Never Too Late
by Chris Snow
Copyright
2011 by Chris Snow
Smashwords Edition
Author’s
Note:
All characters in this work of fiction are 18 years old or older.
Never
Too Late
Chapter 1 - Sam
I first noticed her when I was walking through the reception area on the way to my office. Normally I don’t make eye contact with the visitors who always seem to be waiting there to see someone. Maybe it was the fact that she was very attractive, and that she appeared very vulnerable as she glanced up from the magazine she was pretending to read. She looked at me, then dropped her eyes, then looked again. The second look was quick, a glance like a dog might give you when it is slinking away.
Now most women will look away when they feel a man’s eyes on them. They know that to look back for more than a moment is an invitation to be approached. Her second, furtive look indicated an interest, and nervousness. It intrigued me, grabbing my attention and making me look at her more carefully.
She was a well-dressed, middle-aged women, probably around 45 or 50. Her expensive-looking business suit and her general bearing signaled an upper middle class background. The open jacket to her suit revealed a pair of substantial breasts, which set high on her chest and greatly enhanced her femininity. It seemed to me that her blouse was a little tighter than it needed to be.
When I give a woman a second look I always check her legs and ankles. Slender calves and ankles whet my appetite for further exploration. This woman in her sheer stockings and four inch heels passed my inspection. I wondered what she was doing there.
My name is Sam, and I am the CEO and owner of my own advertising agency. I employee some twenty people—account executives, writers, artists, web site designers, and others—and we occupy two floors in a high rise office building in a large city. On this morning I had arrived as usual at about ten o’clock and was looking forward to interviewing a number of young ladies for the job as my personal assistant.
I had given specific instructions to Karen, my human resources manager, about the kind of person I wanted. My personal assistant had to be female, young, pretty, and above all accommodating to my every wish. Being rich and powerful meant little if you could not take advantage of the situation to indulge your passions. Karen was well aware of my sexual tastes, as she shared many of them. Her management position in my company was due in part to her willingness to play all sorts of sexual games with me.
The first thing I did on entering my corner office was to pick up the phone and call Karen. “Well, have you lined up some suitable applicants for me to interview today?”
“Well sir, I do have one that I think you will find interesting. In fact she is waiting in the lobby right now.”
So the woman I had noticed was here to apply for my job. That was interesting, but somewhat surprising.
“Karen, I told you I wanted a young, exceptionally pretty assistant. I need an attraction like that to help me sign up new accounts. Plus as you know I like having beautiful women around who are anxious to please me.”
“Trust me,” said Karen in a conspiratorial tone. “This woman is pretty enough, and I talked with her a long time. Under your guidance I think she will please both you and your prospective clients, and maybe me as well.”
Karen’s implications were clear. “Umm.. tell me more,” I said.
“Her name is Vicky. She was married to a successful businessman for twenty years and has never had to work. A month ago the guy ran off with his secretary. Vicky loves her large house and agreed to take the house in exchange for minimal alimony. Now she barely has enough money to buy food, let alone keep up the house.”
“So, another bad luck story. What makes her so suitable as my personal assistant?
Karen laughed. “You know me. I got her to talk about her sex life, or lack thereof. Her husband never cared about her fantasies or her pleasure. She is highly sexed and frustrated, but thinks of herself as a good girl who should not need sex. She also thinks she is too old and life has passed her by. When I told her it’s never too late to enjoy life, she just sighed.”
“I don’t want a prude for an assistant. Do you think she can be made to give up control?”
“Absolutely. I picked up on the signs; she is a latent submissive who is ripe for a strong man. You could be the one to break her in.”
That thought brought me to instant hardness. Karen knew me so well.
“Ah, you little vixen,” I said. “What makes you think she will submit to my outlandish tastes and behavior?”
“She is vulnerable—almost desperate. And I have laid the groundwork for you. I told her you would be a demanding, but fair boss, and if she were willing to obey you without question in all things you would take care of her and pay her well. When I said those things I could see her nipples get hard under her blouse.”
Now Karen really had my attention. “I saw her in the lobby,” I mused. “She does appear to have a good body.”
“You bet she does. I could find you a sweet young thing who might look and feel better, but she would probably be hung up on her own attractiveness and not ready to let herself go the way you want.”
“Why not?” I asked innocently. “You are a sexy, sweet young thing with a tight body and I can turn you into hot custard.”
“I’m not all that young anymore,” she laughed. “Remember my twenty-ninth birthday was last month. Besides I am an exception, and you got my number early on.”
“Yea, but you have a killer body. I’m getting hard just thinking about you.”
“Cool it big man. Go get Vicky and interview her. You can enjoy dominating her and still have me whenever you want.”
“Okay. You convinced me. But I may want you to talk to her after my interview.”
“No problem. I would enjoy that. Maybe I should stay late tonight so we can compare notes.”
“It’s a date,” I said and hung up. My heart was thumping in my chest as I straightened my pants and left my office to go get Vicky.
Chapter 2 – Vickie
I can’t believe I had opened up so much during that interview with Karen. She had such a non threatening way of asking direct questions, and I guess I just needed to talk to someone. In the last few months I had been so frustrated, sexually and every other way. No question Karen had plenty of sex in her life, given that body of hers.
