The Personal Assistant

Madam sensed a slight movement on my part.

"You're not getting hard on me, are you James?" she teased. "Is it the flogging that turns you on or the licking of my boots or is it both?"

"Oh god," was all I could murmur.

"Well, to continue my little story, one day after my usual ride when I was flogging Jay with particular gusto, he had a fatal heart attack. "Be assured James, he died in ecstasy," she laughed. Naturally, the circumstances of his death could have been a bit of a scandal, especially considering how rich he was. But the coroner had a son who needed a little help to get into Swarthmore and the undertaker gladly accepted a handsome bonus from an aggrieved widow. I do love to have things go my way, always."

I said nothing, stunned by her confession.

"Why so silent, James? "You were so articulate at dinner tonight James. Now let me turn over and show me if your tongue is good for anything else.

I was delirious with joy and lust. From the first day that Vickie had interviewed me I had fantasized about burying my head between those lush thighs and penetrating that heart of her femininity with my tongue. I was drunk with desire."

"You are a goddess, madam," I moaned. "I worship you completely. I can't get enough of you. This is heaven."

Vickie only wrapped her legs around my head in response, squeezing hard every time she had an organism.

At last she released her hold on me and I took this as a sign she wanted me to move up and penetrate her.

Big mistake!

"What are you doing? If you ever dare to interrupt my pleasure again I will punish you severely. I was just trying to reach my cell phone."

And with that she pushed my head back down between her legs and punched in a number.

"Hi Tina my sweet. I know it's late but I just couldn't sleep. I wanted to tell you what a perfectly marvelous dinner party you threw tonight and how stimulating it was talking with you on the terrace. What am I doing right now? Would you believe I've just started a conditioning session with James? Oh yes, it's going quite well but I can tell that I have my work cut out."

"I must teach him humility, obedience, and self-control. How will I do that? Oh I have my methods. I won't keep you darling. Thank you, again, for such a stimulating evening and here's hoping I can have you over soon to participate in a little threesome. Ta,ta."

Putting the phone down, Vickie at last looked down at me, "Take down your shorts, James and roll over. I'm going to have a little fun with you."

Once on my back Vickie glanced at my enormous erection. "My, my, what do we have here?"

Reaching for her holder she provocatively inserted a cigarette just as she had in my interview, except this time she bent forward to get a light from the candle on the bedside table. She inhaled deeply, moved her lips to within inches of mine and blew a strong, heavy jet of white smoke directly into my mouth.

"You are fascinated by my smoking, aren't you James?" she teased.

"Yes Madame, I am," I murmured. She inhaled deeply again and, turning to my rigid cock, covered it with a stream of smoke and began to gently stroke it with her holder. I was going out of my mind.

"You do like it when I blow smoke into your mouth, don't you James?"

"God, I love it!"

"Then I'm sure you'll like this even more. Open your mouth."

And as I did, she flicked the ash from her cigarette onto my tongue.

"This is another little service I expect you to perform for me whenever I demand it. I love to use a man's mouth as my ashtray. It's so over the top, so kinky, and it's a wonderful way to teach you humility."

She turned her attention back to my upright, aching member, again stroking the shaft and the head with her holder.

"Tell me James, did your mother ever do this?"

"I think she did once, I mumbled."

"You are a terrible liar, James. If she teased you once this way she teased you a hundred times. Some mothers love to bring their son's little soldiers to attention and then torment them just like the tourists like to torment those royal guards with the busbies at Buckingham Palace. And would she bring you to climax, James? Obviously yes, because you're speechless and blushing. But I must warn you James, you must never—I mean never—climax without my permission. Because if you do I will punish you severely. We will practice and practice until you have learned total self-control. Is that clear?"

As she talked she continued to stroke me with her holder, pausing now and then to inhale and blow the smoke into my mouth, always moving her lips so that they almost touched mine.

"Now let's talked about your incestuous fantasies. You know such thoughts are very, very wicked James and if you shoot off while I'm stroking you I'll assume it's because you're thinking of your mother and not me, and you'll be punished. You must understand James that I torment you for my pleasure, not yours."

Vickie continued to minister to me, now and then flicking ashes and blowing smoke into my mouth.

