The Headmistress: Chapter Five
written by:
Joshua

I'd been tasked - or instructed, depending on how you looked at it - to escort my star pupil to London to receive several distinguished academic awards. Peyton Lake, twenty years old, was not only the best student at Brighton Academy where I am the headmistress, but he is also our best athlete. Several times before our journey, I'd overheard Peyton boasting about his physical prowess with the girls of Brighton, exclaiming to his friends that all he had to do was to "snap his fingers," and the women would come running to him.

Well, as it turned out, Peyton was not as experienced as he led his friends to believe. It was during the night train journey to London that I discovered Peyton attempting to purchase the services of a prostitute. When I intervened, Peyton became embarrassed that I'd caught him doing something illegal. He became despondent, however, when he realized that I knew he was actually a virgin and had had absolutely no real sexual experiences in his life. Feeling sorry for Peyton, and because I cared deeply for him - as I do with all my students - I took Peyton into my sixty year old arms, and taught him how to please a woman. This young, twenty year old stud fucked me, his sixty year old Headmistress, several times before the night train arrived in London. And each time was better than the last.

But a surprise awaited Peyton and I upon our arrival at the main station the next morning. As I waited for Peyton to find a valet for our bags, I discovered his parents, Simon and Pamela Lake, had also been on the same train, completely to my surprise. As the crowd thinned, I suddenly spied the second wealthiest couple in Britain, watching me as I waited for their son to arrive with the valet. I was immediately struck by the fact that no one had informed me about them being on the train, but also even more concerned that they might discover that Peyton was no longer a virgin, and that I was the cause of that. Smiling at me as they made their way through the thinning crowd to where I was standing, Simon extended his hand and welcomed me to England's main city. The eighty-five year old billionaire's hands were always soft and gentle when they held my hand, which seemed often anytime Simon and I were in the same room together.

I should tell you here, if you haven't read any of my past chapters, that I lost my husband, Steve, to a drunk driver almost a year ago. In that time, I've emerged from a state of depression to regain control of my life again. I'd retired as a university physics professor and because of Steve's ability to invest wisely I had no need for money. But I wanted to return to work and so hired a thirty year old headhunter named Henry who found this position for me. What the young man also brought was a desire, unbeknownst to me until after Steve's death, for younger men. I won't go into details, but let me just say that I fucked young Henry that morning, my naked back pressed against the kitchen counter, my high-heeled feet above my head, and Henry's thick, throbbing cock slamming away at me. After that incident, I've had encounters with my twenty-five year old assistant Nicholas, and the wealthiest man in Britain, twenty-nine year old Brandon Corkson. Read my past chapters and you'll read about the sexual discoveries I've made since I realize how sexually stimulating it is to fuck younger men.

And if you have read my past chapters, you know that from time to time, my husband Steve returns to me by speaking to me from the grave. Some might call my belief that I hear my husband a sort of lunacy, but I know it's him. Throughout our married life, and even after, it seems, Steve always counseled me, always gave me excellent advice. I trusted in him completely, and still do, despite his not being physically present.

But now, here I was in the crowded train station, watching in somewhat mild horror as Simon Lake and his beautiful wife Pamela approached me. "Jan, what a pleasure it is to see you this morning," Simon said as my small hand fell into the powerful grip of his right hand. He pulled me to him, and wrapped his arms around my shoulders before placing his lips on my left cheek and kissing me lightly. I also couldn't mistake the pressure of his other hand yet again on my ass. It seems that every time Simon and I met, he makes a point of pressing either or both of my ass cheeks. "I hope you and Peyton had an eventful evening," he said, a small smile on his face as his eyes looked deeply into mine. Alarms sounded in my head: did he know how his youngest son and I had spent the hours on the speeding train, fucking in every known position, coming and having orgasms that produced screams so loud that they threatened to drown out the train whistle? I was unable to discern if Simon knew, but before I could detect any signs that he was privy to the fact that I'd taken away his son's virginity, his wife Pamela arrived by my side. She too wrapped her long arms around me and squeezed me to her body, the scent of her expensive cologne wafting to my nostrils. Like her husband, Pamela too planted a light kiss on my cheek as she tightened the embrace she had me wrapped in. Like her husband, her right hand also brushed across my ass, although Pamela was more deft at hiding the movement than Simon.

"Oh, dear lord, Jan!" Pamela exclaimed. "How wonderful it is to see you this morning. Especially after the night you must have had." Pamela's eyes locked onto mine as her husband's had, and again whistles and alarms sounded in my head at her statement. Oh no, I said to myself: they know I fucked their son and they've come to fire me, right here in the station. But before such words came from either Pamela's or Simon's lips, Peyton arrived, as surprised to see his parents as I was. Simon and Pamela embraced Peyton, and informed him that they'd see him at the hotel. Smiling broadly and kissing me once again on the cheek, - and groping my ass as well - both Simon and Pamela departed our little scene, leaving me yet again alone with Peyton.

"Well, that was interesting," Peyton said as the valet loaded our baggage onto a small wooden cart. When I inquired about the hotel Pamela had mentioned, Peyton smiled broadly and informed me that along with other prime pieces of real estate, his father owned the same hotel where we had reservations. Once again, sirens and alarms fired in my head as I contemplated being so close to Peyton with his parents a floor away. My heart began to beat rapidly and forcefully, I began to perspire, and a dread of nervousness spread over me as I envisioned being interrogated by Simon and Pamela about their son's newly acquired lack of virginity.

But it was then, as it had been all my life, that Steve returned to me. As I walked behind Peyton to the waiting taxi, my husband's voice came to me, reassuring me that everything would turn out well. "You've been here before, Jan," he said. But what do you mean, I asked the voice, uncertain how to interpret my deceased husband's words. "Rest easy, my love," Steve said again, the words burrowing into my soul. "You'll see: You've been here before." Echoes of my lovely husband rebounded through my head as I ached to hold my husband just one more time, to tell him I loved him, to lay with him. When I called out his name, silently but loudly in my head, he answered with one simple statement. "Don't forget, Jan: everything is not what it may seem, and everything different is not bad." Again, the sudden departure of my husband's voice. I wasn't angry at Steve: how could I be after all he meant to me? I only wished he would give me more information. But then, he had been a professor like me, and it was his job to draw the learning from the student rather than simply provide the student with an answer. I trusted my husband implicitly, even if he was not physically with me. I knew that in the end, everything would work itself out. But it was getting to the end that always troubled me. Steve's voice immediately went silent after his last words, and I was left to ponder the meaning and the immediate future as Peyton and I rode the taxi to the best hotel in London.

Well, that's not exactly an accurate statement, either. To say that the Hotel Lake was the best in London was an understatement. It was the most plush, best-staffed, and most expensive hotel offering travelers a place to spend the night in all of Great Britain. I'd never experienced a place such as the Hotel Lake. Immediately upon our arrival, the doorman recognized Peyton, giving the young man a deep bow of respect. As we made our way through the expansive lobby, every staff member greeted us warmly, and made signing in - which I quickly discovered we really had no need to do - easy and uneventful. Ten minutes after arriving at the hotel, I found myself sitting in a three room suite overlooking the Thames River. After the night before, Peyton and I each agreed that a few hours asleep - alone - was just what we needed. He retired to his room and I retired to mine, although a common door separated our suites.

Feeling the need for a warm, soothing bath, I quickly stripped out of my clothes, relaxed in the tub for an hour, and reentered the main living room, my still moist body covered only by a thick terry cloth robe. My hair hung in damp strands, and I felt completely relaxed. A glance at the clock on the mantle informed me I still had eight hours before the scheduled dinner meeting with Simon, Peyton, and Pamela to discuss Peyton's award ceremony. Relishing the fact that I need not rush anywhere, I stood before the clear, wide-opened windows as a cool, inviting breeze wafted through the opening. The view below and beyond was both breathtaking and spectacular.

But despite the wonderful view, I was exhausted from the previous night's sexual activities. Peyton and I took advantage of every second together on the moving train, fucking well into the early morning. In fact, we were so engrossed in each other's body that as the train slid slowly into the terminal, my hand was buried deep inside Peyton's trousers, stroking his massive, ten-inch cock. I especially enjoyed when his body stiffened and he exploded a load of hot, pearl-colored crème inside his trousers. "You better clean up quickly, baby," I said, grinning widely at him, pleased that I could make a twenty year old man exploded into sexual pleasure with just my hand.

