SUCKING UP TO THE BOSS: A BABYSITTER'S PERIL (m+/M) *ILLUSTRATED*

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SUCKING UP TO THE BOSS: A BABYSITTER'S PERIL (m+/M) *ILLUSTRATED*

Post by bondagefreak »

PART I
SUCKING UP TO THE BOSS
A BABYSITTER'S PERIL

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Physically exhausted from his grueling 38-hour-long work week at the insurance firm he worked for, Kevin Mills just couldn't wait to get home, kick his shoes off and pop a cold beer open to celebrate the start of another weekend.

At 29 years of age, the young manager's assistant had spent the last three years working relentlessly to earn his position and his pay. The competition to climb the symbolic power rungs of the 13-story-high office building he worked in was truly quite ferocious, but our young protagonist's hard work and steadfast determination had paid off and earned him the notice of his local branch manager, Mr. Smith.



Impressing Mr. Smith had been one of Kevin's top priorities for the past six months, but much to his great disappointment, the man who pulled all the strings was usually too busy with important meetings or conference calls to notice of his continued hard work and dedication. The demands on Mr. Smith's time were quite formidable, and even as one of the three assistants who worked directly beneath him, Kevin found himself getting very little feedback or attention from his boss. Things were about to change though.


When the grey-suited, muscular, dark haired man emerged from his private office at around 3PM on Friday afternoon, the rising star of the company was sure someone was about to be fired.

After a somewhat difficult fiscal year, young Kev had seen a lot of his colleagues lose their jobs and be sent home without even a day's notice. So you can probably understand how nervous and apprehensive he felt when Mr. Smith suddenly spoke his name and motioned for him to stop what he was doing and follow him into his private office.

"In my office. Now." came the blue eyed man's stern command.


The frightened young assistant immediately rose up from his swiveling chair and made his way over to his boss' office, wondering if he had done something wrong and dreading the thought that he was being summoned only to receive the news that he was being let go.



Mr. Smith pointed towards the chair in front of his desk and ordered for him to sit.
Kevin did as he was told.

The office door was closed shut, but much to our young protagonist's growing surprise, his boss didn't sit on the other side of the desk like he normally would during official business meetings.

Mr. Smith simply walked right up to his young assistant's seated form and sat down right in front of him, on top of his very large and very sturdy-looking office desk.


Young Kevin looked up wide-eyed at the imposing, two-meter-tall figure who now sat squarely in front of him.
Even as the 44-year-old man's steely blue gaze pierced deep inside him, our nervous protagonist couldn't help but marvel at how monstrous his boss' thighs were and how the expensive grey suit he wore was stretched taut across those colossal arms and tree-trunk sized thighs of his.

Mr. Smith was a very big, very powerful man. In more ways than one.



"I've been keeping an eye on your work performance for the past six months, and I'm happy to say things are looking bright for you, Kevin. But that's not why I called you here. I have a bit of a problem, and I'm wondering if you can help me out." the strikingly handsome, suited muscleman eventually spoke.


Relieved at the knowledge that he wasn't gonna lose his job and that his dedication at work hadn't escaped his boss' notice, our power-hungry office assistant's hazel orbs sparkled at the possibility of being useful to the man who was in charge of handing out raises and promotions. This was a golden opportunity for advancement; one that Kevin couldn't possibly bring himself to refuse.


"D'you have any plans for this weekend?" Mr. Smith suddenly asked, to which Kevin shook his head and responded with a "No, Sir."

"Good." the older man huffed, sounding both relieved and a little frustrated at having to ask what he was about to ask. "Listen, I need your help. I have plans for tonight, plans that I can't cancel. But the girl who usually babysits my kids just called to let me know that she's sick and can't make it tonight. I've called a bunch of people but none of them can cover for her. Now I know that this is really last minute, but I need to find someone who can babysit my kids until tomorrow morning. Someone I can trust. That's why I called you in here, Kevin. Are you up to the task?"


Our young protagonist's eyes went wide with surprise. This was a really personal request; one that his boss would've never considered entrusting him with if he didn't trust him or hold him in high esteem. Mr. Smith didn't mention anything about a raise or a promotion, but our eager assistant knew how to read between the lines and would go above and beyond to earn this powerful man's favour.

"Yes, Sir. Absolutely, Sir." he cheerfully responded.

