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 ...
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 threesome 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. Ginger replied in her usual straightforward way. “What kind of body are you sending me to work with?” I was glad Vickie could not hear Ginger’s end of the conversation. It might have put her off. “You will have no problem there,” I said. “She is a little older than the others, but she has all the right assets.” “Any special requests?” “You know what I like. Make what she wears a sexy surprise under her conservative business clothes.” “No problem. When is she coming?” “She’ll be there in half an hour. You have a $2,000 budget. Spend it all.” “Yum.” “Bye for now,” I said and hung up the phone. At the mention of the budget for just lingerie, Vickie’s eyes lit up. “That’s very generous Sir,” she said. “Go now. I want you back by lunch time, as I have an important assignment for you this afternoon. And don’t give Ginger any problems or you will suffer the consequences. Understood?” “Yes Sir.” Chapter 12 – Vickie I couldn’t believe what happened that morning! What a way to start a new job! I wondered if he was going to fuck me make me suck his cock every morning. As I slid off of the stool I was aware of the continued dampness on my bare pussy. I thought of what I had done the day before in the parking garage. It was exciting that Sam wanted me to have erotic lingerie to please him and his clients, but I hoped he was not going to make me service his clients the way I had to service him. Heading to my car I could not help but feel excited as the cool air wafted over my warm, damp pussy. With no panties on to soak up my juices I would have to resort to using a paper towel to wipe myself dry. I certainly could not go into Ginger's Secret and let Ginger see me dripping. It took me only twenty minutes to drive across town to the store. I checked my watch to make sure I got back by lunch time. As I walked into the store there was bubbly, voluptuous Ginger waiting for me.
“Hi there. You must be Vickie. I’m Ginger.” Ginger was very attractive and super friendly. With her young, lush body she could be a lingerie model. I suddenly felt very old. But then I remembered that Ginger knew my boss had sent me to buy underwear to please him, and I was embarrassed. “Hello Ginger. This must seem like a strange situation to you.” She laughed. “Not at all. My best customers are men with charge accounts who send their women to see me. Any woman who doesn’t take advantage of that is crazy.” “I’m not sure exactly what he wants me to buy.” “Leave that to me,” said Ginger. “I have already laid out some items for you to try on. It’s important to get the size right.” Taking my arm Ginger led me to a large dressing room at the back of the store. Several young clerks smiled at us as we passed them, making my face even redder. “Here we are,” she said. “I’ll lock the door so we won’t be disturbed. Now take off all your clothes except for your stockings and heels, and we can begin. I understand you have to be back on the job by noon.” I was surprised that Ginger was staying in the room with me. Looking around I searched for a door or curtain to a private cubicle where I could try on things, but there was none. Instead there was a low platform in the middle of the room, and beside it an upholstered arm chair, which is where Ginger settled herself. Many pieces of lingerie were scattered on top of a long wooden table against one wall. “Could I please have some privacy while I try these things on?” I asked. “Sorry dear. Store policy is that a sales clerk must be present. You would not believe how many of our expensive pieces get stolen by women if we leave them alone. Sometimes women will come in wearing no under garments under their clothes, and then leave wearing our best stuff. It’s incredible.” Now I was really embarrassed. I could not take off my clothes and reveal that I was like those women. “You don’t have to worry about me stealing anything. Now please leave. I have never undressed in front of another woman.” Ginger’s face took on a hard appearance. “Do I have to call Sam and tell him you think you are too special to abide by store policy? Other women he has sent have had no problem. Knowing Sam, you will be in big trouble.” She was right. Sam would not be pleased to hear complaints from Ginger. I had no choice. “Oh all right,” I said. “But I am not like those other women—the ones who come in to steal things.” As nonchalantly as I could manage I began taking off my clothes. Ginger sat silently, watching me with a satisfied look on her face. When it became obvious that I was wearing neither bra nor panties, her eyes opened wide. “Well, I see why you didn’t want me here,” she smirked. My face was very red. “It’s not what you think. Sam made me throw away my old underwear.” “Good for Sam. You have a great body and we are going to fit you in things to show it off properly.” She pointed to my garter belt and hose. “Take those off too. I want to outfit you totally in our garments. After all, we have to spend $2,000.” For the next hour I tried on endless combinations of the sexiest lingerie I had ever seen. There wasn’t one bra that covered half as much as my old one – the one Sam had
ripped off of me. Ginger had brought in items of various sizes and made sure I selected the ones that fit properly. The materials were of the finest silk, with each outfit more beautiful and sexy than the last. When I had put on the last set, a filmy blue half bra with matching thong, Ginger got up from her chair and walked up to the edge of the platform. “You are a beautiful mature woman,” she said. I did not like the lustful look in her eyes. “Thank you,” I mumbled and started to step down. “Wait,” she said. “I am not sure this outfit is the proper size.” One hand went to the cleavage between my breasts and the other started sliding down my lower stomach. “No,” I said and pushed her hands away. “Everything fits just fine.” Her eyes flashed. “As you wish,” she said sharply. “I just hope that Sam agrees. Take off those items you are wearing so I can pack everything up and prepare the bill.” “I would like to wear these last pieces so that I can go back to work feeling dressed.” “Sorry,” she said in a tone that indicated she was getting even. “Store policy is that I must pack everything. You must leave the way you came in.” She left and I got dressed. Ten minutes later I picked up my packages and went back to my car. Unbeknownst to me Ginger had immediately picked up the phone and called Sam, because when I got back to Sam’s office he was waiting for me with an angry look on this face. Chapter 13 – Sam I knew when Vickie left that she would come back with some very enticing lingerie to entertain both me and my clients. I could always count on Ginger knowing my taste. Sitting back and looking out the big windows in my penthouse office I planned the rest of my day with Vickie in mind. I managed to do a little useful work, and the morning went quickly. It was almost noon when Ginger called to tell me that Vickie had pushed Ginger’s hands away when she was trying to check the fit of some items. I knew that Ginger was bisexual, but that did not matter. I had specifically told Vickie not to give Ginger any trouble. That kind of disobedience had to be dealt with severely, and right away. It was obvious that Vickie had not been fully broken in yet. When Vickie came into my office I was sitting on the stool waiting for her. “How did things go with Ginger?” I asked. “Very well,” she replied. “I think you will be pleased with what I bought.” “That’s not what I heard,” I said with a scowl. “Come here and look at me.” Vickie looked alarmed, but came and stood before me. “What do you mean?” I stood and grabbed her by the hair, bending her neck back. “I’ll ask you again. How did things go with Ginger?” All at once it seemed to dawn on her. “Did that bitch call you and tell you I had pushed her away when she started caressing me?”
“She’s not a bitch; she’s my friend. And I told you to obey her. You are to follow my instructions whether I am with you or not.” I pulled harder on her hair, and her eyes started to water. “I’m sorry Sam…. she was getting fresh…. you didn’t tell me I was supposed to have sex with her. I have never been with a woman before.” “When I tell you to obey someone that means you do whatever they want. You have to be taught a lesson. Now get out of those clothes again.” I felt myself getting hard. The fact that she had never been with a woman was going to make for an interesting evening with Karen. “Please Sam, I have been naked more than I’ve been dressed today.” I had to laugh at that. But I was determined not to tolerate her disobedience. I wanted her under my thumb completely, no matter how many times I had to strip her in my office. And this time she was really going to understand about consequences. “Strip,” I ordered, pushing her away. “Show me some of that new expensive underwear.” Vickie looked stricken. She was sobbing softly as she slowly began removing her clothes. I was surprised to see that she was still naked under her skirt and camisole. “You are such a slut,” I said. “Ginger would not let me wear the new things out of the store,” she whimpered. “No matter. You can put some on when I am finished with you.” In another minute she was in her stockings and heels and nothing else, clearly apprehensive as I looked her over with fire in my eyes. “Go over to the credenza and pick one of the paddles. You have a choice of a wooden one, or a leather one. And don’t bend your knees when you are looking for them.” I have always found it very satisfying to make your victim bring you the instrument of their punishment. It adds to their humiliation and submission. In this case it had the added benefit of requiring Vickie to bend over with her ass in the air as she searched in the low cabinet. My collection of sex toys includes two special paddles that I had purchased on line. One was solid oak in the shape of an enlarged ping pong paddle. The other was basically a short leather strap attached to a wooden handle. Numerous holes the size of a quarter were located throughout the strap. Vickie wisely chose this one, knowing that the flexibility would lessen the pain. “Go stand by the window,” I ordered, “down at the end.” My office is on a corner of the building, high up, with large windows on two sides. There are metal slat curtains that can be closed to keep out the sun, but that day the curtains were pulled to the sides. The windows go almost all the way to the floor, except for a radiator grill that runs along the base, about a foot high. It was summertime, and the radiators were off. “Face the end window, bend over, and put your hands on top of the radiator. Don’t move your hands, no matter what.” Vickie was resigned to her fate and did as I instructed. Her ass came up and presented a perfect target. At the same time her big tits hung below her, swinging slowly back and forth as she squirmed in anticipation. Her position in the corner windows exposed her profile on one side and her tearful face on the other. I wondered if any of my neighbors in the adjoining skyscrapers would be watching.
