Tis the Season to be Servile, Ch. 5

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‘Tis the Season to be Servile, Ch. 05

Note: All characters are at least 18 years old. Similar to Lawyer2Maid (with a more seasonal focus), this is another story about an arrogant, highly successful man experiencing a brutal social downgrade — including being cuckolded and emasculated and becoming a sissified maid to his own family and former colleagues. If this is not your cup of tea, please read no further. If you are of the opinion that for a story to have value, it must be realistic, please read no further. Constructive criticism is always appreciated, but it is not constructive if the reader inherently dislikes or disapproves of the subject matter — especially if he/she continues to criticize the story several chapters in rather than simply stop reading it. Otherwise, please enjoy!

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The fateful day before Thanksgiving — the day Ryan was due to return home — had finally arrived. The five days leading up to it, following my humiliating spanking by my brother-in-law in front of my niece and her friends, had seemed like an eternity.

The morning after that shameful episode (the Sunday before Thanksgiving), to no one’s surprise, Mason did indeed take me to task and punish me for Daphne’s insistent horn blowing in the driveway. Scolding me severely while I served him and Natalie breakfast — making no mention whatsoever, of course, of the actual reason I was late in meeting Daphne — he ordered me to fetch his schoolmaster cane once I cleared the dishes from the table.

I scampered to my maid’s quarters, and took down the stipulated instrument of correction from where it hung on the wall near my bed alongside the other canes, crops, straps and paddles. I was always highly distressed when facing a caning, and I knew from experience how wicked a sting the schoolmaster cane was capable of inflicting when wielded by Mason. However, with Thanksgiving approaching, the thought of having to go about my seemingly endless series of tasks in a state of constant, lingering pain was particularly worrisome. My ass had still not even fully recovered from Scott’s vigorous spanking of the prior evening.

When I presented him with the cane, accompanied by a deep curtsy, Mason said, “Until you learn how to manage your time better, I’m going to continue to punish you like a naughty schoolgirl, Hathaway.”

“Like a naughty maid, you mean,” Natalie corrected him.

“Schoolgirl, maid, whatever. Bend over the counter, legs spread, ass out,” Mason commanded.

Before getting into position, I looked over at my wife imploringly, hoping she would intervene on my behalf due to the injustice of me being punished for being late only because Mason made me late. Natalie did intervene on my behalf, but not for the reasons I had hoped. In fact, her intervention left me cold with fear and dread. At the the same time, however, her words caused my cock to swell shamefully in its cage. You may ask: Cold and hot at the same time? How is that possible? It is, in fact, one of the signature paradoxes of the submissive psyche: that which strikes terror in your heart can simultaneously spark fire in your loins. I often think that of all of the betrayals that I have suffered over the last six months of my great downfall, even those by family and so-called friends, it is the betrayal by my own body — my treacherous cock — that has been the greatest of all. But, in truth, I know that it is not merely my cock that is guilty, it is my mind. It’s funny (well, actually, not that funny) but, given my once celebrated analytical abilities, I had always thought of myself as having a beautiful mind; now, enfeebled and warped are the adjectives that most readily come to mind.

Once Mason lifted my skirt and pulled down my panties, Natalie said, “Darling, I know the maid needs to be taught a lesson, but look. His welts are only just beginning to fade from when you punished him over a week ago for not ironing your pants properly. Thanksgiving is only a few days from now, and I’m almost certain that he’ll be fucking up plenty of times on Thanksgiving day and over the long weekend. We don’t want Ryan to think that we abuse his father…I mean, the maid …do we?”

“What do you mean?” Mason said, as he swooshed the cane in the air, as was his custom before laying into my backside. Despite the agony I know that sound portends, it, too, inevitably causes my cock to stir, as it did at that moment. Yet more treachery from my wayward appendage.

“I think it’s best that Henrietta’s ass be a blank canvas on Thanksgiving so that our guests can fully appreciate your artistry, darling. You are masterful in your use of the shades of red, brown and purple,” answered Natalie. “And black and blue,” she chuckled.

“I guess you have a point, sweetheart. If his ass is full of welts, I’d have to hold back some when he inevitably fucks up in front of our guests.”

“It would be a pity to deprive them of the full experience,” she replied.

“Yes, escort bursa the full monty,” Mason laughed.

Oh, such witty repartee. Always at my expense. Once again, I felt like puking (and, once again, for more reasons than one).

