6 comments/ 61052 views/ 39 favorites I'll Do Anything, Sir Ch. 02 By: SecretSecretary "Miss Jones, can you come to my office please?" the intercom buzzed on Michelle's desk. Her boss, attorney Derek Proctor, was back from court later than he had planned. Michelle was beginning to pack up her desk for the weekend, ready to go home and enjoy a chilled glass of Merlot. The week had been long and stressful. Mr. Proctor—Derek as she called him in private—was working her harder than ever, now six days a week. Monday through Friday, he loaded her with extra work. This was his public punishment for the costly mistake she had made, which cost the firm more than her salary doubled. He had intended on firing her until she agreed to work Saturdays too. Saturdays had become a different kind of work for Michelle. Rather than sit behind her desk, she was often kneeling under Mr. Proctor's desk, or bent over his desk. He had arranged for her to work exclusively for him 9-5 on Saturdays under the pretense that she was working twice as hard for the same pay to make up for the money she had lost. No one in the office knew what types of jobs she was expected to perform on Saturdays. It had been two weeks since their arrangement. Derek had begun testing the waters with Michelle. They tested out positions on his desk. He made her dirty talk in his ear while he jerked off to a porno. She had swallowed loads and loads of his cum. She had taken it in her pussy so much she'd lost track. The one perk seemed to be how hard Michelle came when he screwed her in his office. The thrill of someone coming in to grab something and catching them excited Michelle. The feeling of helplessness whenever she walked into his office on Saturday mornings and sat down in a chair as she waited for him to show was more exciting than anything she'd ever experienced with her old boyfriends. Michelle pressed the intercom button on her phone and said she would be right there. Cindy, the last secretary to leave for the day, waved goodbye and Cindy slung her purse over her shoulder and left. Now Michelle was alone with Derek. 5:05 on a Friday. She wondered what he needed from her. Would he torture her by making her file for the next few hours? Would she have to type a small pile of handwritten letters he had created over the week? Would he have something dirty in mind? Or was he simply giving her instructions for their rendezvous tomorrow? Michelle stood in her Jimmo Choo nude stilettos. Straightening the bottom of her cream colored dress, she tucked a strand of red hair behind her ear and walked into Mr. Proctor's office. As usual, Mr. Proctor had his chair turned around. She could see only the top of his hair behind the large leather chair. She heard him clacking away at his laptop, furiously working. "Derek, you wanted to see me?" she asked. "Is everyone gone for the day, Miss Jones?" "Yes sir," she replied. She took a few steps further inside and sat down on one of the small leather chairs across from his desk. He had no knick-knacks cluttering his desk. He kept them on a bookcase along with intimidating volumes on civil law, contract law and some terms Michelle didn't understand. More than once, Michelle had been tempted to ask what torts were, but she bit her tongue. His desk was bare, clutter free, and his filing was organized. He kept his office and his appearance crisp and clean and professional. He swiveled in his large chair, his shoulders straight, his arms relaxed. "Good," his smile bordered on a smirk. Michelle's stomach fluttered with nerves. She knew from the flash in his eyes that he had dirty images rushing through his mind. He was planning something kinky and torturous for her tomorrow. She was afraid to ask what. "Don't look so frightened of me, Michelle. You know I won't hurt you more than you can handle." His smile turned friendly, as if this was just joke to him. Michelle simply nodded. She bit her cheek so she wouldn't say something she'd regret. She wanted to tell him off. She wanted to tell the dirty old man to go screw himself. He was twice her age. He was manipulating her. He knew how badly she needed to keep this job, and he knew she was stuck. He stood, his handsome face staring down at her. He walked around his desk, his shoes squishing on the plush carpet. He stopped a foot in front of her and leaned back against the edge of his desk. Last week, he had dragged Michelle to her knees and made her give him a long blowjob in this same spot. "I don't want you to come to the office tomorrow, Michelle," he said. His face gave no clue as to why. Was he letting her go? "Um, ok?" she said. "I plan on working from home tomorrow. I have a lot to do and I think the day will be much more productive there. But, since our arrangement says you have to work Saturdays, I see no reason why you can't work from my house as well. Don't you agree, Miss Jones?" Alone in his house for eight hours. Michelle's stomach lurched at the thought. The sicko would probably