Lawyer2Maid Ch. 03

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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.

As winter turned into spring, I took stock of the fact that a year had passed since Jason and Lauren engineered my downfall–or (why mince words?) my enslavement.

Finalization of Lauren’s and my divorce took a little longer than expected, but it became official the last week of March. Jason and Lauren celebrated with a romantic, candlelit dinner for two at the mansion. Wearing one my most formal serving uniforms, I served them champagne, followed by the beef bourguignon I had prepared along with one of the best bottles of wine from my former wine cellar (2010 Chateau Rayas Chateauneuf Du Pape Reserve). I stood at attention by their table as they ate, kissed and talked about their future together. I was not invited to join them in the bedroom that night.

As they walked off to their bedroom after dinner, Lauren looked over her shoulder and said to me, “Nice job with dinner tonight, Gregory. You are a much better maid than you ever were a husband, or a father.”

“Thank you, mistress,” I replied, curtsying, surprised to feel tears well up in my eyes.

While I was not presented with an Easter bunny costume at Easter (to my pleasant surprise), I did not escape the holiday free of humiliation with respect to my attire. As I rushed around the kitchen, putting the finishing touches on Easter Sunday dinner (glazed ham, grilled asparagus, scalloped potatoes and deviled eggs), I had to be careful not to spill anything on my on the lavender maid’s uniform that Lauren laid out on my mattress that morning while I was cleaning. Satin with white petticoats with a matching lavender and white lace choker, I wore my it with my usual sheer, seamed black stockings and 3 inch heels.

Amanda was correct that Lauren quite fancied the look of a choker around my neck; she purchased me several in different styles and colors to go with my various uniforms (some with little ribbons tied into bows on the front). I think Lauren and Amanda both liked the fact that a choker resembles a collar, so denotes yet another level of ownership and submission (as if the uniform itself were not enough). I intensely disliked the confining feeling around my neck and was worried that I would be compelled to wear them during the summer; even without them, I found it oppressively hot last summer in my uniform and stockings, especially when serving outdoors with no air conditioning.

Besides Lauren, Jason, Amanda and Ryan, Easter dinner was to also include Penny and her boyfriend, George. Jason worked closely with Penny at the firm, and both Lauren and Amanda (who was about the same age as Penny) took a liking to her. I had to wonder if their bonding might also have something to do with Penny’s undisguised enthusiasm for witnessing, and participating in, my humiliation. When the doorbell rang, I hurried to answer it.

While Penny had always managed to dress fairly stylishly on her paralegal budget, there was a distinct change in the quality of her apparel since George had entered her life. Today, she was wearing an unmistakably expensive floral print dress with stockings and high heels. George, who wore nerdy, black glasses, was dressed effeminately in a white V-neck sweater with a pink bow tie and tight white pants. Penny handed me a bottle of Dom Perignon to chill in the refrigerator.

“Good afternoon, Miss Penny, sir.” After escorting them to the sitting room, where Jason, Lauren, Amanda, and Ryan were already enjoying a cocktail, I said, “Please make yourself comfortable. May I get you both a drink? We have some champagne already open, if that is acceptable.”

“Get me a glass of white wine,” ordered Penny.

I curtsied and said, “Right away, Miss Penny. Sir, what is your pleasure?”

I don’t think George knew what to make of me, or the entire situation for that matter. He said, shyly, “Oh, I guess I’ll have a glass of white wine too, please.”

“George, there’s no need to say please to the help,” said Penny with an annoyed expression.

“I’m sorry,” George replied, looking ashamed.

When I served him his drink, curtsying, he said, “Thank you.”

Penny snapped at him, “What did I just tell you about how to address the help? You don’t say please or thank you. This is Jenkins’s job. He is the maid. Don’t embarrass me.”

George repeated, “I’m sorry,” looking down.

Sensing the tension, Lauren interjected, “Penny’s quite right, dear. Pleasantries are completely unnecessary when interacting with the help. I love those shoes, Penny! Are they Jimmy Choos?”

“They are!”, beamed Penny. “George bought şerifali escort them for me yesterday at Saks as an Easter gift along with this dress.”

“Gorgeous. The dress looks great on you,” said Amanda.

Penny replied, “Thanks. I love the shoes but I’m still trying to break them in and my feet hurt a little bit. George, would you mind giving me a little massage?” Penny threw her feet up onto George’s lap. He removed her shoes and began massaging her stocking-clad right foot.

