Boss Lady

Boss Lady

by Tim Roberts

Diane was the first female supervisor I had ever had. The first day she arrived in the office I was stunned by how beautiful she was; early 30's, long brown hair and brown eyes, about 5'6", and slender with a great build. Yes, she was truly very pretty. But what really turned me on was the way she dressed and how she handled herself in the office. She managed to do a real good job of looking business-like and sexy at the same time, wearing suits but with the dress cut short and nice strappy high heels. Diane's style was pretty direct but also light and playful. But she seemed to enjoy giving orders and quickly established herself as the boss in fact as well as in name.

I was very attracted to her physically and found it vaguely satisfying to have her as my supervisor. It gradually dawned on me that her take-charge manner made her even more attractive to me. But I still found it hard to adjust to working for a woman. I resisted doing stuff she wanted and started missing deadlines on important projects. Since I was the only male reporting to her, I really felt isolated. And some days, when she wore something especially tantalizing I was so distracted I couldn't concentrate for hours afterward. My God, those legs and tight ass, how I wanted to get my hands on her!

Finally, about a month after she arrived, Diane called me into her office for a one-on-one talk about my performance. She said she thought that I was having difficulty because I could only think about her as a woman, not as my boss. I admitted that I found her very attractive.

"I find that you're no different from the other men I've supervised, Tim. You lack respect and you are insubordinate. And your mind is constantly in the gutter. Don't deny it. I've noticed the leering looks from you on several occasions. But you know that I control your future here, don't you?"

"Yes, Diane"

"Well, good, that's a start. Now, what I find works really well with a recalcitrant male subordinate is some private tutoring after hours. It's not optional, if you want to get along with me, that is."

She handed me a piece of paper with an address on it and said she expected to see me there the following Wednesday at 7:00 pm.

"That's 7:00 pm sharp, Tim. Is this all clear?"

"Yes Diane, I guess," I responded.

"Don't worry" she replied, "with my help, you'll become unconfused very quickly and we will get along much, much better. Now you are dismissed. Back to work!"

Diane's latest instructions really did leave me confused, so I was looking forward to the "tutorial" as she called it. My fondest hope, of course, was that she was really just coming on to me and that I was about to get lucky. After a lot of vacillation, I went out and bought some nice perfume to bring on Wednesday. That would at least make it clear that I was interested in being a lot more than just her "subordinate".

The townhouse she lived in was in a nice neighborhood. Diane was all smiles as she let me in and invited me to the living room. She wore the same navy blue suit she had on at work that day, but she had removed her jacket. The top button of her blouse was open, showing an exciting bit of cleavage. Diane was clearly aware of the effect she had on me. After I sat on the sofa she stood in front of me, looked down at me, and smiled. "Like what you see?"

"Yea, I sure do. Diane, you're, ah, well. I find you very attractive. And I ...." I was so embarrassed I didn't know what to say.

With an amused grin on her face, she waited as I squirmed a bit. Finally I decided that actions would speak louder than words--big mistake as it turned out. Anyway, I reached up and put my hand on her leg. At this she grabbed my tie, pulled my head up and angrily informed me that I was never to touch her without her permission. I started to apologize but she stopped me.

"I'm not interested in apologies. You see, Tim, I have special rules for men--I expect to be treated like a lady at all times. I am very special and deserve to be treated accordingly. And men who work for me have to learn have lots of rules if they want to please the boss."

She moved over and sat in the side chair next to the sofa. "The first rule is that since I am your superior and you are my subordinate, you will kneel when in my presence. After all, subordinate does mean lower or under, doesn't it?"

"Yes, Diane, but, I…"

"Do it" she interrupted sharply, pointing to the floor in front of her.

I was totally taken aback and complied.

"Now, for the next hour or so you will start learning to respect me and obey me the way your supposed to. First, I have a little task for you. One of my garters came loose and I want you to help me reattach it." As she spoke, she stood up and slowly raised her skirt on one side to reveal the loose garter. My cock got so hard I was afraid she would see it through my pants.

"You have permission to touch my leg in order to reattach my garter."

Nervously I fumbled with the garter. She giggled at my awkwardness and observed that I seemed to need more practice. This was an immensely pleasurable task, so I was sorry that only one garter had come loose. Above the top of her stockings I could see her pretty white thighs and even a bit of the black panties she wore. It was difficult to control myself. I fantasized about being able to dress or undress her. What a queen she was!

When I was finished she sat down again. "Now, why don't you stay on your knees. I like you on your knees, and besides, I know YOU like it because the view is SO-O-O good!" As she said this, she crossed her legs and, with a flourish, carefully slid her skirt up so that the garters on both her legs were clearly visible. I was so stunned I couldn't believe what was happening. This woman certainly was different--more than a cock tease, a lot more.

