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Author's Notes

"Thank you for all the love for our series. It's been fun to see how people relate/react to different characters - some more favorably than others, just like real life. Like all stories in this series, the main characters are based on real people, using their real names. <p> [ADVERT] </p>Each story can be read by itself, but hope you'll enjoy the others. This is the first in a trilogy. The second will post tomorrow. Grateful to Koo who came up with the concept for this trilogy."

“Damn, you’re hot,” I said out loud, complimenting myself as I looked in the mirror. It wasn’t just how I looked, although I couldn’t deny that. It was true in just about every aspect of my life. I finally broke through the glass ceiling at the bank where I had worked for twenty years. I worked hard and did whatever was necessary to climb from being a teller to vice president. Six months ago, I married my third husband, a man who loves me for who I am and lets me live my life. My three daughters are all in their 20’s and early 30’s, living on their own. I am financially secure. The promotion meant my savings and investments were piling up faster than I ever thought possible. I am fit and work hard at taking care of myself. My body rivals the bodies of my athletic daughters.  

I smiled admiringly at myself in the mirror as I ran my petite hands down the front of my new pink custom-tailored suit from Neiman Marcus. It was a splurge, but worthy of a bank vice president. Images online showed the small tight-fitting blazer without a top, showing off her cleavage. Unfortunately, the bank wouldn’t allow that, although my firm 34C tits would pull it off. Instead, I decided to wear a sheer white top with the buttons open as low as I could get away with while still maintaining the bank’s professional requirements. The blouse was see-through enough to require a bra. I decided on beige that covered only what was necessary, allowing the low opening and semi-transparent fabric to show off my cleavage.  The pencil skirt was tight-fitting and stopped three inches above my knees to accentuate my perfect small round ass. My matching four-inch pumps raised my height to a sexy 5’6” to finish the look I wanted. My long brunette hair cascaded over my shoulders with a light curl, showing off my hazel eyes and tan skin.

Yes, I’m hot and honestly a little cocky about it. I didn’t get here by accident. I have faced personal and professional challenges along the way and have done whatever was necessary to rise above them. I’m good at what I do and know exactly how to use everything I have to get what I want. My willingness to go the extra mile has been acknowledged by my bosses publicly and behind closed doors. In this competitive line of work, favors are rewarded and advancement is earned.

Now it’s my turn. As a new vice president, I watch for young highly-motivated employees, especially if I find them desirably handsome like Jefferson. It started when I first saw him take a second look and watch me longer than a typical employee should ogle their boss as she walks by. A woman knows when a man is undressing her with his eyes. The look on his face when I first caught him told me everything.

I started grooming him subtly with simple work assignments that became more personal. I rewarded extra effort on the job with small bonuses or letters of recognition in his employee file. At the same time, I watched how he responded to the glimpses of my cleavage and ass I offered inconspicuously.  I observed how he looked at me when he sat in the chair in my office as I stood and leaned against my desk in front of him. He was glad for the chances, showing his eagerness to do whatever it takes to advance his career.

The opportunity to take a personal interest in Jefferson’s professional career for my own pleasure is a perk I have in my job. How do I know? I learned from the best. I was mentored by high-powered bosses who offered me personalized opportunities for advancement. Each opportunity required more from me, and each time I made sure I exceeded their wildest expectations. I am not ashamed of using what I have to achieve success. Everybody does.  I learned well. Now it is my turn.

Jefferson’s new personalized executive mentoring and advancement track began during an annual employee evaluation I purposely scheduled on a Friday afternoon at 4:30. I took my bra off, but kept my blazer on to begin. Beneath the skirt was only an already-soaked tiny black thong.

Jefferson came into the review wearing a standard blue sports coat, white dress shirt, tie, and gray pants. Jefferson was just over six feet tall, muscular, with brown hair and blue eyes that accentuate his rugged square jawline. I knew from his file that he was twenty-five.

