My New Executive Assistant

Edited by: Sixty-nine

As we sat at one end of a long, brown, wooden pew of our newest church my wife had dragged me to my mind wandered to the organist's long legs.

Peggy, my wife of twenty years, was the religious one of us two. I made no bones about the fact that I was not and reminded her of it often enough. I went with her to the churches she picked out as a marital courtesy. Some we would join - for a time. Most, however, we would not. Peggy always found a reason to be critical and found something wrong with almost every new church we attended. Personally, I liked this one. The organist had great legs.

As long as I made the money to keep her in nice clothes and a high place in society, Peggy was tolerant of my eccentricities. After all, she wasn't that religious. None of the shallowness really soaked into her core but, although she would never openly admit it, she loved the trappings. The more ostentatious the better.

Just over a month before, we had left the Episcopal Church we had attended for almost a year. Peggy said it was because Episcopals had a soft stance on gays in their priesthood. In my opinion, although I would never openly admit it, she had left because of the new carpet they had put down three weeks before. It had been a hideous shade of burnt orange. Perhaps a bit of the shallowness had soaked in, after all.

The lovely woman waved those long legs under that organ. A tall woman, perhaps 5'10" with those long, slender legs, she wore her mousy brown hair short, emphasizing her long regal neck.. She wore long dresses, which I like, but pulled them back so the skirt didn't interfere with the pedal action.

The church was laid out in a semicircle. By chance, we had ended up far to the side about ten rows back from the organ. Even though the church was packed with more than its share of young singles and couples, this side of the auditorium remained comfortably less crowded. Maybe it was the great view of the organ in profile that drove people towards the middle. The moment I saw the organist and her great gams, I knew I'd at least have something decent to look at during the service.

Not that I was a cad about it. Peggy never had reason to fault me on my public persona or appearance. As the heir to a small manufacturing plant, I had a certain image I needed to project. The business was a moneymaker, but not so much these days. Fortunately, between the money coming in and the family inheritance we did all right.

As long as I kept Peg's extravagance in check it wasn't totally bad with her. She still wore the stockings I bought her and the lingerie I provided. We didn't have sex often any more. Peggy didn't seem all that interested and my own interest in her had begun to wane about ten or fifteen years before. But she could still fill out a chemise and had a great set of calves and ankles. She looked especially good in three-inch stiletto heels and still owned a round thirty pair I'd bought her over the years.

I decided, after studying her, that the organist wouldn't look as good in stiletto heels. She didn't have Peggy's well-defined calves that the stiletto's brought out so well. Instead the organist's legs were elegant tapers, flowing smoothly from ankle to knee. I couldn't quite decide what kind of shoe she'd look best in. I'd love to experiment, though. Those were worthy gams to work with.

She'd definitely need better stockings, my calculating mind determined. I was sure she always wore cheap store bought things. Probably damned panty hose, I sniffed in disgust. Why would any woman wear panty hose when she could buy fine silk stockings to enwrap her legs with? I began to get an erection thinking about those elegant tapers in fine silk stockings. It made the time pass.

On Monday I had too much work to do. My executive assistant of the past three years was leaving me. The silly, little girl had decided she wanted a family after all. Despite her flawed judgement she was a good girl and had been a great assistant. Cindy was leaving with my blessing and I would even be the one to give her away at the altar. We had gotten that close over the passed three years.

While Cindy lovingly sucked my cock that Monday morning, I thought about how much I was going to miss her. She had wonderfully thick honey-blonde hair that was styled just enough to look great but not so much that I couldn't run my hands sensuously through it as we played together. I loved the feel of her hair as she slowly suckled me; it was silky and always so warm next to her scalp.

As she continued her business, I went over exactly what we'd be looking for in my assistant's replacement. "She's got to be professional looking, of course. I might even want someone a bit older this time, not that you haven't been a lovely child. Great legs, of course. That goes without saying. She has to have a certain class and elegance but she has to want the job enough that she needs to stay here for a while."

I realized that in my mind's eye I was talking about and thinking about the organist. I knew myself well enough to know that I was like that. I could always be a bit obsessive when it came to the women I enjoyed. I was good for them though, generous to a fault. I loved to buy them gifts, especially perfume and clothes to wear, and I always treated them like a lady, at least in public.

