Office Mating - Prelude 04

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A smart intern learns the penalties of breaking the rules.
3.8k words
4.45
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Part 4 of the 6 part series

Updated 08/25/2023
Created 01/06/2023
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All night after I got home from work, and all during my morning jog, shower, and my commute to work, I replayed the incredible, scintillating sex Trent and I had the afternoon before, stretching the last bits of pleasure out as long as I could in my memory. I don't know what it is about him, but I knew I wanted more.

I arrived, logged into my workstation, and was soon able to push out thoughts of Trent and focus on the job. I was engrossed in my work at my cubicle at mid-morning when Trent's voice startled me.

"Show me," he said.

"AAH!" I shrieked. I had no idea he was standing there. I swung my head around to see him staring at me with the same unveiled hunger from the day before. "Don't sneak up on me like that!"

"Show me," he repeated, utterly calm, ignoring my complaint. I knew what he wanted me to do.

"People might see!" I hissed in protest.

"That's my concern. Don't make me ask again. Show me." His tone indicated he would tolerate no further talk. It was the same tone that made me wonder what would happen if I kept protesting.

I turned my chair toward him and, while staring into his eyes, slowly and deliberately pulled my skirt to show him a very sexy pair of thong Victoria's Secret panties, which I had picked just for him that morning. My obedience to him completely overcame my sense of fear and shame.

"No stockings today," he observed. He paused. I began to become nervous as time ticked away, my panties on display to anyone who walked by.

"Give me those," he pointed to my crotch. I glanced around, raised my ass off the chair, shinnied out of my panties, then handed them to him. He brought them to his nose while looking me in the eyes. He closed his eyes, inhaled, then looked directly at me again.

"Remember that I tasked you to anticipate what I need and want at any given moment," he stated. "My needs and wants happen throughout the day, and you need to be ready. I know there are times that you cannot be ready for me. You will tell me in advance about these moments." I nodded, as I had heard this yesterday.

He folded my panties and tucked them into the breast pocket of his suit jacket.

"We will be eating lunch at my office today," he stated.

I had lunch plans with one of the other interns. We planned to hit a bar together and gossip. "Actually, I was going to have lunch wi--"

"You're eating with me today." he said, matter-of-factly. The hunger in his eyes briefly tinged with anger.

"I will make some calls," I conceded.

***

Two hours later, I was standing in the doorway to Trent's office, waiting for him to finish a telephone call. When he saw me there, he waved me in and pointed at the floor next to his desk. I listened to his call as I walked to where he pointed.

"Yes. I have told you exactly what I want done... You know I don't care how you do it... Yeah, just be sure you get it done on time... That's fine, yes... Look, I have a personnel discipline issue that I need to work on. We will check in about this on Monday." He listened for a few more seconds, then said, "Yeah, right now. Talk Monday. Yeah. Bye." He hung up the phone, then pushed the "do not disturb" button.

He looked up at me. The hunger was there, but so was something slightly sinister: frustration? anger? I figured it was about his phone call. He kept looking at me for several seconds. I became self-conscious.

"Stand still," he ordered. I suddenly became aware that I had been fidgeting in place. I planted both feet on the floor and folded my hands in front of me. I kept standing under his gaze, becoming ever more insecure. It dawned on me that I was likely the "personnel discipline" he was talking about, though I had absolutely no idea what I had done.

Trent leaned down and opened the bottom drawer of his desk. He produced a white gift box from a high-end ladies' boutique, which he placed on his desk.

"Open that."

I reached out with a slightly trembling hand and picked up the box. "La Perla" was embossed on the front. Inside was a garter belt and three pairs of new stockings in different colors.

"You will no longer wear slacks or pantsuits at work, nor will you have bare legs or wear pantyhose. You will wear only skirts with stockings to work. This is now part of your dress code. Do you understand?"

I nodded.

"Is that a 'yes'?"

"Yes."

"Explain in your own words what I just said." This seemed like such a simple rule. Why was he quizzing me like a child?

"I can only wear skirts, no pants, and that probably means no jumpsuits, either." He nodded in confirmation. I continued. "And only stockings and garters under my... uh..." as the words came out, I remembered something Trent said this morning at my desk. "... my uh... skirt." My voice went down an octave and was barely audible as I finished: "And no panties or other undergarments except during my period." I blushed as I these last words came out of my mouth.