Deciding to rest a bit since I had so much time before my evening meeting with Simon, Pamela, and Peyton, I moved to the wide, comfortable sofa where I scanned a magazine that described many of London's best sights to see. I'd only flipped through the magazine a few brief moments when the phone rang. I knew instantly who was on the other end, and answered the call in my sexiest voice, full of lust for the twenty year old Peyton once again. "Hello," I said, my voice thick with desire, the vocal cords emitting a sound that was deeper than when I normally spoke.

"Hello, Jan, it's Simon," I heard the voice on the other end of the connection say. Now what, I asked myself, sitting up straight, the white terry cloth robe opening slightly to expose the edges of the two 38dd tits that occupied my chest. I can't believe Simon's calling, I said, wishing I'd taken the receiver off the hook when I entered the room. But it was too late to hang up. The billionaire wasted no time in getting to the point, a characteristic I'd learned most wealthy men and women possess, something I'd learned from Brandon Corkson, and would soon learn about Simon Lake as well.

"Jan, I'm afraid I've just heard some distressing news," he said, my heart immediately racing and pounding in my chest. While I remained silent, Simon continued on. "I spoke with Peyton this morning about the train journey to London," Simon said, his voice even and displaying no trace of whatever emotion he was feeling. But I was suddenly on alert, because there was only one topic that concerned me about Peyton's journey through the misty, foggy English night, and that fact was that I had been the main attraction for his massive cock. When I asked Simon what it was he was referring to, hoping he might provide me with some measure of information, the eighty-five year old billionaire responded, "I know exactly what happened, Jan, and I believe it is something we need to discuss." A brief but silent pause, and Simon said, simply, "And I insist that we discuss this in person."

By now, not only was my heart racing, but so too was the flood of thoughts and worries streaming into my brain. Oh, dear god, I said to myself: He knows I fucked Peyton. I'm surely to be fired now, I said, and be banished from England in disgrace. "I say, Jan, are you there?" Simon asked when I offered no response to his statement. When I told him that I was, indeed, still on the line, Simon stated, "Well, then, how do you propose we prevent this from happening in the future? And how do you explain your actions throughout the journey?" Simon's voice was slowly but clearly becoming angrier, his tone becoming increasingly shorter with me. "Someone has to atone for these transgressions, Jan. Do you understand me?" Simon said. "You were, after all, his chaperone, but I believe you failed in your duties, to say the least."

Atone? How was I to make up for fucking Simon and Pamela's twenty year old son? It was certainly after the fact now, and Peyton was surely of age to engage in consensual sex. But I understood Simon's point: A sixty year old woman with a sex drive she seemed unable to curb had fucked the youngest son of one of Britain's wealthiest men. Someone, meaning me most likely, had to pay in some form or another. There was no taking back what I'd done to Peyton, no apologizing for enticing him to slam his thick, hard cock into my pussy. I knew the least that could happen was that I'd be reprimanded somehow, hopefully discretely by Simon and Pamela. I also knew that I would most likely lose my job unless I could convince Simon to act otherwise. I had a sense, however, that my firing was inevitable. And that Simon Lake had no intention of firing me over the phone. That's why he wants to meet, I said to myself. To fire you.

"Do you see the dilemma I am in here, Jan," Simon asked, obviously relishing the fact that he had me exactly where he had wanted me since my arrival at Brighton. I knew my best defense was to remain silent, to let Simon speak and see where the conversation went. "If his mother discovered what you and Peyton did last night, she would be very, very distraught," Simon said into the phone, his voice becoming deeper with anger as he spoke. Simon paused, perhaps for dramatic effect, or perhaps because even he could not find the words to describe the consequences of Pamela Lake confronting me about taking her son's virginity.

"Simon, how do you propose we reconcile this?" I asked, hopeful there was a way I'd be able to remain at Brighton as the headmistress. "But to be honest, Simon," I said, stalling for time, "What happened was as natural an act as breathing. And if you recall, Peyton is twenty years old and he doesn't need anyone's permission for what he did." Even I thought my comments were lame and weak, and the best I could do was to hope Simon accepted my rationale explaining how a sixty year old woman and a twenty year old man could spend hour after hour slamming away at each other's sexual parts.

Simon Lake, as with Brandon Corkson, had not grown wealthy by listening to and accepting excuses. He sighed heavily into the phone, and asked me what I thought was a very strange, very odd question. "Jan, are you dressed for the day yet? I know you're probably exhausted from the very special night you had with my son, but I want you to get dressed and to call me back within the half hour." The phone went dead in my hand and I realized then that I had no recourse but to do as Simon demanded. I was certain that when I called him back, he would summon me to his office and ask for my resignation as the Headmistress of Brighton Academy. But doing as Simon instructed me to, I rose from the bed and carefully selected the items I planned to wear to Simon's office. I'd packed several pantsuits, but I decided that if I was to be fired, I would go out in style. Black seamed stockings - which you know by now are my favorite - slid easily and sensuously up each of my slender, well-toned legs. Black panties, also silk and very expensive, covered my sixty year old ass and thick-maned pussy. A silk, black bra - the most expensive bra I owned, in fact - covered my tits. Standing and walking to the closet, I chose a black skirt, as usual, a grey-colored blouse, and a matching black blazer. Finally, I slipped my feet into a pair of four inch stiletto heels - another favorite accessory of mine - and stood before the mirror. I looked professional, yet stylish. My heart was beating as I stood before the bathroom mirror and applied light eye liner, rouge to the cheeks, and a thick layer of red lipstick to my mouth. Finally satisfied with my appearance, I slipped the tube of lipstick into my purse and redialed Simon's personal number. He answered on the first ring.

"Yes, well, right, Jan," he said into the phone, the anger still evident in his voice. "You will hire a taxi to my office and wait for me in the private outer office," he demanded. He provided me with the security code to enter the secluded outer office where I assumed his secretary sat to screen his visitors. "When you arrive, please depress the small black button you will see by my office door. You will see a phone on the desk by the door. I will call you on that phone when I am ready for you to enter. Do you understand what I am telling you, Jan" Simon asked. When I said that I understood completely, Simon ended the call by simply hanging up. Five minutes later, I was outside the hotel waiting for a taxi. Twenty minutes after that, I was standing inside the small room Simon had referred to as his "outer office." In reality, it was actually a small room with two comfortable chairs, a long sofa, and two end tables. There were no windows. As I'd been instructed to do, I depressed the small button situated along the door frame, and waited. When the door did not open, supposing Simon was on the phone or temporarily away from his office, I sat in a large chair with a small table located beside it, and the telephone Simon had said he would call me on. Now, it was simply a matter of waiting. While I waited, I cast my eyes upon my legs, clad once again in the black, seamed silk stockings. Seeing my shapely legs as they were, I couldn't help but recall the many, many times Steve and I had fucked while I wore the same style of hosiery. Although I was certain I was on the verge of losing my job, for some reason my thoughts turned to those times when I would ride Steve's cock, and he would massage the silk-covered thighs because the sensation of silk on his hands increased the stimulation he felt as his cock disappeared into my pussy. And despite those memories of my husband and our wonderful sex lives, I asked myself how long I would have to wait to see Simon and lose my job. Somehow, I felt relaxed, knowing that because my career in England was over, I might as well ride with whatever happened and simply see what the future held.

I didn't have to wait long after all. Less than one minute after I depressed the security button and sat down, the phone located on a table beside me rang. With shaking hands, I braced myself and lifted the receiver from its cradle. Simon's voice came on immediately.