SLAPPP…. My first swing of the leather paddle caught her squarely in the middle of her ass. It was a hard spank that I knew would get her attention. “OHHH….. THAT REALLY HURT…..” “It was supposed to. Now listen to me. The length and severity of your punishment will depend on how well you take it and your attitude. You are not to move or resist. If necessary I can tie you to the window with the cords on the curtains.” “Yes sir….” Before resuming I teased the reddened skin on her ass with my fingernails. Then I began a systematic spanking of her ass cheeks and upper thighs—not too hard, but with enough force so that each blow stung sharply. Slapp… Whapp…. Slapp… WHAAP… SLAPP……. “Ohhhh…. goddddd….. ahhhh…. whaaaaa……” Vickie cried and twisted and squirmed, but she held her position. I paused. “What are you learning?” “OHHH… I am learning to do what you tell me… I promise…. I have learned.” “Spread your legs.” She did and my hand dipped to feel her wetness. “I think your lesson needs reinforcement.” Just then my cell phone started vibrating in my pocket. I retrieved it with my free hand, while with the other I maneuvered the smooth leather of the paddle around between her legs. She moaned and rotated her hips, probably trying to get me to stop the punishment and fuck her. “Hello,” I said into the phone. The caller was a friend of mine whose office was on the same floor in the building next door. He told me he was enjoying the show I was putting on in my window. It was a good opportunity to increase Vickie’s humiliation. “Yes Charlie. I’m glad you happen to be looking out your window. I have this new personal assistant who needs to be taught the importance of obedience.” Charlie and I had similar tastes and had often partied together. From the tone of his voice I knew he was excited by the idea that I had a new employee who could be abused in this way. He was hoping to be invited to participate. I egged him on to further torment Vickie. “By all means, Charlie. Have your secretary bring your binoculars. I am not through yet. What’s that? You want me to spank those hanging tits? But Charlie, that would hurt terribly, don’t you think?” Now Vickie was really squirming. She knew how vulnerable her tits were in her position. I teased her by tapping them with the paddle and letting a nipple stick through one of the holes in the leather. By moving the paddle sideways I could agitate her nipple against the lining of the hole. “OH GOD Sam… I’ll be good….I really will…..please don’t do this to me in the window in front of the whole world…..” I ignored her and continued my conversation with Charlie. “Charlie, why don’t you call Phil and tell him what’s going on? His office is directly under yours and he could see just as well….. okay, bye for now, we’ll get together soon.” Vickie clearly had not learned her lesson. She persisted in telling me what she wanted and didn’t want. It was going to take many sessions for her to realize that she should be concerned only for my pleasure. If I wanted to show her off in the window, she should not protest. The fact that she did gave me an excuse to punish her more, and
do it in front of Charlie and Phil, and who knows who else. At the very least, Charlie’s secretary was watching. Chapter 14 – Vickie Why had I rebuffed Ginger’s advances? That was stupid. I should have known she would be like Karen and tell Sam everything. Sooner or later I was going to have to submit to a woman anyway. I had brought this punishment on myself. Overhearing the phone conversation and knowing I was being watched by both men and women was so embarrassing. And any hope that my spanking would end soon was dashed with Sam’s next words. “So you don’t like being put in the window. Too bad. Now that I know we have an audience, I think we should give them a better show. Stand up and face the glass.” Before I knew it Sam had raised my arms and tied my wrists to the curtain cords on either side of the big pane of glass. “Now spread your legs and press your toes into the vents in the radiator grill. That’s it. Perfect.” I was stretched in front of the window like an animal skin, facing outside for all to see. Except for my stockings and heels I was completely naked. Sam pushed me in the back and my tits flattened against the cool glass. Looking down I could see little figures on the sidewalk. I was terrified of falling through the glass. “Sam, please let me down….. I’m scared of crashing through the window.” His answer was to rain a series of hard slaps on my ass with the leather paddle. Every time I knew one was coming I tried to lessen the sting by pushing my hips forward, which of course pressed me against the window. “Ohhhh….. arrrrrwww……” “Did I not tell you before you accepted this job that any disobedience would be dealt with swiftly and painfully?” “Yes Sir… I am sorry Sir….” “You are now going to get twenty spanks, and you are to count each one and thank me for correcting you.” SMACK “One…. thank you Sir.” SMACK “Two… thank you Sir.” I kept up the count and tried not to press against the glass. My stomach was churning from looking down from that dizzying height. After the tenth spank I clenched my eyes tightly shut. I was trembling. Sam would not have it. “Open your eyes, Vickie. Look at the buildings across the way and see if you see anyone watching you.” Looking up I could see groups of people at several of the windows in the closest building. “Ohh.. nooooo….” “You like it Vickie. Your nipples are hard as rocks, and your pussy has smeared stuff all over the glass.”
It was true. I was turned on by the whole scene. As I counted out the remaining spanks I realized I was close to orgasm. If Sam had put that leather up between my legs it would have been all over. But he stopped and whispered in my ear. “Are you ready to abide by the rules of your employment?” “Yes Sir. I will do anything and everything that you want. Just please let me get away from this window. I am so dizzy.” “OK, I will untie you. But the first thing you have to do is clean my window… using your tongue.” Oh, the humiliation! Sam kept coming up with things to degrade me. Why was it that with each new abomination I felt a fresh wave of excitement? He released my wrists, and I bent over to put my mouth on the glass where I had wet it with my juices. The view looking down sent adrenalin rushing through my veins. I closed my eyes and licked. “Good girl,” he said as he patted my sore ass like I was his pet dog. Chapter 15 – Sam Spanking Vickie in the window was very exciting, and I was ready to lay her out on my desk and fuck her again. But there was work to be done. I couldn’t spend the entire day playing. “That’s enough. You can get dressed now. And put on some underwear for god’s sake. It’s time for you to so some real work and get busy making arrangements for George Stockwell’s visit.” “My new undies are still my car,” she whined. “Well,” I laughed, “you can get them when you go to lunch. In the meantime put your clothes back on so I can think about something other than fucking you.” “Yes Sir,” she said and hurried to pick up her clothes from the floor. I noted how glad she was to be away from the window. Since she was so uncomfortable there, it would be a good place to discipline her in the future. I sat at my desk and watched her put on her clothes. As she covered herself her confidence seemed to return. Her expression changed from one of defeated resignation to one that said she could take whatever I dished out. I was pleased that she was not a push over; it made it more fun to train her. When she was fully dressed I held out a file for her to take. “Here is the information on a yacht rental service. Stockwell will be here on Friday. Make arrangements for a two night private cruise. The ship should have a full crew and at least four staterooms. You should make sure that one of the crew is young, pretty, and willing… if you know what I mean.” She didn’t bat an eye. “I understand. Will I be going on the cruise too?” “Yes. You will be the hostess and on call to make sure everything goes smoothly. You and I will share a stateroom.” The knowledge that she would be sleeping with me did not seem to phase her. “What kinds of activities does Mr. Stockwell like? Should I arrange for fishing, or scuba diving?”
I laughed. “Stockwell likes to eat, drink, and fuck. But I don’t know about his new wife. You should be prepared for everything and anything.” “How do I make a deposit to secure the yacht rental? “Take this credit card. It’s good up to $10,000. The full price will be more than that, and when you need to pay give me the details so I can do a bank transfer.” “Okay boss,” she said with a smile. “Do I have a desk and phone somewhere?” “Of course, right next door. Turn left down the hall and it’s the first door on your right. You even have your own private bathroom.” Vickie took the folder and exited my office, swinging her hips ever so slightly. “Classy,” she said as she went out the door. I detected a little sauciness in her tone and smiled. It’s more fun breaking them in if they’re a bit feisty. Chapter 16 – Vickie I was mortified to have to lick the window clean. When Sam patted my ass like I was his pet dog and said "good girl" I swear I could have just exploded right then. Why oh why am I so turned on by all this humiliation? I was glad when Sam told me to get dressed and I could finally get down to some work. A warm rush had surged through my body when Sam said I would be staying in his cabin with him. Maybe he would treat me more as an equal if we were sleeping together. Even though I knew Sam was enjoying what he was doing to me and at times so was I, I just couldn’t help thinking that it was wrong. His touch and the touch of the paddle and crop excited me so much, but my mind still was awash in conflicting emotions. I wished I had someone I could talk to about my feelings, but I would be too ashamed and embarrassed. My office was small and had no window, but it was adequate, and at least it gave me some privacy. After what I had been put through that day a little seclusion felt good. The first thing I did was go down to my car to bring up the packages from Ginger’s Secret. I wasn’t hungry so I skipped lunch and spent time in my bathroom trying on my new outfits. My bum was still burning from Sam’s twenty whacks, and I made sure to put on only the softest and silkiest of panties. I felt even sexier in the new lingerie than I had wearing nothing. Without a doubt I was enthralled by Sam and the situation I was in. He had been hard on me, but at the same time I knew he desired me and was experimenting with ways to excite me and make me want him. As I thought about the way he masterfully played on my submissive sexuality the little birds in my stomach woke up and began fluttering around again. I had to get a grip on myself. In my past life I had once been a successful administrator in a bank and knew I had the ability to be good at the ‘regular’ part of this new job. I wanted to be more than just a fuck toy for my boss. In my gut I knew he would enjoy me more if he also respected me. Plus I would feel a lot better about myself. Now how had I come up with that term ‘fuck toy’? It was so vulgar and so humiliating. But as I repeated those words in my head I felt myself getting wet. It reminded me of all the submission stories I had read and found so exciting. The idea of
being a man’s fuck toy with no control over what he did to me sent shivers down my spine. I sat at my desk and opened the folder Sam had given me. There were three fancy brochures from companies who chartered large motor yachts. The ships were huge, with multiple bedrooms, sitting areas, bars, sun decks, and even small swimming pools. Costs ranged from $50,000 to $100,000 a week. Crews of 4 to 6 people were advertised to cater to your every whim. I smiled at that one. Picking up the phone I dialed the number on the first brochure. A man answered. “Luxury Charters, good afternoon. May I help you?” “Yes, I am calling from the Atwood Advertising Agency. I would like some information on a two night cruise this coming weekend.” “Well, normally our rentals are by the week, but our premier yacht, ‘The Lady Jane’, happens to be idle this weekend. For three days and two nights with a full crew the cost would be $30,000.” I did not let his early reference to the price phase me. “I see pictures and specifications for ‘The Lady Jane’ in your brochure. It has four staterooms, correct?” “That’s right, each with its own bath. And ‘The Lady Jane’ is not an ‘it’. She is a ‘she’.” This guy was a snob of the first order. “I’m sure ‘she’ is beautiful. What about the crew?” “They are beautiful too,” he laughed. “There is captain, a first mate, a cook, and a stewardess.” “Excellent. But I would need a special kind of stewardess.” “What do you mean?” “My boss will be entertaining an important client who likes to party, if you get my drift.” “Oh, I see….” “His actual instructions were: ‘young, pretty, and willing.’” “Ahm….. I think that can be arranged. We have had similar requests before. It would of course cost more.” “Not a problem, but I would have to interview the girl first.” “The girl I have in mind is named Felicia, and I know you would approve. She is a petite Latin beauty who likes to party. But how do I know you are serious?” “I will give you a credit card number now, with authorization to charge me $1,000 whether I take the charter or not. If after meeting your stewardess I decide to go ahead, I will transfer half of the charter amount to your bank account immediately and the balance on Friday when we board the yacht.” The tone of his voice changed. “You have yourself a deal. Give me the credit card information and I will call you when you can come by our office to meet the stewardess and sign the papers.” “I’m afraid it will have to be this afternoon at 4 pm. Otherwise I must call someone else.” Now he knew he was not dealing with a namby-pamby secretary. There was a long pause. “Very good madam. Come to the address on the brochure at 4 pm.” I gave him the credit card information and promised to fax a confirmation. Then feeling very satisfied with myself I leaned back in my chair. It was amazing what you
could do with money. I could do things like this all day. This was easy. The hard part of my job was going to be keeping Sam satisfied. But then keeping him satisfied was going to do the same for me. Chapter 17 – Sam Six o’clock finally arrived, and Karen appeared at my office door. “Party time, boss,” she announced cheerfully. “Where’s your new assistant?” “She has been out arranging for a boat trip to entertain the Stockwells this weekend. I do have legitimate work for her you know.” “Sure, sure,” she laughed. “I’ll bet our Vickie is very efficient. But we can always find excuses to punish her.” “You are the personnel manger from hell,” I said. “As a matter of fact I already had to punish her today. She resisted Ginger’s sexual advances when Ginger was fitting her with new underwear, in spite of the fact I told her not to give Ginger any trouble.” Karen’s eyes lit up. “Really? That is a serious offense. I am going to have to add my chastisement to whatever you did to her. She must learn to submit to women as well as to men.” “I thought you might have that attitude. Start the video recording system and pour us a drink while I go see if she’s back in her office.” I left Karen fidgeting with the video controls and went down the hall to Vickie’s office. She was sitting at her desk with various documents and pictures spread out in front of her. One of the pictures was of a striking young brunette in an iridescent blue bikini. The others were shots of the exteriors and interiors of a luxury yacht. “Is this the boat you have chartered for us?” She smiled prettily and handed me a paper. “It is as soon as you transfer $20,000 to this bank account. The other half will be due on Friday when we board.” “Not cheap, but a fraction of what Stockwell pays us every year. Does the girl come with the boat?” “She does indeed. And I have interviewed her in depth. Her name is Felicia. You will not be disappointed in either her beauty or her attitude.” I was beginning to have new respect for Vickie. The fact that she had taken it on herself to interview the key member of the crew told me a lot about her intelligence and initiative. “Make sure she brings that blue bikini,” I said. “She looks fantastic in that picture.” Vickie smiled. “I already told her that. And she knows she can expect a big tip if the weekend goes well. She is taking care of a sick sister and really needs the money.” “You have impressed me. Good job. But now you must come to my office to meet with Karen and me so we can review your overall performance on your first day.” She raised her eyebrows in surprise, but followed me down the hall to my office. Karen was leaning up against the glass table sipping her wine. There was fire in her eyes. “Come in Vickie,” she said forcefully as Vickie hesitated at the door. “I heard about your disgraceful behavior at Ginger’s Secret. Were you not told to obey Ginger?” “I… I didn’t know…” Vickie was clearly taken back by Karen’s hostile attack.
