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Note: All characters are at least 18 years old. If a story about an arrogant, highly successful lawyer experiencing a brutal social downgrade — including being cuckolded and emasculated and becoming a sissified maid to his own family and former colleagues — is not your cup of tea, please read no further. If you are incapable of suspending your disbelief and/or feel the need to constantly project what YOU would do in similar circumstances to what the protagonist is experiencing, please read no further. Otherwise, please enjoy! Constructive feedback is always appreciated.

“Mom, I’m curious. Why don’t you ever punish dad?, asked my daughter, Amanda, of my wife, Lauren.

“Oh, honey, I give him a few strokes of the cane now and again, but it’s just so much more efficient to have Jason do it. He hits much harder.” The two of them grinned at each other.

Amanda replied, “I think the real reason is that you simply enjoy watching Jason administer the punishment,” Amanda laughed.

“I must confess, there is something titillating about watching a virile, muscular, young man, physically dominate an older, weaker man, especially a pathetic specimen like your father.”

“I can’t argue with you there, Mom. Especially when it’s so well deserved. There is just something so…so primal about it, isn’t there?”

“No question for me. But is it uncomfortable for you to see your father treated this way?”

Amanda said icily, “Not in the least. He may have impregnated you, but he has never been a father to me. He was always so focused on his stupid job, he never had any time for me. And he was a bastard. Remember on my 12th birthday party when I broke that Chihuly vase and he pulled down my skirt and panties and spanked me right in front of my best friend, Mia, and that boy I had such a crush on? I will never forgive him for that.”

“I remember, honey. It was dreadful.”

“And then when I was 17 and scratched his precious Porsche, he made me drive an old Subaru when all of my friends were driving nice cars. It was humiliating.”

“I know, sweetheart. I tried to talk him out of it, but you know how stubborn he is — or was, I should say.”

“Well, at least he has lost some weight. The diet and Jason’s exercise regime appear to be working.”

“They better be,” said my wife. “There’s nothing more unattractive than a fat maid. I’m still thinking of making him wear a corset. I will say that his legs have gotten firmer. He actually doesn’t look too bad in his stockings.” They both snickered.

At that moment, I was in one of the sitting rooms of what until recently was my palatial mansion in East Hampton, draped across the knees of Jason Collins, my former law firm junior associate, and Lauren’s lover. Jason is 29 years old. My name is Gregory Jenkins, and I am 61 years old. I took early retirement as the managing partner of our law firm a few months ago, not under the circumstances I had envisioned. As you can tell, also in attendance on that afternoon was my wife, Lauren, age 40 and my daughter, Amanda, who had recently turned 21 and was home for spring break during her junior year at Dartmouth. To paint the picture more fully, Lauren somewhat resembles the actress, Aubrey Plaza, and my daughter looks not unlike slightly younger version of Anya Taylor-Joy, in other words, both knockouts. Jason, or master, as he is now known to me, looks like a slightly more ripped version of the actor Theo James. As for me, I was about 5′ 9″ tall and still had thick hair, though almost entirely gray when not died. I was still somewhat flabby with a bit of a paunch, but Jason’s efforts were starting to have their desired effect.

The two women were dressed elegantly in short skirts, stockings, and heels, accentuating their long, lovely legs. Jason was dressed more casually in tight fitting jeans and a tank top. As for me, I was wearing nothing save for a pair of nearly sheer black pantyhose and a pair of nipple clamps, hanging down off my chest from my position on Jason’s lap. I was being punished for having served my wife and daughter two vodka martinis, when Amanda had in fact ordered a gin martini. In addition, when informed of my error, I carelessly spilled the rejected drink all over my maid’s uniform, which I was instructed to promptly remove.

As the managing partner of a prominent, boutique litigation firm in Manhattan, I had been used to being the oldest person in the room. However, in my profession–where I had achieved something of a celebrity status as a ruthless litigator and tyrannical boss–I was generally in control of the room. Quite a contrast to the situation in which I now found myself.

“Amanda,” said Jason, “since you are the offended party, it’s for you to decide how many strokes of the strap your father here shall receive.”

“Please, Miss Amanda, I am truly sorry.”

“Well, you will have to learn to be more careful. Twenty should suffice, Jason.”

Hearing this number, and familiar with Jason’s technique, I groaned and squirmed on his lap.

