I'll Do Anything, Sir Ch. 02

"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.