Date: Sun, 3 Dec 2023 00:14:01 +0000
From: Clarice
Subject: Lawyer2Maid

"Mom, I'm curious. Why don't you ever punish dad?, asked my daughter,
Amanda, of my wife, Lauren.

"Oh, honey, I give him a few strokes of the cane now and again, but it's
just so much more efficient to have Jason do it. He hits much harder."
The two of them grinned at each other.

Amanda replied, "I think the real reason is that you simply enjoy
watching Jason administer the punishment," Amanda laughed.

"I must confess, there is something titillating about watching a virile,
muscular, young man, physically dominate an older, weaker man, especially
a pathetic specimen like your father."

"I can't argue with you there, Mom. Especially when it's so well
deserved. There is just something so...so primal about it, isn't there?"

"No question for me. But is it uncomfortable for you to see your father
treated this way?"

Amanda said icily, "Not in the least. He may have impregnated you, but he
has never been a father to me. He was always so focused on his stupid
job, he never had any time for me. And he was a bastard. Remember on my
12th birthday party when I broke that Chihuly vase and he pulled down my
skirt and panties and spanked me right in front of my best friend, Mia,
and that boy I had such a crush on? I will never forgive him for that."

"I remember, honey. It was dreadful."

"And then when I was 17 and scratched his precious Porsche, he made me
drive an old Subaru when all of my friends were driving nice cars. It was
humiliating."

"I know, sweetheart. I tried to talk him out of it, but you know how
stubborn he is--or was, I should say."

"Well, at least he has lost some weight. The diet and Jason's exercise
regime appear to be working."

"They better be," said my wife. "There's nothing more unattractive than a
fat maid. I'm still thinking of making him wear a corset. I will say that
his legs have gotten firmer. He actually doesn't look too bad in his
stockings." They both snickered.

At that moment, I was in one of the sitting rooms of what until recently
was my palatial mansion in East Hampton, draped across the knees of Jason
Collins, my former law firm junior associate, and Lauren's lover. Jason
is 29 years old. My name is Gregory Jenkins, and I am 61 years old. I
took early retirement as the managing partner of our law firm a few
months ago, not under the circumstances I had envisioned. As you can
tell, also in attendance on that afternoon was my wife, Lauren, age 40
and my daughter, Amanda, who had recently turned 21 and was home for
spring break during her junior year at Dartmouth. To paint the picture
more fully, Lauren somewhat resembles the actress, Aubrey Plaza, and my
daughter looks not unlike slightly younger version of Anya Taylor-Joy, in
other words, both knockouts. Jason, or master, as he is now known to me,
looks like a slightly more ripped version of the actor Theo James.  As
for me, I was about 5' 9" tall and still had thick hair, though almost
entirely gray when not died. I was still somewhat flabby with a bit of a
paunch, but Jason's efforts were starting to have their desired effect.

The two women were dressed elegantly in short skirts, stockings, and
heels, accentuating their long, lovely legs. Jason was dressed more
casually in tight fitting jeans and a tank top. As for me, I was wearing
nothing save for a pair of nearly sheer black pantyhose and a pair of
nipple clamps, hanging down off my chest from my position on Jason's lap.
I was being punished for having served my wife and daughter two vodka
martinis, when Amanda had in fact ordered a gin martini. In addition,
when informed of my error, I carelessly spilled the rejected drink all
over my maid's uniform, which I was instructed to promptly remove.

As the managing partner of a prominent, boutique litigation firm in
Manhattan, I had been used to being the oldest person in the room.
However, in my profession--where I had achieved something of a celebrity
status as a ruthless litigator and tyrannical boss--I was generally in
control of the room. Quite a contrast to the situation in which I now
found myself.

"Amanda," said Jason, "since you are the offended party, it's for you to
decide how many strokes of the strap your father here shall receive."

"Please, Miss Amanda, I am truly sorry."

"Well, you will have to learn to be more careful. Twenty should suffice,
Jason."

Hearing this number, and familiar with Jason's technique, I groaned and
squirmed on his lap.

"Stay still, Jenkins," he said, grabbing my balls firmly through my
pantyhose.

"Yes, sir" I hurriedly replied. Jason began vigorously administering my
correction, much to the delight of his audience. I was in tremendous pain
by the 10th stroke but, tears in my eyes, knew better than to complain.
Upon completion, Jason pushed me roughly onto the floor.

"Oh, look Mom, we can see his red ass through his pantyhose. I guess they
don't offer much protection."

Jason said, "Jenkins, now get the ladies their correct drinks and a
scotch for me. Do you need for me to write it down for you so you can get
it right this time, you dimwit?"