It was really interesting the way she had seemed to empathize with my need to be in relationship with a strong man. That bastard I was married to for so long never treated me the way I craved. Mostly he did his own thing and let me do mine. I thought he had lost interest in sex completely, but then he ran off what that tart of a secretary. She’s probably all looks and no passion. To hell with them both.
After my interview with Karen I had this strange feeling of excitement in my stomach. When that good looking man gave me such a frank appraisal in the lobby I wanted him to seize me by the hair and take me to his cave. It was embarrassing; I had to look away.
What was the matter with me? I was there for an interview, not a BDSM session. These old fantasies of mine didn’t have a place in this business environment. Besides I thought I could never have acted on them anyway. I was an educated, sophisticated woman, not some man’s toy. It would have been so humiliating to be bossed around and made to do unspeakable things. Still…
I had to stop thinking about those things and get my mind back on preparing for the interview. My work experience was so thin, and I needed that job so badly. How was I going to convince the boss that I would be a good personal assistant?
Chapter 3 – Sam
I returned to the lobby and walked right up to her. “Hello Vickie. My name is Sam and I understand you are applying for the position of my personal assistant. Please follow me to my office so we can get acquainted.”
Vickie seemed surprised when I introduced myself as the one looking for a personal assistant. She obviously remembered me as the guy who had given her the once over earlier.
“Oh, yes sir. I am pleased to meet you,” she said as she rose and hurried after me. I walked rapidly down the hall to make her struggle to keep up. It was part of my plan to put her off balance and break through her prime and proper façade.
“Here we are,” I said, moving behind my desk. My office was huge and included a large, high table that I used to spread out brochures and ads we were working on. It had sturdy, chrome legs and a top of thick black glass. Several padded, adjustable height stools were pushed up against the table.
I spoke to Vickie. “Bring one of those stools over in front of my desk and take a seat. I like to see all of a person when I interview them, and my desk gets in the way when they sit in regular chairs.”
The use of the stool was one of Karen’s inspirations for conducting interviews of females. Climbing onto the stool invariably caused their hemlines to rise, usually well over their knees. The way a woman handled the situation said a lot. Some of them took advantage of the seemingly innocent opportunity to show off their legs; others were very uncomfortable and constantly squirming to pull their dress down. Vickie was in this latter category, but the way she did it ratcheted up the sexual tension in the room.
I began to question her. “Have you ever served as someone’s personal assistant before?”
“No sir, but I am willing to learn.”
“What type of office experience have you had?”
“Well sir, the truth is that I have just entered the job market. Up to this point I have been an old fashioned housewife.” She smiled as she tried to make light of her lack of qualifications. I liked the way she kept calling me “sir”.
“What do you think the duties of a personal assistant might be?” I asked.
Vickie squirmed again on the stool and pulled on her skirt. “I suppose it would be like a secretary, scheduling meetings, making travel arrangements, things like that.”
“Are you uncomfortable on that stool?”
“Oh no sir. It’s okay.”
“Then stop squirming and let your skirt settle where it will. You have quite nice legs you know.”
Her face reddened like a tomato in the summer sun, but she stopped moving. I could see her chest heave as she took a deep breath.
“As my personal assistant you would be doing the kinds of things you mentioned, but also quite a bit more. I want someone to help me entertain my good clients and close deals with new ones. Also, I have some personal needs that my assistant must attend to.”
“Oh ?”
“Yes, you would have to be available to work late and travel with me when necessary. Would that be a problem?”
“No, not a problem. As Karen probably told you, I am alone right now.”
“Did Karen also tell you that I require absolute obedience?”
Vickie’s eyes got wide and she shifted around again on the stool. “Yes, she did mention something about that. I wasn’t quite sure what she meant.”
“She meant that you must do anything I tell you – anything. Of course you could always quit whenever you wanted, but you would get no severance pay and a bad reference.”
“I see…” She was flustered and did not seem to know how to respond to the implications of what I was saying.
“Do you? I told you to stop squirming in your seat, and yet you did it again.”
“I didn’t realize…..”
“It’s really very simple. You listen and respond. I wanted to look at your legs and told you to hold still. Instead you tried again to pull your skirt down.”
She looked flustered and uncertain about what to do. “I don’t know if I’m ready for a job like this. This is a new situation for me.”
It was time to take the interview to the next level and see how far this woman was willing to go. If Karen had judged her correctly I would soon see some signs that she was sexually excited by the situation. I stood and walked over to a credenza that was against one wall. Leaning down I opened the sliding door and removed a black leather riding crop.
“This job as my personal assistant would pay you five times what you could get at any other job. But you would have to accept that even the slightest disobedience has its consequences.”
Vickie’s eyes never left the crop as I moved toward her, tapping the flexible leather against my leg. Slowly I circled her, as if I were trying to decide which part of her body should feel the sting. Finally I lifted the end and used it to trace a line down her spine to the top of her ass.
“Do you understand, Vickie?” I whispered in her ear.
She licked her lips. From the way she was breathing I knew she was turned on. “Yes sir, I understand.”
“Do you want the job?”
There was a long moment of hesitation. “Yes sir. I think I can handle it.”
“We shall see. There will be a thirty day trial period.” I rested the crop on her shoulder. “Open the jacket on your suit and push out your breasts.”
That was the moment of truth. There was no longer any doubt about what she would have to endure if she took the job. After taking another deep breath she shucked off the suit coat and arched her back. The jacket dropped to the floor. Her tits strained against the thin fabric of her blouse, protruding like an offering to appease an angry god.
