Multitasking

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An executive assistant does whatever she can to help.
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"I promise, my guy, she'll change your life. She'll take care of everything you need, and you'll actually be able to concentrate on the stuff that matters. But I'll be honest, she's not great at multitasking."

I felt a pang of guilt in my chest. Sara really was a qualified candidate for the job but Ben was leaning into his sales pitch hard, probably harder than was necessary. I hated the process of interviewing and more than that, I hated having to make that call after to let them know that "we totally loved your interview and your energy, but we're looking for a candidate with more of a background in office administration". Especially when what I really wanted to say was "Your interview was weird. You showed up eighteen minutes late to the interview, covered in croissant crumbs, and asked how many vacation days you'd get in the first month."

But in this case, Sara truly had the background we were looking for, was great at client-facing communications and had successfully managed a family of five without killing anyone as a stay-at-home mom for the last nine years. So, with her twins finally in kindergarten, at 36, Sara was ready to re-enter the workforce. It also helped that it meant I wouldn't have to make the "thank you for your time, we'll keep you in mind for the future" call to someone who had regularly seen me Saturday shitfaced in green and orange.

Ben and Sara had been some of the first friends I made when I arrived in Charleston four years ago, and they didn't hold my choice of college football fandom against me. As a recent college graduate new to the city and without knowing a soul, they took me in like a stray and kept me coming back with a seemingly endless supply of wings, beer and ACC football. When that first football season ended, our regular Saturdays turned into afternoons out on the boat or out at the sandbar. On more than one occasion, Sara had to steer me--more than a little drunk--into the back row of their family vehicle and tucked me into bed in their guest room, even supplying a glass of water on the nightstand to stave off the impending hangover.

Hiring Sara at Parker Whithouse was probably the least I could do to return that favor, all things considered.

Technically, Sara's title was "Client Administration Liason", but in practice, she was the perfect pinch hitter. Her job description ended with the phrase "and will complete other duties as assigned," and that summed up about all of it. She scheduled check-in meetings between clients and partners, kept track of the jumble of shifting deadlines and even assisted in brainstorming sessions before pitch meetings. More than once, Sara had shown herself an adept graphic designer, sketching storyboards and logos on takeout napkins when one of the partners struggled to define his vision. She didn't belong to any one particular person in the office, but I couldn't deny that I found myself a bit territorial, and always made it a priority to seek out Sara when I had a project I needed an extra pair of hands on.

It was one of these such projects I found myself dealing with in the Spring of 2021. One of our long-standing clients, a construction materials firm, had asked us to facilitate a full overhaul of their branding, online presence and customer interface, with a deadline to roll-out the new designs in time for their annual trade show expo. The process had been mostly painless, until three weeks before rollout, when their senior VP of marketing was caught with his pants down at work, literally. The ensuing domino effect resulted in a shake-up of their leadership and a sudden new vision for the rebrand. So, instead of putting the finishing touches on the project, we were now back to the planning stages with a new VP who seemed to relish her ability to make our lives as inconvenient as possible.

"I just think it needs to be sleeker, sexier, you know, Jackson? We're not trying to be boring and frumpy, we want to excite people. So, let's figure out how to get it sexier, and then send me the next draft by the end of the day tomorrow."

I gave a cursory agreement and closed the Zoom meeting. I'd have had a whole lot more patience for her desire to make things "sexier" if she hadn't moved the goalposts with such irregularity. As it was, I barely had time to make my own life sexier. The pressure of the project had grown to the point that I didn't have much energy for going out on dates, especially not to the kinds of hipster wine bars that were the current obsession of every single woman I met on Tinder.

Sheepishly, Sara cracked the door to my office and peered in, her auburn hair cascading like a curtain around her.

"God, that was brutal. I'm not sure that woman would know what sexy was if it gave her a lap dance and bit her earlobe. You held your composure pretty well, for what it's worth."

I struggled against the sudden desire to imagine Sara giving that exact lap dance and lob bite combo. God, it had definitely been too long since I'd gotten laid.

Sara shut the door, and flopped down in the leather chair across from my desk. She crossed her ankles and threw her legs up over the side of the wooden armrest. Sara had a habit of treating any piece of furniture as a couch, a trait she once referred to as the "bisexual urge to sit weird". I put my elbows on the desk and pressed the heels of my palms against my eyes. I exhaled the tension I hadn't realized I was holding in.