throw her in his basement and keep her locked in some damp dark room for hours. He might even be one of those perverts with some sex dungeon. Her brows furrowed. Derek almost laughed at how adorable she looked when she was angry. Her skin flushed red and she was about to scream. Her chest heaved and strained against the tight, heavy material of her dress. Derek's moth watered as he stared at her large chest. His stiff cock jerked in his pants. "Remember our deal, Miss Jones. I'd hate to see a pretty little thing like you out on the street with no job." Michelle sunk lower in her seat, her face still red, and her eyes damp and dewy. She wanted t curse him out, slap her hand across his cocky grin and leave. He knew she hated their arrangements. She hated him for forcing her. She hated him for how hard she came when he fucked her. She hated that she had no choice if she wanted this job. "Here's my address Michelle. I still expect to see you at nine sharp," he handed her a post-it note with his address. "That will be all Miss Jones. Have a good night." He turned and walked back to his chair. He sat down, turned around, dismissing her. She heard the keyboard keys clacking away again. She stood on numb legs and left. **************************** Michelle took a long deep breath as she stood on Mr. Proctor's doorstep. She had thought a dozen times about turning around and running away. She wore her running shoes just for the occasion. And sweatpants. And an old high school cheerleading t-shirt. Which she covered with a baggy hoodie that had a red wine stain on the left breast. She was determined not to impress him. She wanted him to think less of her and to end this ridiculous arrangement. She rang the doorbell. Her stomach fluttered as she heard a shuffle of feet behind the door. Seconds later, Derek pulled open the heavy wooden door and stepped aside. "Nice outfit," he commented with a smirk. Michelle had the gross feeling of snakes sliding up her spine. He ushered her inside with a wave of his hand and closed the door behind her. "You're late," he said. She looked at the clock. It read 9:05. "Traffic was bad," she answered. Derek turned towards her, his tall frame overpowering her as she stared up at him. His eyes were flickering like candlelight. He was thinking something, planning something. He had the same look in his eyes before he went to trial. "You live ten minutes away, Michelle. Now tell me, were you late on purpose?" "No." "Did you have an emergency?" "No." "Clearly you didn't spend any time primping for me, so you weren't late because of your wardrobe choice. Is it laundry day, Michelle?" "No." "Then why would you think it's appropriate to wear those clothes to work?" "Well, we're not in the office sir," Michelle began, a thin sheen of sweat covering her neck. The house was warm and his gaze was hot. "I thought I'd be more comfortable working in your house if I just dressed, I don't know, normal I guess." "Take it off," he commanded. Michelle froze. He couldn't be serious, could he? "Take off your clothes Michelle. If you can't dress professionally for your job, then you shouldn't be dressed at all." Michelle remained frozen, terrified at the thought of staying naked, all day, for him. She would be even more open to him. He could see every curve and every inch of her. There was so much more space in his house than his tiny office. Hell, there was room for two couches, a TV, a fireplace, a coffee table and a plush armchair in his living room alone. Derek rolled his eyes. Michelle crossed her arms over her chest. He strode towards her and grabbed the hemline of her hoodie. "No, please," she begged, shaking her head. Tears began to pickle in the corner of her eyes. Her stomach clenched. "Unfold your arms, Michelle. When I give you an order, I expect you to follow it. You are, after all, my assistant." He released her hoodie. "For now anyway." He took a step back and eyed her. Her red hair was falling in waves around her sad, flushed face. Her bottom lip trembled. He wanted to lean down and bite it gently, carefully. His cock stirred in his pants. Michelle shook as he gazed at her. He wasn't stepping away. He was invading her space, so much so that she felt suffocated. The air in the room was gone. Her head was spinning. She gave in and took the edge of her hoodie. She lifted it over her head, slid it down her arms and dropped it on the floor. Next came her cheerleading t-shirt. The warm air suddenly felt cold. Michelle looked down at the floor. She could feel her nipples straining against the fabric of her bra, scratchy and tingling. The flutters in her stomach softened. She almost enjoyed the feeling. She froze again. She didn't know if she should keep going. She knew she should, but something about stripping out of her pants in front of her boss felt so wrong. He hadn't told her to take off the t-shirt yet, but she did it anyway, without asking. What was wrong with her? She took a long deep breath. Derek