Date: Fri, 9 Feb 2024 22:47:37 +0000
From: Clarice
Subject: Lawyer2Maid V

Synopsis: Conclusion of story of brutal social downgrade of once
powerful, arrogant attorney, who becomes the maid of his
(multigenerational) family and former coworkers.



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 81 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 two 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 are now 18 years old, and will be college bound in the fall.
Following in the footsteps of his parents, Dylan will be attending
Dartmouth. Harper, on the other hand, will be attending 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 he built 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 17 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, from stable boy to whipping boy. In fact, there have
been countless times over the last 17 years where I fulfilled two or more
of these roles during the course of the very same day.


I say "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 much 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 eighteen 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 (and by extension Amanda and the twins) took things to an
extreme. But more on that later.


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.


And the 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 18 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 18 years, 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 two 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. During this period, 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.


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 them at
night and on weekends during this time.


Most of my time was spent at the beck and call of Amanda and Felicity.
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 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 feeding Dylan with a bottle while Harper
napped in her crib.


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. 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. But I will get to that later.


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 wiping up bits
of food dropped on the floor by one of the twins).


I recall one afternoon when Amanda and Felicity were sitting in the
living room talking while the twins were napping in their playpen. 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 everyday. As had been
pre-ordained, I had plenty of responsibilities regarding the twins, but
they were largely ones that did not permit direct bonding. I changed most
of their diapers, day and night. Before their birth, I  honestly don't
believe I had never changed a diaper before in my life (I was working all
the time when Amanda was born, but even on the rare occasions that I was
around, I felt that changing diapers was the responsibility or Lauren or
the part-time the nanny we had hired, certainly not mine). I did all the
shopping, prepared their formula, cleaned their rooms, washed their
linens. Occasionally, of course, when Amanda or Felicity were occupied, I
would fill in and feed them a bottle or even do an airplane simulation
with a spoon to try to get them to eat their baby food. Sometimes I would
even bounce then on my knee, play with them or hold them to comfort them.
But Amanda and Felicity saw to it that these moments were the exceptions.


As I worked on her feet (quite pretty in their own right), Felicity
smiled contentedly and my cock continued to swell uncomfortably.


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.


Those first few years after the birth of Dylan and Harper were
challenging for several reasons, not the least of which being that I was
locked up in chastity for most of that time and releases were few and far
between. Almost always dressed in a maid uniform during this period,
serving Amanda, Felicity, Lauren, and any number of friends and relatives
who came over to visit the twins, I was in a near constant state of
submissive arousal and sexual frustration.


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.


Similarly, when Ryan was traveling, I would have to ask Amanda for
permission to clean myself. She would extend her foot for me to remove
the key from her anklet, and I was then allowed a few minutes to wash
myself and then lock myself back up, all in view of the camera. I would
then put by uniform back on, return to where she was sitting and kneel
down to replace the key on the chain around her ankle. I have no idea
whether or not they ever watched the camera recordings (I can only hope
not); the threat alone was more than sufficient to prevent me from ever
trying to cheat.


Felicity grew quite fond of my foot massages, to the point that I was
expected to give her one pretty much every other day after Dylan and
Harper were put to bed. During the winter months, she liked me to rub
moisturizing lotion into feet after I massaged them. She was an exacting
supervisor, constantly criticizing me; instructing me to tidy up the
bathroom, iron her skirt, cut the crust off her cucumber sandwiches;
admonishing me to straighten the seams of my stockings, stand up
straight, etc. I could go on and on.


Following the twins' first birthday, it was decided that I should start
addressing them as Master Dylan and Miss Harper. They obviously didn't
understand the meaning of words of that point, but Ryan argued that they
were little sponges who would very quickly pick up on my status in the
household -- not only by the way I dressed, but how I interacted with
them, as well as with others in the house. He was quite correct.


Following their fourth birthday, I was required to begin curtsying to
them when I entered or left a room they were in or when asked by them to
do something for them. Again, at that age, they couldn't possibly know
what a curtsy signified, but it quickly became obvious to them that it
was a gesture made by the one individual in the house following orders to
those several who were issuing them.


Both children were highly intelligent and precocious, Harper in
particular, and felt very comfortable ordering me around by the time they
were entering kindergarten. That is not to say that they didn't
experience some confusion about the household's unorthodox dynamics.


One afternoon, after returning from a playdate at one of her friend's
houses, 6-year -old Harper began asking questions of her parents, who
were sitting in the living room with her and her brother. Felicity had
the day off, but I was standing off to the side of the room in my
uniform, having just served everybody soft drinks.


"Mommy, why do you call the maid father sometimes?"


"Well, honey, that's because our maid is my father. You hear Grandma
Lauren call him Gregory. His name is Gregory Jenkins."


"But if he's your father, wouldn't that mean he's my grandfather? And
Dylan's?"


"That's right sweetheart. You're such a smart girl."


"But when I was over at Laura's house, I met her grandfather, and he
wasn't dressed like a maid."


"Well, sweetheart, your grandfather is a very special grandfather. When
he was younger, he was very, very naughty, especially to Grandma Lauren
and me. But to daddy and Jason too. And now he wants to make up for how
naughty he was by doing things for Grandma Lauren, me, daddy and for you
and Dylan."