After a moment, Penny said, “Most of the pain is in my heel. You really can’t get good pressure on the heel unless I elevate my feet. It might be better for you to massage them from the floor, George.”

George looked around uncertainly, making momentary eye contact with me, as he said, “Of course, honey.” He then got down on his knees and continued the massage. Penny smiled contentedly and I saw her wink at Amanda.

Observing this, I began to wonder if Rebecca was the only one with whom I would be sharing the submissive spotlight over the coming months.

Indeed, the next time I saw Penny and George was at a Memorial Day weekend party that Lauren and Jason hosted at the mansion. It was a hot day and the pool had recently been uncovered to start the summer season. It was a relatively small gathering that included Forrest and Jane, Samantha from my old firm and, of course, my daughter and Ryan. I was dressed in a formal serving uniform (classic black and white, fortunately, but with the matching choker) serving cocktails to the guests seated around the pool when Amanda escorted Penny and George into the backyard. Accompanying them, however, was a muscular (“jacked,” I believe, is the term of art) young man, already shirtless in a bathing suit and flip-flops. Penny was wearing a bikini under her robe. I did a double take when I looked at George: he was wearing tight, yellow shorts and a T-shirt with the word “CUCK” printed on it in large pink letters. He still had on his nerdy black glasses, but around his neck was a studded pink collar, and he was blushing brightly.

Having just gotten everyone fresh drinks, I was able to catch much of the conversation that ensued after Penny introduced the other young man to Lauren, Jason, Amanda and Ryan.

“Please meet my new boyfriend, Kyle, everyone,” said Penny. “Georgie, go to the pool house and change into your swimsuit.”

“Yes, goddess”, said George as he scurried off to the pool house.

It was quite an interesting story that Penny had to tell.

Apparently, Penny met Kyle at a nightclub in Central Islip. He is a 20-year-old construction worker training to be a professional wrestler — yes, the kind you see on TV. They dated a few times, and slept together twice, before Penny told Kyle about George. Kyle’s first reaction was anger and jealousy, but Penny assured him that there was simply no contest between the two of them. Although it took a little while, she was also able to convince Kyle that George, who spent a great deal of money on her, might play a useful role in their lives.

“I told Kyle about you guys and what you did you with Jenkins. I explained to him that there is a whole world out there of unusual relationships that work for people. It’s funny. Before that day when I watched Jason put Jenkins through his exercises, whipping him in his tights, and forcing him to lick his boots, I was really pretty vanilla. I mean, I let a guy spank me once or twice or played around with handcuffs a couple of times, but that was the extent of it. But seeing that, it stirred something in me. Samantha said I had what she called an epiphany. I wasn’t able to get it out of my mind. That’s why I’m always asking if I can come over to watch Jason and Forrest discipline Jenkins. I find it incredibly hot watching a superior man dominate a weaker one. I decided I had to have something like that in my own life. Well, now I do,” Penny smiled.

When Penny told George about Kyle, he was incredibly distraught and begged her not to break up with him. Penny showed George a picture of Kyle and made it unambiguously clear that he had zero chance.

“I told Georgie that he’s a good little beta boy, and that I appreciated all the nice things he bought me and all the nice dinners, but that he just doesn’t do it for me sexually, that he’s too small and too passive to ever satisfy me in bed. Or anywhere else. I told him that Kyle was a real man. Georgie actually started crying, if you can believe it. He was SO pathetic. I told him that there might be a way for him to stay in my life, but that he probably wouldn’t like it. He actually got down on his knees and said he would do ANYTHING to stay in my life. Well, now we’re putting that to the test. I think he believes that someday I’ll get tired of Kyle and he can win me back. Fat chance, ” she laughed. “Here he comes.”

George emerged tentatively from the pool house and walked back over to the table where everyone was sitting. He was still wearing his shirt and collar, but now had on a bright yellow speedo. Beneath the seyhan escort nylon fabric, a chastity cage was clearly visible.

“Cuck, get me a beer and get your goddess a glass of wine, double quick.” Kyle ordered George. “I’m going to check how long it takes you on this pretty Rolex watch you bought me.”

Lauren said, “That’s not necessary, Kyle dear. That’s what Gregory is here for.”

Penny said, “Oh, please let Georgie do it, Lauren. Our relationship is still new and he needs to get used to submitting to Kyle’s authority in public.”

