Lawyer2Maid Ch. 04

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 morally judge what is intended to be sexual fantasy, please read no further. Otherwise, please enjoy! Constructive feedback is always appreciated.

Following Labor Day weekend, the parties didn't cease, but were less frequent and smaller in size. Ryan was able to secure an entry-level position with a hedge fund in Manhattan. After much discussion, Lauren and Jason decided to purchase Amanda and Ryan a 3000 square-foot "starter home" in Southampton for $3 million (the $25 million I had managed to amass in my brokerage account before my forced retirement had increased to $28 million with the strong stock market, so this was well within their means).

It was determined that I would split my time between Lauren's and Jason's mansion and Amanda's in Ryan's new home nearby. So, going forward, I would be responsible for cleaning not one, but two homes. I was hopeful that I would eventually get some sort of reprieve with respect to my proofreading duties, or the biweekly cleanings of my old firm's offices in the city -- or, at the very least, the semi-regular cleanings of Forrest's and Jane's home.

Meanwhile, Shyla's parents purchased her a 6000 square-foot home in Sagaponack and a 3000 square-foot condo on the Upper East Side of Manhattan. Rebecca was going to be exceedingly busy as well. I overheard Ryan tell Amanda that Shayla also planned on sending her up to Rhode Island once a month to do a deep cleaning of her old sorority house under the direction of Julie, who had succeeded Shyla as sorority president.

Jason's amping up of my humiliation began gradually before later events caused it to accelerate like a rocket ship. After hearing from Amanda and Ryan about the dungeon in the basement of Shyla's parents' home, Jason began converting an old storage room in the basement of the mansion into a dungeon. He mounted an X-shaped St. Andrews Cross to the wall with leather wrist and ankle cuffs. He purchased a leather spanking bench. He also attached a bar with cuffs and a pulley to the ceiling similar to the one used by Shyla when she whipped Rebecca; the pulley allows the flagellant to twist and turn a full 360°. Jason hung up the whip rack that I had bought him the prior Christmas next to the St. Andrews Cross, adding a second rack on which hung many new instruments of torture: cat o' nine tails, bull whip, floggers, straps, nipple clamps, leg irons, etc. I watched with a mixture of fascination and terror the accumulation of this paraphernalia, realizing all of it was intended for little old me.

Meanwhile, Lauren and Amanda began forcing me to wear my posture collar for at least an hour a day. I have noted how much I detest wearing even a buttoned dress shirt or choker around my neck; so, you can imagine how I felt about wearing a restrictive 4 inch leather collar that forced my chin upwards. I was compelled to wear this while serving drinks in my formal uniform. Because it was difficult to bend my head to see what I was holding or placing on a serving tray, I had to move with extreme care, so as not to spill anything (which, unquestionably, would result in punishment). Increasingly, I was forced to wear my posture collar together with my new lockable corset, either with my uniform or with thigh high stockings, garters and panties. Even though I had probably lost 50 pounds since my subjugation started, the corset took another 3 inches off my waist. Lauren or Amanda would lace me tightly for hours at a time. On one occasion, when I meekly protested that it was difficult for me to breathe, I was told in no uncertain terms by Lauren that I was being corset trained, and that my body would adjust over time. She encouraged me to suppress any future urges to protest by administering several sharp smacks to my bottom and balls with a wooden spoon.

Lauren and Jason planned a large Halloween party at the mansion. The guest list was to be pretty extensive, including most of the attendees of last year's garden party as well as Paolo, Shyla, Kyle and former college classmates of Amanda and Ryan. It won't surprise you to learn that service was to be provided by Rebecca, George and yours truly.

There were many outstanding costumes, including:

Lauren as Cleopatra and Jason as Mark Anthony

Amanda as Harley Quinn and Ryan as the Joker

Paulo as Jaba the Hutt with a chained Rebecca as enslaved Princess Leia (for which she had the perfect body)

Shyla as a sexy vamperiress

Samantha as Catwoman and her boyfriend as Batman

Forrest and Jane as a warlock and witch

But it was Penny and her entourage that made the biggest splash when they walked into the living room. It was not really her costume that impressed (she was wearing a little black dress with black stockings and heels, along with a carnival mask). Rather, it was the spectacle of the foursome of which she was a part that was startling. She walked walk arm in arm with a huge, chiseled, shirtless male (thighs like tree trunks, enormous biceps, a torso of pure muscle) -- another whole level of jacked than her pro wrestler boyfriend, Kyle. The contrast was easy enough to see because her new companion was leading Kyle, dressed solely in pink wrestling trunks and white boots, by black collar and leash. Kyle, in turn, was leading poor George (clad simply in sheer, pink footed tights) by pink collar and leash.