"Is that like when I have to sit in the naughty chair in a timeout?",
asked Dylan.


"That's almost exactly what it's like, honey. You're so smart too,
just like your sister. The only difference is that your grandfather is in
a permanent timeout. But that's what he wants, to make it up to all of
us for being so naughty. Isn't that right, father?"


"Yes, Miss Amanda." I replied, curtsying.


"Why does he bend down like that?", asked Harper.


"That's called a curtsy, sweetheart. It's the way your grandfather
shows his respect for us. Just like when he calls you Miss Harper or
calls your brother Master Dylan. That's his way of showing he respects
us. Sort of like how you call your teachers miss".


"Are we his boss, then?"


"Well, yes, sweetheart you are his boss. All four of us are his boss. So
is Grandma Lauren and Jason. Even Felicity."


"But we call him maid. Should we call him grandfather instead? And
aren't maids supposed to be girls?", asked Dylan.


"Those are good questions, honey. Maybe we need to think of something
new to call him," said Amanda.


Without missing a beat, Harper answered, "I know! Let's call him
grandmaid!"


"You are brilliant, sweetheart. Grandmaid it is!"


As you can probably imagine, things did not get easier for me following
that conversation. Whereas previously the twins had undoubtedly sensed
that I was subservient to them -- as well as to everyone else at their
house and their grandmother's house -- they had now been expressly told
this was the case by their mother. And like the precocious children they
were, they took full advantage of the situation. Far from discouraging
them in this, their parents and Felicity looked on with admiration as
Harper and Dylan became more confident in exerting their authority over
me and encouraged such behavior with positive reinforcement.


Their father in particular set about immersing them in fiction and
nonfiction about the lives of aristocrats and their servants. Because
much of the fiction portrayed servants in a sympathetic light vis-a-vis
their often abusive masters, Ryan tended to favor history over fiction,
with a few exceptions; I believe that he was also very selective in what
he shared with them. It was Ryan's goal to instill in his children the
firm conviction that they were aristocrats by birthright who fully
deserved to be waited on hand and foot by servants. As his career with a
prominent hedge fund took off, he was making more and more money each
year, getting closer to turning his ideal of being a truly wealthy and
powerful aristocrat into a reality.


Meanwhile, following that conversation in which Harper coined my new name
of grandmaid, Ryan, Amanda and Felicity no longer attempted to conceal
some of their more overt displays of dominance over me from the children.
While my maintenance spankings were still conducted after the children
had gone to bed, thankfully (at least for the time being), the twins were
now routinely present as I knelt before their father, shining his shoes,
or as I gave their mother a pedicure or Felicity a foot massage.


Hours were spent with the four of them and Felicity watching shows such
as Downton Abbey and Upstairs Downstairs in the family room, while I
served them popcorn, drinks, etc., curtsying to them just as the maids
they were watching on the widescreen TV curtsied to their masters and
mistresses. Ryan would read them excerpts from books such as Tom Quinn's
Gilded Youth: A History of Growing Up in the Royal Family, Alison
Maloney's Life Below Stairs: True Lives of Edwardian Servants and
Margaret Powell's Below Stairs.


By the time they were eight, Harper and Dylan had an almost encyclopedic
knowledge of the hierarchy of servants in a wealthy household and their
duties: the butler and head housekeeper at the top; followed by governess
and lady's maid among the female servants and chauffeur, valet, first
footman and second footman among the male servants; and then, of course,
the lowest servants -- the housemaid, groom, boot boy, hall boy and
scullery maid. As I explained earlier, with the exception of Felicity,
who was the governess, I fulfilled all of the other roles
single-handedly, at least up until the time they moved into the much
larger home and and hired a butler and housekeeper.


Harper enjoyed playing a game (starting when she was about eight, but
continuing even into her preteen years):


"Today, grandmaid, I will be the lady of the house and you will be my
lady's maid. I want you to brush my hair and then give me a pedicure
using the same nail polish color you used with mommy yesterday."


"Yes, Miss Harper," I would reply with a curtsy, before picking up her
hairbrush.


Later that afternoon, she might say, "Now, grandmaid, you will be my
housemaid and clean my room."  When I was finished, she would inspect my
work, mimicking her mother or Felicity when they inspected my work after
I cleaned the house.


If she was cross with me for some reason, she might say, "Today, you
will be the scullery maid." After I changed into my working maid
uniform, Harper would supervise me as I'm mopped the kitchen floor. She
would also insist that I'd wash the dishes that day by hand rather than
use the dishwasher. Amanda and Felicity would look on approvingly as
Harper warned me to straighten my stockings and would smile as I curtsied
to her in acknowledgment.


Dylan, for his part, liked me to serve as his personal boot boy.


I recall the first time this happened, when he was dressing up to
accompany his parents to the wedding of one of Amanda's sorority
sisters.


"Boot boy, you must shine my shoes before I go to the wedding," he said
to me as I was sweeping the kitchen.


"Of course, Master Dylan," I said, with a curtsy. "Please leave any
shoes you want polished outside your bedroom door and I will polish them
right away."


