Assisting The Boss

The turning point in my life was the day I started working for Mr. Jameson as his executive assistant.

Having been hired through the personnel department, I never actually met Mr. Jameson until he returned from a trip abroad three weeks after I started. By then, I had already made the twentieth floor, where his offices were, my domain.

The first time I saw him in person, I knew my life would be forever changed. He walked off the elevator like he owned the place. Which, of course, was understandable, since he did own the place. He was somewhat tall, with dark hair and grey eyes that seemed to see straight into your heart, your mind. In his late forties, he had a very intimidating presence and it didn't help my peace of mind that he was extremely good looking.

I took a deep breath and didn't let my expression give any of my thoughts away. I had not made it to this position by allowing anyone to intimidate me. "Good morning, Sir." I said with a welcoming smile. I stood and held out my hand.

His eyes met mine as he came closer to my desk. A slight smile played about his mouth. "Miss Hunter. A pleasure to finally meet you in person." His large hand engulfed my smaller one. I wondered how those fingers would feel touching my skin... I shook my head. Where were these thoughts coming from? I had always been able to keep my work and private life separate.

"Is it not a pleasure, Miss Hunter? Why are you already shaking your head at me?" he said with a frown.

"No, Sir. I mean, yes, it's a pleasure to meet you. I wasn't shaking my head at you. Just thinking of something else. Irrelevant. Sorry, Sir." I smiled and shook my head at myself again.

"Thank you for taking over Mrs. Tyler's position." he said as he took the stack of messages from me.

"You're welcome, Sir. I appreciate the opportunity to work for you." I went around to the state of the art coffee machine in the corner near my desk. "Black coffee, Sir?"

"Yes, thank you. I'll be in my office. Maggio's for lunch, please. My usual, Miss Hunter." Mr. Jameson went in to his office, leaving the door slightly ajar.

"Yes, Sir." I muttered as I did a slight salute in the direction of his office.

"I saw that, Miss Hunter."

I grinned. "Sorry, Sir."

"For doing it or for getting caught, Miss Hunter?" A hint of amusement laced his voice.

"Getting caught, Sir." I said with a grin as I brought in his mug of coffee.

He laughed. Actually laughed. "I think we'll get along famously."

"Thank you, Sir. I believe I might like that." I leaned over his desk to place his coffee cup on the polished surface. Looking up at him, I noticed his eyes were riveted on my cleavage, exposed by my position. Hmm. Very interesting. I paused, bent over, and waited until his eyes raised to mine. I smiled slightly as I straightened. "Anything else you desire, Sir?"

His eyes slowly took in my dark hair pulled back in a bun, my button-down, cream colored silk blouse, and my straight black skirt that ended three inches above my knees. "Yes, Miss Hunter. In time."

"If you're sure, Mr. Jameson. I'll be on my desk...err.. at my desk, if you want me." I turned around and slowly walked out of his office, feeling his eyes on me the whole time, like a caress. I smoothed my hands down over my hips to the tops of my thighs, knowing he was watching. This was going to be fun.

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That first day set the pattern of our developing relationship. Over the next few weeks, we became very close. We continued our subtle teasing and I made sure he knew I was attracted to him by letting him 'catch' me looking at him.

He continued to watch me, his eyes showing his desire for me. It seemed he enjoyed the pursuit as much as I did, but I was frustrated. I was ready for him to follow through with the promise I could read in his eyes.

Hmm. What to do. What to do. I decided to up the ante. To find a way to tempt him into losing that iron control he seemed to enjoy wielding.

One Friday, a month after I first met him, I decided today would be the day. I had picked up a new outfit for the express purpose of seducing my boss. My new red dress reminded me of the 1940's style and had a sweetheart bust that allowed the tops of my breasts to show. The fabric of the dress lovingly hugged each of my curves, the skirt flared out, ending at my knees.

I put on my usual stockings and garters then my three-inch red high heels. Pulling my hair back, I put it up in my normal bun, allowing a few tendrils to frame my face. After putting on matching red lipstick and perfume, I headed in to work.

Mr. Jameson hadn't arrived yet, of course. I went about my daily routine, preparing the coffee, checking the messages and emails.

At 7:50, I looked at the clock, smiling to myself. Mr. Jameson would be in soon. All of my work was caught up and we had a very light schedule that day. I had made sure of that in anticipation of my plan to spend the day seducing him.

I heard the elevator open and glanced up. He was so sexy. I leaned back in my chair and sat up straighter.

"Good morning, Mr. Jameson." I said with a smile.

He had been looking down at his smart phone, but looked up at my greeting. He actually did a double-take when he saw my new outfit. "Good morning, Miss Hunter."

He took the stack of messages from me and headed in to his office. I poured his coffee and brought it to him. I paused in the doorway until he glanced up at me, then walked across the carpeted floor to set his coffee on his desk. He watched me the whole time.

He had his laptop open on his desk. "What do you think of this email I'm writing, Miss Hunter?"

I walked around the desk, leaning in close to him so I could look at the computer screen. "Sorry, Sir, but there's nothing there."

"Really?" I felt his hand touch the back of my knee under the skirt of my dress. It glided slowly up to the top of my stocking, finding my bare thigh. "Mmm, Miss Hunter. There's nothing here either." His hand had found my bare ass.

"You're right, Sir." I stepped between his spread thighs, continuing to lean over his desk.

Both of his hands had now found their way beneath my skirt. I looked back at him, biting my lip. I reached back, grabbed the skirt of my dress, and flipped it up so that my ass was bare to his view. I spread my legs farther apart and reached between them to play with my wet puss. I was soaking wet.

Mr. Jameson groaned and knelt on the floor behind me. His mouth ground itself against my puss. He was very good with his tongue. He licked and suckled my clit as he inserted three fingers inside me. Then a fourth finger. His thumb found its way inside as he continued to nibble at my clit.

I pressed back against his hand. His mouth. "Oh, Sir. That feels so good. Oh, yes. You're gonna make me cum."

His fingers worked faster inside me. Right as I was about to cum, he pulled back. I gasped. "No!"

He sat back in his chair and unfastened his suit pants. "Suck my cock, Miss Hunter."

I immediately turned and knelt in front of him. My mouth took his hard shaft inside. My tongue moved around the head as I took him deeper inside. I moaned as I continued to pleasure him. I kept moving my mouth up and down until I knew he was almost ready to cum. I slowed down the movements of my mouth and stood.

Leaning towards him, I released my breasts from my dress and rubbed them in his face. His hands grasped them as he suckled at my nipples each in turn.

Grasping his cock, I straddled his lap and lowered myself onto him. He groaned as he grasped my hips and helped guide me. "That's it. Ride my cock, babe."

And ride his cock, I did. With his help, up and down, I slammed my puss onto his cock. Faster and faster I went. He felt so good inside me. Deep inside.

I held his head as our mouths met in a deep tongue-dueling kiss. His mouth moved to a very sensitive spot on my neck that completely drove me crazy. I slammed my puss down onto his cock and finally.. finally.. Exploded. I screamed and felt his shaft throb as he filled me with his cum.

He held me close as our breathing settled. "I take it you like my new dress?"

He laughed against my neck. "Yes. Very much, Miss Hunter."

I stood up, straightening my clothing. "I better go freshen up."

He smacked my ass as I turned to leave his office. "Clear our schedule, Miss Hunter. We're going to my house for the weekend."

I walked to the door, turned towards him, and gave him a saucy salute. "Yes, Sir."

I heard him laughing as I left the room.