Lawyer2Maid Ch. 02

Story Info
Brutal cuckolding of arrogant lawyer turned maid.
18.7k words
4.04
7.5k
3

Part 2 of the 3 part series

Updated 05/26/2024
Created 05/07/2024
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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.

The garden party got universally rave reviews. This, of course, caused me great anxiety that Lauren and Jason would plan future such events, possibly including an even larger subset of my former social circle.

In the weeks following the party, I was kept busy fulfilling my obligations to each of the guests based on their service voucher selections. Jason and Lauren provided each guest with a card to rate the quality of my service on a scale from one to 10. Any score below seven would require me to repeat the service. Any score below five would require me to repeat the service as well as submit to punishment by Jason. The recipients of the subpar service would be invited to witness my correction.

All but one of the young female (and one of the young male) members of my old firm punched the hole for housekeeping services. I drove to their homes in my 2003 Subaru, the very one that I had forced Amanda to drive after she sideswiped my Porsche when she was 17. Amanda now drives by former late model Porsche at college. The Subaru has 143,000 miles on it but still gets me around. I dressed in short cut offs and an old T-shirt, carrying one of my working maid uniforms in my duffel bag along with cleaning supplies. These resemble hotel maids' uniforms: blue or gray cotton dresses, with white collars and aprons, worn with flesh toned stockings. When cleaning the mansion, unless being punished, I was permitted to wear flats (Lauren had even recently started to allow me to wear kneepads when scrubbing the floors and bathrooms, as I have knee problems). However, I was required to wear heels when cleaning the homes of the party guests.

I discovered that my former young subordinates were more than happy to take advantage of my powerless situation. Most required me to provide at least one of the other services on the punchcard in addition to what they selected. Penny and Alyson, for example, demanded that I pause my cleaning to massage their feet. One of the young male attorneys had me wash and vacuum his SUV after I cleaned his house (at least I was able to change back into my cut offs and T-shirt as I worked in his driveway). Samantha insisted I clean her bathroom after polishing and organizing her extensive footwear collection. In addition, despite my diligent efforts, all but two of my former employees gave me service ratings of below seven and two gave me below five. The latter included Penny, of course. It was clear to me that she had a sadistic streak and truly got off on seeing me punished by Jason or others. I suppose that they all made the calculation, quite correct, that I was in no position to raise any objections about the added services or unfair ratings. I didn't even try.

For those who selected caddy service (Joe, Forrest, the young, gay male junior partner), I was required to wear my British schoolboy uniform while caddying at my old country club or at a public golf course. As ball boy, if the match was played at my old club or on a public court, I wore a navy blue shirt and shorts similar to the uniform of a Wimbledon ball boy -- humiliating for a 61-year-old, but not overly so. However, after talking with Jason and Amanda, two of the male junior associates opted to play mixed doubles on the secluded court at the mansion. Samantha and Alyson were their doubles partners. On this occasion, I was dressed simply in white tights and a white T-shirt, trying valiantly (but unsuccessfully) to hide my shameful erection as I retrieved balls and fetched towels for my young superiors.

The first day I caddied for Forrest at my old country club was particularly challenging. Forrest played in a foursome with Jason and two of my old clients, including one of those who abandoned me just before Forrest forced me out of the firm (he was able to retain the client as his own.)

When the client -- the general counsel of a large, privately held company -- saw me carrying the bags of my old rival at the firm in my ridiculous schoolboy attire (the stripes of a recent caning still visible on my upper thighs), he laughed and said to me, "I'm not sure what Johnson has on you, Jenkins, but it must be a doozy."

"Yes, sir," I replied, staring at the ground.

While the four gentleman had drinks at the clubhouse after finishing their round, Jason volunteered my services to the country club manager. When I was a member, I had complained to this individual a number of times (rudely, no doubt) about the filthy condition of the golf carts. Perhaps not surprisingly then, I was put under the direction of the high school kid who washed and charged the golf carts. He, of course, recognized me as the former member who got him in trouble and thoroughly enjoyed bossing me around.

"You didn't clean the tires and back of that Club Car well enough. Clean it again."

"Yes, sir, of course," I said, scrubbing the cart with a sponge in the hot sun as Forrest, Jason, and my old clients stared down at me from the hill, where they were sipping their cold glasses of beer and laughing.