"No. I want you to polish them while I'm wearing them, just like you
polish my father's shoes. Do it now," he said, pointing down to his
feet.

"Yes, sir," I replied, with a deep curtsy, hurrying off to retrieve my
shoe shine kit. It was quite remarkable watching the entitled
self-confidence of this 9-year-old boy looking down on me I buffed his
shoes from my knees. When I had finished, he examined them carefully,
pointing out an area that I had missed. The irony of this situation was
stunning. A boot boy was typically a young teenaged male, the lowest male
servant in the house, who cared for the boots of his masters and
mistresses. Here I was, 73 years old at the time, at the feet of my young
grandson, working as his lowly servant.


Dylan was particularly captivated by the stories Ryan read to him about
whipping boys. It was not long before I also became Dylan's designated
whipping boy.


That was the next step down as I descended my ladder of shame, one
seemingly without a bottom step.


When Amanda was a girl, it occurred to me that one day I might become a
grandparent. I'd pictured myself reading my grandson a bedtime story or
perhaps giving my granddaughter a horsey-back ride. What I did not
envision, however, was working as my grandchildren's stable boy.


Amanda had been somewhat of a "horse girl" growing up and, in fact, had
been a member of Dartmouth's equestrian team during her freshman and
sophomore years. Growing up in England, Ryan played polo a fair amount.
Therefore, the twins were exposed to the world of horses from an early
age and both embraced it. Both  joined the Hamptons Polo Club's youth
teams, but it was Harper in particular who was horse crazy. She
eventually became a nationally ranked show jumping champion.


Dylan and Harper each received equestrian attire and their own pony as
presents from Jason and Lauren for their eleventh birthday. Ryan and
Amanda had only recently purchased the Downton Abbey-like mansion, which
sat on 3 acres of land and had a three stall horse stable; clearly the
equestrian life was to figure prominently in the twins' futures.


After they rode their ponies for the first time, Ryan said to them,
"Now, caring for your gear is very important. You must keep your saddles
properly oiled and always keep your boots clean and shiny. Why don't you
ask your grandmaid to give your boots a good polish, just to get into the
right habit?"


Dylan was the first to respond: "Boot boy, you heard your master. Fetch
the shoe shine kit."


"Yes, young Master Dylan," I replied with a curtsy as I made haste to
obey his command.


Amanda and Ryan watched proudly as I knelt before their two self-assured
children and strenuously (and superfluously) polished their brand new
boots, setting the precedent for any future times they were worn. I, of
course, also assumed responsibility for cleaning the stalls of the
ponies, cleaning Dylan's and Harper's riding jackets and breeches,
washing and oiling their saddles and bridles, washing their horse
blankets and saddle pads, wiping down their helmets and placing their
dressage whips in their racks. I was later given a sort of boot
black/stable boy hybrid uniform to wear when working in the stable. The
humiliatingly juvenile attire consisted of a light tan shirt, dark tan
overalls that came down to my knees and either brown knee socks or white
silk stockings and black shoes with a large, silver buckle.


Becoming Dylan's whipping boy was quite another matter altogether. I
guess, technically, I was Harper`s whipping boy as well, although she
rarely got into trouble. Ironically, the genesis of the idea of using me
as a whipping boy came in the aftermath of Dylan breaking a very
expensive statue that Amanda had purchased for the huge entrance foyer of
their new mansion. He and Harper were twelve at the time. Amanda was
quite furious with Dylan, and explained to him that he would need to be
punished to make sure he understood the importance of being careful while
playing in the house, where Amanda had accumulated a lot of expensive
furniture and artwork (including Alesia's portrait of me dressed as a
young circus acrobat). No doubt recalling how humiliated she felt when I
spanked her after she broke the Chihuly vase when she was 12 years old,
Amanda told Dylan that he would be grounded for a week.


He replied, "I would much rather be spanked and get it over with."


Amanda was surprised and tried to explain to him that a spanking was
quite humiliating, so it would be preferable to be grounded. However, in
the face of Dylan's truly remarkable persistence (his stubbornness was a
distinctive character trait from an early age), Amanda eventually
relented. She asked Ryan to administer Dylan's spanking behind closed
doors in his bedroom to minimize his humiliation.


However, having won his first concession, Dylan immediately said, "But
father, you have told me many times that young princess and nobles are
privileged and are entitled to have whipping boys to take the punishment
for them. And you told Harper and me that we are high born. Isn't that,
so?"


Ryan looked at Amanda somewhat sheepishly, and said, "It is true that I
have told them that several times. I do think it is important that we be
consistent."


"But do you think he will really learn his lesson if he's not the one
being punished?", asked Amanda.


"Well, the whole concept of the whipping boy is that the young noble
does not repeat his transgressions because the whipping inspires
compassion on his part, and he doesn't want to see his whipping boy
suffer again."


"I'm not so sure about that," said Amanda. "Besides, who is going to
be his whipping boy?"


"The boot boy, of course," interjected Dylan, who had begun to mimic
his father's affected British accent (in contrast to Harper, who bore a
close physical resemblance to Lauren and sounded like her mother).


"Well, there would be some poetic justice in father being punished for
breaking an expensive piece of art, wouldn't there, father?"


