Lucky Fives

Luke was feeling lucky. He dusted off his navy suit and admired himself, winking at the mirror. Then, he was off to the Strip.

Randomly, he chose a casino, traded in his $200 for chips and ambled up to the Black Jack table. It was his night, and before long, he hit $1000. He was buzzing -- just a couple of games of poker couldn't hurt. It didn't. He was still raking in the chips, and it was early.

He didn't notice her when she sat down. But when she called his bluff, and he lost, he looked at her. She must be about ten years older than him, maybe 35. Luke thought she looked gorgeous in her red dress, brown hair curling down her shoulders. The woman caught his eye winked. Luke smiled. He still had a lot of chips. He'd wink back when he beat her.

But hand after hand, she reduced his stack of chips. He was down to $500 and promised himself this was his last hand. He peaked at the cards; a pair of jacks. He suppressed his smile. At least it was going to be a good last hand.

He eyed the lady opposite it him, and she smiled at him. The flop came out--the jack of hearts, three of spades and five of hearts--he had to suppress his grin even more. There were still a few people in, so he raised his bet. The turn was the five of clubs. Even if someone did have a five, he was still in for the win. He raised his bet again.

Everyone but the women opposite him folded. He looked at her -- she must have a five or trying to bluff me, he thought. He had her this time. Maybe he would go chat to her after this hand. She had been giving him the eyes.

The river was just the queen of hearts, and he let himself smile. Then, she raised the bet to $500 -- all in for Luke, but he was confident and met it. He flipped his pair of jacks over, thinking about want he might buy.

The woman revealed a pair of fives. Luke stared in horror, sickness spread up this throat, and she grinned at him. He turned, left the table, and slowly dragged his feet to the exit.

He was almost at the doors when a hand came down on his shoulder.

"Hey, pretty boy." It was the woman in red. Luke gulped -- he didn't think he could muster his charm to speak to her. But he took and big breath.

"Lucky fives," he said as he turned to look at her. She stood a little taller them him, in her heels. Even in his despair, he glanced down at her body and then back into her intense eyes. His stomach stirred. He was very attracted to her.

"You lost big to me -- about $2000, I'd say."

"$2500."

She pulled a face and then asked, "Would you like to earn it back?"

"Oh, um, no thanks. I don't want to lose more money." Luke tried to turn again, but her hand was still firm on his shoulder, nails slightly digging in.

She laughed. She was cute, and her grip on his shoulder made Luke think she might be his type.

"Oh no, silly. A game that's just you and me. You do what I say and want, and I'll give you some chips back."

"And what do you want?"

She lifted her hand to his face and trailed her finger over his lips. Then down to his tie. "Ah, well." Her fingers continued down, tickling his chest, then his stomach, hovering just over his belt. "That would ruin the game." Luke felt his dick flush and his stomach flip. He looked at her and nodded.

"Excellent. For starters, why don't you go get me and yourself a cocktail." She thrust a $50 chip into his palm. "And keep the change. I'll be at the same poker table."

Luke watched her ass as she strode off. Maybe tonight would not be such a waste. He walked to the bar and grabbed a menu. It all looked fancy. He scanned the menu. If he got a U'Luvka martini and a twist old fashioned, it would cost him $42. He didn't want her to think he was cheap. He got the two expensive cocktails and tipped. Then he pocketed the $4 worth of chips left.

Luke found the woman at the poker table, mid-hand. She had nothing. But she bet big and the people around the table folded.

She looked up at Luke, "Shall we go play a game of luck?"

"Whatever you want, Ms..."

"Marianna, but you will call me Ma'am. And your name?"

"Um... err... Luke... Ma'am." Luke mind fluttered. Could she be a Domme? Or just a woman enjoying some power? Either way, Luke wanted to play along.

"Okay, Lukey. Let's go play roulette."

She took the martini off him and took a sip.

"Oh, good choice." She flicked a $2 chip at him then strode ahead. Luke hurried after her through the crowd of people. She stopped at the roulette wheel, pulled a $5 chip out of her pocket and rolled it over her fingers.

Then she whispered in his ear, "It's yours if you sit on my lap while we play." She sat down and patted her lap. Luke smiled. He was going to win her game, and he was going to like it.

Luke sat down, and she rested her hand on his thigh. He felt his cock begging for attention, slightly filling his boxers. A few of the other players looked at him strangely, but Luke didn't mind their eyes.

"Comfy?"

"Very, Ma'am."

"Place your bets, folks!" The dealer called.

