Lawyer2Maid Ch. 05

Note: All characters involved in any activity of an adult or sexual nature 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 I write these words in my journal, I am sitting at the small table I use as a desk in my maid's quarters in Amanda's and Ryan's mansion in Amagansett. I am now 82 years old. However, just as I used to be mistaken for being in my mid-50s when I was in my early 60s, many people now think I'm under 70. For this, I credit reasonably good genes, the high-quality of healthcare I have continued to receive even in my servitude and Jason's and Ryan's rigorous exercise regimen, which continues to this day (albeit moderated to accommodate my increasing physical limitations).

My genes were not altogether favorable, however, as I was diagnosed with prostate cancer four years ago. Fortunately, it was caught early and I now appear to be cancer free. My relatively good health has allowed me to continue serving as maid to Lauren and Jason as well as to my daughter and son-in-law. And of course, to my grandchildren, Dylan and Harper, both now 20 years old. Following in the footsteps of his parents, Dylan attends Dartmouth. Harper, on the other hand, is a junior at the University of Pennsylvania.

I believe that I have remained mentally sharp, but that is for others to judge, I suppose. Fortunately, Jason has continued to give me interesting reading assignments that I am required to analyze in written essays. He continues to be a tough grader and I continue to have regular sessions over the spanking bench in the dungeon or across his knees for work he deems subpar (for the record, I'd like to point out that I've also received several A's over the years, resulting in rewards, such as steak dinners or glasses of quite good wine, scotch, etc.) The humiliating punishments are a small price to pay for the privilege of reading the interesting fiction and articles that Jason assigns me; after my punishments, we often have spirited discussions about the material (usually while I massage his feet or give him a pedicure). But my bigger point is that I believe this intellectual stimulation has helped me maintain my mental acuity.

Thankfully, my tedious proofreading responsibilities came to an end after Jason left the practice of law, roughly a decade ago, to dedicate his time to writing and making documentaries and podcasts about our lifestyle (by which I mean his and Lauren's subjugation of me) and the BDSM lifestyle in general. I was appointed his research assistant. Jason has become quite the celebrity, and his books, speeches, podcasts, and films have been highly lucrative. I suppose it's fair to say that I, too, have become something of a celebrity; when Jason said to me after Eddy Bolson's article about me appeared in The New York Post that I could become the national poster child for sissy maids, I guess he wasn't kidding. I'm sorry to say that Jason allowed Bolson to play a prominent role in his award-winning podcast about my plight. This was appropriate, I concede, given the critical role Bolson played in making my humiliation known to the general public. Nevertheless, it was intensely humiliating for me to have to serve drinks and dinner in my formal serving uniform to the man who exposed me, as he and Jason discussed ways to further disseminate the story through multimedia (in a meta touch, even that shameful encounter was described in the podcast). I guess it's fair to say that Bolson got his revenge on me, and then some.

Forrest retired from full-time practice about a year after Jason left the firm, but they continue to be friends. I am still sent to clean his and Jane's house periodically (fortunately, they downsized a few years back and now live in a 3500 square-foot home). In fact, just last week I found myself over Forrest's knees for 25 hard spanks after Jane discovered dust on the back of the toilet lid.

Ryan has had a very successful career as a hedge fund manager, allowing him and Amanda to sell their (relatively) modest 3000 square-foot starter home approximately nine years ago and purchase the 15,000 square-foot home in which I presently sit. It is a very traditional manor house, in the British style, straight out of Downton Abbey. I should know, because over the last 20 years, since the birth of my grandchildren, I have somewhat anachronistically lived the life of a Downton Abbey servant -- or rather, I should say, servants, as I have fulfilled multiple roles (almost all of them within the lower echelon of servants in a wealthy household), ranging from lady's maid to scullery maid, from second footman to boot boy. In fact, there have been countless times over the last two decades where I fulfilled two or more of these roles during the course of the very same day. To my grandchildren, however, I appeared merely as some version of Mrs. Doubtfire in a maid's uniform. Amanda and Ryan carefully sheltered Dyan and Harper. All of my punishments and more overt humiliations took place behind closed doors or when the children spent the day or night with Lauren and Jason. Until they turned 18, of course, when the full extent of my subjugation (and the story behind it) was revealed to them, and they became enthusiastic participants in it.