“You didn’t know what? You didn’t know you were supposed to obey? How many times had both Sam and I told you that?” “But she was a woman…” I took my drink and sat to one side on the stool. By nodding to Karen I let her know that it was okay with me if she disciplined Vickie. In fact I kind of hoped that Karen would go overboard so that I could punish Karen later. Everything she did to Vickie would be done to her in spades. I loved torturing that tight body of hers and driving her up the wall. Karen walked over to the door and closed it. Then she turned to stare at Vickie. “You have to get over any problems you have about sex with women. Now take off your clothes. I want to see that nice lingerie the company bought you.” Vickie looked at me for help, but I just shrugged. “Do as Karen says. Always do as Karen says.” “The longer you make me wait, the harder I’m going to be on you,” growled Karen. For the umpteenth time that day Vickie stripped off her jacket, skirt, and camisole. She stood before us in black lace panties and a black push up bra that mounded and displayed her flesh like ripe fruit. A matching garter belt held the sheer stockings that encased her long legs. She looked very sexy, and she knew it. “Good girl,” said Karen. “Ginger selected well for you. From now on you will automatically strip down to your sexy underwear whenever you are called to meet with us at the end of the day. Now come over here so I can examine you.” Vickie took a deep breath and walked over to Karen. I loved having Karen take charge. It allowed me to relax and enjoy the show. I had seen Karen at work before and knew that she would soon have Vickie groveling and crying for release. My cock was pushing hard against my pants. Karen folded her arms in front of her like an angry school teacher. “Now put your hands on your head and spread your legs. Offer yourself to me like a good sub.” Closing her eyes, Vickie did as ordered, arching her body in a gesture of surrender. Karen reached out and put her hands on Vickie’s waist, then moved them slowly upward to the sides of her breasts. Using her long fingernails she traced the lace patterns on the bra until the tips of her fingers were poking the turgid nipples that distended the fabric. “Ahhh….” Vickie squirmed and shimmied her tits in an effort to avoid the sharp nails. Applying more pressure with her finger tips, Karen maintained contact with the swinging globes. I was getting harder by the second. Karen looked at me. “Sam, please help me restrain this bitch so that I can do her properly. She has not yet learned to hold still.” “No problem,” I said. “I’ll tie her to the clothes tree.” In one corner of my office I had an elaborate clothes tree that had been given to me by a client. It was made of heavy oak and was in the shape of a real tree, with branches at various heights for hanging jackets and coats. The base was wide and strong, providing good stability. This ‘tree’ was not going to tip over even if pulled by a frantically twisting person tied to its branches. I took Vickie by the arm and marched her over to the tree. Karen followed with some Velcro straps she had retrieved from the credenza. “Put your hands behind you Vickie,” I ordered. “Please no… you don’t have to do this…. I’ll hold still.. I promise.”
Karen sneered at her. “But Vickie dear, you won’t be able to hold still the first time I do these things to you. Maybe later, after you are trained, but not now.” After binding her wrists together I pushed her back against the trunk of the tree between two branches. Karen pulled her upper arms back and used two other straps to secure them to the trunk. The result was that Vickie’s breasts were thrust forward, threatening to burst out of the little bra that contained them. Another strap went around her throat to keep her head up. Her legs and feet were left free to move around, as I knew they would when Karen started punishing her. I stood back. Vickie looked incredibly sexy in her high heels and fancy underwear. I wanted to run my hands over her body, but I deferred to Karen. “How’s that Karen? Is she sufficiently restrained?” “Yes and no. She can’t move very far, but her tits will jiggle and jerk when I go to work on them. We have to compress and tie them. I’ll get the rope. Would you please get rid of her bra?” “My god….. what are you doing to me?.......” wailed Vickie. “Shut up bitch,” snarled Karen. “You are going to be taught to be a good slut.” Vickie’s new bra had a little clasp in the front, making it easy for me to release the cups. Her big tits burst free. I was pleased to see that her nipples were long and hard. My hands came up of their own accord and nestled over the round globes, letting the hard kernels poke into the very center of my palms, a place where by rotating my wrists I could apply friction and stimulation to the sensitive tips. "Ahhhh.....", she moaned. "How do you feel Vickie?” I asked innocently. “You are totally helpless you know. Karen and I are going to torment you until you can't stand it. You will be begging us to let you cum." "Oh goddd....." Karen came over with the rope. "I love this new rope," she cooed. "It's just the right thickness, and the rough hemp is going to agitate her skin in a most delightful way." Expertly Karen wrapped the rope around Vickie’s tits and shoulders and forced her tightened flesh forward, with the nipples pointing upward at a rakish angle. Vickie's eyes kept darting from Karen to me and back, full of both apprehension and excitement. In two minutes it was done. Vickie's swollen tits were totally vulnerable. Karen's eyes were flashing. "Wonderful," she said. "Now where is that plastic ruler?" "OH NO....", moaned Vickie, as she realized what Karen was planning. "Oh yes," said Karen, returning from my desk with the ruler. It was broad and thin and very flexible--the perfect little paddle for stinging Vickie's tits. Its short length meant that Karen could wield it with great accuracy. The first slap landed just under her right nipple. "AGGRRR...." More slaps followed quickly, above and below both nipples, causing Vickie to writhe against her bindings. Tears flooded her eyes, but her face was flushed and I detected a slight humping motion in her hips. As I expected, she was getting turned on. Karen paused. "Before I do the nipples I think you should apply some suction to make them bigger targets," she said. I had been thinking the same thing. The prior week I had received some special suction devices that I had ordered from my favorite on line sex shop. Going to my desk I
opened a drawer and took out two little glass bell jars. These transparent bells were designed to fit over the nipples and areolas, with the rims snuggled up against the surrounding flesh. A small brass air valve at the top of the bell allowed you to attach a hand pump and suck the air out of the jar. The hand pump looks like a fat fountain pen, and after three or four pumps in can be disconnected. You are then left with two huge, engorged nipples under glass. When you are ready to torture the fattened nipples you open the valve and release the suction so the jars can be removed. “Perfect,” exclaimed Karen as I began the procedure. Chapter 18 -Vickie I was very proud of the way I had handled booking the cruise and interviewing the stewardess. It was important to me that Sam respect my abilities and not just keep me around for sex. He didn’t know it yet, but I can be feisty and assertive when I have to. I expect that when I get like that he will enjoy putting me in my place, and the thought gives me goose bumps. When Sam had me follow him back to his office to meet with Karen I suspected that I would be in for another session. The fire in Karen's eyes confirmed my fears. Without hardly saying hello she started to chastise me about the incident with Ginger. Her comment about getting used to having sex with other women sent shivers down my spine. "Do as Karen says" Sam had said, and I had glared at him for turning me over to that bitch. After she told me I would have to remove clothes every time I met with them I couldn’t believe it. I might as well sew Velcro on my garments to make it easy to rip them off. As it was it took me a full minute to get down to my new underwear. I glanced over at Sam and could see his erection stretching his pants. He was enjoying Karen's examination of my body. Then in spite of my pleading, they harnessed me to the clothes tree. I tried to struggle but to no avail since they bound me so tightly. My tits were positioned for whatever they wanted to do to them, but binding them with rope was something I never expected. The rough hemp was like thousands of little pins pricking every square inch of my skin. Karen deliberately drew the rough end of the rope over my nipples at every opportunity. Finally they finished and stood back to admire their work. I looked down at my compressed tits and couldn't believe how huge they were; I just hoped there would be no permanent damage. Then the bitch Karen wanted Sam to apply suction to make my nipples even bigger. I watched Sam attach the pen-pump to one jar and then place the jar over my left nipple. He held it against my breast while he drew the plunger and sucked out the first gulp of air. Instantly the jar stuck to my tit. It was then easy for him to use both hands to hold the pump and work the plunger. When my left nipple was sucked to almost fill the jar, he moved his torture device onto my right bud and repeated the procedure. Both nipples were then encased under glass. Not satisfied with their size, Sam moved the pump from one to the other and sucked out more air.
