I'll Do Anything, Sir Ch. 03

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Michelle becomes the entertainment for a few guests.
5.4k words
4.63
81.9k
59

Part 3 of the 3 part series

Updated 10/17/2022
Created 01/18/2015
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"Mandatory Meeting. 2:00 PM. Today. Large conference room. Send email." Michelle read the Post-it note on her computer screen and wondered why Attorney Derek Proctor was calling for a mandatory staff meeting with no warning. It was an early 9:00 in the morning, and Mr. Proctor hated last minute anything, especially last minute, unprepared for meetings. Michelle sent out an office wide email and leaned back in her desk chair, chewing on a pen cap and tried to figure out why they were having a surprise meeting. The firm's business had been steady, if not growing, so certainly Mr. Proctor wasn't planning on firing anyone. Were they merging with another firm? Was another attorney going to be promoted to partner? Was someone leaving?

"Hey Cindy," Michelle called from her cubicle to the blonde on her left, "any idea what this meeting is about?"

Cindy turned, her bob haircut swooshing around her tanned neck. "No idea," she shrugged, "maybe Proctor's retiring? He made five million off that Campbell settlement last month. Maybe he's leaving? I still can't believe they got five million dollars from that BS case."

Michelle smiled. "Yeah, me neither." After the surprising and undeserved settlement from two insurance companies, Mr. Proctor had treated the office to lunch at the swankiest restaurant in town, followed by surprise bonuses. Michelle was quiet when the secretaries gossiped about what they received for a bonus. Michelle's bonus had an extra zero at the end.

But oh, if the office only knew what she had to do on Saturdays for that extra zero. For months, she was Mr. Proctor's... well... sex slave? The slave part was slipping away week-by-week. Michelle was enjoying her overtime work with Mr. Proctor. The harder he worked her, the more she loved it.

She turned back to her screen, trashed Derek's note and continued to work. The hours ticked by slowly as the office began to hum with curiosity. Derek had been behind his closed office door all day. No one could hear what was going on behind those sound proof doors. He hadn't even popped his head out for a lunch break. At 1:55 PM, the staff slowly rolled into the conference room in one large wave. They all sat around, pens and paper and cell phones in hand, waiting for the boss. At 2:05 PM, Derek stepped inside the conference room and closed the door.

Michelle's breath caught in her throat. Derek was smiling, beaming in fact. His smile was a positive sign and everyone in the room seemed to release a silent sigh of relief. The boss looked healthy, younger even. Gone was the scruffy half-beard he kept constantly trimmed and neat. His hair was combed back and his figure seemed even taller and prouder than ever.

"Everyone, I have some great news," he announced. "As you know, I have been discussing the future of this law firm with some important people. People who can help this firm grow and expand more than I could have ever thought possible. With our name, their expertise and their financial backing, I know this firm can become one of the most recognizable in the city within a matter of five years."

Everyone was stunned. Expanding the firm? No one had even thought of it as a possibility. Commercials, billboards, bus signs. All of them, featuring their name, their pictures. More cases. Higher salaries. Tenure in the company, promotions and more. There was an unspoken buzz of excitement around the room.

"I'm going to have to meet with Michael and David tomorrow. Michelle," his eyes locked with hers. Tension crackled and his eyes stared glittering. "I need to see you in my office to go over travel arrangements for our visitors." Michelle nodded, her red hair bobbing up and down. She bit the tip of her tongue to stop from smiling. She was sure travel plans weren't the only thing he wanted to go over in his office. "I'll let you all get back to your work. Michelle, meet me in my office and bring a pen and paper," he ordered and left the room.

She hurried after him, pen and paper already in hand. She walked into his office and closed the door behind her. He stood behind his desk, both palms pressed flat against the wood. "Sit," he ordered. She obeyed, crossing her legs, revealing a glimpse of her lace top thigh highs under her dress.

"I'll need you to book three round trip tickets for our guests. They have to be direct flights. I don't want to inconvenience them with stops. Get first class seats and put those on my personal credit card. Book them their own separate rooms in the Sheraton. I have a discount there, and make sure they have all the accommodations they will need. Let the hotel know these are important people so the rooms better be clean. No problems, understand me?" He fished around in his suit jacket and pulled out a black Amex card.