"Yes, Miss Amanda," I replied with a curtsy.


 It was somewhat amusing (if also distressing) to hear Ryan speak of
compassion. Disingenuous, I believe, is the correct word.


"It certainly would be much more appropriate for father to suffer that
humiliation than any child of mine. So be it. But you have to promise me,
Dylan, that you will look into the eyes of your grandmaid as he is being
whipped, and to try to feel his pain, so that you will be more careful in
the future."


"I promise, mom."


And that was how I came to receive my first punishment (though far from
my last) in the presence of Dylan and Harper. In the past, they had often
seen me emerging from a room after receiving my weekly maintenance
spanking or some other correction from their father or Jason. The amused
expressions with which they regarded me on these occasions left me little
doubt they knew perfectly well what was going on behind closed doors;
they may very well have even heard what was going on (as hard as I tried
to make as little noise as possible, I sometimes still did cry out). But
that afternoon in the living room was the first time they witnessed my
chastisement first hand.


Ryan decided that "six of the best" with the cane would be more
appropriate than a spanking. I was ordered to bend over a chair as Ryan
swooshed the cane theatrically. He then pulled up my skirt and tapped the
cane against my panty covered bottom as Amanda and Harper looked on.
Dylan positioned himself on the other side of the chair to look into my
eyes I was punished. His expression was rather blank; I really did not
see any empathy there, and in fact, detected just the hint of a smirk on
his lips as the first blow struck.


I wish I could tell you that I was unaffected by this new humiliation.
But the shameful truth of the matter is that I felt my cock throb within
its prison, both during the caning, and for the 30 minutes I stood in the
corner, nose against the wall hands clasped behind my back, after its
conclusion. But at least my dress, my cage  and my position concealed my
arousal from the others. I had truly learned to be grateful for small
favors.


I remember sincerely hoping that Dylan had learned his lesson.


He learned something all right, but not what I was hoping.


Meanwhile, there was this whole other side of my life -- of my
subjugation -- that was going on in parallel, under Lauren's and
Jason's roof. By the time the twins had turned four, I had begun
splitting my time more evenly between Lauren's and Jason's mansion and
Ryan's and Amanda's house. The split then became roughly 40% at the
mansion and 60% at the latter, with variations, depending on what was
going on at the time. For example, after Felicity returned to the UK
around the time that Amanda and Ryan bought their own mansion in
Amagansett (when the twins were 10 years old), I probably spent 70% of my
time working there until the new butler and housekeeper were hired.


I continued to spend two weeks each summer in Virginia working as a maid
in the house of my former sister-in-law and her family and working in my
former nephew's home services business, until I turned 65. I say "home
services," because I worked strictly as a maid inside customers' homes
while Ethan, Reece and Tommy did their landscaping. The boys had all
graduated high school by my third summer in Virginia, but were content to
carry on in the business; college wasn't even considered as an option. I
won't bore you with cataloging the additional indignities I suffered on
those trips, as they were similar in nature to what I have already
described.


Jason surprised everyone when he resigned from the law firm ten years
ago. Up until that time, he continued to send me for a week each year to
Alpine, NJ in a futile attempt to satisfy Elliott Larson's (in fact,
insatiable) lust for revenge. Larson continued to be Jason's biggest
client until the end. And he continued each year to push the limits in
his treatment of me, without violating them. Suffice it to say that I
endured more pony play at the hands of his children, more humiliating
parties involving still other past litigants I had defeated in court,
more brutal massages by Andre and more degrading games with Kendra and
Sabine (at least until my last visit, as Kendra finally divorced the
loathsome creature).


As I mentioned, Jason and I had both been English Literature majors as
undergraduates and both of us had harbored literary ambitions when we
were young men. Both of us went into the practice of law not because of
any great love for the legal profession but rather because of the money
-- and the power. By the time Jason retired from the firm at age forty,
he and Lauren were probably worth close to $45 million (given how the
mansion and my former stock portfolio had appreciated in value, together
with Jason's additional high earnings as a partner). Therefore, he had
the luxury of being able to try something that he, like me, had always
wanted to do: become a professional author. And he ended up being very
successful at it, achieving fame and still greater fortune.


Yet another victory he had over me. Oh well, at least I got to be his
unpaid research assistant...oh, and not to mention, the vanquished foil to
his triumphant protagonist.


So, did I live vicariously through him? Maybe a bit, yes.


The title of Jason's first, and best known, memoir was "He Cuckolds to
Conquer: A True Tale of Revenge, Dominance and Submission." The title
was a play on the title of the 18th century comedy, She Stoops to Conquer
by Oliver Goldsmith. While the play was well known among English majors,
I had argued that it was too unfamiliar to a wider audience to be a good
choice. I was obviously overruled, and, esoteric or not, the title
certainly didn't in any way detract from the popularity of the book. It
ultimately spent 27 weeks on The New York Times' bestsellers list.


The dust jacket of the hardcover edition and the cover of the paperback
edition featured another original work of art by Alesia. As a retirement
gift for Jason, Lauren had commissioned Alesia to do a modern
interpretation of Carl Heinrich Bloch's Samson and the Philistines, aka
Samson in the Treadmill. The painting shows a chained, muscular Samson,
wearing nothing but a blue loin cloth, being forced to push a treadmill
on which is seated a smaller man (presumably a Philistine) who is holding
a long stick with which to beat or prod the captive Samson. Two other
Philistines stand nearby, smiling at Samson's humiliation.


