The Assistant 63013

Theodore approached the boss's office with a nervous rumbling in his stomach. He had only worked at Lavender Inc for a couple of weeks and hadn't had the time to get used to the office life just yet, so being summoned by the higher-ups felt unsettling. With a deep breath, he knocked on the big door, which quickly swung open to reveal the huge, empty office. He felt small as he stepped inside.

Long, dramatic shadows were cast along the floor, bathing the office in the amber glow from the setting sun. In the office, only a small desk sat alone. Behind it sat Miss Emily, the boss of the company. She was handling some papers, her fiery red hair falling down her shoulders. She looked up from her desk, her orange eyes locking onto him, a long, dramatic pause following after.

"Ah, Theodore, come on in," she said, gracefully removing her glasses, eyes like living flames.

He stopped in front of the desk, the office eerily silent, perching high above the ground and isolated from the outside.

"You... wanted to see me?" his voice stammering, nerves betraying him.

"Yes," tucking a lock of hair behind her ear, leaning over her desk with an innocent smile on her face. "I wanted to discuss a business opportunity with you."

"O-oh, that's... interesting," he tried to sound professional, but failed miserably trying to sound confident.

She chuckled, amused by his horrible attempt. "Well, you see..." leaning back in her chair, sending shivers down his spine. "I need a new assistant. My last one unexpectedly..." the long pause setting an eerie tone. "A coworker mentioned you are quite skilled with... paperwork. Is that right?"

"Y-yeah, I-I'd say my skills are quite strong," he said simply.

Her smile broadened. "Good, my schedule is quite packed and... messy, so I need a capable assistant to manage it for me. Do you think you can handle that responsibility?"

"Uhm... yeah, I believe I can," nodding quickly as her eyes settled heavily on his shoulders.

"Are you sure?" Her expression hardened. "I need someone reliable and obedient. A good... dog, so to speak, that follows my every instruction without question," sending an intense glare Theodore's way.

He assumed her to be half-joking, but was taken aback by her seriousness. Giving a strange look, he nodded in agreement.

"Good," judging eyes scanning his entire body. "I have heard rumours that you are a virgin, if I'm not mistaken?"

Theodore's face flushed red. Despite his discomfort in admitting his lack of sexual experiences, he agreed.

Miss Emily's eyes sparked, her smile growing even wider. "There is nothing to feel embarrassed about," licking her lips as she said so. "It's a professional choice and nothing to be ashamed of."

Theodore felt slightly more at ease, still not understanding how his virginity had something to do with all of this.

Suddenly, Miss Emily rose from her chair and sat down on the edge of the desk with one leg drawn up beside her. She adjusted her posture, making her breasts more noticeable and making it harder for Theodore to concentrate.

"I might have my first assignment for you, Ted," Her tone creeped him out.

"W-were starting now? The clock is soon--"

"Shh," Miss Emily interrupted him right in his sentence, placing a finger over her lips. "An assistant doesn't question. Are you ready for your assignment or not?"

"Y-yeah, if you say so," He hesitantly replied, feeling mixed emotions.

With a sly grin, she demanded he come closer, and Theodore walked around the desk to stand in front of her. Despite being taller, he felt so much smaller than her. She leaned against her desk, supporting herself with her arms.

"First assignment," she licked her lips before continuing. "Unzip my pants."

"What?" Theodore exclaimed, taking a step back. "I can't do that!" Bewildered by her request, he attempted to leave the office, but Miss Emily grasped his tie, stopping him in his tracks.

"Do you want to be my dog... and obey my orders?" both staring deeply into each other's eyes, one with mischief and one with fear. "A dog follows its orders?" She yanked him closer, his tie like a dog collar. "So will you follow mine?"

"O-of course, M-Miss Emily," he answered, feeling oddly compelled to comply despite his mind screaming at him.

"Good, now unzip my pants."

His hand traced downwards, hers still firmly around his tie, not letting him try to escape again. Slowly, he unzipped her pants, unbuckling her belt too. His hands moved automatically, like some external force was controlling him.

"Good, now reach under my panties."

"Miss Emily--"

"Shhh," she silenced him again, placing her fingers over his lips. "Do as you're told," and without further protest, his hand slipped under her underwear. His hand met her slick and warm vagina.

"Now, gently rub me and slowly push your fingers inside me," the words came slowly, whispering with a predatory grin as his fingers began rubbing her labia.

