Her Little Assistant

Story by Joshiah on SoFurry

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#11 of Macro/Micro Stories

When he's invited to come on a business trip with his manager, Shannon, Jacob doesn't think too much of her invitation...but in this story for Irving, we find out that there's a lot more in store for the tiny fox than dinner and drinks!

After helping her through all of her presentations and business meetings, Jacob is sure that he's proven himself a useful asset to Shannon's team, and the company at large. He's right, and Shannon admits the same, but she's just as excited to show him her admiration in a private setting as she is at the hotel bar.

Jacob can hardly believe what he's seeing when his manager drops her panties and fishes out a vibrator from her belongings...and a piece of string is going to make sure that he's along for the ride!

-

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As always, read, comment and enjoy!


When Jacob heard about the way that his boss lived, he believed her, but he didn't think he'd be getting a front row seat to her lifestyle, and certainly not in as much earnest as she was offering him.

"You did a fantastic job out there today, kid. I'm _genuinely_impressed."

Working directly under her in the office, both literally and figuratively, no one would have blamed Jacob for being intimidated by Shannon: if she were too clumsy, she'd end his entire existence with a single, awkward landing of her foot, but then, she didn't do anything halfway, and there was nothing sloppy about her movements.

For the sake of safety regulations, Jacob's desk was on something of a mezzanine level, to prevent unfortunate accidents, the same as the rest of the micro-sized critters that worked in the office. He was one of the only micro-foxes that they'd ever hired, and from day one, he'd been picked on by Shannon...figuratively, at first, but when she found him to be fantastic help, she took him on as a personal assistant.

She refused to go on a business trip without him, and though she continued to dazzle Jacob with her impressive work ethic, he was getting a glimpse into the finer points of the executive lifestyle, as well.

"All I did was feed you some notes and help keep your presentations going," Jacob suggested. While Shannon rested her elbows on the bar and leaned over it, Jacob sat on the bar, near to her arm, and drank from a normal shot glass as though he were chugging from a bucket. "You were the one that everyone was watching...and I'd say they were pretty convinced by the numbers you presented."

A typical sales conference meant that plenty of executives were just there to schmooze, but Shannon was there with proof-of-concept to be displayed for prospective investors: after putting on a presentation that might determine her increased salary in the coming fiscal year, it was only natural that she needed a stiff drink.

After helping keep her on point all day, it was reasonable that Jacob needed one, as well...but in that regard, his size made him a cheap date, and the nerves of being around so many bigwigs was keeping the fox from embracing the subtle, tipsy nature that the alcohol encouraged.

"You don't have to butter me up like the investors do, you know," she reminded him. "You're one of the few people brave enough to speak to me with an honest opinion; do you really think I did a great job out there, today?"

Shannon rarely let her walls down in the office, and she never let them down on the rarer occasions that she'd spend a night at the bar with the rest of the floor staff.

This was a business trip at a distant location, and Jacob was the only one she had to worry about...but there was still a shift in her tone that he'd never heard before.

"Trust me, boss...y-you did a fantastic job," he reiterated. "I'm just glad I was able to be of any help."

It was refreshing to be treated with genuine, hesitant honesty: she took some solace in knowing that Jacob actually thought his answers over before blurting them out.

"Thank you, Jacob," she murmured, her lips halfway over the edge of her glass of wine as she gestured for another pair of drinks. "But don't sell yourself short...no pun intended."

Rare as it was to have a chance to snicker at his boss, Jacob couldn't help himself. "You sure about that?"

"Would've been too easy," she claimed, grinning around the rim of the glass before a final sip drained the last of the tasty, fermented grapes. "And speaking of taking things easy, you know you can call me Shannon, right?"

Their office wasn't terribly far from the coast to begin with, but there was a different atmosphere to be had at a sales conference.

Shannon knew that all too well, but for Jacob, it was the first time he'd been able to see a bar that was stuffed to the gills with people that looked like they were dying to get out of their business casual clothes and into something more comfortable.