"Yes, I am glad you are here, Jan. Very glad indeed," Simon said into the phone. "Now, I am going to ask you a series of questions, and considering the position you are in, I advise you to be as honest as possible, and to do exactly as I say," he said. After a brief silence, Simon asked, "Do I make myself clear, Jan?" Knowing I had no choice, and realizing that my time in England was decreasing by the moment as the result of me being unable - or, perhaps, unwilling - to curb my desires for younger men, I told Simon that, yes, I understood perfectly well what he was saying, and that I was prepared to answer any question he had for me. "Well, it may be more than simply answering questions, Jan," he said, cryptically. "You do understand that I may ask you to do something you have never done before?" With that, I knew immediately where Simon was going with this line of questioning. He was, without a doubt, going to do his best to lead me into his office and fuck me. Well, he can go fuck himself if he's going to fire me, I said to myself.

I was prepared to tell Simon I had no intention of playing his mind games when, suddenly, a calm settled over me and I felt perfectly at peace. I knew instantly where the calming effect came from: My husband, Steve. Just an instant before my brain sent the signal to my mouth to tell Simon to go fuck himself, Steve's voice filled my ears, soft and gentle, peaceful and warm. "Hear him out, Jan," Steve said. "Hear what he has to say." When my thoughts replied to Steve's voice, all he said in return before drifting away again was, "Remember what we always told our students, Jan: expand your limits and your mind will follow." And then, absolute silence as the only sound I heard was that of my rapidly increasing breathing.

I suppose the extended time between Simon's question and my short conversation with my dead husband caused Simon to become impatient. "Did you hear me, Jan? I won't ask again," he said. When I told Simon that, yes, I understood that following his instructions meant more than answering his questions, he laughed briefly into the phone, as if he could see through the walls and detect my feelings. But Simon had no idea I'd just talked with my husband, no idea that I was calm now, and that I would follow his instructions because I knew my husband would never give me advice that would lead to me to physical harm. And maybe I just didn't care anymore that I was on the verge of being unemployed.

"Yes, Simon, I heard you," I said, lifting my head briefly to stare at the ceiling. Perhaps I was searching for Steve, hovering over me like a protective angel. Or, perhaps I was sending Steve a message that, as always, I trusted him without doubt or hesitation. Or maybe I was just resigning myself to the fact that if I was about to be fired, what did I have to lose by following Simon Lake's instructions, whatever they may be? Quite possibly, as I thought about what happened afterward, I was doing all three.

"Good, Jan, good," Simon praised me. "Let's begin, shall we?" When I murmured that I was ready, I heard the sound of Simon shifting his body. "Alright, Jan, the first thing I want you to do is to tell me how you are dressed." Okay, I thought to myself, a simple enough request. I described the outer garments I was wearing, describing the black blazer, the black skirt, grey blouse, and the high heels. "Did you wear stockings, Jan?" he asked. Not surprised by the immediate and obvious direction the conversation was going, I replied that yes, I was wearing stockings. But Simon wanted more. "Are they pantyhose, Jan, or are they stockings? Tell me," he demanded. Okay, so Simon's a stocking man, I said to myself: many men are, so no surprise here, yet. I informed Simon that I had elected to wear black, seamed stockings. Still he pressed for more detail. "And the heels, Jan: describe them to me."

By now, it was transparently obvious where Simon was headed with his loaded questions. I was certain he was located just behind the thick door to his office, seated at what I assumed was a massive desk, his shriveled and tiny eighty-five year old cock grasped tightly in his hand as he jerked himself off. Perhaps I should have been incensed with his questions, but because I still felt so much at ease by Steve's unseen presence, I decided two could play Simon's silly little word game and that I could match him tit for tat. And so, I replied to Simon's question by saying, "Well, Simon, I'm wearing black, patent leather high heels with stiletto stems." Simon suddenly inhaled deeply, followed immediately by another sharp intake of breath. Happy to play along now, happy to take the momentary lead in this little game of words, I added, "and they are indeed quite sexy on my feet, Simon." I smiled inwardly, guessing that as long as I played along with Simon's game, I had a good chance of keeping my job. Maybe this is what Steve meant when he told me to expand my limits. It was then that I heard another sharp intake of Simon's breath, and possibly a small moan as I lifted my right foot from the floor and twirled the limb over the carpet for a few seconds.

But any belief that I could match Simon and play his game better than he was short lived. Just as quickly, Simon asked into the phone, "Are you wearing lipstick, Jan?" When I replied that, yes, I was wearing lipstick, Simon countered his first question with another. "Very good, then. And do you have the tube of lipstick in your purse?" Again, I replied that I had brought the tube of red paste with me. And again, this time there being no mistaking it, I heard an audible moan when I informed Simon that I had the gold-coated tube of lipstick in my posession. "Here's what you will do, then," Simon said, his voice lusty and thick. "Remove the tube from your purse and lay it beside you on the table. Let me know when you have completed that task." Okay, I thought to myself: a simple enough request. Or, was it a demand? I let Simon know when the four inch, gold-plated tube lay beside me on the small table.

"Very good, yes, very good, indeed," Simon almost moaned into the phone. By now, I had a vision of Simon sitting in his high-backed chair, his trousers open, and his eighty-five year old hand flailing away at his old, wrinkled cock. That is, if he can still get his meat hard, I said to myself. It was clear now that Simon planned to jack his cock, planned to come while talking to me on the phone, but I had no idea why he was so interested in the tube of lipstick. It also appeared that Simon intended to remain in his office while I remained in the deserted outer office with only the thick oaken door preventing us from seeing each other. Well, that is perfectly acceptable to me, I said to myself: I wasn't sure I could stomach the sight of an eighty-five year old man's wrinkled and shriveled cock, anyway. But I could play this word game with Simon, and as long as he remained on his side of the door and I remained on mine, I didn't see any harm in doing as he asked.

It was time for Simon's next request, or demand, depending on whose viewpoint you took. "Alright, Jan, now tell me this: are you wearing panties? Are you wearing a bra?" There it was: the two questions that had to be asked to kick this little game into another gear, to increase the speed of getting to the end, wherever and whatever that was. I knew I had two options: I could stop the game right now and walk out. But I knew that doing so would cost me the job I'd come to love. Or, as I had so far, I could play along with Simon, tell him what he wanted to hear, and possibly keep my job.

Deciding it was better to cooperate than to fight Simon, I smiled as I cooed into the phone, "Yes, Simon, I'm wearing panties and a bra," I said. "And, they're both black and made of the finest silk." I knew that additional bit of information might actually do me some good: If Simon knew I was wearing black lingerie under my clothing, he might actually erupt into his hand and this little game would come to a quick end. Just to add spice to the stew, and to possibly cause Simon to reach a self-induced orgasm, I added, "and they both fit very snugly, I might add." In response to my statement, I heard a slow, deep intake of breath through the phone, followed by the sound of rapid and deep breathing. I sensed Simon was closer now to coming, closer to spewing a load of hot crème into his hand. I decided to work harder to make him come, to dive in deeper than I had before. After all, if I played my part better than Simon expected, not only might I keep my job, I might even be able to negotiate a raise as well.

"Oh, I like that fact, Jan," Simon said, "I like that very much, indeed." When I asked Simon what else he wanted to know, he surprised me not by asking if my nipples were hard or if my cunt was wet - which they both were - but rather, by issuing me another demand. "Now, Jan, here's what you'll do next. I want you to stand, lift your skirt, and remove your panties." Silence followed his words, and stunned me. I hadn't anticipated the game going so far that I would have to remove any parts of my clothing. And I certainly had not arrived expecting to slide my panties down my stocking-covered legs, and taking them off my body. "Did you hear me, Jan," Simon asked, pressing now, impatient, wanting to know that although he could not see me, he was still in charge. When I responded that I had, indeed heard him, he asked, "Then what the fuck is taking so long, then? Why are you simply standing there, doing nothing?" It was those words that I failed to realize were posed as a question rather than a statement that would later cause me additional heartache. But more on that later.

