Chapter 4: Shara, the Toy Seller
After the trial day with Shelly, everything settled back into its normal rhythm. One morning, however, Jennifer came into my home office before leaving for her day job. It wasn’t totally uncommon, but her quiet, conspiratorial tone felt different.
"Hey, I know we normally don't talk about 'Office Tuesday,' but I think we need to adjust a few things," she whispered.
I looked up from my screen, genuinely curious. "Okay, what's on your mind?"
"First, I think we need dedicated office cell phones—something off-grid we can text each other on and hide later."
I nodded. "Makes sense. I'll get right on that."
She smiled, trailing a soft hand over my cheek. "Second, I think adult toys are in order for this next interview."
I raised a single eyebrow at her.
She smirked. "You'll understand. Just... don't go too wild."
"I can definitely make that work," I replied.
She leaned down, giving me a lingering, passionate kiss. "God, I love you," she murmured before sprinting out the door to work.
Cell phones and adult toys—got it.
I spent the next couple of days getting everything in order. For the phones, I picked up a pair of handsets operating on an unusual frequency, giving me the perfect excuse to build our own private LoRa network. It served a dual purpose: encrypted, off-grid communication untracked by Uncle Sam, and complete privacy for our roleplay games.
As for the toys, not knowing her exact preference, I curated a variety: two classic dildos, two high-end vibrators, and two clitoral suction toys. I stashed them safely in a locked desk drawer alongside the interview files, hidden from any stray eyes.
By Monday morning, Jennifer had slipped a fresh note into my desk binder: Interview confirmed for tomorrow morning at 9:00 AM with Shara. Enjoy, honey—and make sure to put her through her paces to see if she’s a good fit for your new enterprise.
The note brought a wicked grin to my face. I spent the rest of the day drafting a sleek Non-Disclosure Agreement, leveraging Microsoft Copilot for the legal framework and adding a few custom edits to make it look official.
That night, after putting the kids to bed, we made passionate love. I could feel her humming with anticipation for the morning ahead.
The next morning, Jennifer left early under the guise of work, and the kids left for school. After wrapping up my morning routine, I sat at my desk and waited for 9:00 AM.
At precisely 8:50 AM, a sharp, playful knock sounded at my office door.
"Come in," I called out.
The door swung open to reveal "Shara." She wore a flirty micro-skirt—far shorter than her last outfit—a skin-tight noodle-strap top, and towering green high heels. Her makeup was dark and dramatic, framed by a striking platinum blonde wig.
"Oh, hello... is this J&J Investing?" she purred.
"Why yes, it is. Shara, I presume?"
She flashed a brilliant, sultry smile. "Oh, good! I was worried I had the wrong address. Yes, I'm Shara. And you must be Mr. Jack."
I nodded, gesturing inside. "Indeed. You're a few minutes early, but no worries—we can get started right away if you'd like."
"That would be wonderful, if it's no trouble at all."
"Not at all. Please, have a seat." As she took her chair, I glanced over her outfit. "I see you were briefed on the dress code for the role?"
She let out a soft chuckle. "Oh yes, sir. Mrs. Brandson was quite adamant that it be adhered to strictly. I hope this meets your expectations?"
"Normally, standard office attire is a bit more formal, but given the unique scope of this position, I think this works just fine."
She let out a soft sigh of relief. "Good. I wasn't sure how far to push it, but given the job description, I figured you couldn't go wrong with a micro-skirt and heels for a first impression."
"Bold approach," I noted with a subtle smirk. "You certainly make an impression."
She grinned, crossing her long legs and leaning back.
"Now, down to business," I began. She perked up, resting her hands on her knees. "We're here to interview for the executive secretary position. I'm sure Mrs. Brandson gave you the broad strokes, so we'll dive right into the core details."
"Mrs. Brandson gave me the outline—managing day-to-day operations, handling client relations, and catering to any personal matters you might require."
