It was a solid three days before either of us brought up the game, but on Friday evening, Jennifer curled up tight against my chest, the soft warmth of her body settling over mine.
"Oh, by the way," she murmured against my collarbone, her fingertips tracing idle, teasing circles across my ribs. "For the next two weeks, I have back-to-back work-from-home days. You know what that means."
I smirked, resting my hand on the curve of her hip and looking down into her eyes. "Do I get to test out two new secretaries?"
She playfully slapped my chest, a low chuckle rumbling in her throat. "Well, you do have one more interview lined up... if you think you're ready for her."
"More like, are you ready?" I countered softly.
She let out a soft, shuddering moan at the memory, burying her face into the crook of my neck. "Oh, more than ready. That last interview still has me sore..." She snuggled closer, pressing a sweet, lingering kiss to my skin. "I can't wait to see what you do with the next one."
The next morning, her lingering comments had my mind spinning with anticipation. Sitting down at my private desk, I noticed the neat stack of resumes in my bottom drawer looked subtly disturbed. I pulled them out and found a fresh candidate file for Shandra. Tacked to the top corner was a pastel sticky note written in Jennifer’s elegant handwriting:
This one is going to be different. Be patient and persistent. She will come along if you give her a good reason to—and once she's on board, she's going to be the best of them all.
I raised an eyebrow, scanning the resume. It was deceptively straightforward—a pristine, understated history showing almost no traditional corporate experience outside of fifteen years as a devoted stay-at-home mom and housewife. I searched between the lines, wondering what subtle thrill Jennifer was weaving into this persona. After scanning it a few times without cracking the code, I scribbled a return note for Mrs. Brandson:
Please schedule for Tuesday and ensure you send her the standard packet.
By Monday afternoon, a follow-up note rested on the corner of my desk:
Interview scheduled and packet sent. She doesn't have much traditional experience, but she has immense potential. One thing to consider: test her loyalty to the office.
I took that as my cue to devise a custom scenario. All through Monday evening, concentrating on market data was nearly impossible; my mind kept drifting back to her previous transformations, marvelling at how seamlessly Jennifer threw her entire soul into each character.
Tuesday morning arrived under a clear sky. After seeing the household off, I spent an hour at the gym, burning off excess energy. Per our ground rules, Jennifer had already checked into a nearby hotel room to prepare her wardrobe and hair so the encounter would feel entirely authentic. At eight-thirty, I showered, threw on a dark fitted suit, and headed to my home office to monitor my market positions before her scheduled arrival.
At nine-fifteen, a gentle, almost hesitant knock sounded at the heavy wooden door.
"Come in," I called out, setting my pen down.
The door swung open slowly, and in walked my new candidate. She wore a honey-blonde wig styled in soft, modest waves, partially obscured by oversized sunglasses. Her outfit was the picture of suburban modesty—a long, flowy brown-and-white sundress that draped loosely over her curves, sensible low heels, and a heavy leather handbag slung over her shoulder. It was a stark departure from our official dress code, but I leaned back and played along.
"Mr. Brandson?" she asked, her voice small, quiet, and fluttering with uncertainty.
"Yes. And you must be Shandra."
She perked up slightly, adjusting her purse strap. "Yes, sir," she murmured, her tone gentle yet laced with a subtle undercurrent of nervous excitement.
"Please, come in and sit," I said, gesturing to the leather chair across from me.
"Oh, thank you, sir. I can't even begin to tell you how grateful I am for the opportunity to interview for your executive secretary position."
"No problem at all. Let's get started, since we're running a few minutes behind."
A deep, rosy flush crept up her neck, staining her cheeks. "Oh, sir, I am so terribly sorry. Traffic was an absolute nightmare after dropping my son off at school."
"You're here now. No harm done."
She set her heavy bag on the floor, pulled out a neat folder, and leaned across the desk to hand it to me. Affixed to the cover was a yellow sticky note bearing a handwritten message: Firm but fair inside a heart labeled J.B.
Message received—Mrs. Brandson wanted me to take an unyielding, dominant authority over this meek housewife.
"That's a copy of my resume, along with a few letters of recommendation from folks at my church," she explained, a touch of timid pride bleeding through her flustered demeanor.
"Thank you, Shandra. I'll review these, but first, I want to make sure you're completely comfortable." I stood up and leaned back against the edge of the desk, towering over her.
"Oh dear, I'm just terribly nervous, sir," she confessed, her fingers twisting together in her lap. "I haven't interviewed for a proper job in... well, in quite a long time."
Deciding to close the distance, I dragged my leather chair around to the front of the desk, sitting directly across from her so our knees were inches apart. "Let's make this a conversation. Before we dive into your background, there are a few absolute expectations we need to establish."
