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The Secretary's Second Interview

"A joke turned into fantasy."

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So the following Tuesday came around. After the kids left for school, I was sitting in my office, spaced out looking at charts and planning my next few trades for the week, when I heard a knock on the door.

​"Come in," I said wearily.

​My wife opened the door and said, "Good morning, sir. Reporting for duty."

​She stepped fully into the room, and I saw she had the skirt and white blouse on again. It was unbuttoned just like I had left it the night we did her mock interview.

​"I apologize for being late, but I had to change when I got here," she said.

​I raised my eyebrows at her, and she stealthily sat down on the edge of my desk, crossing her thick legs.

​"Well, your dress code is quite... demanding, and I didn't want my husband thinking anything he shouldn't," she said.

​I nodded, deciding to play along with her line. "Well, then there's no reason for you not to be following the dress code now, is there?"

​She gave me a quizzical look, so I continued, "For instance, we spoke about your skirts last time we met, and this is still too long for my office. Your shirt is a bit too loose as well," I said, leaning back in my chair.

​She offered a mock blush and put her hand over her mouth. "But sir, if it's any shorter, it would be hard for me to not... well, show things to the clients."

​I smiled. "Mrs. Brandson, you asked for this job, and this is standard. I expect nothing but the most deliberate attention to this area." I added, "However, it's understandable that such changes may cause confusion for you and your family. So, here is a company card. I expect receipts for your purchases, but ensure that anything you buy meets my guidelines."

​She smirked and took the credit card. "Yes, sir. I will ensure I have appropriate attire from now on. While I'm here, is there anything I can do for you, sir?"

​Smiling back at her, I said, "As a matter of fact, yes. You can get me my coffee."

​She swayed seductively out of the little office and went to the kitchen. While she was gone, I began writing down mock rules for office attire as a joke, just to see how far she would take it.

UNIFORM CODE

▪ Skirts must be no longer than wrist length at all times.

▪ Shirts must be form-fitting with a very low neckline.

▪ Shoes must have at least a 4-inch heel.

​I paused at the shoes and wondered if I should keep going. When she came back in and bent over seductively to place my coffee on the desk, I decided I definitely should. As she sat across from me on the other side of the desk, I wrote:

​▪ Undergarments: If a bra is worn, it must be lace or see-through material. If panties are worn, they must be thong or G-string style. If nylons are worn, they must be see-through, thigh-high style. Lingerie is permitted as long as it matches the above criteria.

​"Is there anything else I can help you with, sir?" she asked.

​I replied with a smile, "As a matter of fact, you can please type this uniform policy up and present it to me for final approval."

​I handed her my notepad as she stood up. Her eyes popped, and as she looked up, my smile deepened. She eventually smiled back, took the pad, and grabbed her laptop from the living room. She began typing while I watched her work. When she was done, she printed it out and handed it over.

​I read through it slowly, then said, "Mrs. Brandson, you missed something."

​"Oh, what is that, sir?" she asked, popping up from her seat.

​"Come here and let me show you," I said, sliding back from my desk and patting my leg.

​She took the hint and sat on my knee while reading over my shoulder. "I think I have everything. I have the skirt length here," she said with a smile. "The top requirements and the shoe requirements here," she pointed out, arching her back. "And see here, I even included the undergarment requirements."

​I nodded, gripping her waist with my hands and leaning in. "Yes, you did all that correctly, but down here, I think we need a signature field for us to agree to these terms if you're going to work here. And possibly a line about how disciplinary action will be at my discretion if you violate our dress code."

​She smirked at that and slid back slightly on my lap before getting up. "Oh, yes, sir. I think I can add those items in."

​As she sat back down, I added one more thing: "Oh, and Mrs. Brandson, one more thing to add: if I buy you something to wear, you are required to wear it."

​She gave me a deep look of dramatic exasperation before typing it up.

​After she printed the updated copy, she brought it back, leaning over my desk beside me to show it off. "Here are all your requirements about the wardrobe, here are the other items you wanted me to add, and lastly, here is where we sign."

​I nodded in agreement. "Very well done, Mrs. Brandson. Now I think it's time to formalize our agreement, don't you?" I pulled out a pen and signed my name to the document before handing it to her.

