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Michelles First Job Part 5

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There was an awkward silence on the deck of the boat for a few seconds and everyone was soaking in Michelle and the apparent uncomfortable look on her face. Melisa hopped up and wrapped her arms around Michelle while she kneeled, frozen on the teak decking. She kissed her neck and told her how hot she was and how fortunate they were to have found her. The others slipped down below to clean up and grab another drink, leaving Melisa and her young employee alone up top. Michelle turned to face Melisa and looked into her green eyes and said, “I feel a bit out of control right now, and I’m not sure where this is going.” Melisa dropped her head down to embrace Michelle in a passionate kiss. As she parted her lips and they exchanged tongues, Melisa could still taste Quinn’s cum, which excited her even more. Breaking the kiss, Melisa looked down at Michelle with loving, lustful eyes. “Sweetheart, you have lived a sheltered live, and we are just helping catch you up and there are so many more things we have to show you,” Melisa responded. Michelle smiled coyly. “If you promise to take care of me…..I can’t wait.”

The Hatteras slipped back up the Wadmalaw River to the Rutherford Estate on Ocella Creek. Four staffers were waiting at the dock to moor the boat around 10:00PM. The Rutherfords invited them inside for a nightcap, but they declined after the volleyball tournament and the sexual workout, everyone was pretty tired and Michelle told Melisa she was feeling a bit sore from Quinn’s huge cock.

They drove back to the beach house, without saying much to each other. When they arrived at the house, they slipped inside and to their respective bedrooms for the evening. Michelle jumped in the shower to clean up, pulled on a pair of undies, and after slipping into bed, was fast asleep before 11:00.

Michelle awoke mid-morning feeling rejuvenated after ten hours of sleep. She lay in bed listening to the waves crash onshore outside of the window, thinking about getting fucked the night before. She rolled over on her stomach against the silty sheets, and started to rub her clit and grind her pelvis into her hand. She slipped two fingers inside her pussy, rubbing her g-spot. Her breathing became labored as she started to approach an orgasm. She fantasized about Quinn’s huge cock stretching her out the night before. She could feel every vein in his cock as it slid inside her until he bottomed out. Her pussy warmed and became wet thinking about going down on Hope. She could almost taste her in her mouth, and feel her hard nipples against her skin. The fantasy was crushed by a startling knock on the door by James, announcing that breakfast was ready down on the veranda if she was interested. “Thanks James, I’ll be down in a few,” Michelle responded, now frustrated that the moment was over.

Nothing was mentioned about the previous evening at breakfast, aside from Melisa rubbing Michelle’s thigh and asked how she was doing. “I feel fantastic and like new after getting a good night’s sleep,” Michelle replied. “Great to hear, we have a client that flew in town last night that we have to meet for lunch, and we thought you could come along if you’re up to it?’” Melisa said. Michelle asked if she have time for a run and quick workout in the home gym before lunch. They agreed to meet out front around 11:30, and Michelle ran upstairs to put on her running shoes and a pair of shorts.

After running a couple miles on the beach, Michelle hit the gym and the shower before dressing in a mid-length light blue dress and sandals she had gotten at Corrine’s boutique. “You look like a million bucks,” Brian complemented Michelle as they headed out to Brian’s Lexus sedan that James had brought around front. They piled in to the car and headed downtown to McKee’s Social Club on Market Street for lunch. Brian and Melisa informed Michelle that they were meeting Winston Bingham, a very wealthy industrialist that spent the summers in Charleston and the winters at his estate outside of Tauranaga, on the Bay of Plenty in New Zealand. Their firm managed over $250 million in assets for Mr. Bingham, and they were meeting this afternoon to bring him up to date on the status of his assets.

They were shown to a corner table on the rooftop deck of the 150 year old building overlooking the Historic Charleston City Market and the historic business district. Within a few minutes, they were joined by Winston Bingham, and his personal security guard, Jason. “Well good-day to you all,” Winston proffered in a Kiwi accent, as he shook Brian’s hand and gave Melisa a hug and a kiss. “And who is this beautiful young woman you brought with you today?” he posed. “This is a new associate, Ms. Michelle Simpson from Kentucky,” Melisa responded. Winston reached out and took Michelle’s hand and kissed it as though she were royalty. “You know I have been to Lexington several times for the thoroughbred horse sales at Keeneland, and I’ve had three horses run in the Kentucky Derby. Beautiful state and I’ve found you find a lot of fun there without trying to look too hard for it.” Winston informed the Michelle. “So are Brian and Melisa taking care of you?” Winston asked. “Yes, and then some.” Michelle responded.