Lauren said, "Penny! You are incredible! You're going to steal the show."

Penny smiled shyly yet proudly. "I hope you don't mind that I invited another guest. This is Dustin. He's a UFC fighter. UFC means ultimate fighting champion. He was the heavyweight champion two years ago."

Amanda said, "But I thought Kyle was a heel and that only jobbers wear pink."

Penny replied, "Well, there are heels, and then there are heels. It turns out that pro wrestling is pretty much all fake. UFC fighting is the real thing. Dustin came up to me after Kyle beat up a jobber on Monday Night Raw. He saw me kissing Kyle after the match. When Kyle went backstage to change, Dustin asked me if I'd like to see someone--namely, him--dominate Kyle in the ring. I have to admit that, looking at him, I was intrigued. They agreed to a match, with me as the prize. It was no contest; Dustin absolutely DESTROYED Kyle. Kyle, Georgie and I moved in together a month ago. Normally, Kyle is the alpha male at home and Georgie is the maid. But that all changes on the nights that Dustin visits, doesn't it, Kyle?"

"Yes, ma'am," answered Kyle, sheepishly.

"Maybe we can give you a little demonstration later," said Penny.

"You are amazing Penny," said Amanda.

Rebecca, George and I served the guests all evening -- Rebecca in her Princess Leia slave girl costume, George in his pink tights and me in a custom made, orange and black satin maid's uniform with black seamed, sheer black stockings and 4 inch heels.

Later that night, after many guests had gone home, Kyle wrestled hapless George, quickly putting him in a submission and forcing him to kiss his foot to signify his defeat. Immediately thereafter, Dustin manhandled Kyle, toying with him for 15 minutes. Dustin finally pinned Kyle, with his balls pressed against Kyle's chin. After repeatedly slapping his face and making Kyle cry "uncle", Dustin stood over him in classic victory pose, one bare foot on Kyle's crotch and the other on his throat.

Afterwards, Amanda said, "Mom, it's Saturday night. With the party, we forgot father's maintenance spanking,"

Lauren replied, "No time like the present."

"Father, after you refresh everyone's drinks, go put on your new black and orange punishment tights and report back here."

"Yes, Miss Amanda." I curtsied deeply.

The Halloween party concluded with me across Jason's lap receiving 50 hard smacks with his bare hand on my bottom, followed by my classic penance position before the crowd, my cock shamefully at full mast.

Penny's foursome (or quartet, I'm not sure what to call it) remained the leading topic of conversation the next morning as I served Lauren and Jason breakfast. I had gotten up at 5 AM to begin cleaning up the mess from the party in my working maid's uniform, but had changed into a serving uniform for breakfast. Immediately afterwards, I would change back into my working uniform, eat my breakfast in the kitchen and then resume cleaning.

"That Penny is incorrigible," said Jason, with a smile.

"She's a force of nature," said Lauren. "I really love how she has embraced our lifestyle."

"I wonder if, at the next party, Georgie will have an even more submissive creature on a leash, and there will be five of them?"

"I think Penny would be hard-pressed to find a more submissive creature than Georgie," laughed Lauren. "Penny told me that she had originally thought of coming to the party with a Dr. Seuss theme, with Kyle as Cuck One and Georgie as Cuck Two. But she wanted the three of them to wrestle for us, so she thought she should stick to how they usually dress at her place. It probably would've been challenging to make the costumes anyhow. She also shared with me some of the more salacious details of what goes on when Dustin spends the night."

"Pray tell."

"Well, apparently, Georgie usually serves Dustin and Penny dinner in one of Gregory's hand me downs I gave her, while Kyle either washes Dustin's car in his pink trunks or does Dustin's laundry. Then they often watch a movie, during which Kyle and Georgie give Penny and Dustin foot massages. Sometimes Dustin has Kyle working on one of his feet and Georgie on the other while he and Penny make out. Then Penny gets to enjoy some submission wrestling and fighting on her behalf. Dustin always wins. Later, when they go to the bedroom, the preferred position is Dustin on top of Penny with Kyle underneath them, either licking Dustin's balls or his shaft as he goes in and out of her. At the same time, Georgie -- as befits his position at the bottom of the hierarchy -- is usually either sucking Kyle's toes or his cock. Obviously, they change things up a bit, but you get the general idea."