“Stay still, Jenkins,” he said, grabbing my balls firmly through my pantyhose.

“Yes, sir” I hurriedly replied. şerifali escort Jason began vigorously administering my correction, much to the delight of his audience. I was in tremendous pain by the 10th stroke but, tears in my eyes, knew better than to complain. Upon completion, Jason pushed me roughly onto the floor.

“Oh, look Mom, we can see his red ass through his pantyhose. I guess they don’t offer much protection.”

Jason said, “Jenkins, now get the ladies their correct drinks and a scotch for me. Do you need for me to write it down for you so you can get it right this time, you dimwit?”

I couldn’t help but resent this questioning of my intelligence. I graduated second in my class at Harvard Law and scored a perfect 180 on my LSAT. Jason, in contrast, was 9th in his class at NYU, with only a score of 169 on his LSAT. Frankly, he was a borderline hire. Nevertheless, I had to admit that, over the last six months, he had outmaneuvered me in the most consequential of ways.

Upon returning with the drinks, I was instructed by Master Jason to stand in the corner with my hands behind my head, and my legs spread wide. Looking down at my wife’s shoe dangling from her nylon clad foot, I soon felt myself getting hard despite my best efforts to quell it.

Amanda giggled and pointed, saying, “Ew, look, daddy has a stiffy.”

Hearing these words, my cock twitched still higher, growing the tent in my hose.

Lauren said, “No one wants to see that, Gregory. Turn away from us, and stand in the corner.”

Jason resumed control of the situation, roughly pushing me into the corner, and ripping off my nipple clamps as he did so. This resulted in searing pain in both of my nipples.

“Jenkins, nose to corner, hands behind your head. Stand on your tippy toes.”

I could last about 90 seconds on my toes before my 61-year-old calf muscles started trembling in pain. Every time my heels touched the ground, Jason struck my ass savagely with the strap.

He said, “This is ironic, Jenkins. When you ran the firm, you would berate me publicly if a single syllable in a deposition summary was misplaced. You routinely had me and the other junior associates work 15 hour days, even when it was unnecessary. You’d verbally humiliate the paralegals if there was a single word misspelled in 100-page document. You always said you were keeping us on our toes. Well, now, I’m literally keeping you on your toes, aren’t I?”

“Indeed, you are, sir,” I answered.

During this 30 minutes of torture, I reflected on how I had come to this place. It is important to understand that I definitely was not one of the typical passive beta males who end up as submissive cuckolds. I have always been in an unambiguous Type A personality, an overachiever, headstrong, determined to vanquish any competition to get ahead. I was a textbook asshole, and proud of it. I was that guy who is habitually rude to waiters and waitresses, cashiers, country club staff — anyone in a less privileged position than I. But I was rude to the more privileged as well, believing I was genuinely superior to just about everyone. I guess I was a little under endowed in the cock department, and perhaps therefore felt the need to overcompensate in other areas — drive the most expensive car, have the biggest house, have the prettiest woman on my arm. I became the managing partner of my 30-partner firm not because I was respected or well liked, but rather because I was the biggest biller and threatened to leave if I didn’t get the top job. Machiavelli like, I neutralized my one serious rival, Forrest Johnson, by undermining his relationship with a key client through innuendo. I had even earned the public nickname, Gregory “the Viper” Jenkins, for my ruthlessness both in and outside the courtroom.

I was so focused on getting ahead in my career that I married and started a family relatively late in life. Lauren was only a kid when I married her. She was beautiful, but I paid scant attention to her aspirations and needs (beyond the purely material ones). We did play occasional games in the bedroom where I liked to reverse roles, and treat her like my imperious queen, kissing her feet, and so on. I really found this as a way to loosen up and relieve the stress I felt from being constantly in charge. Even on these sporadic occasions, I would top from below and would act like my usual prick self the moment I orgasmed. I was always distant with Amanda, paying more attention to her when she annoyed me than at any other time. Lauren had her when she was very young, and they have always been close, more like sisters in many ways.