Marianna handed $50 to Luke. "You choose, sweetie." Luke chose red. The wheel spun. Red. It seemed like Luke's luck was back.

"Lucky Lukey," Marianna said as she reached for the winnings.

Luke felt Marianna's hand creep up his trousers. She gave him another chip to bet. Then whispered, "If you don't draw attention to us, I'll give you a little reward." Luke gulped as he bet on red again. Marianna's hand was over his crotch, slowly rubbing up and down. His cock strained against his tight trousers.

The dealer spun the wheel. Luke fixed his eyes on it. He shifted on Marianna's lap, desperate to stay still and quiet as she stroked his semi-hard cock.

The wheel stopped on black. Marianna's hands fell away, and Luke was left wanting more.

"Double or nothing?" Marianna whispered, "Make a noise this time, and you lose what you just earned." She gave him another chip. He placed it on the red five and said, "Lucky five, Ma'am." He felt her smile behind him.

The roulette wheel spun. All eyes were watching it. Marianna wasn't doing anything, and so Luke watched the wheel slow. Could it? He thought. It ticked closer and closer to the red five.

Luke yelped. Marianna had managed to sneak her hand into his pants and grab his balls tight. Her hand was in and out in a flash. Luke sat perfectly upright in shock.

"Yes!" Marianna shouted, "Lucky fives."

She pulled in her chips. "Come on, Lukey, let's go."

As he got up, she squeezed his ass. Embarrassment and shame flooded over Luke. But his cock was still excited.

She took Luke by his hand and led him through the casino into the hotel, right to the life.

"Did you have a fun evening, Ma'am?" The lift attendant asked as she pressed the correct floor.

"It's just starting," Marianna said.

"Ah, very good." The women eyed Luke and seemed to approve.

The lift zipped up, and Marianna led the way through the corridors to her room.

Luke's jaw dropped. It wasn't a room, it was a whole massive suite, and it overlooked The Strip.

"You are loaded," Luke managed.

"You are loaded, what?" Marianna raised an eyebrow at him. For an instant, Luke was confused.

"Oh, sorry. You are loaded, Ma'am."

She flicked a chip over her knuckles, "Much better. Now strip."

"What?"

"Strip."

Luke looked at her as she sauntered over to her private bar. She faced away, her hand trailing along the colourful bottles.

"Don't make me ask again, Lukey."

Timidly, Luke slid out of his jacket and slowly unbuttoned his shirt. Marianna had turned and was looking at him with hunger. He looked back at the floor.

"You have nothing to hide. I already felt it all." She laughed and pulled out a bottle. "It's not bad."

Luke wanted to shrink away, but somehow, his fingers found his fly. Slowly, he unzipped it and pulled his trousers down. He was hyper-aware of her gaze as she shook the silver cocktail shaker.

"Good boy. One layer left and then a drink for the nerves." She poured out two martini's and held a glass up for him to see.

Luke pulled his underwear down, and his semi-hard dick bounced out. He stood, feeling a mixture of shame and lust.

"Come here." He walked over. Marianna handed him his drink, and he gulped it down. The liquid made his throat tingle, and Luke found some confidence in his nakedness.

"Kiss my shoes."

Luke didn't hesitate and fell to his knees. He kissed the pointed tip of her heels, then the arches and finally the heels.

"Open your mouth." Luke opened his mouth. Marianna shoved the end of her shoe in Luke's mouth. He let out a moan, and Marianna's eye burned into him. She kicked off her other shoe and rubbed her foot up and down Luke's swollen cock.

Luke started grinding against her foot, almost forgetting he was meant to be kissing her other foot.

"Concentrate." Luke refocused on her other foot. He was on the edge of orgasm now, but he held on, not wanting to come too soon. Marianna stopped and looked down at red-faced Luke.

"What a perfect little slut I found myself." She flicked a chip at him.

He had forgotten all about the promise of chips and felt like he was in heaven. Marinna stood up.

"Time for another game." She grinned. "It's simple. I will rub your dick for 20 minutes. If you don't come, I will give you $100." Luke was already on edge. He couldn't hang on for 20 minutes. He must have looked unsure, as Marianna added. "You can tell me to stop four times. And I will stop for 30 seconds and then continue."

Luke still didn't think he could. Luke mulled it over in his slightly hazy mind. He had nothing to lose anyway; he either came or got $100.

"I'll make myself another drink while you calm down a bit. And then we can start." She gestured at his erection. Luke fanned himself, trying to calm down. But his erection wasn't going anywhere. He looked over to Marianna, who was pouring out her drink.