It was a perfect job for the right woman, really. I tried hard to be a perfect boss.

Cindy's lips and her sucking were just perfect, too. A large part of me was going to hate to lose her. Still, it was always fun to break in a new girl.

"Up on the desk, Cindy-darling," I told her with heartfelt familiarity. "I'm almost ready."

Cindy knew I liked to finish in her cunt. I'd had a vasectomy after my second son was born so it was safe to cum inside my gorgeous young assistant. After all, I loved to hear her tell me how my sperm was dripping out of her all day long. She would walk up to me and whisper in my ear, pretending to be talking business. Mostly, she was telling me how my semen was soaking into the tops of her stockings. If she were especially good about telling me, I'd even buy her a new pair.

Cindy leaned back with her skirt pulled up and I easily slid into her well-trimmed, blonde haired cunt. She moaned very nicely as my familiar cock entered her again and again. Cindy always had been a passionate girl, even from the first time I'd fucked her during her job interview.

"Fuck, I'm gonna miss this, Roger," she groaned and thrust her hips in shallow motions without her ass cheeks leaving the desk. I'd encouraged her to learn to talk dirty when we were alone, especially when I was fucking her. Otherwise, she was expected to be the model of grace and poise.

"You can always visit regularly," I smiled at her, bending forward and kissing those lips that had just been warming up my cock. "You know I'll always adore your pussy."

"Can I come by when I'm lonely and have Daddy fill me up with his yummy juice?" she whined playfully. She'd had a secret fantasy about her father that we'd played with over the years. It had been fun at first but lately it was getting to the point of being annoying.

"You'll have to make an appointment, or I'll have to give you a spanking," I told her as my thrust increased, keeping in character for the sake of her pleasure. "You might have to do some special favors for my new assistant too to get the appointment but don't fret, dear. You know I'll pick one with a nice tasting pussy, just like yours."

"You're so bad, daddy," she giggled. "Would you like to watch while I ate her out? Watch me as I fingered her gorgeous pussy? Would you want to fuck us so we could suck your cum out of each other's wet, nasty snatch!"

I crammed my cock deep into Cindy's perfect pussy and left her with a full, sticky morning load. As spurt after spurt fired off into her eager cunt, all I could think of was how good it would look running down her thighs all day, soaking through these beautifully shear silk stockings she was wearing.

We kissed as I slowly pumped into her, giving her the final drops of my load. After we were done, I had the pleasure of seeing Cindy smooth the sheer, black panties over her well-fucked pussy and of witnessing the first thick glob start to soak through the impossibly thin material at her crotch. Cindy smiled impishly before bounding energetically off the desk to kneel down and suck her flavor off of my limp cock. She lovingly tucked it away, for a while anyway, and licked her lips as she was zipping me up.

The rest of our day would be taken up with interviewing for her replacement. Cindy would weed through the candidates. Anyone not pretty enough or literate enough would be politely sent away. Any women or girl of promise would be given a few extraneous 'tests' to see if she qualified. Light word processing and the ability to compose a grammatical sentence were requirements. Light work aside, I did have some real work that needed to be done on occasion.

I paid Cindy between fifty and sixty thousand, a generous salary for a girl with no college and little experience when I first hired her. Plus there were all the fringes I offered: paid vacations-- with me of course, a stunning wardrobe, and, of course, the frequent orgasms. I prided myself of treating my women right, especially in public.

While she started the interviews, I made a few phone calls and played catch-up on the few business details that demanded my attention. I had good people working in production, people that had been with the family for years. Many of their own sons and daughters came to work for us, too.

My business had strong ties in a lower tiered, economically depressed city. We were just big enough to be an important employer in town, but not so big that government was always after us with their greedy hands out. It meant being savvy and nimble, being just the right size and just the right profitability. Too rich and the vultures hang around, too poor and I wouldn't have been able to play as much. A few palms greased with just the right touch, and the right balance would do. The right mix of business and pleasure!