stepped closer again and grabbed the elastic band of her pants. He pulled them down to her ankles. She kicked off her shoes and shimmed out of the pants. Bending down, she slid off her mismatched socks. One was lime green. One was pink with Hello Kitty. Michelle was mortified at the childishness of her socks. Only her underwear matched. She cursed the mild OCD she had when it came to her underwear. Everything she wore had to match. Otherwise, she went braless or pantie-less until she had matching lingerie again. Right now, she stood in matched red satin underwear. Her panties were a tight red thong and her bra was barely push-up. She never needed to wear push-up bras. She had enough of her own breasts without faking them. Derek took her by the arm and led her over to one of the couches. He sat down. Taking her hips, he walked her so she stood in front of him. He leaned back and admired her. She watched him, his gaze tracing over every dip, every curve. Michelle felt excitement pooling low in her belly. She loved when men watched her. She loved being desired, wanted. Now her boss was here, sitting in front of her, soaking in every detail. He twirled his finger and she turned, facing away from him. After a minute of silence, she felt his large hands slide up her back, strong and hot. He unclasped her bra and she let it tumble to the floor next to the coffee table. His fingers slid under her panties, over her hips. He slid those down too until they pooled around her ankles. A sharp pain and a loud slapping sound against her ass made Michelle yelp and jerk forward. "Put your hands on the coffee table, Michelle," Derek instructed. She obeyed, her mind rushing like an express train, wondering what he had planned. "And what's this? Enjoying your job, are you?" His fingertip dipped into Michelle's pussy, rubbing against her clit. She could feel how wet she had become. She blushed. He pressed her clit harder, rubbing the little nub in just the right way. Michelle whimpered loudly, her back arching. Her hips pushed further towards his touch. "Like that do you?" he asked. "Yes," her voice was a breathy gasp. "Yes, what?" "Yes, sir?" she said. "Good girl." His hand came down hard on her right buttock. She squealed, lurching forward. His hand came down harder on the left side. "Get on all fours on the table," he instructed. Michelle obeyed. "Good girl. I'll be right back," he stood and left the room. Seconds later, he was back. Several long lengths of white rope were wrapped in his hands along with a small gag. A rush of panic swept over Michelle. She began to stand and back away. "No, don't Derek. Please, don't." He grabbed a fistful of hair and yanked her head down. He pulled her arms and legs back into position of the coffee table. He gagged her and quickly knotted her wrists and ankles to the table. Michelle's tears flew freely down her cheeks. She shook her head, trying to tell him "no," with a gag still in her mouth. When he finished, Derek tugged on each of the ropes. They were tight. She couldn't move more than a few inches in each direction. His hand fell on her ass again. The pain made Michelle yelp and scream into the gag. His hand fell down hard, over and over. He slapped the backs of her thighs. His hand even found her pussy a few times. Michelle could really scream when he slapped her pussy. She was shaking on the table, a strange feeling building in her gut. She hated this. She hated him, but she could feel her pussy, soaked and beginning to drip onto the table, her lube running down her thighs. Why was she enjoying this? Slap. What was wrong with her? Slap. Why did she agree to this? Slap. Slap. Oh God, would he just stop? Slap. She needed more than this. Slap. She needed... Slap. Needed... Slap. Oh, what the hell did she need?! Slap. Long minutes ticked by. Michelle didn't know how long Derek had gone on spanking her on the table. With his hand. She heard the buckle of his belt being undone She whimpered in relief. He was going to fuck her now. He was going to fuck her and get this over with. Derek stood back, admiring his handiwork. Her ass was a pale, bright pink. He could do better than that. Her pussy glistened, the small landing strip of hair damp from her cunt. She wanted this. She was fucking loving this. His cock strained harder in his pants. She would be so tight right now. He would slide in with one hard fuck. He would fuck her balls deep and it would feel fucking amazing. His secretary had such a tight pussy. But he was a patient man. If he waited, it would be even better. She heard him slide the leather out of the belt loops. He was really slow getting undressed. Smack. Michelle screamed, her back arching and twisting as the harsh leather of his belt came down hard on her already tender skin. Again and again, he lashed her ass with his belt. The pain almost overwhelming. Michelle's tears came in a fresh wave, dripping along with her own lube onto the coffee table. The pain was harsh, but not much more