"Lie on the sofa." Luke lay on the sofa. Marianna stood over him.

"You are such a pretty boy." She stroked his face gentle, and Luke felt torn between hiding his face or pushing it into her hand. But before he made a decision, she took his cock and slowly started rubbing it. Her other hand trailed down to his stomach. Luke turned his thoughts away from the scene. But Marianna grabbed his face and turned it to her.

"Look at me while I do it." Luke held her eye contact. It felt like she was burning right through him. He wanted to look away. He found himself moaning as she stroked his dick. For a second, he forgot the game and let his hips buck into her hand. He was going to come.

Just in time, Luke shouted, "Stop. Please." Her hand lifted away, and Luke closed his eye and breathed heavily.

"14 minutes to go." The 30-second break passed too quickly, and Luke was still incredibly sensitive when he felt Marianna's hand return to his pulsing cock. He groaned, and Marianna laughed, starting all over again.

Luke held on as long as he could. But Marianna knew what she was doing, teasing the tip and then giving him long, firm strokes. He wanted to come so much. Luke was a babbling mess and mustered, "Please, please."

"Please, what? Are you begging me to stop? Or begging me to make you come." Marianna teased him and carried on stroking his cock. He squirmed beneath her.

"Yes, please stop."

Marianna laughed, relishing in her control over him. "You are doing so well, Lukey. Eleven minutes left." Almost halfway there, Luke thought.

The third round was agony. Luke's dick felt painful to her touch. He pushed himself into the sofa, trying to stay still. Every instinct in his body told him to come -- let himself go over the edge. He didn't know how long it had been before he had to call stop.

"Oh, Lukey." Marianna tutted. "Eight minutes left and only one stop. But I believe in you." Luke fanned himself with his hand. Then she started again.

Even the slightest touch from her hand was insanely pleasurable. Luke focused; he had the willpower for this. He concentrated on anything else, resisting the urge to fuck her hand. Then he felt a finger enter his asshole. Luke jumped.

"What no!?" He cried, "Stop! That's cheating."

Marianna stopped. "Who do you think makes the rules here?" Luke looked away.

"You do, Ma'am."

"That's what I thought." She grinned at him. "And that was your last stop. Six minutes left." Luke's mouth dropped open to protest, but as he did, she stuck a finger in it.

"I can fill that hole too if you like." Her eyes were lit, power-drunk and hungry. Luke sucked her finger.

"Good boy, lube it up for me."

Soon she returned her hand to his dick and started fingering his hole. Luke felt himself stretch open. He felt so vulnerable at this women's mercy. Another finger slide in. Luke let out a moan and pushed back onto it.

"That's right. You like it. Don't you?" Marianna cooed at him. "Tell me you like it, slut."

Luke caught her eyes and spluttered. "Yes, Ma'am. I love your finger up my ass." Marianna picked up the pace. One hand rubbing up and down and the other finger fucking him. Luke gripped onto the side of the sofa cushion as his hips thrust into her hand. He was going to cum. His orgasm was here. There was no more he could do. He threw his head back, and Luke's pleasure gave way to emptiness.

Tears formed in his eyes. Every part of him was tingling. Marianna trailed her fingers down his chest, letting her nails dig in slightly. Luke shivered under her touch, and his dick twitched unsatisfied.

"Well done, Lukey."

She flicked a chip and him, and it landed on his chest. Luke left it there and closed his eyes, panting. He heard Marianna get up but stayed there, cock pulsing, skin buzzing. He took some deep breaths and tried to calm down.

In his head, he added how much he had won off of her - $134. He had almost broken even. When he reached $200, he would go home; he had to work tomorrow. But a little voice in his head told him that was a lie. It told him this was his lucky night.

"Ahhhhh." Luke jumped up. "What are you doing?"

"Don't move," Marianna commanded. She had just poured ice all over his crotch.

Luke stayed still and watched his erection painfully disappear.

"Isn't that better? I want my toy to last the night." Luke blushed. He hoped he could last the night. She picked up a piece of ice that had some of his come on.

"$5 to suck on this." Luke opened his mouth. "What a slut." She laughed.

"Okay, get up. Ready for our next game?"

Luke nodded, glad to be free of the ice. "Great. On the floor." Luke found himself kneeling at Marianna's feet again.

"Kiss my feet and legs while I explain."

