Tis the Season to be Servile, Ch. 10

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‘Tis the Season to be Servile, Ch. 01

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 futher. 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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As humiliating as it was standing in my penance position before the four young women, it was somehow even more degrading to remain there for another half an hour after their departure. This was the first time I had been alone with Ryan for any extended period since his return from the UK. You must admit, it was not the typical father-son bonding experience: a father standing against the wall wearing sheer stockings, high heels and a chastity cage, baring his red ass to the son who had just whipped him, as the latter reclined comfortably on a chair, the two of them not exchanging a word.

After he finally gave me permission to end my penance, I put back on my uniform, curtsied to him, and thanked him for correcting me. I then requested permission to be dismissed so as to be able to go about my chores around the mansion.

He barely looked up from his iPad as he said, “You are dismissed, maid. Be sure to tidy up Miss Piper’s room before she returns from shopping.”

“Yes, sir. Thank you, sir,” I replied, curtsying deeply, before I left the room as quickly as possible.

I immediately changed into my working maid uniform. After cleaning up the kitchen and tidying up the guest bedroom where Piper was staying, I went up to the master bedroom — my former bedroom — and began dusting and shining Natalie’s extensive collection of shoes and boots. After that, I did the same for Mason’s smaller, but still considerable, collection of footwear. This was not because their shoes were dirty. Indeed, not two weeks earlier, I had performed the same tedious chore (and most of the shoes had not been touched since then). The purpose of this unnecessary task, of course, was to further abjectly ingratiate myself with my mistress and master in the hope that they might, at long last, grant me release.

Release here having a dual meaning — release from the prison that surrounds my cock and sexual release. The latter is dependent on the former, of course, but being liberated from my chastity cage by no means guarantees that I will be permitted to have an orgasm. Or rather, I should say, Natalie and Mason sometimes find it entertaining to ruin my orgasm, so that what should by this point be a flood, a deluge, ends up being only a trickle. Being locked up again immediately following a ruined orgasm sometimes leaves me as frustrated and desperate as before (perhaps even more so). That said, a ruined orgasm is better than no orgasm at all; beggars can’t be choosers after all (and has there ever been someone who is more of a beggar than what I have become?). After being denied release for such an extended period, I was hopeful that this time I might be granted a modicum of mercy and be permitted a fulsome ejaculation, no matter how humiliating the means — because knowing Mason and Natalie as I do, there is no doubt that a steep price will be exacted for any mercy granted. No price was too high, however, as living in a feverish state of nearly constant, frustrated arousal was driving me mad.

The superfluous nature of the ingratiating task I complete matters not. It is the fact that I am performing the act of a lowly bootboy that matters. Indeed, one day in early October, Mason had ordered me to polish the same pair of his boots three times in succession — not because I had done a poor job the first two times, but simply because he could (and because it amused Natalie). This December afternoon I could have sat on the floor to polish the shoes, but when I tried to do so, the fresh sting on my bottom caused me to conclude that the discomfort of working from my knees was preferable. Why not sit on one of the chairs or footstools in the cavernous bedroom while I cleaned, you may ask? Well, in addition to the fact that even sitting on a cushioned seat would be painful in my present condition, I am not permitted to sit anywhere in the mansion except in my maid’s quarters. Natalie is adamant that a maid’s role is to serve, not sit. The risk of sitting on the furniture when Natalie and Mason are not home is too high. Besides the possibility of being caught by Ryan, I am fairly certain that Mason has installed little cameras throughout the mansion to spy on me escort bursa (while dusting I had seen some, even though they were cleverly concealed). The tech-obsessed Mason is fond of using technology to subjugate me. I have no doubt that he views it as a form of poetic justice, since it was his overextension in the tech sector (against my warnings) that led to his demotion at the firm all those years ago when he was forced to report to me. As much as I enjoyed making his life miserable during that period, I must say that, in retrospect, I wish I had been more gracious in my temporary victory. Because Mason is now teaching me just how truly miserable life could be.

