Compliance Ch. 01

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Exec Assistant learns to follow office policy.
1.8k words
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Part 1 of the 2 part series

Updated 09/22/2022
Created 12/31/2002
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He had recently hired a new executive assistant to help with his increasingly hectic schedule. Her resume was impressive indeed and he was more than pleasantly surprised the day he interviewed her to find her quite attractive as well. The tailored business suit she wore that day did little to hide her voluptuous figure and he had found himself staring at her as she filled him in on her work experience.

That was a little over six weeks ago. It was now the third week in December and even though the holidays were near and the rest of the office seemed to be at loose ends with nothing to do, they had been extremely busy. Today was the office Christmas party and the atmosphere was relaxed. He had come in early that morning and hadn't seen her at all yet, as he'd been holed away in his office working on a project. He needed some files and he picked up his phone and buzzed her on her intercom and asked her to bring the files he needed.

He didn't look up from his task when he heard her enter, but mutter "Be with you in a sec" as he scribbled some final notes. When he looked up and saw her standing there, he was taken aback. Gone was the conservative business attire he had become accustomed to. Instead she was wearing a red velvet skirt trimmed with fake white fur around the hem and a white silk blouse and a pair of red stiletto heels.

His mouth fell open when he saw her and he stood up, pushing his chair away from him as he did. "What on earth do you think your wearing Miss Henson?" he roared. The smile on her face disappeared and she was speechless. She had never heard him speak in that tone a voice since she started working for him. "I-I-I just thought maybe it would be fun to wear this for the Christmas party" she stammered. He walked around to the front of his desk and stood in front of her. He could see a look of fear in her eyes as she looked up at him. "Miss Henson, have you not read our company policy on dress code? This hardly falls within those guidelines."

"I have to abide by very strict guidelines." he instructed, "Policy on sexual harassment is VERY drawn out! If we can't have calendars displaying scantily clad women, what on earth would make you think you could get away with THAT!" She cowered and could not believe she was being chastised so vehemently. His rage combined with his frustration over having to work so hard during the holidays and he began to lose his composure. "I have never had to deal with someone who completely had no regard for compliance to our office procedures! If I had a child and they tried this, I would know exactly what to do! I'd….. I'd…." he began to stammer. She looked puzzled at him as his eyes sort of began to look her over. "Why… I would bend them over my knee and give them a good spanking!" No sooner had those words left his lips he realized he created a grave business error.

Oddly, his words didn't shock her nearly as much as they did him. She perked up a bit and attempted to make light of his faux paus, hopefully diffusing a potential bad situation all around. "Well, if that's what it would take to make thing better, then by all means" she sassed him as she playfully strutted to his side of the desk, placing her hands on it and swaying her ass to and fro.

He couldn't believe his eyes! When the words left his mouth, he had fully expected her to respond by slapping his face or storming out of his office. This was certainly NOT the reaction he expected. For a split second he considered telling her to clear her desk out and leave the premises. But as he looked at her seductively waving her gorgeous backside at him, he changed his mind. Instead, he reached over and fingered the hem of her skirt "You do understand that this type of attire is simply not appropriate, even if it is the holiday season….and even if you do look damn sexy in it." She smirked and said, in a smart ass tone "Well Mr. Boss Man, what are you going to do? Stand there and stare or get on with my punishment? After all I did break the company dress code." Still touching the fur trim of her skirt, he slowly lifted it. He gasped as her perfectly smooth, round ass cheeks came into view. It was then that he noticed her candy cane thong. "I see you've carried the holiday theme to your undergarments as well." She chuckled and said "Ohh, I supposed you're going to tell me there is a company policy on the kind of panties we can wear?" Her insubordinate tone struck a nerve and he raised his hand and brought it down hard on her right ass cheek. Taken completely by surprise, she screeched and tried to stand up. "H-how d-d-dare you!!" she stammered. "No Miss Henson, how dare YOU speak to me in that tone." And with that his hand came down on her left cheek this time. Again, she tried to stand but he told her not to move and brought his hand down yet a third time. The flesh on her ass was tingling and felt warm. She instinctively arched her back causing her backside to raise a bit. The sight was more than he could take and he smacked her bottom one more time before speaking again.