“Please sit down,” I said, pointing to the brown leather chair in front of my large executive desk. I sensed some nervousness on his part, like most employees coming into an annual evaluation, fearful of something unexpected.  I remained behind my desk for the evaluation. I took my time going through the usual process, to ensure our discussion of the final section took place well past the hour. As usual, the office emptied by 5:00 on a Friday, especially the senior management offices upstairs. 

“Before we discuss the final portion for this next year, any questions about your evaluation so far?” I asked.

“No,” he answered. “This has been amazing. I like working for you. I appreciate your kind words and confidence in me. You’re a mentor to me.”

“You’re welcome,” I answered. “It is well deserved, Jefferson. I want you to know your hard work to please me hasn’t gone unnoticed.”

“Thanks, Boss,” he said.

“Or unrewarded,” I said, with a slight smile. “Before we talk about your new goals, duties, and compensation for this next year, would you please close my office door? We don’t want others jealous of what I want to offer you.”

Jefferson’s eyes widened with immediate exhilaration. “Uh, sure,” he said, jumping up to eagerly oblige. He walked across the large office and closed the door. It was unnecessary since we were the only two people left on the executive floor, but an important preparation for what I had planned. I had preset the handle to lock when the door was closed, further ensuring we would not be interrupted.  Jefferson returned to his chair, excited that his evaluation was going better than he imagined. He looked up at me from across the desk, with suspense-filled anticipation.

I stood up and started to walk around my large desk. “Do you mind if I take my coat off?” I asked, feigning permission.

“Uh, no. I mean, it’s your office,” he answered.

“That’s right,” I said, smiling as I slipped the coat over each shoulder, letting it fall into my hands. I laid it on my desk as I continued around the desk, until in front of it. I leaned my ass against the desk, taking hold of its edge with both hands on either side of me. As I did, my short hem hiked up, stopping just below my pussy. My bare, tan legs stretched out directly in front of him, with my four-inch heels planted an inch from his shoes.  I leaned forward slightly, in a natural position, yet offering an ample view of my cleavage from the low-cut sheer blouse. My stiff nipples showed off impressively through the thin, sheer fabric.

Jefferson gasped audibly. His eyes unavoidably glued to my tits before nervously darting around. He was uncomfortable and unsure where he should look, with his boss positioned seductively in front of him. I was certain I saw movement in his lap.

“As I’ve made clear, I like you, Jefferson. I believe you have great potential. I’ve decided I want to help you get to places you’ve only dreamed of as others have done for me.”

“Thank you, so much Pam,” he replied. “That means a lot.” He did his best to keep his focus on my eyes.

“That’s the way this business works. I am going to make you an offer I’ve never made to anyone else. If you accept it, it is guaranteed, but off-the-books. It is also a one-time, take-it-or-leave-it opportunity.” I paused to watch his face for a response.

“Okay,” he said, with a look of excited curiosity.

“If you decide not to take it, there will be no hard feelings or repercussions. It will never be mentioned or offered again. Whether you accept it or not, you must first promise that you will not mention a word of this conversation or its outcome to anyone.”

“Wow. Okay. I promise. Just between you and me. I appreciate your trust. This sounds serious.”

“It’s more serious if you accept it,” I replied with a smile. The air in the office thickened with suspense. “If you accept, I will personally and actively work to fast-track your advancement here. That means promotions, responsibilities, perks, and compensation packages that will come far faster than usually happens, or is allowed.”

“Wow, Pam! You’d do that for me?”

“I would, gladly,” I answered. “It would be earned and deserved.”

“I’m glad for any opportunity you want to give me. I’m a fast learner. Why would I not accept that?”

“Good question. The only possible reason is that it will require your commitment to do anything and everything I ask, no matter what. No hesitations. No limitations.”

“How is this different from what I’m doing now?”

I put my foot up on the seat of his chair, exposing the inside of my leg and pussy to him. “Anything. Anywhere, Any time,” I answered with gentle firmness in my voice. The ends of my mouth rose, to offer a small smile.