Okay, Jan, what are we to do now, I asked myself. I was torn between walking out, returning to Brighton, packing my bags and taking the first jet back to the United States, or complying with Simon's demand and removing my panties, which I was now certain keeping my job hinged on. I looked at the heavy oaken door, and made an instant decision. If Simon couldn't see me, he couldn't touch me. And as long as he remained in his office, I was safe. I laid the phone on the small table, stood, and lifted the hem of my skirt. With the garment now lifted high, I inserted my fingers into the panty's waistband, and slowly slid the black silk apparel downward over my shapely ass, down my well-toned legs, and over each high heel until I was able to step out of them. I bent at the waist and retrieved the panties from the floor, once again taking my seat beside the small table. If I'd paid greater attention to the panties, I'd have noticed that the crotch was rather soaked, particularly in that area where they made contact with my pussy. I laid the panties in a wad beside the golden tube of lipstick and retrieved the phone from the small table. "Okay, Simon, you got your wish," I said, my heart beating faster in the realization that I was now sitting in Simon Lake's outer office with my cunt-juice soaked panties lying on the table beside me. "The panties are off and lying on the table beside me," I said into the phone. "I'm waiting."

At first, I thought Simon had gone to sleep because the silence that I heard from the phone seemed to last a long time. But finally, I heard Simon breathe, and knew he was still there in his office. "Well, done, Jan," he said, "Well done, indeed." I heard more rustling of clothing through the phone, deciding that by now, Simon must be completely unclothed. "Now, if you will, Jan, please grasp the tube of lipstick, and stand again, please." What was Simon going to have me do, I asked myself: Reapply my makeup while I sat in his office, pantyless? Hoping this strange ordeal was near its end, I did as Simon instructed and stood, my weight supported by the four inch stilettos I'd described to Simon only moments before. The lipstick tube rested in my right hand, the metal cool to the touch. I had some measure of difficulty maintaining the phone on my shoulder, also making it difficult to hear any of Simon's following commands. But as I said, he was extraordinarily wealthy because he'd developed the ability to anticipate actions before anyone else. So, I was not surprised, really, when Simon instructed me to depress the speaker button on the phone, "So that you can use both hands for what's to come." I laid the phone on the table, depressed the small, round-shaped, white-colored button, and the room was immediately filled with the sound of Simon's heavy breathing. "Right, now that that's taken care of, we can proceed," he said, his words echoing from every corner of the room.

I suppose I should have anticipated what it was Simon was on the verge of ordering me to do, but so many thoughts and emotions cruised through my brain at that instant that I was a jumble of nerves and a desire to end this ordeal as quickly as possible. But I was also angry: angry at myself for fucking Peyton and getting myself into this predicament, and angry at Simon that he would use my job as leverage to make me do possibly humiliating acts. But regardless of who I was angry at, the bottom line was that I desperately wanted to keep my job and the man who could ensure that happened was sitting on the other side of a heavy, oaken door with his eighty-five year old cock wrapped tightly in his hand. Simon's next spoken words woke me from the temporary self-bashing I'd engaged myself in.

"Next, Jan, I want you lift your skirt, spread your legs, and slide the tube of lipstick into your pussy," he said, his words not presented as a request, but, rather, as a demand. "Let me know when you have completed that task, dear," he said sweetly, as if he'd just asked me if I desired a cup of tea. "I'll wait," Simon said with finality.

So there it was: Simon's plan for me and the way for me to keep my job. I admit, his request was strange, and I never anticipated that I'd be standing inside a London office building with my skirt lifted above my waist and my fingers sliding a tube of lipstick into my cunt. All this has to be a dream, I said to myself. But the fact of the matter was that everything happening to me at that time was very real, and the more important fact was that Simon was truly in control, and he had no intention of letting me off the hook for fucking his young, twenty year old son. But I hesitated and stalled as I attempted to think of an alternative to planting a tube of lipstick into my pussy. Where are you Steve, when I need you, I asked the room, silently. I need you now, my love, I need you.

So often since his death, Steve has never come when I summoned him. No, instead, he's waited until after the fact to speak to me, to tell me what I learned, and how he had guided me to expanding my knowledge in so many areas. I didn't expect him to answer my question, but because, perhaps, this was a special situation, he chose to answer my plea. "I'm here, Jan," he said, his voice as patient and caring as ever. "You're on a journey, love, and you must expand your limits, as I told you, in order to arrive at a new place." Looking about the room, my skirt raised, my cunt exposed, a tube of lipstick in my hand, I searched every corner for some sign of Steve. But other than his voice, there was no sign of the man I continued to love with all my heart. There was still his voice, though, still with me, comforting me, soothing me, assuring me that no matter what happened, I would be alright in the end. "Expand your limits, Jan, expand your limits." And then, he was gone again. And I was alone in the room, still.

And Simon was still waiting. "Jan, I don't wish to take all day," he said. "Have you done as instructed? Have you placed the lipstick tube in its special place?" Between Steve's comforting words and Simon's demands, I knew there was no other option but to do as Simon asked. Holding the six inch, gold plated tube by its end, I squatted slightly, my knees bent outward, the thin stiletto heels supporting all six feet of my height, placed the tube against my cunt lips and pushed, slowly, slowly, the cool metal stimulating the nerve endings in the pussy lips. To my surprise, I felt pleasure from the invading lipstick tube, felt as if a small cock had been inserted into my cunt. Oh, my, that's a surprise, I said to myself: this must be what Steve was referring to when he advised me to expand my limits. I could feel the tube inside the cavern of my pussy, sitting in the center of the place where Steve's, Henry's, Nicholas's, and now Peyton's cocks had each deposited their loads into me. It wasn't uncomfortable at all, but there was an unfamiliar pressure that seemed to stimulate the nerve endings located along the inner pussy walls. I took one, then two, then three steps and discovered that with each step, that because the tube was so long, each step I took caused the tips to bang against the pussy walls, causing the nerve endings to fire repeatedly and forcefully. It was as if I had a small cock buried inside my pussy that was there simply to cause me pleasure. As I removed the fingertips from my cunt, I marveled at how wet I'd become, despite the circumstances. Jeez, I said to myself: I can get wet anywhere!

When the tube was fully inserted into my now very wet cunt, I stood tall again, bent at the waist and informed Simon through the speaker that I had done as he had instructed. Believing the ordeal was near its end, I began to sit when I was interrupted by Simon again. "That's a very good girl, Jan," he said. "Please stand again," he said, as if he could see through the walls. "Now, your next instruction is to enter my office, come to my desk, and deliver the lipstick to me. Do you understand, Jan?" What was there not to understand, I said to myself? The old bastard wanted me to saunter into his office, remove the tube of lipstick from my cunt and lay it on his desk. That meant he'd have a clear view of my cunt and the thick mat of hair protecting it from view. But what else are you going to do, Jan, I asked myself. You refuse to do this, and you'll be sent home in disgrace. Resigning myself to my fate, I was able to take only four steps toward the door when I felt as if my cunt were on the verge of exploding. Oh, hell, I said to myself as sexual tremors spread from my cunt and traveled at an amazingly fast speed up and down my legs and across my upper torso. I had to lean against the frame of Simon's office door to steady myself, so close to coming to an orgasm, I was. I had to admit that this practice of jamming objects into my cunt was new, but it wasn't that unpleasureable, either. Having momentarily lost focus on where I was and what was being demanded of me, I placed my head against the oaken doorframe and did my best to stifle the orgasm that seemed to be on the very edge of overtaking me. But because I was not the only person involved in this office, many other demands awaited me before the afternoon would come to an end.

From across the room, I heard Simon's voice escape the speaker phone. "Open the door, Jan," Simon instructed me. "I'm tiring of waiting." Pushing on the thick door, I was presented with a view of a room large enough to be classified as a conference room, rather than a businessman's office. Simon's desk sat at the end of what appeared to be a great distance across the room, the piece of furniture long and wide, and, obviously, very expensive. Simon sat behind the desk in a high-backed, leather chair, watching me. The curtains were opened and clear, brilliant sunshine streamed into the room. To my surprise, Simon was still clothed: When I arrived at his desk, after walking the distance silently on the four inch stiletto heels across the lush carpet, I was even more surprised to find that Simon's trousers were still buttoned and belted as well. Not once after I entered the room did Simon's eyes leave mine.

But it was also the walk across the room that almost took my breath away. Yes, I have sex toys at home and Steve would often use them on me, slipping the long dildo inside me, teasing my cunt lips and clit with a vibrator. But not once in my life have I experienced a simple walk across carpet in high heels as I did on this morning. Each step in the stiletto heels sent shivers up my legs, and those shivers created small convulsions in my cunt, each cunt convulsion caused the tube of lipstick, still buried deep inside the dark spaces of my pussy, to ricochet from one side of my pussy cavern to the other. I was so close to coming by the time I arrived at Simon's desk that I was prepared to lay on my back on his wide, long desk, finger my clit, and experience what I knew would be a monumental orgasm.