Lauren replied, “Well, of course, dear. Whatever you like. Gregory, at least show George where we keep the beer and wine. And freshen up our drinks, while you’re at it.”

“Yes, mistress, of course.” I curtsied. “Please come with me, sir,” I said to George.

After we returned with the drinks, Kyle looked at George, snapped his fingers and pointed to the ground at his feet. After handing Kyle his beer and Penny her glass of wine, George got on his hands and knees, and Kyle put his feet on his back, using him as a footstool.

Penny giggled, “You see? Isn’t it wonderful! And I owe it all to you guys. You have been such an inspiration to me.”

Jason said, “Let’s toast to Penny, Kyle and Georgie.” They all clinked their glasses and drank, laughing.

Amanda asked Kyle, “So, you’re really training to be a wrestler?”

Kyle replied, “Yes, ma’am. I should be making my debut on Monday Night RAW this fall. Meanwhile, I’ll be going on tour this summer.”

Penny said, “You see, Kyle is training to be a heel. There are the alphas, or heels as they’re called, and there are the betas, or jobbers. They’re the ones that usually wear the pink tights or pink trunks as they get tossed around the ring by the heels.”

Kyle explained, “Some of the guys start off as jobbers, and then later become heels. I got no interest in that. I’m training hard, but I’m gonna be a heel from day one, until I retire.”

Penny added, “It’s so fun! We play this game where Kyle and Georgie wrestle and the winner gets to have sex with me while the loser has to do the winner’s laundry and clean his house. Like there’s any real contest. Ha ha. Sometimes they wrestle naked, but usually Kyle wears his camouflage trunks and Georgie has to wear pink jobber tights. I then get to watch Kyle completely manhandle him. He throws him around like a ragdoll. The match ends when Kyle puts Georgie in some really humiliating submission hold. He usually squeezes his balls until Georgie begs for mercy. Then Kyle makes him lick his sweaty feet. Just like Jason with Jenkins! After that, Kyle usually spanks Georgie before taking me to bed. But Georgie gets to watch sometimes, don’t you Georgie?”

“Yes, goddess,” said George from his position beneath Kyle’s feet.

“Sex with Kyle is always great, but after watching him smack Georgie around, it’s mind blowing.” Penny covered her mouth and said, “I’m sorry, I guess I’m sharing way too much.”

Lauren said, “Not at all dear. We are very happy for you. And I can relate.”

Amanda said, “You go, girl!”

I selfishly wondered what implications there might be for me (besides sharing that spotlight of shame) with George and Kyle coming onto the scene. It was going to be a fascinating summer.

The first few weeks of June were consumed with preparations for Lauren’s and Jason’s wedding at the end of the month, as well as Amanda’s and Ryan’s two weeks later. Both ceremonies and receptions were to take place at the mansion, which had ample room to seat people both inside and outside.

In case you were wondering, no, I was not going to serve as a bridesmaid at either ceremony. I was simply the former husband/maid and father/maid. Lauren and Amanda hired a dressmaker to design and produce custom uniforms for me to wear at their respective weddings. While my typical uniform came down to mid thigh to an inch or two above the knee, Lauren wanted me in a longer uniform for her ceremony: black and white, the skirt extending to the middle of my shins, with a matching black and white lace choker that covered virtually my entire neck. I was to change into a shorter uniform (fortunately with a much thinner choker) to serve drinks and hors d’oeuvres at the reception. Amanda, who planned on wearing a long white gown for her wedding, commissioned a white satin uniform of typical length, with black lace petticoats, apron and collar, and a black satin cap with white lace trim. Accompanied by seamed, sheer black stockings and 3 inch heels, of course, in all cases.

There was extensive discussion about what role I could play in Amanda’s ceremony that would showcase my dual status of father of the bride and the family maid (probably not an issue encountered by too many wedding planners). It was finally agreed upon that, while Jason was to give her away, I was to hold the train of Amanda’s long wedding dress as she walked down the aisle with him. Although this task usually falls to the bride’s maid of honor, it was decided that for me to do it would allow me to take part in side escort the ceremony, but in a way that would accentuate my role as servant. After Amanda stepped onto the altar, I was to curtsy deeply to her and Ryan, then pivot and deep curtsy to Lauren and Jason, then to Ryan’s parents and finally to all of the assembled guests, before taking my seat in the back row.