"Their logo is literally a hammer and a nail, and they refuse to change it. I'm about to just slap the slogan 'We'll get you nailed' on it and send it back to her. The pressure is getting to me, I'm not even sure I know what is sexy anymore. It's been too long."

Sara ran her fingers through her hair and chuckled.

"What about Cassie? Didn't you guys go out for drinks last week? Her texts seemed like she was planning to have a lot of fun!"

"So, apparently many women do not appreciate when you cancel on them at the last minute. Or forget to respond to their texts for 48 hours. Especially Cassie."

Sara shook her head and rolled her eyes.

"Ok, seriously Jackson, how long has it been?"

"Since I had sex? Or since I've had anything at all?"

"I guess it doesn't really matter, since I'm going to be sad for your answer regardless."

"Let's see, my date with Olivia from the coffee shop ended with a blowjob, before she started crying about how much she missed her ex. So, what was that, a month ago?"

Sara stuck out her bottom lip exaggeratedly then laughed again.

"Poor Jackson. No wonder you can't make a sexy logo. You're all backed up."

"You have no idea." The words escaped my mouth, and I immediately tried to catch them, like a child who accidentally tells on themselves.

Sarah bit down on the inside of her lip, and walked back to the door. I had crossed a line, and the friendly banter had died. I muttered an apology but was interrupted partway through the second "Sorry" by the click of the lock and the latching of the chain on the old wooden office door. Parker Whithouse had recently, in an attempt to capture the creative aesthetic, had relocated their offices into a turn of the century building in the old downtown district that was definitely not massively gentrified.

"It's my job to help, right?"

There was a mischievous curl to her lips, and a villainous glint in her emerald eyes.

"Sara, I..." I stumbled through my words, trying to pull the mental brakes on the moment.

"Don't make a whole thing about it, you need help to clear your head, and I'm good at clearing it."

"Ben would kill me, I can't, you can't, we can't."

She stopped and cocked her head at me, raising her eyebrows.

"One--who's telling him? Not me. And two--don't pretend like you aren't well aware of what happens on his 'sales retreats'. He once came home with a receipt for Plan B in his pocket. So at least I know he's not paying for a secret side family too."

I looked at Sara again, this time letting myself feel that hunger I had shut down earlier.

"I really do need the help."

Sara reached behind her, and gathered the waterfall of red hair into a messy bun, and secured it with one of the hair ties she always kept at the ready on her wrist. As she walked across the office towards my desk, I took in the power of her. Years of chasing kids, building playsets and carrying diaper bags and laundry baskets had toned her arms and the weekends of soccer practices and playdates had darkened the constellation of freckles that splashed across her skin. Her wrists jingled with the gold bangles that adorned her arms and she made a shushing gesture as she slipped them off into a pile on the cabinet underneath my window.

With a twirl, she spun herself around as she pulled my chair out from behind my desk, carrying me away with it.

"Like I said, she wouldn't know sexy if it gave her a lap dance," she cooed as she lowered herself down onto me, swirling her hips back against me. I gripped onto the edge of the desk with my left hand and bit down on the knuckle of my right index finger.

"Fuck, Jackson, you really are tense. On a scale of one to ten, how bad is it right now? Be honest."

I took a deep breath and steeled myself, trying to seem casual. "About a seven."

"Oh that's far too low, we'll have to work on that." She leaned in and pressed her lips to my earlobe, capturing just the barest edge of skin again her teeth.

"Nine..."

She turned herself around, straddling me, and swung her head to the other ear. "I'm going to wear your cum out of this office, like it's my makeup," she whispered in a voice I'd never heard her use before. She circled her hips, slower but with more pressure this time.

"Twelve."

"That sounds more like where I was hoping you'd be."

Sara pulled down the straps of her dress, revealing the dark blue lace of a pushup bra underneath, and she shimmied the dress down to her waist. While years of carrying toddlers had hardened her arms and legs, motherhood showed through in the softness of her stomach. The slight wrinkle where pregnancy had stretched her skin hid what remained of her abs and reminded me that she was not a woman who was naively falling into this decision. She was mature enough to know what she wanted and to take the opportunities in front of her.