A less public, but far more humiliating event also involving Forrest occurred a week later when he and Jane took up my self-defeating suggestion to attend one of my punishment sessions with Jason for mistakes in proofreading Forrest's legal documents. Also in attendance, per her request, was Penny, along with Jason and Lauren, of course. Dressed in one of my formal serving uniforms, I greeted the guests when they arrived and served drinks and snacks. After I made sure they were comfortable in the sitting room, Penny requested that I microwave popcorn for what she described as "the coming show." She bought her current boss, Forrest, a rattan cane (in what I thought of as a real suck up move) and bought her old boss, me, a ridiculous pair of tights, one leg white and the other black.

After I thanked Penny for the thoughtful gift, Jason said, "Jenkins, go change into the new punishment tights Miss Penny has kindly given you and then report back to me. Make sure to bring your punishment lines with you. Chop chop."

Upon returning to the room in my ridiculous tights, I was compelled to kneel before Forrest and present the new cane to him with my palms upturned. After he took it, I handed him my punishment lines ("My incompetence and carelessness know no bounds. Please beat them out of me, sir." 500X).

Jane said, " Forrest, I know you were planning on helping Jason, but I'm sure he wouldn't mind if you handle all of Jenkins' punishment."

Jason replied, "Be my guest."

Forrest swooshed the cane a few times before resting it against my ass. He then delivered the first of 10 savage strokes. After the sixth one, I reflexively try to shield my bottom with my hands.

Jason said, "Jenkns, if you don't remove your hands, I will beat them next. And then your feet."

Having suffered bastinado for the first time recently after spilling Jason's glass of Pappy Van Winkle, I promptly removed my hands. After Forrest finished, I was ordered to assume my penance position, facing my tormentors. Jane and Penny had huge grins on their faces as they munched their popcorn. Jason smacked my cock and balls lightly with his cane until I grew hard my tights. After 30 minutes, I was permitted to put my serving uniform back on to begin preparing dinner.

The ramifications from the garden party continued for me into the fall and early winter.

The idea sparked at the party between Jason and Forrest for me to come into Manhattan two evenings a week to clean the offices of my old law firm came to be realized. The building management company was more than happy to save the expense using their outsourced cleaning staff on those nights. It was considered a bit too risky for me to wear one of my maid uniforms in a public office building. Instead, I wore tight, gray janitorial coveralls (like all of my non-maid attire, they were at least one size too small). To maintain the spirit of my emasculation, however, I was required to wear panties or tights underneath the coveralls. I was to report to Alyson when I arrived to receive my instructions for the evening; she inspected my work to make sure it was done satisfactorily and also checked to ensure that I was wearing my required undergarments.

Both the men's and women's restrooms were always filthy, urine all over the toilet seats and floors, wet toilet paper strewn about, etc. I never recalled the men's restroom being in that condition when I worked at the firm. It caused me to wonder if everyone went out of their way to be particularly careless on the evenings they knew I would be working. Me showing up at the office to perform janitorial duties was the first time my reduced status was exposed to a broader group of my former colleagues. Lawyers and their staff often put in long hours, so it was not unusual for there to be 10 or more lawyers and paralegals working while I cleaned around them. Most knew of my humiliating proofreading responsibilities. But seeing me demoted to janitor, unpaid no less, took the humiliation to another level. On the evenings, I cleaned that Forrest worked late, he would demand that I carefully dust his Yale JD diploma hanging on the wall of my former corner office.

Any complaints about the quality of my cleaning were ultimately funneled to Jason. I'm sure no one had any doubt about the consequences for me.

Amanda and Ryan spent their Thanksgiving break at the mansion. During this time, Lauren and Amanda began planning their respective weddings. With my lack of any opposition to Lauren's desired terms of our divorce, it was on a fast track and scheduled to be finalized by February.

The Wednesday before Thanksgiving, Lauren, Jason, Amanda, and Ryan were in the mansion's home theater, watching the movie, Tar -- a film about another powerful, arrogant person humbled and publicly humiliated -- as I served them popcorn and drinks, dressed one of my formal serving uniforms. I was ordered by Amanda to fetch her friend Mia's gift to me from the party, the pedicure kit, and to give the four of them a pedicure as they enjoyed the film. For the last several months, Lauren had forced me to get pedicures at one of the nail salons in East Hampton Village (my toes were now a light shade of blue). She had recently paid one of the pretty young Asian girls at the salon to give me lessons on how to give a proper pedicure.