Theodore felt a mixture of surprise and pleasure as he followed her directions. Slowly, his fingers caressed against her clit, wandering further inside her. Her breath quickened as he massaged her insides, enveloped by her warm fluids. It was like a sauna inside her, every stroke making Miss Emily shiver and gasp for air, but she still stayed in character, trying to not drop her mask.

"Next task," she suddenly exclaimed, interrupting the date between Theodore's fingers and her vagina. Yanking out his arms from her underwear, she held his hand between the two of them, covered in her vaginal fluids. "Now open your mouth."

Theodore just stared at her in shock, still unsure if he should follow through. But without protest, he opened his mouth where she guided her fingers inside it.

"Now... close your mouth."

Her possessive words were difficult to ignore. Despite his reluctance to follow her orders, he did as she told him. The unpleasant taste of dirty water and urine hit his taste buds.

"And now, swallow."

Theodore shook his head, his discomfort evident, but that only made her more frustrated, pushing his fingers deeper into his throat.

"Swallow..." she said again, her tone forceful as his fingers brushed the back of his throat. But Miss Emily was unfazed, finding it rather pleasant seeing him struggle. Struggling to stay upright, Theodore fell over the desk, catching himself with his hands. Seeing no other way out of the situation, he let her juices run down his throat, cleaning his fingers thoroughly as Miss Emily wanted.

"Does it taste good?" her voice low and soothing with a sadistic smile on her face. His head bobbed up and down, Miss Emily pulling out his fingers, satisfied with his answer.

"Good, now sit down on your knees," her commanding tone carrying such a weight that his legs went numb. Now, his face was mere inches away from her crotch.

She then lifted her leg in the air and firmly placed it on his lap. "Take off my heels," commanding him like a slave. His trembling fingers moved closer to her feet. Slowly, he slid her foot out of her heel, savouring the feel of her nylon sock. After both shoes were off, she let her pants fall to the ground, kicking them to the side, now only her black stockings hiding her legs.

Unclasping her stockings, he peeled her socks off, his climax surging like a tidal wave. Revealing her long, firm and bare legs, he was finally holding her naked feet in his hands. His heart beat faster and faster while caressing her soft feet, feeling sensations he hadn't felt before. With gentle motions, he ran his fingers between her toes, nails coloured in a matte black, curling to the touch of his fingers on her soles. Miss Emily just laughed at the stupid look on his face.

"Time for the next task... take off my underwear," without skipping a heartbeat, Theodore reached up and grabbed her waist and her panties and slowly guided them off her legs. His gaze was locked on her voluptuous thighs, immaculate and impossible not to love. Now with only the end of her shirt covering her privates, his anticipation for the next task was through the roof. With her long fingers, she lifted the end of her shirt, revealing her wet vagina. The urge to touch it became overwhelming, placing his index finger on her red, trimmed pussy and rubbing it slowly.

"You liked the taste before, didn't you?" Theodore nodded in agreement, even though he wasn't a big fan of it. "Good, then drink," she commanded, parting her vagina with her fingers.

Taking a firm grip around the back of his hair, she tugged him closer, their lips meeting in a sloppy embrace. He parted his mouth, pushing his tongue deep inside her. As his tongue danced inside her, Miss Emily made her moans clear and audible. The taste of her was intoxicating, her flavours somewhat sweeter this time. Clasping her thighs, he continued to delve deeper into her delicious, wet flesh, Miss Emily's soft moans echoing in the office. Her thighs jerked after every breath she took, gripping tighter around his hair as her body tensed up.

Suddenly, she began gushing everywhere, her whole body violently trembling as she did so. Her pleasure erupting in a series of forceful blasts, coating his entire face, Miss Emily not letting him move away for a breath of air. Her moisture drenched his clothes, face, hair, everything, soaked in her love juices. His clothes sticking to his skin and hair tangling together, her juices like glue. As her orgasm subsided, her breaths became heavy and slow, gazing down at the work with satisfaction.

"Wow, you are a thirsty one," panting heavily with amusement as she peeled his lips from hers, some long strands of her glistening essence hanging between his lips and her throbbing groin.

"Stand up for your next assignment," rising quickly from the floor.

Miss Emily fell over her desk, sitting firmly in the middle of it. She parted her long legs, revealing her temple again, an open invitation for pleasures yet to be explored. With a tantalising look, she stared Theodore up and down, his clothes obstructing her view.

