Coworkers With Benefits

This story was originally written for the

On The Job Challenge 2025

in April 2025.

=========

Alyssa fished from her purse a nondescript plastic badge. She swiped it against the black scanner by the door, feeling that little twinge of irrational tension before the light on it turned green. The door unlocked and she pushed it away to walk inside, just like she had done every day for the past several weeks.

This was her office, after all, even if the work she did there was unorthodox to say the least.

"Six bookings today," she said, a trace of smile curling her rouge lips. "Should be alright, I guess..."

She was standing over her desk, looking at the computer screen that showed a spreadsheet of today's appointments. It wasn't packed very tightly; certainly nothing she hadn't handled before. She could deal with all these customers without issue, she thought, especially given how considerate they had been so far.

Though Alyssa had been doing this for some time, she still felt like she was very new to this line of work. She told herself that this was perfectly normal. For one, it was a totally different job than the one she'd been aiming for when she showed up for the interview. This alternative offer really came out of the left field, and the young woman was understandably quite shocked when she heard what it entailed.

As she took off her overcoat and hanged it on the rack, her mind went back a few months and replayed the memories of that bizarre interview.

"I'm rather impressed," she remembered the older businesswoman say. "You definitely know your way around the web frontend and all those modern frameworks, including the one our engineers are using. It also seems like you've got a decent amount of knowledge and experience with privacy and security issues. Overall, pretty darn good..." She looked to the side. "So, what do you think, Jesse? Would Alyssa here be a worthwhile addition to the team?"

Jesse had introduced himself as the CEO, and tech was probably the only industry where he could actually look like one. The guy didn't even break into his thirties; a button-down checkered shirt was still the height of his fashion sense, and the bloodshot eyes plus a frizzy mane of brown hair on his head gave off an appearance of someone who'd just spent all night either partying or coding.

He was flanked on the left by a much more elegant woman, somewhere in her late thirties to early forties. A maroon tweed jacket was slung over her slim figure, touched by the strands of wavy, blond, shoulder-length hair. She was sitting across the table. looking at Alyssa with a polite but perfunctory smile. The corners of her lips dug deeper and deeper creases into her cheeks, which were already more wrinkly than you'd expect given her relatively young age.

"I don't know, Heather," said Jesse. "Frontend is one thing, but so far the whole team has been very much on the full-stack side. I'm not confident we can specialize just yet, in terms of distinct skillsets of our engineers. Yes, I know that Alyssa has worked closely with the backend guys at her current company but that's not same as, say, tweaking a deployment pipeline, running a complex database migration, or diagnosing issues with our cloud provider's API."

"Isn't it something she could learn on the job pretty quickly?"

He looked at Alyssa and flashed her an apologetic smile. "I'm sure that she could," he said, turning back to Heather, "but if we want to get out of the closed beta ASAP, then there is very little leeway we have when it comes to additional overhead such as onboarding new engineers. I mean, I really don't want Rick to have to pick up the sl--"

"The investors won't be happy, Jesse," she interrupted him, her voice gaining an audibly shrill edge. "You should know how important diversity is, especially these days... You've got an all-male team right now, and here's a great female candidate that is eminently qualified, even if not perfectly in the way you'd like her to be. Are you sure there is no way to, you know -- fit her in?"

Alyssa had to stifle a gasp. She was surprised they'd discuss such things openly, with her sitting right there. She always suspected that being a woman in this industry was giving her a slight advantage over her male peers, but never before had it been spelled out so explicitly. There was a not-so-small part of her youthful idealism that died right there, the illusion of pure meritocracy dissipating in a puff of ugly gray smoke.

"Sorry, Heather, can't do," the young CEO said with surprisingly firm conviction. "Getting to market is the most important thing for me right now. Quite frankly, it should be for you and your VCs as well, assuming you're still looking forward to the expected returns on your admittedly very generous investment..."

And yet, this somberly illuminating exchange was nothing compared to where the conversation had gone next.

"Fair enough," said the older woman. "Miss Brewster --"

"That's okay," Alyssa said. "I understand. I wouldn't want to be a drag on the team's productivity."