"Yes. Correct. I am glad you and I communicate so well." I felt relieved and even a little proud. I stood in place, staring at him for an awkward moment.

He raised his eyebrows, nodded at the box, and said, "Now."

I glanced at his open office door, then at him, then back at the door. I took a step toward the door to close it.

"Stop," Trent intervened. I froze one step away from the desk. "You have been instructed about the dress code and instructed to comply. Stand where I told you and Finish. Getting. Dressed." There was an edge in his voice as he said the last three words. I knew for certain the disciplinary problem was me.

I stepped back to my spot next to Trent's desk. It was unlikely anyone would visit during lunch, but the very thought that a coworker would see me if they walked into Trent's office caused me nearly paralytic fear. I hesitated, box in my hands, office door wide open, heart rate elevated, breathing shallow. My mind was a tangled mess of thoughts and motivations that was all being poached in steaming pot of my own arousal.

Trent stood from his chair. He took the gift box from my hands, put it on his desk, then sat on the edge immediately before me. Our bodies were a foot apart, and I could feel his heat in my tits, abdomen, and pussy.

"What is your role on our team?" he asked.

"To anticipate your needs and wants, and to fulfill them." I said with confidence.

He reached up to my cheek and touched it gingerly with his fingers. Heat radiated from his fingers into my cheek, across my face, then down through my neck. I closed my eyes and tilted my head down. He grasped my chin gently and pointed my face back at him. I opened my eyes to find I was staring directly into his.

Holding my gaze, he continued our conversation. "What do you do if I give you an instruction?" He released my chin and let his fingers trace their way down so that his thumb and fingers were gently brushing opposite sides of my neck.

"I obey." I breathed, my arousal building.

"When do I expect you to obey my instructions?" he asked, as his hand traced its way over my clothed breast.

"Immediately," I whispered as my nipple responded through my bra. Arousal changed to lust.

"After I give you an instruction, what else should you be worried about?" he said, his hand sweeping over my waist to my hip then around to my ass.

Trent must never say anything that does not have meaning, and this morning's conversation was no exception.

"Nothing. Everything else is your concern." My voice was ragged. Lust changed to ache. I knew right then that I would again do anything Trent wanted.

"Very smart," he said. The compliment had me breathless. I felt him move his hand from my ass to grasp my hand. He directed it to the waist of my skirt. "So, what do you do now?"

I looked into his eyes and bit my lower lip, wanton with need. He sat back in his chair, then re-established eye contact.

I held his gaze as I pulled each of my heels off, then reached around my back, unzipped my skirt, and let it fall to the floor. The tails of my blouse mostly covered my naked pussy and ass, but I was very aware of the open door and the cool, air-conditioned breeze across my naked pussy.

I reached into the box and grabbed the garter belt. I lifted the tails of my shirt and camisole and held them against my chest with my chin. I wrapped the garter belt around my waist, fastened the hooks, moved the closure around to the back, and released my shirttails. I chose the nude-colored stockings from the box and gathered one stocking from welt to toe. I lifted my right foot and slid it into the stocking, being careful to get the heel and toe straight. I put my foot onto the edge of the desk and eased the stocking over my calf, knee, and thigh, working slowly so I didn't damage the material. I fastened the suspender in front and put my foot on the floor before fastening the suspender in the back.

I did the same with the other foot, moving equally slowly. Trent watched every small movement. My vulnerability and compliance, combined with his burning gaze, made my heart race. My desire for Trent screamed out for release.

I checked for gathers and twists, and then adjusted the suspender straps to make sure everything stayed put. I picked my skirt up from the floor, oriented the zipper to the back, then slipped it over my head and down to my waist, making sure my blouse was neatly tucked in. I zipped up, slipped my feet back into my heels, then waited for more instructions.

Trent stood, strode across the office, and closed the door. He returned only to stand so close behind me that I could feel his breath on my neck. He reached around to the front of my skirt and grasped the hem with one hand. He pulled it up high enough to get his other hand under the skirt, where I felt his fingers glide deeply into my damp folds. As he massaged my pussy, his other hand moved up to grab my left breast. I groaned, aglow with pleasure, and leaned into him. My swoon had the opposite result of what I hoped for. He withdrew both hands, placed them on my hips, and said,

"You're aroused. Do you think you deserve pleasure?"

