Story 17 #3
“What did you want me to do, to start?” she asked, as doe-eyed as always. He thought for a moment. He had a stack of papers that he had set aside for her throughout the day, to fax or to shred. They were separated accordingly into two piles, each one held together with a binder clip.
“I have these papers. The ones with the red clip get faxed. Each one has a sticky note with the fax number on it. The ones with the blue clip get shredded. The fax machine is in the hall on the way to the elevator, and the shredder is downstairs near the secretary.” He handed her the two stacks. “Please make sure to take the sticky notes off and recycle them before you scan them in.”
“Did your last assistant… not do that?”
“Oh, he didn’t, no. There’s a reason we had to hire a new one,” he chuckled. “Good luck.”
The faxing and shredding only took her half an hour. She came back with the originals of the faxes without being asked and handed him the blue binder clip. He tossed it in his bottom left drawer with the rest of the various clips. “Thank you, Ms. Rasmussen. Now, could you file these originals away in that filing cabinet?” He pointed to the filing cabinet behind his desk. “Fax originals are bottom drawer, sorted by date.” She quickly did as asked.
She bent down to reach the bottom drawer and pulled it out, thumbing through the other faxes to reach the very back. He stared, watching the shape of her bottom as she bent forward. He felt the beginnings of an erection. She closed the drawer and turned to look at him. Surely she had felt his gaze. There was no way, he thought, that she did not receive those kinds of stares from men his age and older on a daily basis. With her relatively small stature and the firm roundness of her bottom and breasts, she had almost certainly been the subject of male–and probably also a smaller fraction female–attention over the years. Her shyness indicated that she would not say anything, but he was proven wrong. She turned slightly red.
“Mr. Hutton, were you just staring… there?” She did not seem unsettled or uncomfortable. Her shy soft tone remained, and her gaze was focused on the ground. There seemed to not be a point in lying.
“Yes, Ms. Rasmussen, I was.” He would have been more embarrassed if she had been uncomfortable, but she was smiling slightly. His erection grew harder. “Is that a problem?”
“No, sir,” she smirked shyly. “It’s not a problem at all…”
“Good,” he said firmly. “You should do it again, then.”
“Yes, sir…” She turned around in front of him so her bottom faced him and slowly bent over. The shape and visual texture of her bottom caused him to get fully erect. He stood up and placed his hands on her hips, rubbing his erection between the cheeks of her buttocks. The sensation was almost enough to make him cum right then and there. He stopped. He could not afford to stain his suit pants that way. “Aww, why’d you stop?”
“There are better ways to do that. Less messy,” he said. He pulled out his wallet and produced a condom. It had not been there long, so it was not worn out or unsafe to use. He unzipped his suit pants and pulled his erect cock out of the front of his boxers. He tore open the condom and rolled it down to the base. It barely fit down to the base of his eight-and-a-half-inch member, but it covered enough to keep them both safe, just in case.
He sat down on one of the smaller chairs in front of his desk, looking at her expectantly. “Well?”
“Y-yes, sir,” she said. She removed her shoes, which were formal-style flats, and carefully lowered herself onto him, facing him. He pulled her panties aside and guided himself in, slowly thrusting upwards. She was warm, wet, and tight.
“Is this your first time?” he smirked, gently easing himself into her. “You’re so damned tight…” The walls of her pussy hugged his cock firmlyhi, exponentially increasing his pleasure. It felt as though he would cum in her instantly.
“Y-yes, sir.” She moaned slightly and bit her lip to keep from arousing any outside attention.
“Aww…” He turned his thrusts into a more rhythmic pattern, shoving his cock as deep inside of her as he could. She bit down harder on her lip. He could feel his balls roughly slapping against her rear opening. “Your first time is with your daddy’s friend, huh?” She could not answer, biting down as hard as she could on her lip without breaking the skin.
He placed his hands on her waist for leverage, thrusting himself up harder and harder until he felt his cum spurting out into the reservoir of the condom. He twitched and throbbed inside of her for a moment, steadily leaking semen into the protective barrier for about 10 seconds. He gently eased her up off of him. She adjusted her panties and straightened out her skirt, slipping her shoes back into her flats. He pulled the condom off, tying the end of it off into a balloon-like knot, and threw it, along with the wrapper, into the garbage can beneath his desk. No one except the custodial staff would see it, assuming they looked into his garbage at all while emptying it.