It was this periodic indulgence of mine of playing the submissive that led to my downfall. One afternoon, Lauren toyed with my cock, cajoling me to wear a cheap maid’s uniform that she had bought at the Spirit Halloween store or someplace like that. I finally agreed to play along and put it on. It barely even fit me and I looked ridiculous in it. It was a far cry from the carefully tailored maid’s uniforms I wear today (Lauren and Jason make me use the seyhan escort same tailors I had used for years for my power suits), I spent the next couple of hours serving her drinks and dinner, scrubbing the kitchen floor on my knees under her direction, licking her high heels, etc. It was amusing for a while, but I had had about enough of such nonsense when suddenly I got the shock of my life when Jason Collins emerged from behind our pantry door.

“What the fuck?”, I shouted.

Lauren said, “Calm down, Gregory. Jason and I have been lovers for the last six months, and you are too clueless and self-absorbed to have even have noticed.”

Then Jason took over: “This has taken quite a bit of planning on our part, Jenkins. We have hidden cameras throughout the house. Let’s all take a look at the videos, shall we.”

Stunned, I sat down and watched Jason replay what were surprisingly high-quality videos of me playing the sissy maid in my ridiculous get up. It was all around an absurd situation.

“So, here’s the deal, Jenkins,” said Jason. “Tomorrow we will all go to my friend’s law office. He is an estate attorney, and all of the documents have already been drafted. You will nullify Lauren’s and your prenup and transfer ALL of your assets solely into her name. Amanda will be the heir to her estate, of course.”

“That is ridiculous,” I said. “Dream on,” although I certainly did not feel I was negotiating from a position of strength, attired as I was.

Jason said, “If you refuse, tomorrow, copies of these videos will be in the inbox of every member of the firm and all of your clients. I have taken precautions to ensure that the files will be sent anonymously so that nothing can be traced to Lauren or me. I’m sure Page 6 of The New York Post will also find the story irresistible. Remember when poor Marv Albert was fired for getting caught crossdressing and The Post’s headline was ‘Marv Gets Pink Slip?'”

“That was hilarious,” said Lauren. I had thought so too at the time, but wasn’t laughing now.

Jason said, “I can see the headline now: Gregory, ‘the Sissy Maid’ Jenkins. If you sign the documents, I will destroy the files.”

The upshot is that I was so mortified at the prospect of such extreme public humiliation — something that would strike at the very heart of my public persona and result in the immediate termination of my career — that I showed up the next day at Jason’s friends office, and signed the documents, which were duly notarized. This capitulation was the greatest mistake of my life (or was it?), and I have been paying the price for it every second since. It had not occurred to me that Jason was capable of being as ruthless as I. For he destroyed the original video files, but did not destroy the copies he had made. They had me. He had me. Then he set about to break me.

Much has transpired in the six months since then. Jason moved in to my former home in East Hampton, sharing the king size bed with Lauren in the master bedroom, and I now sleep on a cot in the maid’s quarters. At the age of 61, now penniless in my own right and entirely dependent on Lauren’s mercy for a roof over my head, I have limited, almost nonexistent, options. My performance at the firm faltered after all of this occurred, and I lost two high profile cases and lost my two biggest clients. Forrest Johnson saw his opportunity for revenge and began working to push me out of the firm; once I was no longer feared, I quickly lost all support, and was forced to retire. My colleagues and subordinates were openly gleeful about my demise. There was no retirement party. Hanging out there, of course, were the tapes. I had lost my job, but was not yet a public laughingstock. But Jason and Lauren have the power to change that at will. Using their leverage over me, I was compelled to begin my advanced studies in humility.

Being the goal-oriented individual I am, I like to think of it as a PhD in humility with Jason as my doctoral advisor. Since my dressing as a maid is what enabled Lauren’s and Jason’s successful blackmail, they decided I would become the household maid. I was fitted for uniforms, both for everyday cleaning duties and formal service occasions. Lauren enlisted my daughter Amanda’s assistance in carefully selecting my uniforms (styles, lengths, colors, as well as brands of stockings, height of heels, etc.) and establishing the very specific behavior and etiquette that was expected of me. They engaged a private tutor, an older woman who used to run an old school maid training academy, to teach me all of the proper service etiquette, including how and when to curtsy, how to address my superiors, how to serve a formal dinner, how to clean most efficiently, etc. I was put on a strict diet by Lauren and given a strict, not to mention intensely humiliating, exercise regime by Jason. He became my personal trainer. My training offered ample opportunities for Jason to greatly augment his video library documenting my emasculation, thus further cementing his control.