“Oh shit,” he replied, stunned. His face showed a mix of emotions. “You’re serious.”

“As serious as your dick is hard. I’ve seen the ways you’ve looked at me, Jefferson. Am I right?”

Jefferson blushed awkwardly, embarrassed. He glanced quickly at his lap, confirming the movement of his thickening cock.

I smiled, self-satisfied with how this was going. I had seen his passing lustful looks since he started. This was the first time I was in a position to see his cock responding to the fantasy of being fucked by his boss.

“One-time offer Jefferson. You say ‘no,’ and this conversation never happened. You can walk out that door, and nothing changes. You say ‘yes,’ your career rockets with the added responsibility of becoming my little work fuck toy, among other things. This is of your own free will and consent. Think carefully about your response. This will be binding. There is no backing out as long as you work for me.”

Jefferson looked lustfully at me, focusing on my tits and visible black thong. He took a risk and softly caressed the top of my leg as if testing the softness of my skin.

“Ah, ah, no touching,” I ordered. I picked his large hand off my leg and threw it down. “There is only one way that happens, and this is the only opportunity you’ll have. This offer is time-sensitive. You have one minute before the offer is rescinded,” I said, using my best negotiation tone. I glanced up at the clock on the wall, pulled my foot down from his chair, and leaned back again against the front of my desk. I crisscrossed my arms across my chest.

Jefferson pondered, taking his time to look up and down my body as he considered the offer, cost, and risk.

“Ten seconds,” I counted, as the second hand approached the starting point. “Nine, eight, seven, six.”

“Yes,” he said, looking up. “I accept.”

I smiled as I stood up in front of him. It was now my turn to assess the prize. I ran my finger through his hair, and down his chest. “You promise your complete submission. Anything I ask. No limits.” My petite hand continued down and took hold of his crotch.

“Yes. I will do anything you require without limits,” he repeated, in a tone, as if aroused himself by the offer.

“Very good. We start now, then,” I said. “Effective immediately, you will see an increase in your salary. As a salaried employee, your compensation is not based on 'banking hours' but on completing your job – whenever and however necessary. Your job title, for now, will remain the same, including many of your usual tasks. That will be important to not draw unwanted attention.”

“Understood,” he said.

“What also changes, is the primary purpose of your employment. Your job now is to please me in any way I require. Over time, other people may start to see you as a kiss-ass. Let them. That’s one of the many things you’ll be doing.”

I turned around, with my back to him. I bent over slightly, keeping my legs straight while bracing myself with my hands on the large mahogany desk. “Remove my panties and show me what your fingers are capable of.

His strong hands lifted my skirt over my ass, reached up, and pulled my panties down. Memories flooded back of times over the years when I was asked to undress a supervisor after making similar promises as Jefferson.

Jefferson moved to my side, cupping my ass with one hand, while the other moved around front to begin caressing my folds.

I moaned at the feel of what I imagined for weeks, anticipating this moment. His fingers moved softly up and down the length of my soft labia before rising to stimulate my clit.

“Mmm, yes, Jefferson. That’s it. “My whole pussy, then my clit.”

Jefferson obeyed, repeating the pattern. He masterfully stroked my soft feminine lips with his fingers, then used his thumb on my button. The first of the many orgasms I would get from him quickly started to rise.

“Finger me! Finger me, now,” I ordered. My bared ass gyrated from the growing intensity. “Oh, fuck yes!” I said, at the feel of his large middle finger sliding into me.

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Jefferson fucked me with it before adding his ring finger, bending them both to find my g-spot. He slid the tip of his fingers back and forth across the sensitive surface while returning his thumb to circle my clit.

“Oh, yes! Go back to fucking me with your fingers.”

He obliged, starting slowly before gradually moving faster.

“Stroke inside again,” I insisted. I continued to instruct him on what I wanted until my pussy was drenched. The climax loomed large.