"Good. Let's start with expectations. Privacy and confidentiality are the cornerstone of this enterprise. Our clients—and I personally—require complete discretion regarding anything said or done within these walls. Is that something you can handle, even with the most intimate matters?"
Shara grinned wickedly. "Sir, if you only knew the stories I could tell from my previous role, you wouldn't even have to ask."
"Fair enough, but as standard practice, I require a signed NDA. Everything discussed or executed here remains strictly between us."
I slid the custom document across the desk. She scanned it quickly, signed it with a flourish, and passed it back. I added my signature and placed it aside.
"Now that we're bound by contract, let's get to the meat of your experience," I said. "You mentioned handling intimate matters in your last position. Walk me through your primary duties and how you executed them."
She paused thoughtfully. "Well, sir, on paper, I handled order fulfillment and client relationships for a boutique business."
I tilted my head, prompting her to go on.
"To be more specific... I bought and sold novelty items of an intimate nature."
"So, adult toys," I clarified directly.
She smirked. "Yes, sir. It's usually a bit awkward to state so bluntly, as most employers frown upon it."
"I'm not most employers, and this isn't a standard position," I replied smoothly. "Let me assure you, we call a spade a spade here."
"Understood, sir. Yes, I sold high-end adult novelties. Beyond floor sales, my specialized duty was catering to high-net-worth VIP clients and wholesale buyers. I provided detailed product overviews and... extra encouragement to help them finalize large orders."
"Extra encouragement?" I leaned back, interested.
"To be completely honest, sir, I provided live product demonstrations. In high-stakes cases, I offered personal assistance to ensure they understood the product's full potential. Safe to say, I had far more repeat clients than one-time buyers."
"Care to share how you'd apply those techniques to my clients—or to me?"
She hesitated playfully. "Well, sir, I wouldn't want to divulge trade secrets..."
"Let me rephrase," I interrupted smoothly. "Imagine I'm a prospective VIP client placing a massive order. How do you approach me?"
She rested her chin in her hand, thinking for a moment before her eyes lit up. "First meetings require breaking the ice," she explained. "I'd walk you through the showroom, observing which items catch your eye. Then, I'd use those observations to steer the conversation."
"Give me a practical example."
"Of course. It would help if I had a sample..." She reached into her handbag and produced a sleek, silver bullet vibrator. "If I saw you glancing at this, I'd pick it up and ask, 'What catches your attention about this model?' or maybe, 'I bet your wife would love one of these.'"
I laughed. "Effective—because she actually does have one."
"Oh, I bet she does," Shara purred, leaning closer over the desk. "Discreet, compact, but remarkably powerful. It gets me to the finish line in just a couple of minutes."
"That fast? I would've thought something that size takes longer."
"Not this little guy. He's quick, quiet, and potent." She leaned in even closer, dropping her voice to a soft whisper. "Perfect for quick afternoon breaks. Slide into the restroom, pull your panties aside, and within minutes, any brain fog vanishes."
"Brain fog?" I asked with a smirk. "And what causes this workplace brain fog?"
"Well, sir... sitting across from such a handsome man certainly drives a girl's mind to places it shouldn't go. With the right technique, sir, it's explosive. With a little demonstration, you'd see exactly what I mean."
I rested my elbows on the mahogany desk, giving her a challenged smirk. "A live demonstration, you say? Well, Shara, in this line of work, we prioritize proof over promises. Show me exactly how you'd pitch it."
Shara’s eyes flashed with a dangerous blend of confidence and pure mischief. Without a moment's hesitation, her manicured thumb clicked a concealed button on the silver bullet, and a low, virtually silent hum filled the quiet room.
"It all begins with setting the mood," she purred softly, her tone dropping into a rich, velvety register as she leaned back in her plush chair. With slow, agonizingly deliberate movements, she gathered the hem of her micro-skirt, teasingly drawing it up to reveal her smooth, silk-clad thighs. "When a high-net-worth client is sitting on the fence, you don't merely list features off a spec sheet—you make them feel the potential."