In Alesia's interpretation, it is I, of course, who am Sampson and it is
Jason who is the seated Philistine wielding the stick. She painted the
other two figures just as they appeared in the original. I was 72 at the
time, but am proud to say that my buttocks, back and legs looked like
those of a younger man. However, in an inverse of the original, it was
the seated man who was the muscular one and Sampson, who, while fit, was
decidedly not muscular -- nor young and virile either. Jason and I spent
hours modeling for this painting (although I far more than him); Lauren
even had a treadmill of the kind depicted in the painting reconstructed
in the mansion's garage. At least my erection was not visible in this
work (another small favor, I suppose).


I believe that this painting helped boost the sales of Jason`s memoir,
not only because it was eye catching, but because of the artist's
growing fame. A year after Jason's book came out, Alesia had a very well
received retrospective of her work at a prestigious Soho art gallery. The
Philadelphia Museum of Art loaned the gallery the original Il Saltimbanco
to display next to her portrait of me as the acrobat and the National
Gallery of Denmark in Copenhagen loaned the original Sampson and the
Philistines to display next to her portrait of me as Sampson, along with
several other works by Alesia.


This included one other stand-alone painting involving me that was
commissioned by Amanda as a present for Ryan for his 30th birthday : a
picture of the Roman emperor Valerian (me) being humiliated by the
Persian emperor Shapur (Ryan) after being captured on the battlefield.
There are several classical paintings and reliefs that depict this event,
usually showing Valerian on all fours with Shapur stepping on his back to
mount his horse. This particular picture was not presented next to an
original, because Alesia did not think the quality of any of the
originals was worthy of imitation. However, she did take her usual
whimsical liberties in reinterpreting the scene -- namely, Valerian was
dressed in a maid's uniform and Shapur was dressed in equestrian gear,
with tight breeches, boots, and a riding crop. As you can probably
imagine, modeling for hours in this pose with Ryan's boot upon my back
was no day at the park (Ryan's horse also didn't like to stay still for
long). Dylan and Harper were particularly fond of this life-size
painting, which hung prominently in the main living room of the
Amagansett mansion.


On the exhibit's opening night, I served drinks and hors d'oeuvres in
the same uniform I was wearing in the Valerian painting -- along with
waiters and waitresses from Olivia's catering company -- to the 100 or
so guests invited. Among these were several partners from my old law
firm, Eddie Bolson, Elliot Larson, Penny, Dustin, Kyle & George, Samantha
& Alyson, Paolo, Shyla & Rebecca and, of course, Jason, Lauren, Ryan,
Amanda, Harper, and Dylan.


I thought it was possible that I may have set the Guinness World Record
for curtsies in a 24-hour period that evening.


If Alesia's cover art helped Jason's book fly off the shelves (or into
the Kindles), the mostly glowing critical reviews didn't hurt either.
Here are a few excerpts (sources omitted) from the back of the dust
jacket:


Praise for "He Cuckolds to Conquer":

 *  The fascinating real story behind the tabloid headlines. Collins
    writes an enthralling, brutally honest account of how he brought one
    of the most powerful and feared lawyers in the country to his knees
    -- quite literally --to be with the woman he loves.
 *  Collins has given us the most compelling and insightful account yet
    of the mainstreaming of the cuckold lifestyle in modern American
    society. A book that will appeal equally to sociologists and readers
    of romance novels.
 *  An absorbing read from start to finish, "He Cuckolds to Conquer" is
    much more than a kinky tale of cuckoldry and sissy maids; it tackles
    the universal issues of revenge, karma, love, and possibly even
    redemption.
 *  "He Cuckolds to Conquer" has it all-- part love story, part office
    intrigue, part multigenerational family epic, part kinky erotica.
    There's a little something for everyone in this unforgettable book.

I honestly thought that much of the praise for the book was overblown.
However, there's no question that Jason is an excellent writer. The book
was, by and large, an accurate account of what happened  -- much of which
I have shared with you here.

One notable exception is that Jason was less than fully honest in
explaining the circumstances of how I came to enter my state of
subjugation. He obviously didn't want to expose himself or Lauren to any
legal repercussions associated with what was, in fact, blackmail and
extortion (although the statute of limitations had probably ended).
Rather, he described my capitulation as largely voluntary, something I
chose to do because it was a unique opportunity to live out my submissive
fantasies and to redirect the trajectory of my life.


If you recall, what really happened is that Jason secretly filmed me
dressed in a cheap maid's uniform that Lauren had cajoled me into
wearing as I played the part of her submissive servant. He then
threatened to secretly share the tapes with everyone at the firm as well
as my clients, unless I immediately agreed to nullify Lauren's and my
prenup and transfer all of my assets into her name. Fearing the imminent,
ignominious end of my career, in a moment of weakness, I fully
surrendered to his demands.


