Office Holiday Party Ch. 02

Six months had passed, and Phoebe had transferred to another office on the other coast. It was a beautiful Monday morning in June, sunny and warm but not oppressively hot. Brittany stepped out of the elevator in her olive green sundress and sandal wedge heels, a light layer of sweat from her morning commute helping the dress cling to her every curve. The tall, captivating brunette had turned more than a few heads on her walk to the office. When she opened up her email at her desk, there was one new unread message highlighted in blue.

Ugh, a meeting request for 9:30 AM on a Monday.

A look of disgust appeared on her face, but it was quickly replaced by a familiar tingle in her nether regions when she noticed that it was from Jill. She anxiously bit her pen cap as she accepted the meeting request. A half hour later, Brittany's calendar reminder popped up, and she made her way to Jill's office. Standing in the doorway, Brittany knocked on the open door.

Jill had her medium-length blonde hair down today and was dressed in her usual look, a tight blouse and pencil skirt. Today, her blouse was a light blue, and her pencil skirt was a light cream color. Jill looked up from her computer to give the brunette a sweet smile. "Come have a seat. Close the door behind you."

Brittany complied. Jill looked at her slut seated across from her. "Well, did you both have a good weekend?"

"Yes, Mistress."

"Good," Jill smiled again. "Now as you know, since everyone at the company has been working so hard, we have a special picnic outing on Friday afternoon. I also have a gift for you to show my appreciation for how well you've been doing, my little slut."

Jill opened her drawer, pulling out a small white box and sliding it across her desk. Upon opening it, Brittany revealed a pair of black panties.

"Well? What do you think?"

"Um...thank you Mistress," Brittany said.

"You're very welcome," Jill beamed. "Go ahead. Try them on."

"N-now?" Brittany asked.

Jill's voice again hardened. "Are you questioning me?"

"N-no, Mistress," Brittany quickly responded.

She stood and reached under her green dress, sliding down the white thong she was wearing. Her face reddened slightly when she noticed that they were already quite damp from a combination of sweat and her juices. Brittany put on her new panties and pulled her dress back down, standing at attention in front of Jill's desk.

"Good," Jill said, holding out her hand.

Brittany placed her thong onto the center of Jill's open palm, which was quickly deposited into the bottom desk drawer. Jill then pulled out a small pink remote and clicked it on.

Immediately, Brittany's legs buckled as her panties began rumbling against her pussy. She caught herself on the desk with both hands, squeezing her legs together as the vibrations sent tingles throughout her body. The fresh pair of panties were immediately wet from a flood of juices leaking out from her excited slit.

"Does that feel good?"

"Y-yes," Brittany said breathily.

"Alright, off you go then. I want to see you back here at noon to discuss something important."

"Um..." Brittany's legs continued trembling from the sensation of the panties vibrating against her clit.

"Is there a problem?" Jill asked.

"No, Mistress."

"Then see you at noon," she said with finality.

The young marketing associate began shakily walking to the door. But when she reached it, the vibrations from her underwear suddenly ceased.

"Oh, alright," Jill sighed. She didn't want to arouse suspicion from any coworkers if Brittany stumbled or fell on her walk back to the desk. "Hurry back to your desk."

A wave of relief washed over her, and she went to her desk. She took a sip from her water bottle and began looking over an invoice in her inbox.

Brittany gasped lightly as her panties reactivated, sending fresh shocks of pleasure coursing through her pussy. She pressed her legs together tightly and tried to focus on the invoice on her screen, but the letters and numbers might as well have been hieroglyphs. They were completely incomprehensible in her current state, her eyelids fluttering from arousal.

A low, barely-audible moan escaped from her lips, which she quickly disguised as a cough. She pulled one hand to her mouth, biting down on her finger to avoid making further noises. Brittany glanced over at the girl whose desk was opposite hers, but luckily she had her headphones in and had noticed nothing. But at this rate, the sensations would too much to handle. She could feel an orgasm building up, and try as she might, she didn't know if she'd be able to stop herself.

Brittany knew that Jill would be furious if she came, not having been granted permission to do so. But all the same, her cunt was quivering from delight, and she didn't know how much longer she could hold it off. Just when she was on the edge of cumming though, the vibrations stopped abruptly. She leaned back in her chair and tried her best to control her heavy breathing in an attempt to regain her composure.