She slid the humming silver cylinder beneath her skirt, pressing the tip directly against her apex over her sheer thong. Her breath hitched instantly, a subtle shudder rippling across her bare shoulders, yet her heavy-lidded gaze remained locked onto mine with absolute composure.
"Pay attention to the acoustic profile, Mr. Jack," she murmured, her voice taking on a husky edge as she began rotating the bullet in tight, rhythmic circles. "You could be sitting in a high-stakes board meeting, inches away from corporate rivals, and not a single soul would ever suspect. Just a slight shift in posture..."
Her back arched gracefully off the chair, her chest rising as a soft, breathless sigh escaped her glossed lips. She demonstrated the pulse settings, switching from a steady rhythm to an escalating wave, her fingers expertly adjusting the pressure. Her cheeks flushed a radiant rose, a delicate sheen catching the light as she demonstrated the technique—holding completely still while letting the targeted vibrations do the heavy lifting.
Within moments, her toes curled into her green high heels. Her thighs trembled, a sudden, intense orgasm washing over her in a shuddering wave that left her momentarily breathless.
She let out one final, satisfying exhale, clicked the button to silence the whisper-quiet motor, and smoothly arranged her skirt back over her legs. Tucking the sleek bullet back into her handbag, she sat up straight, crossing her legs with flawless poise and a triumphant smirk.
"Two minutes flat, sir. Workplace brain fog entirely banished—and the client is thoroughly sold."
I leaned back, genuinely impressed by her complete lack of hesitation and mastery of the presentation. "A remarkably persuasive demonstration," I acknowledged with an approving nod. "You certainly know how to command attention and close a deal."
She beamed, resting her hands back on her knees. "I aim to please, sir."
"Now, let me see how that confidence translates to the rest of our expectations," I continued smoothly, steering the conversation back into our structured outline. "We expect peak performance here. How do you handle constructive feedback or corrective discipline when expectations aren't met?"
A wicked glint flashed in her eyes. "As long as we establish a safe word, sir, I can handle whatever discipline you dish out."
"Fair enough. Now, any constraints with travel or late hours?"
"None at all, sir. Single, no pets, fully flexible."
"Excellent. Let me introduce you to a practical scenario: demonstrate how you attend to a prospective client while they wait for my arrival. Let's call him 'Mr. Johnson'—and I'll be playing his role today."
I unlocked my desk drawer, pulled out the collection of toys, and set them on the blotter.
Shara gasped playfully. "And here I thought you came empty-handed!"
She scooped up the toys, placed them on her chair's side table, and stood up. She immediately slipped into character, striding toward my desk with a seductive sway.
"Mr. Johnson, I am so sorry for the delay," she purred, planting one cheek on the edge of my desk and crossing her legs at the ankles—giving me a breathtaking view of her skimpy thong beneath the micro-skirt. "Mr. Jack is finishing up a meeting, but he asked me to make sure you're thoroughly taken care of while you wait. Is there anything I can do to make your stay more... comfortable?"
"I think I could be persuaded," I replied, leaning back with my hands behind my head.
"I thought so," she murmured, tracing a manicured fingernail down my arm. "Let me pour you a drink."
She stepped over to the executive bar, returning with a crystal glass filled with top-shelf vodka. Setting it down, she looked at me with heavy-lidded eyes. "You look like a gentleman who appreciates seeing what a woman can handle."
She squatted down, picked up a large dildo, and placed it on the desk. "Mrs. Brandson always makes sure I have fun little toys available in case our guests get bored. Shall we see if this fits?"
"Only one way to find out," I challenged.
Shara slid her thong aside, positioning the smooth silicone against her slick pussy. She fed it inside slowly, letting out a series of husky, convincing moans.
"Oh god... it's so thick... I can feel it deep inside me..." she gasped, working the shaft in and out, putting on a breathtaking performance.
Watching her work herself to a shuddering climax sent a jolt straight to my lap. I reached down, stroking my hard cock through my trousers.
Noticeably tracking my movement, Shara purred, "It's alright, Mr. Johnson... take it out. I want to watch you enjoy this."