Michelle's mouth watered a little at the sight of the tiny piece of plastic. She blushed and nodded. He handed her the card, which she tucked into the pocket of her dress. "Good. I'll want breakfast and lunch ordered here to the office when they are here as well. Also, there has to be entertainment while they're here. That's where you come in." Michelle stopped writing and looked up into his flashing eyes. She felt her palms begin to sweat. This was not good.

"Michelle, I think we're almost finished with our little arrangement. You've been paying off your debt for months now. I think we can call it finished, on one condition."

One condition? Entertainment? Finished? Michelle mind whirled. What was he thinking?

"You're going to entertain our guests the same way you've been entertaining me for the last few Saturdays. Three very important guests need special accommodations after all." He smirked as he leaned closer, towering over her shaking figure.

"What?" she squeaked.

"You're going to be the entertainment. This is how it's going to play out. You're going to wear a special outfit I bought you. It's in that bag in the corner." He pointed to a plain brown bag, with no labels or hints. "You're going to wear what's in the bag next week, the first day they are here. You're going to be a perfect little Mad Men secretary, all smiling and cheerful. And you're going to work overtime. Now, when the rest of the office leaves, I am going to offer to take you and our guests to dinner. You will be polite. You will be friendly. And you're going to get yourself very drunk on my tab. Then we are going back to their hotel, where you will entertain them. Somehow. Someway. And when they are done with you, take a cab, or spend the whole damn night with one of them and buy new clothes in the morning. I don't want you doing some slut walk of shame into work the next day Do you understand me?"

Michelle's red lipped mouth gaped open like a fish, too dumbfounded to speak. She nodded, stood, and took the bag.

"Oh, and Michelle," Derek called, "I won't need you working this weekend. I think you're overtime can be better served next week. Enjoy your Saturday."

************************************************************************** The week went by in a blur. On Saturday, Michelle went to the gym, cleaned, cooked, and did everything she could think of to distract herself from the upcoming Thursday—the day the firm's visitors would be coming and the night she was dreading. But this was her chance to be finished with Derek and their "arrangement." As much fun as she had with the man, she wanted to Saturdays to herself again.

The work week sped by and the visitors were comfortably checked into their rooms. Michelle had seen to it when they walked into the office on Thursday. Mr. Wilks was a tall, sturdy black man, shorter than Mr. Proctor, but younger. He looked like he had been a good football player in college. And he was handsome, so much so that Michelle almost didn't mind the arrangement Mr. Proctor was planning.

Mr. Jameson was a tall off the boat Irishman, with a thick brogue and thicker eyebrows. His flaming red hair was bright enough to see down the block, but he looked good for a middle aged man. A little heavy, but nothing horrid about him. He was a pleasant man who enjoyed jokes and laughing. He kept touching Michelle's shoulder and calling her "sweetheart." Michelle wondered if Derek had told them about the arrangement.

Miss DeFleur was a gorgeous, skinny woman with mile long legs, soft brown hair tucked into a modest chignon and perfectly pink lips. Her tight black dress showed barely there cleavage and soft curves. What could Michelle possibly do to entertain her? The answer stuck her when Derek met with her and kissed her twice on the cheek. She was for him to entertain tonight, judging by the dapper smile and his flashing eyes.

The meeting had seemed to go well with the attorneys. The paralegals and support staff were interviewed one by one. Numbers were examined and crunched behind closed doors. The day flew by with little interruption to the daily office routine.

At six o'clock, Michelle smiled and said good night as each person filed out the door, leaving only her, Derek and their three guests. "You sure you can't meet up for drinks tonight? I mean, it sucks that Derek made us all stay an extra hour. Maybe you should unwind a little?" Michael asked as he shrugged on his suit jacket and started walking towards the door. Michelle shook her head and apologized. She had to work overtime.

She smoothed down her tight red dress, with her generous cleavage threatening to spill over the top, the slit in the back so high that someone could almost see the tops of her stockings or a strap of her garter, courtesy of Mr. Proctor. She reapplied her lipstick, smoothed her hair in her small compact mirror one last time and knocked on the partially open conference room door where Mr. Proctor was meeting with their guests. "Come in," Mr. Wilks called out.

"Hello. Sorry to interrupt, but your dinner reservations are in twenty minutes."

"Michelle, do you have plans tonight?" Mr. Proctor asked right on cue.

"No, sir, I don't."

"Good," he leaned back in his chair and smiled, "come join us for dinner," he offered and the four of them stood to leave.