By contrast, in Jason`s book everything happened the same way, except
that there was no need to cajole me into putting on a maid's uniform, no
hidden cameras, and no overt threats of extortion. The two of them simply
confronted me with the reality that they had been having an affair; the
reality that I had been woefully inadequate as a husband, father and
lover -- a failure as a man; the reality that I had been an abusive, even
tyrannical boss; the reality that I was wearing a maid's uniform, and
therefore must be deeply sexually submissive; the reality that this
situation eventually would likely become known by my colleagues, which
would deeply harm -- if not end -- my career. And then their offer that I
could live out my submissive fantasies, that I would have a chance to
redeem myself to some extent through my submission and service  -- and,
crucially, that I would not be alone. I could stay on in Lauren's and my
daughter's s life -- true, in a radically altered capacity -- if only I
would agree to a transfer of power. A transfer of wealth. A chance to
start over. So simple.


But, again, except for that -- important details, to be sure, but ones
that accounted for only two days of our long story -- everything else
Jason revealed in the book about what happened was accurate. Even the
part about not being alone and a chance to redeem myself.


Could I have spoiled things for Jason, by telling the truth about what
really happened? Perhaps. But it's not clear that anyone would've
believed me. And what would I have accomplished by it? To be kicked out
of the only home I had known for the last 30 years, as I was approaching
the age of 73? To sever my relationships with the four people --
actually, with Harper and Dylan, now six people --who had become
virtually my whole world, my masters, my owners?


Perhaps a stronger person could've done so, but not I. So, I kept my
mouth shut. Or corroborated Jason's version of events. As I'm sure
Jason had zero doubt I would.



Following the release of the book came the obligatory book tour. Jason,
of course, made me accompany him on the tour, which included readings,
signings and speeches, mostly at edgy, urban bookstores in seven or eight
cities. I was always attired, on these occasions, in one of my formal
serving uniforms, standing submissively off to the side at attention as
Jason played to the crowd. Sometimes I even served refreshments to those
standing in line waiting for their copies to be autographed (I was never
asked to sign them).


The humiliation I suffered, as I'm sure you can imagine, was intense.
However, it was exceeded by what came later. First, the podcast. Then the
television appearance on The Gary Oxtail show (it took a while for a true
successor to Jerry Springer to emerge on the scene, but America finally
found him in Oxtail). Then, finally, the documentary film about our life.
Well, I shouldn't say "finally," because Jason later wrote a couple of
follow-up books. But those were more generally about cuckoldry, BDSM,
power transfer, etc. and did not focus so much on us, on me.


The studio audience at The Gary Oxtail show was filled with young and
middle-aged women for the most part, a few men as well. Oxtail devoted
half of the show to us (truncating the paternity test portion of the
show). Jason was seated next to Lauren as I stood behind them in my
uniform. A couple of moments stand out as I recall those mortifying 30
minutes that seemed like three hours:


Oxtail (smug smile on his face throughout): "What do you call your
maid?"


Jason: "Usually, just Jenkins. Lauren calls him Gregory."


Oxtail: "Does he do any tricks?"


Jason snaps his fingers and points to his feet. I curtsy, drop to my
knees, remove his shoe, and begin massaging his foot.


The crowd applauds, many laughing or covering their faces in surprise.


And later:


Oxtail: "Is he locked up now?"


Jason: "Show him, honey."


Lauren, somewhat shyly, extends her right bare leg, and shakes the chain
on her lovely ankle. More laughter from the audience.


I knew Amanda, Ryan, Dylan and Harper were watching from home, along with
countless others.


I remember thinking to myself, "If this is my fifteen minutes of fame,
it's way too long."


Jason's five-episode podcast was published the year after the book. The
documentary film came out two years after that, shortly after I turned
75. It was filmed largely at the mansion, but a few scenes were also shot
at Amanda's and Ryan's Amagansett mansion, at Forrest's and Jane's
home, and there were even couple of shots of the bathrooms and conference
room of my old law firm's offices-- just so all the viewers wouldn't
have to use their imaginations in picturing the various places I had
cleaned. Nothing is left to the imagination anymore. Indeed, I sometimes
wondered why Jason didn't make it a 3-D film so the audience could use
their 3-D glasses to see the fine grains of the hardwood floors I waxed
(maybe even a scratch and sniff card to smell the Murphy's Oil Soap).


Jason produced the film, but shrewdly hired an attractive 32-year-old
female director, Jade Illis, who also served as narrator. While at NYU
film school, Jade earned money by being a part-time dominatrix, and at
5'9", with her long legs, black hair, ample (though not excessive)
bosom, and a supremely self-confident demeanor, I have a little doubt
that her former clients would've been just intimidated/excited by her
today as when she was undergraduate (if not more so). She had directed
other acclaimed documentaries, exploring different aspects of the BDSM
scene and other unconventional lifestyles. Her favorite film, perhaps not
surprisingly was Grey Gardens, the 1975 documentary about the eccentric
recluses Edie Bouvier Beale and her mother, Edith, on their Long Island
estate.


Jason's and Jade's film had a conversational style, with Jade talking
to Jason and others (even to me sometimes), asking questions about past
events (such as the garden party, Jason's retirement party, Alesia's
art gallery opening, etc.), family dynamics, how we felt about certain
things, etc. Interspersed with the interviews were filmed sequences of
new events taking place while the film was being made.