She nodded earnestly, reaching down for her bag. "Of course, sir. Let me just take a few notes..."
I reached out and laid my palm firmly over her exposed kneecap.
She flinched, her breath hitching sharply. "Oh! Sorry, sir... you startled me."
"It's fine. No notes needed," I commanded softly. "Just sit up straight and hear me out."
She immediately adjusted her posture, pulling her shoulders back and lifting her chin. "Yes, sir. I'm ready."
"First, I require absolute adherence to office policy. Second, I demand strict confidentiality. Whatever happens in this office—between clients, staff, or you and me—stays within these walls. That is an absolute expectation, even during a trial period."
She pressed a manicured finger to her lips, tilting her head thoughtfully. "So... if my husband called to ask how the interview went, what would you tell him?"
I smirked, leaning in closer. "I'd tell him his wife is a polite, intelligent applicant who seems very eager to find the right fit."
"You wouldn't tell him I was late?"
"I keep personal business private. I expect the exact same ironclad discretion from my staff."
She let out a soft, relieved sigh. "Sir, I've been keeping my husband's and my church's secrets for fifteen years. You won't have a single concern there."
"Then you won't mind signing the non-disclosure agreement." I handed her the document and a pen.
She signed her name without a second's hesitation. "To be honest, sir, Dick hasn't taken an interest in me for more than a few seconds a day in years. This will be such a relief. "
"Good. Now, two administrative matters. First: tardiness. In this office, unpunctuality requires immediate disciplinary measures."
Her dark eyes widened behind her light lenses. "Punishment, sir? What kind?"
"For a first offense, a firm spanking over my knee or mundane corrective tasks. Continued tardiness results in escalating consequences."
She instinctively tucked her hands beneath her thighs, squeezing her knees together. "I assure you, sir... it won't happen again."
"Glad to hear it. Second: uniform policy. Did Mrs. Brandson forward our dress code requirements?"
She grimaced slightly, a faint blush returning to her cheeks. "She did, but... I simply couldn't bring myself to buy those clothes. The only word that came to mind was... slutty."
"Accurate," I replied smoothly. "And as we speak, we are heading down that exact path. If you wish to decline the position, you may leave right now—provided you remember your confidentiality agreement."
A subtle, wicked smirk crossed her lips, betraying the timid housewife persona for just a fraction of a second. "Sir, who would I even tell? My husband wouldn't believe anyone would want to look at a woman my age in an outfit like that."
"I am the sole judge of what my clients want to see," I countered, my voice dropping into a stern command. "Our dress code is designed to keep high-value clients engaged. My staff must be willing to go the extra mile."
"I'm afraid you have the wrong woman, sir. Babies and age have taken their toll."
"That is my decision to make," I said, standing up and extending my hand to pull her up. "Shall we proceed with the practical portion of the interview?"
She hesitated, then slipped her small hand into mine. "If you don't think it's a complete waste of your time, sir."
"You are currently out of uniform, Shandra. Please remove the dress."
Her breath caught sharply in her throat. She looked at me, searching my face for any sign of hesitation, before reaching back to pull down the long zipper. She slid the flowy fabric over her shoulders, letting the brown-and-white dress pool around her ankles. She stood before me in full-coverage, modest ivory undergarments, her arms folded tightly across her chest in bashful defense.
"The underwear is non-compliant as well. Off."
She swallowed hard, her chest heaving. Slowly, she unhooked her bra and stepped out of her panties, covering her bare center with trembling hands.
"Sit down, Shandra. Today, this is your uniform."
She lowered her arms, crossed her legs tightly at the knee, and sat back in the chair, her entire body flushed crimson. I began walking her through her daily duties—starting with bringing me my morning coffee. She stood up and executed the task entirely nude, her hips swaying with nervous grace as she walked across the Persian rug to set the warm mug on my desk.
"Now," I continued, leaning back into my chair, "after coffee, I reserve time for personal relaxation. I expect my executive secretary to assist me."
She looked down, her gaze lingering between her own thighs, where her body was betraying her timid act with visible moisture. "Could I... see you first, sir?"
"Handle that yourself," I instructed.
Without a word, she dropped to her knees between my legs. She unbuckled my belt with surprisingly deft fingers and pulled down my trousers and briefs, freeing my stiff, heavy erection. She gasped softly, her eyes wide as she looked up at me.
"Sir... it's so large. I haven't handled anything like this since college..."
"On your knees, Shandra. Mouth open."
She complied instantly, tilting her head back and extending her wet tongue. I guided my shaft past her lips, pushing deep into her mouth. As her throat yielded to my length, her timid inhibitions melted away into raw, primal submission.
"Thirty years ago, you knew how to take care of a man," I growled softly, establishing a steady, forceful rhythm against her lips. "Your body remembers."
