My New Executive Assistant

"You have a tall, elegant grace, Laura," I said, starting to get personal. "I like that. The long skirt, I like that too. But if you were to work for me, I'd see you in a much more elegant dress. Much better shoes, too. Maybe four-inch heels, to emphasize your height. And much better stockings."

After I let that soak in a while, I asked her, "Does dressing well and being paid generously appeal to you, Laura?"

"I like what Cindy's wearing," she admitted shyly, with a smile at the younger woman. "Did you pick that out?"

"Actually that was one of her choices," I smiled and gave Cindy a playful goose to make her giggle. Then smiling up at her, I explained, "Though we had fun going through the catalogue together to pick it out as I remember. I picked out the stockings, though. She looks very good in darker stockings, too. And the shoes were my choice."

Cindy bent down for a soft kiss on my lips. That was a nice touch. I hadn't planned that but such things were why Cindy was so special to me.

"She likes to surprise me with new undergarments, too," I said, even more boldly since Laura was taking things so well. "I enjoy the company of smart, creative people. Hire the best, I always say, regardless of experience or qualification." I had tacked on the last of that just for Laura's sake. Usually an applicant had to be much more qualified to garner my attention.

"Cindy, Laura might have questions she doesn't feel comfortable poising with you here," I said, setting up the next bit in advance and making the situation clear to everyone. "Why don't you leave us alone for a while, but be right outside in case you're needed." As Cindy reluctantly left the room, I watched her lovely ass sway as she walked away. She was moving it quite nicely for my benefit, so I thought it only proper to enjoy the show.

Turning back to Laura, I could see that she was ill at ease. I thought I'd calm her down somewhat before trying anything physical. "Now that we're alone, the first thing I'd like you to do is just relax. You've made no commitment to me or I to you. Let's just chat for a while and get to know one another better," I said gently.

When she nodded nervously, I went on. "I've run this company for over fifteen years, Laura. It's a family business and I intend to leave it to my sons but that's not for a while yet. They're boys. I'm letting them have their fun.

"I'm looking for an executive assistant, as you know, but as you've also no doubt gathered, I'm looking for a very personal assistant as well. I've had - what is it? - six assistants over the years. They all stop by every now and then. Good girls every one. Many have gone on to other things. Three had families to attend to. I like a very nurturing, feminine woman, so that makes sense.

"I'm married, successfully but not happily. But that's entirely another matter. As much as possible, I never mix home-life and business-life together. My wife knows my proclivities and when we started out together, she shared all of them. That's about all you'd ever need to know about my wife. When, or if she should ever call, you'd best put her through. Hell probably just froze over."

I grinned, enjoying the quip and took a sip of my coffee just to catch a breath and let things sink in. People are always in a rush these days, I find. What's the sense of owning your own business if you can't enjoy the fun times? Like interviewing Laura.

"I'm generous, probably to a fault," I continued at my leisurely pace. "If my assistant needs days off, I have five former girls that often volunteer to come by and fill in for her on occasion. When you're off the clock, your time is your own, though I expect my girls to live up to a certain standard. No hard drugs, no going to jail, and certainly never calling or coming by my home. I probably won't be there anyway. I have ... other interests ... that I visit in the evenings.

"The pace of work is relatively easy. I have office workers and secretaries for the day-to-day work. The job of my assistant is to keep me productive and happy. I've worked hard to make sure I don't have to be too productive. That leads the assistant's job to mostly just keeping me happy.

I let this all sink in for a moment. It was a lot for a girl to be introduced to so quickly, I was sure. Finally I asked if she had any questions so far, wanting some feedback other than a blank stare.

"I was just applying for a job as a secretary," Laura mumbled, shaking her head.

"We have those, though I have no idea if we have an opening," I told her dismissively. "They pay about twenty thousand a year and it's hard, grueling work. You interested?"

"Yes. I mean, no," Laura said, looking confused. "I don't know if I'm interested or not."

"Let's talk about you then," I said easily. "What leads a beautiful, mature woman like yourself to look for an entry level job as a secretary?"