I had never heard the word "deserve" in a conversation about sex. In all my sexual encounters, I wanted it, my partner wanted it, and we fucked. There was no discussion about worthiness.

Confused by his statement, I tried to respond "I don't know. I..."

He shoved me forward, bent me over his desk, and pinned my chest down with his left hand. "Do you know why I have you in this position?" he asked. I was certain we would have a replay of the day before, so I answered his question by wiggling my ass back and forth against his groin with a smile on my face.

Feeling me rub against him, he sidestepped around to my left. "You wanton slut. Pull up your skirt so I can show you why you're here."

I could not reach my hem so I had to improvise. Still smiling, I reached down both hips and used my fingers to inch up my skirt a little at a time. Just as I got it high enough where I was sure he would fuck me...

SMACK! His hand came down on my ass, then stayed there grasping my right ass cheek, opposite where he stood. The spank was not painful, and in retrospect I am certain he held back and just wanted my attention. Nevertheless, I was wide-eyed in shock: not even my parents had spanked me before. It was clear this was not going to be another session of hot animalistic fucking.

He then spoke with a dispassionate and measured voice.

"You are a member of *my* team. I expect you to follow *my* directions. There are consequences for your failure to follow them. Today, you have earned eight spanks. I am going to explain exactly how you earned your punishment, just so we are clear.

"You earned one spank for failing to anticipate that I want you to wear stockings every day. This should have been obvious after our meeting yesterday.

"Second, you earned one for wearing panties. This means you were not 100% prepared to meet my wants and needs. You should have picked this up from our meeting yesterday.

"You earned three more this morning, one for each time you talked back to me after I gave you an instruction.

"During our current meeting, you earned a sixth spank for attempting to close the door without first hearing an instruction from me.

"Then you earned two more when you failed to act after being instructed about the terms of your dress code, even after I gave you the resources to comply."

"However, I am deducting two spanks from today's punishment, one each to your thoughtful answers to my questions about the dress code and the boundaries of your concerns."

I am certain I would have been mortified hearing this if I wasn't so damn turned on. Instead, I figured he would give me five more spanks like the first, and we would move on to sex

"Do you understand that you will be punished?" His question seemed so ordinary, like this was part of his management philosophy with all his employees.

"I understand." I wanted my compliance to be clear.

"Do you understand why you're being punished?" he followed.

"Yes. I understand why."

"You can choose not to participate in this discipline. If you do, just say 'stop' or 'red' and we will immediately stop. After that you will go back to your work, and we will never do any of this again. Do you understand everything I have said?"

"I understand every word." I said, trying to show Trent I was not afraid of him.

"What do you say if you want me to stop?"

"'Stop' or 'red'."

"Are you telling me to stop now?"

The rational part of me screamed out in my head, "Of course I am telling you to stop! He is about to spank me like a petulant child. He is my boss. I am not just a subordinate, but an intern, for god's sake! This violates every policy in the employee handbook, and about a dozen state and federal laws! I could have Trent's job for this!"

"No." I said, silencing my rational self.

"There will be a total of six spanks, and we are starting at two. You will count out loud. If you do not state the number out loud, I will repeat the spank until you do. Got it?" Trent's instructions were, again, clear.

"I understand."

Trent tightened his grip on blouse and pushed my chest harder into his desk. He released my ass with his other hand. I tensed in anticipation.

CRACK! I was surprised that the second spank was so clearly harder than the first. It landed in the same spot. I could feel the sting, and his hand stayed put for a moment.

"Two!" I said with as much confidence as I could muster.

His hand lingered firmly on my ass, then disappeared. He waited an agonizing extra second.

SLAP!

"THREE!" I immediately croaked out. This one landed in the same spot as the first two. The sting turned to intense, painful prickles, and a deep warmth spread across my ass cheek.

His hand disappeared again. I knew it was com--

SMACK!