Not needing to be told twice, Luke kissed her toes. Slowly, he made his way higher as she explained. "You have ten minutes to make me cum as many times as possible without using your dick." She pulled out her phone and set another timer. "You will get $10 for one orgasm, $30 for two, $60 for three, $150 for four, and I doubt you could get higher than that."

Marianna hitched her red dress up and slowly slid off her lacy red underwear. She stepped out of them. Luke looked at them on the floor, and a desire to sniff them came over him. His head turned to the panties, and he lent over to them.

"No, No. Attention over here."

Marianna sat on the sofa and spread her legs. "Better get going, boy."

Luke knew what he was supposed to do. He kissed her legs, making his way quickly up to her thighs. Her wet pussy smelt so good. And it glistened wet. It made him feel wild, but he held himself back and started slowly, quickly finding the clit and started circling his tongue.

"Oh, wow. Goood boy. Someone has taught you." Marianna moaned as she pushed his head into her wet pussy. Luke was engulfed, her thighs squeezing his head. Unable to breathe, Luke pulled away and gulped down a big breath of air.

"Oh yes, that its. Right there. Keep going." Marianna bucked, grabbed his hair and pulled him further in, thrusting gently against his face. Then her thighs pressed harder into the sides of his face. She moaned. Luke could tell she was getting close. His jaw was aching, but he carried on moving his tongue.

He did something right, and she moaned again, pulling on his hair hard. The sudden pain cut through the pleasure of eating her out. He slowed down. "No. Don't stop," she cried. She pushed him away.

"On your back. Now."

Luke jumped up and lay on the sofa. Before he even settled, Marianna straddled his face. Her swollen red pussy came down over his mouth. Her wet juices smeared over his lips.

Luke didn't have time to enjoy the taste before she was grinding frantically on his face. Luke could barely breathe as his head rocked with her thrusts. Her moans grew louder.

"I'm going to come," she cried.

Luke could feel his dick twitching as she came over his face. He snuck in a breath and kept going, holding her down by her thighs. She was still moaning, and he felt her come again. She wanted to pull away, but Luke held her down and carried on. Her moans gave way to screams, but she didn't say stop. He could feel her third orgasm building. He opened his eyes and looked up at her. She looked magnificent in that moment, holding her breasts and head tilted to the sky. Her face struck with pleasure.

Luke heard the muffled alarm of the timer. She kept going, and she cried out as she came one more time. She slid off his face and lay on top of him. They both gasped for breath.

"Good... Boy."

They lay there for quite some time. Luke stared up at the high decorative ceiling, briefly wondering how much this massive suite cost. He felt a hand brush against his boner, and he looked at her. She felt small like this up against him. Her skin was soft, and she smelt so good. Luke could have stayed like this forever.

Finally, Marianna broke the silence, "I love finding subs in the wild." She flipped over and looked at him in his eyes. "Especially pretty ones." She kissed him on his lips. Luke blushed and became flustered for a moment.

"You did well, but that was only two orgasms -- the third was about 3 seconds too late." She giggled and stroked his chest. "One more game?"

"Yes, please, Ma'am." Marianna suddenly looked sadistic and domineering again.

She led him by his hand into her bedroom. Luke blinked. It was just as massive as the rest of the suite. In the middle was a wooden four-poster bed. She sat him down on the edge and went over the wardrobe. Luke admired her ass, and he held his hard cock, gently rubbing it. He wanted to take her dress off. He wanted to kiss her stomach, her breasts, her neck.

But Marianna had other ideas. As he turned around, Luke saw a large pink dildo. He grinned. He knew the next game, and he liked it.

"£500 -- to let me fuck you with this." She slapped him with it, and Luke automatically opened his mouth.

"Someone is a hungry boy." Without hesitation, she shoved the tip in.

"Come on, suck it like you mean it." Luke bobbed his head back and forth, he looked up at her, and she grinned down. She thrusted it down his throat. Luke spluttered, and his eyes watered as she held in. Then she pulled out, Luke gasped. He only managed to suck in a bit of air before she started, thrusting in and out. Tears were rolling down his face now, but he had found the rhythm and was enjoying it.

"Aw, don't cry. It's not that big." Marianna pulled it out of his mouth and held it. It dripped with saliva.

"Look, it's only a little bigger than the average." Luke looked up at the glistening pink dildo. He left his mouth open, wanting her to put it back in. Sucking a dildo made him feel so horny. Briefly, he wondered if he would like sucking the real thing.

He was going to take that up his ass. He smiled up at Marianna. She didn't know he'd done this before. She didn't know that tonight had been a crazy fantasy for him.