I couldn't help but resent this questioning of my intelligence. I
graduated second in my class at Harvard Law and scored a perfect 180 on
my LSAT. Jason, in contrast, was 9th in his class at NYU, with only a
score of 169 on his LSAT. Frankly, he was a borderline hire.
Nevertheless, I had to admit that, over the last six months, he had
outmaneuvered me in the most consequential of ways.

Upon returning with the drinks, I was instructed by Master Jason to stand
in the corner with my hands behind my head, and my legs spread wide.
Looking down at my wife's shoe dangling from her nylon clad foot, I soon
felt myself getting hard despite my best efforts to quell it.

Amanda giggled and pointed, saying, "Ew, look, daddy has a stiffy."

Hearing these words, my cock twitched still higher, growing the tent in
my hose.

Lauren said, "No one wants to see that, Gregory. Turn away from us, and
stand in the corner."

Jason resumed control of the situation, roughly pushing me into the
corner, and ripping off my nipple clamps as he did so. This resulted in
searing pain in both of my nipples.

"Jenkins, nose to corner, hands behind your head. Stand on your tippy
toes."

I could last about 90 seconds on my toes before my 61-year-old calf
muscles started trembling in pain. Every time my heels touched the
ground, Jason struck my ass savagely with the strap.

He said, "This is ironic, Jenkins. When you ran the firm, you would
berate me publicly if a single syllable in a deposition summary was
misplaced. You routinely had me and the other junior associates work 15
hour days, even when it was unnecessary. You'd verbally humiliate the
paralegals if there was a single word misspelled in 100-page document.
You always said you were keeping us on our toes. Well, now, I'm literally
keeping you on your toes, aren't I?"

"Indeed, you are, sir," I answered.

During this 30 minutes of torture, I reflected on how I had come to this
place. It is important to understand that I definitely was not one of the
typical passive beta males who end up as submissive cuckolds. I have
always been in an unambiguous Type A personality, an overachiever,
headstrong, determined to vanquish any competition to get ahead. I was a
textbook asshole, and proud of it. I was that guy who is habitually rude
to waiters and waitresses, cashiers, country club staff--anyone in a less
privileged position than I. But I was rude to the more privileged as
well, believing I was genuinely superior to just about everyone. I guess
I was a little under endowed in the cock department, and perhaps
therefore felt the need to overcompensate in other areas --drive the most
expensive car, have the biggest house, have the prettiest woman on my
arm. I became the managing partner of my 30-partner firm not because I
was respected or well liked, but rather because I was the biggest biller
and threatened to leave if I didn't get the top job. Machiavelli like, I
neutralized my one serious rival, Forrest Johnson, by undermining his
relationship with a key client through innuendo. I had even earned the
public nickname, Gregory "the Viper" Jenkins, for my ruthlessness both in
and outside the courtroom.

I was so focused on getting ahead in my career that I married and started
a family relatively late in life. Lauren was only a kid when I married
her. She was beautiful, but I paid scant attention to her aspirations and
needs (beyond the purely material ones). We did play occasional games in
the bedroom where I liked to reverse roles, and treat her like my
imperious queen, kissing her feet, and so on. I really found this as a
way to loosen up and relieve the stress I felt from being constantly in
charge. Even on these sporadic occasions, I would top from below and
would act like my usual prick self the moment I orgasmed. I was always
distant with Amanda, paying more attention to her when she annoyed me
than at any other time. Lauren had her when she was very young, and they
have always been close, more like sisters in many ways.

It was this periodic indulgence of mine of playing the submissive that
led to my downfall. One afternoon, Lauren toyed with my cock, cajoling me
to wear a cheap maid's uniform that she had bought at the Spirit
Halloween store or someplace like that. I finally agreed to play along
and put it on. It barely even fit me and I looked ridiculous in it. It
was a far cry from the carefully tailored maid's uniforms I wear today
(Lauren and Jason make me use the same tailors I had used for years for
my power suits), I spent the next couple of hours serving her drinks and
dinner, scrubbing the kitchen floor on my knees under her direction,
licking her high heels, etc. It was amusing for a while, but I had had
about enough of such nonsense when suddenly I got the shock of my life
when Jason Collins emerged from behind our pantry door.

"What the fuck?", I shouted.

Lauren said, "Cam down, Gregory. Jason and I have been lovers for the
last six months, and you are too clueless and self-absorbed to have even
have noticed."

Then Jason took over: "This has taken quite a bit of planning on our
part, Jenkins. We have hidden cameras throughout the house. Let's all
take a look at the videos, shall we."

Stunned, I sat down and watched Jason replay what were surprisingly
high-quality videos of me playing the sissy maid in my ridiculous get up.
It was all around an absurd situation.