Laura blushed, but I had finally turned the conversation to something she was prepared to talk about. She sighed, relaxed a bit, and said, "I'm afraid I'm a bit of a cliché, I've found out. I never thought of myself that way before, though. You see, my husband left more than a year ago and we haven't spoken or communicated since. He ran off with a younger girl, a travel agent. At least not a secretary," she added with nervous laughter.

"I know I don't have much in the way of marketable skills," she continued. "But I'm smart and I pick up on things quickly. I have organizational skills, too. I run the music department for the First Christian Church here in town," she said, finally trailing off.

So, now that she was done sugar coating her past, I summed up for her. "Let's see, realistically, you're about thirty-eight," I said smiling since we both knew she was at least that old or older, "you have few skills, no experience and probably mounting debts. That puts your job prospects at...?"

"Nil," she answered truthfully. "That's about what I've seen over the last six months. Job prospects are nil." She looked sad and forlorn for just a moment.

"Or," I said, giving her an alternative. "You can come to work for me. Is it the pay that concerns you? I just said thirty-five because Cindy was here. That's what I started her at. I may be able to go a little higher for a woman in your condition. I'm sure you have bills that need to be paid immediately. I'll work with you on that."

"I'm sure you know it's not the pay. Let's be honest Mr. Williams, the pay is more than generous. It's the conditions that have me questioning whether I should take the job," she said earnestly.

"Let's talk conditions then," I agreed. "We have a nice office here. As my assistant, you'd have immediate status. People would treat you very nicely here. You'll even have some real say, once you've learned the business, I want intelligent people and I mean that. Only a select few know about your other job duties. They'll be discreet. They have very good reason to do so, I assure you.

"So that really just narrows it down to the personal, Laura. Let's talk about that, shall we. Personally, I find you very attractive. I hope I've made that clear without embarrassing you too much. Now it's your turn. How do you find me?"

Laura blushed. I don't think she was ready for such a blunt approach. She was plucky, though. She took a deep breath and blundered in. "You're tall. I like that, being tall myself. It looks as though you've kept fit. Nice suit. Good manners. Obviously you have money and breeding but..."

"Go ahead," I smiled warmly. "You won't hurt my feelings. I want your honest evaluation."

"You'd be perfect," she said, smiling warmly before she dropped the other shoe, "but I could never abide a man that would cheat on his wife. I think that's so low-class."

"That's blunt enough, I guess," I said chuckling and took a sip of the already cooled coffee. "Actually I prefer the term 'unfaithful.' My wife knows my infidelities, so I don't see it as cheating. It's also been my experience that even people of the highest class and breeding can be unfaithful. In fact, most of them are. I'm sure my wife is; though I don't particularly care. Kings are. Presidents are these days. Even Popes used to be, before they found religion." I grinned.

"But, I know what you'll say, Laura. Just because others do it doesn't mean it's right for you. Very true. Perhaps you're one of those chosen few that can maintain their class and dignity even under crushing debt and poverty. That's your choice to make, not mine. Everything here is by free choice, Laura. No one will pressure you to stay in a position that's uncomfortable."

"Low class was a bit... judgmental," she conceded. "I just don't know if I could do it. Even if your wife didn't mind. I just don't know."

"Well, there is only one way to be sure," I suggested gently.

"No!" Laura said quickly, becoming immediately nervous, almost getting up from the love seat to bolt for the door.

"Laura, relax darling," I said laughing easily. "I assure you that even as attractive as you are, no one here is going to rape you. I really enjoy taking my time with things, Laura. At any point where you feel uncomfortable, we stop. No questions asked. After all, I have plenty of women that will gladly accommodate any immediate urges I have. Relax, sit down, and then let me explain.

After she sat rigidly back down I told her, "I was thinking more along the lines of a more practical demonstration, dear. I have some very nice silk stocking that I'm sure would fit you. I keep plenty of extra around. You could put them on in my private bath. Then you could come out here and we could talk some more. If you felt like it then, you could just raise your dress a bit. No more than you felt comfortable. We could talk some more. Then if you felt comfortable enough, you might raise it some more. You get the idea.

"It would be fun for me and it would let you find out just whether or not you might enjoy working for me. If, by the end of the conversation, you haven't enjoyed yourself, then by all means this job isn't for you. What do you say, Laura? Would you like to give it a try?"

