My Executive Assistant

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Boss catches his young assistant on the rebound.
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Miltone
Miltone
462 Followers

"After the long day we've had, I feel like taking a swim and plopping myself in the whirlpool for a while," I said with a deep sigh to Kate, my executive assistant.

We had just stepped into the hotel elevator and I had just pressed the button that would take us to the third floor. My back was sore from setting up our trade show booth all afternoon and I was looking forward to an evening of rest and relaxation before the deluge of sales prospects the next day.

"That sounds like a great idea," Kate replied, with a flirtatious smile that dazzled me senseless. She punched the fifth floor button. "Why don't you give me a few minutes to get ready and then stop by my room to get me?"

"Uh, yeah, Sure. I can do that," I said stumbling over my words and train of thought. It didn't matter what she said to me, I always felt like such a klutz around her.

"Room 545," she whispered as the elevator door opened up.

"See you later," I nodded stepping out.

I looked back to see her give me another warm smile with her full pink lips that never seemed to need any lipstick or gloss. Her clear, light-blue eyes twinkled as she shook her soft thick amber hair back from her face and behind her narrow shoulders. After the door closed I was still standing in the hall taking in the scent of her perfume. I smiled to myself as I walked to my room, my thoughts full of Kate, sweet Kate, my Kate.

She had come to work with us over a year before as a receptionist. I fully remembered the day that the HR director brought her around for introductions. She had boldly reached her hand out for a shake and I remembered her firm grasp, the soft skin, the smell of her perfume, and the angelic face that smiled broadly. I remembered thinking that she was the most beautiful girl who had ever passed through the door of McDonald Design Associates. Mid five feet tall, with a heart shaped face and a heart shaped butt, firm, round breasts and a pair of long legs that always showed so well in even the most modest business suits and skirts that she wore. She was the kind of young woman who always wanted to be my friend, but who would never go for me as a boyfriend or lover.

I looked forward to chance meetings with her in the break room, or maybe a brief chat at the front desk as I waited for my faxes to go through. We shared a few stray moments in the hallway chatting superficially and once in a while a few minutes by the coffee pot in deep conversation. As the weeks passed by, I found out that she was living with a guy and wasn't real happy. She was from a rural farming community up north. We both liked all kinds of music except the real hurting Country and warbling Opera.

Although she seemed to get along with everyone, she commented once that the other women didn't seem to like her too much. They were civil and friendly, but no one had asked her to do anything outside of work, and jealously guarded their boyfriends at the company Christmas party, even though her boyfriend was present. You can imagine my surprise and pleasure when my long-time assistant went on maternity leave and Kate asked to interview for the job. As the HR Director and I sat in the large conference room, she presented herself so professionally that I almost forgot about how hard it would be to work with such a beautiful young woman. But I was determined to do so and pleased with the way she stepped in and took on every work assignment.

As Sales and Marketing Manager, one of my responsibilities was organizing trade show appearances. Seeing it as something of a test for her, I assigned responsibility for making arrangements to Kate. She did a wonderful job of securing the booth, designing the layout, ordering signage, furniture and utilities. She took the ball and ran the whole nine yards, which I appreciated since I could spend more time concentrating on working with our customers. I began to hand over many of the marketing duties, designing and placing ads, working up brochures and flyers, even setting up and hosting training classes for employees and customers.

She was such a hard worker that I rarely found myself distracted by the sway of her round hips, the jiggle of her firm breasts, the scent of her perfume. There were just a few times, like when she would bring something into my office for approval and would lean over my desk and her blouse would open slightly, just enough to show how her lacy white bra was barely able to restrain her gorgeous tits.

There was the time in the middle of winter when I had stepped up to send a fax as she was coming in after hanging up her coat. The sight of her as she paused for a moment to raise her arms up to pin her hair back behind her ears turned me into a statue, especially since her nipples were standing out against the soft plush of her sweater because of the cold weather. She must have known why I stood there for a minute or two, so speechless. But she took her time pinning her back, her light blue eyes looking straight into mine, her sweet sexy body an absolute turn-on.