But none of that is what Simon had in mind: not at that moment, at least. I arrived at his side, looking down at him, waiting expectantly for my next assignment. I was torn between two thoughts: I was ready to tell this rich bastard to go fuck himself, that I didn't need any job as badly as he believed I wanted to remain as the Headmistress of Brighton Academy. But I was also experiencing a situation completely unlike any I'd ever been in my entire life. Never in my life had I inserted anything foreign -except for dildos and vibrators - into my cunt then paraded across a room in high heeled shoes. Never in my life had I been told to do that, even by my husband, Steve. The sensations erupting in my cunt area caused me to momentarily recall that I was still in a precarious situation, one where I might possible be unemployed by the end of the day. Finally, as I looked down at this eighty-five year old bastard, it was then that I returned to reality, doing my best to calm the erotic firestorm raging in my cunt.

But it was then, just as I arrived at Simon's side, that I fully understood my deceased husband's words about expanding limits, about going beyond what for many years had been the norm. I suddenly understood why, despite my initial objection to jam the lipstick into my cunt, why I had not rejected Simon's orders to fill my cunt with a foreign object. I understood too what Steve meant now, and I knew that I really hadn't exceeded my former limits: in fact, I was so cognizant of my sense of being that I knew I had taken no more than a few steps toward reaching what had been the leading edge of my former limits and was about to enter new territories and new experiences. I was on the verge of entering new territory, and although I am sixty years old, I found myself excited at what lay ahead.

But Simon had no idea what I was thinking at that moment. He was impatient, and it was the sound of him clearing his throat that brought me back to reality. "Lift your skirt, Jan," he said, his eyes burning holes into me. There was now no need for defiance, no need to argue, no reason to debate anything with Simon. I mean, I had a tube of lipstick buried in my pussy because he'd told me to do so, and I really hadn't fought him at all on doing so. Therefore, I grasped the hem of the skirt, and lifted slowly, knowing that below me, as the hem lifted, Simon would be treated to a view of my well-toned thighs, then the lace stocking tops, followed by a brief expanse of naked skin above the tops, and ending with a clear view of my pussy, the same view his youngest son had been privileged to no more than twelve hours before. As more and more of my body came into view, Simon's eyes widened. It was then that I lowered my own chin and noted with no surprise, the extra-large bulge jutting from Simon's trousers.

After examining my exposed cunt for several seconds, Simon lifted his chin and said to me, "Alright, Jan, give it to me." I knew he wanted the tube of lipstick, and I knew he wanted me to give it to him. That was, after all, the main reason for me jamming it into my cunt and entering his expansive office, wasn't it? What I didn't know was that Simon had other plans for retrieving the small tube from my cunt. It became evident to me that he planned to take part in the retraction process, but what wasn't clear to me was that he planned for me to remove the tube in a special manner.

With the hem of my skirt in my left hand, I extended my right arm downward and placed two fingers into the thick covering of cunt hair. I quickly found the pussy lips and slid the index and middle finger upward and inward, the two digits sliding in easily because of the excessive amount of moisture literally oozing from my cunt at that time. I found the tip of the lipstick tube, not surprised that it was slimy from being soaked in pussy juices and began to slowly maneuver the tube so that I could pull it from my cunt with the two fingertips. Just as the tip of the tube emerged from my pussy, Simon lifted his hands and removed my hand from my cunt. Looking down at Simon, I said, "What are you doing? I thought you wanted the tube of lipstick."

Simon was quick to respond. "I want you to squeeze it from your pussy, Jan," he said, his voice now laced with pure lust and desire. He extended his right hand and ran his fingertips through the covering of cunt hair. Now, while I admit that it seemed odd to be fondled by my superior, I have to also profess that Simon's hands caused the nerves in my pussy to fire wildly. As his hand slid from the front to the rear of my cunt, his fingers quickly became coated with juices from my pussy. I did everything imaginable not to moan out in sexual pleasure. But, my friends, I failed at that mission and as Simon stroked my cunt with his open palm, I began to thrust my ass back and forth, riding his hand, and knowing that I would soon explode in a sexual eruption if something didn't happen soon.

"Oh, god, Simon," I moaned, surprised I'd given Simon the verbal sign that what he was doing to me was exciting and stimulating. But I couldn't help myself, and the more Simon palm-fucked me, the wetter my pussy became, and the more I wanted something other than a six-inch, slim tube of lipstick inside my cunt. It was when Simon removed his hand from my cunt that I was brought back to reality again, and realized that I was still standing with my legs spread wide, my skirt held high above my waist, and a tube of red lipstick still buried inside my burning cunt. Simon realized that as well. He lowered the height of his hand by several inches, the palm still up and facing my hairy cunt, and said, "Now, Jan: you've stalled enough. Drop the tube into my hand, please."

Looking down at Simon's expectant expression, I knew he was right. I mean, think of everything I'd done just since entering his outer office less than an hour earlier: I'd stripped off my panties, I'd inserted a tube of lipstick into my cunt, and now, here I was standing before an eighty-five year old man with my skirt raised and my hairy pussy clearly in view. And to top all that off, I was seconds away from squatting over his hand and ejecting that same tube of lipstick from my cunt and into the palm of his hand. Well, fuck, Jan, I said to myself: You've come this far and if you want to keep your job, what else can you do?

I stepped forward so that my body was closer to Simon. He lowered his hand but kept it positioned between my legs. Everynow and then I felt his hand rise and touch my dripping wet cunt lips, but I knew that his intent wasn't to stimulate me: no, his intent was to feel the small, six-inch tube of lipstick fall into his palm. Well, let's give the old bastard what he wants, then, I finally stated. Looking down, I squatted a few inches closer to the floor, and using my cunt muscles, began a series of internal movements that forced the golden tube to emerge slightly from my pussy. I knew the thick hair was preventing the tube from falling, so I used two fingers to spread the thick mat to allow the tip of the tube to slide a few millimeters further out of my cunt. I looked down, but could see nothing through the thick forest of pussy hair.

Simon, however, could see perfectly what was happening, and he remained quite impatient. His body was positioned as if he were a gynecologist, sitting on a low-lying stool, examining a woman's pussy from waist level. "Push, Jan, push, love," he said, his eyes straining to see every movement of the tube. When the first inch of the tube emerged, Simon's face broke into a wide grin, and gleefully said, "Keep going, Jan, keep pushing!" Another abdominal push and half the lipstick tube now rested half in and half out of my cunt. "Almost there, love, almost there!" I heard Simon yell under me, my view of him now obscured by the height of the hem of my skirt. "Give me the goddamn lipstick, Jan!" I heard Simon demand and finally, after several hard stomach and pussy muscles contractions, felt the tube fall from my cunt, supposing it had landed in Simon's greedy palm. That fact was confirmed when I heard Simon laugh out in triumph, and as he reclined back into his high backed chair, the prize he'd waited not so patiently for in the center of his palm. I attempted to lower my skirt now that I'd pushed the tube from my pussy, but, as always, Simon had other ideas.

Slowly, Simon placed the pussy-juice covered lipstick tube on his desk, and looked up at me. "Well, that was splendid, Jan," he said. "Just splendid, indeed." I suppose he saw the look of expectation on my face, one that expressed my desire for the episode to be over. But as I would recall later, this afternoon session in Simon's office was far from over. With his eyes still locked onto mine, Simon lifted the tube from his desktop, and stood, the small tube once again in the palm of his hand. "I have plans for this tube, Jan," Simon said, his voice sounding almost sinister.