These included Jason putting me through one of my exercise sessions, he
wearing his usual equestrian gear and me in my usual tights. We went
through all of the same motions as I have previously described, including
him tapping my balls with his riding crop as I rested and me licking his
boots at the conclusion (I will at least say that he went easier on me as
the years went by, taking into consideration my age). Jade also filmed me
receiving a maintenance spanking as well as a punishment spanking. I
stood in my usual penance position after the latter, my erection visible
through my lime green tights -- now memorialized on film for the ages.


The new contemporaneous scenes also included me cleaning Forrest's and
Jane`s home followed by Jane's critical inspection of my work. As Jade
filmed me cleaning, she interviewed Forrest, Jane and Jason. They
discussed the lies I had told about Forrest having an affair as a way to
undermine his position with his clients back when I was in a power
struggle with him to become managing partner of the firm.


Jane said in the film, "Even though Jenkins has been cleaning our house
for many years now, and I've seen him humiliated countless times, I
still have not forgiven him for the lies he told about Forrest. I enjoy
seeing him humiliated as much today as I did that first time at the
garden party when his status was newly exposed. Remember that night,
darling, when he knelt down on the patio to massage your feet for the
first time, how I emptied a bag of rice on the ground first, and made him
kneel on the grains?" She and Forrest laughed at this fond recollection.


Predictably, after my cleaning, Jane found a couple of tiny hairs on the
floor of the master bathroom (did she use a magnifying glass?, I had to
wonder). After I draped myself over Forrest's knees, Jade had the
cameraman zoom in on the two tattoos on my buttocks as Forrest's hands
reddened them. She then directed him to pan the camera over to Jane's
face so the audience could see her satisfied smile. My spanking was
followed by me standing in the corner, holding a quarter against the wall
with my nose for 20 minutes. Thirty seconds of this on film got the
message across.


Lauren and Amanda took Jade and her film crew through the two mansions,
discussing and filming Alesia's artwork as well as all of the wedding
photographs that featured me in positions of clear subservience to my
owners. There were additional family photographs that they filmed --
including a family portrait of of Amanda, Ryan, Dylan, and Harper taken
two years earlier when the twins were eleven. The four of them were
formally dressed, Ryan and Dylan in suits, Amanda and Harper in dresses.
I could be seen standing behind them in my formal serving uniform,
holding a serving tray with four soft drinks.


The most notable new event that Jade's cameraman filmed was the twins'
13th birthday party. Dylan and Harper had each invited roughly 15 of
their boyfriends and girlfriends, all affluent young teenagers like
themselves. The party took place around the huge pool at the Amagansett
mansion. Because of the large number of guests, Ryan and Amanda had asked
Paulo and Shyla if they could borrow Rebecca to assist me in serving the
demanding teens.


Poor Rebecca was now 35 years old and still the cuckqueaned maid to Shyla
and Paulo. Shyla and Paulo were not married, and apparently Paulo still
held it out to Rebecca as a possibility that they would one day be
together as a married couple. I concluded that she must really be in love
with Paulo to still continue to think that could be a possibility. Or,
who knows, perhaps she really did enjoy being the submissive cuckquean.
At some point, the lines get blurry -- as I well knew. In any event, it
was clear that Jade was quite fascinated by Shyla, Paulo and Rebecca; one
could almost see the wheels turning in her head about her next project.


I'm sure that most if not all of the young birthday party guests were
aware of who I was. Several had no doubt seen me on the Gary Oxtail show.
Dylan and Harper took unconcealed pride in ordering me and Rebecca
around, and in watching their friends do so -- fetching snacks, soft
drinks, sunscreen, towels, their sandals, whatever it was they desired. I
only knew a few of them, so simply addressed most as "sir"or "miss,"
as I curtsied to them.


None of the teenagers, or their parents, had any issue signing a release
to be included in Jason`s and Jade`s film.


It seems that everybody wants to be a celebrity anymore.


There was also a scene shot of me caddying for Jason at my old country
club in a  foursome with his brother, Ryan and Dylan. And a scene of me
giving a foot massage to the Director. Far from trying to hide her past
as a dominatrix, Jade highlighted that part of her resume. After I
removed her pump, she pressed her bare foot against my nose and mouth
and  instructed me to inhale deeply before beginning the massage.


Many documentary filmmakers like to keep an objective distance from their
subjects. Jade clearly did not fit into this category.


The documentary won several awards at a number of edgier film festivals
and did fairly well at the art house box office and, better still, on
streaming. Indeed, there were increasingly few people in the country who
were not familiar with my singular story following Jason`s media
onslaught. I had gone a long way since that afternoon 21 years ago at the
mansion when Penny, Alyson and Samantha watched Jason put me through my
paces in my exercise session, as a warm-up to my official public outing
at the garden party. Over the years, my level of exposure was
systematically ratcheted up to larger and larger social gatherings, to
front page tabloid stories, to a national television show and then
finally to Jason's potent book/podcast/documentary combination. There is
public humiliation, and then there is public humiliation. I should be
grateful, I suppose, that Jason did not lead me out by collar and leash
at the Super Bowl halftime show.