Whether that was a more comfortable outfit, a more comfortable room, or just letting themselves go with a night on the town, there seemed to be a silent understanding that whatever happened that weekend was simply going to happen, and come Monday, they'd all be back at their respective buildings, content to keep those memories close to their hearts, save for the occasional 'you just had to be there' anecdote.

He never once imagined he'd find himself in the middle of one of those anecdotes, much less to become the source of one.

"Sorry; I...I just can't help it, bo...I mean Shannon," Jacob's lips quivered with the weight of saying her first name so casually. "I just want to make sure that you know that I respect your position and all that...one of the last things they taught me in business management was that you couldn't be friends with the employees."

"How many other things that you learned at your business college do you actually use on a daily basis?"

That Jacob had to think about his answer at all created a pair of sucker punches: the first was his realization of just what a waste of time his college days had been, but the second was that he didn't use anything he'd learned in his current position, and even less of that, he'd retained.

"Well, you've successfully helped me figure out that my college days were a racket," he muttered, lifting his shots glass to his muzzle again. "Cheers, Shannon."

"Would you look at that: you do have a little more personality than being the cute, little guy that smiles at everyone so they don't eat him," Shannon teased. She took the next glass of wine presented to her and clinked it to his own shot glass, moving delicately so she didn't force his drink to spill all over him. "But I'll cheers to the fact that, through whatever cosmic means, you going to that business college meant that I was lucky enough to end up with the best professional assistant a girl could ask for."

In the office, they were cordial enough and even what some would consider friendly, but Jacob was always fearful of being a suck-up, and for her part, Shannon didn't have a thing to worry about, short of giving the micro-fox the wrong message.

Normally, that was as simple as keeping their relationship office appropriate, but with every sip of wine she took and every side-eyed gaze that they shared, she was trying to be subtle about dropping the same hints she'd been dropping over the past few years.

Maybe it's a matter of perspective, she thought. From down there, maybe it just looks like I'm glaring at him, instead of giving him a come-and-get-me stare...

"You're really too kind, b...Shannon. Sorry."

"Don't apologize."

Jacob snickered and looked into the rim of the shot glass. "I do that too much too, don't I?"

"More often than you need to, anyway," Shannon admitted. "I appreciate your candor and professionalism in the office , Jacob, but we're on a business trip and you're still acting like the RM is breathing down your neck."

"You've never been in that position?"

"What position?"

"The one where you have to act as professional as possible because you're alone with your boss, and God forbid you let something stupid or offensive slip, and then you're stuck as a desk jockey for the rest of your life?"

Shannon blinked. "You really think that I'd keep you on the mezzanine for the rest of your life just because you slipped up a little bit?"

She didn't have a reputation for cruelty...at least, not that she knew of. She immediately took another swig of her wine, hoping and praying that she hadn't given that kind of silent signal to the tiny fox.

"Nah...I don't think you're the type," Jacob admitted, smiling inwardly. "You're too kind for that, but I'd still rather play on the side of caution, y'know?"

It was rare that simple flattery was enough to make Shannon take pause, and rarer still that she flushed at the words of a coworker.

No doubt, the wine was helping to loosen her up, but of all the handsome men that worked on her floor, Jacob was the only one who ever appealed to her, even when they were theoretically incompatible, on size alone.

"That's one of the kindest things anyone at the office has ever said about me," Shannon admitted, knowing the subtle flattening of her ears would betray how casually she tried to reply.

Jacob was worried to see the non-verbal expression of her emotions, but there was still a tiny smile in the corner of her mouth, and at his size, it was the smallest details that had the most profound importance.

"You were the one saying that I shouldn't act like I'm at the office right now, right?" he reminded her, trying to offer her a comforting gaze and hoping that he might capture her stare again. "Well...for what it's worth, Shannon, it means the world to hear you say that you think I'm such a great assistant. I guess I'm lucky to be one of the rare people out there who can say that they really like the person they work for."