Winston Bingham was in his mid-50s, tall, at approximately 6’3”, and had an athletic build. Michelle could tell he took care of himself, was very handsome, and looked quite young for his age. She noticed he wasn’t wearing a wedding ring, and seemed to command the venue from the moment he stepped out of the deck. He and his guard sat and they ordered lunch and engaged in business talk. Winston found that his investments were doing very well, and Brian’s advice to divest his substantial oil production assets ahead of the crude oil price collapse in late 2015, served his client well. “You know Brian, if I hadn’t taken your advice and sold my shares in the oil sector, I might be homeless right now.” Winston said, giving Michelle a wink. Brian went through the rundown of assets and his portfolio pro forma. Brian had given a folder to Michelle on the drive over, who quickly gave Winston a run-down of his substantial real estate portfolio. Bingham was very impressed with her command of the numbers and projections, and she directly answered every one of his questions. If he had only known that instead of crunching the numbers the night before, she was getting fucked by a huge cock while she ate pussy. She gave no hint that she hadn’t seen his portfolio until a couple of hours before the meeting.

As the end of the lunch meeting approached, Bingham asked the three of them if they would like to come over to his house for drinks around 5:00. They agreed, and all hugged. Michelle was finding herself incredibly attracted to him. His cologne hung on neck after he hugged her and gave her a soft kiss on the cheek. She thought to herself thoughts of him doing things to her that wouldn’t have even crossed her mind a week earlier. Her sexuality had been awakened, and her lust was apparently evident on her face since Melisa gave her a knowing smile and took her by the hand as they walked back down to the car.

While waiting for the valet, Brian and Melisa complemented Michelle on her performance. The valet pulled up in the car, and Brian jumped into the driver’s seat. As Melisa and Michelle went around to get in the back seat, Melisa leaned over and whispered into Michelle’s ear; “Are you up for another interesting evening? Winston is amazing and I can tell that he wants you.” Michelle smirked. “I guess my job is to service our clients, so I’m game for about anything.”

They drove back to the beach house, and Melisa and Michelle tried on dresses that she could borrow for the evening. Michelle took a quick nap, freshened up, dressed and met Brian and Melisa downstairs at 4:30. They drove down to the Battery District, and the old mansions that lined the streets between massive live oaks, and hidden courtyard gardens. They pulled up to Tanglewood, a three-story white brick mansion constructed in the 1840s. They were met in the garden by an assistant, and shown into the study. Winston Bingham entered the room from the opposite entrance, and gave Melisa and Michelle both kisses on the lips. Drinks were flowing, and after about a half hour, Winston offered to give Michelle a tour of the house. The rooms were filled with antiques of the period, and fresh cut flowers were present on almost every table. Winston focused on Michelle’s tight ass and long legs as he followed her from room to room. As they passed back through the study, they ran into Melisa and Brian. “I’m going to run her down to the wine cellar for a few minutes if you all would like to move to the courtyard for diner in a short while.” Winston noted.

As they descended into the basement, the room cooled and Michelle’s nipples became pronounced through her light dress. As Michelle watched Winston move around the wine racks describing the various vineyard regions and vintages in his authoritative Kiwi accent, she couldn’t think of anything other than fucking him. The sexual awakening she had experienced in the past couple of days had created cravings for pleasure that had her desires slipping beyond her control. Winston was concentrating on his wine collection, and was oblivious that Michelle had grabbed the top of a heavy wood table in the cellar and hopped up on the edge, kicking off her sandals and propping her foot up on the back of nearby chair. He had grabbed and couple of bottles of red and was coming out of the chilled storage with a couple of white when he looked up to find Michelle sitting on the edge of wood table.