"So, here's the deal, Jenkins," said Jason. "Tomorrow we will all go to
my friend's law office. He is an estate attorney, and all of the
documents have already been drafted. You will nullify Lauren's and your
prenup and transfer ALL of your assets solely into her name. Amanda will
be the heir to her estate, of course."

"That is ridiculous," I said. "Dream on," although I certainly did not
feel I was negotiating from a position of strength, attired as I was.

Jason said, "If you refuse, tomorrow, copies of these videos will be in
the inbox of every member of the firm and all of your clients. I have
taken precautions to ensure that the files will be sent anonymously so
that nothing can be traced to Lauren or me. I'm sure Page 6 of The New
York Post will also find the story irresistible. Remember when poor Marv
Albert was fired for getting caught crossdressing and The Post's headline
was 'Marv Gets Pink Slip?'"

"That was hilarious," said Lauren. I had thought so too at the time, but
wasn't laughing now.

Jason said, "I can see the headline now: Gregory, 'the Sissy Maid'
Jenkins. If you sign the documents, I will destroy the files."

The upshot is that I was so mortified at the prospect of such extreme
public humiliation--something that would strike at the very heart of my
public persona and result in the immediate termination of my career--that
I showed up the next day at Jason's friends office, and signed the
documents, which were duly notarized. This capitulation was the greatest
mistake of my life (or was it?), and I have been paying the price for it
every second since. It had not occurred to me that Jason was capable of
being as ruthless as I. For he destroyed the original video files, but
did not destroy the copies he had made. They had me. He had me. Then he
set about to break me.

Much has transpired in the six months since then. Jason moved in to my
former home in East Hampton, sharing the king size bed with Lauren in the
master bedroom, and I now sleep on a cot in the maid's quarters. At the
age of 61, now penniless in my own right and entirely dependent on
Lauren's mercy for a roof over my head, I have limited, almost
nonexistent, options. My performance at the firm faltered after all of
this occurred, and I lost two high profile cases and lost my two biggest
clients. Forrest Johnson saw his opportunity for revenge and began
working to push me out of the firm; once I was no longer feared, I
quickly lost all support, and was forced to retire. My colleagues and
subordinates were openly gleeful about my demise. There was no retirement
party. Hanging out there, of course, were the tapes. I had lost my job,
but was not yet a public laughingstock.  But Jason and Lauren have the
power to change that at will. Using their leverage over me, I was
compelled to begin my advanced studies in humility.

Being the goal-oriented individual I am, I like to think of it as a PhD
in humility with Jason as my doctoral advisor. Since my dressing as a
maid is what enabled Lauren's and Jason's successful extortion, they
decided I would become the household maid. I was fitted for uniforms,
both for everyday cleaning duties and formal service occasions. Lauren
enlisted my daughter Amanda's assistance in carefully selecting my
uniforms (styles, lengths, colors, as well as brands of stockings, height
of heels, etc.) and establishing the very specific behavior and etiquette
that was expected of me. They engaged a private tutor, an older woman who
used to run an old school maid training academy, to teach me all of the
proper service etiquette, including how and when to curtsy, how to
address my superiors, how to serve a formal dinner, how to clean most
efficiently , etc. I was put on a strict diet by Lauren and given a
strict, not to mention intensely humiliating, exercise regime by Jason.
He became my personal trainer. My training offered ample opportunities
for Jason to greatly augment his video library documenting my
emasculation, thus further cementing his control.

So, that's how I came to be standing on my toes in the sitting room
before my wife and daughter, dancing to Jason's tune. Following my 45
minutes of penance, I donned a fresh maid's uniform and stockings, and
began cleaning and polishing every inch of Lauren's 12,000 square-foot
home, careful to ensure that it would pass her or Amanda's exacting
inspection. Over the last few weeks, Jason has introduced a new task I am
obligated to perform. He brings home reams of legal documents from the
office for me to proofread. So, after hours of cleaning during the day, I
now find myself regularly spending several hours in the evening
proofreading -- a mindless task that, nevertheless, requires intense
concentration, as errors result in harsh punishment. Another example of
irony that appeals to Jason's sensibilities: the former managing partner,
now relegated to the bottom of the law firm hierarchy, proofing for his
former associate. So, as I rest my tired feet, I must exert my weary
mind.