"You're not about to come, are you James?" she finally declared in mock surprise. "Could that be a little stream of semen I see oozing from your cock?"

A stream of white smoke from her pursed lips engulfed my cock and I went off with a scream like a Roman candle.

"Oh James, you are such a bad boy. Hold out your hand."

And with that she removed her cigarette from her holder and ground it into my palm.

"I warned you James, I always punish bad behavior. Really we must really work on your self-control. Now get out of my sight and clean yourself up."

After that session I could not sleep, not so much because of the burn on my palm—it really wasn't that bad—but because I could not stop obsessing about Vickie. I was totally in her thrall. What a subtle, sophisticated, and irresistible sadist she was! In just one unbelievable session she had begun to condition me to associate my subservience and torment with her pleasure. I was ready to endure anything if only it delighted this goddess. "Oh Vickie, torture me to your heart's content; I will worship you for it!"

Over the next few weeks Vickie's moods ranged from mellow, to provocative, to downright horny. Some evenings she would call me into her bedroom to lie beside her on her bed while she watched a movie. She would prop herself up with pillows and have me lay on my back while she smoked languorously with her beautiful holder, totally absorbed in what she was watching and seemly totally indifferent to my presence. Now and then, however, she would lean over, blow a stream of smoke into my mouth, flick an ash into my tongue, and tease me saying, "You have such a perfect mouth for an ashtray" or "I hope this isn't turning you on because all I have in mind tonight is enjoying this movie."

Her sadism wasn't just physical. One morning at breakfast shortly thereafter she told me that I was to escort her to a dinner dance that night and two wear my tux. However, instead of being seated together at dinner, the hostess put Vickie next to some young Italian playboy who Vickie began to assiduously seduce. I was banished to a corner table and was forced to watch as Vickie put on a full court press. Returning to the table after several close and sensuous dances with the bewitched Roberto, she motioned to me that she wanted a cigarette, which I dutifully inserted, into her holder. But Roberto was quicker than I with his lighter—Damn him! I tried to appear as the perfect personal assistant, asking her if there was anything else I could get her, but she waved me away without a word. I could see her now and then steal an amusing glance at me sulking at my table. And I could see her—the seductive bitch! —blowing smoke and whispering into Roberto's ear.

Near midnight she summoned me over again and said that Roberto was going to take her home and that I was free to leave. I drove to the mansion in a fury. "What a bitch, what a bitch, what a cruel bitch" kept running obsessively through my head as I lay sweating, wide-awake in my bed.

I had probably been in this state for half an hour when I heard the excited voices of Vickie and Roberto over the intercom. I wanted to rip the damn thing out of the wall but found myself transfixed by what I heard.

After what were obvious sounds of mutual undressing, Vickie cried out,

"Do you want me, Roberto?"

"Oh god how I want you Vickie" came back that damn accented voice.

"Then come inside me, my Italian stallion, and fuck my brains out!"

Wild animal noises until Roberto at last cried,

"I'm coming, I'm coming to you Vickie."

Shrieks of delight and then after a pause Vickie's commanding voice:

"While you're recharging your batteries Roberto you can pleasure me while I have a cigarette."

At that request I died a thousand deaths. Foolish me thinking that that sacred pussy was mine alone to savor. Bitch, bitch, bitch!

After about five minutes I hear Vickie saying,

"I can see that your canon is still not loaded. Let me see what I can do."

Roberto's response was a cry of delight and surprise: "My god, what are you doing Vickie?"

"Darling, anyone woman can suck a cock, but how many know how to massage your prostate at the same time. I guarantee that when I'm finished you'll hardly be able to keep from shooting off."

Indeed, Vickie's skillful lips and finger apparently worked their magic because I soon heard Vickie exclaim,

"Now that's more like it. Let's see if you can't run a marathon with that baton."

Poor Roberto tried his best, but Vickie's and sensuality soon overwhelmed him.

"I can't go on, Vickie," and then he muttered something in Italian.

"So much promise," laughed Vickie, "so little performance. If a man can't keep hard all night I'm not really interested in him. Now get dressed and leave. I want to sleep."

Next morning, as I arrived at what had become our customary breakfast on the terrace, Vickie teased me,

"Do I detect you having trouble bending your right arm? Could it be a case of tennis elbow by any chance?"