She looked so young and perfect to him. Her long tan athletic legs were spread revealed with one knee up, with her dress covering her waist. Two of the buttons on her dress were undone. She was leaning back on her elbows, looking him directly in the eyes. She didn’t say a word, as her eyes burned with a desire that caught him a bit off guard. Just minutes before, he was showing this wholesome, relatively unworldly young woman from Kentucky around his mansion while getting pepper with questions about his travels, antiques, and history of the previous occupants. Now he was staring at a stunningly gorgeous young woman giving him a look that immediately caused his cock to swell. He was transfixed and didn’t want to move or say a word to ruin the image in front of him.

The pause was broken when he noticed her look down to notice his swelling cock. She looked back up at him while slowly wetting her lips with a swipe of the tip of her tongue. Michelle pulled her dress up exposing more of her on the table. Without taking his eyes off Michelle, Winston placed the bottles in his hands on a shelf next to him and slowly moved across the floor towards her. As he reached the end of the table, Michelle extended her long leg and bare foot to his rub his now rock hard cock. Michelle could tell he wasn’t wearing underwear, and could feel his heavy balls resting on the top of her foot. She turned her ankle to feel up his shaft, noticing that he was quite large. She could feel a small wet spot of pre-cum that had soaked through his pants when she reached the tip of his cock.

Winston felt paralyzed and completely at her mercy. Normally, he was the suave, powerful, seducer of woman, but Michelle had completely and unexpectedly turned the tables on him. She gave him a quick smile and turned her eyes and head away from his stare over her left side, exposing her beautiful neckline and shoulder. “My God you’re stunning Ms. Simpson.” Winston whispered bending over to lightly kiss her delicately perfumed neck. She let out a soft moan of approval; her nipples now rock hard and pressing against the light fabric of her dress. She was more aroused than she had ever been her life. The moment was the perfect mix of eroticism, sophistication, and lust.

Winston had regained some control of himself, now being separated from her erotic look and reclined pose. He dropped down to his knees at the edge of the table, running his hands lightly down her raised thigh as he dropped. Michelle responded by lifting her other leg up on the edge of the table, and pulling her dress up to expose herself to him. Before him lay a perfect specimen; tone legs, a tight ass, and a tan flat stomach. He kissed her around the deep inside of her thighs, while Michelle started to writhe around and arch her back on the table. Her breathing increased as he worked his way towards her now wet panties. Her delicate young musk catching his nose, he lightly licked her through the thin wet material. He found the firm nub of her clit and pressed the tip of his tongue down and Michelle sucked in her breath. She reached down with her right hand and pulled the material aside, and Winston shoved his tongue deep inside. She bucked and slammed the back of her head against the table as a strong orgasm hit her.

As she tried to catch her breath, Winston rose to his feet and lightly caressed her thighs while she came back down. “Well young lady, I hope you enjoyed the tour?” he said smirking. “We’d better get upstairs…The others are probably wondering where we are.” Winston turned to pick up the bottles he had set down of the table. Michelle had composed herself and took his hand as he helped her down off the table. On her feet, she moved towards him, kissing him deeply, tasting herself on his lips. Pulling back she gave him a quick smile; “I enjoyed the wine cellar the best.”

Michelle was still a little unsteady on her feet after the mind-shattering orgasm she’d just experienced. As she slowly climbed the stairs from the wine cellar, Winston admired her athletic legs and tight ass as he brought up the rear. Her calves were strong and a deep channel ran down her tan thighs, defining the long muscles in legs from years of jumping and swatting on the volleyball court. He tucked the wine bottles under his arm, and reached up to caress them; unable to resist the temptation. Michelle paused the climb and look back over her shoulder with a naughty smile that melted him to core. Reaching down she pulled his hand up to her ass. “Can we continue the tour later?” she purred. “I think we can arrange for a special tour if you’re up to it Ms. Simpson.” he responded. “Maybe the others would like to join in the fun?” With that, he lightly smacked her tight little ass, urging her up the final few stairs.

They moved from the cellar through a long hallway with floor-to-ceiling glass and mahogany doors, which opened up to live oak-covered courtyard on to left and high ivy-covered brick and stone privacy wall on the right. Two massive wood doors at the end opened to a small parlor, where Melisa was sitting on Brian’s right leg enjoying a glass of bourbon as she sat on a wide leather armchair. “Enjoy the tour?” Melisa asked; smiling. “I believe Ms. Simpson found the cellar quite to her liking.” Winston responded, giving Michelle a wink.