A relieved smile immediately lit the larger man's masculine features and a mighty big hand landed on top our young assistant's left shoulder. "I knew I could count on you, Kev." Mr. Smith spoke, much to his smaller subordinate's growing delight.



Kevin's boss filled him in with all that he needed to know, told him that he had to be at his place by 6 PM sharp and that he'd be in charge of the boys 'till he got back home the next morning. When our protagonist alerted the older man to the fact that it wouldn't leave him enough time to swing by his place and change, Mr. Smith merely apologised and made it doubly clear that he had to be at his place by 6 PM no matter what.

Young Kev wasn't particularly keen on spending the night sleeping in his office clothes, but he figured that would be a small price to pay if it meant earning his boss' favour and getting that pay raise he so badly wanted.


He knew that Mr. Smith had been married twice and that his failed unions had resulted in five boys sprouting from his very fertile loins. But aside from knowing that his kids all ranged from ages 10 to 14, and that his two oldest sons were supposedly a handful to look after, our young assistant knew almost nothing of his boss' family life.


Still, the threat of dealing with some boisterous teens didn't dissuade our rising star from accepting this very special assignment he'd received. After all, how hard could looking after Mr. Smith's five boys possibly be, he wondered, as he swiftly exited the much larger man's private office space.


Kevin didn't know this at the time, but unfortunately for him, he would be in way over his head before the night was over.



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Last edited by bondagefreak 2 years ago, edited 10 times in total.
Red86
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Post by Red86 »

Oh boy. Knowing some of your other stories, I think our babysitter is really in for a rough night :lol:
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Post by FelixSH »

Promising start. I tend to enjoy horrible teenagers.
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Post by cj2125 »

[mention]bondagefreak[/mention] Wonderful introduction! It's clear Kevin has no idea what awaits him, I would feel bad for him but if this is going to where I think is going, I'm going to enjoy a lot seeing him trying to babysit those kids
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Post by Pup »

Interesting opener for sure. Hyped.
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Post by ShadowHusky »

Very very interesting. Based on the genes given to them by their father, our protagonist may be far too over his head.
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Post by Pup Wingletang »

You've definitely whet our appetites with this opening chapter. Looking forward to where this story goes.
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Post by Ossassin »

10 to 14 year olds, you’ll be fine no worries ... however a mysterious thing known as foreshadowing has approached and warns of great peril in hubris. :D
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Post by Msueta@2 »

[mention]bondagefreak[/mention] Hey this was a great first chapter . I can't wait to see what direction this story goes in .
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Post by The slave »

great start I'm really, really curious to find out what these little teens are capable of lol
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Post by DeeperThanRed »

Kids tying up an adult seems like a promising start. I liked how cornered and nervous this chapter described Kevin, I can already imagine him as getting bested by a bunch of middle-schoolers even before their meeting, haha.
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Post by harveygasson »

Oooh fantastic and intriguing start! Looking forward to the second part
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Post by KidnappedCowboy »

Uh! Oh! Looks like Kevin Mills is going to have his hands full...excuse me...his hands tied! :lol:
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Post by Socksbound »

Fantastic start, Kevin is about to be in way over his head. Your introductions have a way of sucking me in, with only slight hints as to what will happen, leaving my imagination to do the rest ;) :twisted:
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Post by Xtc »

'Sucking up', huh? :evil:
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Post by MaxRoper »

Well obviously our Kevin has no idea what happens to young twinks in [mention]bondagefreak[/mention] 's stories. I have a feeling he's about to find out.
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Post by sniffingyoursocks »

What an introduction - I can't wait to find out more about poor Kev's looong night awaiting him.
Haha, poor babysitter...amazing work as always, Sir [mention]bondagefreak[/mention]
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Post by Trainedsub »

I have to say, my mind would be racing if a big muscle daddy sat directly in front of me and said he needed a personal favor. My mouth would be watering 😂
Please sir... Not that again, I promise I’ll be good-
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Post by luiggi87 »

The beginning is so promissing that honestly I am just struggling in anticipation for next parts. Great job as usual
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Post by bondagefreak »

Wow! Thanks so much guys. This was originally intended as partial fulfilment of a story request made by [mention]lee4sox[/mention], but I'm positively thrilled at seeing so many of you intrigued by what Mr. Smith's kids have in store for their impromptu babysitter.