But looking into Simon's eyes as I stood just mere inches from him with my skirt still raised and my cunt exposed, I did not feel fear. No, I recalled Steve's words from the outer office, that this day would prove something different to me. So, I wasn't truly surprised when Simon placed the tube between the right index and middle finger of his right hand, lifted his hand, and slid the cunt-soaked tube between his lips, allowing half the length of the small pipe to remain visible. Nor was I surprised when he stepped toward me, wrapped his arms around my shoulders and drew me to him. I knew in an instant what he wanted me to do, so, again feeling strangely calm, I too slid my lips over the exposed end of the lipstick tube and pressed my lips against Simon's mouth. It was the first time I'd kissed this eighty-five year old man erotically, the first time I kissed him because I wanted to. As our lips met, I felt the coolness of the tube on my lips, then felt Simon's long, pointed tongue slide past the tube and into my mouth.

Now, I've sucked several cocks in my life, and I can tell you that sharing the tube of cunt-juice covered lipstick with Simon was just like sucking on a very small cock. What I can also tell you is that each time Simon used his tongue to push the tube into or out of my mouth, more nerve endings exploded in my body, causing me to want more, despite the location and the situation. It was exactly as Steve had explained: if I let my limits expand, I'd find new areas of pleasure. And standing her with Simon Lake, the wealthy billionaire, the husband of Pamela Lake and the father of Peyton Lake, having his eighty-five year old mouth pressed against mine began to send sexual shivers throughout my body. I was somewhat surprised, then, when Simon broke the kiss and moved backward to retake his seat. "Remove your clothes, Jan," he said as he stared intently at me. Without a word, I began to disrobe, piece by piece. First the blouse and blazer, followed by the skirt. Simon grinned broadly when I extended my hands behind me and unclasped the bra, letting it fall to the floor to join the ever-growing pile of clothing and lingerie at my feet. I attempted to remove the stockings, but Simon quickly demanded that those particular items remain on my legs, as were the heels. I was dressed now in nothing more than two black, seamed stockings with lace tops, and four inch, patent leather stiletto heels. My chest was heaving as I stood semi-naked before Simon, my emotions still swinging from wanting to gather my clothing and escape from the room, to curiosity and wanting desperately to know what special trick Simon had planned for me. I anticipated that Simon would extend his arms and finger my pussy and my tits, but I was wrong. For one full, silent moment, all Simon did was to stare at me. When he finally did move, I was unprepared for what happened next.

Now, you might think that I was surprised when Simon unbuckled his trousers, opened the zipper, and brought his eighty-five year old cock into view. You might think that I would attempt to prevent him from exposing his meat, despite my realization as to where all this would end. But you know, it wasn't Simon bringing his cock into the open that surprised me. And by now, it wasn't his weird demand for me to shove a tube of lipstick into my cunt that surprised me, either. No, what caused my eyes to widen was the monster that slowly emerged from Simon's trousers. Inch after inch after inch of hard, thick, veined cock slid from Simon's now fully opened trousers until he held at least thirteen - possibly more - full inches of hard cock between the fingers of his left hand. The head was at least three inches wide, purple-colored with sexual anger, the tip moistened with precum, as several drops of the erotic fluid escaped the tip and slid down the head. The shaft was massive, long, and ever so wide. I remember thinking, that's going to hurt, as I gazed wide-eyed at Simon's enormous cock. Where Peyton had jammed a ten inch cock into my pussy, his father, Simon had him beat by at least three, perhaps four inches. In all my life, I'd seen a monster cock such as Simon's only in adult movies. And now that I was standing over this human pipeline, I realized that I'd been waiting for this situation all my life. I knew that it was Steve who had led me here. Simon wiggled out of his trousers and shoes, and remained dressed in his expensive shirt and tie. The naked, lower half of his body showed that he rarely got out into the sun, but then, why should he, I recall asking myself.

But it was time for action again, and as I stood looking down at Simon's supernatural cock, I found myself amazed that a man his age could continue to obtain hardons, and that he had such a big cock to begin with. "Come here, Jan," Simon said, his hand now stroking the human tropical snake he'd kept concealed in his trousers until just one minute ago. "You know what to do with this, don't you, Jan?" Well of course, I knew what Simon wanted. He wanted me to squat over his cock as I had his hand, and suck that meaty, thick tube into the deepest regions of my sixty-year old cunt. I moved forward and attempted to straddle Simon's cock, but the old man's powerful hands stopped me. "No, Jan," he said. "That's not what I want." Looking up at me, he said, simply, "Take it into your mouth."

I had no idea how I would ever get Simon's cock into my mouth. I knew there was no possibility of taking the entire length into and down my throat. I knew I'd choke and die of asphyxiation if I tried. I found myself somewhat frightened by the prospect of even trying, despite my love for sucking Steve's cock deep into my mouth when he was alive. I guess I hesitated too long for Simon because as I stared at his massive, wide, and thick tube awaiting the arrival of my lips and tongue, I heard Steve's voice again, not urging me forward and down, but, rather, reminding me. "Limits, Jan," he said, "limits." And I knew in an instant exactly what my husband was referring to.

All my sexual life, I'd taken Steve's cock easily into my mouth. My deceased husband had a seven inch cock, but it was very wide and thick. Taking Steve's meat deeply between my lips was never a problem for me. And I loved sucking his cock because it not only made him happy, I discovered early in our sex life that I had exposed nerve endings located in the rear of my throat that were hyper-sensitive to being pressed upon. That mean that on rare occasions, the head of Steve's cock would push against those nerve endings and I'd experience a more enhanced orgasm. But only occasionally, and never with any predictability. So, in essence, Steve's cock had been my sexual limit. Not in the sense of either of us being sexually inexperienced but, rather, not having experienced another person sexually during the time of our marriage to one another. And, also that I had been limited in the size of cock I'd taken into my mouth before and since Steve's death. What my husband was clearly telling me was this: You must now exceed your personal limit, Jan, and grow from the experience.

Perhaps Simon was confused as he witnessed one perplexed expression after another cross my face as I stood clad only in stockings and high heels before him. If he was confused, he was also more impatient than he had been before as well. "Jan, I'm tiring of waiting," he said, his hand firmly wrapped around the massive cock protruding from his crotch. Slowly, I bent onto my stocking-covered knees, placed my hands around Simon's mammoth-sized dick, and eased my lips down onto the wide tip. The skin was soft, despite it being stretched to its limit by the sheer size of the prick I now held firmly in my hand. But still, I hesitated, still unsure I was doing the right thing. I mean, did I really have to resort to extortion to keep my job? Was that the type of person England had turned me into? Again sensing my hesitation, Simon grasped the back of my head and while pushing my mouth down upon his cock, said, "Remember, Jan, this is all because of what happened with Peyton." That was his signal to proceed now, to suck this human pipeline deeply into my mouth. Well, as deeply as I could get it, anyway.

Opening my mouth wider, I lowered my head until the wide, spear-like head of Simon's cock rested firmly between my lips. I began a series of tongue flicks that caused Simon to jump slightly in his seat. When I felt his hands rest upon the back of my now tussled head, I knew he wanted me to begin a series of up and down head movements that would cause his cock to slide deeper and deeper into my mouth. Knowing my job was on the line, I began to suck inch after long inch of Simon's thirteen inch cock into my mouth, raising my head slowly upward before thrusting it downward quickly to create a sensual effect that simulated alternating sucking strengths. I increased the speed of the sucks, faster and faster until my hair, despite being pressed down by Simon's hands, flew about my head. Above me, although I could not see him, I heard Simon beginning to moan as he lifted his ass to mouth fuck me, to match my sucking motions. After several moments of hard intake, I was surprised, but also impressed with myself, when I realized that by now, I was taking a full nine or ten inches of Simon's tube into my mouth with each oral intake. Simon was fully into the action now, his naked, hairy ass slapping the leather of the seat loudly each time he slammed it downward. "Take it all, baby, take it all," Simon begged as he attempted to force the entire length of his extended cock into the small space that represented my mouth.