"Oh, no, I couldn't impose like that, Mr. Proctor," she smiled. They had rehearsed this part yesterday.

"It's no imposition at all."

"Besides," chimed in Mr. Jameson, "we'd love to have the company of yet another lovely young woman." Michelle smiled and blushed.

She giggled. "Well, alright then. I'll call the restaurant and tell them to add one more." She left to get her coat and purse, pretended to call the restaurant, and left with the rest of them.

Dinner conversation was light and pleasant. Questions flew around the table about possible expansions, new office locations, promotions. Michelle felt excited and giddy to be there. Her nerves were slowly vanishing. The four gin and tonics she drank were helping too. Before the main course, Mr. Wilk's finger traced the edge of her dress. Before her third gin and tonic, Mr. Jameson's large hand patted her knee. Before dessert, she caught a glimpse of Ms. DeFleur reaching over under the table and Mr. Proctor's eyes widened. Tonight would be interesting.

The bill was paid and the five of them left, nearly stumbling across the street to the Sheraton. "We should see you to your rooms. Make sure everything is alright," Mr. Proctor said. No one argued. Michelle was giggling and giddy. Her face was numb and the sensitive spot between her legs was damp and sensitive. She was drunk and excited. She didn't know why but she liked the butterflies-in-her-tummy feeling.

They piled into the elevator and stopped on the eight floor. They all piled out. "Can I stop in here and use your bathroom," Derek asked as Mr. Jameson pulled out his key card to enter his room.

"Sure, sure," the Irishman waved and entered the room. Everyone followed. The room was spacious, large, one of the better business suites in the hotel. A large king sized bed dominated the focus of the room, but left enough space for some play. The writing desk looked sturdy. The TV was a newer model, an HDTV with a small plastic pamphlet next it showing a variety of pay-per-view programs.

Derek went into the restroom and closed the door, returning a minute later. Michelle sat on the bed, talking to Mr. Jameson who rested his hand on her knee. Mr. Wilks sat behind her, leaning her against him as his large hand stroked her soft skin. Ms. DeFleur watched as Mr. Jameson leaned in to kiss Michelle. Michelle giggled from Jameson's scratchy beard tickling her chin. She turned her head and Mr. Wilk's warm lips found her neck, reaching the sensitive spot in just seconds.

Ms. DeFleur took Derek's arm and tried to pull him out of the room. "No, let's stay," he insisted. He gently pushed Ms. DeFleur up against as wall, her thin body pressed against him. Her small breasts crushed against his chest, her legs parting to let him in closer. He kissed her, her soft lips playing and teasing him.

He heard Michelle giggle again, breaking his concentration. He looked over. Ms. DeFleur kissed his neck, her arms reaching around him, her soft lips teasing his skin. Soft shivers pricked at his skin, his cock growing and hardening in his trousers.

Michelle was kissing Wilks, her red lipstick smudging around her lips. His large dark hands traced her pale skin, up and down her lean arms. He watched her shiver as Wilks pulled her down onto the bed, laying on her right side, her head tilted away from Derek. Jameson stood and kicked off his shoes and laid down on her left side. His hands pushed her skirt higher up her pale thighs. Derek could see the strap of her garter belt, the lace top of her thigh high stockings. His mouth went dry.

DeFleur's hands found his cock stirring in his pants. She massaged and teased his dick through his pants while her lips traced around the collar of his shirt. She reach up and slid the jacket off his shoulders, dropping it to the floor. Her fingers laced under the knot of his tie and pulled his head back to her. She kissed him hard on the lips, her tongue snaking her way into his mouth and dancing with his. She let go and pulled off his tie, dropping in onto his jacket. Derek's hands reached up behind her and pulled down on her dress' silver zipper, which ran down the entire back of her dress. It slid off her and onto the floor between them.

Her red bra and panties clashed with her black garter and stockings, which made him stiffen further. Her taught body, which was tapped beneath him, was long and lean, a sharp contrast to Michelle's petite and generous curves. His hand reach down and cupped her sex. She moaned as his fingers slipped between her thighs, her mouth parting in a breathy gasp. "Oh," she moaned as his fingers teased her damp clit, beneath her soaked panties. Her head leaned back against the wall, mussing up her hair. Her breasts arched out to him and he reached for them with his free hand.

He slid one breast—he guessed a B cup—out of the shell of her bra, her nipple puckering under his palms. He squeezed it gently and she moaned louder, her head thrown back and her body arching towards his touch. His fingers worked faster between her legs, one finger working under her panties and sliding deep into her dripping cunt. She was soaked.