She continued riding the dildo while I unzipped and freed my throbbing erection.
Her eyes widened in mock surprise. "Oh my... you didn't mention you were packing so much heat, Mr. Johnson!" She gave a playful wink. "I don't know if I can take all of you..."
"Only one way to find out," I echoed.
Shara immediately dropped to her knees, taking my cock in her hand and trading the toy for the real thing. She guided my tip against her dripping entrance and sank down onto my shaft.
"Oh fuck, sir... you feel incredible!" she moaned, her inner muscles clenching tightly around me. She rode me briskly to another intense orgasm, her body quivering over mine.
As her spasms ebbed, I gripped her hips, slid her across the desk blotter, and pulled her ass to the edge. I drove deep into her dripping heat, pacing my thrusts until a surge of pleasure washed over me, spilling my seed deep inside her.
Clenching around my release, she let out a soft sigh and sat up, adjusting her blonde wig with a wink.
"Now, how was that for service with a smile?"
"Extremely impressive," I grinned, catching my breath. "How far are you willing to take this client care?"
"As far as duty requires, sir."
"Tell me how you see yourself attending to my personal needs on a regular basis," I asked.
She touched a finger to her lips thoughtfully. "With you, sir, it would be much more intimate and personalized. I like to study my long-term clients—figure out what drives them, what they secretly desire but might be hesitant to ask for at home. It's an ongoing journey of exploration."
"Elaborate."
"Well, beyond the daily routine—spontaneous blowjobs, office quickies, roleplay—I'd introduce new elements gradually. A finger in your ass, light restraints, or wearing a plug during office hours. Endlessly tailored to your desires."
"Masterful approach," I acknowledged.
"May I ask a question, sir?" she requested. "You mentioned corporate retreats and business travel earlier. How do you envision those unfolding?"
"We're expanding rapidly," I explained, playing along. "I need personal retreats to recharge, stay focused, and plan quarterly strategy. Your role would be orchestrating the logistics and ensuring I stay relaxed."
"Should clients be included in these retreats as a corporate perk?" she asked, her eyes lighting up.
"That's an intriguing idea. How would you structure a client retreat—say, for a client who loves secluded mountain cabins?"
Shara stood up, pacing the floor with a wicked grin. Her tight skirt hugged every curve of her hips as she walked, creating an extraordinarily distracting view.
God, her ass looks unbelievable in that outfit, I thought, captivated by her movement.
"Picture a secluded three-bedroom cabin deep in the woods—complete privacy," she began, turning to face me. "Mornings are for business strategy over breakfast. During lunch, entertainment to keep your energy high—perhaps a private striptease on the dining table, or serving lunch in a bikini before giving you both lap dances."
She pulled down her noodle straps, exposing her full, gorgeous breasts. "While you wrap up afternoon work, I take Mr. Johnson to his room for personal attention..."
She picked up the dildo, stroking it and taking the head into her mouth for a deep, sensual blowjob right in front of me.
"Once he's catered to," she continued, slipping the toy from her lips, "I return to help you unwind. Evenings are for the hot tub, drinks, and unrestrained group fun."
She slipped out of her skirt, leaving only her sheer thong, and climbed onto my lap, pressing her bare breasts against my face. I buried my head between her soft mounds, kissing and sucking her nipples as she stroked the dildo against her thigh.
She pulled me into a deep, passionate kiss. Then, crawling onto the desk, she positioned the dildo beneath her and guided my re-erected cock back into her mouth.
The scene was breathtaking. She rode the toy while taking my hard shaft deep into her throat, moaning through her intense orgasms.
I gripped her waist, spanked her bare ass with a few resounding slaps, and fucked her hard from behind as she sucked the dildo.
"Fuck me deep, Jack... I want your cum!" she gasped, switching her mouth back to my cock just as I reached my peak, swallowing every drop of my release with a quiet moan.
After catching our breath, Shara pulled her thong into place and gathered her clothes. "Let me go freshen up, sir."