She thought a while, no doubt rationalizing to herself. But if she had meant to reject the offer, she would have probably done so outright. So I stood up and went to my desk and retrieved a pair of thigh-high black silk stockings. Lovely things they were in a size that ought to fit her.

I returned to my seat and set the stocking before her. She looked at them distrustfully, then reached out and took them off the table. I nodded toward the bathroom door, then interrupted her just before she walked towards it.

"Can I make one other small suggestion, Laura?" I asked. When she hesitated, I said, "If you want the test to really be valid, I'd suggested you wear just those under your dress. That way, you can really decide just how far you're willing to go. It's just a suggestion though. Do as you wish."

After several minutes, Laura returned. She had on the same dress, the same shoes and the same nervous smile, but now she had on the darker stockings. "Anything else to drink, dear?" I asked, purposefully tagging on the endearment again.

"No thanks," Laura said, sitting down nervously. She smoothed out her dress on her lap, leaving the skirt covering as much as it would. Little did she know how much I was enjoying the turn of her ankle and the lower portion of her calves.

"Would you mind if I talk about your legs or would that make you self conscious?" I asked politely. When she said I could, I went on, "I noticed your legs when I came back from dinner. I immediately told Cindy to send everyone else away. I told her that those legs were the legs I wanted on my new executive assistant."

Laura blushed under the flattery, but she did gradually raise the hem of her dress just a bit. It was still low, but with the adjustment the hem of the cheap dress came to about the middle her long, elegant lower leg.

"I wish I had some better shoes to let you wear," I told her. "I like to play a game sometimes. Let me guess how many pairs of shoes you have that you wear all the time. Not the old ones you haven't pulled out in years. Let's say the ones you've worn in the last two years, okay?"

"Sure, why not," Laura laughed, still a bit nervous, but relaxing somewhat as well.

"Let's see, you're a woman and you like to dress as well as you can afford to do. I can see that. That puts it at five or six inexpensive everyday pair right there, easy. I'll bet you also have a pair you only wear on very special occasions. Shiny black ones I'd imagine, with a little higher heel than the ones you have on. Three inches, I'd guess."

"How did you know that?" she asked amazed.

"Simple, really. You're smart and practical. Black shoes go with any wardrobe choice, at least a little. The three inches I guessed at because I don't think with your height you'd be daring enough to go with a five or a six, though I'd love to see you in a four or a five. Six would be too much for a woman of your elegance. Only a real tramp would wear six inch heels, right?"

It was all bullshit, of course. I'd seen her wear the shoes I had described at church before. She slipped them off to work the petals in her stocking feet, something I found particularly erotic.

"You really get into this foot thing, don't you?" Laura asked, raising her hem up just a smidgen.

I laughed freely enjoying the conversation and starting to enjoy Laura since she was relaxing around me. "Not a foot fetish, if that's what you mean. Close, I guess, but that's not how I'd describe it. Stockings and lingerie, now my interest in those might rise to a technical diagnosis of a fetish. I think of it as an incentive to run a profitable business. I employ over three hundred people here. Provide for their families and put food on their tables. I do it so I can see beautiful women in beautiful clothes. Well, a little more than just see them, but we'll get to that."

"Ask me how many pairs of shoes Cindy has in her closet that I've bought her the last three years," I told Laura.

"You haven't finished guessing how many I have yet," she laughed and said, smart enough to figure out my dodge already. But, she smiled a lovely wide smile and asked, "How many does she have?"

"Over a hundred," I assured her. "I lost count after that. If she wears the same pair in a month, I'll notice though. The same pair in three months and I still might, if I like them enough." I let the import of that settle into Laura's decision making process. I knew it had when her hem went North by another inch. "That's just the shoes," I told her suggestively. "My passion is a variety in stockings. Different hues, different textures. Seams and no-seams. Garter belt and elastic top. Shear toed and otherwise, the possibilities are endless. I like them all. I'll buy you them all. I want to see you wear them all." Laura's hem crept up a bit farther. She was almost to her knee by now.