In her office, Jill smirked as she clicked the remote to the "off" setting. Observing her obedient slut through the video feed on her computer monitor, she was pleased at how hard Brittany had worked to stop herself from orgasming. The two high-definition spy cameras she'd installed in the overhead lamp above Brittany's cubicle and hidden under her desk had been very expensive but worth every penny. Jill's fingers absentmindedly rubbed her mound through her panties as she watched Brittany try and get back to her work.

A knock at her door jarred her back to her senses. Her meeting reminder was blinking on her other screen, but she'd been too focused on watching her slut through the hidden cams to notice. Jill hastily minimized the video feed and put away the remote. Adjusting her blouse, Jill did her best to hide her stiff nipples, whose outlines could be barely seen poking up under her shirt, even through her bra.

"Come in!"

A tall young man with a slim build walked in.

"Hi Jill."

"Hey Ben," Jill flashed him a brilliant smile. "Come on in. Close the door behind you."

Once he'd sat down, he scratched his beard, if you could even call it that. It was more like a line of patchy hair barely filled in enough to dot his chin. In fact, Ben looked barely out of high school, much less college. He'd helped Jill recover an accidentally deleted file a few months ago, and she'd noticed him admiring her cleavage when he thought she hadn't been looking. Being the enterprising woman she was, Jill had filed this away for when she might need something else from this tech support guy, and that day had come.

"What can I do for you?" he asked.

"Well, first I wanted to thank you again so much for helping me get that file back." Jill leaned forward as she spoke so that Ben could get a better glimpse down her blouse. "I don't know what I would've done without you."

"Oh, no problem at all." Ben grinned sheepishly.

"Since you were so helpful before, I was wondering if you might be able to help me with something else."

"Sure, what do you need?"

Jill smiled as sweetly as she could. "Well, remember Christina, that new intern whose computer you helped me set up a couple of weeks ago?"

How could I forget? Ben thought to himself, recalling the cute blonde from when he'd dropped off the laptop.

"Y-yeah? I think so."

"Well she's off today, but I need a file that she has saved on her desktop. Can you help me log into her computer?"

"Um...well I don't think we're allowed to give out another employee's login and password information, but I might be able to find the file for you."

Jill frowned. She'd expected Ben to just roll over and acquiesce to her request, but she could see that she might need to work harder to get what she wanted.

"Well, she is my direct report. I'd also like to see if her work is good enough to make it worth hiring her on full time, or if she's slacking, stuff like that. You know?" She smiled again at Ben.

He returned only a puzzled grimace. "Er...well technically I could, but I really don't think we're supposed to do that. I could get into trouble or even fired for giving you access."

Jill drummed her fingers on her desk in annoyance. She weighed in her mind whether adding Christina to her collection of sluts would be worth it. After a moment, her fingers paused as she had made up her mind. She stood from her plush office chair and walked around her desk. Ben craned his neck and watched as Jill approached where he was sitting.

"I have a proposal for you," Jill bent over and gripped the arms of the chair of Ben's chair, leaning down until her face was mere inches from Ben's. Her blouse loosened as she bent down, granting him a wide-open full view of her ample cleavage underneath.

He gulped.

She reached down with one hand and rubbed his crotch over his pants, feeling his cock stiffening underneath. "I'd be willing to...show my appreciation if you could get me her login info."

Ben groaned with lust as she groped his member through his pants.

"Do we have a deal?"

Ben considered his situation. It had been a while since he'd last been with a girl, and even though there was likely a ten-year age gap between them, Jill was still smoking hot. Plus, it wasn't exactly like Jill was asking him to log into the CEO's computer. She just needed to take a look at an intern's computer.

Fuck it. He thought. When else was he going to get an opportunity like this? He gulped again and nodded.

Jill smiled at Ben's indication to proceed and slid down to her knees. Spreading his legs apart, she unzipped his pants and pulled out his rapidly hardening dick. He could feel her hot breath as her mouth hovered over his cock, and her hair gently brushed over his crotch. It had been a while since Jill had given a blowjob, having been preoccupied these last few months with her new toys, Phoebe and Brittany. However, she was a seasoned veteran with plenty of expertise. There had been plenty of reasons her marriage had ended, but bad blowjobs most definitely had not been one of them.