The micro-fox was adept at saying a lot more than he realized, in as much that his profundity betrayed his small, soft-spoken nature.

He knew the power of words, but he never would have guessed that such an honest and timid admission would be the lynchpin to completely change the direction of their heartfelt conversation.

"You know...you're right, Jacob: you shouldn't be acting like you're at the office right now, and neither should I," she reiterated, realizing that she was the one betraying her own idea. "We're the only ones here from our branch, we're sharing a hotel room, we've got the rest of the weekend to do whatever we want with, and this bar is our oyster."

"So you are capable of relaxing and loosening up," Jacob turned the tease back on her. "Though...I hope sharing the room with you isn't too much of an inconvenience...I've seen a lot of handsome felines watching you from down the bar."

The tigress narrowed her gaze at him once more, but this time, she leaned over her resting elbow, making sure the vulpine was level with the intensity and desire in her look.

"I said we're sharing a hotel room," she repeated. "Not some random guy that I decided to sleep with because I know I'll never see him again; that's not really my style, Jacob."

If not for the drink in his lap, he never would have been able to find such a snappy, clever response, but the usual bundle of his nerves was being suppressed just enough: "What is your style, then?"

He immediately realized what he said and lifted the drink to his muzzle, sure that his career would be coming to an end, whether by firing, or by the blind fury of a sensual tigress.

"I guess I've never shown you how I like to unwind after one of these conferences, have I?" she thought aloud, her eyes keeping him pinned to the bar with the weight of her stare. "I regret not inviting you to one of them sooner, Jacob...you've been wonderful company, but your presence has complicated things just a little."

He was nearly biting the rim of the shot glass. "H-h-how so?"

"Well, I can't unwind the way I normally would with someone else in the room...but if you're sure you don't mind-

"Nu uh. Nope. Not at all."

She giggled at his overwhelming nerves. "Then I'd love to show you how I relax when a long day of work is through...and it's got nothing to do with other felines."

Jacob knew there was no right answer: he could read between the lines enough, even if he couldn't feel the lust in his manager's gaze.

What he didn't know was that there was no wrong answer, either.

"If I say no, a-am I fired? What if I say yes?"

"I say you come back up to the room with me; it's getting awfully late," she noted. "And if it's too much, just say the word."

"Will you even be able to hear me, all the way up there?"

Her ears twitched and tilted to the adorable squeak of his voice. "I listen very closely to my subordinates, Jacob. You know that better than anyone."

From there, she could hear his heart racing...and the quiet, panting fear that left his lungs in shallow, rapid breaths.

"How would we-

"You just let me worry about that."

**

There were plenty of people who traveled with sex toys: that would have been a revelation to someone like Jacob, who just had to worry about cleaning himself up after having his fun, but for someone like Shannon, a pair of fingers would only take her so far.

"...That's...extremely pink."

The toy was such a stereotypical pink color that even Shannon herself found it a little gaudy, but there were indents on the base of the toy, left behind by her grip; she knew exactly where she needed to hold it and at what angle to get herself off, but she wasn't afraid to admit a few things to herself.

First, those business trips where she did score a man were far more enjoyable than those where she was forced to resort to using her toy...but second, and more prevalent, she'd been hoping that she'd have a chance to try this particular idea for quite some time.

She couldn't remember exactly when she first thought about sitting on a vibrator at her desk, but right along with that thought came the curiosity of what it would be like if she could somehow enhance the toy: she didn't want Jacob to feel reduced to that, but they both knew the kind of risks involved in fooling around with a coworker, especially when the separation of powers was involved.

"Wait til you see where it's going," she answered boldly. "Might redefine how you feel about that word."

There were panties under the tight guise of her slimming, professional skirt, but they'd already been pulled down and kicked to the edge of one of the beds in their hotel room.