Meanwhile, my relationship with my grandchildren continued to evolve
since that afternoon six years earlier when I was designated the official
whipping boy. As I mentioned, Harper rarely got into trouble. I can only
recall one beating I received for one of her misdeeds (when Ryan caught
her smoking a joint in the stables at the age of 16). I thought it was
somewhat hypocritical that he was so angry at her for this offense, given
that I had seen him smoke joints with Paulo and Amanda several times in
the past.


Nevertheless, for that transgression, Ryan struck me 10 times with the
the Obedience Strap (another London Tanners Christmas gift from me to my
son-in-law along the way-- it had become something of a tradition), as I
bent over a chair in the family room. Amanda and Dylan watched from
behind as Harper sat on a chair facing me, staring into my eyes for the
ostensible purpose of feeling empathy for me while I served as her
surrogate in the punishment. In contrast to her brother, she did not
smile or smirk at me. I'd like to think that she may have even genuinely
felt a modicum of guilt for what I was going through, or at least some
compassion for me.


Whereas Dylan takes after his father, including having a bit of a chip on
his shoulder, Harper is more self-secure. She is a beautiful --both twins
are, unsurprisingly, very good looking, taking after their parents
--regal, incredibly confident young woman. That includes sufficient
confidence to allow herself to feel compassion for her inferiors. Don't
get me wrong. In our interactions with each other, she certainly leaves
no doubt as to who is in charge. It's simply that I feel from her some
degree of affection towards me, even if it's more the affection a child
has for a long-time servant than for a grandparent. I am willing to take
whatever I can get.


Dylan, by contrast, seemed to take some pleasure in the far more frequent
punishments I suffered on his behalf. Did he go out of his way to
misbehave to see me beaten? I'm not sure I'd go that far. However, he
certainly didn't go out of his way to behave in order to prevent me from
being punished.


There were a few times over the years where I did something, or failed to
do something, that resulted in me being punished in front of the entire
family. By the time he was 15, Dylan began asking his father if he could
be the one to administer my punishment, especially when my lapse involved
him somehow. For example, in preparation for their sweet sixteen birthday
party, Dylan was livid when he found scuffs on his shoes after I polished
them. The truth of the matter was that he was very rough on shoes, even
dress shoes, and I was unable to remove all of the scuffs, even with
vigorous cleaning and buffing. He was insistent that he was now old
enough to cane me. His parents were quite firm, however, that both he and
his sister would have to wait until till they turned 18 before they would
be allowed to wield the cane, strap, or crop against me.


It was therefore somewhat ironic that it was Harper, not Dylan, who was
the first of the two given permission to punish me physically, shortly
after their 18th birthday. This happened only a few months ago, so I
remember it vividly.


As it turned out, it was not Harper who delivered my punishment, but
rather her boyfriend, Chase. Also eighteen, Chase was 6' tall polo
player that Harper had met at the Hamptons Polo Club. While Harper and
Chase rode their horses around the estate, I had been ordered to change
into my pink speedo to wash and detail Harper's Audi. I had already
washed and waxed the car when they returned from their ride, and was on
my knees scrubbing one of the wheels with a brush. Harper went into her
car to look for something, only to discover water dripping all over the
dashboard. It turns out that I had failed to check that the sunroof was
properly secured before washing the car, so a substantial amount of water
had leaked into the interior, in fact causing some permanent (if
cosmetic) damage.


Harper was furious. She brought her parents out to survey the damage.
Lauren and Jason were visiting at the time and were also present, as was
Dylan.


"This is a very serious and expensive mistake. What do you think,
honey?", Ryan asked Amanda.


Amanda replied, "I think it's time. She's an adult now. Harper, you
have our permission to punish your grandmaid as you see fit. You know
where your father keeps his canes and straps."


"Thanks, mom. But I want Chase to whip him with his riding crop. I want
it to really sting. My car will never be the same."


In short order, I was ordered to bend over and touch my toes in the
driveway. Harper stood next to Chase, both wearing skin tight jodhpurs,
as he swooshed the crop. I looked between my legs at my regal
granddaughter, as she expectantly waited for her strapping, young
boyfriend to teach me the error of my ways. Here is a picture of her
taken about a year before the day in question:


Without warning, Chase struck the first of ten blows across my
speedo-clad backside. It did indeed sting, quite sharply. On the sixth
blow, I dropped to my knees, before righting myself. When it was over, I
turned around to see the three generations of Lauren, Amanda and Harper
passionately kissing their men. It seems that the titillating effect of
watching a young virile male dominate an older, weaker male remained very
much intact for the women of this family.


Ryan had freed me from chastity that morning to clean myself and had then
gotten distracted, forgetting to lock me back up. So, as in the old days,
I felt my cock rise as I stood in my classic penance position beside the
Audi and then felt the shame wash over me as I stared down at the pink
tent, visible to all.


And so, I had come full circle. As I stood there with my family gathered
round, my thoughts returned to that day 21 years ago when Jason punished
me in the sitting room for getting Amanda's drink order wrong. My long
story ends much as it had begun. Were the scales of karma now finally
balanced? I think not. But at least they weren't as lopsided as before.


I had made some progress.