than his hand. The sound scared her. It was so much louder and intense, but the pain was bearable. Derek continued his assault on her. Her ass was turning a deep pink now. He pulled back, dropping the belt to the floor. He watched her body relax instantly when she heard the belt fall. He spanked her ass cheeks one more time. She needed to know that was not nearly over yet. Derek kneeled down, his face level with her damp pussy. She smelled sweet and musky and he knew she would taste fantastic. His tongue flicked out over her opening. He prodded, his tongue barely entering her. She was so tight. He was going to enjoy this. He turned his face under her now. He clamped his lips over her swollen clit and sucked. He chuckled as she screamed into the gag. Her hips tried to buck, but he grabbed her hips, his fingers digging into the soft, pale skin. He would leave bruises, but he liked the thought. Michelle must have enjoyed it too. A fresh, warm wave of her juices slid from her hole. He lapped them up, tasting her sweet honey. She moaned and whimpered behind him. His tongue darted in small circles, then licking every inch of her, lapping at her sweetness like a dog. Michelle moaned and arched, her clit was so sensitive and his tongue felt so good. Her skin was hot and tight. Small pricks of pleasure were shooting through her like tiny bolts of lightning. Her nipples felt tight. Wave after wave of pleasure were crashing over her. She could feel her orgasm building, her limbs tensing. She was getting close. His tongue was not stopping. She didn't want it to stop. She tried to remind herself that this was Derek, her boss, her boss who was twice her age, who could fire her at the drop of a hat. None of this slowed down her need to cum. It made her grow hotter, wetter. His beard scratched the soft skin on her thighs and his tongue was gentle and slippery. He was so much better than her old boyfriends and dates. The man had enough experience to know how to use his tongue. It felt fantastic. Derek leaned more onto the table, one hand sliding back. His fingertips grazed over the sensitive skin of her stomach, then her ribs. He found one of her large breasts and gently rubbed the soft skin. Michelle moaned harder and louder into the gag. He pinched and tweaked a nipple and she screamed. Michelle's orgasm was right on the edge. Derek could feel her tensing over him, her pussy dripping lube at a steady rate now. With one last lick, he stopped. He slid out from under her and she whimpered and groaned in protest. She shook her hips towards him, her ass still pink from spanking. Her pussy glistened with her lube and his spit. He smiled at the pretty picture she painted for him. He stepped around, watching her back arch as her head tried to turn far enough back to watch him. He walked around the table, stepped in front of her and took the ball gag from her mouth. Spit covered the ball and her lower lip. A small puddle of it had pooled on the carpet. He tossed the gag aside. "What're you-" Her question was cut off as he began to unzip his pants. Michelle watched, her eyes riveted to his zipper. Slowly, inch by inch he pulled it down, teasing her. He unbuttoned the button on his pants and slid them around his knees. His hard, heavy erection slipped out of his pants and smacked her across her lips. By instinct, she opened her mouth and stuck out the tip of her tongue. He stepped closer, his hand gripping the back of her head firmly, his fingers lacing in her silk red hair. He took his cock in his hand and guided it into her mouth. Derek closed his eyes and groaned, his head rolling back. Her mouth felt so damned good. Her tongue flicked out to taste him, swirling around his head. She lapped at a bead of pre-cum that oozed from the tip. He slid in deeper, her lips stretching. Her cheeks hollowed and she sucked hard. "Christ," he muttered. He moved his hips back and forth in small motions, only sinking half of his cock into her warm, wet mouth. She felt amazing around him. He looked down. Her lips were flushed red, stretched wide around his cock. He could feel her tongue rubbing against the underside of him. Pleasure shot through his cock to his balls, reaching his lower back. His toes curled and his knees buckled slightly. He gripped her hair. She stopped moving her tongue. Her eyes looked up at him. She tried to move her head back, but he kept her still. In one quick thrust, he shoved his cock deep into her throat. She gagged. Music to his hears. She gasped for air around his dick as he slid it out, keeping only the head in her mouth. He was stretching her throat. She felt trapped, her arms and ankles starting to hurt from the ropes. She wanted him to let her go. She could throat fuck him, but she wanted it at her pace. He was too much for her to take all the way down her throat like this. His grip tightened and he slid his cock, balls deep in her mouth again. His balls rubbed against her chin. She gagged, her lips brushed against the hair