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‘Tis the Season to be Servile, Ch. 09
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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It is a fascinating thing to witness a strong, virile, young alpha male transition from boyhood to manhood, especially as he comes to realize his growing power — power not only over members of the opposite sex but also over weaker members of his own. Such a realization, especially when positively reinforced, can be intoxicating for the young man and lead to a hunger for still more power. If grievance is thrown into the mix, especially grievance against a former, typically older male authority figure, the young man’s lust for power and lust for retribution can become commingled in ways that can spell very bad news for the former authority figure. At the same time, witnessing this young man exert his newfound power and exact revenge can be enormously entertaining for those fortunate enough to do so. Especially for the young male’s female admirers. Even more so if they share or are sympathetic to his sense of grievance against the now weaker male, stripped of his former power and authority, who is the target of young male’s retribution. And more so still, if the female admirers are potential mates of the young male. To use Natalie’s word (as quoted by Piper), there is something primal about watching the ascendant young male dominate the older man and bring him to heel.
And if the two males in this power inversion have familial ties — father and son, for instance — than there is an element of soap opera in it as well, making it even more compelling to watch play out. It is Tarzan, As the World Turns and a morality play all rolled into one. And, let’s be frank: its appeal lies not in the nobler aspects of human nature. No, its appeal lies chiefly in the audience’s sadistic voyeurism. Although audience participation is also quite common. One of the more subtle forms of audience participation on the part of the young male’s female admirers is to encourage him to be cruel in his subjugation of his older rival. The more the younger man humiliates and emasculates his rival, the more manly he is perceived to be by his prospective female sexual partners in this primal mating dance. The females are titillated by the young male’s display of mastery over his weaker opponent, and often make little or no attempt to hide their excitement. It is quite fascinating really.
As the unfortunate older male in this type of situation, it is perhaps challenging for me to maintain my objectivity as I watch this dynamic play out with Ryan; I am at once an observer and a key participant, Nevertheless, I myself had minored in psychology at MIT (which had proven very useful in my investment career), and these were the thoughts that ran through my head three days before Christmas as I curtsied to my son in front of the gaggle of giggling girls that included my niece, Daphne, and her three friends. These were Daphne’s high school senior classmates (all, like Ryan, recently of legal age and with still raging hormones), including Riley and Leah (who I had already met before Thanksgiving, when I cleaned their footwear and they watched Daphne’s father Scott spank me), and Bella, who I had not met before. Another leggy, slender young woman, although with shorter hair than the others, Bella fit right into the “mean girl” clique vibe that the other three projected, with their bratty, entitled attitudes. Similar to the evening at Daphne’s house, all were wearing short skirts, now with festive fashion tights (green, red, plaid, candy cane striped); Daphne and Riley wore high heels and Leah and Bella wore boots. All four were dressed to maximize the blood flow to my son’s free, and my caged, cock.
It had now been over eight weeks since my last release, by far the longest I had ever gone since I began masturbating at the age of 14. To say that I was desperate for relief was indeed a massive understatement by this stage; I thought about little else and was even finding it difficult to sleep. Mercifully, no more had been said about Piper’s outrageous suggestion that Ryan become my keyholder. I assumed that was simply a suggestion she made in the passion of the moment, which Ryan, upon further reflection, had appropriately escort bursa dismissed; after all, even at the time she made it, he said he wanted nothing to do with “my disgusting, little cock.”
That very morning after breakfast, I had begged Mason and Natalie — kissing their shoes repeatedly before they left with Piper to do some last minute Christmas shopping in the city — to grant me an opportunity to formally petition them for release later in the day after they returned from shopping. This is what I have been reduced to: not simply begging my wife and her lover to release me from chastity, but rather begging merely for the opportunity to ritualistically grovel for such release. They had agreed to my plea — my petition was set for 8 PM that evening in the sitting room — a fact that in itself meant I was already facing a day of above average humiliation, even before Daphne paid a surprise (to me, at least) visit to the mansion with her friends. While the timing was a surprise, however, the visit itself I quite expected; Daphne had made no secret of wanting to show off her “hot,” ripped cousin to her girlfriends.