I have noticed a distinct shift in my psyche that has begun to take
place. There remains a side of me that continues to feel superior to
those around me, including Jason, and the dichotomy of being in a
position subservient to everyone creates in me deep feelings of anxiety,
resentment and shame (even occasional strings of resistance, although
these are diminishing). At the same time, I am coming to appreciate that
there is a certain symmetry and logic to it all. What goes up, must come
down...the higher they rise, the harder they fall. Clichés exist because
they are grounded in truth. My ascent was impressive, my descent
spectacular. After being an incorrigible asshole all my life, my
intensive humility training is showing me that I do possess some capacity
for feeling empathy and guilt. Stripped of my dignity, I have begun to
feel more acutely than ever before in my life. Is it possible that I need
to genuinely suffer for my life to have any true meaning? Certainly, I
have started to eroticize my subjugation. So, at the age of 61, I have
less power than ever, but at the same time am more of a sexual being than
ever as well. It is complicated.

I never recall having been attracted sexually to men in the past. Nor do
I believe Jason is really attracted to men. But I do know that Jason is
aroused by dominating another man in the presence of women. And I know
that I am aroused by being dominated by another man in front of women,
especially when those women are family members or former employees who
once saw me in a position of authority. Especially when that man used to
be subordinate to me, and is less than half my age. As Amanda put it,
there's something primal about it, I suppose.

The day after my chastisement in the sitting room, I was informed by
Jason that what I dreaded the most is coming to pass: my new status is
becoming increasingly public. A garden party at the mansion has been
planned for the last week in August in which I will be defending my
dissertation in humility before a select group of guests, made up of
former colleagues and subordinates, friends, and family. Between now and
then, the plan is for me to prepare for this event through a series of
warm up events

The first such event occurred the following week. All attendees agreed to
sign a nondisclosure agreement to protect against any potential
reputational damage to my old firm; the reputational damage to me was the
whole point, of course, but it would be limited for the time being.
Invited were three highly attractive young women from my former office (I
always screened out the unattractive ones): Samantha, a junior associate,
30 years old; Penny, a 22-year-old paralegal; and Alyson, an 18-year-old
secretary. Samantha and Alyson are long legged brunettes whereas is Penny
is a petite blonde with a mischievous smile. All three had been on the
receiving end of my verbal abuse numerous times when I ran the firm.

After swimming in the pool, they sat on deck chairs in their bikinis,
waiting for the show to begin. While they may have had some inkling of
what to expect, I'm sure nothing could've prepared them for what came
next.

Samantha, Penny and Alyson had front row seats to see Jason putting me
through my paces as my personal trainer. Jason led me out of the house by
collar and leash into the yard, about 8 feet away from our audience. All
three young ladies gasped, covering their smiling mouths in shock. Jason
was shirtless, wearing skin tight jodhpurs and riding boots, carrying a
cane in one hand and a riding crop in the other. I wore footed gray
tights, nearly sheer, and nothing else save for my collar. Jason began
our routine in the usual way, swooshing his crop three times in the air
before striking my bare back to spur me on. He held the cane up to my
waist, thus settling the required level of my high steps, as I began to
trot in a circle around him. When my knees fell short, he would slash my
ass with the crop, eliciting a yelp from me. Jason favors a split tip
crop called the Motivator, known for the loud noise it makes when it
meets flesh and the sharpness of its sting; it is aptly named.  Next, he
pointed to the ground, and I dropped to do push-ups, something I was
never particularly good at, even when I was his age. Jason tapped the
cane on my ass with modest force each time I raised it. This was followed
by deep knee bends and jumping jacks, all with the encouragement of his
crop or cane. It was over 90°, so it didn't take long before Jason's
muscular torso was glistening in a sheen of sweat.

I heard Samantha say, "Oh my God, I think this may be the hottest thing I
have ever seen."

Alyson replied, "No kidding. I wish they didn't ask me to leave my cell
phone in the pool house. I would love to film this."

I saw their eyes turn to Penny, who looked mesmerized, her fingers
between her legs.

I was permitted two water breaks during our 45 minute sessions. Although
my fitness level had improved over the course of Jason's training the
prior three months, there were still points during the session that
afternoon where my breathing grew labored and my chest burned with pain.
I was permitted to rest lying on my back at Jason's feet, but during
these breaks, he would lightly tap my balls with his crop lest I think of
taking advantage of my brief respite. After I recovered, we would do it
all over again, until the seemingly interminable session finally
concluded. At that point, I collapsed at Jason's feet in my sweat soaked
tights. Upon catching my breath, I crawled over to Jason, as I had been
taught, and, seeing the women's long legs and flip-flop covered feet out
of the corner of my eye, began abjectly, licking his boots. He smiled
triumphantly at the three women. I tried hard to hide the growing
erection I couldn't suppress, but the laughter of the three women let me
know I had failed.

After he decided that his boots were sufficiently moist, I was sent to
shower and change into one of my formal maid uniforms. I then served the
four of them drinks, careful to curtsy to each as I took their orders and
after I handed them their drinks.