I slid the crop under her chin and used it to lift her head so that she was forced to look at my eyes. “Are your breasts sensitive, Vickie?” I asked
“Ohhh…. yes… very…. please don’t hurt them…” Her words came out in little bursts.
The crop slowly descended from her neck, and then rose again as I let the leather flap on the end climb over one of her firm mounds. When it reached the peak I could feel the edge of the flap catch against a stiff nipple. Gently I sawed the leather back and forth, like a violinist playing a long note to tune the orchestra.
“OH MY….”
“Shoulders back and hold still!”
When I thought her nipple had grown and hardened as much as it was going to, I lowered the crop to rest on her knee, just below where her tight skirt was gripping her thighs. Then I inserted the little flap under the edge of her skirt and lifted.
“Are you wearing panties, Vickie?”
“Of course,” she said in a small voice.
“I hope you are not wearing panty hose. I dislike panty hose.”
Her face colored again. Having a man ask her about her underwear was not something she was used to. “Yes sir, I’m afraid I am. I always wear panty hose when I need stockings.”
“As long as you are working for me you will never wear them again. You either get stockings that stay up by themselves, or you wear a garter belt. Is that clear?”
For a moment her eyes flared with indignation. “I never…”
“Now take them off!”
“I beg your pardon…..”
“You heard me. Drop your skirt and take off your panty hose. Then put your high heels back on.”
“You’re not serious! Someone might come in.”
“Yes they might. Once you are my personal assistant that won’t matter. But since this is just an interview I will respect your concerns and lock the door.”
Her eyes followed me as I went to the door and turned the key. “There,” I said, putting the key in my pocket. “Now no one can get in….or out.”
I put special emphasis on the “or out” to let her know that she could not leave without my consent. It was important that she feel she had no choice but to submit to my whims. That sense of inevitability would help her let go and give free reign to the lust that I knew was bubbling just below the surface.
Still standing by the door I waited for her to obey my command. She seemed frozen to the stool, not quite ready to cross the line into submission and disrobe in my office. Her eyes dropped and she began to sob.
“I don’t know.. I don’t know… it’s too much……”
Angrily I crossed the room and slapped her across the cheek. “Get up and drop that skirt! I’ve had enough of your indecision.”
When I raised my hand again she quickly slid off of the stool and began working at the clasp at her waist. I pulled the stool back and sat on it myself, watching her face. Tears trickled down the pink skin where I had slapped her.
The skirt came open and rolled over her hips to lie in a pile at her feet. She stepped out of her shoes and shimmied the panty hose down her legs. Then, balancing on one foot at a time, she pulled off the stockings. Finally she slipped back into her high heels and stood facing me, a resigned look on her face.
It was as erotic a picture as I had ever seen. Her long bare legs disappeared up under her hanging blouse, which almost but not quite hid her bikini panties. My already stiff cock hardened until it was almost painful.
“Step away from the skirt and walk around the room,” I ordered, tapping the back leg of the stool with my crop.
This time she did not hesitate. “In for a penny, in for a pound,” she muttered under her breath as she paraded herself in front of me. She seemed proud of her body and its obvious effect on the hump in my pants. In her high heels she swayed and twisted, turning to give me a view of her from every angle. Her eyes were hot and focused on me and my reaction.
“I will be a good personal assistant for you,” she purred.
“Come here and stand in front of me,” I said. “That’s it. Now move your feet apart.”
She did as I instructed.
“Good,” I said. “Now put your hands behind your head.”
It was a position of total vulnerability and submission. Although her tits with their pointy nipples were covered by her blouse, the material was thin and the big melons were inches from my mouth and hands. There would be a time very soon when I was going to give those babies a good going over. For now, however, I wanted to draw out the process of her surrender.
I looked into her eyes. “Hold very still. I need to test your reactions.”
Slowly I brought the crop up between her legs, caressing first one thigh and then the other. As it went higher it lifted her blouse and revealed her panty-covered pussy, which I could swear seemed to be swelling in anticipation. A soft moan came from deep in her body.
“Ohhhh….”
“Vickie, you are a hopeless submissive. You need a man like me to take control of your body and make it sing.” The crop touched her pussy and the soft leather pressed into her.
“OHHH GODDDD…..”
I wanted to draw her out and make her admit her desires. “Have you ever felt this way before? Has a man ever made you submit to him totally?”
“Noo….. It’s not right…. Don’t make me do this.” She protested weakly, even as her rotating hips betrayed her. I twisted the crop and drew the edge of the flap between the lips of her pussy. Her eyes closed and the muscles in her ass began a rhythmic contraction. It was clear to me that another minute of this would put her over the top.
I withdrew the crop. “I am going to make you do whatever I want. You do understand this don’t you Vickie? If you take this job you will be mine to play with as I please. Your body has craved this for a long time. Now maintain that position.”
Sliding off the stool I walked behind her and studied the curve of her ass and legs. Her mature body had its soft, fleshy places, but on the whole it was toned and firm. I have always admired women like her with small, rounded buttocks, just big enough for one cheek to fit in a man’s hand. Vickie didn’t move as I cupped her and squeezed.
“Very nice,” I said. “It will be a pleasure to spank you when you are naughty.”
“Ahhh….,” she whined in a tone that indicated both excitement and acceptance.
