Higher Rollers Need to Unwind Too

Adrianna Chechik

*Definition of a “high roller”-a person who is in high demand for their trade, a person who works 70 plus hours a week, barely sleeps, and has major bank. Like Millions of $$- money. Not your typical 9 to 5 job. They can be a President of the United States, a Wall Street dude bro., a Stock Market Analyst, the best Civil Rights Esquire on the North East Coast, a NFL Tight End…the list goes on. And do not assume the above mentioned are all men.

*****

Chapter One:

December 31, 2018.

The petite in statute but curvy in the right places, silver -blond haired, classy woman headed towards the coat check from the company party which was in the most famous hotel in New Orleans, of which she had forgotten the name simply because( she giggled to herself), one, she was lit . As she made her way to the elevator, she suddenly stopped in her tracks and leaned against the cool wall. Flushed, her breathing increased from..well, excitement. She was thinking really hard about what just transpired a short while ago.

A short while ago…

The law firm decided to celebrate its success in winning a huge settlement, so the “Boss” decided to take the staff members, no pluses allowed, to New Orleans for a 3 day weekend.

Lil could not believe her sister! Lil-or Lilith found the joints when she opened her wallet to grab some cash to pay for her drinks and dinner when a deep voice came from behind her, startling her, spoke up, and she squeaked, quickly shoving the wallet into her purse before turning around. Her employer, her boss, Mr. T., lightly placed his hand on her back, as he caught her blushing and shoving something into her purse, he spoke to the staff, telling them that he was paying for her meals for the stay. Lil gasped and stuttered, flustered with surprise, “But…No. I can’t allow that.” She stammered, blushing, lifting her blue, green gray eyes up at his 6 foot 3 inch frame. “I insist.” and with that he lightly steered Lil towards the balcony by the double doors.

“But, Mr. T. you have done more than enough. I..” Lil was cut off. She felt the warmth from his hand burn an imprint on her middle back as he held open one door and let her lead the way through the door into the typical v humid, muggy night known in New Orleans at this time of the year.

Lil had decided to wear a freshly bought Anne Klein baby blue sheer maxi summer dress. It was so hot in New Orleans. Lil did not handle humidity well. She was constantly dripping sweat so she decided to wear something so light that she would not feel it on her hot flesh. Everyone else wore something they normally would wear in the office.

Lil was glad there were not many lights on the balcony. She was unaware that when she left the very well lit room to the balcony, the lighting was just right to offer a glimpse of her body as she walked onto the balcony, the lights made her dress more sheer, Mr. T. gaped as she walked ahead of him. He watched her beautiful silhouette , her flared hips as they swayed, the bounce of her nude, full ass and when she turned to face him he saw the lovely shade of pink blush half satin brassier , a flash of thigh as the dress was unbuttoned at thigh height, before Lil shifted the material over her exposed leg. He shook his head. She literally had him speechless. And she had no idea.

Lil was completely oblivious. Mr. T. quickly found a seat and sat down and tossed his long legs up and got comfortable, inhaling the multitude of fragrances that caressed his nose. Lil sat in the wood recliner nearby and reclined back, ignoring the soft material as it glided off the side of her legs, falling to one side of her thighs. She closed her eyes, rested her head back and allowed the tension from her body to roll off and away with the music as it lilted through the muggy night.

“Again, I insist. A diligent employer recognizes the hard work of a team member, let him indulge.” He told Lil, and he adjusted himself as he watched her lift her ivory legs onto the recliner, as the soft material of her dress caressed her thighs as it settles in a pile, and as Lil leaned her head back, closing her eyes. Mr. T. did notice as she took a long, deep breath and let it go slowly, she rolled her shoulders back and down. She offered a soft, “Mmmm” as she exhaled.

For several minutes, they both sat in silence, lost in their own thoughts or just enjoying the sounds and ambiance. Or, was there something…more…something unseen by human eyes, flowing through the New Orleans night?

Lil never spent much time with Mr. T.. He was ALWAYS busy. He never took a vacation. NEVER. Lil was so used to Mr. T. striding fast, into his office and being glued to his computer, then running to the courts along with his million other commitments to organizations and community ties.

She wondered when he would breathe.