Even before Shannon made her intentions completely clear, she'd conveyed enjoy for Jacob to realize that they wouldn't need both beds that night, but the obvious issue of their differing sizes left him curious, if a little fearful of just what she was planning...and if she needed to, she wasn't afraid to pull rank on him, even as a playful joke, to get him to agree to her idea.

Whether it was for fear of losing his job, or simply knowing that she could overpower him with a single paw, Jacob found himself without the tiny business suit that he'd arrived in, and a hair-tie of black was dangling in front of the brilliantly pink toy.

"Shannon, a-are you planning to...I...uhm. Actually, I've got no idea what you're planning to do."

She giggled at his oblivious nature: she thought dangling the tie in front of the toy would be enough.

"Jacob...let's just...let's pretend that you already know how I feel about you," Shannon cut right to the chase, unable to stifle the quiet purr that rode her every word. "Let's pretend that I've already told you how I fantasized about riding you, and...let's pretend that's even viable for us."

The timid micro felt his eartips burning as his entire head flushed with disbelief and bashful energy.

"Now, let's pretend that I've told you all about how hot I thought it would be to sit on my vibrator at work," she continued, "And...how much hotter it'd be if you could actually be a part of that experience for me."

She was sitting next to him on the edge of the bed, but at his range, there was no missing the scent of her arousal...but that delicious aroma was going to become his existence, before too much longer.

"I feel like I'm coming on a little too strong."

"It's a lot to take in," Jacob blurted out, but he immediately glanced aside. "I...m-maybe it's the alcohol talking, but it's not like I haven't thought about this...a-about you."

His specification was enough to leave Shannon feeling bashful in turn, but it stirred even greater excitement within her to know that he felt, at least on some level, the same way about her.

"And let's say that you already knew how I felt, and h-how excited I was to finally be picked to go on a business trip with you...and t-that I'm terribly nervous about screwing this up-

"Trust me; I'd noticed that last bit," she teased.

"What do I do, then?" he asked, looking genuinely concerned, behind his obvious excitement. "How do I not screw this up?"

They were rushing into bed too fast; Shannon knew it just as well as Jacob, but neither one of them could stop what they'd already started.

The poor fox was stripped naked and feeling vulnerable, and in their working relationship, she knew his greatest comforts came in feeling useful to her: that was enough information for her to go off of.

"You do your best to relax," Shannon explained. "You let me tie you to this toy...and then...you just sit back and enjoy the ride as much as I know I'm going to."

Setting the toys aside, Shannon leveled the playing field a bit as she stood up and pushed down quickly at the pencil skirt, wanting Jacob to feel like he was on her level, rather than beneath her.

Little by little, she'd have to work him up to that concept, but there was no doubt that she was in control all the while as he looked to the toy and the hair tie.

"This is really kinky," he said, bewildered at what he was about to do...but if this was his only business trip with her, he wanted to milk all the mileage he could out of the experience. "Are you s-

"Damn sure," she read his mind and stopped him before he could rouse any doubt, and her grip around his tiny body silenced any further questions. "Now...that was one hell of a performance this afternoon, right? That's what you said before?"

He nodded silently and gulped, feeling utterly helpless...and yet, comforted in her grasp.

"Like I said before, I couldn't have done it without you," she reminded him, as she worked the hair tie over his torso in a couple of tight loops, making sure he wouldn't come loose inside of her. "That's...g-gonna be true about this performance, too."

Arms bound to his sides and body stiff against the toy, Jacob realized that one aspect of his excitement couldn't be hidden: the flesh of his cock was standing firm at the idea of being used as a living sex toy, and the rapid descent into depravity with his manage was ticking off so many boxes from the fantasy that he was living out.

He didn't want it to be a one-night stand, no matter what came next...but he was still terrified of living up to her expectations when his eartips grazed her petals.

With each little nudge, she pushed more of the vibrator into her womanhood, and Jacob winced his eyes shut as he slipped into the gap with the toy, feeling her juices spill over him in such volume that he couldn't doubt her arousal any longer.