"Knees are lovely things, I think, and women's calves and feet. I give good massages, by the way, but I'll also send you to a very fine salon I know. A day of beauty treatments and being pampered and massaged by experts: men, women or any combination you choose. I'll send you as often as you'd care to go. As long as you arrange a willing substitute, that is, which can be frequent. Professional nails, pedicures, hair, anything and everything you want, my nickel. No expense will be too small to make you look gorgeous, which won't be hard at all." Laura's hem crept up two inches on that one. Up and over the knee now. The idea of being pampered appealed to her, I could tell. She'd closed her eyes and actually moaned a bit when I mentioned the hair and pedicures.

"Vacations, too," I threw in as well. "I took Cindy to France late last year. She enjoyed it so much she's going back there for her honeymoon. I'm paying for that, too. As my assistant, you'd decide where we go and where we would stay. I feel the need for someplace exotic soon. Japan, the Far East, maybe even New Zealand I'm thinking. We'll see everything. Just one room, though, to hold down expenses." Laura had a far off look in her eye, no doubt thinking of distant places and lands. Maybe she didn't realize how far the skirt slid up this time, almost three inches. She had lovely long legs though, still plenty more to go.

"Infrequent trips to other cities too, though you'll plan those out far in advance. The best restaurants, the best hotels, Broadway plays, or Russian ballet. Whatever strikes your fancy." Another inch, perhaps two. I could see the very top of her stocking.

"I have rental property about town, not cheap stuff. Elegant places in nice neighborhoods. An agent runs them for me. You could take your pick of where you want to live, rent free, if you're so inclined. Or maybe you want the house you live in now fixed up. That's all negotiable. I want you to be very happy and productive." An inch of stocking top, that's all. Housing wasn't that important to her apparently. The sensuous stuff had appealed to her more.

"Then there's you personally, Laura. I know how to please a woman. You'll find real pleasure working for me. Sensuous delights. Other lovers if you wish, or none but me if that's your desire. You'll get excited just driving to work every morning. I want you happy and pleasured and ecstatic to work here." Her skirt came up past the tops now. Naked flesh! Laura was leaning back and breathing quicker and shallower. Her nipples looked hard as they poked through the blouse of her dress. She'd even taken her bra off, the luscious minx! Training Laura in her duties would be a real thrill, I could already tell.

"As many orgasms as you want, darling." I told her, raising up slowly and joining her on the loveseat. Laura looked startled for just a moment, but I sat far away and soon her panic eased.

She closed her eyes again and leaned back, indicating I should go on. "I love pleasure but I love giving pleasure just as much," I told her honestly. "A woman is never more beautiful than in orgasm and I love beautiful things. I'll make you climax until you're exhausted every day if you'll let me, Laura. You'll never want for attention and adoration. I'll eat you for breakfast and lick you for dessert each day if you want."

Laura's dress was now at her waist and the same mousy brown hair that was on her head was on her mound. The color looked far more attractive down there, though. As I scooted over and my hands caressed the smooth silk of the stockings, Laura spread her legs for me. That's when I knew that she was mine. When I felt sure she'd take the job.

"I love the way you look, darling," I said, thinking how nicely she'll look shaved down below. My right hand dipped and lowered between her legs, touching lightly over her wet labia and the smooth warmth of her inner thighs. As my middle finger agilely stroked the moist gap between her legs, my thumb began to deftly flick alongside her tender clitoris.

Laura was completely opening herself to me and opening herself up to her own sensuality at the same time, it seemed. As I scooted all the way up next to her, she reached out with her own right hand and began rubbing my crotch against the back of her hand.

Nuzzling against her ear, I blew warm air against it before continuing to talk her through her first orgasm as my assistant. "Anything you need to feel sexy and pretty, Laura. Men will drool when you walk by, every woman will envy you. You're Cinderella, Laura. This is your fairy tale. All you have to do is cum for me. Cum on my finger right now and it's all yours. Just let yourself go and it's all yours.

"Do it, Laura! Cum for me! Let go! Let go!"

Laura panted and tossed her head gently from side to side on the back of the loveseat.

"Cum for me! Cum for me, my sexy Laura. Cum for me, you sexy bitch!"