Although by now I was on the verge of gagging openly, Simon thrust his ass upward so forcefully that I felt two inches of new cock enter my mouth. The action between his legs was now violent and hard, but neither Simon nor I had any intentions of ceasing this suck fest. ‘FUCK, FUCK FUCK!" Simon began to moan. I opened my eyes and was surprised yet again when I noticed just how close my nose came to the base of Simon's shaft with each downward cock inhalation. Spurred on now by a desire to complete the act, and pushed forward by the motivation that I would be successful at everything I set out to do, I lifted my head upward until only half of the thirteen inch monster remained pressed between my lips. I hope you enjoy this, Simon, I said to myself as I threw my head downward as hard as I possibly could and every last millimeter of Simon's thirteen inch human pipe slide between my lips, filling my mouth completely and pressing my jaw farther apart than it had ever been. At least four inches of the wide cock slid down my throat and I fought valiantly to not gag. But now that the entire length of Simon's immense tool was buried between my lips, I knew I would have to lift my head to suck as I lifted my head, and that Simon would never be satisfied with me taking the full length of his meat just once. Well, you got yourself into this when you fucked Peyton, I said to myself: I guess there's only one way out. Slamming my head downward again, I was assisted in swallowing Simon's cock wholly again by the excessive amount of saliva I'd produced because of the presence of human meat in my mouth. I realized with glee that this second attempt to swallow the entire length of Simon's tube was much easier than the first time, and so, began to lift my head upward and to slam it down so forcefully that each subsequent intake of cock became progressively easier.

I also realized that the tip of Simon's cock pressed firmly against the exposed nerve endings in my throat with each suck. By now, with my head a blur of up and down motions, each downward movement to take in Simon's cock resulted in me actually moving closer to an orgasm. Never in my life had I reached this point where sucking a cock could cause me to erupt. But it was there, the definite tingling sensations that began in my throat and traveled to my brain where the nerve combined tinglings met and worked together to cause me to come. Realizing I no longer needed to use my hand to hold Simon's cock in place, I released the shaft and immediately cupped each now jiggling titty in my palms and began to assault my sweat covered chest while pinching the nipples as hard as possible.

I'd never been to this level of sexual lust before in my life. Not once before had I ever felt the desire to twist my nipples as if my fingers were a pair of pliers. Not once had I ever felt the sensation of wrenching each fleshy tit under my chest so hard that I cried out not in pain but in exalted joy. But here I was, upon bended, stocking covered knees, bent forward at the waist, and simultaneously stuffing a monster cock into my mouth while my hands painfully assaulted my 38dd tits.

Yet again, even in the midst of Simon's moans and my muffled cries, I realized that I had two hands, and that each hand could be used to further stimulate my body and drive me ever closer to coming. I released the right tit from my hand, certain the flesh was both red and irritated, and placed the hand fully upon my now dripping wet cunt. I was temporarily stunned by how wet my pussy actually was. It was as if I'd just stepped from the ocean and the wet, salty water had somehow seeped into and filled my sixty-year old cunt. Wave after wonderful wave of pussy juice flowed from my cunt and soaked my hand, filling the palm with juices I anticipated eagerly licking off later. The tip of the index finger found the clit, swollen and stiff, excited and awaiting more, more, more. I alternated between jamming the finger full length into my cunt and teasing the clit. I continued this movement of self-stimulation for several moments, still hearing Simon moaning above me, still swallowing every inch of his amazing, amazing cock. When the first twinges of an orgasm began in my cunt, I quickly removed the left hand from the left titty and just as the waves of orgasm began to surge over me, jammed the index finger of that hand into my asshole. My body was now supported by Simon's wide, hairy thighs, along with my bent knees. In and out, one finger jammed between my cunt lips, while I buried the other finger to the knuckle up my tortured ass. I didn't care anymore about being fired: I'd just exceeded my limits, as my husband had asked me to do. My body shook so violently from the wracking, body bending orgasm that although the full length of Simon's thirteen inch cock lay buried in my mouth, I was nearly thrown to the floor by the force of the erotic tidal wave that tore through my body and tossed me from side to side, much as a tsunami wave will do to a small village. Because Simon's cock was so huge and filled every available space inside my mouth, the best I could do was to moan soft, vibration-causing sounds that resonated through and around Simon's cock and my lips.

But there were two of us engaged in this sexual dance, and there was no way Simon was about to be forgotten. I'm certain that as he lowered his head and watched me explode in orgasm, he realized that he'd momentarily lost control of the situation. Fortunately, he allowed me to finish the orgasm. When the sexual tremors subsided, I slumped forward, my heads resting beside Simon's still erect, still standing-tall cock. I was completely exhausted. Simon grasped me under the arms and lifted me upward, the tremors still cruising through my body, and positioned me over the concrete-hard cock he'd been waiting to bury inside my pussy. Looking up at me as I straddled his waist, Simon said, "You're going to enjoy this, Jan."

Now, I knew what he meant by his cryptic message. I knew he was wishing me luck on taking the full thirteen inches of cock as deeply into my pussy as I had in my mouth. Well, as you know, I'm a fighter, and I'll be damned if I was prepared to let Simon Lake defeat me with his cock. I'd swallowed it with my mouth: I could do the same with my cunt. Looking down at the eighty-five year old billionaire, who had removed his shirt while I sucked his cock, I temporarily marveled at how physically fit Simon was, and even more eerie, how closely he resembled my deceased husband. But Steve wasn't here, and while I still love him with all my heart, I also wanted Simon's cock. Not only did I want to prove that I could take every inch of it into my cunt, I wanted it because I was starved sexually, and I wanted to come again with that monster buried as deeply as possible inside me.

"Okay, motherfucker," I said to Simon as I straddled his waist. As my left leg slid over and beside Simon's naked legs, the silk stockings massaged his skin and mine, starting off another series of sexual wildfires that could only be doused with the juices of not one but two human orgasm. Squatting more now, I lowered my naked ass and hungry pussy down, down, down until the wide head pushed against my cunt lips. "Well, hello again," I said as I simultaneously leaned forward, lowered my willing pussy, and grasped Simon's naked shoulders in my pussy juice stained hands. "Here we fucking go, Simon," I said, enjoying playing the role of a whore, wanting to suck every last inch and millimeter of this thirteen inch river snake into the absolute deepest depths of my cunt.

In one quick movement, my cunt swallowed Simon's dick, my tits smashed against his face, and we began a series of upward, violent, deep-thrusting movements that both Simon and knew would end in orgasms for both of us. Each time I lifted my ass, Simon grasped my tits, and at my urging, began to maul the already reddened skin and nipples forcefully until I cried out in pain and in pleasure. Loud, consistent flesh slapping sounds mixed with our moans as I bounced my naked ass off Simon's naked upper thighs. I have to give the old man credit: for a man who was eighty-five years old, he could fuck. He hadn't lost one single atom of skill or talent and he used his cock like an expert. Faster now, even faster still, and eighty-five year old Simon Lake and sixty year old Jan Adler inched closer to exploding sexually onto each other.

Simon exploded first. I actually felt his cock widen between my cunt lips, something I would never have believed possible before this afternoon. But as spurt after spurt of hot, pearl-colored crème spewed from Simon's cock, I felt the inner chambers of my pussy beginning to fill not only with Simon's meat, but also with the thick sexual juices his body created when stimulated to a high degree. Simon wrapped his hands around my now sweat-covered ass, and pulled me mightily down onto his cock, unwilling to surrender one sensation or sexual thrill.

Just before I came, I changed my body position by lifting my black stocking covered legs so that the high heels still on my feet rested beside Simon's naked ass. This new position allowed the old man to drive into me even deeper, and as I reclined backward, I felt the hard shaft of his cock begin to stimulate my excited clit. Simon released my ass and began to massage my silk-covered legs, closing his eyes and moaning loudly each time his sweaty palms crossed over my thighs. It seemed as if his orgasm would go on forever, but it soon ended, as did mine. Finally spent and exhausted, I leaned forward with Simon's massive, more than a foot long cock buried in my pussy, kissing Simon on his face, his naked shoulders, his broad, hairy chest. For one instant, and for only one instant, I fantasized that it was Steve I'd just fucked and who'd filled my cunt with more come than three separate fucks could provide.

Simon and I rested for several moments before he eased me from his lap. With the stockings still covering my legs and the heels still on my feet, Simon led me to a small bathroom located just off his office. He undressed me, removing the stockings and heels, kissing every inch of newly exposed skin. We showered for twenty minutes, during which time I again blew his cock, and he again fucked me while I braced my back against the shower wall and he held my left leg at waist level while his monster dick pummeled my pussy. We dried each other off with the softest towels I'd ever used, then walked back to his office where we reclined on a small sofa. Quiet talk resulted in us falling asleep, Simon's hand resting on my battered tits, my right hand wrapped firmly around his amazingly still rock hard cock.