"Unghhh," Ben groaned with pleasure as Jill took him into her mouth. Her warm lips wrapped around the head of his dick, and her tongue swirled around his tip, licking up the precum that had exuded. Jill's head bobbed up and down the top half of his exposed cock, coating it in her saliva.

After a few more bobs, she gripped his dick and removed her lips for a moment. Pursing her lips, she gathered a big mouthful of spit and let it slide down her tongue. Her saliva dripped down onto Ben's meat, and Jill used her fingers to spread it up and down his shaft. Once sufficiently covered in her spit, she reinserted his cock back into her mouth.

"Fuck," Ben groaned as his dick slid further into her warm, wet mouth, inch by inch.

As Jill continued to slide his cock down her throat, she was surprised by how big he was. It always seemed to be the tall, skinny guys who had the biggest dicks. Though it had been some time since she'd deep-throated anyone, she quickly reacclimated and soon reached the base of his cock with her lips.

Ben shuddered as he felt his tip hit the back of her throat, the entire length of his shaft now engulfed by her mouth. Jill began blowing him in earnest, sliding his long member in and out of her throat. Even though Ben was a means to an end, she could feel the moisture leaking out of her slit. But even with her pussy aching with desire, she remembered her priorities. With a pop, she slid his shaft all the way out of her mouth and leaned back.

"W-wait," Ben stammered. "Why are you stopping?"

"It feels like I'm doing all the work here, Ben. Login info first, then you get to finish." Jill purred and walked back around the desk and sat in her chair.

He quickly flipped open his laptop and began typing furiously, his dick still at full mast. While Ben worked on getting her what she wanted, Jill opened up her video feed in the meantime. She discreetly took out the little pink remote and flipped the switch to the highest setting.

At her desk, Brittany was typing up a reply to an email when the panties came to life. Her hand scraped across the keyboard as her body jerked in response, and her left leg slid open and banged into her cubicle wall. She gripped the edge of her desk with both hands and shut her eyes as the vibrations attacked her pussy, sending tremors throughout her body.

Her cunt was so wet by now that she could feel her juices dripping down her taint, staining the back of her dress and her seat. Brittany sat as rigidly as she could, inaudible whimpers coming out of her mouth in short bursts as the vibrating panties took their toll on her. She could feel her clit pulsing with pleasure.

Back in Jill's office, Ben's penis had drooped to a half-chub as he worked. It had been less than ten but it had felt like hours.

"Alright, got it!" he finally proclaimed triumphantly.

Jill shut off the panties, closed her video feed, and put the remote back in her desk drawer.

At her desk, Brittany collapsed onto her elbows in both relief and frustration, relief as she'd been on the edge of orgasm, which she would've been punished for, and frustration because she desperately need to cum after coming so close twice now in one morning.

In her office, Jill grabbed her pad of post-its and handed it to Ben. He quickly scribbled down the login and password and gave it back to Jill. She inspected what he'd scrawled on the little square of paper and asked, "You're sure this will work?"

Ben nodded. "You can log in on her laptop or remotely from our intranet site."

She beamed at him. "Perfect. Why don't you put away your laptop then? Time for your reward."

He didn't need to be asked twice and instantly slammed closed the screen and put it down on her desk. By the time Jill had gotten up and walked over, Ben was already rock-hard.

"Oh my," she exclaimed as she grabbed his cock and played with it. "Looks like you're already prepped for me."

"Oh yeah," he grinned.

She let go of his dick and pulled up her beige skirt, revealing her black lace thong. Jill pulled the damp material to one side, exposing her pussy lips, already slick and glistening with her nectar. She straddled Ben and lowered herself onto him.

"Oh fuuuck."

Ben threw his head back in ecstasy as he felt the inside of her warm cunt slide down over his cock. Once she'd taken his entire length inside of her, Jill started bouncing up and down, slamming his length up into herself over and over.

"FUCK!" Ben choked out as she rode him mercilessly.

It was a good thing that her office, along with all the offices on this floor, was completely sound-proofed due to the sensitive nature of some of their phone calls. In fact, Jill had come in on a weekend months ago and tested it just in case, blasting porn from her computer and closing the door from the outside to see if she could hear anything. She and Brittany had also had some "working lunches" in her office over the last few months, and they definitely would've both been fired had anyone heard some of the screams and moans that had ensued.

