A hands on kind of leader...

Friday December 30, 2022

Kim stood in her boss’s office as he laid out the offer to her.

“So, it’s a promotion, both title bump and pay bump, but it also comes with a lot more responsibility. You’d have to be available 7 by 24, for whatever I needed.”

She smiled and nodded, “Of course, I understand.” she replied, it was an opportunity that she’d been hoping for since she’d joined the company. To work directly under Roger Pennrose would launch her career to the stratosphere, even if that meant giving up her free time outside of work.

“Alright, but I have high expectations, I won’t tolerate any slacking off and if I’m not happy, I’ll demote you just as quickly as I promoted you.” he said with a stern face.

“I won’t disappoint you Sir, I promise.”

“Good. Then go see the IT department to get your new laptop and phone and you’ll start first thing Monday morning.”

“New laptop and phone?” she asked inquiringly.

“Yes, the ones you have now are standard issue, but to work with me you need more secure devices. The IT group will get you all setup.”

“Ok, thank you again Sir for this opportunity… I won’t disappoint you!” she replied and then turned and walked out of his office, heading straight for the IT department.

Kim rubbed her forehead as she stared at glow of the laptop screen in the darkness of the office. She blinked a few times and squinted out over the office floor seeing no one else in the building, she glanced down at the clock on her screen and sighed.

It was well past 9 pm, no wonder no one else was in the office.

She rubbed her temples and then saved the work she had been doing before closing the laptop lid, only to grab her phone and unlock it to check for any messages from Roger.

She sighed in relief when there were none.

The last two weeks as his Management Assistant had been the hardest two weeks of work of her life. She often received messages from him late at night, well past midnight, which she had to reply two immediately, if just to acknowledge them.

The new laptop and phone weren’t helping the situation either. The security features of the devices made them hard to work with, with her having to jump through hoops each time they automatically locked, which was often. Unless she continued working on them, and if she did then the special screens that ensure no one could see what she was doing gave her eye strain and headaches, not to mention forcing her to focus directly on them to be able to see what she was doing herself.

She was about to walk out of the office when her phone rang and she saw Rogers name appear on the screen, she instantly answered it.

“Good evening Sir… Yes Sir… Not a problem at all Sir… I’ll get right on it Sir.”

The conversation was short and to the point, and when she hung up and sat back down and unpacked her laptop to start on the next piece of work he needed done.

Kim was sitting in Rogers office, his hands on her shoulders as he stood behind her, her head swimming in mixed thoughts and emotions.

A part of her wanted to stand up and leave, knowing the contact with him was inappropriate.

Most of her want it to continue and go even farther.

She wasn’t sure when, but at some point in the last two months of working as his Management Assistant her thoughts about Roger had started to drift from purely professional, to something… more forbidden.

The last few weeks had been the worst, with her dreams drifting farther and farther away from reality and into pure sexual fantasy about her boss. The last few days she’d even found herself daydreaming about him in the few minutes she had to herself between meetings and work.

“You seem very stressed Kim, how are you handling you’re new responsibilities?” Roger asked as he massaged her shoulders.

“It’s very challenging Sir, but I’m handling them very well I think.” she replied as she let her shoulders slump and she closed her eyes.

“Good, I do as well. In fact I am thinking of adding some new responsibilities to your role… what do you think of that?”

She let out a little whimper as she felt his hand slide down the front of her blouse towards her breasts, “M… more?”

“Yes, more. I mean, you can handle that right? You wouldn’t want to disappoint me would you?”

“No Sir! N…n…never… oh!” she said just as his hands found her breasts and gave them a squeeze.

“You see, my job is very stressful too… and I need someone who can relieve that stress for me. That’s going to be your responsibility from now on.”

She bit her lower lip and pulled in a large breath of air as she pushed her breasts out and then moaned softly.

“How… how do I do that Sir?”

“Well, you know those stress balls that people like to squeeze?”

“Yes Sir.”

“Well, I’ve got two great stress balls in my hands right now and I can’t think of anything better to squeeze to relieve my stress.”

Kim sat in Rogers car in the passenger’s seat as he walked around to the drivers side to get in as well. They’d just finished up a high power meeting with investors and she could tell Roger was stressed.

Instead of waiting for him to confirm it, she simply undid her top and turned towards the drivers seat to prepare for him to get in.

He slipped into the car and smiled at her, taking a long look at her breasts before he pushed back a little and then tapped his thigh.

She smiled and laid down across the center console until she was across his lap, then she unhooked her bra and let it fall to her sides as his hands came up and grabbed hold of her breasts.