Then there was the time when I had stumbled into her office unannounced and saw her with a leg up on her chair as she was pulling up and straightening her sheer stocking top on an exquisite leg. The sight of her tugging at the lacy stocking top and the brief glimpse of her supple thigh and the dark panties above gave me an instant hard on that I had to hide behind the manila folder in my trembling hands. When I cleared my throat and looked down with my cheeks blazing red with embarrassment she looked over at first in panic, then with a smile as she brought her leg down and let her skirt fall back into place.

"Sorry," she said with a laugh. "I didn't mean to embarrass you, but I guess I have that effect on men somehow."

I babbled on about how I didn't mind and that I wasn't there long enough to see anything. She just smiled at my lie as if to acknowledge that she had my number. But she never seemed to take advantage of it and as the weeks melted away we went back to being perfectly professional. A week or two later, I was in the lunchroom talking with Peter, the Controller, who was one of my best buddies at work. Peter was our token frustrated married man whose wife had cooled down a lot in the years since they were married. He had bought her a sexy little outfit for their anniversary and she had refused to wear it for him.

"So she wouldn't even try it on?" I asked.

"No way, no how!" he replied. "It's not like it was really nasty or anything, you know crotch-less or cup-less or something like that. She's still got her figure and all, and to be honest would look pretty nice. But no way would she even try it on."

"That's sad, Pete," I replied, patting him on the back. "And one reason why I won't get married again."

Just then Kate and come in to refill her coffee cup.

"What's so sad?" she asked as she poured out a cup.

"Pete's wife won't dress up for him," I said.

"Well, not that he would, the pissy way he's been acting lately," Kate said stirring in her touch of cream and two sugars. "But if my guy brought home scads of lingerie, I'd try it on for him. You know, give him a little show."

Peter and I looked at each other in amazement, both of us forming a mental picture of the event.

"Powder blue," I said.

"No," Pete replied. "It'd have to be black."

"What?" she asked, taking a sip of coffee.

"Blonde girl," Pete said. "It would have to be black."

"Oh, I get it," she said, reaching up to let her fingers glide across Peter's cheek as she passed by on the way back to her office. "Wouldn't you just die to know."

Peter pounded his palm on the counter top as she swiveled her lovely heart-shaped ass through the doorway. Her slacks were just tight enough to show off the perfect curves of her butt.

"Two words for you, Pete," I said, following in her wake. "Thong panties."

Peter bent over and groaned as if in deep pain. For the next hour it took much more concentration than normal for me to go about my business without imagining sweet young Kate in a delightful light-blue or black lingerie ensemble. For the next couple of days, it set up a running joke. When Peter and I would pass each other in the hallway, one or the other would say just one word like "black", or "blue", or "white", and the other would crack up. At one point, Kate had paused in the doorway to her office to let us pass by, and caught on to our juvenile banter.

"By the way, fellas," she said with a sexy smile, loud enough for only the two of us to hear. "I'm partial to blue and wear only thong panties."

Of course that brought both of us to stop in our tracks and watch as she walked past toward accounting. And two weeks later finds Kate and me in our hotel in Chicago for a large industry trade show. I had always noticed that the show traffic was higher in the booths that had a pretty girl on staff and was looking forward to testing my theory. We had loaded up the van early in the morning and arrived in by early afternoon. The drive was pleasant and seemed to go by so quickly. We were both dressed casually for a change, Levis and a sweatshirt for me, tight black jeans and a sweater for her. It seemed like we never stopped talking the whole trip. She talked about life with her boyfriend Rich. I talked about my life as divorced father of two. We talked of events in our past, our plans for the future. She reclined a little in her high back bucket seat and watched out the window a lot. I couldn't help but noticed the slight jiggle of her breasts as we rode on.

"You know, this may sound stupid, but I've never been out of the state," she said with a touch of excitement as we crossed the Illinois state line.

"You're kidding," I remarked. "You seem so, ..., oh, I don't know," I said struggling to find the words." You seem so worldly."

"Well, I'm really not," she replied turning back to face me with those large, clear blue eyes and full pouty mouth curled up in sweet smile. "I mean, I've been around the block a couple of times, but the blocks in my neighborhood just weren't very long, I guess."