Winston walked over to the wall and pushed a button on a digital consol. “Ms. Monique, can you come to the parlor? I need your assistance if you please?” About 30 seconds later, a stunning young creole black woman appeared in the doorway. She was only about 5 feet tall, and likely weighed less than 100 lbs. She was a light-skinned black, with hazel eyes. She was wearing a thin black dress, with a white sash around her tiny waist. She was likely in late teens, and very elegant and refined in her movements. “Ah yes Monique. Can you please ice down these bottles of white and decant the Château Ducru-Beaucaillou Bordeaux to allow it to breath before diner?” Winston requested. “Yes Sir Mr. Bingham. Diner will be commencing in about 15 minutes. Is there anything your guests need before diner?” Monique asked with a fairly strong French accent looking Michelle up and down. “This is Ms. Michelle Simpson from Kentucky Monique. She works from Brian and Melisa.” Winston advised. Monique walked over and took Michelle’s hand, introduced herself, reached up the embrace her, and gave her a light kiss to the side of her neck. Michelle’s instantly became wet, as she felt Monique softly press her tongue against her neck, during the kiss. She was so tiny and delicate, smelling of fresh flowers and linen.

During diner, Michelle could stop watching Monique as she served diner. Michelle soon noticed that she wasn’t wearing a bra, as her young perky breasts were exposed as he leaned over the table to grab a plate or fill a wineglass. She had long dark nipples, which appeared to be rock hard. After a wonderful dinner, the three retired to the parlor and courtyard, where more wine was waiting. The evening was very warm, and sweat glistened on Michelle and Melisa’s necks and chests. Brian suggested that Michelle go over and sit by Winston and Melisa. As she sat down, Melisa started to rub her leg and shoulder in light caressing movements. Monique appeared with iced wet towels rubbed with lemon peals and fresh ginger to cool off her guests. The cool towels and aromatics welcomed the night, and revived the energy of the room. Monique left and told her guests that she would stay through the evening, and to please just call if they needed her.

Melisa reached over to Michelle and pulled her to her, engaging her with a deep tongue kiss while pulling her over her leg. Both Winston and Brian watched to the two grinding themselves against each other. Winston got up and walked over to get another drink, getting a better view of the show on the couch. Melisa dropped to her knees, and dove into Michelle’s already soaking wet pussy. Michelle responded by digging her nails into Melisa’s back and throwing her head back against the leather coach as a moan escaped. She didn’t notice that Brian and Winston had pulled their think cocks out of their slacks, and started jerking themselves slowly as they watched Melisa bring Michelle to her first orgasm. She convulsed on the couch, not hearing Winston call for Monique.

Monique appeared in the door. She smiled and walked over to Winston, turning around to show him her back. Winston unzipped her dress, and it slipped over her tiny lithe frame to the floor. “Melisa could use some help with Ms. Simpson Monique.” Winston suggested. Michelle had not yet opened her eyes after the last orgasm until Monique caressed her breasts with her small hands. She sucked on Michelle’s nipples and kissed her way down to her pussy. Michelle remembered Monique’s scent, and asked her to make her make her come again. Monique found her clit and sucked it between her lips, while rubbing her tight asshole with her thumb. Her pussy juice and saliva ran down lubricated her rosebud enough for Monique to slip a finger inside. Michelle immediately came hard, pulling Monique into her. “Oh fuck Monique!” Michelle screamed, pounding the couch beside her as she hit her second climax of the evening. She pulled the little girl up on her lap with little effort as she looked deeply into her hazel eyes as Monique ground her tiny pelvis into Michelle’s.

