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‘Tis the Season to be Servile, Ch. 06

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 Uber was fifteen minutes late, giving me still more time to contemplate the ineffable humiliation at hand.

I regarded myself critically in the large mirror in the foyer of the mansion. The uniform Natalie selected was indeed quite short, the white petticoats coming down only to my mid thigh. The Dolce the same is true when my legs scrape together while walking in them. Sensual and shameful. Even before Lorena laced up my corset — oh, how she seems to relish vigorously pulling the laces! — and even before putting on my uniform, these luxurious stockings made me feel weak-kneed and docile. Even more so when Lorena adjusted my seams, gently moving her hand across my inner and outer thigh. More so still when she (not gently) pinched my ass through the nylon and then smacked it sharply with her hand to discourage my squirming while being pinched.

Before I put on my stockings, Lorena had already changed my cock cage per Natalie’s instruction. Whereas Mason determines most of my required chores and punishments, it is Natalie who is generally in control of my attire. This extends to what chastity cage I wear, as I have seven different kinds. It isn’t as straightforward as wearing a different one for each day of the week, although there are some weeks it works out that way. Aesthetically, Natalie is quite fond of pink chastity cages, no doubt for the enhanced emasculation effect. I usually am required to wear a pink studded collar along with one of my pink chastity cages — often with pink thigh high stockings and a pink bodice or corset — as color coordination is important to her. I am generally dressed this way in the evening hours, when my traditional maid duties for the day are largely complete and I am called on for more intimate duties in the boudoir or in Natalie’s and Mason’s bedroom (more on that later). Natalie keeps threatening to have Gina and Lou make me a pink and white maid’s uniform, but has not yet followed through with it; I am certain that it’s just a matter of time. I have two pink cages, the plastic Pink Stripe Cobra and the silicone Perverse Pink CB-6000. Aesthetics are only one consideration, however, as the pink cages are not as secure as the stainless steel cages, of which I have four: a gold stainless steel MAMBA, a Gienocy mesh cage with “ergonomic” design (silly marketing — what could possibly be ergonomic about imprisoning someone’s cock?), a Jail Bird (with punishment pins), and a black DOMINIX Deluxe. My seventh cage is a transparent CB-6000S. Natalie recently found a man in Canada who designs and constructs custom stainless steel cages, known to be virtually inescapable. She sent him my measurements (a probable Christmas gift for me, I concluded).

Natalie directed Lorena to replace the mesh cage I had been wearing the previous two days with the black DOMINIX Deluxe. After informing Lorena of her choice that morning, Natalie said to me, ominously, “I quite like the look of the DOMINIX. It’s an elegant design. You want to look your best for this very special occasion, Henrietta.”

The implication that my cage might be seen by my son, or by the sizable gathering of Thanksgiving dinner guests, was unmistakable — and at once chilling and shamefully arousing (that confounding hot cold dichotomy again!). I do have to admit, however, that Natalie is correct about the visual appeal of the black DOMINIX. With its curved shape, spaced rings, conspicuous padlock and subdued black finish, it is one of the more aesthetically pleasing chastity cages I have seen. However, at 3 inches, it is decidedly less comfortable than it is visually attractive. I was permitted to thoroughly clean myself before Lorena put me into the the DOMINIX. As was her practice, she wrapped a thick rubber band around my balls so they would jut out, making it easier for her to push my testicles through the base ring.

Having escort bursa been denied sexual release now for nearly five weeks, I had grown increasingly desperate and had to will myself not to ejaculate onto Lorena’s hands as she manipulated my genitals into the cage (at such times I usually tried to visualize spreadsheets from my old investment fund). Five weeks of being in a nearly constant state of frustrated arousal with zero relief had put me in a precarious mental and physical state; I couldn’t trust myself. I knew that unauthorized ejaculation would result in severe punishment by Mason, especially since my unusually long period of denial seemed to be quite deliberate on the part of Mason and Natalie, no doubt intended to bring about the unsustainably desperate state of mind in which I presently found myself. For what purpose? To make me so desperate that I would involuntarily ejaculate at such a moment as Lorena touching and teasing me, thus inviting punishment? Or to prime me for some incredible act of self abasement as a way to convince Mason and Natalie to finally grant me release?

Because that was the way it typically worked. I would have to formally petition my master and mistress to unlock me and allow me to unburden myself, so to speak. Like much else with them, this was an elaborate ritual. I would usually approach them as they relaxed in the living room, curtsy and “bend the knee” before beginning to make my case. Sometimes my request was summarily denied. Other times, quite rare, it was casually approved. More often than not, however, I was required to grovel for an extended period of time — promising to perform special humiliating tasks for them above and beyond my usual endless list of humiliating chores; or to kiss and massage their feet, or bathe their toes with my servile tongue, removing the lint or toe jam from between them; or to offer up my back as their ottoman for the duration of a movie. My, how Natalie enjoys watching me worship and/or tend to the feet of my former rival? Such a primal display of dominance and submission, of triumph and defeat. And when I finally am granted permission to come, it is generally under extraordinarily degrading conditions: humping the floor at their feet in a pair of tights, as Mason smacks my bottom with his riding crop; lying prostrate on the floor, with their feet covering my face as I touch myself under their bemused gaze; Natalie using one high heeled shoe to pull the chain attaching my nipple clamps while grinding the other into my panty-clad cock and balls; the two of them verbally abusing me as I stroke myself while standing nakedly before them. Recently, Mason actually made me hump his long riding boot as he and Natalie stood above me making out like love-struck teenagers. You get the idea.