She was just about ready to get up and leave. This interview wasn't a crucial lifeline, because she had a decently paying job at a much larger corporation. What she had been looking for was career advancement in a more exciting environment, however cliche that may sound. Now, though, she was mostly just waiting for Jesse and Heather to officially say no, and then follow it with a quick and polite goodbye.

But instead, Alyssa had heard something rather different.

"Well, I'm glad that you understand," Heather said, her eyes giving a little twitch as a quiet sigh escaped her thin lips. "Let's just leave it at that then. However, now that the question of an engineering role is firmly out of the picture... Jesse? What do you think? Would you say Alyssa might be suitable for that

other

role we've been talking about? You know, the one we're not advertising publicly..."

The man's face rapidly lost some of its beige color in favor of a pale shade of pink.

"Heather, are-are you sure about this...?"

"Of course. Didn't you just say we need every leverage we can find, so that we can get to market as quickly as possible? I agree wholeheartedly."

He was visibly flustered now. "Okay, well, if that's the case," he began, audibly taking a deep and nervous breath, "I'd say that she looks, ahem...

very

promising."

Alyssa's brow furrowed. "Excuse me but -- what is this about, really?"

The older woman smiled at her. "Miss Brewster, I believe that we might have an even more attractive offer for you," she spoke in a curiously smooth voice. "In terms of compensation, for example, this alternative position would far exceed the salary brackets we have posted for the original engineering role. It would be the upper bound, in fact, except

doubled."

Alyssa couldn't hold the loud gasp that managed to escape her throat. "I... I'm listening..."

"Excellent. And I must say I appreciate what you said earlier, too, about not wanting to be a drag on Jesse's team productivity, because in this role, you would become essentially the exact opposite."

She blinked in confusion. "Huh?"

Heather's wrinkly smile grew even wider. "Well, let me explain then..."

And boy, explain she did.

Thinking back to it now, as Alyssa looked at her reflection in the floor-to-ceiling mirror in her office, she could totally understand why Jesse said she was a very promising candidate. Her qualifications were obvious and plain to everyone around, precisely because she was anything

but

plain.

The perky young woman was strikingly beautiful -- which, next to open-mindedness and a friendly personality, was one of the key requirements for success in her new role.

She stood at average height and had a slim but full figure. The curves of her wide hips and heavy breasts narrowed down to an impressively cinched waist.

Her face was exceedingly pleasant, corralled by falling locks of auburn hair that would playfully brush against her high cheeks. They complemented her deep amber eyes that sat above a cute button nose, and a puffy oval of her lips that she liked to touch with just a smidge of red lip gloss.

"Hmm... I wonder if I should change?" she mused, looking at her outfit of thin woolen sweater and blue denim pants. "But Connor's first today, and he usually doesn't ask for much, so..."

Officially, Alyssa's title was that of an Employee Satisfaction Specialist. Whenever she heard it, she found it hard not to burst into a fit of sardonic laughter. It matched her role perfectly, if only in a perverse manner, because

satisfaction

was precisely what the girl's job was about.

Heather had explained it to her back then, in a very no-nonsense kind of way.

In many tech startups that the woman's venture fund invested in, she had noticed all the same problems with demographic makeup of early employees. You didn't have to subscribe to fashionable opinions on diversity to see it, and Heather's concerns about the issue stemmed from rather more practical motives than the desire to appear righteous on professional social media.

Simply speaking, those fledgling companies were almost always full of young single men. Overworked and under-socialized, these men had neither the time nor -- let's be honest --

ability

to attract women and form any kind of satisfying relationship. Nature being what it was, however, these guys still had very real physical needs. Failing to meet them would inevitably lead to detrimental effects on their well-being and, in turn, their morale and productivity at work.

Enter Alyssa. Her job duties, how that she had accepted the offer, revolved precisely around satisfying those unmet needs.

She was given a dedicated office that had been furnished with all the necessary amenities. It included a comfortable bathroom with a spacious shower cabin; large wardrobe and several closets where she could keep clothes and personal items; a king-size bed along with a dozen sets of sheets and linen; as well as a bean bag, an exercise ball, two chairs, a mirror, and an agave plant in a clay pot. It was all very pleasant and cozy.