"Hopefully, you can now see my point?"

She whimpered and bit her lip "Yes sir…I see your point"

She could feel his eyes on her, as she stood there, bent over his desk with her ass exposed to his gaze. She knew he could see the wetness between her legs and as she looked over her shoulder at him, she spread her legs more, giving him a better view of her ass and soaking pussy. She smiled to herself as she felt him lift her skirt up higher. Her ass was now completely exposed to him and she could feel his hands move across her hot, tingling skin. As she pushed back against him, she could feel his hardness through his pants. She gasped as he moved her thong aside and ran his hand between her spread legs then slid one….no two fingers inside her aching pussy.

She stood there, trembling, with her backside fully exposed, inviting him to take her. She heard the unmistakable sound of his zipper being lowered and knew she would soon get what she needed. She let out a low moan as she felt his hard cock slowly slide in to her pussy, filling her completely before pulling it back out, until only the head was held between her lips. He teased her by pausing a bit before sliding back inside. As he pushed against her, she felt the rough zipper against her tender skin and realized that he hadn't even bothered to pull his pants down to fuck her and this turned her on even more. She had to bury her head in her arms to keep from crying out each time he slammed forward against her. His hands were on her hips now, pulling her hard against him with every stroke. As she slipped her hand between her legs to rub her clit, she could feel his cock sliding in and out of her pussy.

She knew it wouldn't be long before she was cumming all over his cock. She felt her pussy start to contract as her orgasm took over. Biting down hard on her lip to keep from screaming out, she raised herself up, arched her back and ground her ass hard against him, feeling the rough zipper against her clit sent her over the edge and she started cumming. She felt him slam into her hard…so hard that she went sprawling across his desk, legs still open, her pussy was still throbbing from the intensity of her orgasm. She felt his cock slide out and could hear him stroking it, the sound of his hand moving quickly over his cum slicked cock. She felt his cock rub between her ass and squeezed them together around it and felt his cock throb and jerk as the first hot stream of cum shot out. She squeezed her ass cheeks again and undulated her hips to encourage him further. As the last of his cum shot out, she collapsed on his desk, feeling him rub his creamy cum into her skin.

She felt his body against her as he, too, collapsed on top of her. She could feel his breath on the back of her neck as they both tried to catch their breath. As their breathing returned to normal, he placed his lips against her ears and said "I think I have driven home the importance of following office procedure and expect complete compliance in the future." She smiled and said, "Yes sir, from now on you will have complete compliance and obedience from me."

"I'm glad you see it my way", he said "As a matter of fact, I believe we need to discuss this further today at lunch." That was exactly what she wanted to hear, and thoughts began to run through her mind. She turned to face him as she began to try and collect herself. Coyly she glanced up and caught him staring at her as he zipped up his slacks.

"Meet me at the parking garage around 11:30", he instructed "I'll drive my truck down to pick you up." This caught her off guard a bit, as she envisioned him driving a luxury car or a fancy SUV.

As she fixed her thong and straightened her skirt, she smiled and said "ohhh….a truck? I like a man with a big….truck." He tried to suppress a grin as he looked at her standing there before him, still flushed from the hard fucking he had just given her. His mind was already racing ahead to lunch and his cock began to stir again at the thought of what might take place. She picked up her files and turned to leave, and as she opened the door, she heard him say: "11:30. And don't be late. We have a lot to take care of."

She went back to her desk and sat down. She retrieved her compact from her purse and looked at her reflection. She couldn't help but smile as she smoothed her hair and checked her lipstick. She felt her nipples harden at the memory of his cock that only 10 minutes ago, was sliding in and out of her pussy, bringing her to a mind blowing orgasm. She had wanted that cock in her mouth so badly, but knew that if they stayed in there much longer, everyone would wonder what was going on. But today, at lunch, she would have time. She would show him just how compliant she could be.

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