“Mmmm… Sir, I can feel the stress in your hands. Make sure to squeeze my breasts good and hard to relieve it all.”

In the last few weeks she’d learned how to be the perfect stress relief for Rogers, always wearing clothing that gave him easy access to her breasts, anticipating his stress levels, and even learning how he liked her to vocalize during his stress relief sessions.

She closed her eyes and enjoyed the feeling of Roger squeezing her breasts, but then his right hand rose up from her breasts and she let out a little gasp.

This was new only for the last couple of days, but she knew what was expected. Her legs that were bent upwards on the passengers seat parted as she pulled her skirt down, then she pushed her panties to the side to let him have full access to her.

“Oh Roger, I love the way you play with my body! The way you squeeze my tits and play with my pussy makes me so horny!”

The fingers on his one hand rubbed over her pussy lips, the others grabbed hold of her nipple and twisted it.

“OH! Roger! Yes! Just like that! Yes! Yes! Yes!” she cried out and arched her back and Roger continue to releive his stress and she couldn’t be happier.

Kim leaned over Rogers desk, her ass high in the air, as his hands squeezed both of her ass cheeks.

It was the latest stress relief method she’d learned, at least the latest one that Roger had actually done. She was hoping he’d be doing the other one she’d learned recently as well and she wasn’t disappointed.

She felt his dick push up against her pussy and then slide over it a few times, “Please Roger, I know you have so much stress… don’t hold back!”

He pushed into her and her whole body exploded in pleasure, so much so that all she could manage to get out of her lips was a guttural groan as her eyes rolled back into her head.

Kim stood in front of the mural at Rogers condo as he sat in his chair, a drink in his hand. She parted her jacket and let it slide over her shoulders and on to the floor as she rolled her hips as she danced.

Relieving Roger’s stress had become a full time job for her, she no longer worried about the other aspects of her job, Roger had assigned them to other people.

Instead she focused entirely on Roger. She’d dyed her hair at his suggestion, changed her makeup and started going to the gym when he was at work. Anything to make sure she could relieve his stress.

She took a step forward and unhooked her bra, letting it fall to the floor as well as she squeezed her breast together, then another step and her panties followed suit.

A final step landed her in Roger’s lap and she pushed her breasts forward into his face, her hips rocking back and forth, as he reached around and grabbed a hold of her ass.

“Mmmmm… Yes… you grab Kimmi’s ass… you squeeze Kimmi’s…” she said in a short chopped accent.

One of his hands left her ass and moved up her body to her chest, she leaned back to give him better access and he grabbed hold of her breast and squeezed it at the same time.

“Yes! You squeeze Kimmi’s tit… you squeeze Kimmi’s ass… You play with squeeze toy Kimmi!”

Her whole body shivered as the words came out of her mouth and it wasn’t much longer before he grabbed her waist and gently pushed her off of his lap and on to the floor between his legs.

Kim then squeezed his dick between her lips and released every last drop of stress from his body.

Kimmi sat on the footstool in Roger’s apartment and awaited his return. She knew he’d be full of stress and she couldn’t wait to relieve it for him.

She had become the perfect squeeze toy for him, her short blonde hair, her heavy makeup, her tiny bikini, they were all just as he wanted them.

She’d master squeezing his dick between her lips, squeezing it in her pussy, and even squeezing it in her ass, there was no place on or in her body Roger couldn’t squeeze his dick and relieve his stress now.

But of course there was always room for improvement, she could certainly squeeze her tits together and let him slide it between them, but it was a bit of a challenge. Fortunately Roger had already made her an appointment to resolve that issue.

She frowned a little at that… Roger hadn’t made the appointment of course, he was far too busy for that. Instead his new Management Assistant had done it for him.

She’d been working for him for a few weeks now, after Kimmi had resigned and dedicated herself to being Roger’s full time squeeze toy.

That was a problem though, she knew Roger was stressed at work and now that she couldn’t relieve his stress until he arrived home, she knew he’d be looking for a squeeze toy for work too.

The statuesque blonde with he massive rack that was his new Management Assistant would make a good squeeze toy, maybe even better than Kimmi did.

She heard Roger open the condo door and come in, then close it behind him. He waked into the living room with his phone glued to his head.

“Hi Linda… You still in the office?…Good, I need the Grayson report done by 9 am, is that a problem?… Great, I’ll expect it in my inbox then, thanks Linda.”

Somewhere in the back of Kimmi’s head she recognized the conversation as almost identical to the one she’d had all those months ago with Roger as well.

But that thought never made it to the front of Kimmi’s mind as soon enough Roger was mauling her tits exactly like the squeeze toy she had become wanted him too.

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