DeFleur moaned, twisting and writhing under his skillful hands. He leaned down and flicked his tongue across the tight tip of her breast, eliciting little yelps from the power hungry woman's mouth. Oh, how she was so supple and sweet when she was getting off. Or so he thought.

As her orgasm drew closer, she pulled away from his fingers and turned him, pinning his back against a wall. She unbuttoned his shirt buttons one by one, then slipped the shirt off his shoulders. She yanked at the hem of his undershirt in hurried frustration and pulled it over his head. With expert swiftness, she unbuttoned his suit pants and had them and his boxers around his ankles in seconds. His cock spring out, long and heavy.

DeFleur reached down and teased the head of his cock with her long fingers. Her red painted nails were wrapped around him, squeezing and teasing. Her eyes glinted with power she knew she had over him. Her lower lip was caught between her teeth, her lipstick smudged in a pink ring around her lips.

She squeezed harder and his cock twitched. His smirk faltered and she let go of his cock., leaning closer to him, her tits brushing against the hair of his chest, her whispered in his ear, "I want to taste you." She lowered herself, kneeling at his feet. Her pink lips opened and her tongue stuck out, licking the underside of his cock. He twitched on her tongue and groaned as sparks of pleasure shot from his balls to the base of his spine.

Her tongue was so soft, applying perfect pressure to the head of his cock, swirling around the tip like she was licking an ice cream cone. His balls tightened when her lips finally took the head of his cock into her mouth. They stretched, pink and pretty around his thick heavy member. Sweet pink against a deep tan. She looked like a fetish porn star in that position. He took her hair in his hands, pulling on it until it was out of her tight style and falling in waves to her shoulders. He took the silky locks between his fingers and held on for the ride.

Michelle was overwhelmed by both men beside her. She could hardly keep track of whose hands were where and what they were doing to her. All she could feel was pleasure. The men turned her head back and forth to kiss her and their hands unzipped her zipper and slid her dress down off her body. She looked down and could see one dark skinned hand between her pale thighs, one light, long fingered hand groping and squeezing her breasts over the bra her boss had made her wear. Pleasure was swirling throughout her body, radiating from her thighs and breasts. She closed her eyes and let the men work their magic, her body losing itself to their touch. He writhed on the bed, her hips pressing harder into Wilks' hand, which teased her thighs. Jameson was unclasping her bra and sliding it off her shoulders. Both men took a nipple into their mouths and sucked. Michelle whimpered, a strong tingling shooting to her low belly.

Wilks' hand moved faster. Derek had made sure she hadn't worn panties at work and now she was grateful. His fingertips teased and rubbed her soft skin with no lace between them. Her thighs were sticky and damp as he pulled her legs further apart. One finger slid deep into her belly, his thumb tweaking her clit. She yelped and moaned.

Jameson released her breast and slid down between her legs, stripping as he went. In his boxers and undershirt, Michelle could see a stout, thick cock stirring under the fabric. Her sex clenched on Wilks' fingers at the sight. Wilks slid his hand from her legs and Jameson settled down between her legs, resting her curvy thighs over his shoulders. His hands reached up over her gently curved stomach, then he pinched her tits. She yelped, her hips bucking towards his face. "You smell so sweet," she heard before his tongue flicked out and licked her opening.

Michelle opened her mouth to moan, but Wilks' long dark cock was sliding between her lips. He had stripped completely, the large well built, dark man looming over her where Jameson had been laying seconds ago.

Jameson's tongue pressed harder onto her clit, making her moan, taking Wilks' cock further down her throat. Wilks' grabbed her hair and hammered his cock to the back of her throat, making her gag over and over as pleasure built up between her thighs. Her lips stretched tight around the black cock in her mouth. She screamed on it when Jameson slid two fingers deep in her wet cunt, his tongue never stopping, and proceeded to finger fuck the squirming redhead.

She screamed as her orgasm overtook her, stars shooting from the back of her skull, pleasure washing over her and consuming her. Wilks' cock brought her back to reality as it slammed quick and hard down her throat. A burst of hot, heavy cum shot to the back of her throat, making her gag as she tried to swallow Wilks' load. Her lips tightened and she sucked, the last of her orgasm ebbing away. Jameson's tongue and stopped and his fingers slipped from her legs.

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