on his groin. He moved his hips in a steady rhythm now. Her mouth felt so fucking good, gasping for air around his cock, taking in every inch. He thought his mind would explode every time she gagged on his cock, her throat tightening on his head. He could feel his balls tighten. This wasn't how he wanted to cum. I'll Do Anything, Sir Ch. 02 He released her hair and slid his cock out of her mouth with a loud pop. She gasped for breath, her head bobbing as her face flushed. She strained against her bonds. He kicked off his pants and walked back around to her backside. He smacked her deep pink ass once on each cheek. She was dripping wet again. A small puddle of her pussy juice was dripping in long, heavy drops onto the coffee table. Derek never would have guessed that his little secretary liked getting throat fucked. He nudged the head of his cock against her swollen clit. She bucked and moaned. She was so ready. Her pussy look tight, like a small pink fist waiting for his cock. He nudged her opening with the tip of his dick. She leaned back against him, trying to take more of him. He slapped her ass again. She yelped. His cock twitched. He grabbed her hips, his fingers digging tightly into the soft pale skin. In one quick thrust, he shoved half of his cock deep inside her hot cunt. She screamed, her back arching. One more shove and he had landed balls deep inside her tight little hole. She was so hot for him, so wet. He felt so big inside her, stretching her beyond her limits. He was so thick and swollen, his cock so hard. Michelle tried to wiggle against him to make more room for his cock. His fingers dug tighter into her hips. He slowly began to fuck her. Michelle moaned, pleasure filling her lower belly as her boss took her from behind like a dog in heat. "Oh, fuck yes," she moaned as he filled her hole, stretching her. She could feel how wet she was around him, slippery and hot. This was incredible. So wrong, but so amazing. Derek reached one hand down between her legs and found her swollen sensitive clit. He moved his fingers in small circles. She squeezed his cock, more lube gushing onto him. "Oh yeah, that's it. Fuck yes!" she screamed. "Such a good little secretary," Derek groaned behind her, his fingers moving faster. Pleasure was shooting like sparks through her whole body. Michelle could feel herself building to an intense orgasm. Her legs and arms were so sore and stiff, but the thought of stopping sounded like insanity. She didn't want him to stop. She would die if he stopped. She was so close. "Cum for me, you little slut," he get go of her hip and spanked her. His fingers quickened more, his hips now his cock into her pussy in a quick fury. Michelle screamed his name was she came. Her back ached beneath him, her pussy squeezed his cock. His balls tightened painfully. He was going to lose it too. He bent forward and squeezed her breast tight, his finger slippery with her lube as he teased her clit, her orgasm building again into a quick, intense second. "No, sir no, please! No, fuck sir, not again! NO!" she screamed so loud for a split second, he wondered if the neighbors could hear him taking his little secretary. He didn't care. Michelle shattered beneath him, cumming so intensely she nearly fainted. Stars exploded behind her eyes, her whole body shuddering as he fucked her, her orgasm washing over her, drowning her in pleasure. She squeezed him again and his cock exploded inside her. His balls tightened and released, his cum shooting deep into her belly. He knew she wasn't on the pill. He told her not to take the pill while she worked for him. Fuck, if this didn't get her pregnant he didn't know what would. As she calmed down, panting against the coffee table, her arms and legs began to give out. Derek took long deep breaths and, slipping his softening cock from her pussy, he walked around in front of her. He grabbed her hair and lifted her face. Her cheeks were flushed, her lips swollen and pouty, a deep red, near purple. She was panting for air. Her eyes were foggy with a strange afterglow. He slipped his cock between those swollen lips. A strong tingly feeling shot through his dick as her puffy lips worked him. "Clean me," he ordered, "then I'll let you go home for the day." Her tongue and lips slid around his cock perfectly. She sucked on him gently, her tongue licking away their juices. She could taste the last few drops of cum sliding out of the tip, her own lube coating him. They tasted amazing together. "As much as I like working from home," he said, "next Saturday we're back to working in the office." As he slipped his cock from her lips, Michelle smiled. "Yes sir," was all she could say. I'll Do Anything, Sir Ch. 03 "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. I'll Do Anything, Sir Ch. 03 Wilks' finished with her mouth. He stepped off the bed and made room for Jameson, whose short fat cock seemed to reach for its turn. Michelle knew she wouldn't quite gag on his cock, but she