Since Lorena had left for Brazil the prior day for an extended visit with her family, Ryan and I were alone together in the mansion that afternoon when Daphne and her friends rang the doorbell. Her friends had never been to the mansion before, so I’m sure that was another part of the appeal of the visit for them. Imagine things from their perspective: an opportunity to meet this fabulously wealthy, “Greek god” of an eligible bachelor and to be waited on by his feminized maid — Daphne’s uncle, the bachelor’s own father, the once powerful, once arrogant hedge fund executive who was so perverted that he willingly surrendered all of his wealth, power and dignity to become a modern day slave. They probably had not been so excited to visit someplace since they went to Disneyland as young girls. Except this was not a fantasyland; this was all too real.
That afternoon was the first time that I had been alone with Ryan since his return, so there was actually a part of me that was relieved when Daphne and her posse showed up — as humiliating as I knew their visit would be for me. Under the influence of Natalie and Piper, Ryan was growing increasingly comfortable — by the minute it seemed — ordering me around as his domestic drudge and disciplining me. He has started insisting that I clean his en suite bathroom on a daily basis (and given his tendency to splatter urine on the rim of the toilet and on the surrounding floor, this was not a superfluous task). The day before yesterday, in fact, I cleaned his bathroom as he and Piper sat on his bed in the adjoining room, making out with one another. When, riding crop in hand, he came into the bathroom to inspect my work (as he often does), he found one of my long hairs on the tiled floor of his walk-in shower. It obviously had escaped my attention when I did my usual once over before his inspection (to be honest, my stockings were wet with urine from where I had knelt while scrubbing the bottom of the toilet and I was mainly focused on showering and changing into a fresh pair of stockings as quickly as possible). He immediately began berating me, causing Piper to pop her head into the room; she did so just in time to see him bring his riding crop down sharply on my panty-clad bottom as I was back on my knees to remove the hair and reapply the sponge to the part of the shower where it had lain. As he struck me a second and third time, Piper laughed and kissed him before pulling him back into the bedroom and onto the bed.
That day, as was usually the case when I cleaned, I was wearing my blue working maid’s uniform with flesh colored stockings (it was a requirement of Natalie’s that I always be dressed in pantyhose or stockings, generally black, white or nude, when performing my maid duties — or, in other words, pretty much anytime when I was not sleeping). Therefore, it should’ve tipped me off on the day of Daphne’s visit with her friends when Ryan ordered me to change from my working uniform into my second shortest serving uniform (“you know, the short one Mom likes, the one that sticks out on the sides”) after I finished cleaning his bathroom that morning. The uniform in question did indeed flare out absurdly at the sides, almost like a parody of a maid’s uniform but for the very fine quality of the fabric (Lou and Gina really outdid themselves in designing and making this one, with maximum humiliation of its wearer clearly top of mind). With it, naturally, I wore seamed black stockings and three inch high heels. I thought it was possible, of course, that Ryan simply wanted me to be dressed more formally to serve him lunch or tea in the afternoon. It only became obvious to me in retrospect that he wanted me to dress more formally to receive visitors. Daphne had no doubt selected a day when Natalie, Mason and, most importantly, Piper would be absent so that görükle escort her friends would get a chance to spend time with Ryan without competition for his attention.
Ryan and Daphne had already given the three visitors a tour of the mansion when I stood before them gratuitously curtsying for their amusement. They were all seated comfortably on the couch and recliners in the living room, enjoying the tea and sandwiches I had just served them. Ryan was dressed in a a pair of tight jeans and a snug fitting T-shirt, his large biceps clearly visible below (and through) the short sleeves. His brown leather ankle boots still sparkled in the afternoon sunlight from the polishing I had given them two days earlier. Riley and Leah were seated on each side of him on the couch while Daphne and Bella rested on the recliners.
“When does the maid do a deep curtsy instead of a regular curtsy?” Leah asked Ryan.
“Usually when he needs to show extra respect for someone, like when he greeted me when I came home from boarding school, or when he’s in trouble and trying to wiggle his way out of punishment,” he replied.
“Awesome! Make him do another deep curtsy again, please, Ryan,” said Riley, snickering.