After the four that were comfortably seated in the theater chairs, I knelt before Lauren, whose feet were elevated on a short stool, and began the steps I had learned. I removed her old nail polish, trimmed her nails, and then massaged her feet within their foot bath. After drying her foot, I scrubbed it with a pumice stone and foot file, before placing cotton swabs between her toes, and then applying a new coat of orange polish. After finishing both of Lauren's feet, I then repeated all of the same steps with Amanda, trying surreptitiously to listen to Cate Blanchett's magnificent performance as I worked.

Amanda, sipping her glass of red wine, wiggled her freshly painted toes in front of my face, and said, "Blow them dry, father."

"Yes, Miss Amanda," I replied, doing as she bid. She looked down at me, smirking

and barely able to suppress her giggles.

After Amanda was satisfied with my efforts, I moved on to the more distasteful task of working on Jason's dry and calloused feet. I had to press hard with the pumice stone on his soles in an effort to remove the callouses and feared that I might be annoying him. I massaged his feet and legs rigorously, in the hopes of discouraging him from finding any pretext to punish me. After carefully removing his cuticles, I applied a coat of clear nail polish to his toes, as I had been taught.

After I finished with Jason, Amanda said, "Okay, father it's now time for you to do MY man's feet," and giggled. It was clear to me that she was getting a bit tipsy.

"Of course, Miss Amanda." I moved my stool and a clean foot bath over to Ryan and said, "May I remove your socks, Master Ryan?"

"You can't very well give me a pedicure with them on, can you now, maid? Or what was it that Mia called you? Foot girl? You may remove my socks, foot girl," he said, smirking. Amanda laughed heartily.

Jason usually called me Jenkins. Lauren typically called me Gregory. Amanda most often called me father. Ryan, on the other hand, when he addressed me by name at all, did so in whatever demeaning manner suited his mood at the time: maid, boy, old man, or whatever occurred to him at the moment.

Ryan's feet were much softer than Jason's, fortunately. I gave him the same treatment, including the same rigorous massage I had given to the others. After I applied the clear polish to his feet, he said, "Foot girl, blow my toes dry like you did Amanda's."

"Yes, sir, of course." I felt the shame course through my body, directly to my hard cock, as I did as he commanded, with the others looking on.

Ryan reprimanded me, "Foot girl seems to be more focused on the movie than on his task."

Lauren said, "Of course, he is. He recognizes himself in the protagonist."

Amanda giggled. "I'd be careful if I were you, maiddad, you wouldn't want to get six of the best again from my strong fiancé, would you?," she said, squeezing Ryan's bicep. She leaned over and kissed him.

"No, Miss Amanda," I said.

"Then you better damn well better pay attention to what you're doing," said Ryan coldly.

"Yes, sir. My sincere apologies for my lack of focus. It will not happen again.

When the movie was over, having mercifully escaped punishment, I was excused to go brine the turkey for tomorrow's feast.

I was up very early the next morning to begin peeling potatoes, washing vegetables, chopping garlic, etc., dressed in my working maid uniform. The family had graciously decided to go out for breakfast so that I could focus completely on my responsibilities. The one exception was that Ryan summoned me to polish his shoes before they left for breakfast. I was in the middle of stuffing the turkey, so I had to carefully wash my hands before going to his and Amanda's bedroom with my shoeshine kit. He was sitting on a loveseat in the room and pointed down to the black loafers on his feet. I usually polished footwear when they were not being worn, but Ryan seemed to take special delight in forcing me to kneel before him to shine his shoes while he was wearing them. I felt his freshly pedicured toes move around through the leather as I buffed.

Not wanting to be outdone, I suppose, Amanda said to me, "While you're down there, you might as well polish my boots as well, father." She sat down next to Ryan and unabashedly made out with him as I polished and buffed her brown leather ankle boots to her satisfaction.

This was my first Thanksgiving since transitioning from man of the house to maid of the house, and I was anxious about meeting the clear expectations for the meal (and the whole day) set for me by Lauren and Jason. Fortunately, Lauren had engaged the woman who trained me in maid deportment to instruct me in how to prepare a multi-course Thanksgiving dinner for multiple guests. It was also fortunate that my sister, Susan, and my niece, Olivia, were willing to assist me with some of the meal preparation, even though they were also guests.