"Take off your clothes and pull your dick out," she seemed desperate, eager to see what he was hiding underneath, hiding her smile behind her parted fingers.

Swiftly, his pants and shirt flew off, kicked to the side. His naked body completly exposed for Miss Emily to feast upon. Her gaze landed on his erect penis, pulsing with desire, eyes growing more and more seductive. A playful chuckle escaped her, giving him an inviting impression, and Theodore took a step closer to her.

But as he neared the desk, Miss Emily's expression shifted. In a quick motion, she stomped down on his penis, pinning it against the desk.

"Aah!" he cried out in pain, his hand flung to his mouth to muffle it. The sudden pressure on his cock made his eyes tear up a little.

"I never gave you permission to shove your cock inside me," suddenly sounding angry. "You just couldn't help it, Mister Horny Boy."

Her tone was playful, laughing as she slowly began rubbing her foot against his shaft. Confusion struck him as the mixture of pleasure and pain left him in a conflicted state of arousal.

"I saw how you admired my feet earlier... do you like them so much?" Teasing him as his penis twitched under her toes.

"Th-they're nice," was the only thing he could get out of him.

Her foot continued in deliberate and sensual strokes, the pressure increasing as she rubbed against his aching cock. He tried his best, muffling his moans, but it was difficult. The way her foot teased him made him tremble, unable to withstand it.

"Wow, you are really liking this, are you? Fantasizing about having an affair with your boss? You naughty dog," she taunted, laughed, teased, Theodore enjoying it all. "Say you like my pussy... say you want to stick your tiny little dick inside me."

"Y-yes, I-I need to," his voice stammered from the intensity. "I want to stick my d-dick inside you, p-please," Tears and drool dripped down, both from pleasure and pain. He sounded so much like a dork when he said it, but it was too overwhelming.

She simply laughed at his pathetic words. "You sound so much like a pervert... I like it," Continuing to rub his throbbing dick, her foot sweat coating his shaft. She picked up the pace as Theodore was nearing his edge.

"Do you want to hear a secret?" Theodore looked up into her eyes, a wicked grin on her face. "I'm not wearing any bra... would you like to see?"

Quickly, he nodded, blood pumping through his veins and eyes glued on her chest as she seductively untied her tie and unbuttoned her shirt. One by one, the buttons flew off, revealing more and more of her skin, the contour of her soft hills clearly visible through the cloth. When the shirt was off, she threw it to the side, her naked breasts hanging from her chest. They were round, smooth, perfect, neither small nor big, just perfect. She grabbed one of hers and lightly squeezed it, cupping it in her palm. She played around with it, letting the fat pour out between her fingers.

"Do you like them? Do you think they are beautiful?" she whispered to him.

"They're fantastic," he calmly said, eyes fixated on them.

She pinched her nipple, rolling it around between her index and thumb. The way they moved was hypnotising, her moans teasing him as she stroked her chest.

As Miss Emily continued to squeeze his dick with her foot, Theodore could feel it throb more and more, nearing his edge. His cock pulsating eagerly, trying to hold it in as he didn't want to spew his cum all over her magnificent body.

"Emily, p-please stop... I'm g-gonna c--" he said, his breath weighing heavily on him, making it difficult to say a word.

"What is it? Too hard to form words?" Only laughing at his stupid look.

"I'm gonna c-cum!" he yelled out, biting his finger to stop himself from moaning too loudly.

"Is my little assistant really gonna cum from just the touch of my feet? How pathetic," she laughed at him, a big grin across her face.

"I-I'm cumming!" he yelled out before the intensity took over him, his body tensing up as his hot cum shot out from his cock. His legs shook with intense force as his semen shot out with intense force. Thick streaks began covering Miss Emily's stomach, some even reaching up her breasts.

After his shaking had subsided, he leaned against the table, cock still sandwiched underneath her foot, and resting his head against her leg. Faint laughter from Miss Emily and the heavy panting from Theodore were heard.

"I-I'm so sorry, Miss Emily, I just c-couldn't hold it," His stammering voice trembling as much as his legs.

"Who said you could cum?" asking him with a sharp tone.

"I-I know, I s-sorry," looking at her with guilt, the teasing grin she had before vanished, replaced with an annoyed frown.

She lifted her leg in the air, placing her foot on his chest and kicked him to the ground. Jumping down from the desk, she stood tall above him, Theodore lying on the floor as their sweat and his semen dripped down onto his chest.