Although I felt a bit sheepish, I stayed on my knees and positioned myself before her.

"You like my beautiful legs in my sexy stockings and garters, don't you Tim?"

"Yea, Diane, who wouldn't? You're a real turn on."

She prompted me to tell her in great detail what I was thinking, what I thought about her, and why I found her to be attractive. All my emotions just came out in a torrent of words. I told her how she attracted me physically and also that she seemed different. Finally, I shyly admitted that I wanted to have sex with her in the worst way.

"So you want it bad, huh, well that's typical of males. You can desire me all you want. I don't care. The fact is, I'm your boss. Actually, I find that little boys become so much more agreeable and compliant when they're needy like that. And I find it a bit amusing watching you try to hide this." As she spoke, she placed the tip of her left heel on top of the bulge between my legs.

I let out a low moan of frustrated desire. Any contact from her felt so good I couldn't help myself. I involuntarily started to push my pelvis up toward her shoe. "No, no, control yourself. I want you to remain perfectly still. You must learn control when you're in my presence."

I tried mightily to obey. She slowly brushed her heel in circles over my crotch area. I thought I would come right then and there but she removed her heel just in time.

"Good, Tim. But I see you need to learn more self-control. Now I want you to get me something to drink--how about a diet coke on ice. Just go to the kitchen and help yourself. Get something for yourself too. And there's a tray on the countertop next to the fridge. You can serve it to me on that. Now hurry, I'm thirsty."

When I came back I found Diane stretched out on the couch but sitting up, with her back against one arm. She smiled prettily as I leaned down and offered her the drink on the tray.

She had me kneel again in front of the couch. We chatted and sipped our drinks for a few minutes.

"So, you're starting to learn how I like men to behave around me. You obviously enjoy it or you wouldn't have such a hard on. What you really are, Tim, like all men who work for me, is my slave.

There was a brief silence. I looked down in embarassment.

She continued: "I require total obedience and submission. If you want to continue working for me it be on my terms--you, Tim as my loyal, obedient slave, and me as your mistress, teacher and guide. I will take you into a new world, Tim, where men serve women. I am a strict but fair mistress. Your training will consist of regular punishment and correction, and you will learn total humility by obeying all my wishes. Your reward will be the privilege of serving me and pleasing me. If you are a good boy, I may occasionally allow you sexual release."

"Do you agree to become my slave?"

"Yes, I do."

"From now on, when we are alone, either here or at work, you will address me as 'My Lady". Now I want you to properly acknowledge me and then kiss each of my feet to show your respect."

She had me and she knew it. There was no choice,

"Yes, My Lady, I obediently replied. And I planted a kiss on each of her feet in their sexy heels.

She led me upstairs to a small, barely furnished room next to the bedroom. In one corner was a rack containing a huge array of whips, paddles, and other implements that I had never seen but whose purpose was easy to guess. A big wicker fan chair, like the kind that the queen uses in the movies, was in the opposite corner. She instructed me to strip completely naked and kneel facing the chair. I was to put my forehead on the floor, legs spread shoulder width apart, and hands on the floor at my sides.

"I expect to find you to be ready and in that exact position when I return. You are not to move without my permission." She left the room.

I stripped, assumed the position she had indicated, and patiently waited. A good ten minutes later I heard her enter the room. Without thinking, I looked up as she approached--big mistake! She was an eyeful--she had changed into a long black silk robe. It was open at the top to show some cleavage, and she wore high heels and stockings. But I had been disobedient by moving without her permission.

She was clearly very displeased but in an even tone of voice, she firmly established who was in charge. "You disobeyed and must be punished. You will get a taste of the hot pain that your mistress has in store for slaves who displease her." She handed me some ankle and wrist cuffs and instructed me to put them on. Grabbing my left ear, she led me to her 'whipping horse' in the corner. I bent over it and she secured my ankles and wrists to anchors at the bottom of each leg. Now I was completely helpless.

Without a word she proceeded to beat me--a total of 10 strokes, 5 for each infraction. She taught me the ritual I was to follow whenever being corrected; first, ask her for each stroke, and then thank her after it was administered. And if I forgot any part, I would get two more penalty strokes. She started with a heavy paddle and finished up the last five with a riding crop. The pain built gradually and seemed to go deeper and deeper with each stroke. She hit me pretty hard and didn't seem concerned at all when I yelled out in pain. My pleas for mercy fell on deaf ears.

She released me and sat down in her chair. I started to follow her but she turned and, pushing the tip of the crop into my chest, told me to await her command.

She settled comfortably into the chair. Tapping the crop lightly on the side of the chair, she said "Okay, Tim, you may crawl over here and beg your mistress's forgiveness."