“Now miss Vickie, it is time for you to decide. Should I call Karen and have her come sign you up as my personal assistant? You would begin tomorrow at a salary of $75,000 with full benefits. We could make it a 30 day trial. What do you say?”
I was facing her again and lifted her chin with my hand. Her body was shaking, crying for more stimulation from my hands and the crop. In her aroused condition there was no doubt about how she was going to decide.
“Yes,” she said in a small voice. “I need the job. I want the job. I will do as you say.”
“Good,” I said and went to the phone to call Karen.
Chapter 4 – Vickie
My god what was going on? In my wildest dreams I never imagined an interview like that! There I was, standing half naked in a man’s office after meeting him only half an hour before. I had fantasized about having an affair with an attractive boss, but this was crazy. He had almost made me cum a few minutes ago, and now he was calmly talking on the phone.
How did he know I would not scream and run out of his office? It must have been that bitch Karen—she had probably told him how desperate I was, and how horny. What was I supposed to do, for god’s sake?
Since my husband ran off with his slut secretary and for a long time before that I had been frustrated sexually. He never cared about my needs. For a while he would fuck me about once week, like he was carrying out his marital obligation, and it didn’t matter whether I came or not. In the past year we hardly had sex at all.
I had resorted to talking to online Dom's regarding my feelings and urges. They assured me that the feelings I had were the natural desires of a submissive woman. I found that I enjoyed chatting and reading stories about the so-called BDSM lifestyle. In general I am not a submissive person, but in the sexual arena I craved to be handled roughly and told what to do.
My conservative upbringing taught that thinking about sex was dirty and something good girls avoided. For me to pursue any sexual fantasies was out of the question. When I was young my father would discipline me by whipping me with his leather strap, after making me smell it. At other times I was made to kneel in the dark. I think now that these episodes re-enforced my submissive longings, as painful as they were at the time. The smell of a leather strap still makes me quiver.
When Sam explained the job to me I was instantly wet. Was I at last going to be able to finally experience all the things I had lusted for all those years? But I was also apprehensive about what was going to happen to me. I knew I would be degraded and used as a sex toy by Sam and have to do whatever he ordered me to. If I am honest with myself I have to admit that I wanted that very much.
The excitement I felt as he made me strip and then teased me with the crop was incredible. The thought of going in to work everyday and reporting to a boss like Sam both thrilled and frightened me. I knew he would probably make me play with other women, an idea that sometimes was revolting, and at other times strangely exciting.
I thought I was going mad at having those thoughts, but I knew that this was the opportunity to see if I was a really TRUE submissive. Sam seemed so sure of himself and his ability to dominate me. If anyone could do it, he would be the one to train me and propel me into the lifestyle I secretly craved.
All these thoughts rushed through me in the time it took him to get Karen on the phone and summon her to the office. By the time he had hung up I had resolved to obey him and not question anything he asked me to do.
Chapter 5 – Sam
With some effort I controlled my raging hard on and allowed Vickie to get dressed again in her skirt and jacket before Karen arrived.
“Come in, Karen. Vickie and I have had a good talk, and she has accepted my offer of employment as my personal assistant. I would like you to take her back to your office and complete all the paperwork. Her salary is to be $75,000 a year.”
Karen looked at Vickie and quickly sized up the situation. Vickie’s skin was still flushed and her eyes hot. Her posture and demeanor signaled her resignation to the conditions of her employment. Karen knew that I had broken Vickie’s feeble attempt to maintain her dignity and conceal her sexual needs.
“Wonderful,” said Karen. “I know you will like it here, Vickie. Come with me and we’ll take care of all the details. We can also chat some more and get to know each other better.”
“Good,” I said. “And Karen don’t forget about our meeting this evening at 6 pm in my office.”
She smiled. “I won’t forget.” Vickie followed her out of my office without saying a word.
The rest of the day I busied myself with little tasks, but my mind kept returning to the image of Vickie in her high heels and panties. I made a note to myself to send her to Victoria’s Secret with the company credit card to buy all kinds of sexy lingerie. I would speak with a friend who worked there to make sure Vickie was not conservative in her selections. What Vickie would be wearing under her office attire would be “Vickie’s Secret”, and mine.
At 5:30 I opened my office bar and poured myself a whisky. Then I uncorked a bottle of good Chardonnay to serve to my manager of human resources. Our evening conferences always seemed to go better when wine was available.
Promptly at six Karen knocked on my door. Everyone else had gone home, and I had phoned my wife to tell her I would be working late. “Come in Karen, and lock the door behind you,” I said.
“Yes boss. I am here as ordered.”
I handed her the glass of her favorite wine. “Let’s sit on the couch and you can tell me what you think of my new assistant.”
Karen sat and tucked her gorgeous legs under her. She was wearing a loose skirt and tailored blouse that hugged her firm young tits. How I got so lucky to have a good business and such a beautiful and willing subordinate I don’t know. Of course her willingness might be related to the fact that I paid her almost $200,000 a year.
“Sam, you have yourself a winner in Miss Vickie,” she began with a smile. “She was still so turned on when I got her back to my office I had to wipe her forehead with a damp cloth.”
“Really? I knew I had her going. If I had kept it up I could have made her cum. What did she say?”
“She was very embarrassed and suspected that I had told you enough about her to encourage you to treat her the way you did. But I got her to relax and see the bright side. She needs this job and realized it was best to find out quickly what she had to do to get it.”
“What did she say about the way I treated her?”