“You heard the young lady, maid. Deep curtsy to each of us, individually. Start with Miss Riley, go clockwise and finish with me,” Ryan commanded me.
“Yes, sir,” I replied.
Natalie’s requirements for a deep curtsy are that I bend my knees and lower my torso down 9 to 10 inches and maintain that position for 4 to 5 seconds, holding my skirt out and bowing my head down. Even though I was now more physically fit than I probably have ever been in my life, doing several such deep curtsies in succession is not an easy task; If you don’t believe me, try it for yourself. By the time I completed the circle and curtsied to my son again, I was teetering on my heels, feeling a burning pain in my calves and thighs, and almost toppled over.
“Oh my, he really didn’t do the last one very well,” said Leah. “Is your father — um, I mean your maid — punished when he fucks up like this?” Leah asked.
Ryan pulled out of his pocket a pen and the small notebook where he had recently started logging my “demerits,” as he calls them (he used something similar to record the failings of the junior boys while a prefect at his boarding school), and said, “I keep track of the maid’s demerits here and, yes, he is punished.”
“By you, I hope,” Riley said, giggling.
“Sometimes, yes,” Ryan answered with a smile.
“I notice you call the maid he rather than she,” said Riley.
“Yes, he’s obviously not a female, although my mom and Mason sometimes refer to him as she. I think it’s an insult to you lovely ladies to call this joke a she. The way I look at it is that even though he’s a total disgrace to his gender, he’s still a biological male and should never be allowed to forget that,” Ryan responded. “He’s a pathetic fucking pantywaist.” My cock throbbed against the cold metal of my MAMBA chastity cage at this incredible humiliation.
“That’s right. Daphne told us that he begged your mom to be her and her lover’s maid. I guess he gets off on this, right?” said Bella.
“He’s one of those sissy cuckolds. I was reading up on them yesterday,” interjected Leah.
“Disgusting, isn’t it?” sneered Ryan, in more of a statement of fact than a question.
“It is pretty pervy, no doubt. But in my AP Psychology class we studied sexual repression. Maybe he was sexually repressed the whole time he was living the life of a hedge fund hotshot, and this is the real him,” said Leah, the apparent scholar of the group, looking me up and down.
“Maybe. But I don’t really care about his motivations,” said Ryan.
“It’s just so cool that your father is your little maid,” said Riley. “I love it!”
“But how does that make you feel, Ryan? I mean, aren’t you uncomfortable seeing the man you looked up to as a kid reduced to…to this?” asked Bella, indicating me with her hand as stared at me with derision.
“I’m not uncomfortable with it in the least. I never looked up to him. He was never a father to me. I never thought of him as a real man. Any so called man who allows himself to be put into this position deserves everything he gets, and more. Trust me when I tell you that he makes a far better maid than he ever did a father.”
“Remember, Bella, that Daphne said maid Henrietta treated Ryan like shit when he was growing up. And his mom, too,” said Riley.
“Right. So maybe he begged to become the family maid not only to deal with his repressed sexuality, but to deal with his repressed guilt, too. It’s a way for him to live out his perverse sexual fantasies while also making things up to you and your mom for being such a complete asshole for all those years. Sort of killing two birds with one pervy stone,” said Leah to Ryan. I wonder what grade she received in AP Psychology. Dime store psychology is more like it. She should’ve stuck to biology.
“Like I said, I really don’t give a shit about his motivations,” said Ryan dismissively.
“You shouldn’t, Ryan,” said Daphne, who obviously knew the real story, who knew that me standing before them as a sissy maid was about as voluntary as a bank teller handing over all the money in his drawer to the man holding a pistol against his head. “Aunt Natalie could have kicked him to the curb, but she and Mason are nice enough to let Uncle Henry live out his sick fantasies in this beautiful house. But no one asked Ryan what he thought about that. It was sprung on him as a surprise when he came home the day before Thanksgiving.”
“I’m okay with it, Daph. Really. It was a bit of a surprise at first, but the more I think about it, it makes perfect sense. Besides, there are worse things than having a 24/7 maid to wait on you and clean up after you.”