To highlight my efforts, once I finished with their shoes, I tied a little red ribbon on the strap of one of Natalie’s Louboutin sandals and left it in front of the closet that stored her shoes. I then did the same around the top of one of Mason’s Lucchese alligator boots. Realizing that they and Piper would soon be returning from their shopping trip to Manhattan, I next hurried down to the kitchen to begin scrubbing the floor (which I had mopped two days earlier) on my knees. It was my plan to be thus occupied when they returned. Completing the tasks of bootboy and scullery maid, the two lowest servants in a wealthy household of earlier times (Natalie was quite nostalgic in that way) without being told to do so, would surely earn me some points in the groveling department, I hoped. As I worked, I distracted myself by trying to decide which part of my anatomy was causing me the greatest discomfort: my aching knees, my stinging ass or my cock straining against its cage. As usual, my treacherous cock won this contest (or, I should I say, lost it).

It was 4 PM when I heard the front door open and the voices of the returning shoppers in the foyer. The three of them and Ryan then entered the kitchen, where I was pushing a scrub brush across the floor next to the stove.

After I was sure they noticed me working, I got up off the floor and curtsied to them, “Good afternoon, Mistress, Master, Miss Piper. My sincere apologies for not being properly dressed to serve you, but I took the liberty of cleaning your shoes, Mistress and Master, and am now scrubbing the floor, as I know how fastidious you are, Master, when it comes to clean floors.”

“See, I told you Henrietta would be in full kowtow mode. He always is on petition days,” Natalie said to Mason, smiling. I was hoping that the three of them had not discussed this subject on their shopping trip. It was bad enough that my “petition day” was even mentioned in the presence of Piper and my son.

“Perhaps we should have them more often, then,” said Mason. “It doesn’t mean that we have to grant his petitions any more frequently.”

“True enough. It IS fun to see what lengths he will go to as he becomes increasingly desperate,” Natalie said. She then turned to Ryan, “Did you have a nice time with Daphne and her friends, honey?”

“Yes, quite,” Ryan answered. He had picked up some English affectations during his time at boarding school, even a trace of a British accent. His mother finds it charming; I find it annoying.

“Did the maid behave himself?” Natalie asked.

“Unfortunately, no. Three demerits. It was necessary for me to take corrective measures, I’m afraid,” my son responded.

Piper perked right up at these words. “What, pray tell?” she inquired.

“Well, corporal punishment followed by directing the maid to stand in disgrace in the presence of the young ladies. But don’t worry, Mom, I didn’t leave any welts in case you want him caned him on Christmas Day or something. Your ‘blank canvas’ and all,” he laughed.

Natalie was beaming. “I’m delighted! But you needn’t have worried, honey. Welts on top of welts can also be aesthetically pleasing. They have somewhat of a painterly quality. Sometimes Mason’s artistry on your father’s ass reminds me of a Van Gogh, especially after multiple canings over a short period of time.”

Piper giggled at Natalie’s ridiculous comparison. “Like The Starry Ass, you mean?”

Natalie laughed. “More like The Sorry Ass, dear. But you get the picture. Ryan, I’m so happy that you’re getting comfortable disciplining him on your own. I just knew you’d quickly come to see how natural it is. And satisfying.”

“Satisfying is a good word for it. I hope you don’t mind, Mason, but I tried out the new Lochgelly tawse you bought,” Ryan said.

“I don’t mind in the least. I’m glad you started to break it in. How was it? Effective, I hope,” Mason replied.

“Oh, very! Three stokes were enough to make the maid dance,” Ryan laughed.

“Excellent,” said Mason. “I bought it from John Dick Leather Goods in Scotland, the inventor of the Lochgelly, dreaded by generations of Scottish schoolchildren. The shop is now run by the granddaughter of the founder. I bought the heavy duty version. They also have medium and light duty versions, but I figured the heavy one would be more, shall we say, persuasive.”

“It’s görükle escort definitely persuasive. The craftsmanship is excellent,” said Ryan.

“I look forward to trying it out myself sometime soon, “said Mason.

“Henrietta, do share with us YOUR review of the tawse,” said my wife, tittering.

How humiliating. I replied, “As Master Ryan indicated, Mistress, the tawse is highly effective. Especially when wielded by someone as powerful and as proficient in its use as Master Ryan.” I could not meet their eyes as I uttered these words, standing before them in my working maid’s uniform, my flesh-toned stockings still wet with soap suds from where I had been kneeling moments earlier.