Kneeling in front of me, Sara unhooked the strap of my belt. I expected her to leave it in place, but instead she pulled it completely off. She unbuttoned my slacks, pulling them to midthigh along with my briefs. Without breaking eye contact, she gripped me at my base and swirled the palm of her left hand across the tip. I squirmed in beautiful agony and she grinned.

"Fuck, I need to cum so bad." She nodded, keeping eye-contact as she pumped her left hand up and down. With her right hand, she carefully stroked my balls--first one nail, then two, then her whole hand. Precum leaked from the tip, and without breaking her stroke, she used her thumb to spread it along the underside of my cock.

"Tell me more about what you need." Her eyes stayed locked into mine, but she no longer looked hungry, instead filled with a deep desire to genuinely help me. "How else can I help?"

"God, I want to feel your mouth." Every drunken fantasy from a sandbar Saturday, every horny thought as I watched her sip coffee on a Tuesday afternoon was pouring out of me now. I wanted to see her soft pink lips wrap around me, to feel her tongue as I gripped the back of her head.

"Of course."

Her left hand kept its rhythm, and her right gently cupped my balls as she lowered her mouth around me. My fingers laced their way through her hair, palming the back of her skull. I didn't need to control the pace, as she put perfect pressure against me with her lips and bobbed in a dancing counterpoint to the motion of her hand

I closed my eyes and leaned back, but the peace of the moment was shattered by the ringing of my cell phone. I expected her to stop, to pull away, snapped back to reality, but she didn't. She just looked up at me, with curiosity in her eyes, as if asking "Who is it?"

Ben.

His Facebook picture, a black and white from their wedding, now filled my iPhone screen like a scathing indictment, a searing reminder that I was definitely punching my ticket to the lowest levels of Hell.

"It's Ben, you gotta stop. Fuck." The ring on my phone stopped and I sighed. After a few seconds, the ringing began again. "Shit, shit shit, he's calling again." I'm sure the panic in my voice really sealed my attractiveness, but instead she pulled away for just a moment.

"Don't be a bitch, just answer it." And with those seven words uttered, she resumed the task quite literally at hand.

As if on auto-pilot, I grabbed the phone and attempted to answer as calmly as I could.

"Hey, Ben, what's up?"

"Hey, do you know where Sara is? She's not answering her phone."

"Um, I think she went out to grab coffee before the next client meeting. I can look to see if she left her phone on her desk if you want?"

Ben let out a hearty, knowing laugh. "That's alright, it sounds like you're a little bit busy at the moment. That date with Cassie must have gone pretty well if she's under your desk at the office like that."

My ragged breaths had clearly shattered my Oscar-winning performance of "Man Not Receiving A Blowjob".

"Something like that."

Ben laughed again. "I get it, man! It takes me back to the Chicago conference and Becky-from-Seattle pulling me into the bathroom at the hotel bar. God, she had an ass on her."

Sara pulled away momentarily, and a devious hunger again flashed across her face.

"I want him to listen to us, to me. Tell him I want, well that Cassie wants to put him on speaker phone and let him listen. Trust me, he'll do it." She added the last sentence to cut off the beginnings of my protest.

"So, mmm, uh, this might be weird, but she actually wants to put you on speaker phone and have you listen to us." As I talked, she moved her head with more intensity, more passion. I don't know if it was the idea of revenge or just having an audience, but it was clear how badly she wanted this.

"Hell yeah, bro. I'll gladly be in the audience for your little show." I could hear him unzipping and the beginnings of his rhythmic breathing as he began to enjoy himself too. "She's a little kinky one, huh?"

"So much more than I realized."

I gripped down hard on the back of Sara's head, and started to buck my hips against her face. If she was set on wearing me out of the office like makeup, she was approaching victory. I panted loudly and I could hear Ben groaning on the other end of the line. My grip on Sara tightened, and in her hand, my balls got firm, warning of the impending eruption that would ensue.

"Oh fuck that feels good."