She moaned heavily around my shaft, her hands gripping my thighs for leverage while her other hand slid down between her own legs, her fingers working rhythmically against her sensitive center. Within minutes, her timid suburban facade shattered completely. She pulled back from my lap, her eyes dark, heavy-lidded, and wild with desire.
"Fuck me," she gasped.
I grabbed her by the hips, spun her around, and bent her sharply over the polished edge of the desk. Parting her thighs, I aligned my tip with her soaking pussy and drove deep inside in one heavy thrust.
She let out a loud, breathless scream that echoed off the office walls. Her tight inner muscles clamped around me like a vise as I set a punishing, relentless pace. Wave after wave of intense orgasms ripped through her frame, her fingers clawing at the blotter as she rode the climax. By the time I pushed deep inside her and released my heavy load, she was panting heavily, her forehead resting flat against the cool mahogany.
"God," she panted, a dark, triumphant grin breaking across her flushed face as she turned her head toward me. "I haven't been fucked like that in a decade."
"I plan on making full use of my newest office slut," I said, looking down at her bare, glistening body.
"I'm yours to do with what you need, sir," she whispered softly, her voice dripping with absolute submission.
After she cleaned up in the adjoining bathroom, we ordered Mexican food to the office and spent an hour mapping out her ongoing "training program." To test her discretion, I picked up a black marker and wrote Office Slut in clear, bold letters across the skin just above her waistline—a hidden mark she’d have to keep concealed from her husband for a full week. I assigned her home practice routines using heavy-duty office toys, handed her a company credit card with a $1,000 monthly allowance for proper attire, and issued her a secure, encrypted company phone.
She took the phone with a slow, confident smile. "I'll keep this safe as hell, Mr. Brandson."
While she cleared away the empty food containers, I checked my trading dashboard. Both active market positions were closing out near their targets, so I adjusted the take-profit and stop-loss levels, locking in our margins before waiting for her to return.
When she swayed back into the room and sat across from me, she rummaged through her heavy handbag, pulled out a notepad, and jotted down a few crisp lines. "Okay, sir," she said, looking up with wide, dutiful eyes. "What would you like to discuss next? What does your afternoon look like?"
"I have two final tasks for you," I said, leaning back into my leather chair. "First, I need photos for our client files so they know the exact caliber of service they can expect—and in your current state of dress, you'll certainly impress them. Second, I want to see how you handle our primary clients under pressure."
She glanced nervously toward the leather bag where the two large silicone dildos rested. Seeing her hesitation, I smiled, letting my gaze drift down her bare frame. "Why don't you take your new company phone into the adjoining bedroom, handle the photos, and get thoroughly acquainted with the clients? When you're ready, come back and show me what you can do."
Her cheeks flushed a deep, rosy pink. She gave a quick, breathy nod and clutched the bag to her chest like it was packed with dynamite before retreating behind the bedroom door.
A few minutes later, three notifications chimed on my encrypted phone. The first photo showed her kneeling on the mattress, her spine arched gracefully, holding her breasts up to the lens—strikingly seductive and surprisingly elegant. The second captured her reclining with her legs spread wide, her pink tongue caught teasingly between her teeth. The third was a sharp, angled shot from behind, bent forward over the footboard to showcase every sleek, flawless inch of her body.
About thirty minutes later, a soft, deliberate knock rattled the wood. Shandra walked back into the office, holding a slick silicone dildo in each hand, her chest heaving against her top. "Okay, sir," she whispered, her voice tight with nervous anticipation. "I'm ready to give this a try."
"Let's see what you've got."
She stepped up to the desk, placing one toy on the dark wood and the other on the leather chair beside it, aggressively coating both in a thick layer of clear lube. Taking a steadying breath, she slipped seamlessly back into her breathy, anxious persona.
"So, Mr. Johnson..." she murmured, positioning her hips directly over the desk piece. "I see you're in need of a little assistance. Why don't I just..." She lowered herself onto it with agonizing slowness, gasping audibly as the heavy silicone filled her. "Oh, Mr. Johnson... you are so big... oh, sir..."
Without missing a beat, she turned her attention toward the chair. "And Mr. Baxter... you look like you need help too." Leaning down, she took the second piece into her mouth, swirling her tongue around the slippery tip while rhythmically riding the first. "Oh, fuck... I'm going to cum, Mr. Johnson..." She shuddered, her pale thighs quivering violently as a sharp wave of pleasure washed over her.
Switching positions, she sat directly on the second toy, riding it with deep, wet slide sounds that echoed through the quiet office. "Oh, Mr. Baxter... you feel so good inside me..." She looked over at me, her dark eyes flashing with a wicked, mischievous glint. "Oh, Mr. Brandson... why don't you join us? I'm sure we can manage one more."