Holy shit that came fast and I didn't even have the chance to flex my butt! This one landed on the opposite cheek, but lower down. When his hand hit my ass, his fingers wrapped between my cleft, making contact with my pussy. As before, he massaged and grasped me there, making slight contact with my sex. As he took his hand away, he dipped his fingers into my folds from my clit to my asshole. I was completely at his mercy. Despite taking this punishment, despite the pain, and despite the humiliation, I was more turned on than I was the when he pinned me to the desk.

WHACK!

This was at the top of my left thigh and this time he made more deliberate contact with my pussy. The contact felt like a shock through my clit. My ass felt like it was glowing bright orange-red light. "HUHHhhh!! FOUR!" I croaked.

Trent took a moment and massaged my ass. This did not make things feel less painful; instead, the heat became hotter, and the prickling became thousands of needles in my skin. Somehow, all this completely inflamed my clit, pussy, and asshole. I felt my pussy lips slide across each other obscenely as he massaged me. I was shocked to realize that I felt an orgasm coming.

Trent kept massaging me from my ass down to my pussy lips. He rubbed his fingers deeper into my now-soaked folds, then used the lubricant to massage my clit directly, bringing my approaching climax to the center of my attention. I writhed under his hands. I could tell that I would come if he just kept going for a few more sec--

His hand disappeared and immediately came back with a CRACK!! This was the hardest blow yet. "FIVE!!" I groaned out, my voice breaking. My climax was still right at the doorway of my mind. I no longer felt pain from the spanking I was getting, as the sensations of each stroke had melded into a dizzying mix of lust, pain, and pleasure. Trent ran his hand and fingers from my tailbone across my asshole, and back into my dripping pussy. He massaged me, bringing me closer and closer to climax. I was inches--seconds--away.

Twisting again under his hands, I heard my own voice. "Please..."

Trent withdrew his hand from my pussy and placed it on the small of my back. "Please what?" he inquired.

"Please... Please..." I arched my back to thrust my ass in the air, trying to move his hand back to my sex. My pussy and thighs were slick. Trent's hand had spread my fluid across my asshole and cheeks. I was incandescent with sexual arousal, seconds from coming, but yet, amid all this, Trent was instructing me to explain myself.

"Please. What." Trent repeated sternly.

"Please, just make me come. I need it so bad. Oh god please!" I begged shamelessly.

"No. You have not finished your punishment yet. You have one more to go."

I had not noticed during this dialogue that his hand had vanished from the small of my back.

CRACKKK!!! His final strike landed right at the fold of my left ass cheek. His fingers struck my open pussy and drenched clit. The pain coursed through my ass and pussy like lightning.

I shouted "SIX!" As an orgasm exploded through me. Trent insinuated his fingers deeply into my gushing pussy. I bucked and squirmed on his desk, my anus and pussy pulsing, and my mouth stretched open as I let out a long, loud, grunt.

"SHUSH!" Trent commanded in a loud whisper. He moved his other hand from my shoulder blades and pushed my face into his desk, pinning my cheek against his blotter. His fingers were deep in my mouth. "UUUHHHHGGGHHHH!!!" was all I could say around his fingers as I spasmed and shuddered on the desk for what seemed like minutes.

My orgasm faded while I was pinned to the desk like that, fingers of one hand in my mouth, fingers of the other hand in my pussy. When the spasms subsided, I took a deep breath, let it out, and went limp. I lay on the desk like that for a minute before Trent removed his hands. I stayed there another few minutes before I stood. I pushed my skirt back down in the fringes of consciousness. I was sure my makeup and hair were disastrous.

Trent gently grasped my arm and walked me around his desk, sitting me on the edge facing him. The edge of the desk made me wince, but I could not think to move. He gently took an escaped tendril of my hair and tucked it back behind my ear. He stroked my face, wiping something off my cheek: spit? lipstick?

He then sat in his chair, so his head was about even with my chest. He adjusted my skirt so it was straight, then smoothed the wrinkles as best as he could. He re-tucked my blouse into my skirt. He then reached up to me and guided me into his lap.

I put my face on his shoulder and curled into a ball. He held me gently, stroking my back, cheek, and hair. We sat like that for what felt like ten more minutes.

Trent spoke quietly. "It is time to get back to work. But before you go, I wanted to tell you that sometimes our meetings go late. You should make sure you have enough makeup and toiletries to do your hair and makeup here at work. Like an overnight case or something. I would be happy to reimburse you for the costs."

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