She knew he was a former football player in his glory days. He definitely was in good shape for his age she thought as she eyed his reflection in the glass doors as they strode by earlier. 6 foot bursa escort 3 inches tall, wide shoulders, the navy blue suit was a respectful fit, not tight like any man under the age of 30 in the local firms. His soft brown hair was 60% gray now. His stride still could out walk any of the younger attorneys that tried to challenge him. She knew his thighs were thick and strong. Because she would look.

One time she was walking down the hallway of the firm when she saw a body stretched out on the floor. It was Mr. T. looking under the copier. She, for a brief moment, admired the nice and tightly formed ass before she knew whose it belonged to and blushed in embarrassment while fleeing down the opposite hall. She hoped to GOD he did not see her eyeing his assets.

He did.

“Uh, so, I happened to see something in your wallet…” Mr. T. leaned forward towards Lil.

“Oh Shit!” she exclaimed. Mr. T. threw his head back, laughing loudly as Lil scrambled for words. “My sister, the smart ass she is told me that I need to chill and snuck those in there. They aren’t mine!” she blushed so hard she covered her face in embarrassment.

“Well, do what she said. We aren’t in the office.”

“She sat up, “Really? Look at me..I am a 51 year old woman acting like a teenager getting busted!” She exclaimed as she swung her legs beck to the side of the recliner facing him, she opened her wallet and grabbed one of the joints and gladly lit up, taking a long inhale, softly blowing it away from Mr. T..

They sat out there on the balcony, quiet, enjoying the night and the sounds of the night. Music, several different songs but, all with the New Orleans Jazz Blues twang in them, laughter, traffic, people talking, the sounds of that particular New Year’s Eve night.

Mr. T. unbuttoned his jacket, took it off, placed it on the back of his recliner, leaned back, his arms behind his head, his eyes closed inhaling her soft, very feminine scent. Not the pot. Her. Floral…and what was that? Honey. Warm honey. Golden, floral warm honey. “Mmmm”

Lil ran her eyes from the crown of his head to the soles of his shoes. This, she thought, was a High Roller Man. He reeked of confidence and some arrogance, but, just enough without seeming overly cocky. She imagined that those days were behind him. He had to be at least 10 years older than herself. But, damn! If this fine man could give the young bucks a run for their money, she thought as she softly giggled to herself.

Mr. T. felt her dazzling gem eyes on him without actually looking at her. He didn’t want to embarrass her. He peeped his brown eyes open just enough to see her breasts jiggle when she giggled.

“What is so funny? he asked her, now fully staring at her.

“Oh! Honestly? You don’t want to know what I am thinking.” she covered her mouth, not believing she told him the truth, Her truth.

He looked at his watch on his right wrist. He sat up and turn his body towards her, resting his size 15 dress shoes just inches from her chair.

“Oh, but, I am very interested.” he leaned in towards her just a smidge.

“I don’t want to say anything because for some reason, I cannot lie to you!” she exclaimed and busted out in a fit of giggles, then full on laughter not able to control herself.

He smiled, enjoying her in the moment.

“Oh come on” he said to her.

Waiting.

“Okay, okay. Anything said in this conversation I can not be liable for.” She bent over giggling more. Her silver blond hair fell out of the messy bun, cascading over her creamy shoulders, her cheeks flushed from laughing.

He leaned forward and pushed a strand of hair to the side of her face, he lightly caressed her cheekbone, wanting to kiss her freckles.

“Try me.” He commanded.

Lil caught her breath when his thumb touched her skin. By the time she looked at him, he had pulled back and she swore it was a figment of her imagination because he was so damned composed and aloof looking.

“Okay. ” she stammered, wondering what the hell was in that joint because she was lit! She felt like she was on a cloud with Zeus himself. She fanned herself with a napkin.

“I think too much about your personal life. You work so hard and long hours, what 18 to 19 hour days? Do ya ever unwind?” she exclaimed passionately.

Once she did, she covered her mouth in shock!

“Ah shit, I am going to lose my job, aren’t I?” she asked him.

Mr. T. loved this side of Lil. How odd it was for her to wonder that when all he saw of her was professionalism even at a staff party. She was always composed. Never a hair out of place. Never late. She never said inappropriate jokes or gossiped with the other women in the office. He wondered what she did when she was not at work.

He smiled, “No. You are safe. I actually like this side of you, Lil. ” She could not believe he said that.

“We have our ways of unwinding.” he told her as he stood up. “BY the way, it is almost midnight. 5 minutes to go.”