“Please Sam… no more….”, I begged him. My poor nipples were fat and long and terribly distorted. Tears streamed down my cheeks as I writhed and squirmed against the unyielding tree. I was crying more from the humiliation than from any real pain, and all the while I was aware of a growing sexual excitement. Karen smiled at my predicament. “Keep going, Sam. I want nice big targets for my ruler.” “NOO…. PLEASE STOP…” I screamed. The thought of that ruler snapping against my sensitized flesh was too much. I knew it would hurt, but not how much. In the meantime moisture was oozing out of my pussy onto my thigh. “Okay. Let’s see how big and tasty they are now,” said Sam. He released the suction and removed the jars. It felt like my tits were going to burst. “Perfect--at least an inch long and throbbing for attention,” he said as he lowered his head and took one succulent bud after another into his mouth. Using his lips, teeth, and tongue he tormented and persecuted my tender nips, drawing them out to even greater length. Karen watched, smacking her hand with the ruler, eager to get at me. Sam finally raised his head. “Okay, Karen. She’s all yours. Teach her not to disobey in the future.” “My pleasure,” gloated Karen. She swung the ruler so that the flat part smacked up against the side of the tender cylinder that was my enlarged nipple. A stinging paid shot through my chest. I gasped and screamed. “I’m sorry…. I will never disobey again…. I am yours to use…. please no more…” But Karen just laughed and hit the other nipple. Then she drew the flexible plastic back like a bow and let it smack on my pointy tips. Her eyes were flaring like she was in some kind of trance. Again and again she punished my poor boobs, until finally Sam grabbed her wrist and restrained her. “Easy Karen. I think that’s enough for now.” “Please Sam, let me do her some more,” pleaded Karen. “She’s loving it. Put your hand on her pussy and you will find a dripping wet slut.” I was mortified. Sam slid his palm down my bare stomach and into my panties. I knew it was going to be like putting his hand into wet grass. My helplessness and humiliation had turned me on to the point where I was gushing. “So true,” laughed Sam as he felt me. I was ready to cum, but he took his hand away and put it up to my mouth. “Lick me clean you hot bitch,” he commanded. “Then I’m going to put some clamps on those naughty nipples of yours. I want to keep them long and tender while Karen shows you how to please a woman. You may need to know this technique on our weekend boat trip.” “NOO. NOOO… You can’t.. My nipples cannot take anymore…”, I pleaded as I frantically licked his fingers. Sam drew his hand back and slapped me across the face. “Don’t you EVER tell me what I can and cannot do! Karen, bring the clamps.” All I could do was hang my head and await my fate. Karen worked the claws of the clamps on me with great relish. I shut my eyes and bore the momentary pain. The clamps were connected with a small chain, which Karen tugged several times to make
sure the jaws were secure. But with the size of my nipples there was plenty of contact with the rough surface of the clamps and no chance of them coming off. I twisted and moaned and waited for what was coming next. Chapter 19 – Sam I was hard as a rock watching Karen torture Vickie’s nipples by pulling on the chain. The fact that Karen was right about Vickie being wet made me stop worrying about Karen being too rough. Also, I did not like Vickie saying I couldn’t do something. She had to be taught a lesson. Karen put one hand on the bulge in my pants as she continued to jerk the chain. “Sam my dear, you have no idea how much punishment a woman’s breasts can take when she is turned on. I’ve barely begun with this bitch.” I just smiled. God, her hand felt good on my cock. Her comments and touching were letting me know how much she wanted her tits to be abused just like she was doing to Vickie. “Now Vickie,” Karen continued, “you are going to tell me how you are going to behave in the future.” She pulled the chain to the left, exposing the swollen side of one of Karen’s breasts to the stinging swats of the ruler. SLAP “OHHH… I am going to be good… whatever you want….” SLAP “What are you going to do about Ginger?” “What do you mean?” SLAP SLAP “You offended her by resisting her advances. She is a friend of mine… a good friend.” “AWWW… I am going to apologize… I am going to tell her she can touch me if she wants.” “Not good enough.” “OK, OK…. I will invite her out to lunch and tell her I want her to touch me.” SLAP “Better, but more detail. How is she going to be able to touch you in a restaurant?” “All right… all right… please don’t hit me there again… I will invite her to lunch at my house, and I will wear something sexy and make myself totally available to her.” My cock was now drooling on my slacks. I pushed it up against Karen’s leg. She gave me a kiss and caressed my bulge with the ruler. “Haves patience Sir. You will get to use this big thing soon enough.” Karen returned her attention to the writhing Vickie. The chain was pulled the other way, presenting a fresh target for the wicked ruler. WHAPP WHAPP “You be sure to do that with Ginger. She will teach you a few things. But now you are here with us. What are you going to do for me and Sam?” “OHH.. anything…. anything you want… please….” “Stop whining. You love it and you know it. Now what do you think we want?” “I don’t know…. just tell me and I’ll do it….” SLAPPPP “Use your imagination. What are you going to do?” “OOOHHH.. I will…. I will lick your pussy and suck Sam’s cock,”
That sounded good to me, but Karen wasn’t satisfied. “What else are you going to lick?” She hesitated, and Karen drew back the ruler. “OK.. ok… I will lick your tits and your ass..” “And what about Sam’s ass?” Vickie shuddered in her bindings and seemed to cross a threshold into a realm of total abandoned. Karen’s words and punishment had broken her. She sobbed and let go. “Yes…. YESSS… I will stick my tongue up into his ass… and I will lick his balls… and he can fuck me anywhere he wants.” Karen smiled. “Good girl. Now I think you deserve a little reward. I am going to make you feel things you have never felt before.” I had an idea of what was coming. My custom clothes tree had a special feature that I had used several times to pleasure Karen. There were two narrow wooden planks concealed in the trunk on heavy duty hinges. When these boards were raised perpendicular to the trunk, they formed a ‘V’ with the apex at the trunk and the legs sticking out some thirty inches. The ‘V” was located at about waist height and formed a kind of seat. A person tied to the tree could have their legs raised and secured to the boards, leaving them spread open. Their tormentor could sit on a stool inside the ‘V’ and have complete access to the most sensitive areas of their body. “It’s time to sit her in the tree,” said Karen. “But first we have to get rid of the garter belt and panties.” The two of us undid various snaps and soon had Vickie naked except for her stockings and high heels. She made a valiant effort to keep her legs together, but Karen pinched her thighs and made her squirm so we could see how swollen and wet she was. “Hold her ankles while I raise the platform,” I instructed. The planks came up and locked into place, with Vickie standing between them. Karen wrapped her hands around one of Vickie’s ankles and lifted her leg until her thigh was resting on the plank. I did the same on the other side, and then, putting a hand under her ass I raised her until she was sitting at on the point of the ‘V’. A couple of straps around her legs and the planks, and she was secured in place, wide open for whatever we wanted to do. “Now let’s get a couple of low stools.” Karen’s voice was tinged with excitement. I knew how much she enjoyed the first time with another woman. I brought the stools, but felt I was being too passive. My cock was about to burst and demanded that I participate. I wrapped my arms around Karen and grabbed her hair so I could pull her head back and kiss her. Her mouth opened immediately, sucking at my tongue. “You are such a wicked personnel manager,” I stammered when I got my mouth free. “What are you going to do to my new assistant?” “I am going to tease her pussy and ass with my hands and mouth, and I am going to use a couple of my newest toys on her. We’d better hope everyone else has gone home, because she is going to be screaming out multiple orgasms.” “What about me?” I asked in a tone that told Karen I was still the boss. She looked at me sheepishly, realizing that she was not going to be allowed to play with Vickie and ignore my growing lust. “Yes Sir. If you will sit on the stool next to me we can do this together. And it would be better if you took off your pants first. They seem to have a big wet spot.”
“Okay, but you get out of your clothes too. You are definitely overdressed for this exercise.” We smiled at each other as we stripped. As always, I was overwhelmed by the sight of Karen’s fabulous body. But as I tried to grab her tits she pushed me away playfully and pointed to the stool. Vickie meanwhile was twisting and squirming to try to escape from her vulnerable confinement. However, the look in her eyes said that she really didn’t want to. Her bound tits swayed back and forth, jingling the chain. Karen sat on her stool and maneuvered into position with her nose just above Vickie’s pussy. I could see her long fingernails working their way up the insides of Vickie’s thighs. “She smells so ripe,” said Karen. “I think I’ll just put a finger here…. and there …. and here.” “OHHH…..” “Ummm… maybe if I licked a little right here…..” “AHHHHHHH…” I sat on my stool and leaned in to watch. My throbbing cock touched Karen’s leg and reminded her of my need. One of Karen’s hands left Vickie and cupped the sensitive end of my organ. “Arggg…” I groaned. She continued to squeeze me as she opened Vickie’s lips to expose her clit. I was amazed at how prominent it was. “Are you going to suck on it?” I asked. “Not yet, my dear,” said Karen. “We women know how to drag this out to make the end much more satisfying. I am going to lick and nibble all around it while I am doing some other things, like this…….” Vickie’s ass was now bouncing on her little seat, and strange noises were coming from her throat. I reached over and played with Karen’s tits to encourage her. Just as it seemed Vickie was going to cum, Karen withdrew her mouth and fingers. She put one wet finger on Vickie’s mouth and pushed it in past her lips. “Lick my finger bitch,” she said forcefully. Vickie complied, her hips still squirming on the seat. Karen gave my cock one last pull and then took her hand away. “Sam, please bring me my purse. It contains a few things I need.” Eagerly I got up and retrieved Karen’s large leather bag. I was very curious about what new toys she had in there. Grinning at me, she opened a zipper on the side and removed two tube-like devices. One was a thin, made of shinny metal, with a switch on one end. The other was plastic and a little thicker, and it was curved in a rough ‘J’ shape. It also had a switch on one end. She held up the straight metal one. “This is going up her ass. Not too far…just enough so that when the vibrator is turned on all those little nerves will be buzzed until her pussy opens like the mouth of a cave.” “OH NO…..” Vickie’s ass squirmed against her seat, as if she were trying to seal it shut. Next Karen showed me the curved plastic tube. “And this other one is going to curl up in her pussy and vibrate against her G spot. The shape allows me to do this without blocking access to her clit, so at just the right moment I can press down on it with my mouth.”
“OHHH MY GODDDD….” Vickie was imaging the coming sensations. “But first we need to lube this tube so it will slide easily into her ass. Sam, you and Vickie are both secreting enough stuff to change the oil on my car,” she laughed. And it was true. Between us she got enough juice to lather that metal tube to the point where it almost slipped out of her hand. “Now take a deep breath Vickie. This may be uncomfortable for a few seconds, but then you will love it.” “Do I have any choice,” she whined. “No you don’t. Your ass is exposed and open. I am going to just ease this up in like so….” Vickie shifted her weight on the little seat but could not avoid the probe. “OpppPPP…. ooohh… aaaaHHHH…” she cried. “Now for the vibration…” “Ummmmm.. yess….. oh that’s… that’s…. ahhh…..” “Hold onto this please, Sam. I need both hands to work the other tube into her pussy.” I took hold of the end of the metal tube and pushed it slowly in and out of Vickie’s ass. She was used to it now, and she humped back against it to get the maximum stimulation. Then Karen began feeding the curved plastic up into her pussy, turning it so the tip of the curve was reaching back up toward her lower stomach and her G spot. “THERE….. OH MY GOD, THERE… RIGHT THERE..” “Easy honey, let it probe around a little. I know where you want it, and it will end up there. First I am going to turn on the vibrator.” At that point Vickie went nuts. She shook that wooden clothes tree like a gale wind was blowing the branches. Karen’s mouth descended on her clit and held on as Vickie screamed out her orgasm. My new personal assistant was one hot bitch when you got her going. And I knew from that moment she was going to have no problem making love with other women. Karen removed her toys and stood up. “Your turn Sam. She is still riding the wave. Now she needs to be filled.” I kicked the stools aside and moved into the open space between Vickie’s spread legs. My cock was at just the right height to penetrate her. She had her eyes closed and was shaking her head from side to side as if in a trance. “Let me help you,” breathed Karen, and she took me in her hand and guided me to the grotto. I went in easily and all the way. Vickie gripped me and began humping her hips like a woman gone mad. It was incredible. With great effort I held back my orgasm to prolong both our pleasures. Karen added fuel to the fire by going to the side where she could jiggle the nipple clamps and whisper in Vickie’s ear. I don’t know what she said, but the effect was to drive Vickie to another powerful orgasm. She moaned and thrashed and moaned some more. I could hold back no longer. “AHHHHHHH….. AHHHHHHHH… AHHHHHHH……” Then we both went limp against the tree, hanging like some kind of sleeping primates on the branches. Karen was smiling and caressing us both. I was satisfied and content to let Karen have Vickie to herself for the rest of the evening.