Penny, said to Jason, "I wonder if his ass is still warm? May I?"

Jason laughed. "Be my guest."

Penny reached under her former managing partner's skirt, rubbing my sore
buttocks through my hose. "It definitely still is," she giggled, sharply
swatting my ass.

Alyson said to me, "Well, MR. Jenkins, you're not so high and mighty now,
are you?"

"No, Miss Alyson, no, I'm not. I would like to beg all three of you to
please forgive me for my past behavior."

"Shouldn't you be begging from your knees, Jenkins?", said Samantha.

"Quite correct, Miss Samantha," I said, dropping to my knees before her.

"Why don't you show each of our guests how well you have learned to
massage feet, Jenkins," commanded Jason.

I spent the next 60 minutes strenuously massaging the feet of three women
as they discussed office politics with Jason. My only breaks were when I
was sent to bring them fresh drinks, during which time I would rub and
shake my sore fingers and hands. After I finished massaging to their
satisfaction, Penny said to me, "Shouldn't you also be attending to the
feet of your young master?" The three women snickered.

Jason extended his leg and I pulled off one boot and then the other.

"Should I massage with your socks or bare, master?"

"Bare. Start with the left foot."

I removed his sock and began working on his left foot. Meanwhile, Jason
placed his sweaty socked right foot over my face, causing still more
derisive laughter from the women. When he decided that I had spent
sufficient time with his left foot, he slapped my face with it and then
extended his right one to me.

 It was a thoroughly entertaining and unforgettable afternoon for our
guests.

There were a few other such events over the summer, leading up to the
garden party, including serving as a maid at a poker game between Jason
and a few of the other male associates who I used to bully and belittle.
There was much groping and slapping of my ass on that occasion as well.
Humiliatingly, I found myself getting hard that night too, even with no
women present, causing me to wonder if all of my emasculation was
affecting my sexual orientation in some fundamental way.

I felt in some ways as if my brain was being rewired, as I came
increasingly to crave the humiliation. Strangely, I started to feel
almost disappointed when the degradation was less than on some prior
occasion; it felt anti-climactic, and almost like a failure on my part.
Perversely, I still felt the compulsion to overachieve, but now, in my
downward spiral, that meant experiencing levels of abasement that were
unprecedented. Maybe that would be freedom? Maybe that would be
happiness?  Or could I be going insane? In any event, if reaching new
lows had become my twisted objective, the garden party did not
disappoint.

Planning for the grand event began in earnest in mid July, including the
careful selection of the guest list. After thoughtful deliberation,
Lauren and Jason settled on the following:

 *  Amanda, of course, and her 21-year-old boyfriend, Ryan, the captain
    of Dartmouth's fencing team, a dual US and British citizen. I had met
    Ryan the prior summer, before so much had changed, when Amanda
    invited him to dinner. He is a tall, good looking kid, but his accent
    annoyed me. Over dinner, I was dismissive of his political views and
    questioned his intelligence, humiliating him by pointing out an
    obvious flaw in his argument. I could tell Amanda with seething, but
    she remained silent.
 *  My sister, Sharon, three years, my junior, and my 31-year-old niece,
    Olivia. I have never been close with Sharon, who resented the bossy
    and condescending way I treated her growing up. But our relationship
    really deteriorated later in life after her husband left her when
    Olivia was only eight. Sharon begged me to help out financially, but
    I refused (even though I was already pulling down close to seven
    figures by then). Amanda has a positive relationship with her aunt
    and cousin. They have since started a small catering company. In
    addition to being guests, they will also be catering the party, and I
    will serve under Olivia's direction.
 *  Joe and Marilyn York, who live nearby in Sag Harbor. Marilyn and
    Lauren are of similar age and close friends. Marilyn has always
    thought I was a sexist pig and a lousy husband to Lauren. Joe is a
    successful M&A attorney and he and I have always been competitive. I
    ultimately earned more than he did, had a bigger house, etc. and have
    always enjoyed rubbing it in.
 *  Amanda's childhood best (and still close) friend, Mia, the very one
    who witnessed me spank Amanda after they broke the vase during
    Amanda's 12th birthday party.
 *  From the office, Samantha, Penny and Alyson were returning as well as
    the three male junior associates I had served at the poker party.
    Also invited were two recently appointed junior partners, one a gay
    male and the other female. Both were named partner after I was forced
    out; although both were excellent attorneys, I had had held back
    their promotions, because I felt both were insufficiently
    differential to me.
 *  Finally, Forrest Johnson, and his wife, Jane, both around 58 years
    old. Forrest is my successor as managing partner of the firm, and
    played a key role in my forced retirement six months ago. As I had
    mentioned, he was my chief rival for the job several years ago. I had
    prevailed by sabotaging Forrest's relationship with one of his key
    clients by insinuating to the client that Forrest was indiscreet with
    extramarital affairs--which had no basis in fact. Jane harbored deep
    ill will towards me because of this.