​"Why, yes, sir, I think it is." She took the pen and signed her name.

​"Now that we have that done, I think it's time we discuss your other duties around the office," I said, leaning back in my chair and slowly spreading my legs apart. "During your interview, you mentioned you had certain skills you would bring to the office."

​Her smile widened, and as she locked eyes with me, she said in a seductive voice, "Oh yes, sir. I definitely have skills I think you will appreciate daily, sir. Would you like me to demonstrate some of them for you?" She gathered her hair in her hands and pulled it into a bun.

​"Yes, I think we have some time before my next meeting. Let's see what you're bringing to the table, so to speak," I replied, watching her hike up her skirt around her thick thighs.

​She knelt down between my legs. "So, depending on how much time we have, I can be quick and efficient, or I can be slower, more thorough, and more creative with my work."

​Sliding her hands up my thighs to my stomach, she continued, "But of course, with a man like you, discretion is key for every detail of our agreement. So..." She slowly pulled a finger up my chest to my lips. "...no one will need to know about my special duties."

​I smiled down at her, feeling her finger slide down my neck again. "Exactly what I was thinking, Mrs. Brandson. The work you do here is confidential, and no one other than us needs to be privy to such arrangements."

​She smiled back, lacing her fingers under my belt buckle, gradually unfastening it. "Oh, of course, sir. And if there are things you're not getting help with elsewhere, I wouldn't mind helping you with those, either. Just know I am more than happy to fulfill any desire..." My buckle came undone. "...or any longing..." My zipper slid down. "...you may have."

​She pulled my pants down past my waist. "So, do we have a little time, or do you require longer, more detailed assistance?"

​I smirked. "For now, let's just begin with a quick overview of your skills and services. We can move to a more lengthy demonstration later this afternoon."

​She gave me a you-don't-know-what-you're-missing look before wrapping her hand around my shaft. "Ummm, god, I just love this," she said, gripping the base tightly. "I didn't tell you this after our interview, but I was so worn out I was sore for days."

​She slid my cock into her mouth and ran her tongue up the shaft. After a few motions, she paused, letting her tongue slide off the tip. "I've been so excited to service you again while I waited for today," she said before taking me back into her mouth.

​She moved slowly, going all the way down to her hand before pulling back. "I so thoroughly enjoyed watching you grow last time and hearing you tell me how much you liked it."

​She went back down on me, letting her hand fall away as she took my growing cock deeper into her throat. She gagged slightly before coming back up. "I couldn't get you out of my mind. I kept having to sneak away to..." She paused, looking up at me as her tongue rolled around the tip, "...relieve myself from the ache."

​She went all the way back down, moaning as she bottomed out. Both of her hands gripped my bare butt cheeks, pulling me closer.

​When she pulled back, she gripped my shaft with one hand and wiped her mouth with the other, gesturing for me to stand up. As I stood, she moaned and ran her tongue down my shaft to my balls. Sliding them into her mouth, she gripped my ass again, then licked her way down past my testicles to my taint. She lingered there before working her way back up.

​She took my entire length into her mouth again, gagging slightly but not stopping. I took hold of the back of her head, gently guiding my hips toward her. She dug her nails into my ass and pulled me closer.

​Hard as a rock, I was dying to release, but I wanted her pussy first. I pulled back. With a sigh, she gave me a mock-disappointed look, but as I helped her stand and guided her over the edge of the desk, her smile returned.

​I pulled her skirt up and slid her panties down, spreading her legs as I pushed inside her.

​"Oh fuck yes, I need that cock," she moaned as I slid deep inside.

​When I bottomed out, she arched her back. "Fuck, you feel so good in me. God, that big cock feels so good."

​In the heat of the moment, I said, "That's it, baby, take it," and began pounding toward an orgasm.

​She climaxed within moments, holding her breath before letting out a loud moan. "Fuck yes, harder... oh god, it's so big." She came again just as I was reaching my edge. Her inner grip tightened so intensely it stopped me in my tracks for a second.

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​Once the intensity passed, I drove in deep and hard until I felt the surge build, releasing in a heavy orgasm. Out of breath, I sat back down in the chair with my pants around my ankles, admiring her.