He looked up at the clock on the wall. It was already 25 minutes to five. “Y’know… I’m the boss and technically I can leave whenever I want. I’m salaried, not hourly. I answered all my emails and had you fax and shred everything that needed it. If you’d like, you could meet me in the parking lot and come home with me?”
“I wish I could tonight, but I have to study,” she said, obviously disappointed. He could tell that she wanted to go home with him and spent the night with him. He could drop her off at her college in his car and all her friends would see her and ask who the “old guy” in the fancy car was. It would be gratifying for him and embarrassing but amusing for her.
“Well, that’s too bad…” He thought for a moment. “Surely, you don’t have to study on Friday nights?”
“You’re right,” she smiled. “I don’t have any classes on Friday and obviously not on the weekends.”
“Mm… maybe you could home with me after work on Friday, then? Spend the night on Friday and maybe through Saturday? Do you still go to church on Sundays? I could drop you off.”
“I still go to my parents’ church...”
“Excellent. Would you like that, then?”
“I dunno… how do you think they’d react to seeing you drop me off? Wouldn’t it look suspicious?”
“Mm, you’re right. I could drop you off down the block and then you could walk up to the steps yourself?”
“That sounds better,” she smiled.
“So Friday night and all of Saturday are good for you?”
“Yes, sir,” she smirked.
“Well, then… it’s a date.” He took his hat and overcoat off the rack in the corner of his office and put them both on one at a time. He put his laptop and several papers into his briefcase and turned out the light to his office. “Stick around until five. Ask Laurie on the ninth floor if there’s anything she needs help with for the next 20ish minutes, okay?”
“Okay.”
“Good.” He nodded and opened the door, letting her out first before closing it and locking it behind him. He headed to the elevator, nodding at the CFO on his way through the hall. He pressed the button to summon the cab, and it arrived almost instantly, which was about usual for this time, as everyone left at five and not 20 minutes to five. He had beaten the rush. He stepped in and pressed the button for the ground floor. It moved down at 150 feet per minute, taking about 45 seconds to reach the ground floor. He walked briskly out the door and headed for the parking lot, pulling his keys out of his pocket and jingling them until he got close enough to his car to double-tap the unlock button on the key fob. He routinely tossed his hat, coat, and briefcase into the passenger seat and drove home, this time in silence.
The work week went at its usual pace. Every day, Jodie would come in for two hours, from three to five to fax and file his documents, answer his phone when he was preoccupied, and shred any papers that needed to be shredded. On one occasion, he sent her down to the Starbucks down a couple blocks away, with orders from all four C-level executives for their afternoon pick-me-up. He sent her down there with his company debit card and instructed her to also get herself something. She came back with all the correct beverages, as well as a small treat for herself. Overall, he thought, she’s a great assistant. It’s not like I only hired her to fuck her. He was unsure to whom he felt he needed to justify himself, and yet he thought this anyway.
After several days of satisfactory work, Friday came. As usual, she came dressed to the nines in her most professional clothing. She arrived promptly, five minutes before nine. Today, she had brought him the same coffee order as last time without being asked. “Thank you, Jodie,” he said, taking it from her and removing the green stopper. He took a sip and sighed. As usual, it was ordered and made correctly. He gave her a gesture of approval with the cup, taking another sip from it. “Delicious.”
“What do you need from me today, Mr. Hutton?” she asked, with a sweet lilt to her voice. Each day, she had arrived eager to please, and today, it seemed, was going to be no different. He pondered her question carefully.
“Well, I have these papers that need to be faxed, with the fax numbers stuck to them, as always.” He passed her the stack of faxes. “After that, come back and file them away, and then I’ll tell you what to do after that.” He smiled at her. She took the stack of faxes and left, practically skipping away. He reopened her work laptop and began answering emails from clients. Maybe I can train her to do this for me, too, he thought. Emails were by far the most tedious aspect of his job.
After about half an hour, Jodie came back and filed the original papers away, as he had instructed. “What would you like next, Mr. Hutton?” she asked.