The veins in Ben's neck bulged as she slammed her ass up and down on his crotch. He could smell the perfume emanating from her chest, her large breasts bouncing about with every stroke. Her blouse had come untucked at the bottom, and every time she buried him deep inside of her, he struggled not to cum too quickly. But it was a losing battle, and he could feel his balls ready to explode.

"Fuck, I'm gonna -- UNGH -- I'm gonna cum," he managed to get out in between bounces.

"Go ahead baby," Jill leaned in and whispered into his ear. "Cum deep inside me. Fill me up."

"Oh shit!"

Just like her ex-husband, that was all it took to push Ben over the edge. Right on cue, he grabbed her ass cheeks with a vice grip and grunted like a madman as he convulsed, shooting his load deep inside of her.

Jill could feel his balls pulse against her ass, releasing his a torrent of his seed. While she had experienced plenty of strong orgasms from Brittany's tongue and other toys over the last few months, nothing quite replicated the feeling of hot sperm filling up her cunt. She slowly stood, sliding his softening shaft out of her. Finally, she stood all the way up, and his now limp dick fell to one side, leaking a bit of cum onto his pants.

She quickly pulled her panties back over to cover her pussy, deciding on an impulse to save Ben's cum as a little surprise treat for Brittany. Jill sat down behind her desk and tucked in her blouse as Ben put away his dick and zipped up his pants.

"Let's keep this our little secret," Jill said slyly. "If you're lucky, maybe I'll need another favor from you soon."

Ben grinned. "You got it."

Once he'd collected his laptop and left, Jill decided that she couldn't wait until lunchtime. She opened up their office's messaging app and typed to Brittany, "come to my office."

When the message appeared on Brittany's screen, she locked her computer. Despite her need to cum, she was very aware of the fact that the back of her dress was still soaked in her wetness. She stood up and looked around for a moment. Seeing no one in the hallway, she grabbed a stack of papers and held them behind her as she briskly walked to Jill's office, shutting the door behind her.

"Hello, slut. My, you got here quickly."

"Yes, Mistress."

Jill pointed down at Brittany's feet, and the girl quickly obliged. She set down her stack of papers next to the door and got down onto her hands and knees. Brittany slowly crawled on all fours until she reached where Jill was sitting behind her desk.

"Are you hungry, slut?"

"Yes, Mistress." Brittany replied eagerly.

"Go ahead then."

Jill propped herself an inch off her seat, allowing Brittany access to remove her panties from under her skirt. She then hiked it up, revealing her wet cunt and thin landing strip. Jill patted her mound, and Brittany leaned forward and began licking up the juices.

"Mmm, that's a good girl." Jill encouraged. With one hand, she reached down and grabbed the underwear remote out of her desk drawer and flipped it to the highest setting.

"Oooh," Jill moaned as the activation of the panties cause Brittany to moan and start slurping the older woman's slit with intensity. She could feel Brittany's tongue writhing around her pussy lips. Meanwhile, Brittany felt that Jill tasted different today but wasn't sure why.

Jill grabbed the back of Brittany's head and pushed her against her mound. Her slut's tongue was now flicking over her clit, and it felt marvelous. A combination of her pussy juices and Ben's now watery cum leaked out and coated Brittany's lips and face as she continued eating out her mistress.

As she did so, Brittany felt her own pussy rippling with pleasure, the constant drone of the vibrating panties driving her to orgasm. She could feel it building within her, her cunt beginning to contract as the waves of delight kept washing over her.

"Mistress." Brittany tried to speak, but Jill's grip on her head meant it came out as a muffled "Mmmph mmm" sound against Jill's cunt.

Brittany tried again, this time pulling her head back. "Mistress," she cried out. "I'm gonna cum."

"NO!" Jill commanded.

Brittany strained but stopped herself from going over the edge. Jill grabbed the remote and turned it down to the lowest setting, and the other girl relaxed a bit.

"Continue," Jill ordered. "You can cum after I do."

Brittany dove back into Jill's crotch and renewed her efforts, licking and sucking at Jill's clit with vigor.

"Ohhh yeah," Jill moaned loudly.

Her slave's tongue felt so good, having been trained expertly over the last six months. She grabbed and fondled her own breasts as she felt her orgasm building. Brittany continued attacking her clit, licking rhythmically, her head buried between Jill's shapely legs. Jill's clit throbbed at the assault it was receiving, and the thought of Ben's cum still deep inside her while her slut ate her out drove her over the edge.