“That you dominated her completely and made it clear the job involved her sexual submission. She said she had never been so turned on in her life. She was raised to be a proper lady and never do wild and crazy things, but in ten minutes you broke her and brought out her sexual need to be bossed around.”
“She’s not like you,” I joked, “doing wild and crazy things all your life.”
“Like this you mean?” Giving me a sexy smile she put her hand on the bulge in my pants. Her fingers searched until they closed around my growing erection.
“Whoaa,” I laughed. “You’ve barely finished one glass of wine, and I haven’t heard all of what Vickie said.”
“Pour me another glass. But I’m going to take a hold of Mr. Happy again to see how you react to what I’m telling you.”
I got up and returned with the wine bottle, not bothering to try to hide my excitement.
“My what a big thing you have my dear,” she teased. “Why don’t you let it out so I can pay proper attention to it.?”
“No way…. not yet. But you can touch it through my pants if you want, while you talk to me.” I sat beside her and filled her glass. No sooner had I placed the bottle on the floor than she resumed her hold on my rigid cock. Taking small sips of wine she related her conversation with my new personal assistant.
“Vickie told me you had made her take her skirt and panty hose off. Is that true? If so you were taking a big risk that she would make trouble.”
“It’s true, but there wasn’t much risk. She was not an employee at that point. And I could tell she wanted to do it.”
Karen ran a long fingernail up and down the ridge in my pants. “Still, as your human resources manager I have to advise you to get something on her so she cannot complain in the future.”
“Good idea,” I said, trying to control my mounting excitement. “I want you to set up a three-way with you and me and her, and secretly film it. Then we can use to prove she is a willing participant if we have to. What else did she tell you?”
Leaning toward me, Karen whispered in my ear, and at the same time lowered her hand to where her fingernails could rake and tantalize my balls. “Vickie said that the combination of being humiliated and made to submit brought out feelings she did not know existed. She said that when you touched her with crop she thought she would explode. Her pussy was soaking and she kept expecting you to lay her out on that big glass table and fuck her. Why didn’t you?”
“I wanted to torment her and prolong the process. It will be all the sweeter when she is forced to beg for it. Also, I want her to experience some physical pain first, so that she is thoroughly cowed and will submit to anything.”
“What do you plan to do to her?”
“The next time I am going to explore those big tits. I may tie them and torture them a while before I make her cum and then fuck her.”
“Ummmm…. I have such a naughty boss,” said Karen as she squeezed and pulled on my cock. “Where do you get such ideas?”
With uncanny accuracy I reached over and closed my fingers on her nipple through her blouse. Her eyes popped wide open as I twisted and squeezed. “This is just a sample,” I snarled. “After I put clamps on her buds I will whip the sides of her tits with the tip of my belt.”
Karen liked her sex rough, and she was immediately turned on by the image of my torturing Vickie. She lay back on the couch and opened her legs, still gripping my cock. “What else are you going to do to her?”
I pulled Karen’s nipple out from her body. “I have a little suction device that I’m going to put on her nipple. It will suck and stretch her flesh to twice its normal size. Then I will roll it between my fingers and nibble on it with my teeth, like this….” My mouth came down and nipped her through her blouse.
“Ohhhh… I want to see it…. Can I be there?? … Ohh shiitt that feels good….”
“Why do you want to be there?” I teased.
“I have things I want to do to her too.”
My hand began a journey under the loose skirt that had ridden up her legs. Knowing Karen there would probably be no panties in my way.
“What do you want to do to her?” I asked sweetly.
“I want to show her how good it feels to have a woman lick her pussy. She told me she had never been with a woman before. I know just how to drive her crazy with lust.”
“Merely by using your beautiful mouth?”
“No, I have a favorite vibrating toy that I would shove up her ass at the same time.”
“Like this?” My finger had found her bare pussy and was wet with her juices. Slowly I moved it a little further and began to ease it up into her ass. She bucked like a spurred horse and squealed with pleasure.
“YESSS…. God you make me so hot…..”
I was tired of fooling around. Between Vickie and Karen I had almost, but not quite, cum ten times that day. “Get out of those clothes Karen,” I ordered. “I’m ready to fuck.”
She needed no urging. In less than a minute she was naked, standing by the couch and undulating her fabulous body in front of me. I picked her up under her ass and hugged her to me as I carried her over to the big table.
“Sit your ass down on the glass while I get rid of my pants.”
“Ooooo… it’s so smooth and cool….”
“Shut up and raise your knees…”
I am a tall guy, and the angle was perfect for entering her. She was easy and tight and warm and cool all at the same time. That first thrust was the most delicious. I leaned back and watched her tits bounce as she humped me, driving herself toward an early climax. Karen is the most multi orgasmic woman I have ever known, and every one always seems more intense than the last.
“Fuck me you big bastard…” she screeched. “I’m ready for number two already and I’m going to squeeze it out of you.”
That did it for me. I grabbed a tit and ploughed into her, driving her across the glass and then pulling her back again for more. Her pussy milked me to an ecstatic climax.
“You’re incredible,” I said when I got my breath.
“I like you too,” she laughed. “Now when are we going to break in your new assistant?”
“Tomorrow night, same time, same place,” I said.
Chapter 6 – Vickie
After I left Karen’s office I somehow found my way to the elevator and punched the button for the parking garage where I had left my car. I was in a daze, still sexually aroused, but incredulous at the situation. Karen had encouraged me to go with flow and be honest about my sexuality. I had signed all the papers and was now officially Sam’s personal assistant.