Natalie’s allusion to Ryan seeing the condition of my bottom was jarring. Bending over the kitchen counter, I pondered the staggeringly humiliating implications of what she and Mason were discussing. As has been apparent from what I have revealed so far about my dramatic reversal of fortune, intense humiliation is now my daily bread and butter. But it occurred to me then that every indignity I had suffered so far would likely pale in comparison to the level of unspeakable, almost inconceivable humiliation that awaited me with Ryan’s arrival on Wednesday and on Thanksgiving itself, when I was to serve as the feminized servant to my extended family and former colleagues. And, as Ryan was returning home for the foreseeable future, I saw no end in sight to what seemed certain to be absolutely soul crushing, ego annihilating debasement.

When I think back to the deterioration of my relationship with my son in the years leading up to his leaving the country for boarding school, it really can be boiled down to the question of what constitutes manhood. Despite my vast wealth and power — the wealth and power of a self-made man, which I thought should count for something (a great deal, in fact) — Ryan had never really respected me as a man. To him, my underwhelming physical stature, my lack of athletic ability or interest in sports, my complete ineptitude when it comes to fixing things or building things with my hands all must have been huge disappointments. Especially when he contrasted me to Scott or to the fathers of his friends and other men he knew. None of those deficiencies might have mattered so much if I had spent meaningful time with my son in his formative years, bonding in other ways perhaps (music, art, going to movies or playing games with him, taking walks in the woods together, whatever). But I was so focused on my career that I spent very little time of any kind with Ryan when he was young.

Meanwhile, I attempted to overcompensate for my physical shortcomings by bullying those around me — browbeating Natalie, speaking dismissively to Lorena or to waiters and waitresses in restaurants, belittling Scott and Miranda, imposing my will upon Ryan, etc. “My house, my rules” — or sometimes, even more arrogantly, “My mansion, my rules,” — was a phrase I was fond of repeating to Natalie and Ryan. I had hoped on some level that my domineering attitude would compel Ryan to respect my authority, to realize that I was quite a formidable man after all, not someone to be fucked with. When, in fact, it did precisely the opposite. He saw right through the charade, and did not attempt to hide his growing contempt for me, especially as he entered his pre-teen and teenage years.

Pathetically, if predictably, my reaction to his contempt and lack of respect for me was to double down in exerting my dominance over him and in diminishing him. To, in fact, diminish and stifle his burgeoning masculinity and maturity by spanking him, grounding him, and forcing him to do the menial chores of a servant in his own home. Which, like a viscous cycle, accomplished nothing, absolutely nothing, other than to still further increase Ryan’s resentment towards me and further reduce his measure of me as a man — or a real man, in any case. A wiser individual would have realized this and course corrected. Not I.

So, where did that leave things now? The next time Ryan laid eyes on me, I would be standing before him in a maid’s uniform, an emasculated servant in the home where I once ruled as a quasi tyrant, a home that was no longer mine but HIS — his and his mother’s, and her lover’s home (perhaps not legally Masons’s home yet — he has his own mansion still, which I also clean from time to time — but his home for all practical purposes). Ryan would see me displaced and defeated by my wife’s lover — a man whose physical attributes, interests, and talents were consistent with Ryan’s idea of manhood — the man who was now unmistakably my lord and master. Yes, I thought to myself as I listened to Natalie and Mason decide my form of punishment that morning, Ryan will see me with all of the vestiges of masculinity stripped away. In other words, he will see me as he has always believed I truly am. The real me. Oh, god.

Mason finally agreed that caning me that morning was not the best idea.

“What should his punishment be then?” he asked.

“How about 100 punishment lines?” suggested my wife.

“Not good enough. Hey, I’ve got it. Hathaway, turn around and face me. I want you to write ‘Bimbo maids must learn to manage their time or face the consequences,’ 100 times. Very neatly, of course. I will be checking your penmanship and the uniformity of your lines, as usual,” Mason said.

“Thank you, Master and Mistress, for you generous görükle escort display of leniency. I am truly not worthy of it,” I replied.

“You’re right, you aren’t. But don’t thank me just yet. You haven’t heard all of my conditions yet. Remove your dress. You will write your lines standing here in your stockings, heels and corset. You can use the counter as your desk. Lorena will supervise you. I’m going to ask her to affix a pair of nipple clamps to your pathetic titties and to not remove them until you’ve finished a quarter of your lines. She will then remove them, give you a ten minute respite, and then put the clamps back on again. She’ll do that four times, until all of your lines are completed,” Mason announced with a self satisfied grin.