Melisa was sucking Brian’s cock and Winston had taken off his clothes. He moved around behind Melisa and slid his large uncut cock into her from behind. Winston stroked in and out of Melisa, as her head bobbed up and down on her husband’s cock, her wrist twisting his cock at the top of each stroke. Brian was getting close to blowing and pulled Melisa off his cock, kissing her deeply. Winston picked up his pace, his heavy balls slapping loudly on Melisa’s hard ass. She turned back to look at him. “I think Michelle would like you to save yourself.” Melisa suggested. Winston pulled out and walked over to the couch where Monique and Michelle were stroking each other and kissing. He bent over and kissed Michelle. Monique grabbed his hard cock, already shinny with Melisa’s juices, and took her boss’s thick cock into her mouth. She took his cock down her throat, gasping for air every few seconds. He broke his kiss and sat down on the couch between them. Before he could make his move on Michelle, Monique mounted her boss, straddling his cock. She looked so tiny, almost like a little girl compared to his massive cock. Monique looked directly at Michelle as she lowered herself down and engulfed his engorged cock with her tight little pussy. “Oh my God…how do take all of him?” Michelle said aloud as Monique stretched herself, slowly taking him down to the balls. After waiting a few seconds to allow her petite frame to adjust, she started to ride him up and down, grinding her pelvis forward with each down-thrust.

Monique looked over at Michelle; “Mademoiselle Simpson, j’aime son énorme pénis. You try him now.” Monique stood up as Winston’s cock slipped out with a wet pop, and moved over on the couch beside Michelle. Winston stood up and helped Michelle up from the couch. She dropped to her knees and took his massive cock in the mouth. Monique had her tongue buried between Michelle’s ass cheeks, licking her pussy and rosebud. She pushed her tongue into her asshole loosening it up a bit. Michelle pushed back as the Winston’s thick cock pushed into the back of throat. Gagging, she pulled him out and stroked his wet cock looking up into his eyes, twisting her wrist at the top of the shaft with each stroke. Monique pulled Michelle up from behind and spun her around until she was facing the back of the couch. She climbed up on her knees, grabbing the back of the couch and dropping her head to point her tight ass up at her host. He pushed his fat head into her tight hole with a full stroke. Michelle’s hand clinched the back of the couch, digging into the padding. Monique stroked her back softly whispering into her ear. “Monsieur Bingham feels good, no? Have you ever had a man in your derrière?” “No,” Michelle responded with a grunt as she adjusted to his size. “I’m not sure I can,” Michelle half-pleaded as Monique smiled looked deep into her eyes.

With a wink, Monique moved around to get access to Michelle’s rosebud. She started working a finger into Michelle’s tight ass, and then two. She whispered as Winston slowed down to a gentle deep stroking rhythm to keep from coming before Monique had Michelle ready. After she had worked in a third finger, Monique pulled her boss’s shiny cock from Michelle’s dripping pussy. She spit on the head to add extra lube and pushed to head into the tight ring of Michelle’s ass. Winston slowly pushed his swollen head past her sphincter with a sudden pop. “Oh fuuuuucck!” Michelle screamed shocking Brian and Melisa who were fucking away like rabbits a few feet away. They both got up and moved over to watch the show as Winston slid deeper and deeper into Michelle’s ass with each slow stroke. She bit her lip and as she adjusted, started to push back to drive him deeper into her bowl. “Oh God Winston” she moaned. Michelle was in another world. She felt like he was going to spit her in two. She could feel every vein in his cock and it caused her to tighten up her sphincter in an attempt to keep him deep inside her. Feeling her asshole clamp around his cock, Winston responded by picking up his pace, her ass milking his cock with each stroke. “Fuck Michelle, I’m going to come.” He warned pulling out his cock from Michelle’s ass. Monique grabbed his cock and started jerking him off over the small of Michelle’s back. “Arghhhh!” he yelled as ribbon after ribbon of thick cum shot out onto Michelle’s muscular back and ass. Cum slipped down the small of her back, slipping into her gaping asshole, which had been stretched to its limits from his huge cock. Monique guided his cock back into her cum-filled hole before he softened, forcing his thick cum to shoot out around the sides of cock as her stroked into Michelle a few more times. Applause erupted from the side as Brian and Melisa cheered the show and the loss of Michelle’s anal virginity. Michelle rolled over feeling very uncomfortable with having her ass taken for all to see. Monique, noticing the look on her face, led her up by the hand and shuffled her into a nearby restroom to clean up Michelle and help her compose herself. As the door closed behind them, Winston dropped down on the couch breathing heavily. He looked over at Brian and Melisa grinned with approval of their latest professional hire. “I don’t know what to say Brian, other than thank you both. Ms. Simpson is a hell of an addition to your team.”

To be continued

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