Or did they have something even more diabolical in mind in imposing upon me this prolonged period of deprivation? Up until then, only Natalie and Mason had been present during my humiliating petitions and releases (although once I could swear I heard Lorena’s s muffled giggles from some hidden place in the room). Who knows what mortification for me my wife and her lover were planning this holiday weekend.

Even though my visualization of the spreadsheets was successful, Lorena had still found it necessary to rub an ice cube over my cock in order to fit it into its cramped, black cell that morning.

These were thoughts that flitted through my addled brain as I examined myself in the mirror, awaiting Ryan’s arrival. However, I did note with a fleeting moment of pride that the combination of the corset, my diet and all of the exercise I had been getting from my near constant domestic toil was having the desired effect on my body. My figure was slim and my legs were shapely and firm beneath their sheer facade. My hair had grown out and Lorena had applied subtle makeup to my distressed face. I think it is honestly fair to say that there are many worse looking maids, sissified or not. Yet, as soon as I felt a tinge of pride at my appearance, it was washed away with a wave of shame. What kind of man could possibly feel pride at how he looked in a maid’s uniform? Perhaps I truly did deserve all the emasculation (as Natalie frequently told me).

Ryan texted Natalie when he was a mile away from the mansion, so she and Mason walked past where I was standing in the foyer to go outside to greet him. It was a sunny, unseasonably warm day, if quite breezy.

As she started to walk outside, Natalie paused to say to me, “Henrietta, when Mason and I walk down the steps to the car, you will remain on the porch standing at attention with your head bowed. You will be silent while I welcome my son home, reintroduce him to görükle escort Mason and at least let him know that there have been major changes around here since he was home last Christmas. That way, it hopefully won’t be a total shock when he first sees you. Once I’m ready, I’ll snap my fingers. That will be your cue to approach him, welcome him respectfully — with a curtsy, naturally — and offer to take his bags up to his to his room. Mason and I will then take Ryan into the sitting room and bring him up to speed on all of the interesting developments over the last seven months. You do agree that he will find them interesting, don’t you, maid?” she said with a wicked grin.

“Very interesting, no question, Mistress,” I replied.

She laughed with delight, adding, “You will serve tea and cucumber sandwiches while the three of us chat. After all, he has been living in the UK for the past four years. We want him to feel completely at home. Do you understand?”

“Yes, Mistress,” I said with a curtsy.

“See that you do,” said Mason firmly.

“Yes, sir,” I replied, curtsying again. It was the next curtsy that I truly dreaded.

I followed my wife and her lover out of the house as the black Mercedes pulled into the driveway, determined to follow Natalie’s instructions to a T. The last thing I wanted was to give them any pretext to punish me in front of my son. I knew rationally, of course, that it was just a matter of time before that would happen, but was determined to delay it as long as possible. Flawless obedience and obsequiousness would be required for me to have even the slightest chance of success. My life now was really all about humiliation mitigation: humiliation was inevitable, but how could I manage to suffer the lesser of two (or frequently more) terrible options?

The wind blew against my legs and tousled my maid’s cap, as I stood on the porch. Such a surreal experience, waiting to greet my son, not as his father, the respected head of the household, but as the family maid. And not as the type of beloved maid who is almost like a member of the family — like Alice on The Brady Bunch (although she did wear a maid’s uniform and apron, as I recall) — but an actual member of the family downgraded to the role of a lowly female servant right out of Upstairs, Downstairs. Compelled to address my superiors with the same formalized deference as the domestic help in an old manor house. But unlike such help, I was not simply a member of the lower classes who needed employment, but someone who was forced to serve in order to avoid an even worse fate in prison. And worse still, a sexualized, feminized figure of ridicule (as Natalie had accurately described me yesterday).

Still keeping my head bowed, I surreptitiously glanced upwards to watch Ryan emerge from the car. The first thing that struck me was how much taller he was than just 11 months ago. It wasn’t until I saw him with his coat off in the sitting room that the remarkable effects of his bodybuilding became apparent to me.

I was able to catch most of the conversation as Natalie greeted “her son” — he was my son, too, damn it all (wasn’t he?) — as I stood on the porch, partially obscured from their view by a large, potted juniper. Mason stood back a few steps from Natalie and Ryan to give them a moment together.

“Welcome home, honey. Oh, how I’ve missed you! ” said Natalie, as she warmly embraced him.

“I’ve missed you too, Mom. Where’s what’s his name?” Ryan responded.

“You mean your father? It’s too funny that you refer to him as ‘what’s his name.’ You’ll see why in a minute. There have been so many changes since you were last here. Truly life altering changes,” said Natalie.

“What do you mean by ‘life altering’? Good or bad?”