When I reached my car there was no one around. I unlocked it and slipped in to the soft leather seat. As I maneuvered into driving position the edge of the seat rubbed against my pussy and set me off again. I was craving release from the incredible sexual tension. Before I knew it my hand was under my skirt and pulling aside the edge of my soaked panties. It felt so gooood….
“Ahhhhh……” It took only a few seconds of direct clitoral stimulation to make me cum. I bounced on the seat and leaned my head into the steering wheel.
I think I must have blacked out for a few seconds, because when I looked up I saw a man getting into the car next to mine. He gave me a strange look but backed out quickly and was gone. What had he seen? I felt I was totally out of control.
Alone again I closed my eyes and began replaying my interview with Karen. Why had I been compelled to give her so much information about my sexual desires and my lack of sex with my ex husband? Karen had obviously told Sam, and he had used that knowledge to manipulate me. He had made it clear that if I took the job I would be his plaything, doing anything he ordered in addition to my routine job functions.
My stomach started to wretch and I barely swung the door open in time to direct my puke on the floor of the garage instead in my car. My conflicting emotions had literally made me sick. The turn of events in my life had brought me to a point where I had lost my moorings. I was like a boat cast off in a rough sea, with no pilot at the helm.
But what could I do? I was shaking uncontrollably as I told myself that my need for money had to outweigh my concerns about what Sam might make me do. Yet I was aware in my gut that it wasn’t only the money, and that I needed what Sam could give me. I would go through with the 30 day trial period and see what happened.
Gradually my shaking subsided and I was able to start the car. There were things I had to do to get ready for my first day of work. Number one was to get rid of all my panty hose and buy some garter belts and stockings. I had just enough money left on my credit card to be able to do that. It was a good thing that aside from the panty hose, which I had never liked anyway, Sam had seemed pleased with my general appearance, and I had plenty of other similar clothing that would be suitable for wearing to the office. Money for shopping had been no object with my philandering husband.
My dresses and suits were all exquisitely tailored to outline every curve of my body. Since my breasts were my best asset I always had my blouses made a little tighter than normal. With the right bra I had no trouble attracting male attention. Remembering how Sam had made me strip in his office, I resolved to buy a good selection of sexy bra and panty sets.
Feeling considerably better I drove out of the garage and headed for my favorite department store.
Chapter 7 – Sam
I was looking forward to my first day with my new personal assistant. As I left my home in the suburbs I told my wife I would be working late again that night. She had long since lost interest in sex, and she seemed content with spending my money and letting me work whatever hours I wanted. If she suspected I had other women, she kept it to herself.
What tasks should I give to Vickie on her first day? I remembered that George Stockwell, one of my best clients, was coming to town the end of the week and bringing his new trophy wife. This guy paid my company tens of thousands every year and expected to be entertained. Knowing George, he would want some exciting female company. It would be interesting to meet his new wife.
George always enjoyed a party atmosphere and he liked luxurious, exclusive settings. I would have Vickie arrange for an overnight cruise on a private yacht along the Florida shoreline. Vickie would manage everything and come along as the hostess. I might as well find out right away if she was up to the demands of the job.
Of course, right from the first I would have to continue with her training to please me sexually. And at the end of her first day she would be subjected to my planned three-some with Karen. Miss Vickie was going to have an eventful day.
Chapter 8 – Vickie
Dressing for my new job that first morning my mind was racing and butterflies were fluttering in my stomach. The last thing I wanted to do was throw up again, and I fought back the panic. If I could just let my sexual feelings over power the little voice in my head that kept telling me to run I would be all right. As excited as I was, that shouldn’t be too hard.
I put on my new garter belt and attached the silky hose that caressed my legs. When I stepped into my 5 inch designer heels and looked at myself in the mirror I had to smile. This conservative, forty year old was being transformed into a sex goddess. My nipples started to stiffen as I tucked my breasts into a white silk bra and then slid a flesh hugging white lace camisole over my head. The combination shaped my tits into turrets that I knew would be outlined against the tight jacket of my business suit.
For a moment I considered going without any panties at all, but decided that would be too brazen. Better to let Sam make me take them off, or do it himself. A shudder went through me as I pulled up the white silk thong I had bought to go with the bra.
A black silk, knee length skirt and jacket completed my outfit. My long hair I coiled and packed on the top of my head, leaving visible a couple of silver pins that if pulled would release the thick tresses in the time-honored way that women have offered themselves to men. A little light makeup and I was ready to make my debut. I felt sexy and was confident that Sam would approve of his new personal assistant.
As I drove into the city my excitement grew with each mile. I tried not to dwell on what Sam did to me during that first interview, but I could not get the feel or smell of the leather crop out of my mind. Would he use it on me again this morning? The thought made my nipples swell against the camisole.
Finally I turned into the parking garage. Another car had gone in just ahead of me, and I parked along side. When I looked over I was surprised to see Karen getting out. She walked around the back of her car and waited for me as I opened my door. I swung my legs out, unable to keep my skirt from sliding up over my thighs and exposing the tops of my silky hose.
“Hi,” she said with a knowing smile. “Nice outfit. Where did you set that sexy garter belt?”
I was mortified. My skirt must have gone up higher than I thought. “Oh, it’s just something I picked up.”