Hope you enjoy the next part, folks!

[mention]Red86[/mention] [mention]FelixSH[/mention] [mention]cj2125[/mention] [mention]Pup[/mention] [mention]ShadowHusky[/mention] [mention]Pup Wingletang[/mention] [mention]Ossassin[/mention] [mention]Msueta@2[/mention] [mention]The slave[/mention] [mention]DeeperThanRed[/mention] [mention]harveygasson[/mention] [mention]KidnappedCowboy[/mention] [mention]Socksbound[/mention] [mention]Xtc[/mention] [mention]MaxRoper[/mention] [mention]sniffingyoursocks[/mention] [mention]Trainedsub[/mention] [mention]luiggi87[/mention]
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Post by bondagefreak »

PART II
SUCKING UP TO THE BOSS
A BABYSITTER'S PERIL



Kevin left the office about three minutes past five o'clock, and immediately set course towards his boss' relatively posh suburban neighbourhood.

He swung by a small convenience store along the way and picked up a toothbrush and the few other essentials he would've normally brought with him had he known he would be on babysitting duty for the night. Thankfully, there wasn't too much traffic on the road, and he arrived at Mr. Smith's place with a few minutes to spare.


As soon as he parked in the roomy front driveway and rang the doorbell, our 160-pound office assistant was immediately greeted by his much heavier boss and introduced to all five of the kids that shared the luxurious dwelling with him.

Ben, Lewis and James were in their first couple years of high school, whilst Nicholas and Tim were obviously the youngest of the bunch. Our eager-to-please babysitter couldn't really bring himself to care about who was who or what the particularities of each boy was. All that mattered to him was earning their father's favour and the only thing he could think about at the time was getting a pay raise. Everything else came in distant second.


"Alright, you boys behave while I'm gone. Timmy, I want you in bed at ten. The rest of you, eleven max." Mr. Smith told his kids, after giving his office assistant a tour of the house and handing him a fair amount of cash so he could order out.

The boys waved their dad goodbye and watched as the dark-haired businessman entered his BMW and drove off into the night.


29-year-old Kevin was supposed to be babysitting the kids, but before the night was over he would being babysat by the bunch of them. Mr. Smith had somehow failed to warn him that four of his sons were boy-scouts and that the three oldest ones were fully trained in the ways of complex ropework and intricate knotmaking. His boss either didn't know, or he didn't factor that in when he left Kevin in charge of them.

But of course, our young office assistant had no idea what sorta danger he was currently in.
Yes, Mr. Smith's three eldest sons were surprisingly tall for their age, and yes two of them had a reputation for being somewhat fierce and troublesome. But much to our naïve protagonist's immediate surprise, the bunch of them proved quite friendly and accommodating once the man of the house had departed for the night. So much so that Kev soon found himself enjoying a double order of extra large pizzas while his hosts peacefully played video games on their living room console.

This was gonna be a piece of cake, he thought. In a few hours, they'd all be tucked in their respective beds and his job here would be done. He could already see Mr. Smith summoning him to his office to deliver the news of that much sought-after promotion he so badly deserved. More importantly though, he could already see the extra money lining his bank account as a result of it.



Everything was going well at first, but our rising star's stroke of luck was about to run dry when one of the teenage boys got tired of gaming on the console and suggested playing a round of the "escape challenge" game they sometimes played when their dad wasn't around.

Kevin watched as one of the older boys returned to the living room with an impressive quantity of rope and looked on rather intently as his hosts went about trying different knots on each other and horsing around like young teens normally would.


When Lewis finally suggested he should be tied up and initiated to the escape challenge, our uninterested babysitter chuckled amusedly but politely declined the offer.

Mr. Smith's kids were very persistent though. They went on and on about how fun it would be to have a grown man take part in their game and they taunted Kev with the notion that he was too afraid he wouldn't be able to get out of their knots in a reasonable amount of time.


The boys rejoiced when their babysitter finally acquiesced and agreed to play the silly little game with them.
Their prey had taken the bait; hook, line and sinker. What a dumb babysitter their dad had found for them, the kids thought.



"Alright, so the game goes as follows. We tie you up a little and you have half an hour to try and free yourself. If you free yourself on time, you get to try your hand at tying up the person of your choice and making them go through the same challenge." Ben explained.