It was doing wonders for his self-esteem.

This is really happening, isn't it? He thought, as he held his breath and squirmed against the clever bondage of the hair tie. I'm...literally inside of her...I'm fucking my own boss!

It was a secret that would be easy to keep: no one ever would have believed what he said, and he couldn't believe the pleasure he felt as the tip of his cock kissed along the top wall of her womanhood, all the way through that first pass.

Delicate, slick flesh kissed around the head of his member with each subtle, slow roll of her wrist, and from inside, he thought he could hear her moaning on the outside, enjoying the act just as much as he was.

He only wished he could tell her the same, but there was no way for him to sync with her delight, or to know if he'd outlasted her.

"O-oh...you actually fit!" she cheered, giggling against the headboard and pumping her wrist a little faster. "I was worried you might be a little too big, Jacob...b-but you're...perfect for me..."

A fox dating a tiger was already considered untraditional, and a personal assistant dating their boss was completely forbidden...but those words, however distant they sounded, rattled over Jacob's swimming thoughts as he was eased back out of her passage, soaked from head to toe with the plentiful, glistening juices of her arousal.

"Just having you inside me almost made me cum," she admitted, as she rested the underside of the vibrator against her clit. "Fuck...w-why did I wait so long to invite you on a trip with me?!"

They couldn't blame the alcohol for their lust, and couldn't blame the atmosphere of the conference, either: they were accepting, slowly but surely, that this would have been their experience if they ever went to bed together.

Those extra elements only sped the process along.

"Does that mean...mn..mlm..." Jacob paused to lick some of the excess from his own muzzle, unable to speak through the sheer mess she'd left upon him. "T-that you'll be taking me with for the trip to San Fran next month?"

"Next week ," she corrected him. "You think I'm waiting for another conference to fuck you again?"

His ears flattened with timid nerves, just before she dipped him back into place and turned on the vibrator, giving new life to her inner muscles and forcing them to milk against a cock that couldn't hope to stand up to such a treatment.

Jacob knew the delight of a tight, inner grip as a woman came around his member, but women his own size would never be able to stack up again...not when Shannon's body was able to massage his arms and legs with all of the talent of a professional therapist, all while stroking his cock from angles that he'd never even conceived of before.

He just wanted to try to give her a memorable performance, but he didn't know for sure that she could even feel him; she was all too happy to clear that up for him with the first, milking quiver of her inner muscles, but words quickly followed, as her wrist hammered the toy rapidly, deeper and deeper within.

"Fuck...y-you're so hard...and that wonderful cock is hitting all the right places, Jacob...y-yes... yes ; keep fucking me, Jacob!" she cried out, not giving him a choice in the matter of her request.

Only his feet ever made it back out of her petals from there: she was pummeling herself with the vibrator and stroking Jacob off in the most unique way he'd ever experienced before, but it wasn't just the novelty of the act that was so incredible.

The sponge of her g-spot was tender and smooth against his tip, and even before she released the velvety warmth of her own climax, she was certain she felt a new heat spreading across the top wall of her vaginal passage...and she was right, as Jacob's cum spilled back into his own fur, joining the mess of juices that bathed his smaller figure.

"Cumming inside y-your own boss...w-what...what would my boss say about that?" she panted, shivering against the bed and pushing the toy as deep as she could reach, ignoring the internal flutter of muscles that tried to push it back out.

She knew she was squirting just a little when she felt the gush of her juices splashing against her own wrist, but as her whole body seized and her limbs stayed taut, she felt as though her mind was leaving her mortal coil to its own devices; such pleasure was greater than she could hope to contain or control.

If I don't drown first, this is gonna be the hottest thing that's ever happened to me, Jacob thought, undeterred by the mess of his own juices as they swirled around him with the rest of her plentiful moisture. I just hope she still feels the same way tomorrow when the booze wears off...

Shannon wasn't tipsy in the least...but she was drunk on lust and terribly eager for a refill.