“Ouch! It’s going to hurt like hell when Lorena takes them off. You’d better write quickly, maid,” laughed Natalie.

“But neatly. Poor form will result in you having to start over from the beginning,” added Mason.

“You’re so clever in devising punishments for the maid, darling,” said Natalie, kissing Mason.

Each time that Lorena removed the nipple clamps over the course the next 90 minutes — the time it took me to finish all the lines — it did indeed “hurt like hell’; in fact, it brought tears to my eyes and me to my knees. Lorena giggled at my reaction, but I am in fact indebted to her, as she loosened the screws on the clamps just a tad after noticing me wince upon her initial tightening. It was that slight adjustment that caused the pain to be merely excruciating, rather than truly unbearable, when the blood rushed back to my nipples. By the third time she reattached the clamps to my poor nipples — tweaking them first with her long, lovely fingers — they were excessively sore and sensitive. By the fourth time, it felt as if someone were holding the flame of a lighter against them. So, it was that pain that lingered throughout the holiday and long weekend, a constant reminder of the unfairness and powerlessness that was now my reality.

At least my lines passed Mason’s inspection, although he threatened to make me repeat them due to one “i” not dotted in the “bimbo” in line 82. He decided to show me some mercy, however, probably because he knew that time spent repeating my lines punishment was time I could not spend doing other things to make his life more comfortable.

Natalie saw it somewhat differently, but I believe that she sometimes finds it just as arousing for her lover to grant me mercy as to punish me, because his ability to do — to truly hold my fate in his hands — is the most tangible evidence of just how much power over me he possesses. And that power is to her, to them, the ultimate aphrodisiac.

“Your master is really much too forgiving, Henrietta. I believe it’s time to bend the knee.”

“Yes, Mistress, of course,” I said, as I got down on one knee before Mason and kissed the toe of shoe. “Thank you again, Master, for your remarkable forbearance,” I said to him humbly, as he regarded me smugly from the comfort of the couch, Natalie snuggled up against him, caressing his thigh.

“Bend the knee” was one of the more common humiliation rituals to which I was subjected. As routine as it was, Natalie never seemed to tire of seeing me genuflect to her lover. Would she derive similar satisfaction from watching me genuflect to my son, I wondered. Could one actually die of humiliation?

I spent the balance of that Sunday cleaning Ryan’s bedroom, which had been mostly unoccupied for four years, and his adjoining bathroom. I dusted and tidied his room regularly, of course, but as he was moving back in, Natalie insisted that I move all of his furniture, books, video consoles, sports trophies — in short, everything in the room — to clean and dust behind them thoroughly.

The next day, the Monday before Thanksgiving, Natalie received a call from Scott and Miranda, who were both quite irate about the increase in their car insurance rate triggered by Daphne’s latest speeding ticket. — due solely to my tardiness, of course. Natalie magnanimously agreed with Daphne’s suggestion that I make it up to them by cleaning their house in Wilton every Tuesday for the foreseeable future. This, of course, would give Miranda, Scott and Daphne ample, recurring opportunities to find fault with my efforts and to punish and humiliate me.

By Tuesday, my contemplation of the magnitude of humiliation I was facing with Ryan’s imminent return and the ensuing family feast had reached a crisis point. In desperation, I approached Natalie in her office when Mason was at work.

After admitting me, Natalie regarded me with surprise, “What could possibly be so important that you’d come and disturb me in my office?”

Preceded by a deep curtsy, I asked, “Permission to speak, Mistress?”

“Well, that’s why you’re here, isn’t it? Go ahead, but be quick about it.”

“Mistress, I know it’s not my place to ask. But I wanted to humbly request…no, I mean I wanted to beg you…” Here I got down on my knees at her slippered feet. “I want to beg you to please allow me be a butler instead of a maid once Ryan comes back. I know I have to be a servant, but please, please Mistress. Please don’t force me to be a maid in front of my own son. To wait on him dressed as a maid. I’m sure we can find a butler outfit in this town by Wednesday. Please, please, Mistress, I know I have to be humbled. But not as a maid! Please, I beg you! I don’t believe I can survive that degree of humiliation.”