Karen laughed. “Don’t let Sam see it or you will be on your back on that glass table before you have time for coffee.”
“Ha, ha,” I replied lightly. Although she had said it as a joke, I had the feeling that it could be true.
“Come with me,” she said. “I’ll take you to his office and get you started. He’s probably already there.”
I followed her, but after what happened yesterday I was leery of engaging in any conversation. It was clear that anything I said to her was going to be passed on to my boss.
Chapter 9 – Sam
Normally the first thing I do when I arrive at my office is make myself a cup of coffee. Now that I had a personal assistant, however, I would teach her to have a cup ready for me. On this her first day I would start the coffee, but not drink it until she arrived to serve it to me.
In a few minutes I heard Karen and Vickie coming down the hall toward my office. In a flash of inspiration I quickly retrieved the crop from the credenza and placed it across the top of my desk. I wanted to create the right atmosphere for Vickie’s arrival.
Karen knocked on my door and opened it. “Good morning Sam. I met your new assistant in the parking garage and have brought her to you.”
“Thank you Karen. I will take care of her from here. Come in Vickie.”
With an evil grin Karen dropped her eyes to indicate I should check out Vickie’s stockings. Then she turned and left. “See you later,” she said cheerfully.
Vickie stood in front of me smiling nervously. “Good morning, Sir,” she said.
Reaching out I took hold of her hand. “Good morning, Vickie. Welcome to my company.” I could feel the tension in her body, and she trembled slightly, as if my touch were electric. Good, she was just anxious enough to make conquering her a pleasure.
I took a step back and spoke sternly. “Please stand still so I can inspect you. Appearances are very important in our business, and I will check you over every morning to make sure your attire and demeanor are impeccable. No matter what your assignment is for the day, you are to come to my office first thing to be inspected, and to make my coffee, which is to be ready promptly at 9 am.”
“Yes Sir,” she said.
She was off balance and I wanted to keep her that way. I relished the power I had over her and the way she reacted to my manner. Continuing in a harsh tone I warned her about displeasing me.
“Any error in how you present yourself will be dealt with swiftly and painfully. Do you understand?” As I said those words I turned and looked at the crop on my desk. Vickie followed my eyes and gasped. I saw a rustle in her skirt as she reflexively clenched her thighs together.
“Now for the first few days, until I can be sure you have learned to wear the right underwear, I will require that you take off your skirt and jacket, just as you did in the interview. I trust you are not wearing panty hose again.”
“Oh no Sir,” she said quickly.
“Well then get on with it.” I picked the crop up off of my desk and sat on one of the stools. “And you can leave your clothes off while you make the coffee.”
Her face was flushed and her chest heaved as my words sunk in. She seemed paralyzed.
I tapped the crop on my leg. “I’m waiting,” I said.
Chapter 10 – Vickie
The tapping of the crop was like the clock ticking in the old Gary Cooper movie “High Noon.” Even though I had expected something like this, it was still so foreign to my experience that I held back. I was literally trembling.
Sam seemed in no hurry. It was like he wanted to make me cross the threshold on my own. Then I would be fully committed. This would be the first day of the rest of my life under his command.
Finally I found my voice. “Can you please lock the door first?”
“No.”
“No?”
“I said, No !”
“But… but…..”
“Yes, someone might come in, but it won’t matter. You are now my personal assistant, and the other employees are soon going to know the nature of your job. We have few secrets here.”
“Do the other executives do things like this in their offices?”
“Of course. We are known for our ultra liberal atmosphere. It’s one of the reasons we are so successful in signing up new clients. Now take off those clothes before I get mad.”
The crop slapped against the leg of his stool in a way that sent an unambiguous signal. If I did not get with the program I was going to suffer. I inhaled deeply and resigned to give it my best shot. My jacket, skirt, and lace camisole soon lay in a heap on the floor. Standing before him I hoped he liked my lingerie. He looked me over but didn’t say anything.
To cover my embarrassment I tried to act like everything was normal. “How would you like your coffee Sir?”
“Black. I made it for you this morning, but from now on you get here earlier and have it ready.”
“Yes Sir.”
As I turned to the coffee machine on the credenza I caught a glimpse of a smile cross his lips. I moved slowly, giving him a good look at my nearly naked body. When I had filled his cup and started back toward him, the smile was gone, replaced by as powerful a look of lust as I have ever seen. Just looking into his eyes made me weak in the knees. I leaned forward to hand him the cup and deliberately hung my tits in front of his face. Surely he would grab me and pull me into his lap.
Instead he leaned back and sipped on the coffee. “Thank you Vickie.”
I stood before him like a supplicant slave girl, not knowing what to say or do next. My heart was pounding. He continued to sip his coffee and move his hot eyes over my body. It was clear he would act when he was good and ready; my uncomfortable situation didn’t matter. Or maybe he wanted to prolong it.
Suddenly he put his cup on the floor and stood. The crop appeared in his hand and extended toward me, the little flap just touching the point of one breast. The sensual smell of the oiled leather was over powering. He raised the crop and traced the curve of my tits through the bra until the flap arrived at the other nipple. My chest heaved as I tried to press my nipple against the leather tormentor.
“Please…….”
“Please what?” he asked as he walked around me, dragging the crop over my shoulders and down my spine. When it reached the top of my ass he let it go lower, right into the valley between my cheeks, inching ever so slowly downward toward my pussy. “Please stop, or please continue?”