“Vickie I am going to leave you here with Karen. You have already been told to do whatever she says. She has many things to teach you.” Karen’s eyes lit up. “Thank you Sir. I think Vickie is ready to learn how to please a woman. And I am ready to be pleased.” Chapter 20 -- Vickie Karen was gentle with me as she untied my breasts and released me from the clothes tree. I was like a limp doll. She helped me to the couch, and for the next ten minutes held and kissed me, telling me how good I had been and how much she had enjoyed driving me crazy. She knew it was really going to hurt when the nipple clamps were removed, so she did it slowly and immediately replaced the hard jaws with her mouth, gradually reducing the pressure until I felt just her soft tongue lapping away the vestiges of the sharp pain. Her soothing words and actions were a welcome change from the harsh but exciting treatment when Sam was present, and I found myself responding to Karen’s sympathy and attentions. She seemed to understand perfectly how the combination of helplessness, pain, and pleasure had made me feel. There was no resistance on my part when she urged me to do some of the things to her that she had done to me. She lay back on the couch, and I used my mouth and hands as she directed. Only once, when I was ordered to lick her ass, did she have to remind me that refusing her was not an option. My body could not take another round of punishments Sam, at least not for a while. My hesitant, virginal approach was obviously exciting for Karen, and she had several orgasms in quick succession. I learned just where and how to tease her, and when to apply the stimulus to drive her over the top. All the while she kept talking dirty to me, saying how she was so glad to have a sex-starved submissive like me in the company, how she and Sam were going to use me, and how I was going to love it. It got me so hot I had another small orgasm rubbing my pussy on the edge of the couch as I was licking her clit. It was about ten o’clock when she finally had enough and allowed me to get dressed and go home. I ate a little cheese and fruit and then collapsed on the bed. The next day was Friday, and I knew I would be busy making the last minute arrangements for the boat trip with the Stockwells. As I fell asleep I reminded myself that I had to be in Sam’s office by 9 am to serve him coffee and have my clothing inspected. The next morning I dressed for the cruise in slacks and an open collar shirt. My low cut bra, courtesy of Ginger, would allow me to open quite a few buttons on the shirt, depending on the situation. I was counting on that to satisfy Sam’s inspection. Given the tenderness of my breasts I was hoping Sam would be satisfied that day with just looking at them. Carefully I selected the other clothes I thought would be suitable for two days and nights on a boat, and packed them in a small bag. By the time I had something to eat and got to the office it was already five minutes passed nine. I half expected to see Sam sitting in my chair taping his leg with the riding crop, but instead there was a note addressed to me on the desk.
Good morning, Vickie: I trust you had a pleasurable and educational evening with Karen last night, and that you are in the right frame of mind for helping me entertain the Stockwells. Regretfully I have a meeting this morning and cannot be there to check your appearance, but I will do so when we meet on the boat. If you have not brought a revealing bikini, I suggest you get one before this afternoon. I will be picking up the Stockwells at the airport and will bring them directly to the marina. We should be there about 11 am, and they will be needing lunch. Fortunately Ginger had outfitted me with a bikini along with my new underwear. I had resisted her choice because it was a size too small, and left little to the imagination, but now I was glad she had insisted. My voluptuous body in that suit was going to be a sharp contrast to the tight little body of Felicia in her skimpy neon blue bikini. Then there was Stockwell’s new trophy wife to consider. I wondered what she was going to look like in her swim wear. I had a feeling that the men’s attention was not going to be on me. Realizing that I had not thought about the food or the number of meals we would have on the boat, I decided to go immediately to the marina to check on things. The yacht rental company had seemed very professional, and I had rented the boat from noon on Friday to Sunday evening with full services, but you never know. If anything went wrong, it was going to be my ass, literally. I need not have worried. The ‘Lady Jane’ was ready to receive and pamper her guests. I was greeted by the booking agent, who introduced me to Captain Mike, First Mate James, and the cook, Sandra. I already knew Felicia, the stewardess. All were smartly dressed in white uniforms and red boat shoes. Sandra was an older woman, who wore pants like the men. Felicia, however, wore a short skirt and tight top, and looked super cute. Mike was right out of central casting as a sea captain. He was a large man, about six-four, with big shoulders and a beer belly that looked like it could hold a couple of six packs. His bushy hair was thick and graying, and his bright blue eyes shown like beacons from his deeply tanned face. I guessed he was around sixty years old. He carried himself with confidence, and my overall impression was that he was competent and tough. He was certainly attractive. The first mate, James, was of average height and build, and much younger, probably still in his twenties. He had the intelligent look of a college student working a part time job. With curly brown hair and classic features he probably had his pick of the coeds. I could see Felicia had been flirting with him, and he was eyeing her hungrily. I must say I couldn’t blame him. Felicia looked even better than when I had interviewed her. She was a petite girl, probably just over five feet, and perfectly proportioned. Her long hair was jet black, and framed a remarkably beautiful face with green eyes and full lips. Sexuality radiated from her like the mist over a pond on a hot day. I knew from the interview that she was twenty four, but her girlish appearance made her seem much younger. After exchanging some pleasantries I requested a tour of the ship and a look at the provisions. I wanted to be sure there was enough food and liquor, as well as gear for swimming or fishing or whatever. Captain Mike led the way, with the booking agent tagging along.
“You will love this ship,” he said. “It is big enough to provide every luxury, but small enough to be able to go wherever we want.” He was right about the luxury. The ‘Lady Jane’ was like a fancy four story hotel. The dining room had huge glass windows on three sides, and a table large enough to serve a dozen guests. There was a well decorated lounge with a bar, and several intimate sitting areas both inside and outside provided comfortable places for relaxation, reading, or whatever. On the upper deck a small swimming pool was surrounded by a terrace adorned with potted plants, chairs, tables, and chaises. In one corner a hot tub was well suited for a party on a cool evening. Each of four bedrooms on the lower decks had its own full bath and a small balcony where the occupants could sit outside in complete privacy. At the rear of the lowest deck was a platform that provided access to a small launch that could be lowered for water sports or to ferry people to the beach. Secured neatly to the walls around the platform was equipment for fishing, diving, water skiing, and more. Captain Mike showed us stairs that led downward from the platform to the engine room and crew quarters, but did not offer to show us that part of the ship. To my surprise there was a small elevator to take us from this lower deck back to the top. I got in first and stood at the back facing forward. The booking agent followed and stood beside me. Big Mike came in after us and turned in such a way that one of his arms ended up brushing the side of my breast. “It’s a little tight in here for three people,” he said with a smile. I tried to pull back, but he leaned into me to maintain contact with my tit. He was clearly testing me. “Please give me a little more space,” I said tersely. I was determined to remain in charge. The booking agent raised his eyebrows, but said nothing. “Sorry,” he said, and shifted his position like he was trying to comply with my request. The net effect was to rub his arm across my hardening nipple. I took a deep breath and tried to maintain my composure as the elevator slowly ticked its way upward. Captain Mike’s heavy after shave filled the confined space with a masculine, heady aroma. Finally the door opened and released us into the bridge area at the highest point on the ship. The room was lined with instrumentation and communications equipment, and reminded me of the cockpit of an airplane. The booking agent walked over to a computer terminal and typed in some commands. “I assume that you found the ship satisfactory,” he said. “I am connecting to the internet so that you can transfer the funds to make the final payment for the cruise.” He was not going to let the party begin without his money. I entered the codes into the computer and sent a confirmation document to the printer. The agent took his copy, bid us a pleasant weekend, and left via the outside stairway. Captain Mike and I were left alone on the bridge, with two hours to wait before the passengers were due to arrive. He leaned back against the chart table and looked me up and down, not attempting to disguise his interest in my body, especially my tits. There was no way I was going to let him intimidate me. I decided to put him in his place. “Captain, we need to discuss where we are going today. Please keep your mind on your job.”
He laughed. “My job is to make sure my passengers have a good time,” he said. “I have been on excursions with Felicia before. I know what this trip is about, so don’t get all high and mighty with me.” I felt the color rise in my cheeks. My attempt to take charge of the situation was dissolved by his knowledge that I had essentially booked a sex cruise. I could hardly be offended by his checking me out. Still I tried to recover. “Yes, well what the other passengers do is up to them, but as the manager of this event I expect to be listened to and treated with respect.” Mike pushed off of the table and stepped right in front of me. For a big man he moved very fast. He grabbed one of my wrists and twisted my arm painfully behind my back. With his other hand he lifted my chin so that I was looking up into his face. His eyes were flashing. “Now you listen to me! I am the captain of this ship. That means legally you have to obey my orders. If you read the contract you would know that. Either accept that right now, or get off. When your boss arrives with his clients I will tell them the trip is cancelled because you did not like my manner.” The nerve of that guy! Being the captain of the ship did not give him the right to assault me. I could have him arrested...that is, if I could prove it. With no witnesses it would be his word against mine. And the last thing I wanted was to have the trip cancelled and be blamed for it. Sam would be so angry I could lose my job, and if I wasn’t fired, I would surely be severely punished. I swallowed my pride and backed down as gracefully as I could. “I understand Captain, Sir. You are clearly in control here. But my boss will expect me to know what the plan is. Can we at least discuss it?” He still held my arm so that I could not move without sending a sharp pain into my shoulder. My subservience seemed to placate him, but he moved to confirm his power by dropping his hand from my chin to my breast. He took his time squeezing and exploring while he talked to me. “Yes, of course we can discuss it. I suggest that we start off by cruising along the inland waterway, looking at all the fabulous mansions and yachts. After lunch we can go out into the ocean and visit some of the uninhabited keys. You can all go swimming.” His fingers continued working my tit. My sore nipple hardened, and I felt the familiar tingling in my stomach. Captain Mike was going to do what he wanted, without worrying about consequences. It was turning me on, and he knew it. “Please…” “Please what….” “Oh god…..” Chapter 21 – Sam I decided to take a limo to the airport to pick up the Stockwells so that I would be able to sit and talk with them in the back seat. When they emerged from the baggage area I was waiting at the end of the pick up area. “Hey George, over here,” I shouted.