I say I lived the life of a Downton Abbey servant "somewhat anachronistically," because over the last two decades -- with the country abandoning its long history of democratic rule for a more authoritarian form of government -- master/servant relationships have become more common than they were in the past, or at least a lot more out in the open. What do I mean by this?

American society has fundamentally changed. The pay gap between rich and poor has widened substantially, so that there is now truly a permanent aristocracy and a permanent servant class in the United States. I don't mean to suggest that the American dream is completely dead, as there are still those fortunate few who manage to rise from modest means to become wealthy. But that is certainly much harder to do now than 50, or even 20, years ago. It was nearly twenty years ago that Jason and I talked about how cruelty and authoritarianism were already becoming more ingrained in our culture. That trend has accelerated considerably since our discussion, manifesting itself in many ways.

Twenty years ago, it was rare to see maids or butlers dressed in traditional uniforms and behaving with exaggerated, formalized deference towards their employers. That has now become quite common, with an affluent, ruling class that enjoys conspicuous consumption. One of the most conspicuous ways of showing off one's wealth is to have servants who unambiguously look and act like servants. Even within this context, however, Ryan took things to an extreme.

The trend towards autocracy and cruelty has also manifested itself in the workplace, where the authoritarian administrations that have been in power (and show no signs of relinquishing it) have banned diversity, equity, and inclusion initiatives. Some employers, of course, still attempt to promote these qualities quietly. However, others (likely a majority) revel in the lack of diversity, equity, and inclusion in their companies. Unions have been greatly weakened. Laws have been changed to make it much easier for employers to fire people. Artificial intelligence has eliminated many jobs, giving employers still more leverage over those workers lucky enough to have decent jobs (or even less than decent ones).

Indeed, it's fair to say that a large portion of the progressive advances over the last hundred years have been reversed. But not all of them, interestingly. There is a new class of oligarchs, but several of them are female. In fact, the first truly authoritarian US president had a female vice president. She is now president of the country and bills herself as a feminist. Many believe that feminism has been turned on its head. There are oligarchs of different races, as well. The big point is that there is a huge and growing gap between the rich and the poor, between the powerful and the powerless, between the masters and the servants. The powerful set the rules and the weak follow, their powerlessness institutionalized.

And this trend has manifested itself in the bedroom (or the dungeon). I noted many years back that it was surprising to discover how many people there were in the BDSM scene. But whereas in the past, most of the people in this lifestyle were very discreet about it, most of those in the scene today flaunt it openly. It is not unusual these days to see couples walking down the streets of Manhattan or East Hampton (or rural Virginia for that matter), holding leashes attached not to dogs but to their cuckold husbands or cuckquean wives or some other variety of sexual submissives. I suspect that Jason and I may have played some small role in this change, as our story became widely known.

But I don't wish to simply summarize the last 20 years without sharing with you some of the more memorable moments and events that occurred. While I certainly can't say that I succeeded in fully balancing the scales of karma during that period, I think it's fair to say that I made some real progress towards that end.

Reflecting on the last two decades, I still marvel at how I watched Dylan and Harper evolve from helpless infants into the self-assured, indeed quite intimidating young adults who now wield such power over me.

For the first few years or so following their birth, I spent the majority of my time (night and day) at Amanda's and Ryan's home, helping to care for them -- or, to be more precise, doing all of the cleaning, cooking and shopping, so that Amanda and Felicity had ample time to care for them. My direct interaction with them was carefully limited by my daughter and son-in-law throughout their childhood. I would usually return to the mansion twice a week, to clean it thoroughly during the day and to be put to use orally in the bedroom at night, servicing Jason, cleaning his mess out of Lauren, sucking their toes, etc. My absence from the mansion seemed to incite them to work me harder, both inside and outside the bedroom, when I was around.