Besides my (soon to be ex) wife, my daughter, Jason and Ryan, of course, the guest list included Susan, Olivia, and the family of Lauren's younger sister, Nicole (age 39) -- specifically her husband, Bill (age 42), and their two teenage children, Ethan and Isabella, twins who had recently turned 18. They were driving in from Richmond on Thanksgiving morning. While Nicole and Bill had certainly heard about the significant changes in our household, they had not visited in the prior nine months. They were in for an interesting experience. I had no idea what they had shared with their two children, but I dreaded all of them seeing me in my greatly diminished position.

Lauren and Nicole were close. Although college educated, Nicole married Bill, who made a decent, but squarely middle-class, living as a construction supervisor. In my prior life, I always felt superior to Bill and Nicole and didn't try to hide it. They had not visited since the previous summer when Nicole and the two kids came out for what was supposed to be an extended stay at the mansion. It was cut short abruptly, however, after I lost my temper with Ethan and Isabella due to their near constant loud and rambunctious behavior. They were always running around screaming and leaving behind messes in their week.

One afternoon, unable to concentrate on a novel I was reading, I yelled at Ethan, "Would you please shut the fuck up, you insufferable brat!" Taking offense, Nicole and the kids left for Richmond the following morning, and had not been back since. Lauren didn't speak to me for nearly a week afterwards.

When they arrived around 2 PM on Thanksgiving day, I paused my dinner preparations to open the door and welcome them, still attired in my working maid's uniform.

"Welcome, ma'am, and, sir, Master Ethan, Miss Isabella," I said, curtsying deeply. "Please come in."

Bill and Nicole exchanged amused glances, and Ethan and Isabella looked at me with disbelief.

Nicole said to her two kids, "I have a feeling that this is going to be a much better visit than last time."

Both Ethan and Isabella had astonished smiles on their faces and grinned at me wickedly.

"Please sit down in the living room. I will bring in your bags from the car and then serve you all a refreshment," I said, curtsying again.

I retrieved their suitcases from Bill's four-door Dodge Ram pick up truck and brought them into their respective rooms. I then served the new arrivals drinks as Lauren introduced them to Jason, before returning to the kitchen to finish preparing the meal.

I had hand written the table place cards and, when it was time to eat, as previously instructed, I escorted everyone to their seats, starting with Lauren and Jason. As the others stood by looking on, I conspicuously pulled out Jason's chair at the head of the table -- the seat I had occupied at all past Thanksgivings and other family dinners -- curtsying to him once he was seated. During dinner, I obviously didn't eat with the guests. I stood at attention next to the table, wearing one of my most formal uniforms, stocking-clad legs pressed together, seams straight, arms at my side -- ready to fill anyone's drink, or refold anyone's linen napkin, if they got up for any reason.

Ethan asked Lauren, "What do we call him, or her, Aunt Lauren? It seems strange to call him Uncle Greg dressed the way he is."

Lauren answered, "Call him whatever you like, dear. In a few months, he no longer technically will be your uncle through marriage. Gregory is the maid here now, aren't you Gregory?"

"Yes, mistress," I curtsied.

Isabella giggled. "Maid, get me another glass of cider."

"Right away, Miss Isabella," I replied, curtsying, as I scampered off to the kitchen to fulfill her request.

As was typically the case, I was to dine on leftovers later by myself in the kitchen. Except for a few comments that the turkey was too dry, the meal generally seemed to be relatively well received. I was looking forward to being able to deviate from my normally strict diet to try some of the dishes I had prepared. After the meal, while a few of the family members took a walk and others watched football, I took advantage of the brief break to lay down on the cot in my room for a few minutes with my heels off. The door of my room was closed, but Jason had long since removed the lock; privacy was not a privilege of the domestic help. Characteristically, I had been aroused throughout the day, more so with each new indignity I suffered, but had not been granted any relief in over two weeks. Confident that everyone was occupied, at least for the next 15 to 30 minutes, I began to rub myself under my dress as I laid down on the cot. Suddenly the door opened and Ethan burst in, looking down at me on the bed. I quickly moved my hand away but, being an 18-year old male, I'm sure Ethan had no question in his mind about what I was up to (in truth, I wasn't planning to risk ejaculating in my uniform, but I did feel an irrepressible need to at least touch myself).