Meanwhile, earlier this summer, Lauren and Jason began allowing me again
into their bedroom, mainly for the purpose of humiliating me as a form of
foreplay. Jason took to having me fluff him, with Lauren looking on.
After they had sex, I would be called back in to clean up Jason's mess
from my wife. They purchased me a spiked chastity cage. Jason is the one
who put it on me, and, naturally, is my keyholder. Releases are rare and
have to be earned, usually through creative exhibitions and rituals of
abasement. However, I am generally only locked up at night. I have few
idle moments during the day, and Jason and Lauren like to see me go about
my chores with an erection--which I am not permitted to touch or relieve.
Their favored attire for me is pantyhose or tights, and they purchased me
pairs in a myriad of colors and styles (seemed/seamless, opaque/sheer,
ripped, etc.). I, of course, am always required to keep my body shaved
(including regular waxings in the village). They could see that the nylon
rubbing against my cock keeps me in a near constant state of arousal, and
know how shameful it is for me to be seen with my cock pushing out the
nylon, especially by Amanda. It also amuses them to smack my nylon clad
cock and balls (with whatever is handy, but most often with one of the
wooden spoons that seem now to be in every drawer) as I complete my
chores.

It was my responsibility to handwrite the invitations. This was
challenging because Jason had taken to having me write punishment lines
when I make errors in proofreading. The prior day I had been compelled to
write 500 times, "I am careless airhead who can't catch the most obvious
mistake. I must beg Master Jason to correct me," so my hands and fingers
were quite sore.

While each invitation had some degree of customization, the essence was
as follows:

Dear ____,

I, Gregory Jenkins, humbly beg the honor of your presence at a garden
party at the home of Lauren Jenkins in East Hampton, New York on
Saturday, August 27, from 4 to 10 PM.

As you likely have heard by now, since leaving the practice of law six
months ago, I have begun an unconventional, yet transformative
retirement. My former law firm associate, Jason Collins, moved into the
East Hampton residence with Lauren and I, and he has been playing a
central role in the reevaluation of my life that I'm currently
undertaking. There will be a major announcement regarding our living
situation at the party. With Jason's invaluable assistance, I have come
to realize the tremendous damage and pain I have caused my family,
neighbors and coworkers, for the better part of my life, through my
abuse, pettiness, neglect, and sometimes outright cruelty and duplicity.
Under Jason's tutelage, I have been undergoing an intensive education in
the subjects of humility, karma and atonement, heretofore alien to me.

I am 61 years old, with limited time left on this earth. I have reached
the conclusion that, in order to have any chance of peace in what remains
of this life, or in the next, I must endeavor to atone for my abhorrent
behavior. My dilemma, perhaps, insurmountable, is how to atone for 40 to
45 years of terrible behavior in the short time I have left. I have
concluded, with Jason's guidance, that the only possible way to even come
close to balancing the scales of karma is for my remaining years to be
defined by humiliation and service.

All of you who are invited have been victims of my abuse. I beseech you
to do me the honor of actively participating in my public abasement,
which, by necessity, must be immersive, covering all aspects of life:
familial, professional, sexual, domestic, spiritual. I beg you to bring
forth your own creative ideas to the party to help further the
possibility of my redemption. Please understand that the more abject my
humiliation, the deeper my level of service, the greater the chance of me
achieving my goal. I realize it is presumptuous to ask those I have so
harmed for anything, but I hope you can find it in your heart to grant
this humble, deep felt request.

I do believe it will be a unique and cathartic experience for all
concerned.

Sincerely,

Gregory Jenkins


Perhaps not surprisingly, all RSVPs were in the affirmative. No one was
deterred by Jason's requirement of signing a nondisclosure agreement
(this gave me a modicum of reassurance, but I knew better than most that,
NDAs notwithstanding, rumors spread).

The week leading up to the garden party was somewhat of a respite for me.
In anticipation of the inevitable party activities, I was spared physical
punishment, including Jason's exercise regimen, at least until the
morning of the party. That said, I was kept on my feet, and on my knees,
with sweeping, scrubbing, mopping, polishing, and so forth. Meanwhile,
Jason kept a log of any transgressions to be addressed later.