When she returned, I checked the time. "I lost track of the hour. Shall we order lunch in?"
"I'd love that," she smiled.
We ordered takeout. When the food arrived, Shara threw on her jacket to grab the delivery from the porch before laying out the dishes on my desk.
Between bites of fried rice, I asked, "So, your retreat planning concept—do you have actual experience organizing multi-guest entertainment?"
"Not formal trip planning, but entertaining multiple guests simultaneously? Yes," she answered casually. "At my old job, business partners would come in together to 'inspect wholesale orders.' I'd demonstrate products for them, which quickly turned into live shows. Once, I had one client fucking me from behind while I sucked off his partner. They ended up placing a massive order, and my boss gave me a ten percent bonus!"
I smirked. "Impressive sales tactic. What about your favorite solo clients?"
"I had two favorites," she shared, resting her chin on her hand. "One was extremely dominant—loved commanding me to test toys on the spot in the warehouse or bending me over for hard spankings until my ass was bright red. The other was all about intimate exploration—we started with standard play, moved to rimming and prostate play, and eventually, I was pegging him while he shot mind-blowing orgasms across his chest."
She gave me a sweet smile. "No limits, sir. Whatever makes my employer happy makes me happy."
After finishing lunch, I handed down her trial assignment.
"Your first official task: outline a comprehensive five-day corporate retreat. Private, secluded, fully scheduled with activities, dining, and attire requirements. Budget is five thousand dollars. I need it by the end of the day."
She took a pad of paper and went to work at the small side table.
An hour later, she presented me with a brief, one-page outline. At the bottom, she had cheekily scribbled: Spank me hard.
I took the hint immediately. "This is a decent start, Shara, but nowhere near detailed enough for my standards," I said, stepping around the desk. "In this firm, I demand perfection. Pull down your panties."
Her eyes widened in playful shock, but she obeyed instantly, bending over the desk.
CRACK! CRACK! CRACK! CRACK!
I brought my hand down four times across her smooth, bare cheeks, delivering firm, stinging slaps.
"Fuck! Yes, sir!" she gasped, squirming against the wood.
"Moving forward, I expect flawless execution," I reprimanded, landing four more hard slaps. "To ensure you stay focused, leave your top here on my desk while you revise it."
She blushed, peeled off her shirt, and handed it to me. Topless and glowing from the discipline, she returned to her work.
By late afternoon, she presented a much more detailed breakdown.
"Better," I approved. "Take this home as your final assignment and detail the complete itinerary. Here is your official encrypted cell phone—keep it on you at all times."
"Understood, Mr. Jack."
"Before you leave, I need a series of reference photos for our internal portfolio—to demonstrate to prospective clients the level of personal service we provide."
"Just for your personal collection?" she teased with a smirk.
"Strictly under lock and key," I assured her.
She spent thirty minutes posing in various alluring angles, sending a full set of photos directly to my secure cloud storage.
She put her top back on, gathered her things, and offered her hand. "It was a pleasure, Mr. Jack. I look forward to our next session."
"Likewise, Shara. You did exceptional work today."
A few minutes after she walked out the front door, my main cell phone buzzed with a text from "Jennifer":
“On my way home, honey! Should be there in about 30 mins to start dinner. Phew, what a long, hard day! But I think I made a great first impression and landed my first big assignment 😉”
I chuckled, replying in character:
“I’m sure you blew them away! Take your time coming home. It’s been a long day here too—these job interviews really take it out of a guy.”
“I bet they do! But was it fun at least? How did she do?” she texted back.
“She was amazing. Knew exactly how to handle every request, completely attentive to client needs. I’m eager to see the full corporate retreat proposal she’s drafting.”
“Ooh, sounds like quite the assignment! I know how important it is to have someone who can manage both the business and your personal needs.”
“She definitely demonstrated fantastic range.”
“Glad to hear it, love you! I’ll get Shandra prepped for the next interview sequence.”
“Sounds like a plan. Love you, see you soon.”