Lauren, not surprisingly, also spent a great deal of time at Amanda's and Ryan's home, doting on her new grandchildren. Still in her early forties and as lovely as ever, she certainly did not fit most people's image of a grandmother. Ryan was very busy with his fledgling career at the hedge fund, and Jason was working long hours as a new partner with a very robust book of business. Consequently, I usually only saw my two masters at night and on weekends during this time.

Most of my time was spent at the beck and call of Amanda and Felicity. Felicity was the full-time au pair, trained at an exclusive agency in the UK (one supposedly used by members of the British royal family), hired by Ryan and Amanda. Slender with longish, dark brown hair, she was 19 years old and spoke with a refined (borderline prissy) British accent. In the weeks before Amanda gave birth, I heard Ryan express his strong conviction multiple times that a British nanny from a top agency would be best suited to help raise the children in the proper manner. From the get go, Amanda and Ryan made it very clear to Felicity -- who, of course, had done her own research and was well aware of who I had been, and who I was now -- that I was at her disposal to help with the children, but that I was fully subordinate to her. Fully empowered by my daughter and son-in-law, Felicity set the tone for our relationship from its inception. No doubt due to her formal training, she addressed Amanda as "ma'am" and Ryan as "sir," but otherwise was treated almost as their equal -- she sat with them at the table over meals (served by me), watched television with them in the family room, accompanied them on trips, etc.

I remember well the first time that I met Felicity, the day after I got back from one of my dreaded summer trips to Virginia. Ryan was at work and Amanda was shopping with her friend, Mia. When I arrived at the house in my uniform, Felicity was sitting on the living room couch listening via a baby monitor to the sleeping twins in their nursery upstairs.

When I entered the room, she made no attempt to get up from the couch (whether because she was feeding Dylan or because she didn't believe I warranted the effort, I cannot say) and said to me, "Ah, yes, you are Amanda's father, the maid. Who was once a famous barrister, if I'm not mistaken. I know your name is Gregory, but seeing how you're dressed, I'm not comfortable calling you Gregory. Rather, I will address you simply as maid."

I curtsied to her and replied, "I have heard a lot about you, Miss Felicity. It is a pleasure to meet you."

"I've heard a lot about you as well, maid. Do you not think that a deep curtsy is appropriate when meeting someone in a superior position to you in the house for the first time?"

"My sincere apologies, Miss Felicity," I replied, as I dipped into a deep curtsy.

"Your apology is accepted. From now on, I expect you to deep curtsy to me whenever I enter or leave a room that you are in or vice versa. I assume that is how you behave when the master or lady of the house enters the room. Isn't that correct."

"Yes, miss."

"Good. Now, the house needs a good cleaning. Surely you have a more appropriate uniform for cleaning?"

"Yes, miss. In my room, there are several uniforms suitable for different occasions. May I please be excused, miss?"

"You may. My room is the guest bedroom on the second floor. See that you don't misplace any of my belongings as you clean around them."

"I shall be very careful, miss," I said, excusing myself with a deep curtsy.

Ryan and Amanda had obviously selected this young woman with great care. I left the room with no doubt as to where things stood between us and with no illusions about what lay in store for me working under her authority. At the time, of course, I had no idea for how long that would be. It ended up being for nine years, until Jason had made a sufficient fortune to purchase the enormous Downton Abbey-like mansion. At that point, Felicity returned to the UK, and Jason and Amanda hired an experienced 53-year-old butler and his wife, a 49-year-old housekeeper. They became the senior male and female servants in the house; I will leave it to you to guess who single-handedly filled the responsibilities of the staff of lower servants.

Felicity sometimes dressed casually, but more often than not wore a blouse and skirt, frequently with stockings or tights (except for the summer months, when her legs were usually bare) and low heeled shoes. While not a great beauty like Lauren or Amanda, Felicity was a good-looking young woman not entirely devoid of sex appeal despite her prudish demeanor. I have to believe that she had some awareness of her sex appeal, because of certain ways she behaved towards me from time to time. For example, she had a habit of dangling her heel, especially when I was on my knees in close proximity to her feet (usually cleaning up some mess on the floor).