wondered if it would even fit in her mouth. Behind Jameson, Michelle could see Derek, pinned against a wall with DeFleur on her knees, working his cock in her mouth. His eyes were staring down at DeFleur with hunger and lust. A spike of jealousy shot through Michelle. That look should have been only reserved for her. Jameson slid his cock between Michelle's lips, blocking her view of Derek. Wilks took his place between her legs, sliding her thighs wider over his broad shoulders, exposing more of her wet cunt to his mouth. She moaned loudly, louder than necessary, when his tongue found her clit. Derek's head shot up and he nearly blew his load into DeFleur's mouth, stopping himself just in time. He could see Michelle trying to take Jameson's soda can sized cock into her petite mouth, her red lipstick smudged all around her lips. Wilks' dark head was between her thighs, a sharp contrast to her pale skin and the small, neatly waxed tuft of red hair running along her mound. Derek's cock twitched in DeFleur's mouth. DeFleur, try as she might, could not deep throat him as deep as Michelle, nor as well, but her tongue still felt good. Derek watched as his little secretary came on a black man's tongue and gagged on an Irishman's load while cum dribbled onto her chin. DeFleur pulled herself away from his cock and turned around to see what was distracting Derek. She stood was walked over to Michelle who was shaking on the bed, her last orgasm taking a toll on her energy. "You're not finished yet sweetheart," DeFleur purred. "One of you get under her back." Wilks obeyed, his cock stirring again. He slid under Michelle, tucking her body close to him as her back pressed against his chest. He slid her legs wide on either side of him and slipped the head of his heavy cock into her wet, open hole. Michelle moaned at the invasion, staring at everyone around her, wondering how and why this was happening. She was dazed, confused and drunk, but everything felt so good. She watched in almost awe as Wilks' big black cock buried itself balls deep inside her tight hole, filling her. She let her head rest back on his chest and moaned. Wilks began to move inside her and stretched her, his cock reaching her womb. Michelle yelped when DeFleur's tiny tongue flicked out and licked her cunt. DeFleur kneeled on all fours in front of Michelle and licked the secretary's pussy. Michelle twitched and bucked and DeFleur took the swollen clit between her lips and sucked, tasting Michelle's juices on her tongue. Derek stood behind DeFleur, his fingers prodding her opening, rubbing her clit. With his free hand, he guided his thick cock to DeFleur's damp opening. She was tight, but not as tight as Michelle. It felt like DeFleur was a woman who got around a lot. He slid his cock balls deep into DeFleur in one hard thrust. She moaned, her head pushing harder against Michelle's pussy. Derek watched as the woman beneath him rocked back and forth with his thrusts, her head moving closer, then further from his secretary's dripping pussy. He watched Michelle, her tits bouncing in Jameson's hands while the Irishman pinched and teased her nipples. Michelle's head was thrown back in ecstasy from the tongue and cock working her hard. She could not handle so much pleasure and he knew she was close to cumming a third time. Derek watched and pounded his cock harder into a strange woman's pussy as he stared at Michelle. Her dark red lips were parted and her eyes were closed. Her pussy was tight, squeezing around the dark cock thrusting in and out with increasing enthusiasm. She was writhing on Wilk's big, black cock. Derek smirked as he watched her face twist one last time. She was about to cum. He couldn't touch her, couldn't feel her, but he could sense that she was about to cum.He knew her body well. "Fuck!" Michelle screamed, shuddering and shaking above Wilks. Wilks grunted twice, his cum spurting deep into Michelle's belly. Thick white semen leaked from Michelle's wet cunt and onto the bedsheets. After a minute, he slipped his cock from Michelle and moved out from under her. Derek pounded DeFleur's pussy harder. He could feel her tightened around him, her face still buried in Michelle's cunt. "Lick her," he commanded and DeFleur listened. Her tongue stretched out and licked Wilks' cum mixed with Michelle's lube. Derek tweaked her clit one last time and DeFleur came screaming. Her pussy clenched and squeezed on his cock, trying to milk Derek for his cum. He wanted to cum, but he also wanted to wait. He knew what he was waiting for. When DeFleur's orgasm had ebbed away, he pulled her up and slid his cock from her loose hole with a heavy plop. He helped her stand off the bed before walking across the room to look for his pants. Jameson laid on the bed and flipped Michelle over. She straddled his hips and wiggled to let his thick cock into her pussy. She used Wilks' cum as lube and slid the Irishman's cock balls deep into her. She moaned and bucked, his cock thicker than