"Sounds complex, but fun for Penny -- and Dustin," said Jason.

"Penny said that when Dustin is not around and it's just her, Kyle and Georgie, the dynamics are more like what we have with Gregory."

"Well, I'm sorry to disappoint you, honey, but I have no intention of submitting to anyone, in case you were hoping to emulate Penny."

Lauren laughed. "I know you don't, darling. One of the things I love about you is that you're submissive to no one. I am quite content with our little ménage à trois as is."

Jason replied, "But keep in mind, you're going to have to share Gregory more and more with Amanda. In addition, he's not getting any younger. We may want to consider acquiring some new submissive at some point."

"What did you have in mind? Male or female?"

"I'm not really sure. It's just something to think about. Jenkins' health won't hold up forever."

"I'm not too concerned. With your exercise regimen, Gregory seems to be in the best shape I can ever remember him."

"I know, but things can start to change when someone gets into their mid 60s. Just keep it in mind."

Obviously, this discussion was a source of genuine anxiety to me, both because of the reality of what Jason was saying with regards to my health and endurance, and because of the possibility that another individual might enter my submissive domain and replace me.

Lauren had enlarged and framed some of the photographs from the wedding and displayed them prominently on the credenza in the foyer of the mansion as well as on another shelf in the main living room. Obviously, pictures of her and Jason and their wedding party were featured. However, off to the side were the pictures of me curtsying to and kneeling beside the bride and groom. As a present, Lauren had similarly enlarged and framed the companion photos from Amanda's and Ryan's wedding to be displayed in their new home. The closing date for the purchase of their new house was set for early November, and they hoped to move in before Thanksgiving. I suppose that I should be grateful that me being part of the family was represented somehow in the mansion I once owned, as all other photographs of me had long since been removed. The only pictures now were these few that so unambiguously showcased my servile status.

Another present involving a representation of me was given by Lauren to Amanda for her birthday on November 9th. Ever since she was a little girl, one of Amanda's favorite paintings had always been Il Saltimbanco by Antonio Mancini in the Philadelphia Museum of Art. It is a quite striking portrait of a young male street or circus performer. Standing on display on a small table, the boy's arms are folded, and he dressed in tights, a sort of frilly leotard and what appear to be ballet slippers. He clearly has a distressed, perhaps even ashamed, expression on his face. Some art scholars believe that Mancini was trying to convey a secondary meaning, drawing a parallel between the sufferings of Christ and man. I rather think that there is a more straightforward explanation for the pained expression on the boy's face: simply that Mancini's favorite model, Luigiello, was humiliated beyond belief at having to stand for hours in that ridiculous costume, aware of his friends or even his rivals staring at him from the street through the window of Mancini's studio -- pointing at him, laughing at him and later teasing him unmercifully. Whatever the explanation, it is no doubt a masterpiece (if you haven't visited the museum, I strongly suggest you Google the image, as it is a remarkable portrait).

Lauren commissioned an artist, a young Italian woman who recently graduated from the Rhode Island School of Art and Design, to paint a reproduction of it -- with me in the place of Luigiello -- for Amanda to hang on the wall of her and Ryan's new home. Of course, the painting would not be completed in time for Amanda's birthday, so Lauren instead gave Amanda a birthday card containing a postcard of Il Saltimbanco, the artist's business card and an explanation of her intention.

Amanda was overjoyed.

The artist, Alesia Agostini, was an attractive 25-year-old woman who had studied classical art at RISD. While still early in her career, she was already developing a reputation for her mastery of classical technique in reinterpreting old masterpieces in subversive, sometimes whimsical ways.

When Lauren first met with her, I served them both tea in one of my formal serving uniforms.

"So let me get this straight. You want to commission me to do a portrait of your maid, who used to be your husband, as a gift for your daughter. The maid is also your daughter's maid, as well as her father. You want me to paint this 62 year old man dressed identically to the preteen circus acrobat in Mancini's Il Saltimbanco. You want the painting to be an exact reproduction, except for the face and the figure, where I can use my artistic license," said Alesia.