“That’s good to hear, although your tears, screams and pleas for mercy are a much more accurate representation of your true feelings about such things than your words, I suspect,” said Natalie.

Mason said, “No doubt. But reviewing an instrument of correction is like reviewing a restaurant. It’s not fair for a reviewer to eat at the restaurant only once before writing a review. So, Henrietta really needs to feel the tawse on his backside several more times before he can objectively review it.”

“I’m sure the maid will get plenty of opportunities for that between the two of you,” Piper said, smiling at her father and Ryan.

I finished scrubbing the floor as the four of them chatted in the kitchen, then hurried to my maid’s quarters to shower and change into one of my serving uniforms and a pair of seamed, sheer black stockings.. I then served the two couples cocktails and dinner. The perverse soap opera quality to the situation kept occurring to me throughout the evening. Here I was, in this unspeakably diminished state, a feminized male serving as the maid to my wife and her lover as well as to my son and his lover, the daughter of my wife’s lover. So surreal, like The Brady Bunch in hell.

After dinner, Ryan and Piper went out. Where, I had no idea, but I was exceedingly grateful as it was nearly time to begin my ritualistic groveling for the two releases that — like that old Rolling Stones song — I no longer simply wanted but now truly needed. My sanity depended on it. I entered the living room carrying a tray with a bottle of 2017 Opus One Cabernet Sauvignon and two glasses. I stared down greedily at the bottle. I am very fond of high-quality, full-bodied red wines, but hadn’t had a drop since my radical change in status; Natalie felt strongly that the empty calories were not conducive to me maintaining the “girlish” figure she expected of her maid.

Mason and Natalie were seated on the couch next to each other, still dressed in the clothes they had worn shopping: Natalie in a red sweater and a short, black skirt with black fashion tights and Mason in dress pants and a polo shirt. Natalie’s stocking-clad feet were propped up on the coffee table next to Mason’s socked feet, both warmed by the picturesque fire roaring in the enormous nearby fireplace. They ignored me as I curtsied to them, served them the wine, and added a couple of more logs to the fire.

I then got down on bended knee before them and addressed them. I was eye-level with their feet and made a point of looking at their feet rather than looking them in the eyes as I spoke. Plainly visible above Natalie’s right foot was the anklet from which dangled one of the keys to my MAMBA chastity cage; Mason held the second key somewhere.

“Thank you, Mistress and Master, for your kindness in granting me this opportunity to humbly petition you. As you know, it has now been more than eight weeks….”

“I’m surprised he doesn’t know the number of days and hours,” Natalie interrupted, smiling at Mason. “Carry on, Henrietta.”

“Yes, thank you, Mistress. It has now been more than eight weeks since I was permitted to have any kind of sexual release…” I continued.

“Do you mean cummies?” Natalie asked.

“Yes, Mistress. It has been more than eight weeks since I was permitted to have…cummies and…”

She interrupted me once again. “And what exactly makes you think you deserve cummies?”

“I have tried very hard to be obedient, Mistress. I have tried to endure the recent changes…”

“You mean the return of Ryan? Who is he, Henrietta, your son or your master?” Natalie interrupted still again.

“He is…my…my…he is both my son and my master, which is what makes the situation so…so… incredibly…difficult, Mistress. It is a…a perversion.”

“No, you are completely incorrect, Henrietta, as usual. You are slow to learn but we shall see to it that you do, eventually. Learn the hard way, right Mason? What would truly be a perversion is if such a contemptible, morally corrupt and physically inferior pansy as you were any kind of authority figure whatsoever to Ryan. That was the charade before he went off to boarding school, but never again. We lived in a perverse state for all of those years when you pretended to be a real man, a powerful man. We must now make up for lost time,” Natalie said, ominously. “Now, I strongly suggest that you resume your explanation of why it is you believe you have earned your precious cummies, without any further complaints.”

“Yes, Mistress, please forgive me,” I said, curtsying deeply. “I have tried hard to obey all of Master Ryan’s and Miss Piper’s commands. I have tried hard to provide a high level of domestic service. I have adhered strictly to my diet. Before she left for Christmas break, Miss Lorena said she was able to tighten my corset an additional inch.”