Lil stood up, he extended bursa escort bayan his hand to her, helping her get to her feet. “I think I should go to my room.” she replied.

“Sure. You can do that. Or you can find out about the 5 floor party. By strict invitation only. ” He looked at his watch once again.

Lil was surprised. “Party? I thought we were at our party.”

“Hm” he replied. “Are you interested in going to this party?” he inquired looking out at the beautiful sights.

“If so, there are very strict rules one MUST abide by.” he said without looking at her.

3 minutes left until midnight.

Lil was baffled and well, intrigued. Why would her boss tell her that?

Lil thought, what the hell. why not? She wanted to explore New Orleans, so, why not?

2 minutes left until midnight.

“Why not? ” she replied.

Mr. T. was surprised but, he masked his surprise. Literally.

He pulled out a mask that somehow he had in his suit pocket and handed it to her.

It was a delicate silver and diamond partial mask for her. She marveled at its beauty. When she tried it on, it covered her eyes and theft side of her face to her lips.

“Go to the coat check, walk past it and head to the elevator, 5th floor. You must wear this mask for entry. You will be searched then given a list of strict rules you will need to sign off on then you may enter the suite.” He looked at his watch.

He bent his tall frame down to her 5 foot 4 frame, kissed her right cheek softly and said, “Happy New Year, Lilith.” and turned around to leave.

“Wait! Will you be there?” she wasn’t sure that she wanted to go alone.

He kept walking away from her, silent.

She looked down at the delicate mask. She felt oddly, empowered by the mask and invite.

She headed to the coat check.

———————————————————————————————

Chapter Two

“Miss. Miss. Are you okay?” Lil heard. She looked up to see a young man, eyeing her like a piece of candy. “Oh! Yes. I am fine. Thank you.”she pushed herself off of the cool wall and headed towards the elevator.

The handsome, young man followed her. “Are you sure? Because I can help you if you need.” he murmured. He was clothed in a very costly Italian suit, he looked and sounded European. Lil was tempted.

“I am sure you think you can but, I am good.” she sharply replied as she hit the 5th floor button. She watched as his face fell when the elevator doors closed.

Lil reapplied her lipstick in the mirror on the wall and slowly tied on the mask to her face.

She looked like an Ice Queen. Her pale skin, red lips, silver and diamond mask, her blond hair fell just touching her collar bone in a messy bed hair style. Lil felt…naughty, Daring… she unbuttoned the maxi to her cleavage, allowing a bountiful of soft curves to be seen, and unbuttoned a few more small buttons from the v of her thighs so that when she moved , anyone would get a glimpse of her bare, shaved womanhood. She actually was getting wet thinking about people eyeing her pussy. Her nipples grew hard, tingling, pushing against the satin material.

When the elevator doors opened, Lil was hesitate but, once she saw two Goliath looking hunks outside of the suite doors, she pushed herself forward.

Before she opened her mouth, Goliath number 1-who looked like a young Drago from Rocky, just as wide as the original Drago too, blond, with an accent spoke.

1. As I talk, you listen. No talking is allowed once you enter these doors. If you want to leave, just leave. No one will stop you. Arms up. As he told her the rules, the other Goliath, Persian God looking hunk lightly patted her down, winked at her as he ran his hands on her inner thighs.

2. Your body language will speak for you.

3. Sign this release.

4. No one will be disrespectful.

5. If you have a problem, raise your left hand and staff will assist you immediately .

6. Do you have any concerns? If not, enjoy your evening Ms. Lilith.

Lil gasped loudly, “How do you know my name?” she asked Goliath 1. He finally cracked a small smile. “We know all of our special guests.” with that he opened the door for her.

Lil was very surprised to see the release and was wondering what she was getting into here tonight. But, she was intrigued. And, there was a huge part of her that wanted to know if he would be there. That alone helped her to decide to sign the release.

When Lil entered the suite, she was surrounded by at least 100 well dressed, clearly affluent people of many races and backgrounds. She felt under dressed.

She honestly did not understand how her beautiful simplicity was alluring.

She was 5 foot 5 inches tall, full 38 c’s, small waist, full softly curved hips, a full ass to grab, strong thick thighs, silver blond hair, freckles on Ivory skin, hazel eyes that once could not tell if they were green, blue or gray at most times.