He smiled and walked toward me pulling a small suitcase. Beside him and holding his hand was a slender blonde. I had expected his new wife to be a beauty, and I was not disappointed. “Hello Sam. I would like you to meet my wife, Caroline.” “It is a great pleasure,” I said with true enthusiasm. She smiled like a little girl on Christmas morning. “I am pleased to meet you, Sam. George has told me all about you and your great parties. We are really looking forward to this weekend.” “Wonderful. Let’s get in the limo before the cops shoo us out of here.” Carolyn got in first, pulling up her flowing skirt and revealing a pair of nicely shaped legs and ankles. Once George was settled beside her, I pulled down the jump seat and sat facing them. The driver knew to take us directly to the marina, and as the car pulled away I got my first good look at my friend George’s new trophy. I was immediately struck by her eyes. Years ago I had heard a woman described as having “bedroom eyes”, and I had thought that phrase was right on. It is difficult to describe eyes like that, but once you have seen them, there is no doubt about their nature. The pupils radiate a kind of sultry, sensuousness that make you want to grab her face in your hands and lavish it with kisses. I could stare into eyes like that for hours. George began talking about their trip and how hard he had been working, but I was only half listening. My attention was focused on those light blue eyes that kept darting to mine like she was sprinkling sugar on cereal. A satisfied smile remained on her lips, a sign that she was well aware of the effect she was having. Not wanting to be caught ogling her, I turned toward George. “Well George, after all that stress you need to unwind. The cruise I have arranged for you should be just the thing.” “Who else is going?” asked Carolyn. “Only me and my personal assistant, Vickie,” I said, “plus, of course, the crew, including a young stewardess to cater to our every need.” Somehow I managed to speak to her without getting caught by her eyes, and in the process I noted her other features. Her blonde hair was cut short and pulled back, with little strands teasing her ears. In spite of their coming from the North in the wintertime, her skin was nicely tanned. The tight bodice on her dress highlighted small but firm breasts with prominent peaks. I guessed her age at around thirty, and she was one sexy package. George interrupted my appraisal. “You know Carolyn and I have been married only a few months,” he said. “Our honeymoon lasted two weeks and almost killed me. But now I’m rested and ready to go again.” Carolyn and I both laughed. “How did an old codger like you get such a gorgeous new wife?” I asked. “I don’t kid myself,” he replied. “I am a rich man who craves the attention of a beautiful woman, and Carolyn is taking advantage of her god given talents to set herself up for a comfortable life. On our wedding day I gave her one million dollars. For every year that we stay married, another million dollars goes into her bank account. Either one of us can end it at any time.” “Don’t make it sound so mercenary,” pouted Carolyn. “I love you for more than your money. Life with you is exciting.”
“It sounds ideal,” I said. “We should all take what we can from life, while we can. I admire you both.” George grinned at me. “So far she’s kept up with me. But my demands are about to escalate.” “You don’t scare me,” said Carolyn. “Bring it on.” Then, batting those irresistible eyes in my direction, she added, “By the way, I think your friend Sam is kind of cute.” I looked at George and saw he was loving it. “This is going to be a great weekend,” he said. At about that time the limo pulled into the parking lot at the marina. I signed the driver’s ticket while they retrieved their bag and mine from the trunk. Vickie was waiting for us at the entrance to the pier. She looked good, but seemed a little disheveled. “Everything OK Vicki?” I asked. “Yes Sir, the ‘Lady Jane’ and I are ready to welcome you.” “Excellent. I want you to meet the Stockwells, George and Carolyn. This is my assistant, Vickie.” “Please to meet you,” said George. “I understand you are coming with us. I hope you are in a party mood.” The two women looked at each other and smiled. “Oh yes Sir,” she said. “This is definitely a party ship. Lunch will be served as soon as we cast off.” “I would like to get out of my travel clothes and into something more comfortable,” said Carolyn. “Right this way,” Vickie said as she led us out on the wooden dock. We passed a number of smaller boats on our way to the end of the pier, where the crew of the ‘Lady Jane’ was lined up with the impressive yacht tied up behind them. Introductions were made, with everyone looking over everyone else with an eye toward the coming party. George and I both had a hard time keeping our eyes off of Felicia. Vickie continued in her role as master of ceremonies. “Let’s start with a quick tour of the ship, and then you can change clothes in your stateroom. Captain Mike is going to take us on cruise of the waterway while we have lunch. Then if you wish we can go swimming this afternoon on a private beach.” The Stockwells were very impressed with the yacht and their accommodations. I congratulated Vickie on a job well done, but made her undo one more button on her blouse. She was going to have to emphasize those big tits if she was going to compete with Carolyn and Felicia for the men’s attention. James untied the lines and jumped aboard. The big diesels on the ‘Lady Jane’ came alive, and we glided out into the channel. I stood with Vickie on the upper deck and admired the other big yachts in the marina. George and Carolyn went to their stateroom to change clothes. In a few minutes our guests came up to the dining area. Carolyn was wearing shorts and a tee shirt and looked good enough to eat. We all sat down to a delicious seafood lunch and chilled white wine, served by a very flirtatious Felicia. The scenery was spectacular and the conversation lively. We had a light desert of sorbet and cookies, and finished off the third bottle of wine. Everyone was feeling very relaxed. “This is great,” exclaimed George. “I am going to have to send more business your way. Carolyn why don’t you show Sam how much we appreciate his hospitality.”
Carolyn had apparently been expecting this, because she got up immediately and came around the table to sit on my lap. I was already half hard from just looking at her, and she had to feel me stiffen under her tight ass. “Sam, you are wonderful for making such a nice experience for us. My husband wants me to express our thanks.” She twisted her body on my lap, her thousand watt eyes locked on to mine. I picked up my wine glass and offered her a sip, which she took while continuing to look at me over the rim of the glass. Her eyes sparkled with mischief, and she licked her lips just before lowering her head to kiss me. “Bravo!” said George. “I like to see my wife enjoy herself.” I glanced across the table at Vickie and saw the surprise on her face. She had expected that I might share her with George, but having George urge his wife on me was something else. Meanwhile Carolyn settled into my lap and started nibbling around my ear. George began to frown and looked like he might interrupt. I was enjoying Carolyn too much to allow that, so I enlisted Vickie to keep him occupied. “Vickie, I am sure George is uncomfortable with all that pressure in his pants. Take care of it right now.” She looked at me, then at George, trying to interpret my command. George pushed back from the table. “Yes, Vickie. I do need more room in my pants. If you could just loosen them….” “Of course,” she said, and dropped to her knees. He let out some long sighs as she undid his belt and pulled down his zipper. I watched long enough to be sure she was doing her job, and then turned my attention back to his wife. Carolyn’s T shirt had come out of her shorts, and it was easy to slide my hand under it and up over a bra encased breast. The conical point I had noticed before was now turgid against my palm. As I squeezed she squirmed and stuck a wet tongue in my ear. “You are a naughty wife,” I teased. “Yes,” she purred. “I deserve a spanking.” That sounded like a very good idea to me. “George, you wife is being naughty and needs to be spanked. Do I have your permission?” George was leaning back in his chair with his legs extended and his pants down around his ankles. Vickie had his stiff cock in her hand and was licking the tip. Little bubbling noises were coming from his throat, but he managed to respond. “What do you think Vickie? Should I let Sam spank my wife?” There was only one way Vickie was going to answer, that is if she wanted to keep her job. She did not disappoint me. “Yes George. Naughty wives must be punished right away. You are not available to do it right now, and Sam is very good at it. I think he should put Carolyn over his knee and spank her while we watch.” “AHHH…. that feels so good… yes, we will watch it together…. Sam, please spank my wife for me, and do it hard, on her bare ass.” Immediately I stood and carried Carolyn to where I could sit in an armless chair in a place that was visible to George and Vickie. She wrapped her arms around my neck, shivering and moaning softly. Obviously the idea of being spanked in front of her husband by a strange man was turning her on. It certainly was doing that for me.
I sat down and turned her over on my knees. There was a button on the side of her shorts at her waist, and I quickly undid it, pulling her shorts up and over her protruding ass. She squealed as I yanked the material down her legs to her ankles. “Grab the chair leg and hold on,” I barked. Out of the corner of my eye I saw Felicia standing in the doorway to the galley, watching intently. Carolyn’s nicely rounded ass lay exposed on my lap. The straps of her thong framed the tightly mounded cheeks, and I began exploring their texture with my finger tips. There was not much fat to cushion her once I started the spanking. When I reached the tops of her thighs she parted her legs slightly in open invitation. George had found himself one hot babe. “OWHHHH….” she screeched as the first slap quivered her flesh. Quickly I followed up with a multitude of stinging blows, alternating from cheek to cheek. If she had thought this was going to be a pretend spanking, she was very wrong. My lust was raging and I wanted her cowed so that she would submit to whatever I wanted. “Good… good…” yelled George. “Give it to her good. She had been too uppity lately and needs to learn her place.” Vickie’s eyes were glazed over as she watched the young wife bouncing on my knees and sobbing. George had his hand down inside her shirt as she pumped on his cock. From the look on his face and the noises he was making I knew he was close to shooting his load. When I thought Carolyn had had enough I stopped and put my hand up between her thighs. The fabric of the thong covering her pussy was soaking. “George your wife has been punished and now she needs to be fucked. If it’s all right with you I am going to leave you in Vickie’s good hands and take your wife into my stateroom and fuck her brains out.” “Go for it Sam. That’s it Vickie…. don’t stop…. “ I pulled Carolyn’s shorts off of her ankles and turned her so that I could throw her over my shoulder and carry her to my bed. George and Vickie would probably have liked me to fuck her there on the dining deck, but she was on fire and I wanted to be lying looking into those bedroom eyes when I thrust into her. The weekend had just begun, and there would be more group fun later. Chapter 22 -- Vickie Like a good personal assistant I concentrated on doing what my boss wanted. In this case it was keeping George so hot that he would not care when his wife was carried away to be fucked. It was not that hard to do. He was one of those guys whose cock and balls are super sensitive to a soft, feminine touch. I caressed and teased him, alternating between being light and heavy, and dabbing the underside of his glans with my tongue. He moaned and twisted in the chair. “Oh god Vickie….. you are so good at this… I want you to come work for me.” I smiled at him and rimmed his ass gently with my finger tip. “You are the one who will be cuming, George. But not just yet. I have other things I want to do to you.” “Ohhh… “
George was sweet. I liked giving him pleasure. After my rough treatment by Captain Mike I was glad not to be on the receiving end for a change. The captain had bared my tits and slapped them around until I begged him to just fuck me. That was apparently what he wanted to hear, because he bent me over the chart table and gave it to me good. Before he let me cum he made me promise to come see him on the bridge whenever I had free time during the cruise. I cannot believe what a slut I have become in such a short time. The precum leaking out of George told me he was getting too close. I let go of his cock and began working his shorts down his legs. “Now hold still George while I get your pants out of the way.” He groaned but did as I told him, and I soon had him naked from the waist down. It was then that I noticed Felicia watching us from the doorway. “Come here Felicia,” I ordered. “You can help me keep Mr. Stockwell occupied while Sam fucks his wife.” Felicia had a big smile on her face as she sauntered toward us, swinging her hips. She probably thought it was about time she got involved in the action. Otherwise how was she going to earn that big tip? “Yes mam,” she said. “What would you like me to do?” “Why don’t you do a strip tease for our guest. Show him that tight little body of yours.” Felicia stood a few feet in front of George’s chair and put her hands behind her head. Slowly she began rotating her hips. She looked in his eyes and licked her lips. My hand returned to his cock, which seemed to grow another two inches. “Isn’t she gorgeous George? Would you like her to take off her shirt so you can see her tits?” “God yes…” Her hips still moving, Felicia pulled her shirt up and over her head. As I had suspected she was not wearing a bra. Like mounds of coffee ice cream with cherries on top, her perky tits stuck out on her chest. With her hands back behind her head, she shook them so they danced in front of his face. “Come closer so he can feel them,” I said. From my position kneeling on the floor beside George’s chair I felt like the director of a play, with the spasms in his cock providing the feedback from the audience. George raised his hands and Felicia leaned toward him, dropping her tits into his palms. He squeezed and pulled her forward so he could rub her stiff nipples back and forth across his face. As he nipped at them with his mouth I felt the blood surge through the hard column in my hand. “Ahh, that’s so nice George..,” she sighed. “You are making me hot.” “She wants you George,” I said. “Put your hands under her skirt and feel her ass.” He captured a tit with his mouth and dropped his hands to reach behind her thighs and pull her between his legs. She snuggled into him giving him easy access to her ass. I knew she was probably wearing a thong, so his hands would be closing on bare cheeks. “OH George..’’ she moaned convincingly. She was either a very good actress, or she was really getting turned on. I was pretty hot myself, so I suspected the latter. Maybe watching Sam spank Carolyn had gotten to her.