"What do you think," I answered in a surly tone. Her anger was instantaneous.

"Never, never, speak to me in a tone like that again. I know exactly what you did in your room last. You spanked the monkey good. Well, I once told you that you must never come without my explicit permission. Now, I'm going to have to spank you, no, thrash you, in a way you'll never forget. Be waiting at the stable when I finish my ride this afternoon."

I was wild with anticipation as the morning and early afternoon hours dragged by. I'm sure that Vickie came back to the stable later than usual just to torment me.

Finally she arrived, dismounted, gave the reins of her mount to the stable boy and told him to take her horse for a long cool-down walk. Vickie looked magnificent: small beads of sweat on her forehead and upper lip, a white silk blouse that nicely revealed her sweating breasts, classic jodhpurs and black riding boots and, most alluring of all, a crop in her gloved right hand that she kept impatiently slapping into her other hand.

"Follow me," she ordered as she marched toward the tack room. She locked the door behind us and pointed with her crop to a sawhorse which held a saddle.

"Take that off and bend over the sawhorse, and don't you dare let go of that bar between the legs."

With that she reached around, loosened the belt on my pants, pulled them down, and went to work with her crop.

" You're not moaning, James, I like that. It inspires me to flog you even harder. There's nothing I like better than a well tenderized ass."

And well tenderize my ass she did, with great relish and untiring strokes. At last, satisfied with the bloody blisters she had raised, she stopped and I heard her open a box, take out something, and then apparently strap it around her waist and legs. My next sensation was of a large, greasy, flesh-like object penetrating my rectum.

"Now you're going to see what it feels like to be fucked over—fucked over and stroked at the same time."

And as she moved her dildo vigorously back and forth in my rectum she began to stroke cock, gently at first, but then with increasing intensity.

"I thought it would be fun to condition you differently for once. And if you dare shoot off, I will punish you unmercifully."

I was totally overwhelmed and completely at the mercy of my beloved mistress. I held out for as long as I could, but Vickie's incessant thrusting and simultaneous stroking was ultimately irresistible and my whole body shook with spasms of uncontrollable joy.

Vickie was enraged.

"I warned you what would happen if you shot off without my permission. When I get through with my cat-o-nine tails you'll think that my crop felt like a wet noodle."

But at that moment Vickie's cell phone rang. Perhaps, inadvertently, she had left it on. But she glanced at the screen and immediately answered.

"You are so lucky James. My daughter is in a bit of trouble and I have to leave immediately. I'll take the Mercedes myself and be back when I'm back. And for god's sake get yourself cleaned up. You look a mess."

Although as Vickie's personal assistant I was privy to virtually all her personal papers, I knew nothing about her daughter except that she existed. Her son, of course, had been the subject of Vickie's special attention—the type of seduction I was familiar with but had largely suppressed until I began to confess my dark desires under Vickie's skillful interrogation.

When Vickie returned two days later she said nothing about her daughter but ordered me to prepare for our usual routine. This was Vickie's favorite form of conditioning. After a swim or riding, she would go to her sauna, emerge naked, lay face down on the massage table, and have me give her a deep massage. I was to always to wear boxer shorts so that when I was astride her, I would not, as she once told me, "be tempted to ram by cock between her luscious buttocks." Suitably aroused, Vickie would rise, order me to light her holdered cigarette, take my shorts off, and lie on my back. She'd then begin her mesmerizing ritual: with her lips nearly touching mine she would blow a heavy stream of delicious white smoke into my mouth. Then turning to my my-now rigid penis, she would tease it unmercifully, lightly caressing it with her holder and wreathing it in smoke. When the ash on her cigarette was sufficiently long, she would flick it in my mouth. These three erotic gestures—the smoke and ashes in my mouth and the stroking of my cock—would drive me insane. But, slowly, I learned to control my ejaculation. Of course, my growing self-control only intensified Vickie's efforts to bring me to climax.

One session, when I had managed to stay erect after she had finished one cigarette, she lit another and taunted,

" Are you really totally devoted to me, James?"

"Oh, Madame, I am. I am your slave."

"I not sure that I believe you, James. If you were really my slave I would brand you. Would you like that James? Would you like me to slowly brand you with my cigarette? That would be such a turn on for me."