I was required to first thank her profusely for correcting me. Only then was I to offer repeated apologies and promises not to repeat my misdeeds. All the while, she held the crop across her lap, an unspoken threat of further punishment if I screwed up. It was easy for me to be totally sincere, with my ass still burning from the whipping I had just received. I didn't want to get on her wrong side again any time soon. Of course, I didn't know it then but, as I learned later, I didn't have to misbehave to merit a beating. Diane would punish or torment me whenever she felt like indulging her sadistic streak. And most surprising of all, I came to like it because I was pleasing my mistress and indulging my own need to submit to this beautiful dominatrix.

Diane allowed me to sit comfortably on the floor while she explained her training program. My ass was so sore I had to sit sideways. She totally ignored my rock hard cock. I self-consciously tried to hide it under my hand.

"Let me tell you what I require new slave candidates to do. They must go through a training course that I have set up. This covers all aspects of what it takes to serve me and please me. It will teach you to obey and submit, while also pleasing and amusing me. This will give you a chance to show how sincere you are about becoming my slave. And I get a chance to evaluate you and decide if I want to accept you into my stable.

"There will be five lessons, each of which corresponds to a training session covering a specific topic. The first lesson, which we are doing today, covers the basic rules of obedience, servitude and respect. You will be expected to adhere to these rules throughout the rest of your training. The second lesson will introduce you to bondage and discipline and what I call my training toys. Now most new slaves really enjoy lessons three and four because they give you the chance to have a little more physical contact with your mistress. Let me explain. The theme of lesson three is worship and amusement. You will learn some basic body worship rituals and how to amuse me by being really servile and being humiliated, or by just serving as my plaything. And don't misunderstand me, Tim, there's absolutely no sexual contact. When I say plaything, I mean more like my trained pet dog.

"In lesson four, I will teach you how to take pain in exchange for pleasure. I will allow you certain pleasure but first you must earn it by submitting and enduring a good deal of pain. After all, this is only fair, don't you think, Tim?"

"Yes, My Lady, I guess so."

"Well, after lesson four I'm sure you'll be answering with a strong yes."

"And finally, in the fifth lesson I will give you a 'final exam", which will involve your being loaned out to serve one of my girlfriends who is also a domme. She will evaluate your training and give me a final report. And if she fails you, you will be severely punished and then required to start over on remedial training from the beginning."

"Now, let's get on with today's lesson. The topic is my basic rules for slaves. They fall into five types of behavior that I require--respect, obey, submit, endure, and serve. Since all ladies love roses, and your mistress is no exception, I find it amusing that the first letters of my five behaviors spell the word ROSES. And we all know that feeble-minded males need lots of help remembering, don't they, Tim?"

"Yes, they do." Hastily, I added "My Lady"

"Let's start with 'Respect'. Slaves should always exhibit the most proper manners toward the superior female. Since I am your mistress and you are my slave, I have even stricter standards. First, as you've noticed, slaves are always naked in my presence. It reminds you of your status and makes your body completely available for whatever I want to do to it. You will always address me with a respectful tone of voice. I don't want to hear 'I want' or ' I need' from you. In order to be respectful you must be humble and submissive. So what I want is 'My Lady, may I please' or 'My Lady, I humbly request'. Also, I suggest that you never interrupt me and never disagree or question me. You are not to touch me or any article of my clothing without my permission. Any infraction may be punished but this last one is guaranteed to

result in severe correction. And I think you have an idea by now of what that means."

"Is everything clear so far, Tim?"

"Yes, My Lady, very clear."

" 'Obey' is pretty simple. I expect instant obedience when I tell you to do something. I don't want to see any questioning or disagreement. The only question you may ask is to make sure you understand what I want you to do. I am in control at all times when you are in my presence.

"The next behavior is 'Submit'. This has to do a little with obedience but it's more a question of attitude. It's a privilege to be in my presence. Whenever I grant you that privilege, it's to meet MY needs, not yours. That means you must learn to be always thinking of how to please me and serve me. The hardest thing for males to learn is how not to think about their cocks--or with their cocks!!! Your need to cum is of no concern to me. In fact, you will learn that you cock and balls belong to me for my amusement. Your purpose here is to amuse me, serve me, and be my toy. There are a lot of things I will have you do to teach you what 'Submit' means.

"What's the next one, Tim?"

"Endure, My Lady."

"Very good, Tim. Now let me give you a little hands on demonstration of this behavior. Stand up and clasp your hands behind your back! "

She stood up and got a pair of handcuffs from the rack. She placed them on my wrists. I was now completely vulnerable for her 'little demonstration'.

She stood in front of me and grabbed my balls with her hand and squeezed them. As the pain hit me, she ordered me to stay still. This, she said, was endurance. Could I endure the pain in my balls? If I did, it would please her greatly, she explained. If I failed to endure, not only would I earn her displeasure, but maybe a whipping as well.