I recall one afternoon when Amanda and Felicity were sitting in the living room talking while the twins were napping. I had just served the two of them afternoon tea -- Felicity enjoyed having tea and scones in the afternoon, like the proper British girl she was -- and was standing at attention in my formal serving uniform, ready to refill their cups

Amanda said, "Father, my feet are killing me. I would like a massage now."

"Right away, Miss Amanda. Let me just refill both of your cups before I begin," I replied, with a curtsy. "May I use my kneepads?"

"Of course, father."

After thanking her, I put the kneepads over my knees, knelt down at her feet, and began strenuously massaging them. Her legs were bare but for the anklet I had bought her for Christmas, with the key to my chastity cage dangling from it. I had not had a release in over three weeks and stared at the key longingly. As much as I did not wish to become aroused by daughter's lovely feet, my cock throbbed painfully in its prison.

After I finished, Amanda said, "Felicity, you've been running around an awful lot the last couple of days. Would you like a massage as well?"

"That is very kind, ma'am. I believe I would enjoy that."

I found Amanda's remark to be quite ironic, as I spent far more time on my feet, standing as well as "running around," than Felicity-- and not simply over the last "couple of days," but every day.

As I worked on her feet (quite pretty in their own right), Felicity smiled contentedly and my cock swelled uncomfortably in its prison.

Amanda said to her, "You seem to be enjoying that massage. Feel free to ask him to give you one anytime you feel the need. He actually has become quite good at them. And pedicures as well. Tomorrow I will have him do both of our feet. I have a pretty wide selection of nail polish, so I'm sure you'll find something that you like."

"That sounds wonderful, ma'am. Thank you."

"Don't mention it, Felicity. You are a lifesaver."

I remember having the feeling at the time that I would become quite well acquainted with Felicity's feet. I was not mistaken.

I was locked up in chastity most of the time and releases were few and far between. My rare releases were generally granted on sporadic weekends in Jason's and Lauren's bedroom -- I had almost forgotten by then that it had once been mine -- when they would take pity on me. The conditions under which I was permitted to come were unwaveringly degrading, naturally, but beggars can't be choosers. Usually, I was compelled to hump something (the floor, Lauren's leg, Jason's boot, etc.), but one time (after weeks of confinement) Jason tied my hands and feet, clamped my nipples, and simply beat my balls and cock with a wooden spoon until I erupted through my pantyhose. There seemed to be an almost direct correlation between the intensity of my humiliation and the intensity of my orgasm, and that particular one was intense indeed. But it was followed by weeks of additional confinement.

I was almost always locked at Amanda's and Ryan's house but, mercifully, was never invited into their bedroom (even in our supremely decadent lifestyle, some things were a bridge too far). I had to ask Ryan's -- or when he was away on an extended business trip, Amanda's -- permission to be released to clean myself, something I found to be staggeringly humiliating. Ryan would typically demand some special service or particularly degrading act I would have to perform before agreeing to unlock me. Sometimes he would make me jump through hoops, quite literally, reverting back to the dog training routine that he found so entertaining. These sessions took place in the basement, usually only with him and myself -- me wearing my punishment tights and he either in workout clothes or equestrian gear, depending on his mood. When he was more pressed for time, he might order me to do push-ups, kissing his foot each time I lowered myself to the ground. Still other times, I would have to wash and wax his Land Rover or polish all of his shoes. Keep in mind that all of this was simply so that I could exercise basic personal hygiene, nothing more.

When Ryan finally agreed that I had earned the right to be temporarily liberated, he would take his copy of my chastity key out of his locked desk drawer, sit down in his office armchair and make me stand next to him as he unlocked me. I was then compelled to clean myself in the small bathroom next to my bedroom, directly in front of a spy camera mounted on the wall next to the toilet. This was obviously to ensure that there was no unauthorized masturbation. When finished, I would promptly return the key to him and he would relock me.