"I live for your pleasure, Madame. You must believe me."

"We'll see, we'll see. Tomorrow evening, we'll have a cozy dinner somewhere where we can dance and then we'll go to my little gymnasium. You may have noticed the table with the tie-down straps. Of course, if you really wanted to be my slave you wouldn't need them, but then you might not be able to stand it if I got really inventive."

Dinner was on the large patio of a swanky club by a private lake. Vickie was dressed in a beautifully tailored white pants suits with a matching turban—a touch that I had never seen before but which only enhanced her elegance. She was the most stunning 60-year old woman I had ever seen. No, that's not right, she was the most stunning woman of any age I had ever seen. Thank god, Vickie was not into botox. I loved the crow's feet that framed her blue eyes and the tiny vertical wrinkles on her upper lip that older women often develop. Her neck, framed by a simple double strand of pearls, was remarkably firm. She radiated sensuality, power, and supreme self-confidence.

As soon as we were seated she asked for a cigarette. White suit, white turban, dainty pearl earrings, and a long white cigarette in a gold and ivory Denicotea holder—she was breathtaking and her smoke mingled with her perfume was intoxicating.

"I love your turban," I offered.

"It gives me an air of authority, don't you think, James?"

"I agree completely, Madame."

Vickie quickly sensed that I wanted to say something else.

"Out with it, James!"

"When you smoke with your holder, Madame, I have an irresistible urge to have you use my mouth as your ashtray."

"Well, I'd be disappointed if you didn't after all the conditioning sessions we've had."

We ordered—or I should say, Vickie ordered for both of us and picked out an excellent wine to go with the duck.

"As you must know James, duck is the test of a good chef, and the chef here is very, very good. Now let's dance."

Vickie let me lead but had a provocative way of pressing a leg into my crotch as we turned to the music.

"Umm, I like what I feel," she whispered. "Tell me, James, is it my outfit, my smoking, or the little activity I have planned at home after dinner?"

"It's all three Madame, I'm absolutely overwhelmed by you."

"Would you like to fuck me, James?"

"Oh god, Madame, that would be heaven!"

"I'm not surprised. Men think that nothing pleases a woman more than to be fucked. But I'm different, as I'm sure you know by now, James. The greatest pleasure for me is to keep a man in an extended and exquisite state of sexual tension while I tease, torment, and torture him—my magical three Ts. I never knew how thrilling and how totally over the top sadism could be until my dear departed Jay first asked me to whip him with my crop. That was an epiphany for me and after that I found that ordinary sex was like drinking coca-cola when a rare vintage was available or having jello for dessert instead of cherries jubilee."

She continued,

"I could tell almost immediately, James, that you were the kind of man who considers himself strong, stoic, and worldly, but who had a suppressed desire to be under the control of a strong woman. I want nothing more, James, than to condition you not only welcome the pain and humiliation I inflict on you but to make you realize that total obedience to my whims is also your greatest pleasure, far beyond any pleasure that mere screwing could have. N'est pas?"

Vickie was right. She had opened the safe where my darkest desires lay. She taught (and would teach) me that denied sexual desire when prolonged and skillfully mixed with intense pain and humiliation led to an indescribable pleasure that transcended all previous notions I had about a relationship with a woman. She teased out my incest fantasies, fanned those latent flames, and then joyfully punished me for them. Vickie was simply unworldly, a bewitching, enthralling goddess to whom I gave myself completely

On the way home in the car Vickie tormented me unmercifully, stroking my cock and blowing smoke in my ear.

"I can hardly wait to slowly run a burning cigarette over your chest," Vickie cooed. "I'm going to adore you with a lovely script "V" above your right nipple and a script "W" above the other. I can tell that appeals to you, James, because you're getting so hard. I'm going to keep it that way all night."

Vickie was true to her word except that her branding took several sessions—sessions in which in which the mingling of her smoke and perfume and the sound of her sensuous voice served to partially anesthetize the delicious pain of her cigarette against my flesh. She was in total control of my mind and my body and my ecstasy was total.

About a week after Vickie had finished her calligraphy on my chest, she announced, "I've invited Tina over this evening for a little fun and games. You're going to love what we're going to do to you, James."