“Go on, what else?” Natalie said.

“As I explained earlier, Mistress, I took the initiative to scrub the kitchen floor today even though it was still relatively unsoiled since I had cleaned it the day before yesterday. I did the same with your and Master’s footwear. I have been mucking out the stalls for your, Master Mason’s, and Master Ryan’s horses twice a day rather than the once a day I am required to do so; that is very time consuming, Mistress. I repolished the bannister on the main staircase after only a week. Two days ago, I took the initiative to polish all of Master Mason’s leather punishment implements with dubbin.”

“I like that. Taking an interest in the quality of his discipline,” interjected Mason. I just knew that such an unspeakably servile act would appeal to Mason, bastard that he is.

“Mason and I will take your petition under consideration while we enjoy our wine, Henrietta. You are very fond of Opus One, if I recall correctly. It’s no wonder; it’s quite yummy,” Natalie said, twirling the wine in her glass and taking a healthy sip. “Meanwhile, make yourself useful. We spent several hours walking around the city shopping and our feet are tired and sore,” said my wife.

“Start with your mistress’ feet, maid,” ordered Mason.

“Nose to toes first, Henrietta. I just removed my boots a few minutes ago, so I think my stockings are still a bit moist,” said Natalie, smiling.

“Yes, Mistress, of course,” I said, as I crawled on my knees closer to her feet and, and pressed my nose against the nylon-covered toes of her right foot. I inhaled audibly. This was not a distasteful experience for me. Natalie’s stockings were indeed quite damp, but I found the musky odor to be alluring, especially as there was still a lingering scent of the fine Italian leather of the boots she had worn most of the day mixed with the smell of her sweat in the nylon. My cock throbbed insistently as I inhaled. Natalie began kissing Mason.

After a few minutes, she broke off her kiss wetly from Mason’s mouth to say, “I think you’re enjoying yourself too much down there. Massage my feet now.” Natalie and Mason continued to drink, kiss and talk as I worked with my fingers and thumbs to relieve the tension in her feet.

Eventually, after I spent about 10 minutes on each foot, she said to me, “That’s sufficient, Henrietta. Now it’s time to do your master’s feet. But I’m tired of seeing you in that uniform. First, put on those festive stockings I bought you last week and your high heeled boots. It’s almost Christmas and it’s time to get in the spirit. You may remove your corset, but bring your nipple clamps as well. Hop to it!”

I stood up and curtsied. “Yes, Mistress, right away!”

“Also bring my new antique riding crop, Hathaway, the one we bought from Suzanne,” Mason ordered.

“Yes, sir,” I said, wondering how much more abuse my bottom could stand in one day.

As I scampered off to my maid’s quarters, I heard Natalie say “‘New antique’ is an oxymoron, darling.”

“Perfect to use on the moronic maid, then,” Mason replied. Natalie’s laughter echoed down the hallway along with the sound of my rapidly moving heels.

How dare he call me a moron?! Me, an MIT grad, one of the greatest analytical minds of my generation. And yet, here I was, his veritable slave. Someone who through a toxic mix of greed, hubris and indiscretion, had lost everything, including my freedom and my manhood. I guess I really was a moron.

In my room, I removed my uniform and put on the pair of bright red tights with a gold snowflake pattern Natalie had purchased. I then put on a pair of black, high heeled boots that came up about two inches shy of my knees. My torso was bare above the stockings, and I felt even more exposed than usual given that my chastity cage — usually hidden by my maid’s uniform and panties — was clearly visible beneath the nearly sheer fabric. Even the absence of the corset, as liberating as it felt in one regard, made me feel more exposed. Still, I took a moment to admire myself in the mirror. Yes, I looked ridiculous, but my body had undergone a remarkable transformation since my servitude had begun seven months earlier; my formerly flabby body, while not muscular, is now at least lean and toned. Perhaps I could write a new fitness book: “The Sissy Maid Workout and Diet” or something like that (although Natalie, and to a lesser degree, Mason, are the ones who impose the dietary restrictions upon me and assign the endless physical tasks, so they would be the rightful authors of such a book). I grabbed one of the pairs of nipple clamps that hung on a peg on the wall next to the punishment implements. I chose the one that I felt was the least painful.

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