I stood up and stepped around the heavy desk. Within seconds, her trembling hands had my trousers down to my knees. She took my erection eagerly into her mouth, her throat swallowing me whole while her lower body continued to move relentlessly against the toy. She climaxed again right there, her body shuddering against my legs.
When she finally slid off the toy, she bent forward over the polished edge of the desk, guiding my head into her wet heat from behind while keeping the silicone toy positioned firmly in front. "Now, Mr. Johnson, you weren't supposed to need more attention... but let me help you," she moaned into the dark wood.
I gripped her hips firmly, driving deep into her tight, slick pussy. The combination of the filthy roleplay and her breathless responsiveness sent her over the edge repeatedly. "Oh, fuck... so deep... so fucking deep..." she whimpered, her breath coming in ragged, broken bursts until her forehead rested against the cool wood of the desk.
"You're making me cum again, sir!" she cried out, her calculated acting completely dissolving into raw, genuine sensation. "Please... don't cum in me... if my husband finds out I took such a big cock, he's going to kill me!"
"What's wrong, Shandra?" I teased, rolling her over, pulling her soft legs up over my broad shoulders, and plunging back inside her. "Scared he'll figure out you're the office slut?"
She let out a loud, shuddering moan, her inner muscles clamping around me like a vise. "God, yes! Fuck me harder!"
She locked her legs tight around my waist as I reached my peak. I had intended to pull out, but her desperate grip held me anchored, and I emptied myself deep inside her. She let out a long, trembling sigh, her chest rising and falling heavily as she held me close.
"Oh, god... I didn't know I needed that so much," she whispered softly against my chest.
When I finally pulled back, she stretched her legs out across the dark wood, looking up at me with a lazy, satisfied grin. "So... did you enjoy that, sir?"
I smirked, gesturing down at myself. "You tell me."
She looked down, her cheeks dimpling with a seductive smile. "Well, sir, not to be bold, but I think he enjoyed it very much."
Arching her back, she swung her legs off the desk and stood up, casually smoothing her disheveled hair. She leaned in close, her warm breath tickling my ear as she whispered, "Can I tell you a secret, Mr. Brandson? I'm pretty sure I'm going to remember this interview for a long, long time. And I want this job so bad I can taste it."
"Well, ma'am, you've got the job. We just need to get you fully acclimated to the work environment."
"Oh, we definitely will," she smirked, glancing down at her watch. "Lordy, look at the time. I need to get home."
She packed her toys neatly back into her bag, pulled her original outfit back on, and blew me a lingering kiss before slipping out the office door.
After cleaning up, getting my suit back in order, and checking my portfolio—both market trades had hit their exact profit targets, netting a lucrative gain—my personal phone buzzed on the desk.
Jennifer: Hey there, handsome! Hope you had an amazing day. I should be home in 30 or so, but I am so, so tired. Worn out completely.
Jack: Long day at the office? How did the interview go?
Jennifer: Oh, the interview went very well! A few minor details to work on, but nothing major. I got the job! Starting next Tuesday.
Jack: Glad to hear it. Made a good impression, then?
Jennifer: I think so! He really seemed to like me once I got over my nervousness. It was so intense, you wouldn't believe it.
Jack: Oh really? Why's that?
Jennifer: Just in my head! I swear it felt like I was standing there naked answering questions. But hey, I landed the job!
Jack: Glad you pulled through. I know how excited you were.
Jennifer: I am, but I'll need your help. He mentioned some days I might have to work late or travel for clients. All expenses paid, but I'll be away from home a bit.
Jack: We'll manage. Hopefully the overtime pay is worth it.
Jennifer: Oh, definitely aiming for that overtime ;) See you in a few!
A second later, my encrypted work phone chimed with a message from an unlisted number.
Shandra: Good afternoon, Mr. Brandson. I wanted to thank you for this incredible opportunity. I can't stop smiling, even sitting in traffic with proof of my interview sliding down my leg. If you ever need me to stay late or come in early, please let me know.
Jack: Glad to hear you're so dedicated. Remember your training assignments and the dress code for next week. I'd hate to start Tuesday with you over my desk receiving disciplinary spankings for being out of uniform.
Shandra: To be honest, sir, I might enjoy that. I'll make sure I meet your exact standards next week.
Jack: Good. Have a great evening. You earned it.
A moment later, a final text came through from Jennifer on my personal line.
Jennifer: Hey, Mrs. Brandson wants to meet with you on Wednesday. She wants to debrief on the candidate interviews and discuss how we move forward with the office structure.
Jack: Book it. I'll be there.
Jennifer: Dinner then. And you're taking me out.
Jack: Buy a new dress and I will.
Jennifer: Don't tempt me, boss. I have a company card now.