I grew increasingly anxious as the 27th approached. I experienced a sea
of conflicting emotions, ranging from titillation to terror. I knew that
I would be subjected to unspeakable levels of humiliation. As I explained
previously, there was a growing part of me that welcomed the degradation,
even craved it, not only believing it was deserved, but that it was
necessary for my survival. What I wrote in the invitations was not
coerced or insincere. That said, 61 years of feeling superior is not
expunged overnight. There still resided in me a sense that I was being
brought to heel by people less intelligent, less successful, less worthy
than me. In other words, there were still faint flickerings of rebellion
and pride in my psyche. I had not been fully broken. Yet.

I was up early the morning of the party, dressed in one of my formal
service uniforms, preparing breakfast for Lauren and Jason, Amanda, and
Ryan, and Sharon and Olivia. The latter spent the night so as to be able
to get an early start on the catering preparations for the impending
festivities.

Olivia was incredulous to see her once notoriously intimidating uncle
dressed as a maid, serving her breakfast. "I can't believe this," she
said. "Do I really got to tell him what to do, Aunt Lauren?"

"Of course you do, my dear. He is fully at your disposal, except when he
may have other more urgent tasks to attend to. He's going to be busy
today!", laughed Lauren.

I walked over to my niece and curtsied to her. "I am at your service,
Miss Olivia." Olivia laughed gleefully.

I had taken everyone's order and was scurrying around the kitchen in my
high heels, preparing the food. I don't know if it was intentional or
not, but whereas most of the diners were happy with the scrambled eggs
and bacon I was cooking, Ryan asked for his eggs over easy, and my sister
Sharon wanted an omelette. It was challenging to prepare these different
orders, all relatively close together and still hot (indeed, prior to the
last six months, I had barely cooked in my life).

After I served him, Ryan dropped his work on his plate and said, "These
eggs are runny and my toast is cold."

No doubt recalling my slight of Ryan at dinner the prior year, when she
had felt the need to hold her tongue, Amanda addressed me sharply, "You
seem to have some issue with showing proper respect to my boyfriend,
father. Ryan, I would like you to teach him some respect."

She then looked at Lauren and asked, "Is it okay, Mom, or do we need to
keep his bottom unmarked for the party later?"

Lauren said, "It's fine, honey. The big day has arrived, after all.
There's no time like the present."

She turned to Ryan. "I simply ask that you please show some restraint."

Lauren next turned to me and said, "Gregory, fetch the cane and present
it to Ryan."

I curtsied. "Yes, ma'am, right away," and quickly retrieved the cane kept
hanging in the pantry.

I handed it to Ryan and curtsied to him, saying, "Please forgive my
carelessness, sir. Would you kindly correct me?"

A product of the British boarding school system, where he had been a
prefect, Ryan was quite familiar with how do use a cane. He instructed me
to place my arms on the counter and bend over, lifting my skirt, and then
delivered what he referred to as "six of the best." I thought that they
were rather six of the worst, having tears in my eyes after only the
third stroke.

I stood up gingerly when my punishment was complete and said, "Thank you,
sir, for my correction."

Amanda looked at me sternly and said, "From now on, you will address my
boyfriend as Master Ryan, father. Have I made myself clear?"

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

I pivoted to Ryan and, curtsying again, said, "My sincere apologies,
Master Ryan. I shall endeavor to do better next time."

"See that you do," he answered, in what I still couldn't help thinking of
as a pretentious half British accent. Amanda smiled at him and, pushing
up against him, kissed him passionately.

I saw the astonished expression on Olivia's face having just witnessed
this episode. I took a moment to absorb what I had just experienced. I
was a 61-year-old man, dressed as a maid, who had been caned by the
boyfriend of my daughter, a man a third of my age. I was then ordered by
my daughter to address him as master, as she looked on triumphantly. My
humbling appeared to have an amatory effect on the couple, as evident by
their embrace. All of this was witnessed by my niece, my sister, my wife
and her lover, a man who had vanquished me. All of this in the kitchen of
a house where a year ago I reigned as king. How low can a man fall? This
day was to demonstrate that, incredibly, I still had quite a bit further
to go.

After remaking Ryan's breakfast, I began assisting Olivia and my sister
in preparing the hors d'oeuvres that I would be serving later. My niece
took obvious delight in criticizing my efforts and generally ordering me
around.