“Straddle my lap,” panted George. “I can’t last much longer and I want to fuck you.” Felicia yanked up her little skirt and climbed onto his lap, her legs spread wide. I pulled the front patch of her thong to the side and put the tip of his cock in just the right place. Her juices ran onto my hand. The girl was not acting. “YESSSS….” she wailed as she lowered herself onto him. I sat back and watched as the little minx rode him up and down like she was the pony on a merry-go-round. He held onto her tits and rained kisses on her face. In less than a minute it was all over. She collapsed onto him, and he wrapped his arms around her little body. Chapter 23 – Sam We lay on the bed exhausted from the explosion of our mutual passion. Carolyn had thrashed and screamed when I squeezed her sore ass and pulled her into me. Those sultry eyes that had aroused me so much had become electric when I had her naked in my arms on the cool sheets. She took me deep into her and shuddered with several climaxes before I let go and moaned my own pleasure. Afterwards we clung to each other and drifted into a shallow sleep, occasionally murmuring sweet words to each other. The combination of the gentle rocking motion of the boat with the food, wine, and sex seemed to fill my head with fluffy cotton, making staying awake impossible. Carolyn professed the same sleepiness, and did not seem at all concerned about how her husband might be reacting to her absence. Our little nap lasted about half an hour. I awoke first and was enchanted to find Carolyn still draped over my body, her legs on the outside of mine, with my limp cock nudged up against her moist pussy. My hips moved of their own accord, as if directed by Mr. Happy to give him some stimulation. The result was a quick stiffening that brought Carolyn out of her slumber. “Oh Sam, I must have drifted off. Are you ready to do me again?” “It appears so,” I laughed, “but I think we should rejoin the party. I don’t want George to get angry with me.” “Don’t worry about George,” she said. “He likes to share me with his friends. It makes him feel powerful. And he knows I like it and will make it up to him.” I was curious about their relationship. “There’s no jealousy?” “No, there’s no jealousy. We are the proverbial ships passing in the night, but who decided to tie up together for a while. You have to latch on to the opportunities that come your way. In a couple of years I will end my wild ways and go look for a life partner to settle down with. And I will have a couple of mil in the bank to help deal with life’s challenges. As for George, he will be tired of me by then and ready for a new filly. In the meantime, I am giving him the ride of his life. Anything he wants I give him—his wildest fantasies come to life. His money is well spent.” It made a lot sense to me. In a way I was doing the same thing with Vicky, except that Vicky was older and was getting something out of it besides money. Maybe Carolyn was too. I decided to try to find out.
“You said that you liked it. I don’t think the money is the only reason you are with George.” I ran my finger tips very lightly over her face. She laughed and wiggled her pussy against my gradually hardening cock. “You’ve got me there. I do like it. I like using my eyes and my body to get men all hot and bothered. It makes me feel super attractive and powerful. And when a man takes me the way you did it drives me crazy with lust. What can I say? I like sex.” “So you got off on the spanking.” Her incredible eyes lit up as she teased me. “Yea, I like being dominated and bossed around.” “Does George do that to you?” My finger tips traced the line of her eyebrows. “You bet he does. It really turns him on to make me do sexual things with him and others. Before we got here today I knew he was going to give me to you. I was looking forward to it.” The way she was looking at me was irresistible. “Those eyes of yours are really something,” I said. “What about the rest of me?” She squeezed my hips with her open thighs and shook her tits so the hard nipples punched at my chest. I grabbed her ass and pushed into her, pumping like a barnyard dog. I was totally out of control. “AHHH…. THAT’S IT SAM….. FUCK ME…. FUCK ME….” For the second time I lost myself in the deep pools of her eyes as my cock took over and sought its satisfaction in devouring her. I had more staying power this time and was aware that she climbed and descended several peaks before I finally exploded. The woman was truly a sex machine. I was still breathing heavily when I heard the door of my stateroom open. Carolyn was facing the door and whispered in my ear. “Don’t look now, but your personal assistant is here to see you.” “Come in Vickie,” I said, not bothering to turn over or unwind myself from Carolyn’s naked body. “Uhh… I am sorry to disturb you Sam, sir, but Mr. Stockwell is asking about you and his wife. He sent me to check on you.” “Well, as you can see I have been busy fucking his wife. Did you do your job and keep him happy.” “Oh yes. I got Felicia to help me.” “What did you do with my husband?” asked Carolyn in a tone that indicated she really didn’t care. “Well…..” “Come sit on the bed, Vickie, and tell us exactly what happened,” I commanded. There was just enough room on the edge of the bed for Vickie to sit beside me. I was still lying on my side facing away from her and looking into Carolyn’s amused eyes. Carolyn had one bare leg slung over my hips, and my cock was still in her. “Isn’t Carolyn beautiful?” I said to Vickie. “You can touch her if you want.” Chapter 24 – Vickie
I thought Carolyn was indeed beautiful. Her long slender legs were perfectly shaped and topped by the kind of small rounded ass that we women spend hours in the gym trying to develop. From where I was sitting I could see her sultry eyes dancing back and forth between Sam and me. Her leg twitched in open invitation for me to caress her. Sam was quiet, still recovering from his orgasm, but Carolyn seemed ready for more. With the tips of my fingers I traced a line along the back of her thigh and up over her ass. “Umm.. you have a nice touch Vickie,” she crooned. “Be careful or you’ll get me going again.” Sam put his finger on her mouth. “Vickie is my personal assistant and assists me in many ways,” he said softly. “Does she know how to please a woman?” “She’s learning. Aren’t you Vickie?” “Yes Sir,” I said, enjoying the way Carolyn was shivering at my touch. “Don’t be shy Vickie,” said Carolyn. “Put your fingers anywhere you feel like. But I do want to hear the details of how Felicia fucked my husband. You know our biggest sex organ is in our heads.” I rested my breasts on Sam’s back as I leaned over and slid my hand down between their naked bodies. My fingers ended up on the sensitive area at the top of Carolyn’s pussy. I let them roam around there as I told the story. “Felicia came in shortly after you left. She saw what I was doing to George and smiled like she wanted to join in. I noticed that she had changed out of her boat shoes into some high heeled sandals, and she had put on more makeup. She looked sexy as hell.” Sam stirred on the bed. “She is one hot little Latina,” he said wistfully. “What happened next?” My face hovered over Sam and Carolyn, and I spoke softly. “I told Felicia to strip for us. She stood right in front of George and rotated her hips. Then she began removing her shirt. She was not wearing a bra. She didn’t need one. Those boobs stood up all on their own.” “Tell us about her nipples,” said Sam. “Yea, do,” agreed Carolyn, snuggling against my hand. I was enjoying my story-telling role. “Did you ever drip wet sand into cone shaped castles on the beach? Well, if you did you know what Felicia’s tits and nipples look like. They are perfect little cones with pointy tops that stick out like the turrets on those sand castles.” “YUM..” purred Carolyn. “I didn’t know my new assistant was so literary,” observed Sam. “That is an enticing metaphor.” Carolyn pushed her breasts up against Sam’s chest. “I’ll bet George went for those hooters in a big way,” she said. “You’re right about that,” I said. “He palmed her ass and pulled her close where he could get his mouth on them. I felt his cock grow an inch in my hand.” “Goddd…”, sighed Carolyn. “George sucked on one nipple, and then the other, all the while reaching under her skirt and pulling down her panties. When he got them to her ankles, she stepped out of
them and straddled his lap. I could feel her wet pussy against my hand, which was still holding George’s cock.” “AHHH…..” Carolyn’s hips started moving up and down on Sam like she was trying to nail him to the bed. “I guided his cock into her and then sat back to watch the action. Felicia rode him hard and drove us both crazy with the noises she was making. He kept his mouth on her tits the whole time. It was incredible.” “OHHHH… I’M CUMMING AGAIN…”, wailed Carolyn. She was insatiable. Sam squirmed and helped her as best he could, but I could tell he was not ready. I smoothed his hair out of the way and put my tongue in his ear, which I could tell he really liked. Finally Carolyn rolled off of Sam and onto her back. Her body gleamed with a thin layer of sweat. She put her arm over her eyes and seemed to withdraw into another world. I thought maybe she was embarrassed by her over heated performance. Sam looked at her and then stretched out on his back beside where I was sitting. His cock was wet with Carolyn’s juices, and her gyrations had begun to rouse him from its weakened condition. “Lick me clean,” he said. I was already turned on by telling them about Felicia and by seeing Carolyn cum, so I had no problem putting my head down and dabbing Sam’s cock with my tongue. Every time he commanded me like that I felt a surge of heat in my loins, and this was no exception. Making his cock twitch and jump with my mouth was very arousing for me. “Ahhh… that’s it…. You are a good assistant. I think I’ll keep you a while.” “Thank you sir,” I said between licks. “But you have on too many clothes. Take off that shirt so Carolyn and I can admire your big tits.” I sat up and quickly undid the buttons on my shirt. At that point I was really excited and wanted to feel Sam’s hands on me, and Carolyn’s too. When my shirt was off Sam reached up and pulled my half bra down so that my tits popped out over the top. The bra held them up nicely, keeping them firm and pushing my long, hard nipples slightly upward. “Very nice,” he said. “Carolyn, open your eyes and look at these beauties.” Carolyn uncovered her eyes and looked at me. Her lips formed a sinister-looking smile. “They’re almost too big,” she said. “But I’ll bet they bounce nicely when your slap them.” My already damp panties got suddenly wetter. “Let’s see,” said Sam. “You whip them while she finishes cleaning me up. Vickie, you sit on the edge of the bed and I’ll stand beside it so my cock will be at the right level for you to do your job. That way Carolyn will have clear access to your tits.” “Yes Sir,” I said, too turned on to think of anything else to say. When he had me positioned like he wanted he took my hands and put them up on his shoulders. I was slightly bent with my mouth on his cock and my tits hanging free. He turned to Carolyn, “She’s all yours. Make her clean me good.” “Too bad I don’t have George’s little tit whip,” she said. “I’ll just have to make do with my hand. Maybe later you’ll give her to me again so I can share her with George and we can use our toys on her.”