It was never easy and it did sometimes take adjustment. When African-American politicians came into power in the eighties I had been forced to adjust. I hired an African-American executive assistant who was indirectly politically connected and she helped me to integrate the firm, including some senior staff positions. She'd been so swift and levelheaded that I'd paid her way through a respectable business college. Charmaine still came by to visit me on occasion. She had great legs with nice, firm thighs, the best thighs and ass I'd ever seen. The girl loved to fuck, too! She'd been a great, fun assistant for about three years.

After lunch, I was walking through my atrium when I saw them: those elegant, tapered legs in cheap panty hose were crossed and waiting my waiting area. I didn't even have to look up to know that the organist from the church we had been attending was the woman filling out an application. I gave her a friendly smile as I walked by and was gratified to see that she hadn't even recognized me. It made sense, I suppose, since we always came late to service and the organist was always busy. What wonderful luck indeed!

Calling Cindy aside, I pointed out the organist through a crack in the door.

"I want her," I said plainly, "if she has the temperament, of course. Sound her out, but be subtle about it, girl. And give her a very thorough review. Let her think she has to really work hard to get the job. You understand the drill."

"She's a bit old, don't you think," Cindy remarked, her catty side showing through.

"She's not a total babe like you, my pet," I flattered her. Cindy was smart enough to know that it was flattery, after all I never hired stupid girls. 'There's only one Cindy to me, darling. Remember, we're not looking for your twin. In fact, I like that she's so different, really. I'm going to miss you."

We both looked out on the dozen or so applicants in the atrium filling out applications. The organist wasn't the most beautiful of the bunch, but she had the best bearing, an intangible sophisticated air that belied her cheap, off-the-rack clothing.

"Nice legs, even in those cheap stockings" Cindy conceded. Those long thin tapers were twined around each other in the way that only long-legged women can do. "Dress her up better and she might do." Cindy hadn't known a thing about stockings and dressing up when she had come to work for me. On her interview, she hadn't even worn stockings. It almost made me reject her outright. Still, she had great ankles, a willingness to learn, and a very talented mouth. A wonderful combination.

"I've seen her at a church Peg drug me to," I mentioned, throwing cold water over the atmosphere with the mention of my wife. "Don't know if she's serious about the church work or not, though. See if you can bring the subject up."

Efficient as always Cindy had the rest of the applicants sent merrily on their way within an hour with a simple, friendly "We'll call you if we need you" for their time. It took her another hour to test my lady and do the initial interview. Occasionally she'd pop in, knowing I was anxious, to fill me in on how it was going.

"Her name is Laura Robertson," Cindy informed me. "'Laura, how Doctor Zchivago! She seems smart, though. She's desperate, too. Husband left a year ago. No appreciable income since. No real experience in the last twenty years. She actually took typing in high school, can you believe that? How ancient!"

"What about the church thing?" I asked a bit too nervously.

"She actually listed it on her resume, for Pete's sake," Cindy giggled. "They pay her, not too much I might add. She's not even a member. She joked and said it barely keeps her in stockings. For true! No wonder they're so cheap looking!"

"Does she look like she might be willing?" I asked the crucial question.

"Not too sure," Cindy said, her eyes gleaming impishly. "I didn't try to lick her tonsils or anything, but she was friendly. She seemed desperate to suck up, especially when I told her about all the really well qualified applicants we'd seen today. I've primed her all I can, Roger-dear. Now it's up to you to deliver the pitch, so to speak."

"I'm ready, darling. I've been ready for an hour. When you bring her in, bring in some coffee for me, plus whatever she'll have. We'll start away from the desk, of course, and stick around a bit until I dismiss you, okay?""

"Sure you don't want me here for the whole interview?" Cindy asked, her hand lightly caressing my erection in my trousers. "Oh, my, you are primed and ready, aren't you?"

"I'll do the first interview on my own, you minx. If you're nice, I'll let you participate in the follow-up interview."

"I'm really gonna miss the fun we have, daddy," Cindy purred, casually stroking against my trousers. "Too bad you went and got snipped. I'd love having your naughty babies."