It took all my will power to remain still. My pussy was completely soaked, and I was hoping he wouldn’t touch me there and see what he had already done to me. “I… oh god… please don’t tease me any more ….”
Grabbing my arm he spun me around so we were facing each other, inches apart. Then he dropped the crop and put both hands on my ass, pulling me against the hard rod in his pants. “You’re lucky I even want to tease you, considering your ugly old lady underwear. Just because you are wearing a thong does not make it sexy. It has no style. And your bra covers too much and is so stiff I can barely feel your nipples, even though I know they are hard as marbles.”
It was true. My nipples were like stone pebbles and my pussy was soaking. His big hand slipped under the back strap of my bra and jerked until it broke free. Then he did the same thing to the thin bands of my thong.
“We will be getting you some more appropriate undergarments,” he growled as he pushed me back and lifted the torn lingerie from my body. Except for my garter belt, stockings, and heels, I was now naked. He looked me over like he was appraising a painting in a gallery.
“Very nice. Beautiful breasts and ample hips, not too big. I am going to enjoy you, starting now. Get over there and lie across my desk.”
When I hesitated he stooped and picked up the crop. As fast as I could I moved toward the desk, but still he caught my ass with two sharp blows. As my thighs hit the edge of the heavy, wooden desk, I felt his hand on my back bending me over. His voice was horse with desire.
“Grab the far edge and hang on. Good… Now spread your legs…”
It is difficult to describe how I felt at that moment. I could picture the lewd spectacle I was making, my bare ass up in the air hanging off the edge of my boss’s desk. With my thighs open the damp hairs on my pussy would be glistening at him in open invitation. My ass stung from where he had spanked me. I was embarrassed and humiliated, but also as turned on as I have ever been.
He ran his fingers lightly over my exposed pussy and taunted me. “You need this, don’t you Vickie?” I heard the unmistakable sound of a zipper being opened.
“Ohh……”, was all I could manage.
“Tell me what you want, Vickie.”
“Goddddd……. ahhhhh… you know…. don’t make me say it….”
“Say it bitch!”
I was broken. There was no point in denying him. “I want your cock in me…. fuck me…… pleassssse.. fuck me NOW..”
His attack was so sudden and powerful that I could hardly catch my breath. The first stroke opened me like pealed fruit, and the second reached deep into my gut. After the third I was close to orgasm, shaking and pushing back against him. His mouth was against my ear.
“No,” he growled. “You don’t get to cum unless I give you permission. I want to keep you on edge all day. Now use your pussy muscles to milk me. I am very close.”
“Pleassssseee..”, I moaned, desperate for release.
A hand closed on one breast, pinching the nipple cruelly. “I told you to squeeze me,” he whispered.
Without my even thinking about it my pussy spasmed on his cock. It was like he had direct control over that part of my body. The pressure set him off, and I felt a gusher erupt into me. He moaned, kissing my ear and cheek. I wanted so badly to cum, but he pulled out and left me just below the peak.
“Not bad,” he said, still breathing heavily. “You have a nice tight pussy.”
He walked around the desk until his wet cock was hanging in front of my face. Wrapping his hand in my hair, he pulled me toward him. The odor of sex stimulated my juices even more.
“Now look at the mess you’ve made,” he said. “I don’t want any of this on my pants. Use your mouth to clean me.”
I did as he ordered, enjoying hearing the little sounds of pleasure come from his throat. The taste of him kept my blood boiling. But after a minute he seemed satisfied and eased his cock back in his pants.
“Very good, Vickie,” he said. “I wanted you to have an energy drink to start your day. Now get dressed. I am sending you shopping.”
With that he picked up my torn thong and bra and threw them in the waste basket. I was just starting to get up off the desk when he picked up the phone and dialed a number from memory.
Chapter 11 – Sam
Looking down at Vickie as she licked my cock clean I couldn’t help feeling pleased with myself for choosing such a perfect personal assistant. I had expected some hesitation this morning, and was pleasantly surprised at her reactions. I may just have to feed her a breakfast energy drink every morning.
But that underwear was terrible. I had to teach her to stop thinking of herself as a middle-aged woman, and more like a vamp. My friend Ginger at Ginger’s Secret was just the person to help me do that.
As I dialed Ginger’s private line I enjoyed watching Vickie slip her camisole over her head and then struggle into her business suit, minus any other under garments. Ginger would be amused when I sent her a customer dressed liked that.
“When you are dressed, go sit on the stool,” I said to Vickie as Ginger’s line was ringing. “Keep your skirt raised so I can see your legs.”
Ginger answered after the fourth ring. “Hello, Ginger speaking,” she said in her sultry voice. Only her best private clients had this number. “How might I serve you today?”
I laughed at her suggestive tone. “Hello my dear. This is Sam, and I have a new customer for you.”
“Sam! It is so good to hear from you. I thought you had forgotten about me. It has been ages since you sent one of your special friends to see me.”
“No way I would ever forget you and your services,” I said cheerily. “After my friends visit you they come back much improved, in both appearance and attitude.”
“That’s my job,” she chirped. “Who do you have for me this time?”
“Her name is Vicky, and she is my new personal assistant. She will be involved in entertaining me and my clients, and I want her to look good in all situations.” Saying this I scanned Vicky up and down and gave her wink. In response she squirmed on the stool and stuck out her tongue at me. She was really getting into the spirit of things.
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