So, that’s how I came to be standing on my toes in the sitting room before my side escort wife and daughter, dancing to Jason’s tune. Following my 45 minutes of penance, I donned a fresh maid’s uniform and stockings, and began cleaning and polishing every inch of Lauren’s 12,000 square-foot home, careful to ensure that it would pass her or Amanda’s exacting inspection. Over the last few weeks, Jason has introduced a new task I am obligated to perform. He brings home reams of legal documents from the office for me to proofread. So, after hours of cleaning during the day, I now find myself regularly spending several hours in the evening proofreading — a mindless task that, nevertheless, requires intense concentration, as errors result in harsh punishment. Another example of irony that appeals to Jason’s sensibilities: the former managing partner, now relegated to the bottom of the law firm hierarchy, proofing for his former associate. So, as I rest my tired feet, I must exert my weary mind.

I have noticed a distinct shift in my psyche that has begun to take place. There remains a side of me that continues to feel superior to those around me, including Jason, and the dichotomy of being in a position subservient to everyone creates in me deep feelings of anxiety, resentment and shame (even occasional strings of resistance, although these are diminishing). At the same time, I am coming to appreciate that there is a certain symmetry and logic to it all. What goes up, must come down…the higher they rise, the harder they fall. Clichés exist because they are grounded in truth. My ascent was impressive, my descent spectacular. After being an incorrigible asshole all my life, my intensive humility training is showing me that I do possess some capacity for feeling empathy and guilt. Stripped of my dignity, I have begun to feel more acutely than ever before in my life. Is it possible that I need to genuinely suffer for my life to have any true meaning? Certainly, I have started to eroticize my subjugation. So, at the age of 61, I have less power than ever, but at the same time am more of a sexual being than ever as well. It is complicated.

I never recall having been attracted sexually to men in the past. Nor do I believe Jason is really attracted to men. But I do know that Jason is aroused by dominating another man in the presence of women. And I know that I am aroused by being dominated by another man in front of women, especially when those women are family members or former employees who once saw me in a position of authority. Especially when that man used to be subordinate to me, and is less than half my age. As Amanda put it, there’s something primal about it, I suppose.

The day after my chastisement in the sitting room, I was informed by Jason that what I dreaded the most is coming to pass: my new status is becoming increasingly public. A garden party at the mansion has been planned for the last week in August in which I will be defending my dissertation in humility before a select group of guests, made up of former colleagues and subordinates, friends, and family. Between now and then, the plan is for me to prepare for this event through a series of warm up events

The first such event occurred the following week. All attendees agreed to sign a nondisclosure agreement to protect against any potential reputational damage to my old firm; the reputational damage to me was the whole point, of course, but it would be limited for the time being. Invited were three highly attractive young women from my former office (I always screened out the unattractive ones): Samantha, a junior associate, 30 years old; Penny, a 22-year-old paralegal; and Alyson, an 18-year-old secretary. Samantha and Alyson are long legged brunettes whereas is Penny is a petite blonde with a mischievous smile. All three had been on the receiving end of my verbal abuse numerous times when I ran the firm.

After swimming in the pool, they sat on deck chairs in their bikinis, waiting for the show to begin. While they may have had some inkling of what to expect, I’m sure nothing could’ve prepared them for what came next.

Samantha, Penny and Alyson had front row seats to see Jason putting me through my paces as my personal trainer. Jason led me out of the house by collar and leash into the yard, about 8 feet away from our audience. All three young ladies gasped, covering their smiling mouths in shock. Jason was shirtless, wearing skin tight jodhpurs and riding boots, carrying a cane in one hand and a riding crop in the other. I wore footed gray tights, nearly sheer, and nothing else save for my collar. Jason began our routine in the usual way, swooshing his crop three times in the air before striking my bare back to spur me on. He held the cane up to my waist, thus settling the required level of my high steps, as I began to trot in a circle around him. When my knees fell short, he would slash my ass with the crop, eliciting a yelp from me. Jason favors a split tip crop called the Motivator, known for the loud noise it makes when it meets flesh and the sharpness of its sting; it is aptly named. Next, he pointed to the ground, and I dropped to do push-ups, something I was never particularly good at, even when I was his age. Jason tapped the cane on my ass with modest force each time I raised it. This was followed by deep knee bends and jumping jacks, all with the encouragement of his crop or cane. It was over 90°, so it didn’t take long before Jason’s muscular torso was glistening in a sheen of sweat.

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