“Get your cock out and work it in me,” I demanded. I sensed his surprise, assuming I would have reciprocated by pleasuring him. As much as I like him and his work, our new arrangement isn’t for him to become my lover. He is my fuck toy. His cock belongs to me, for my pleasure. Any gratification he receives is a bonus for him, but not my responsibility.

I heard the sound of his pants opening before I felt his skin pressing against me from behind. I pushed my ass back. His cock moved across my tender folds before his unexpectedly thick head pushed into my tight, soaked pussy.

“Fuck, yes,” I said, pleased at my first feel of him inside me. “Push in deep and hold it there, Jefferson.”

We both moaned with pleasure as he did. I hadn’t anticipated how deep the penetration would be. God, it felt good.

“Pull out slowly, all but the very tip of your cock, then thrust hard back into me.”

He responded immediately, as he always does with his work. His movement was slow, measured, and glorious.

I gasped. “Yes,” I affirmed. “Now repeat that,” I instructed, maintaining control and telling him exactly what I wanted. “Pull out slowly, then thrust in again.”

He obliged, following my instructions perfectly. My first orgasm grew like a giant wave, getting bigger and bigger, in anticipation of a thundering crash. The arousal was a combination of his cock in me and the new aphrodisiac I had only dreamed of, using him as my new toy.

“Oh, shit! I’m going to cum! Keep going, Jefferson. Pull back slowly and pound my pussy. Again!” The giant wave rose like a tsunami before finally crashing. The intensity rolled into a sustained climax.  My head dropped to the hard, flat surface. My hands clenched on the desk as if trying to grab something to stabilize myself from the unrelenting force. My body quaked. Jefferson dutifully continued, prolonging my pleasure.

I turned around to face him. He leaned in to kiss me. I turned my head to deflect his attempt while taking his thick cock in my petite hand. It was my first look at it. I could tell he felt rejected, but that wasn’t my problem. I liked him a lot as a person and employee, or I wouldn’t have offered this opportunity for career advancement. But his desires were not part of our arrangement. Instead, I felt an immediate sense of self-satisfaction for my accomplishment. It was enough for him to agree to my proposal and to begin his new duties so well. It was an added bonus to get a first look at his cock, and another reason to be impressed by my star employee.

I leaned back against my desk again and straightened my legs. “Kneel down and lick my pussy,” I said, in a direct tone as if asking him to bring me coffee or run some numbers on a project.

Jefferson smiled at the order. “Fuck, yes!” He took his coat off and loosened his tie, showing his confidence. His pants were already around his ankles, from the previous fucking.

“Nice and slow to start,” I instructed. I watched his tongue emerge, press in at my opening, before slowly rising toward my clit. My wet pussy still glistened from the huge climax. He looked up at me, as if for approval. “Yes, just like that, Jefferson. Keep going, just like that.”

I was pleased by how quickly my arousal grew again, almost as if he was bringing the first one to new life. “Fuck yes. Now a little faster,” I said.

Jefferson obeyed, feasting on the taste and pleasures of his boss.

“Lick my clit,” I said.

Jefferson moved his tongue up to my raised clit. It stood tall, as if demanding attention from the servant's tongue. Jefferson smiled, as his tongue claimed it.

“Oh fuck!” I said, at the flick of my clit. “Circle it.”

His tongue obliged.

“That’s it,” said, enjoying the escalation of the next climax as it approached. “Now down the length. That’s it.” Every several seconds I gave him another direction. “Yes, again. Keep going. Now my clit again. Circle it. That’s it. Oh, yes. Now massage it with your whole tongue. Yes. Oh, fuck yes!”

My body trembled as the next coaxed wave approached, almost as strong as the first.

He reached up and took both ass cheeks in his hands, pulling my pussy toward him. His face became soaked as he pressed in against my soft folds.

“Spread my lips with your fingers,” I ordered. Jefferson did as he was told. “Suck my clit in.”

My back arched as he did. He feverishly licked my button, as he held my captive clit with his lips. “Oh fuck!” I screamed. “Lick it all. Lick it all, now!”