All too quickly we arrived at the convention hall and unloaded everything. I was surprised as she stepped right in and helped handle setting up the booth hardware. There was only one awkward moment when I brushed past her as she was assembling the booth backdrop. There wasn't much room and it was almost as if her beautiful round ass moved back to brush my lower belly as I slipped behind her. Although I wasn't erect at the touch I was getting there when I stooped down to reach into the tool box and turned back to see her smile down at me. I swear that I could see her nipples get erect as well. Without a word we went on with our setup. When we were almost done, she sat on the table out by the aisle and I noticed that the guys in the booth across the way were all checking her out. The boldest came over for some chitchat. I could tell my theory was bearing out well.

By five o'clock we were pretty well set up and checked into our hotel. As I hustled back to my room to change I began to let my mind drift away and fantasize about what Kate might wear to the pool. I tried not to let myself think of her in a skimpy little bikini. No, if she were the professional career girl I thought she was it would be a more modest one piece like the Olympic swimmers wear. I started to change and decided to rinse off in the shower first since I had worked up a sweat that afternoon. I pulled on a baggy t-shirt over my swimming trunks, slipped back into my topsiders, and headed up to her room.

"Tunk! Tunk! Ta-Tunk! Tunk!" went my knock at her door. I fidgeted as I waited. Would it be the bikini or the tank suit? Maybe one of those new "tankini" suits. I tried to control myself but my mind was racing far ahead of me.

I knocked again and waited. Leaning my head toward to door, I tried to listen for any sounds of life. I checked the room number again. Yep, room number 545. Finally the door opened up and Kate silently let me in closing the door behind me. She was still wearing her sweater and jeans. Her room seemed humid as I stepped in and stood awkwardly at the entrance. The air was a strange mix of her perfume and another aroma. Salt? I wasn't sure. Her open suitcase lay on the slightly rumpled bed as if she had been interrupted in putting her clothes away. I could see her lacy underwear arranged in the open drawer. She had drifted into the room close to the bed and stood with her back to me when I noticed her shoulders shaking.

"Are you okay?" I asked hesitantly.

"Yeah," she said with a sob. "I'm all right."

I moved closer to her and saw her shoulders shake again and heard her begin to cry.

"What's the matter?" I asked stepping over to her and placing my hands on her shoulders.

Her tear-stained face turned to look at me as she swung around and looped her arms around me. She shook as she clung to me.

"It's that bastard Rich," she sobbed. "The son-of-a-bitch just broke up with me. I just don't need this now. I just don't."

"Oh, come on, it can't be that bad," I said in my most soothing voice. "How did this happen?"

She slowly began to get control of herself and her sobs subsided. She dabbed at her eyes with a sodden tissue that was crumpled in her hand then buried her face into my shoulder. I could feel her tears soaking through my t-shirt. I slipped my hands around to hug her and hold her close as if to absorb the hurt feelings that were flowing from her. I could feel her shoulders shake and her body quiver with emotion.

"I was starting to unpack and thought I'd call him and let him know where I was and all," she began as her composure slowly returned. "Fool that I am, I was even horny enough to have some phone sex with him. But when he answers, I could tell that bitch of a neighbor was over. The bastard was with that bitch!"

"What? Who?" I asked quizzically.

"Oh, just the bitch who lives in the apartment next door," she said as she began to pull away from my embrace. She turned and walked over to the window and looked out at her "wonderful" view of O'Hare airport. "I knew she and Rich have been carrying along for a while. It started when he dug her out of a snow pile last winter. He swore it was over, but then I heard her making noise while he was talking to me on the phone. I mean for God's sake she was blowing him while he's on the phone with me!"

"Oh, Christ!" I sneered. I grabbed a couple of tissues and stepped over to her, putting my arms around her again. I offered the tissues to her. "What is it with some guys? I mean, if I had someone like you, I sure wouldn't be catting around. I'd feel so lucky that I don't think the thought would ever occur to me."

"Yeah, that's guys like you, Jack," she said, taking the tissues and mopping her eyes. "God, I just have the worst luck with men. The ones I'm attracted to just end up treating me like shit. I don't know why. I give them everything. Everything! There isn't anything that I haven't done for him or any of the others for that matter. I suck them and fuck them. I let them fuck me up the ass and swallow their cum. And then they always do this to me. Every last one of them!"

