash… I barely have $500, let alone $500,000.” Emma said, blushing and feeling uncertain for the first time all evening.


“I know. What do you say we raise the stakes even past that?” Regina asked, toying with Emma and wearing a Cheshire grin.


“How much higher do you want them to go?” Emma asked, nervous at the brunette’s predatory tone.


“No money. We play for… Clothes.” Regina revealed her plan. “You win, you keep your clothes and my cash. I win… Well…” Regina mused, her fingers still running over the deck of cards. Their conversation was interrupted by Vin re-entering the room, carrying a case of chips.


“The dealer is on his way.” Vin said as he started setting out the stacks of chips. He had sweat beaded at his receding hairline, and Emma decided she enjoyed seeing the surly man uncomfortable in Regina’s presence.


“I’m sorry, did I ask for a dealer?” Regina said, casting a wary glance in Vin’s direction.


“I… ahhh… No. No you didn’t.” Vin finally conceded.


“I didn’t think so. That will be all Vincent. We don’t want to be disturbed.” Regina waved the man away and returned her focus to Emma. Vin scowled at the second use of his whole name, and Regina’s dismissive attitude. Begrudgingly he left, the silence returning to the room.


“So, Em-ma…” Regina continued, saying Emma’s name slowly and deliberately. “Shall we?”


“You know… You’re on.” Emma said, seating herself across from Regina.


“Good. I’m sure this will be one of those evenings in which you wish you wore a pantsuit and not a dress.” Regina grinned, smug in the knowledge that the odds of winning were stacked in her favor.


“We’ll see… Deal.” Emma said, her adrenaline pumping at the challenge. Regina pursed her lips and nodded slightly as she shuffled, cut, and then shuffled again. She dealt five cards and laid out the river. Emma discarded and drew, Regina discarded and drew.


“How ironic… Straight.” Regina said, smugly laying down her hand.


“Not bad, but you’ll have to do better than that… Full House.” Emma said, grinning and laying down her own cards.


“Impressive.” Regina said, standing and sliding out of her white blazer. She cast the coat aside and slid her cards to Emma, who shuffled, cut and shuffled again.


“Shouldn’t I be naming what gets removed?” Emma asked, throwing caution to the wind.


“My game, my rules.” Regina shot back, leaning against the back of the chair and casually crossing her legs. Her white button down was crisp and slightly sheer, and fit her perfectly.


“Fair enough. Good luck.” Emma said, dealing the cards.




“Emma, I’m beginning to feel like you’re hustling me.” Regina said. She had lost her blazer, vest, and shirt in record time, and Emma sat across from her, fully clothed.


“Beginner’s luck… Did you want to stop?” Emma asked, trying unsuccessfully to hide a grin.


“To the contrary. I’m not one to back down from a challenge.” Regina curled her lips into a feral grin.


“Alright… But I’m not the one about to lose my pants…” Emma mused. The low lights made Regina’s curves even more dramatic, and Emma was having a harder and harder time concentrating on their game. She let out a sigh as she dealt and cut the deck, trying to settle her nerves and stay on the upper hand. Regina was a skilled poker player, and Emma had won the last hand based on sheer luck.


“Ha! Four of a kind!” Regina gleefully exclaimed. Her glee was short lived as Emma laid down her hand.


“Royal Flush… Hearts.” Emma said with a grin. Regina stared at the cards, realizing that she had been bested yet again, and that Emma was simply a better poker player than she was. Regina stood and stepped to the bar, pouring herself another bourbon and savoring the spicy flavor. She had never felt angry about a poker game, but she also usually didn’t lose. The bourbon softened her edge, and she turned, locking eyes with Emma as she stepped back in front of her seat. She traced her over her olive skin, sliding her fingers into her waistband and seductively unhooking the clasp and sliding the zipper down. She caught her bottom lip in her teeth as she slid the white pants over her hips, exposing her black lace panties. The hungry look in Emma’s eyes told Regina all she needed to know: That Emma held the same tendencies as she did. Regina continued the slow striptease, rolling her hips as she pulled the pants down to her thighs before sitting down and  placing one leg on the table, her silver stiletto flashing and sparkling as it caught the light. Emma’s eyes swept down the smooth curves and olive skin, taking in the breathtaking woman before her.


“Your deal, ma’am.” Emma said in a breath just above a whisper. Regina may have been skilled at poker playing, but she was a master of seduction.


“How about we change the game a bit?” Regina suggested, her eyes dark and intense. “One card pull. Winner takes all.”