Jefferson released my clit from his lips and stroked the length of my soaked pussy with his tongue.

“Oh god, faster. Faster, Jefferson. Yes. Yes, that’s it. Harder! Yes! Yes! Yes!”

My body suddenly convulsed in front of him as he gripped my ass again to hold me in place. His face buried itself in my drenched pussy. His tongue worked zealously to exceed my already high expectations.

“Oh fuck, yes!” I squealed, in euphoric pleasure. “Don’t stop, Jefferson. Don’t you dare, fucking stop!”

Jefferson persisted, following my order. It was evident he was also enjoying himself. He clearly relished eating pussy, something I took note of for his future assignments. I smiled at the image of him in the future, crammed under my desk, eating me out as I worked. I had been there myself. Now it would be his turn. The thought heightened my current arousal, taking me over the edge.

My pussy gushed in his face. I pushed my fingers through his hair, taking hold of his head with both hands, and pulled him in tighter. “Yes! Keep going! Faster. Harder! Yes! Fuck, yes!” The orgasm rocked me. I was dizzy from the pleasure. After sustained pleasure, I pushed his head back.

I breathed hard and worked to catch my breath. I was pleased with his performance, but not quite done.

“Stand up and fuck me,” I said, offering a smile. “Would you like that?”

“Yes,” he said, truthfully. “I’ve thought about it many times.” He removed my top and skirt. His semi-hard cock rose to the occasion with a few of his own strokes, as I laid back on my desk. My nipples were as stiff and tall as thimbles.

“Fuck me, Jefferson.”

Jefferson kicked off his shoes and stepped out of his pants. He pressed in between my legs, pushing the bulbous head of his long, thick cock into my drenched pussy.

“Nice and slow,” I instructed. “Bring me up again.”

Jefferson masterfully used his tool, filling me with his entire length.

“Yes, that’s it,” I said, pleased with myself, and my new acquisition. My pussy’s pleasure reemerged. “Oh yes, that’s it. Pull it out and run it over my clit.”

Jefferson did so, with a moan of pleasure for himself.

“Now fuck me again, this time a little faster.”

Jefferson obliged. His beautiful cock disappeared into my wanting pussy.

“Back and forth now. Keep that pace.”

He continued, enjoying the experience.

“Rub my clit with your fingers. That’s it. A little faster. Fuck, yes. That’s it. Faster now. It’s coming! Faster with my clit, Jefferson! Fuck me harder! Yes. Yes. Yes!”

I looked up and could see Jefferson’s own arousal on his face, growing with mine. Light sweat appeared on his body. He gripped me tighter as he fucked me harder.

“Oh shit! I’m going to cum again,” I announced.

My words only aroused him more. “Fuck, yes!” he whispered. “Yes, yes.” His breathing quickened.

“Don’t you cum yet,” I ordered.

“I’m so close!”

“Don’t you dare cum without my permission. Understand?”

“Oh, god. Yes, Pam. I’m so close.”

“Fuck me harder, Jefferson, but don’t you dare cum yet.”

Jefferson’s face showed the aching challenge of the impossible order. “Oh shit!” he yelled. His muscles bulged, using everything in him to obey my order not to cum.

My new orgasm power over him heightened my own arousal. “Yes, harder,” I said. “You’re going make me cum again.”

My back arched as his muscular body slammed into me. I gasped loudly as the climax consumed my entire body, stretched out on my desk. “Don’t stop, Jefferson! Fuck me!”

He savored the opportunity to fuck me. His face contorted, doing everything in his power to obey my simultaneous commands to keep fucking his boss, while not cumming.

“Please, may I cum?” he begged, in agony.

“No,” I answered, denying what he was desperate for. My climax finally quelled, making my pussy ultra-sensitive after the multiple orgasms.

“Now, Pam? Can I cum?”