She also had a desk with a computer that she'd use manage her appointments. They were done through a system similar to what her previous company used for onsite massage bookings. Other employees were free to schedule individual sessions with Alyssa, up to a certain limit per week, for either half an hour or a full hour.

Just like a massage therapist, the service she'd provide during her sessions was physical and tactile in nature. Difference was, hers was also of a much more

intimate

kind.

"Ahh, yes," Connor said with a breathy sigh. He was a thin, bespectacled man in a creased T-shirt, not exactly a heartthrob but not particularly unappealing either. "This feels... really great..."

Alyssa would've liked to respond, but her mouth was currently quite full. She was kneeling on a folded yoga mat on the floor, leaning into the chair where Connor was sitting and diving between his parted legs. With his cargo pants and boxers pulled down to his ankles, his hard cock was out and pushing into the girl's straining throat.

He was surprisingly big for a guy his height. Despite plenty of opportunities to practice over the last few weeks, Alyssa still had problems getting him fully inside her mouth. She needed to reach with outstretched lips to hit the mark at the base of his cock, at the same time moving the neatly trimmed pubic hair to stimulate the sensitive skin underneath. Getting her tongue there was unfortunately out of question. It had already happened this session that she had to fight her gag reflex; the cautious girl would rather not risk it again.

But this was okay. She was still learning the chops. It wasn't like Connor had any complaints about the quality of service he was receiving.

"I'm not gonna last... much longer..."

She gave him a thumbs-up and lowered her hand back to his ballsack. She tried to remember not to neglect it, but doing so many things at once required a surprising amount of concentration. Lips, tongue, throat, teeth (gently!), fingers, sometimes even nose and chin...

Sure, she had given blowjobs before; her last boyfriend even said she was the best he'd ever had. But doing it as part of her work duties added an extra layer of pressure she couldn't help not to feel.

No matter the endeavor, Alyssa wanted to excel in it.

"Here... here it goes, Lys!"

Conner's pressure, on the other hand, was already being relieved in a very explosive manner. His cock twitched and pulsed, erupting thick ropes of semen inside the girl's sucking and licking mouth. The amount didn't faze her, for the man had his balls drained regularly, but she wasn't a huge fan of his flavor. One of these days she'd tell him to pick fruits over chips whenever he went to the snack station.

"Wow... I don't know if I should say this but, uh, I feel like you are getting better every time."

She chuckled into his softening cock. "Thanks," she said, as she released the organ from her mouth and wiped it clean with a tissue she always kept nearby. "I

am

trying my best, you know? And not just when I'm on my knees, or there," she added, thumb pointing at the bed behind her.

"Right. And I really appreciate it," Connor said, pulling up his underpants. "We all do. I don't know if anyone told you this, but Jesse gave us a very stern speech before your first day, warning us not to make, well, this"--he broadly gestured around the room--"more awkward than it needs to be. And sure, it was a bit weird for the first week or two, but it seems like it just naturally stopped being a big deal. I wonder whether you feel the same way, if you don't mind my asking..."

Alyssa rose from her knees and sat opposite to him on the bed.

"It's... Well, if I am to be honest..."

"Please."

She bit her lip. "I'm kinda starting to like it."

"Really?"

The chuckle she gave was only a little bit nervous. "Yeah. I don't know if you've noticed but I'm pretty easy-going overall, and it's not like I was an innocent little angel before this!"

He laughed then. "College days, eh?"

"Nope, not telling!" she teased. "Trade secrets."

He laughed again. "Alright, I won't pry."

Connor stood up and buckled his pants, rising above Alyssa whose head would only come up to his shoulders. He gave her a look, as if trying to remember something he forgot, before flashing an awkward smile and turning around to leave.

"We still got ten minutes, by the way," she said.

"I know, but that's okay. I should get back to work anyw--"

"It looked to me like you wanted something."

He turned again, his face gaining a slightly rosy hue. "Ugh, no, I just... Nah, never mind. It was silly and inappropriate."