"You summed it up well. What do you think? Is it too bizarre for you?" asked Lauren, uncertainly. "I've already had the clothes custom-made to fit him."

"Are you kidding? I absolutely love it! My price is $100,000. It will take about two months, during which he will have to pose at least 2 hours a day."

"I'm so happy. I couldn't imagine anyone else doing it but you. I'll get my checkbook now. Is a $50,000 deposit okay, with the balance upon completion?"

"Perfect. I can get started next week."

"Given how much you will need him to model, wouldn't it make sense for you to live here with us while you're working on your painting? We can provide you a studio with plenty of light, all of the art supplies you need, and all your meals. Gregory, your subject, has turned into quite a wonderful cook."

"That sounds like a great idea," said Alesia. And so, the deal was sealed.

When Alesia moved in the following Sunday, I greeted her at the door with a deep curtsy and brought in her bags and art supplies. Lauren gave her one of the more comfortable guest bedrooms on the second floor and converted a sunny, corner guest office on the third floor into an art studio. Alesia was beautiful, talented, mercurial and not lacking in confidence. Lauren and Amanda (and Jason as well, I believe) were quite taken with her, and soon she was a regular presence at cocktail hour, meals, watching movies in the home theater, etc. I was worried about what other household rituals she might be invited to participate in...

Alesia was fascinated by my story and my submission. Lauren made it crystal clear to me that I was to obey her completely -- not only in modeling for her but in any way she desired, as an honored, long-term guest at the mansion. So, I was Alesia's maid, cook, model and whatever else she wanted me to be. She fell effortlessly into the rhythm of the house when it came to ordering me around and humiliating me, constantly summoning me with one of the little bells spread throughout the mansion to bring her this or that. I generally posed for Alesia between 2:30-4:30 PM, when she felt the light was optimal.

The Saturday afternoon before Thanksgiving, Amanda and Lauren watched her paint as I stood on the table in my absurd street performer garb, arms folded and the requisite humiliated, distressed expression on my face. Highly uncomfortable and ashamed, I did not have to act to achieve the desired look on my countenance that afternoon.

"Even his hair is thick and curly like Luigiello's," said Alesia.

"Gregory has always had thick hair, and it tends to curl when it gets longer. However, if we didn't have it colored regularly, it would be almost white by now," said Lauren.

"The salt and pepper look is perfect," said Alesia.

Amanda said, "But what about his erection. He's pushing out the leotard in a way Luigiello never did. Mom, maybe you should lock him in his chastity cage when he's posing."

"No, I will paint his little erection just as I see it," said Alesia. "It will all be part of the contrast -- along with your father's gray hairs and the wrinkles in his face -- when my interpretation hangs on your wall next to a reproduction of the original."

"The chaste, beautiful boy circus performer juxtaposed with the horny, decaying old circus performer," said Lauren. "Brilliant, Alesia. I can't wait to see the finished work."

As they all talked about me, I felt my erection grow still harder in my tights. It was clearly visible again that evening when Alesia joined Jason, Lauren, Amanda and Ryan for my weekly maintenance spanking -- this time 25 strokes of the hairbrush over my son-in-law's knees, me in a new pair of maroon punishment tights. This was followed by 30 minutes with hands interlocked behind my head, legs spread, facing the five of them. I saw Amanda and Alesia exchange grins as they stared at my cock pushing out the nylon fabric.

However, the following day when posing for Alesia, for whatever reason I was uncharacteristically limp in my tights, much to her annoyance.

"I'm trying to get the contours right for your little stiffie and now, for once, you're soft. Great timing. Not!"

Alesia walked over the table, reached her hand under my leotard, and began rubbing my cock and squeezing my balls through my tights, looking me in the eyes as she did so. I had to think that, classical art scholar that she was, she must have been aware of all the male artists over the centuries who sexually molested or assaulted their female (and probably not a few male) models. Perhaps she believed she was keeping with tradition or possibly she felt she was evening the score a bit, but she clearly enjoyed the control she had over me. Still more irony in my now irony rich life: when I ran the law firm, I often spoke disparagingly of women's empowerment, but in my new life, I was very personally contributing to the empowerment of several young women on regular basis.