When we awoke, hours later, Simon summoned his personal assistant, a middle-aged woman named Madge, to bring us a late lunch. To my surprise, Simon strutted around the room naked despite Madge's presence once the food arrived. I couldn't help but notice Madge's eyes focusing on Simon's low-hanging meat, her eyes signaling to me that she either wanted Simon's thick, fleshy cock inside her cunt. The thought came to me that she might have already had Simon's cock at least once and was hoping for another go. Madge also stared at my semi-nakedness, her eyes lingering on the exposed portions of my tits. She left the room after depositing the meal on a small table before us.

After we attacked and put away the fine meal, Simon and I dressed and retook our seats on the sofa. To my surprise, Simon prevented me from sliding back into the silk panties, opening a side drawer on his desk and pointing to the small, opened space with his index finger. Although he did not speak, it was clear Simon wanted the panties as some type of trophy. As instructed, I laid the silky garment in the drawer and completed dressing.

I believed It was time to discuss my future, and now that I'd not only swallowed his cock whole, but fucked him in the same fashion, I felt I was owed an explanation as to where I would find myself in a week. I wanted to know just how much Peyton had disclosed to his father, and whether or not I should return to the United States.

"Yes, well, let me say that, despite this afternoon, my dear," Simon said as he poured two cups of after dinner tea, "Peyton's tale of attempting to purchase the talents of a prostitute is very unsettling to his mother and I." Simon turned to me, his expression the same as it had been once before when I witnessed him dressing down a hotel valet. "And the fact that you allowed him to give you the slip, so to say, is just as disappointing." He turned fully toward me now, his expression stern and uninviting. "So, as I told you before, how do you plan to atone for my son almost making what surely would have been a costly, costly mistake?" When I didn't respond, Simon asked, "And further, what if there had been cameras there? What if the media had gotten wind of all this. I dare say it would be bad for all of us, particularly you." All I could do was to sit quietly, understanding that Simon neither desired nor would accept anything I had to say at that moment.

It dawned on me then the true reason I had been summoned to Simon's office. It had nothing to do with fucking his youngest son, which neither Simon nor Pamela seemed to know about, but, rather, the fact that Peyton had informed his mother and father that he'd attempted to hire the services of a prostitute and failed miserably at doing so. Fortunately for me, Peyton had been more than selective in describing his train journey to London and had mentioned nothing about me chasing the hooker away. In his selectiveness, Peyton had also, however, neglected to describe the sexual lessons I'd provided him. It was then I realized that for now at least, my job was secure, and I had nothing to worry about. It was as if the weight of the world had been lifted from my shoulders. I smiled broadly, and assured Simon that on any future journeys with his son, I would be more vigilant and keep Peyton completely under my direct supervision, never once letting him out of my sight. Simon seemed to accept my apology, and stated, "Yes, well, Jan, I must tell you this little fiasco has cost Peyton the opportunity to attend any of the ceremonies he was scheduled to participate in. Pamela and I have ordered him to return to Brighton and await our return." Simon snapped his wrist to his face, studied his watch, and said, "He should be two hours from London by now." Again, another wave of relief washed over me, and I felt as if everything would turn out alright after all.

Simon, however, was not finished with me. Staring intently at me, Simon said, "Pamela and I have also agreed that you should remain here in London for the next three days in order to give Peyton a chance to clear his head. It's the end of the term, and he will be packing his bags for the family's annual trip to Scotland. I want him to endure no distractions, which I feel your presence may confront him with." His mouth now silent, I realized I was being dismissed, and so, stood on the same four inch heels I'd worm while I sucked Simon's enormous cock into my pussy, made my way silently across the room, and left Simon's office. Moments later, I was back in a taxi, making my way back the hotel after one very incredible afternoon. I simply could not believe my very good luck. It felt as if I was walking on clouds as I entered the hotel lobby, elation and happiness surrounding me like a coat.

Along the way through London's streets, I couldn't help but think about what I'd done just a few hours before. Yes, I still had a desire for younger men, but I also realized that by fucking Simon, a man who was twenty-five years older than me, I'd stepped into the same situation in which I'd placed Henry, Nicholas, Brandon, and now, Peyton. In essence, Simon fucking me and me riding his massive cock was the same as what I was doing to my young lovers, but in reverse. It was evident, then, that Simon Lake had a desire for younger women. So by engaging in sex with Simon, a man who was already an adult when I was born, it was actually no different than me, at sixty years old, fucking Henry, Nicholas, Brandon, and Peyton. On the day they were each born, I'd already entered and engaged in adulthood, with a career in teaching. It dawned on me that Simon and I were no different at all as the taxi sped through the streets. Leaving the taxi at the hotel entrance, I stepped forward in a trance, wondering how or if I could reconcile that newly discovered fact with my conscious.

But I stopped short in the lobby when I heard a woman call my name. Turning to my left, I saw Pamela Lake approaching me with a young man on her arm. As usual, Pamela was dressed exceedingly well, her short skirt accentuating her seventy-five year old figure. For the first time, and I'm not sure why, I noticed Pamela's cleavage, exposed below her chin, the long gash between her tits convincing me that the wife of Simon Lake had surely had breast implants at some time in her life. She rushed to me, embraced me, and planted a kiss on my right cheek. As she backed away from me, her face was all smiles.

"Oh, Jan, how grand it is to see you!" Pamela exclaimed, her hands resting on each of my arms. She allowed her eyes to travel the length of my body, possibly assessing my appearance, but making no effort to conceal what she was doing. Then, without breaking her smile, the billionaire's wife leaned in close, and said in a mock whisper, "I trust your meeting with Simon went well?" I had no idea what to say or how much Pamela knew about the hours I'd just spent in Simon's company, but I had no desire to push the topic and find out, either. Then, without breaking stride, Pamela turned to the young man who'd been standing quietly beside her and said, "Oh, lord, Jan: where are my manners? Here, allow me to introduce you to my favorite nephew, Zach." As I stood in the lobby of this expensive, swank hotel, panty-less, my cunt swollen and bruised from the beating Pamela's husband had given it with his massive, monster cock, I couldn't help but quickly self-appraise Zach.

He stood taller than Simon, and was at least six feet, five inches tall. Like his mother, however, his hair was a brilliant blonde in color. Thick arms stretched the limits of his blazer, as did well-muscled thighs in his trousers. His eyes were a blazing blue, seemingly capable of seeing deep into a person's soul. The young man was as fit as his cousin, Peyton, and surely as distinguished. He exuded an air of charm and intelligence, and I found myself liking Zach immediately. The young man was surely no older than a day past nineteen, yet he exhibited a sense of worldliness not often found in men of such young years.

Zach bowed at the waist slightly as he took my hand and pressed his lips softly against the back of my hand. Returning to a standing position, he said, "Hello, Mrs. Adler. Aunt Pam has spoken so often and so kindly about you that I insisted that the next time you were in London that she was to introduce me to you." Another slight bow, and with his intense eyes burning into mine, he said, "I expect we shall get along famously."

"Yes, I agree," Pamela interjected, bringing me from my revelry as I stood between Pamela and her nephew. She also confirmed my beliefs when she stated that "Zach attends London University, Jan, and hopes to be a professor like you." Zach confirmed Pamela's statement by nodding his head in agreement. But Pamela, always one to play the role of drama queen and gossip monger, leaned in and said, dramatically in a loud whisper, "And for being only nineteen years old, he certainly fancies himself as the lady's man!" Pamela and Zach each laughed aloud, as if they were sharing some family secret. The three of us remained in the lobby for several more moments before Pamela asked if I'd accept her invitation to dine with she and Zach later that evening. The three of us walked together to the private elevator reserved for Simon and his family members, and entered the small car as it rose slowly to the topmost floor. Little did I know that such a short ride in an elevator would provide me with the fuel for my next sexual adventure.

But to hear more, you'll just have to tune in and read about it.