She burst out laughing.

"Inappropriate?

You mean, more than coming a big load straight into my mouth?"

He blinked, and moments later he let out a hearty chuckle. "Okay, you've got a point. I was just wondering what kind of, uh, lingerie you're wearing..."

She resisted the urge to roll her eyes. At the same time, it didn't escape her notice how she would've probably taken offense at such a question just a few short weeks ago.

"How about next time," she said, as she stood up and began taking off her clothes, "I'll just strip before getting on my knees...?"

Only a few moments later Alyssa was down to just her sexy underwear. It was a crimson set of erotic lingerie, with lacy shelf bra which scarcely covered her nipples and a pair of skimpy silk panties that exposed a lot of flesh of her firm and shapely butt. Smirking, she did a little twirl to give Connor a good look from every angle, making the man's jaw drop as he beheld her gorgeously feminine form.

"Well...?" she asked coquettishly.

"Damn!"

She chuckled. "Glad you liked it. Just remember that if you need my help again because of this, that's probably going to be another appointment!"

"Oh no!" he joked. "Guess I better run then!"

He gave her one more meaningful glance, pausing for more than a few seconds when she leaned forward with her hands cupping the large mounds of her breasts. She sent him a wink and he responded with a cheeky grin, before waving his hand and saying he would be back tomorrow.

Once the door close, Alyssa sat back on the bed and sighed. She thought that was a bit unexpected. While the blowjob didn't do much, not for her, getting shamelessly ogled by Connor had resulted in a small, wet patch that darkened her red panties. She felt a little flush, but not enough to do something about it all by herself, and certainly not in only ten minutes.

She tiptoed to her desk to check whose appointment was next.

"Blake," she gasped, but then her lips rose in a sultry smirk. "A full hour, as usual... Welp, time to get the daily dose of stretching!"

***

When she told Connor she was starting to like her job, Alyssa hadn't been entirely truthful. In reality, after little over a month of working in her new role, there were very few things she

didn't

like about this whole arrangement already.

A lot of it had to do with the sort of people that had joined this fresh new startup. There were only six engineers in total, and not much else in terms of other types of staff. Both the product manager and the UX designer were married, so neither had paid her a single visit. Jesse, the CEO, had basically poured his life into this company, meaning he neither had the time nor was ever in the right headspace to seek relief from the

specialist

that he hired.

As a result, Alyssa was pretty much stuck with the nerds.

Some of them fit the stereotype to a T, much to her chagrin. Two guys in particular needed improvement in terms of hygiene standards and grooming. Thankfully those were the only two instances that prompted the girl to refuse service, which she had the contractual right to do, and raise the issue with Jesse. She couldn't even begin to imagine in what manner he must've berated them afterwards, because next session they both showed up impeccably clean and freshly manscaped.

Men like Connor and his younger colleague Brian never posed any such problems. If she were to make a choice, she'd probably say that those two were her favorites. They were unproblematic, polite, and typically very easy to please. Whenever either of them came for more than just a simple blowjob, he'd make sure Alyssa had as good a time as he did.

It was the last two guys that presented the biggest challenge for the hard-working girl. And in one case, said challenge was big in a very literal sense.

"Ooooh!... Fuck, alright, here we go again..."

Hands and knees on the bed, the sweat-slicked redhead tried to muster another ounce of courage and willpower. She needed everything she got, and likely more, to push back against this unbearably thick invader. Gritting her teeth she let out a mighty groan, as she felt another inch of what had to be a sequoia stump force itself inside her overly tight pussy.

"Everything alright in there?" a voice behind her asked in a low baritone. "I'll take a blowie if you can't --"

"No, no, it's... it's fine," she hushed him. "Just need... a minute... Ooooh!"

"Okie."

Alyssa certainly wasn't a quitter. If there was anything the upbeat girl truly hated, it was disappointing people that he liked or giving up when the challenge was clearly surmountable. Not taking Blake's cock in her pussy would count as a failure on both accounts, and so the naked young woman was really applying herself to the task ahead.

Or, more precisely,

behind.

"Ugh... Tell me it's almost in?"