​As she began to recover and reached for her skirt, I said, "Leave the panties off. I think I want more of that later."

​She smiled. "Oh, yes, sir," and tossed them across the room.

​She walked over to me, adjusting her skirt. "Maybe next time we'll have a little more time for a... well, more thorough examination of what services I can provide you, sir." She zipped up her skirt and walked out to the bathroom.

​After getting myself together, I went back to work—checking trades, backtesting, and researching market setups. Around noon, my stomach started rumbling.

​"Mrs. Brandson, are you hungry?"

​She quickly and dutifully called out, "Oh, sir, I am so sorry! What would you like for lunch?"

​I squinted in thought. "You know, I'm not sure. Let's go out and find something."

​Her eyes nearly popped out of her head.

​"What's wrong, honey?" I slipped up, and she shot me a sharp, dramatic look.

​I grinned as realization hit me: she was nervous about going out dressed like that. I shrugged it off. "Grab your purse, let's go."

​She whispered in a hushed voice, "Jack, I can't!"

​I laughed. "Come on, let's go."

​She looked annoyed, but I had a low-key plan in mind. We drove to Starbucks, and I ordered our usual coffees at the drive-thru. As we pulled up to the window, she looked incredibly tense, though she relaxed once we pulled away. By the time we turned back onto our street, she let out a visible sigh of relief.

​That's going to need some work, I thought to myself.

​"Well, did you enjoy your coffee break, Mrs. Brandson?" I asked as we walked up the stairs to the house. Like a gentleman, I let her go first—and the view was worth it.

​When we reached the door, she playfully punched my arm. "Yes, sir, I did enjoy the coffee."

​I smiled. "Well then, let's see what kind of trouble we can get into this afternoon."

​She laughed. "Oh yes, sir, that I think we can do."

​She walked into the office, set her coffee on the desk, and lifted herself up to sit on the edge. "Trouble, sir? I wonder what you had in mind."

​Admittedly at a loss, I said, "Well, what do you think would be a good task for you?"

​She hopped off the desk, letting her skirt ride up, walked to the door, and turned the lock. "Well, sir, one of my responsibilities, as I see it, is to ensure you don't go home stressed out. And I know today has been very stressful for you, so why don't you let me relax you a little before we close out the day?"

​I shrugged. "Let's see what you can do then."

​She commented, "Perfect. Why don't you sit in your chair, and I'll start with those big, broad shoulders?"

​I sat down, and she stepped behind me, seductively running her hands up and down my neck and shoulders. It felt incredible. She unbuttoned my shirt slightly, sliding her hands down my chest and back up to my neck.

​Stepping around to the front, she continued the massage while unbuttoning my shirt the rest of the way, spreading it open.

​"So, how is that feeling, sir?"

​I moaned softly. "Very good."

​She smiled, and as I closed my eyes, she continued, "I hoped you would enjoy this."

​She moved her hands down to my stomach and chest, tracing all along my torso. Then she slowly unbuckled my belt, unzipped my pants, and pulled them down, leaving me in my boxers. Her hands worked down my thighs to my knees, massaging the tension out of my muscles.

​Before I knew it, my shoes and pants were off completely. She spread my legs and slowly massaged her way up my thighs to my crotch, slipping my boxers off as well.

​"Now, there's what I wanted," she said in a low, seductive tone.

​I moaned as she pressed her chest against my legs and ran her tongue up my shaft, which was quickly growing hard.

​"I think I should take this off," she said.

​When I opened my eyes, her shirt and bra were off, her breasts resting against my thighs. "Oh, so much better," she murmured, returning her tongue to my shaft.

​Pausing, she asked, "Now, is this the kind of treatment you would like while at the office, sir?"

​As I moaned, she licked her way back down. "I can just imagine a hard-working man like you probably doesn't get much attention like this at home," she teased, my shaft throbbing in her hand. "But don't worry, sir, I am going to be here to ensure you are well cared for."

​She slid her tongue down to my testicles, circling them before moving lower to trace my taint, stopping just shy of my anus before working her way back up.