“Oh, definitely good! At least for you and me! I’ll explain everything to you in a few minutes when we sit down inside. How does some high tea sound, my part British boy? Or, young man, I should say. I keep forgetting you’re 18 now!”

Ryan smiled warmly. “It sounds great! I’m starving. How did you know I really like having tea now?”

“Well, besides having tea when with you when I last visited you in Kent, one can’t live in a different country for four years without picking up at least some of the local customs. I’ve always liked tea, too. I have a weakness for scones.”

“Me, too!” Ryan said, with a laugh. I had always resented how well Natalie and Ryan get along, and the easy, playful banter that characterizes most of their conversations. I rarely had that, with either of them. Tense and/or awkward exchanges were more common in my interactions with both of them.

“Well, now that you’re home, we can have afternoon noon tea whenever you want and high tea every weekend. You won’t have to a lift a finger, except to eat and drink, of course.”

“Awesome. But I’d feel guilty having Lorena wait on me all the time. She’s so nice. Where is she?”

“Inside. You’ll see her in a few minutes. She’s missed you. But don’t worry about her waiting on you. That’s one of the many things that have changed around here.”

“You have me intrigued,” Ryan responded.

“Great. Meanwhile, you remember Mason Draper, don’t you?” Mason stepped forward, with his hand extended. “Your father’s old work colleague.”

“Nice to see you again, Ryan,” said Mason, shaking Ryan’s hand enthusiastically. Mason is one of those guys who shakes your hand like he’s trying to break it. “You have a nice, firm handshake. Good. Nothing like your father. Shaking his hand is like gripping a wet noodle.”

Ryan laughed. “I remember you from a couple of my father’s work picnics. You and I threw a football around for a while. But the way I remember it, you weren’t so much his work colleague as his work enemy. He used to call you some pretty awful names.”

“Your father is very competitive, especially with Mason. Or WAS very competitive, I should say. That contest is definitely over, as you’ll see soon enough. One of the big changes I was referring to, honey, is that Mason and I are very, very much in love. We have been for years now, but we no longer have to hide it,” said Natalie, grasping Mason’s hand and looking up at him adoringly.

Mason and Ryan were nearly equal in height, both around 6′ tall or so.

“Wow, that IS big news. What does dear daddy think of that?” He said “daddy” not with affection, but rather with sarcasm, or perhaps more accurately, derision.

“I imagine he is less than thrilled. But you can ask him for yourself.” Natalie then snapped her fingers. The moment I had been so dreading had finally arrived.

I hurried down the porch steps to where Ryan, Natalie and Mason were standing in the driveway.

“Welcome home, Master Ryan,” I said, dipping into a deep curtsy. “Please allow me to take your bags to your room.” It is impossible to overstate how absurd, how diminished I felt at that moment.

Ryan regarded me incredulously, his eyes wide, looking me up and down. “What the fuck? Is this some kind of joke?”

“No joke, honey. The new normal. I told you your father resigned from his position at his firm in March. This is his new job. Since March and from now on,” said Natalie.

As I reached for one of his suitcases, Ryan pulled it it towards him and said to me, sharply, “Don’t touch my things! You disgust me. Get out of my sight.” Certainly his words stung, but they did not shock me. What was the appropriate reaction for a young man seeing his father dressed as a maid?

“I know it’s a lot to take in, honey. But calm down. Once we explain everything to you, it will all start to make sense. And then I think you’ll quickly come to appreciate the advantages — the appropriateness, really — of the new status quo.”

Glaring at me, Ryan said, “The summer before I left for boarding school, I found this bag of panties and nylons and stuff in your desk drawer. That time you caught me in your sacred, forbidden office that you always made such a big deal about. You lost your mind and grounded me for weeks, totally ruining my summer. I thought maybe you’d been cheating on Mom or something, but I wasn’t sure. So I kept my mouth shut. Now I know you’re some kind of sick pervert.”

“Oh, that’s quite interesting!” Natalie said. “We learn new things about each other all the time, don’t we maid?” I was unable to utter a response, at that moment, even though I was usually expected to respectfully respond to Natalie’s questions, rhetorical or not. Turning to Mason, she then said, “Perhaps there’s some truth to our official story after all. Apparently, Henrietta has secretly enjoyed dressing up for quite some time now.”

Mason laughed, “It sure sounds that way.”

Ryan said, “Henrietta? Did you actually just call him Henrietta? Haha.”

“That’s his name now, honey. Well, not legally. At least, not yet. But that’s what he goes by now.”

“Unbefuckinglievable,” said Ryan. “Don’t you mean that’s what ‘she’ goes by now?”

“Well that’s an interesting question, dear. Mason and I call the maid both he and she, depending upon our mood. The way we see it, he’s not really a proper man. And she’s not really a proper woman. Haha. The maid fails at being either.”

“He was never a proper man. He’s pathetic,” said Ryan with a sneer.

“Let’s go inside and have tea. We have so much to talk about. But do let the maid take your things, honey. It’s his job,” said Natalie.

Ryan reluctantly released the grip on his roll-on and put down his duffel bag on the pavement. He then addressed me, “You can take them up to my room, I guess, but don’t you dare open my bags or touch any of my things.”

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