Natalie responded with a hearty, if somewhat incredulous, laugh. “You really are too funny, Henry. Henrietta, rather. Of course, you’ll be dressed as a maid, because that’s now what you are. That’s all you are now, and all that you will ever be for the rest of your years. Daphne, Lorena, Miranda, Scott, so many people really, have seen you dressed in your maid’s uniform, serving them — you’ve gotten pretty good at being a maid, to be honest — do you think they’re now going to tell Ryan that you’ve been a butler these past six months? Since your little impropriety. Your little financial faux pas that jeopardized everything we built, jeopardized your son’s inheritance. Because I’m going to tell Ryan all about it the moment he walks through the door on Wednesday. I’m going to tell him everything.”

“Please, Mistress,” I weakly persisted, although I knew she was right. There was no putting the emasculation genie back in the bottle.

“A butler. How preposterous! No, when you greet Ryan on Wednesday, you’re going be standing at attention in one of your finest uniforms, your stocking seams straight as arrows, your heels sparkling with polish, your maid’s cap perfectly straight. You’re going to curtsy deeply to him. You’re going to refer to him only as ‘Master Ryan’ or ‘ sir’ — unless, of course, he tells you to address him otherwise — and you are going to treat him with the exact same level of respect that you treat Mason and me. Do you understand?”

“Please,” I sniffled, tears running down my cheeks.

“You’re beginning to piss me off with your obtuseness. I don’t know what you’re so worried about. Ryan has never really thought of you as a real man. He’s certainly not going to think of you as a woman. He’s going to see you for exactly what you are: a completely emasculated male. Not simply a maid, but a SISSY maid. A pathetic, feminized servant. An object of ridicule and scorn. He may be shocked at first, but I have no doubt that it will seem perfectly natural to him in no time. Remarkably, against all odds, your son is an alpha male.”

“So, so humiliating…I can’t take it,” I whimpered (still thinking, “If he really is my son…?”).

“You have no choice but to take it, Henrietta. I have some advice for you. Since you can’t prevent it — wait till I tell Mason about your butler idea, he will laugh his ass off…As I was saying, since you can’t prevent it, embrace it. Embrace the humiliation. Let the shame flow over you. Wallow in it. Drown in it. We both know that humiliation turns you on; it gets your little cock all excited in its cage. So why not try to enjoy it somewhat? Why not surrender to it?”

“It’s too shameful to even contemplate,” I lied, my cock metaphorically rioting in its prison that very second.

“Well, how you choose to cope with it is up to you. It’s one of the very few things up you, really. But cope with it you shall. Kiss my slipper to show me you understand, or I’ll tell Mason that you’re being obstinate.”

“No, please, Mistress,” I said, kissing her foot repeatedly. “I understand. Please don’t tell Master.”

And that was that.

I spent the balance of Tuesday cleaning the mansion and finalizing my menu, still trying a few different tweaks to the recipes I had selected. Besides the dry brined turkey and the kale salad, mushroom soup and brussels sprouts with pancetta that I have already mentioned, I was preparing sausage, sage and chestnut dressing, cranberry relish, garlic-parmesan cheese roasted carrots, potato gratin, glazed green beans, and pumpkin risotto. Fortunately, Lorena was handling the pumpkin pie, apple cobbler and pecan crescent cookies (as my baking skills were still very shaky).

Which brings me back to that fateful day. The eve of Thanksgiving. The eve of the pulverization of what was little was left of my ego.

Lorena supervised me getting dressed to greet Ryan when he arrived from the airport. Natalie said to her beforehand, “I want him in the shorter of his two formal uniforms, with the Dolce&Gabbana seamed stockings.”

“Please, Mistress, shouldn’t I wear my long, formal uniform to greet Master Ryan and serve dinner tomorrow?” I objected meekly.

“Nonsense. A maid should show some leg. And thigh. You’ll wear the short one.”

“Yes, ma’am,” I said, cringing inside.

Ryan called Natalie from his Uber taxi to tell her that he was scheduled to arrive at the mansion around 4 PM. At 3:45 PM, as Mason and Natalie relaxed in the sitting room, chatting with Lorena, I stood at attention by the door as per Natalie’s instruction, legs pressed together, head erect, listening intently for the sound of wheels on the driveway. Shaking, slightly dizzy. Waiting to welcome my young master home.

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