"Maybe you're looking for men in the wrong places," I suggested. I had looped my arms around her, just below her breasts. I pulled my arms up feeling the weight of her boobs settle on my forearms. "Or maybe looking for the wrong type of man. I mean, those Badass types may look so fine and be fun for a while, but..."

I started to think about what I was saying and realized that here she was pouring her broken heart out to me and I'm slyly trying to feel her up. Kind of ashamed of myself, I began to pull away.

"Please don't let go of me," she asked, slipping her arms up to pull mine closer.

Her sobbing and sniffing slowly subsided. We stood together silently for what must have been five minutes. The warmth of her body was melting into me, the perfume sprinkled around her neck filled my senses. From knees to neck there wasn't a gap between us, her ass to my belly, her back to my chest. I reached out to pull the curtains open so that we could get a better look at the airport. As the sun dipped lower in the sky, the horizon began to darken into a beautiful blend of purple and red and pink. The lights on the airplanes were plainly visible now as they lifted off the ground into the air."

"You know, you're right," she admitted. "I need to start looking in different places. Like maybe some of the places those planes are going."

"Maybe you only need to look an arm's length away."

She tilted her head back, eyes closed. "Oh, Jack, you don't need to be so nice to me. But thank you anyway."

"So would you like to go for that swim or not?"

"You know," she began. "As nice as that sounded earlier, I think I need some dinner more."

"Well, I'm hardly dressed for dinner," I replied. "I'll have to go change."

"Why don't we order room service?" she asked innocently, turning slowly within the circle of my arms. "I mean, are we allowed to expense room service?"

"I don't think so," I chuckled. "You know how the Big Guy is. I'll go change."

"You know, I really don't feel like going out right now," she said looking up at me with her big blues eyes, a bit red and puffy from her tears, the high cheekbones stained with her tears, and leaning into my soft embrace, her stomach and breasts burning into my body. "I must look like a witch!"

"Kate, you are the most beautiful woman I have ever laid eyes upon!" I blurted out. I asked myself where that had come from and didn't have an answer. It was like my mouth was working independently from my brain, except that is was saying all the things I had wanted to tell her but had thought were inappropriate. "I have thought so from the very first day I met you. And seeing you here, in this state, all upset and crying, just rips at my soul. I find you so irresistible that you could ask me to go down to dinner naked and I would."

She leaned up against me looking up into my eyes, as if trying to see whether I was bullshitting her or telling the truth.

"So would you?" she asked, trying to keep a straight face.

"What?"

"Go down to dinner naked?"

"Let me think about that one."

"Shucks, just my luck," she sighed. "I'd really liked the idea about seeing you naked, I mean even if you are my boss."

We laughed and embraced. She buried her face into my shoulder. She turned her head and pressed her cheek into me. Her hands began to rub my back and drifted lower to cup my ass through the thin materials of my swim trunks. I responded by letting my hands drift up and down her back, rubbing her backside from shoulders to waist. She rocked up on her tiptoes to bring her face closer to mine. Our breath was mingling as her mouth drew closer to mine. Our eyes closed as we lightly brushed lips. We pressed closer together. Our mouths opened and our tongues met. After our long, deep kiss, I pulled away.

"Wait a minute!" I blurted out. "This is crazy!"

"I know it is," she echoed, stepping back. "You're right. Let's get control here. I mean, this is crazy!'

"I'll tell you what," I began. "Let's order room service, my treat. And then go down for our swim."

"Yeah. That's better. Let's do it!"

So we ordered room service, just a couple of hamburgers and a fruit salad, and a carafe of their house wine. I sat on the easy chair by the windows while she sat cross-legged on the bed and we talked. Surprisingly, after our hours in the car we hadn't yet run out of topics. We talked of life outside of work. I told her of the latest jazz concert I had seen. She told me of the local pub that she frequents and the strange clientele. We spoke a little about family, the folks she had left behind, the family that my ex had

"I hope you can forgive me for what just happened," she said looking me straight in the eye. "I mean, I never should have kissed you."

Miltone
Miltone
462 Followers