I pulled back from him, sliding further back on my desk. His giant red cock throbbed, still covered in my cum. The desperation of my new twenty-five-year-old work slut was obvious. This was an important moment to define our new work relationship. I was not there for his pleasure. He was here for mine.

“Oh fuck, please. Please, Pam, don’t leave me like this.” His cock throbbed as if bowing and joining in the desperate pleading.

“So, I make you want to cum?” I asked.

Jefferson blushed. “Since my first day,” he confessed. “Please, can I cum? I’m so close.”

“You’ve fantasized about me?”

Jefferson nodded.

“Masturbated?”

Jefferson’s blush answered the question.

“Show me,” I said. I slid off my desk and returned to my chair. “I have a trash can over here. Show me how I make you cum.”

“In the trash can?” he asked, disappointed, as he walked around to the back of the desk. He stood by the trash can, positioning himself inches from me, hoping, one way or another, I would finish him.

“I’m going home to my husband. I have plans tonight, Jefferson. There’s no way I’m going to let you cum in or on me, but I’ll let you cum for me. Stroke yourself and show me what happens when you think of me.”

Jefferson positioned himself on the other side of the small trash can, facing me, wearing only his white shirt, partially unbuttoned, and loosened tie. His dick still throbbed in desperation. His large hand took hold of his familiar cock, with long slow strokes. His gaze lowered to his naked boss in her executive chair, wearing only heels. His mind fucked me through his eyes, while his strong hand fucked his cock.

I leaned back in my chair, unconsciously fingering my pussy at the sight of him jerking off to me. This time it wasn’t using pictures in his mind or imagination. My spent, naked body was on full display right in front of him.

“Oh fuck,” he said, as the climax grew stronger. His cock was red and his balls swollen. “Oh shit! Shit!” Each time he cried out, his voice got louder with the approaching orgasm.

I smiled gratified, watching him so aroused at the sight of me. I moaned, knowing full well it would add to his arousal. “Look at that beautiful, desperate cock,” I said out loud. “Show me, Jefferson. Show me what I do to you.”

“Oh, fuck!” he yelled. “I’m going to cum hard! Shit! I’m going to cum! Fuck!”

“Show me,” I teased in a sultry voice. “Every drop in the trash can. Don’t stop. Cum for me.”

Jefferson’s mouth opened. He let out a small scream that grew to a loud roar as thick cum flooded from him. He immediately dropped to his knees in front of the can, and me. He aimed his cock down into the small, lined, wood trash can. He looked up at me, splayed out in front of him, as he gripped harder and stroked faster. With every stroke, his moans got louder, and became more overwhelmed by the thundering climax. He finally came to a stop with a large gasp, emptied.

I smiled as I watched him finish his tribute to me, his boss. “Very nice,” I said affirmingly. “So, how did you like your review today?”

Jefferson laughed. “Best ever, Boss.”

I stood up and walked over to him. I traced my finger down the length of his semi-hard cock, my index finger picking up a small amount of cum as it crossed the surface of his sensitive head. I licked my finger with a sultry smile as I continued to walk around to the front of my desk. I picked up his boxers and wiped my wet pussy dry before dropping them on his pants. I pulled my own panties on. As we both got dressed, I reiterated the binding terms of our new agreement.

“Any further questions?” I asked.

“No,” he said. “Shall I go?”

“Yes,” I said. “Nice work today. See you Monday.”

Jefferson offered a genuine smile, before turning and walking toward the door.

“Aren’t you forgetting something?” I asked.

Jefferson stopped and looked around, confused. “Forgetting something?”

“The trash can liner,” I said. “I don’t need my trash can filled with your cum.”

“Of course,” he said. He awkwardly walked back, picked up the liner, and carried it out as a souvenir he never imagined. We both knew it was impossible to predict what might happen next but were certain we would enjoy it.

I took a deep breath and relished a moment of immense satisfaction. I looked in the mirror, straightened my hair, and put on some lipstick, before turning to go home. With one more glance, I said, “Damn you’re hot.”

Published 
Written by cliff_edger
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