“Of course,” said Sam. “She is here to please you in any way you wish.” WHAP… WHAP…. Carolyn used the tips of her fingers to slap my vulnerable tits as I swabbed Sam’s cock and balls with my tongue. He was still not totally hard, and I knew this could go on for a long time. In between slaps Carolyn pulled and pinched my nipples, just hard enough to reach the pain threshold. I began to moan. “Ummm… ahhh… “ “Feel up between her legs,” said Sam. “I’ll bet my bitch assistant is hot as a toasted marshmallow and just as squishy. Open your legs, Vickie.” I did as he said and felt Carolyn’s hand glide up the inside of my thigh. Her fingers reached my thong and slid under the edge like it wasn’t there. The area was well lubricated. “Whoa..” breathed Carolyn. “She is so ready.” “Poor girl hasn’t gotten hers yet today,” said Sam. “She has cleaned me pretty well. Why don’t you go ahead and finish her off.” “My pleasure. Lie back on the bed Vickie.” Sam pushed me back until I was lying on the bed with my legs dangling over the edge. Two pairs of hands went to work pulling up my skirt and easing my thong down my legs and off. The cool air of the air conditioned cabin flowed over my exposed pussy. I closed my eyes and moaned in anticipation. Carolyn must have gotten down on her knees between my legs, because I felt her face nuzzle up between my thighs and her hot breath blowing on me. She teased me for a few seconds and then thrust her tongue directly into my gaping pussy. I came immediately. “AAAHHHHH…. GODD YESSSSSS… SOOOO GOOOOOD…..” She continued licking me until I calmed. When I opened my eyes I saw Sam looking down on me, his cock now fully erect. I wanted him to fuck me, but Carolyn stood up and pulled my skirt down to cover my hungry pussy. “That’s enough for now, Sam,” she said. “We really should get dressed and go find George. Besides, I want to save you two for more fun later.” “OK,” laughed George. “I wouldn’t want anyone to think I lacked the discipline to control myself. Vickie, where do you think George is right now?” I sat up on the bed. “George said he wanted to go for a swim in the pool, and Felicia went to put on her bathing suit. That’s when George asked me to check on you.” “I want to see her in that bikini,” said Sam. “Let’s put on our suits and join them.” Chapter 25 – Sam It was mid afternoon and the sun was still burning hot when we arrived at the little pool on the top deck. Felicia was in the water, swimming leisurely on her back, her pointy tits just poking through the surface. George and Captain Mike were sitting in pool chairs watching her. I surmised that James was driving the boat. Vickie looked good in the brief bikini that Ginger had chosen for her. It gave her big tits lots of support and made the bellow out like flesh-colored balloons. When
George saw her he whispered to me that he would like to put his hot dog in those buns. I told him that wouldn’t be a problem. “Get out of the water Felicia,” said Captain Mike. “Let our guests see how good you look in that blue bikini.” Felicia smiled and climbed the short ladder. We all sat down and admired her as she strode around the edge of the pool, turning and posing so we could see her from every angle. Her body was gorgeous, and she knew it. The contrast between her light chocolate flesh and the iridescent blue bikini brought out every curve. Her nipples were hard and made prominent by the wet fabric that clung to them. “Come sit on my lap,” I said. “My hot skin will dry you off.” She smiled seductively and squirmed onto my lap. I was wearing my Speedo bathing suit, so there was a lot of hot skin to rub against her. “Oooo.. that feels good,” she sighed. “It does to me too,” I said. “Vickie, you should go sit on George.” “Let me get wet first,” she said and jumped from her chair into the pool. “Ah, that’s refreshing. Now I am ready to cool George down so he can enjoy the scenery.” The way she plopped on George’s lap was not designed to cool him down. She spread her legs and sat facing him, her tits inches from his face. He buried his nose between them and shook his head like a dog throwing off water. In the process one of her boobs popped out of her bikini and the nipple ended up in his mouth. “Oh my…” she squealed. I was delighted at the way my new assistant was entertaining my client. She seemed dedicated to making his visit so exciting that he would never consider taking his business elsewhere. And as for his wife, Carolyn, she was obviously enjoying watching her husband and playing with other women. Captain Mike had pulled his chair over next to hers and was rubbing suntan lotion on her thighs. Vickie looked over at me, and I nodded my approval. “You have passed every test, Vickie, and I am going to keep you. You can forget the thirty day trial period. In fact, I am giving you a raise.” “Thank you, Sam, Sir,” she said. “This is the perfect job for the new me. I will not disappoint you.” I smiled and pulled Felicia’s top down so I could get her pointy nip in my mouth. She squirmed and lifted her body to push more of her flesh between my hungry lips. One of her hands found the bulge in my Speedo and closed on it. I was still half turned on from my session with Vickie and Carolyn, and my cock twitched as she fingered it. “My, look what I found,” she announced to the group. “Let’s see,” said Carolyn, who had spread her legs so that Captain Mike could work the lotion high on her inner thighs. It was becoming obvious that Carolyn was a real voyeur. Mike moved his chair so he could watch with Felicia play with me, while at the same time getting a better angle on Carolyn’s pussy with his finger tips. A low moan came from her throat. Felicia was like a cauldron of bubbling sexual energy. She wiggled her tit one last time in my mouth and then slithered down my body to kneel between my legs. “You want to see? Okay, here it is.” The elastic on my Speedo was tight, but Felicia managed to drag the wet nylon over my rampant erection, giving me goose bumps in the process. I saw Carolyn lean
forward in her chair, whether to get a better look or to suck Captain Mike’s finger further into her I couldn’t tell. Felicia seized the base of my cock and waved it like a flag at a fourth of July parade. “See how big and stiff it is,” she said. “I’ll bet it tastes delicious.” With that she licked her lips and lowered them on the swollen tip. Her mouth was warm and wet, and her tongue was as soft and smooth as a flower petal. God it felt good! What followed could only be described as an orgy. George pulled Vickie’s bikini bottom aside and impaled her on his cock. Sam slowly finger fucked Carolyn as she stretched out and spread her legs. Felicia gave up putting on a show and concentrated on giving me a first class blow job. The fact that we could all watch each other ratcheted up our passions to the point where we seemed to be competing with each other for the loudest cries of pleasure. I saw the building ecstasy on Vickie’s face and egged her on. “Give it to him good, Vickie. Take him deep and milk him. That’s it.. shake those tits.” “Good god!” screamed George. “She’s incredible!” Chapter 26 -- Vickie I know how to pleasure a man when I really want to. And that afternoon I really wanted to. George was a sweet guy, not hung up on himself in spite of all his money. He liked sex and was willing to pay for it, as evidenced by the very generous deal he had made with Carolyn. Of course she was young and beautiful and could command a high price for giving herself completely to an older guy. In my case, I was on the edge of going over the hill and had to settle for what Sam had offered. But I was not complaining; I was getting well paid for doing what I wanted to anyway. And it made me feel good that George was so appreciative. I was determined to drive him up the wall. “You like this George, honey? You like the way my pussy is gripping you? What if I twist a little like this?” I have found that talking dirty to a man while fucking him generally results in a harder cock. You have to get into his head at the same time you are stimulating all those nerve endings. “If I don’t satisfy you I think I should be spanked, don’t you? That’s what Sam does to me. You could bend me over that rail over there and tie me down. Then I would be helpless to take whatever punishment you gave me. Would you like that George, baby?” “AHHH… God yes, I would like to punish you. Those big tits need a good whipping. Ohhh shit… what are you doing to me now?” “I’m pulling up so that I can feel the tip of your cock on my clit. A girl needs to take her pleasure too.” By reaching behind and under my ass I was able to wrap my fingers around his cock and guide the tip to where I wanted it. I used it like a pencil with an eraser on the end to rub the spot that I knew would set me off. George was on the verge and I wanted us to cum together. “OH George, that’s so good. I’m cummmminnng… Fuck me! Fuck me!”
With my orgasm surging through my system I lowered myself on his cock and thrashed around on his lap like a gigged fish. He howled and met my every thrust, sending a warm gusher deep into my womb. The fact that I had given him so much pleasure at the same time I had satisfied myself sent a warm glow through my system. As I lay back in his arms I reviewed all the things that had happened to me in the past few days. I had gone from a quote--normal, educated, sophisticated, conservative American woman--to what I was sure my former friends would have called a complete slut. There I was sitting essentially naked on the lap of a man I had known only a few hours, just having fucked his brains out as part of what could only be described as a wild orgy. All this in broad daylight on the deck of a boat, clearly visible from the houses along the shore. And you know what? I didn’t care. In fact I wanted more. Chapter 27—Sam All I can say is that I was amazed at Vickie’s behavior that afternoon. What had begun as a job interview and resulted in an explosion of sexuality. I guess that’s what happens when a naturally hot female bottles up all that energy for so many years. All it takes is a dominant male in a strong enough position to insist that she let go, and then make sure her right buttons get pushed. Clearly I had done that with Vickie. The other thing I came to realize that day was that I really liked her. Her quick intelligence, sense of humor, and willingness to abandon all pretenses when it came to sex were very appealing to me. And the fact that she got so turned on by being submissive fit my needs like the proverbial glove. It is really too bad that my wife of many years has totally lost interest in sex of any kind. We were good together for a while, but for the last ten years she has been as dry as unbuttered toast. Why Vickie, who is about the same age as my wife, is a hottie, while my wife is the opposite, is a mystery—in fact it is a nasty trick of Mother Nature. Fortunately my wife is realistic and unselfish. She knows that I still need sex, and lots of it, and she is willing to look the other way as long as I don’t rub her nose in it. I’ve had many discreet affairs over the years, including the ongoing one with Susan in the office, but never had what could be called a mistress, a woman close to my own age with whom I could have a real relationship. That afternoon on the boat I began to think about what it would be like to have a woman like Vickie as a mistress. If I could work it so my wife accepted it, it would fill a big void in my life, and I could still maintain my marriage for the sake of our family and my position in the community. Of course it was way too soon to be doing anything like that with Vickie. We had known each other only a few days. She probably thought I was a cruel sex maniac, who was taking advantage of her in the worst way. Still…. Chapter 28 – Vickie When I think back on that first week of working for Sam I wonder how our relationship ever grew out of that sexual maelstrom. The weekend on the boat was non
stop group sex--on the deck, on the private beach, in the hot tub, even in the case of James and Felicia on a bouncing jet ski. The only respite was at night, lying exhausted in our own staterooms, and there I began to get an inkling of the kind of man Sam really was. Once he had established his dominance over me he relaxed and became a tender lover, holding me and sharing his feelings and vulnerabilities. By the end of the weekend we had reached the point where we could laugh at each other and ourselves, and we realized we enjoyed being together. Of course it took many weeks of close contact before we acknowledged that there was more to our relationship than boss and submissive employee. But gradually that happened. Sam even nudged Susan out of the picture, and she soon quit to go to work for one of our clients. After that I was Sam’s main confidant at work, doing whatever was necessary to help him land clients. Now I am his mistress. His wife has accepted, and even blessed the situation. I make sure never to embarrass her. Sam and I travel together, but I go along under the guise of being his indispensable personal assistant, and this is all the cover his wife needs. A year ago I was thinking my life was essentially over. Now I know that if you are willing to let yourself go and take some risks, it is never too late to get the most out of life. Your karma is there; you just have to put yourself in harmony with it and let it resonate. It’s never too late.
THE END ###