Lauren wanted things to be picture perfect, so in the days leading up to her and Jason’s ceremony, I was kept exceedingly busy cleaning every inch of the mansion;. mowing the lawn, trimming the hedges, weeding the garden; washing and detailing Jason’s and Amanda’s Porsches, Lauren’s Mercedes and Ryan’s Land Rover

(my eyesore Subaru safely hidden in the garage).

It would be impossible to chronicle all of the myriad humiliations I suffered before, during and after these two momentous occasions. Therefore, I will simply highlight the ineffable few that stood out and stayed with me for years to come:

Greeting Lauren’s mother, Helen, at the door when she arrived from the airport. At 63, she was only a couple years older than I was. She had always disapproved of our marriage, believing that I robbed the cradle. A proud feminist, she was deeply disappointed that her daughter would marry someone as domineering and chauvinistic as I. When I curtsied to her in my working maid’s uniform, she said, “Well, Gregory, Lauren and Nicole both told me about your transformation, of course, but I had to see it to believe it. I’m still not sure I believe it. Curtsy for me again.”

Receiving five strokes of the cane each from Jason and Ryan for smudges found on the sterling silverware I had inadequately polished, while their fiancés and Helen looked on approvingly.

Giving pedicures to the three generations of Helen, Lauren and Amanda as they watched Barbie in the home theater.

Serving as caddy in my school boy uniform to Jason’s father (“Well, son, when you told me about all the abuse you suffered from that asshole you worked for, I told you to cut your losses and quit. Hanging in there paid off pretty handsomely, I guess.”) in a foursome that also included Jason, his 24-year-old younger brother and Paulo.

Being bent over the kitchen counter, and given six smacks with a wooden spoon across my bottom of by my niece, Olivia, for having placed the braised short ribs on the wrong end of the buffet table at Lauren’s and Jason’s reception–with two young women on her catering staff looking on, snickering.

Giving pedicures, with extended foot massages, to Amanda and all eight of her bridesmaids (“This is really your dad, Amanda?! How wild!”), followed by shining the shoes of Ryan and all eight of his groomsmen (as they were being worn, an hour before the ceremony). Besides Olivia, Mia, Isabella, Jason’s brother and Paolo, the wedding party members consisted mainly of Amanda’s and Ryan’s respective sorority sisters and fraternity brothers from Dartmouth, all of whom seemed genuinely excited to be part of such an unconventional event.

Being photographed in front of all the guests at both weddings. Both couples used the same wedding photographer. I was included in only three pictures (the exact same for both couples): one with me facing the bride and groom in the position of a deep curtsy; another with me standing at attention off to the side of and slightly behind the bride and groom, holding a tray with two glasses of champagne; and the third with me kneeling next to the smiling newlyweds, the bride’s hand resting in a proprietary manner upon my head.

Holding the train of Amanda’s gown as she danced with Jason during the father/daughter dance (at one point during the dance, I stumbled in my heels and fell to the floor briefly, creating a moment of levity).

Receiving “six of the best” in my punishment tights from Ryan in front of all of the inebriated members of the wedding party (except for young Isabella and Olivia), after I spilled onion dip on Mia at the after-party held at a beach house that Amanda and Ryan had rented nearby–followed by 45 minutes in my penance position facing the drunk, laughing college students, my erect cock saluting them through my tights (in spite of my heroic efforts at concentration, willing it to subside).

I have used the adjective “surreal” several times to describe my predicament, but things were never more surreal than during this three-week period, especially on the two big days themselves. Memorable to say the least.

The day after their wedding, Amanda and Ryan departed for a 10-day honeymoon to the Greek islands. Lauren and Jason, due to Jason’s work commitments, were planning on delaying their honeymoon until the second of August when they were embarking on a two-week trip to the Amalfi coast.

While I have obviously focused on holidays and big events over the last several months, my normal routine of drudgery continued throughout this period. This included the biweekly cleanings of my old law firm offices; the regular proofreading work; the semi regular cleanings of Forrest’s and Jane’s house; and, of course, all of my daily duties around the mansion. Just as my cooking skills had improved, I fortunately had learned to make fewer mistakes in proofreading, and had learned what was necessary to satisfy Jane’s high expectations of cleanliness, resulting in less frequent punishments. Don’t get me wrong, my punishments were fewer than they had been in the past, but were by no means nonexistent.

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