I expected Sara to double down again, to send me careening over the edge. But instead she stop, stood up hurriedly, pulling her dress the rest of the way down, revealing and quickly discarding the matching blue thong she was wearing. I tried to take a moment to take a mental picture of her, of the clearly manicured little strip of hair that remained above her clit, but as quickly as she had stood up, she was clearing files out of the way and bending over against the desk.

"Make him listen to you fuck me," she whispered, at a volume that was probably louder than she expected. On the other end of the speakerphone, I could hear Ben moaning as he worked himself over listening to us.

"I don't have a condom." The alarm bells in my brain were ringing, but I still had my faculties enough to raise the flag for safety.

"You think after the twins I left my tubes untied? I just want you inside me and I want him to hear it." The desperation in her voice was palpable now. I'd have been lying if I said I didn't want her equally desperately.

I guided myself up to her, and began to lean in slowly. She met my patience with aggression, and pushed herself back onto me. She was heavenly and gripped onto her shoulder as she threw herself back into me. She was setting the pace and I just needed to enjoy the ride.

"Fuck you feel so fucking good." I was so lost in the moment that for a split-second, I forgot about our audience and nearly said her name. She moaned out, loudly and I heard Ben groan in call-and-response on the other end of the line.

"Smack that little slut on the ass for me." Ben's directive came through as I concentrated on not enjoying the moment too much, too quickly. Now emboldened, I slapped Sara's soft freckled ass and watched a red handprint bloom across her skin. She moaned again, and I repeated it on the other cheek. She arched back and pressed her lips against my ear. "I want this so fucking bad, and I want him to hear all of it. Tie me up, make me cum and make him listen."

I quickened my pace, now slamming against her harder and harder. I grabbed the discarded belt from the floor and wrapped it around her wrists. I felt her melt, just slightly, as I cinched the belt against her hands, using it as a counter weight to pull myself into her with each thrust.

As I rolled the end of the leather belt in my hand, I groaned. "Cum for me, baby. Be a good girl and cum for me."

"Yes, sir." Again she whispered loudly enough that I worried Ben might hear. But I didn't care anymore. I wanted her, I needed her and I needed this. "I'm almost there, keep going." This one was quieter, like a stage direction from a director who is worried that her star will forget his lines. I gripped the leather of the belt tighter and wrapped my other hand around her waist, leading my fingers to her clit.

"That's it, right there," I heard Ben mutter on the other line to himself, clearly imagining Cassie enjoying herself, face down against my ancient desk.

I fucked Sara harder, and worked my fingers in small circles against her clit. "Oh fuck, oh fuck, oh fuck." The words left her in a climbing staccato and I left her muscles clench and tighten, before releasing as she steadied herself with her forearms.

"I'm serious. I want you to finish on my face," the words fell out in a breathless, rhythmless tumble, as if she had to chase down each word and catch it before she could speak it. I was happy oblige, and I pulled out as she turned to face me. Her auburn hair was sweaty now, her lipstick smudged and mascara clouded the jewel tones of her eyes. I again gripped the back of her head as I pumped myself with one hand. I heard Ben start to climax on the other end, and I felt her tongue, wide and flat against the underside of my balls.

"Oh fuuuuuuuuuucck." I groaned and the word seemed to drag out to infinity as I emptied myself across her face in thick white ropes, stretching from her forehead to the top of her lips. Her right eye was heavy with it, and she squinted to keep it shut while keeping the left open. I closed my eyes, and stumbled backwards, trying to find my sea-legs before giving up and collapsing into my chair.

I heard the click of the call end, and hung my head to catch my breath, while the fabled post nut clarity made me suddenly aware of the fact that I had just cum all over the face of the woman whose kids call me Uncle Jackson. I wiped the sweat from eyes and opened them to see Sara holding my phone in front of her. Her lips were pursed in a pouty kiss, while she made a peace sign with her right hand.

Assuming she was leaving me a tiny memento from our tryst, I let her finish and stuck my hand out for her to return the phone.

I heard the "swish" sound of a message being sent as the phone hit my hand. I opened my messages app.

"What the FUCK! Are you insane?"

Instead of a reminder of our transgression, she had sent the selfie as a confession to Ben.

No words, just the photo of her face, covered in my semen.

"He's going to lose it, you know that right? I'm going to die." The earlier panic now returned, even stronger than before. I stared in disbelief at my phone.

12