any toy she had ever used before. Jameson's brow was furrowed in concentration and Michelle knew he would be finished in a matter of minutes. She rode Jameson's cock with wild abandon and enthusiasm like porn stars she had watched. "Oh yes, oh God yes," another orgasm was building, her pussy was so sensitive now and the head of Jameson's cock was rubbing her G-spot. Jameson reached down between her legs and teased her clit, her orgasm rocketing closer and closer. She pinched her tits and rode the cock under her, everyone around them watching. Michelle stared at a breathless DeFleur, a worn out Wilks, but she could not find Derek in her field of view. She wanted him to see her like this, wild and free, riding a thick cock for him, because he told her to. She wanted to please him more than any man she had fucked before, more than any man she was fucking now. She wanted him to see her acting like the slut he loved to watch. Jameson's face twisted. Michelle's pussy clenched and squeezed as another orgasm overtook her. She moaned and screamed and bucked on Jameson's fat cock, her pussy sore, stretched, swollen and satisfied. Jameson groaned her name as he held her hips in place, letting her spasming pussy milk him for his cum. After a few seconds, pleasure overtook him and he came, thick, heavy spurts of cum mixing inside Michelle's womb. They both panted and moaned as their orgasms faded away. After he caught his breath, Michelle rolled off of Jameson, who stood, leaving Michelle alone on the bed. Michelle saw Derek. He had been standing at the foot of the bed, his cock still hard and thick. He was waiting for her. He held a small bottle in his hand. "On all four, Miss Jones," he instructed. On shaky legs, she turned over and obeyed, cum dripping from her cunt and onto the bedspread. Derek kneeled behind her on the bed, feeling the eyes of everyone else around them watching his every move. His cock stiffened harder. He took the bottle of lube and lubed his fingers. He dropped the bottle next to him and teased her ass, the only hole he had never used before. His finger prodded and poked. Michelle squirmed against the strange sensations at first, but then relaxed, allowing his finger to slide all the way into her, stretching her. With more lube, Derek slid a second, then a third finger into her opening, stretching her for his cock. Michelle whimpered. Derek pulled his fingers from her tight, soft hole and lubed his cock then slid more lube over her entrance. His hand reached around and cupped her swollen sex, his fingers stroking her clit. "Relax," he said and began to enter her. Michelle's body tried to jerk away at the invasion, but he pulled her back to him by her hair, her head yanking back. She screamed as inch by inch, Derek invaded the most personal, intimate area of her body. Her eyes stung as tears fell from her cheeks. Small shots of pleasure mixed with the pain as Derek's fingers worked her clit, spiking her interest. Michelle moaned as Derek's balls slapped against her pussy's entrance, damp, sticky and still dripping with cum. Derek reached under Michelle's arms and pulled her up against him, cupping one breast with his free hand, his fingers still working her clit. The tight ring of her entrance squeezed him harder than any fist. Her hole was softer than any mouth. This was amazing. He fucked her fast and hard in short quick thrusts. Derek knew his secretary had never been ass fucked in her life. Her opening was so tight and her hole was so soft, so foreign to him. He could not hold out much longer. DeFleur had been a tease, a distraction revving him up for his big finale. He held her body close to him, his fingers pinching her large, swollen tit, his hand rubbing her clit harder and faster in just the right spot. Michelle was moaning "Oh God" over and over again, her mind lost to the feeling of his cock, stretching her, branding her, fucking her. He leaned down and whispered so only she could hear, "This is my hole. No one else can ever touch it. No one else's cum can ever enter it." His thrusts came harder and faster. Michelle was shaking, pleasure spiking from her ass throughout her body. She could feel an intense orgasm building up in her, stronger than any she could remember. "You are my slut. You are mine to share. You're my bitch, Michelle." Michelle screamed his name as her orgasm broke over her, knocking the wind from her lungs. Pleasure exploded and her whole body shook uncontrollably. In the distance behind her, she heard Derek whisper "I love you," in her ear before he moaned her name, his cum squirting deep into the only area she swore no man would ever touch. Their orgasms meshed together, Michelle shaking and falling onto the bed, her body limp, spent and exhausted as the last of Derek's cum shot deep into her body. He panted above her and slapped her ass once, a deep pink handprint left behind as stinging reminder of what he whispered and what none of the other lovers in the room could hear.