"You're gonna make a great mom, Punkin', and Sam's a lucky guy," I told her earnestly. Then, giving her smaller breasts a nice fondle so they wouldn't feel left out, I added, "Wish I'd had these lovelies to breastfeed on when I was a kid."

"I can always stop by and give you a taste after I get my figure back," she said, continuing to purr seductively.

"You'll stop by anyway, even if you get big as a house," I teased her firmly, though I really didn't mean it. Then, giving her an evil, playful grin, I added, "Of course, the bigger you are, the harder I'll have to spank you."

"You're so bad, Roger," she laughed aloud. She rarely called me Roger, in public or privately. "Let me get this poor, unsuspecting woman in here."

I was seated in my executive high-backed conference chair when Cindy escorted Laura into the room. She pointed toward the upholstered love seat alongside and against the wall, which Laura eased herself down into, tucking her skirt under her thighs with an elegant, thin wrist and slender hand with long fingers.

I continued to examine her resume and application, though in fact there was little there. Even so, in my tailored suit and my tall, lean frame, I'm sure I presented the image of the successful businessman that I was wanting to project.

"Oh, thank you, Cindy," I finally said, smiling and praising my assistant warmly as she set my coffee down before me. When she served Laura what looked like tea in a similarly elegant cup, I raised my head to look at the woman and smiled.

"Well, Laura," I began pleasantly, "thank you for coming by today and applying for the position. It seems as though everything is in order here. I assume Cindy has told you all about the position."

"Well, most everything," Laura said softly.

Cindy came to stand dutifully at my right side; her hand placed strategically territorial across the back of my chair.

"Any questions you'd like to ask?"

"Not that I can think of," she said, obviously lying. In her place I'd have a million questions. No wonder Laura was having problems finding work, she gave a terrible interview.

Her discount store dress looked proper enough for a business interview. The skirt fell just below her knee. On her tall, slender frame, her bosom looked respectable, if not overly large. Not being a breast man, that didn't matter much. She did have on a pair of black heels, but they were only two-inchers and the style was insipid and uninspiring. Still, she had a nice smile and I loved the way she held her legs when she had turned somewhat in my direction.

"Well, there doesn't seem to be too much to discuss about your resume," I suggested, dismissively waving the one page bit of fluff that said nothing. "We have your numbers, we'll call you if we want you to come back."

As I went to rise up off the chair, Cindy being the smart girl that she was, played her role just excellently by bending down and whispering into my ear. "I just loved the way you fucked me this morning," she said softly, looking so professionally businesslike as she did so. "My thighs are still sticky right now. Want to feel them?"

"Really? That's good to know," I told her aloud, giving her a quick wink of approval with the eye furthest from our candidate. Then turning back to Laura, I asked offhandedly, "Cindy says you have some secretarial training from high school."

As Laura fumbled for a response, I used the back of my hand to openly caress Cindy's thigh. My assistant understood my purpose and smiled warmly was Laura stumbled over her words, watching my hand so inappropriately stroking high up on my female employee's leg.

When she finally fell silent - what was it she had said again? - I moved my hand from the front of Cindy's thigh to gently fondle her ass cheeks. The hand was behind Cindy from where Laura was sitting, so I made larger, more obvious gestures to be sure she got the picture.

"Cindy's been with me for three years now. I'm really going to miss her. We've grown so close working together the way we do. I can understand her wanting a family, though. How she can give up the generous salary and the benefits is beyond me. Cindy did talk to you about the salary, didn't she?"

"Not really," the older woman said, her voice trembling as her eyes darted back and forth from my face to where my hand was hidden.

"With someone of your limited experience, I'd have to start you in only the mid-thirties," I said, doing my best to appear saddened by the number. Laura wouldn't see $30,000 a year anywhere else though in this economy, I was certain of that. "But then there are certain benefits I enjoy offering."

"Like wh-what?" our applicant stuttered; though she tried to smile nervously to still seem friendly.

"Like a generous clothing allowance," I suggested. "My executive assistant has to project a certain image. In fact, I insist on picking out the finest wardrobe for her, especially at first, until she knows my tastes. At my own expense, of course."Laura nervously sipped her tea, saying nothing. She probably didn't know what was appropriate to say about that.