"These balls and this cock belong to me, don't they Tim? "

"Yes, My Lady."

"Then I can do whatever I want with them. Go fetch me that rawhide lace and the short little penis whip, the one with the red handle. Since your hands still cuffed you can bring them to me in your teeth."

"Yes, My Lady, as you wish."

I hurried over to the rack. I grabbed the rawhide lace with my hands, clutched the penis whip in my mouth, and brought them to her. She proceeded to tie the rawhide tightly around my balls, wrapping it several times between them, and then around my shaft up to the head. My cock bulged out, the color of dark purple, and my balls looked like to ripe plums. Then, while staring straight into my eyes, she methodically beat my cock with the penis whip, a little whip about a foot long. Gradually the pain intensified. She was hitting harder each time. Clearly she enjoyed dishing out the pain and seemed to delight in my efforts to take it without moving or crying out, even though I did break position after about a half dozen strokes.

After tormenting me in this manner for a while (or should I say teaching me endurance), Diane sat down and had me kneel at her feet again. She explained the last behavior, 'Serve'. This had to do with real service, like giving her a back massage or a pedicure, washing her lingerie, or cleaning her apartment. She indicated that the kind of service she might require would depend on her mood, as well as my ability to perform satisfactorily. During my training, what counted most was honest effort on my part to serve her and to try to do it properly. As long as I displayed the proper motivation, respect, and submissive attitude she would not punish me for mistakes. Eventually, if I was accepted into her stable of slaves, I would be expected to become proficient in all of these tasks.

Diane then informed me that the lesson was almost over and that she was going to use the last part to reinforce my training in basic submission. I was forced to beg for the privilege of having an orgasm. She made me grovel and humiliate myself to "show my sincerity" as she put it. When she finally relented, I was allowed to cum but only under her total control. With the crop she set the pace to which I was permitted to stroke my cock. She stopped suddenly several times, giggling at the intense frustration on my face. The first time I continued pumping and she angrily slashed the crop across my back to make me stop.

The threat that got my immediate attention was that she would send me home still hard, to take a cold shower. Finally, My Lady allowed me to cum. I was forced to catch it in my hand and lick it up as she looked on with a smile of triumph. She obviously reveled in her ability to use my lust for her and my submissive nature as a tool for humiliating and controlling me.

Two days later I got a letter from her with the following instruction sheet inside.

ETIQUETTE COMMANDS AND POSITIONS FOR SLAVES OF LADY DIANE

Note to slaves from Lady Diane:

The purpose of these commands and positions is to demonstrate to Me your absolute obedience and submissiveness to My will, as well as your profound respect for your Mistress. As for you, you should enjoy learning to respond properly to these commands since this will please your Mistress to no end. Failure to demonstrate good slave etiquette will be punished severely; therefore, there is a very practical reason for you to apply yourself to learning these commands. The prescribed penalty for failure to execute--quickly AND correctly-- is listed under each command. This number represents demerits. They will be administered as strokes of a whip, as minutes of chastisement involving a certain item of restraint or chastisement, or any combination thereof. Mistress is strict but fair.

COMMAND	EXPECTED RESPONSE	PURPOSE/PENALTY
"Position"	Kneel with legs spread wider than shoulder width, palms on floor, and forehead to floor.	Suitable for receiving punishment or merely to demonstrate submission. (10)
"Squat"	Squat with legs open wider than shoulder width, hands behind head, elbows out.	Usually for receiving chastisement (10)
"Follow"	On all fours, follow Mistress	(5)
"Heel"	Lie on back on floor before Mistress, underneath Mistress' left heel, head gently placing heel on face.	Demonstrates trust and submission (5)
"Butterfly"	Lie on back on floor with legs spread as wide as possible, arms folded and hands tucked under back.	Receiving punishment. (10)
"Feet"	Kneel and worship Mistress' shoes and feet. Kiss feet first and then cover complete surface of shoes with tongue licking. Next, if Mistress is wearing heels, suck each one deeply. However, Mistress' permission must be obtained first by saying: 'I humbly beg for the privilege of worshipping Your lovely heels. Would it please You, Lady Diane?	Demonstrate submission and proper respect. (15)
"Worship"	Kneel before Mistress, kiss each foot once; then on each leg, plant soft, respectful kisses every six inches or so up to mid-thigh. Finally, kiss each of Mistress' hands and thank her.	Demonstrate respect and obedience. (20)

 

She instructed me to memorize these positions and rules. The submission they imposed on me, and the punishments that resulted from my imperfect attempts to serve, formed the basis for my new life as Lady Diane's slave. Not too bad for a true submissive!