“I’ll bet! I wish I had one. The way I see it is Ryan not only gets a maid but lots of opportunities for well deserved revenge on his prick of an old man. His old maid, I mean. Ha ha. You’re the man, Ryan!” said Riley, shamelessly. She was the worst (and the sexiest) of the bunch. If anyone could give Piper a run for her money in seducing Ryan (and tormenting me), it was this long legged vixen. Although, the sultry (if now temporarily absent) Lorena was still a contender, I suppose.
“I want my own maid. I’m going to make Phil Evers wear a maid’s uniform the next time he comes over,” said Leah.
Ryan laughed. “Who’s Phil Evers?”
Bella answered for Leah. “Phil is this pathetic little dweeb who has it BAD for Leah. She friendzoned him after their first date and now Phil is Leah’s little errand bitchboy. He even cleans her parent’s house for her.”
“So a maid’s uniform is appropriate,” said Leah.
“Ha ha. Imagine your mom’s and dad’s reaction to seeing Danny dressed as a maid!” Bella said, tittering.
“They wouldn’t care. They love having free maid service. They’d think it’s funny. I’m serious. I’m going to order him a maid’s uniform on Amazon,” said Leah. Turning to Ryan, she said, “You can buy anything on Amazon these days.”
Daphne said, “Yes, but the ones you’ll find on Amazon will be cheap. Aunt Natalie has Uncle Henry’s — I mean Henrietta’s — uniforms custom made by a tailor.”
“Hey, you have to start somewhere,” said Leah.
“Phil will look terrible in a maid’s uniform. Ryan’s dad has much better legs,” said Riley, laughing. Everyone stared at my legs, critically. I wished it was possible to disappear into thin air.
“I’ve started making Phil go to the gym twice a week. Meanwhile, I’ll buy him a longer uniform,” Leah said.
“Phil is a creepy, little gooner,” said Riley.
“You’re just jealous, Rye. I think he’s kind of cute, in his own pathetic way,” answered Leah.
“You just like his big puppy dog eyes. Instead of a maid’s uniform, you should buy him a pink collar and a leash,” said Riley.
“Ha ha. Good idea! I’ll buy those for him, too,” Leah replied. They all had a good laugh. Poor Phil, I thought to myself.
Bella said to Ryan, “I understand your maid likes feet and is pretty good at cleaning shoes. I wasn’t able to make it the night at Daphne’s before Thanksgiving when he cleaned several pairs of Leah’s and Riley’s shoes. I have a massive shoe collection, but I chose these boots to wear today because they’re pretty scuffed up and could use a good shine. Could I borrow him for a few minutes, Ryan?”
“No problem. Fetch your shoeshine kit, maid, and make Miss Bella’s boots look like new,” Ryan ordered me, sharply.
“Yes, sir. Right away, sir,” I said with a curtsy. I heard the girls laughing as I hurriedly left the room to retrieve the kit.
The girls continued to enthusiastically flirt with Ryan as I knelt before the smirking Bella and polished and buffed her boots. They asked him about life in the UK, his college plans and his bodybuilding. He ate up the attention like gourmet ice cream, flirting effortlessly with them in return (something I was never capable of).
When I finally finished buffing, Bella examined her boots critically and said, “They look a little better than before, I guess, but I’ve certainly had way better shoe shines.”
Ryan responded by pulling the little notebook out again and making another mark in it.
“Uh oh, looks like another demerit to me,” said Leah, winking at me maliciously.
“I certainly hope so,” said Riley.
“I understand your maid also does foot massages. Maybe he could make up for his subpar shoe shine by massaging my feet. They’re a bit sweaty, though,” said Bella.
“You heard the beautiful young lady, maid. Remove her boots and massage her feet. Make sure that you do a better job on them than you did on her boots or you won’t be able to sit down until the new year.”
“Yes, sir,” I replied.
Riley laughed. “Don’t do too good a job now, Henrietta.”
As I pulled off Bella’s tight fitting boots, requiring some real effort, Daphne said, “But now we all have to smell Bella’s stinky, sweaty feet.”
“The worst,” said Riley, with a snicker, waving her hand as if to blow the odor away.
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