Wearing a baby blue summer maxi dress that clearly showed her curves, her escort bursa breasts nearly spilling from the baby blue dress, the buttons undone from thighs to the v of her essence , where if one tried they could see her beautiful, smooth womanhood when she flipped the dress off to the side of her lovely thighs.

Several people walked over to Lil and introduced themselves by not talking but, shaking her hand or a bow of their head towards her. Lil smiled shyly as she moved around the rooms, listening to the soft music being played by a life jazz band.

She was approached by a beautiful Nubian queen, who, if Lil maybe was into women, would have loved to taste her, had a tray of champaign and a tray of whiskey glasses filled with what Lil knew to be only the best whiskey around. She smiled and grabbed a whiskey. The beautiful Nubian queen bowed her head giving Lil a long, thirsty look, as she slowly licked her ruby full lips, eyeing Lil’s pussy as Lil moved the material to the side, in respect .

Lil walked softly from room to room, watching people. She swore that everyone was talking by using their bodies. She was fascinated.

Out of the corner of her eye, she saw a tall, imposing figure watching her. When she turned to look at him, he was gone. Lil wondered if that was him. She moved towards the room she saw the man who was staring at her was in. She saw a familiar figure , far ahead of her. At least to her he was familiar. It was the way he moved. It had to be him.

She moved around the people, like a silent dance. Nods of heads here and there from person to person, clinks of ice in crystal, music playing softly from room to room.

She lost track of him at the bridal silver and glass stair case. Lil decided to go to the top of the staircase and look out over the crowd for him. She looked carefully at every single male figure. As she was about give up, she saw in the corner of her right peripheral vision, a door open to one of many doors. She moved towards the door, where a soft glow emitted from.

As she entered she saw him sitting in a chair all by itself. He had a mask on. He bowed his head to her as she entered the room. He motioned to her to close the door. As she did, she heard a lock click. She spun around to look at the door when she felt him. He was literally leaning over her. His left hand on the door behind her, in his right hand was a paper which he was handing to her. Her breath caught in her chest. She could smell his very light cologne, see his lips, full, beautiful bow shaped lips.

He held a finger to her lips and pointed to the paper. Lil took the paper from him. He turned away from her and leaned on the deep blue wall. He unbuttoned his suit jacket, took it off and neatly folded it over the back of the chair he was sitting in earlier.

The paper had this on it.

_______________

Chapter 3

” No talking.”

“Tell me what is on your mind.”

Lil looked up at him. He was unbuttoning his cuffs all while watching her like a cougar that was stalking its prey.

Lil grew excited and scared.

She dropped the paper on the floor and strode towards him, unbuttoning her dress so that by the time she reached him she was only in her barely there bra and heels only.

Clearly he did not think she was this bold.

His jaw dropped open in total shock but, he quickly composed himself. he began to untie his tie when she reached him, pulled his hand off the tie, placed his hands on her body while she gently untied his silk tie, placed it on his jacket, and began to unbutton his shirt.

He pulled her in to his body as she did that and fiercely took her mouth with his, passionately he took ownership of her mouth and tongue.

They both began breathing loudly as they kissed, groaning loudly he grabbed her ass and squeezed it with all he had as he lifted her up, she squealed in surprise and wrapped her shaking legs around his waist as her carried her to the king size bed outfitted in navy blue silk sheets.

He sat himself down on the bed carefully not to slip off the bed, she adjusted her body on his. She finally got his shirt unbuttoned, pulled it out of his slacks. She pushed him back onto the bed, kissing his face, his neck, licking his nipples and she unwound herself from him and slid down his body. He groaned, clenched her arms tightly as she unbuckled his belt, her face was at his crotch level as she slipped his slacks off.

As she came up his body, she ran her hands over his calves, thighs and she licked his brown skin, nipping his thighs, her hands were stopped by …probably the largest penis she had ever seen.

He had to be 9 inches but, he was so thick, Lil wondered if he would fit inside of her! She slid her fingers around his throbbing cock, his cock was so hot. Lil looked to her right and saw the ice bucket and drinks.

She quickly put 2 ice cubes into her mouth and ran her cold tongue from the base of his cock, up the shaft to the tip. He jumped from the ice, but, damn, he knew it felt great! He wrapped his hands into her hair and gently lifted her up, he lifted her up and switched places with her, but, she was on her hands and knees. He slapped her ass, hard. Lil yelped, not in fear but, excitement.

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