"Okay, but what happens if you don't get free on time?" Kevin asked, rolling his eyes up and not sounding particularly impressed at the simplicity of this "game" they insisted on playing.

"Nothing. You're just given more time to escape, but don't get to tie anyone up the next round." one of the other boys chimed in.


"Alright, sounds simple enough." the grown man answered.

"Oh yeah, and one last thing. Since this is your first time, we're going to give you a choice. We can make the challenge very easy for you, we can make it medium-hard, or we can make it pretty darned difficult. Your choice." thirteen-year-old James told our protagonist.


Not really knowing what to expect, but still being a grown man in his prime, our young office assistant would've felt kinda silly asking twerps half his age to go super easy on him. So he chose the middle path.

"I'll take the medium-hard option, I guess." he finally answered, causing all five boys to rejoice and congratulate him for not having taken the cowardly route.



Our blond-haired babysitter quickly started pulling his tie off in the hopes of getting more comfortable for the evening, but he was immediately stopped when one of the teens requested he stay fully dressed for the little ropework session they were gonna put him through.

"No! Keep your tie on." Lewis objected. "Put your suit jacket back on. Haha! You'll look like a captured detective or something."

"Speaking about captured detectives, I got a great idea!" one of the other boys immediately laughed, before scampering out of the living room and into the privacy of his father's bedroom.



The office assistant rolled his eyes up again, but did as he was told; fixing his tie back up, putting his leather dress shoes back on and donning the well-tailored suit jacket he'd worn to work during most of the day.

Kevin Mills was once again perplexed when one of the teens he was babysitting returned to the living room holding a pair of gloves and a very large, very heavy-looking leather jacket in his hands.

"Here, put this one." the kid instructed.


Kevin didn't understand.
"What? Why?" he asked, realising that the brat was holding up what appeared to be the big leather coat and gloves his dad usually wore during his daily drive to and from work.

"'Cause, silly. It'll fit the snooping detective personae even better with this stuff on you." Ben quickly explained.

"Besides. The gloves will protect your wrists from getting rope burns and the jacket will keep the rope from digging into your skin." a younger voice chimed in.


The 29-year-old office assistant had never been tied up before, but clearly those kids knew what they were talking about. So after letting out an exasperated huff, the blond man begrudgingly went along with their stupid game and put the older man's clothes on.

The leather jacket he was told to put on over his suit attire was very thick and very heavy.
It filled Kev's nostrils up with a very strong and somewhat distinctive odour that he couldn't ignore. And much to his continued annoyance, it was also much too big for him; which wasn't all that surprising considering how broad-shouldered and tall Mr. Smith was.


Ben immediately walked up to his compliant babysitter and zipped his dad's jacket up to almost all the way before buttoning the leather wind-flap shut. The jacket's sleeve cuffs were tightened around the scrawny man's wrists and the predatory kids watched eagerly as their unimpressive prey item slid his hands into the thick leather gloves they'd fished out for him.


Kevin thought he looked ridiculous, but his cheerful hosts assured him he looked like an undercover agent with his suit and tie still on and their father's heavy duty leather coat on top of it.


They lured him to the room where the escape challenge was apparently gonna take place, and set in motion their plan to keep him trapped there for the remainder of the night.


Kevin Mills had NO idea what he'd just gotten himself into.
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Post by The slave »

great excellent suite even if me personally in his place I would have chosen the most difficult choice by taunting them that I could be free very very easily lol
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Post by Volobond »

Hook, line, and sinker - these young fellows know what they're doing!
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Post by cj2125 »

[mention]bondagefreak[/mention], love the detective in peril angle this is taking! Hope they keep up that pretense even if it's obvious they have other plans in mind. Can't wait to find out what awaits him!
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Post by Pup Wingletang »

The suspense is killing me! I love how easily they have manipulated Kevin, even getting him to dress up for the 'game'. People always under-estimate children. I think he is going to learn a valuable lesson about the perils of trying to suck up to your boss!

Loving the banner for this story [mention]bondagefreak[/mention] .
A pup is for life but especially for bondage so get out the sleepsack and muzzle.

Don't miss out on the final chapter of Lovingly Zipped Up (M/M)

All my M/M stories can be found HERE.
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