“You’re on… Aces high.” Emma said, shuffling and cutting the deck. She spread the cards in a graceful arc and leaned back, waiting for Regina to choose her card. The brunette pondered for a moment before sliding a single card from the arc and flipping it over to reveal the ten of spades. Emma swallowed before selecting her own card. Regina easily held the blonde’s gaze as Emma flipped her own card over, revealing the Jack of diamonds. Regina huffed and flicked her hand, scattering cards and cash across the table.


“Double or nothing?” Emma asked, feeling exceptionally cocky after a quite fortuitous evening.


“Alright.” Regina said, leaning forward and collecting the cards. She shuffled and cut the deck before spreading the cards in a long S curve. Emma studied the cards before sliding out a card and flipping it. The eight of clubs wasn’t a strong pick, and Regina beamed a full smile as she leaned forward and selected a card. She lifted the corner and raised her eyes to Emma’s.


“I’ve always dreamed of being a queen.” Regina said, flipping her card to reveal the Queen of hearts.


“Well played, Madame.” Emma said with a smile. She had no idea what Regina had in mind as a winning prize, but she looked forward to finding out.


“Indeed. Perhaps I should stick to games of luck and not skill.” Regina mused. “Now then… I believe I have won an article of clothing.” She said, smug in her clutch time victory.


“I believe you have.” Emma said, standing slowly and stepping between Regina’s legs. The brunette watched as Emma teased her fingers slowly up her stomach and between her breasts, delicately dancing over her neck before undoing a single clasp, allowing the soft green garment to slink to the floor. Regina broke their easy stare, allowing her gaze to travel down Emma’s toned arms and stomach. She watched as the blonde’s nipples pointed, reacting to the cooler temperature and the heightened tension in the room. A bra wasn’t the only underwear that Emma had neglected to wear, and it took all of Regina’s self control to keep her hands on the arms of the chair.


“Well played. Very well played.” Regina said, breaking the silence. Her eyes were dark with desire, but she showed restraint, allowing Emma to make the next move. Emma stepped out of the dress, which had piled on the floor. For a split second, Regina saw uncertainty flicker in the light eyes. Regina stood, her own pants falling to the floor. Leaning close to Emma, she brushed her crimson lips across the blonde’s neck and shoulder. Emma moaned softly, relishing the feel of Regina’s advances. Regina grinned as she continued, finding no quarrel from Emma. Emma slid onto the card table, pushing aside chips, cards, and money as she laid back, pulling Regina on top of her. Still grinning, Regina pushed her lips against Emma’s, and the blonde again moaned as their tongues danced over each other. Regina’s hands skimmed over Emma’s body, enjoying the way she moved and reacted to her touch.

“I want you.” Emma whispered, grinding against Regina’s hips. Regina was happy to oblige, and left a trail of kisses down Emma’s naked body. Emma sharply inhaled as Regina’s mouth found her center, her tongue sliding over her and causing her body to quake and arch. Regina held Emma’s hips firmly, feeling the blonde push and rock against her as her pleasure mounted and peaked. Smiling wickedly, Regina slid two and then three fingers inside Emma, curling up and enjoying the way she reacted to the pressure. Regina’s tongue stayed on Emma’s clit, teasing the bundle of nerves and coaxing rolling orgasms from her. Emma grasped Regina’s hands, feeling her body wear out and losing control of her motions. Regina continued, unfazed by Emma’s shaking legs and increasingly loud moans. Mustering her last bit of strength, Emma slid back, gasping for air and covered in a dewy perspiration. Regina took the hint and kissed the inside of Emma’s thigh before standing, her fingers still dancing over the blonde’s skin. Emma quivered at her touch, a soft smile across her lips. Regina coyly licked her fingers, savoring the taste that lingered there. The brunette turned her head, softly popping her neck and releasing the tension that had built in her muscles during the encounter.


“What about you?” Emma asked, regaining her senses and realizing that Regina was getting dressed.


“Next time, dear. Next time.” Regina said, curling her lips into a smile. “And until then, I’ll be looking forward to finding out if you’re as good with those lips as you are with cards.” She added, softly kissing Emma, who was still a little dazed by the entirety of the night’s events. Regina picked up a card and, retrieving a pen from the table, wrote her number on it. Emma grinned when she flipped the card over to reveal its face.


“Nice… Queen of hearts.” Emma chided.


“Of course.” Regina said, kissing Emma once again, her finger lingering under the blonde’s chin as their mouths met. “Until then.” She said over her shoulder as she sauntered out of the high roller room, slipping out the door and into the casino.


“This… This is gonna be a problem.” Emma muttered to herself as she pulled her dress back on and fastened it. Just as she did, Vin burst into the room.


“Holy shit, what happened in here?!” He asked, scanning the chips, cash, and general disorder of the room. Emma grinned mischievously before answering him,

“The Donna won.”