​"Did I hear you moan, sir? If I didn't know any better, I'd say you're thoroughly enjoying this," she said with a sly grin. Stroke by stroke, she added, "Don't worry, sir, discretion is the name of the game. Your wife won't find out how much I take care of things for you..." She licked up my shaft. "...like this big, thick cock of yours..." Then down to my balls, "...or these full testicles of yours."

​She took them into her mouth briefly before popping them out. "Oh no, she doesn't need to know about me taking care of these."

​She slid her tongue lower, swirling around my rim and making me gasp as she stroked my shaft. "Oh no, she will definitely not find out how I make you moan like that."

​She did it again, swirling her tongue while stroking me. "Yes, I think that will be our little secret."

​She shifted, bringing one hand down while positioning her mouth back over my head. She slid a finger inside me and began sucking my cock in rhythm.

​As her finger worked slowly in and out, she paused her suction just long enough to whisper, "Oh no, I don't think she'll care how well I drain your full balls before you go home."

​She went right back to sucking. My moans were louder than usual; the combination of her mouth and her finger was overwhelming, pulling me into pure sensation.

​When I finally came, it was to the steady rhythm of her hand sliding up and down and the firm pressure inside me. I released over her bare chest.

​"Now, you look so much more relaxed," she said with a smile as I slumped back in the chair.

​She slowly removed her finger, stood up, and walked into the bathroom to clean up. I sat there in pure bliss for a few moments before getting up to dress myself.

​When she reentered the office, she had a broad grin on her face. She walked around the desk and plopped right down into my lap.

​"Now, do you think we could make this position a permanent one, or would you still like to try other secretaries out before making a final decision, sir?"

​I hadn't realized she wanted to switch up the roleplay further, but if she wanted to explore other scenarios, I was curious to see where she'd take it.

​"Well, I think we could definitely interview a few more applicants, but Mrs. Brandson, you are definitely the front-runner at the moment."

​Her grin widened. "Well, that is to be expected, sir. And I'll take the liberty of setting..." She paused in thought for a moment before finishing, "...setting up more candidates for next week."

​I nodded, gave her rear a firm slap, and said, "You do that."

​She giggled, gave me one last lingering look, and slipped out of the office to get her day back on track.

​Later that night, after the kids were sound asleep and the house had settled into a quiet calm, Jennifer and I climbed into bed. The electric tension from the afternoon was still humming beneath the surface, but the rigid corporate boundaries of "Mr. and Mrs. Brandson" had softened back into the comfortable warmth of husband and wife.

​She slid under the covers, resting her head against my chest and tracing slow, idle circles over my ribs with her fingernails.

​"So, Jack," she murmured, a sly smile curving her lips in the dim light of the bedside lamp. "How did you enjoy your workday today?"

​I wrapped an arm around her, pulling her soft body tightly against mine. "Honestly? Best day at the office in years. I think my morale hit an all-time high."

​She chuckled softly, pressing a warm kiss to my collarbone before looking up at me, her eyes bright with genuine curiosity. "I'm glad to hear it. But as Office Manager, I need details for my records. What was your favorite part? And more importantly... what exactly are you looking for in these new 'applicants' coming in next week?"

​I looked down at her, catching the subtle spark of excitement in her eyes. She wasn't just playing along anymore; she was actively looking to push our boundaries and see how far we could take this dynamic.

​"Well," I said softly, running my fingers through her hair. "The secretary I had today set the bar remarkably high. The wardrobe policy, the... attentiveness to my stress levels... it was all incredible. But as for next week's candidates? That's completely up to you."

​"Up to me?" she asked, tilting her head.

​"Completely," I replied with a smirk. "You have total freedom, Jen. Whatever persona, outfit, or scenario you want to experiment with—whether she’s a shy temp on her first day, a strict executive, completely uninhibited, or anything else you've been curious to try—you run the office. I trust your judgment. Surprise me."

​Her smile widened into something delightfully wicked, full of endless potential as she rested her chin on my chest. "Total creative freedom, boss? Careful what you wish for, Jack. I might just get very creative with these interviews."

​"I'm counting on it," I whispered, pulling her up to meet my lips in a deep, lingering kiss.

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Written by Darkknight01
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