"A disobedient dog needs to be punished," falling onto his stomach and pinning his arms to the floor, she glared at him with evil eyes. Slowly, she began grinding her hips against his stomach, his cock springing back to life as her wet vagina brushed against his head.

"You act so much like a pervert... I like it," she said as she bent her head down to kiss him, biting his lips as her tongue guided its way inside his mouth. Their tongues danced, twisted together like a knot. She rubbed her vagina against the tip of his shaft, whispering into his ear. "I want your cock inside me... I want your pathetic little virgin cock deep inside me," her voice laced with lust. "Time for last assignment, shove your dick inside me and fuck me raw like its the last thing you will do."

And without warning, she slid his cock deep inside her, Miss Emily wailing as it went inside. Quickly, she began moving her hips, jumping up and down, her hips slapping against his, squelching from all the sweat and semen. She lifted her torso, grabbing her breasts as she began playing with them, moaning loudly like she didn't have a care in the world. Theodore grabbed her butt cheeks as he began thrusting his hips into hers, the heat of her insides enveloping him nicely.

"Holy fuck," she cried out, her messy hair hanging down her head, over her body. Brushing it away, she stared deeply into his eyes, like she were staring him in his soul. She grabbed his head with both hands, sticking one thumb in his mouth, and Theodore stuck out his tongue for her. She grinned widely, her breath blowing against his face as she grunted. "I want you for my own," she continued. "I don't want you as my assistant, I want you as my personal fuck doll, fucking me senseless every night," her words escaped in a choppy pace as their hips slapped together, every thrust making it harder for her to speak.

As Miss Emily continued to slap her hips against his, Theodore was nearing his edge again, every thrust pushing him closer. Their bodies were trembling with pleasure. "Cum for me, fuck doll!" She growled with a commanding voice. "Cum for me you little cum dog!" She threw her head up in the sky as she continued to grunt.

Each muscle in Theodore's body began spasming, his penis, once again, exploding like an erupting volcano inside Miss Emily's womb. Each drop of semen filled her insides, Miss Emily gritting her teeth with enjoyment as she milked the last drop out of him. Her body was trembling as she continued to ride his throbbing cock. "Holy fuck..." Almost screaming as the electrifying pleasure surged through her. As the shock eased, she took a moment to steady herself, relaxing her muscles while panted heavily.

Taking a deep breath, she leaned against her desk's side, staring down at the messed-up Theodore. Her skin was shining in the sun's afterglow.

"Who could've thought such a little pervert like you could make their superior feel so good?"

Theodore didn't know what to say; his whole body was sore and drained of energy, so he could barely form a single word. They sat there for a while, admiring each other as the sun fell over the horizon. She rose from the floor, staring down at Theodore's pathetic face.

"Did you enjoy it?"

"I... loved it," he said, still a little unsure how to take it.

"Good," she smirked at him. "Then you will become a good assistant. Or should I say, fuck toy?" Both began laughing as Miss Emily began cleaning herself with her tissue, wiping off all the semen and sweat stains from her body. Her hand slipped between her legs, running her fingers between it and gathering all the semen inside her, lifted it above her head and let the thick cum run onto her tongue. "Mmm..." she hummed as she swallowed it, cleaning her fingers from the leftovers. "Sweet like honey," she joked.

"I think you should get dressed and get on home," she said as she continued cleaning her body. "You need to replenish your energy for next time, alright?"

"Y-yeah, of course," Theodore said as he stood up from the floor, his legs still a bit shaky. "Uhm, could I get something to clean myself with?" he asked after he had gathered his clothes, not wanting to put them on as his body was also covered in the remains of their messy meet-up.

Miss Emily just looked at him before she opened her mouth again and cleaned his entire chest with her tongue, twisting it inside his belly button to get every last drop. She then slapped three napkins on his stomach without saying anything. As Theodore's body was finally cleaned, he began dressing himself quickly, as Miss Emily was already dressed. He tried to comb his hair with his fingers, but it was still stained from Miss Emily's ejaculation, so he just let it be.

"So, uh... I'll be leaving now," Theodore said, waving to Miss Emily. Her lips grew into an innocent smile. "Hope I'll see you tomorrow," she waved her fingers in a slow, teasing motion. Theodore then headed towards the door, but before he left, he turned back at her again.