Around 10:30 AM, I was summoned to the tennis court, where a mixed
doubles match was being planned between Amanda and Ryan against Jason and
Lauren. I've always been a pretty good tennis player, but today I was to
be the 61-year-old ball boy. As they went to the pool house to change
into their tennis whites, I was instructed by Jason to change into my
white tights. Like a ball boy at Wimbledon, I got down on my knees with
my hands in front of me, poised to run with dispatch to retrieve any
errant ball. The welts from Ryan's caning were clearly visible through my
nearly sheer tights. My 61-year-old back and knees aching, I did not run
with the same spastic intensity as a Wimbledon ball boy. As Jason berated
me for my laziness, promising delayed correction, I felt my cock starting
to rise. Nevertheless, I tried to run faster on the hard court with my
nylon clad feet to retrieve balls quickly, mindful of Jason's threat.
Amanda then bid me to bring her and Ryan towels. When she looked down at
my midsection and smiled contemptuously, I wondered if it was physically
possible to die of shame. But, alas, it was not yet noon; the day was
young.


Following the match, I was drenched in sweat, so showered before changing
into one of my working maid uniforms. Olivia put me to work handwriting
the menus to be placed on all of the guest tables set up around the yard.
As I did so, I noticed that already resting on them were smaller versions
of the bells that Lauren, Jason, and Amanda use in the house to summon me
when my services are required. After lunch, there came a moment I found,
especially disturbing. Lauren instructed me to assemble swag bags for the
guests. The contents were simple: a wooden spoon, a hand held punch hole,
and a punch card. Roughly the size of a business card, the punch cards
were to offer a range of options of complementary services -- obviously
to be provided by me--to each guest:
 *  cleaning house/apartment
 *  washing/detailing car/truck
 *  mowing lawn/yard work
 *  cleaning/organizing footwear
 *  foot massages (3)
 *  caddie/ball boy service

The choice was to be indicated by punching a hole next to the selection.
It was the material of the cards that was the source of my distress:
Jason instructed me to cut up my law and undergraduate (Princeton, summa
cum laude) diplomas into squares. When he saw my expression -- I was
still capable of registering shock, apparently -- he said "It's not like
you'll be using them again, Jenkins. Think of it as recycling."

I then changed into my most formal uniform: classic black satin with
white lace trim and apron, shorter than most, with white petticoats and
matching maid's cap, and seamed, sheer black stockings and heels. I was
to greet each guest, thank them for coming, present them with their swag
bag, then escort them to their tables and take their drink orders. During
any rare idle moments, I wish to stand at attention, arms at my side,
legs pressed together, and head slightly bowed.

Unusually punctual, all of the guests were seated by 4:30 PM. Most of the
men wore blazers and dress shirts and the women skirts, stockings and
heels. I spent the first hour or so frantically responding to the near
constant tinkling of bells, serving drinks and hors d'oeuvres. Later,
Sharon and Olivia set up a small bar poolside, as I was called upon to
amuse the guests in other ways.

At roughly 5:30 PM, Lauren rang a bell to get everyone's attention. As I
stood next to her and Jason, she addressed the guests: "Thank you all for
coming and participating in this important event for Gregory and our
family. I say 'family' because we have an important announcement to make.
As probably all of you are aware, Jason moved in here shortly after
Gregory's rather abrupt retirement. He has played a pivotal role in
helping Gregory understand the errors of his way in his unforgivable past
treatment of me, Amanda, and, frankly, all of you present today. As his
junior associate at the firm, Jason suffered more than his fair share of
Gregory's abuse. It is therefore especially fitting that he is the one
who has finally been able to help Gregory understand the concepts of
humility and atonement. He has done a masterful job, and Gregory here, as
you all will see unambiguously today, has been thoroughly mastered. It
likely will not be a shock to any of you that Jason shares my bedroom and
Gregory has moved into the maid's quarters. We are now formalizing this
relationship. Gregory and I are divorcing, and Jason and I will be
married in the spring. Jason, of course, will have full conjugal property
rights -- equal ownership -- with Amanda as the sole heir of our estate.
We have magnanimously decided to allow Gregory to remain in our lives and
living under our roof as the family maid. You will all, naturally, be
invited to our wedding, where Gregory will be serving. Please join me in
a toast to the true love of my life and the new man of this house, Jason
Collins."

This speech was met with enthusiastic applause. Jason and Lauren
passionately kissed. I hung my head in shame.

Next, Lauren, Jason and I made the rounds as a trio, visiting with
different groups of guests. The younger members of my old firm were
seated together around a large table near the pool. In response to my
request in the invitations that the guests bring creative ideas to
advance my humiliation, most bought brought gifts for me, or for Lauren,
Jason and Amanda. The gifts of the young male attorneys from the poker
party were fairly unimaginative: a pair of handcuffs, a butt plug, etc.
The young women who attended my shameful exercise session were more
creative. Penny bought a new riding prop for Jason ("In case you wear
your other one out"); Alyson bought me two customized T-shirts, "Lauren's
Lackey" and "Jason's Skivvy"  ("I thought these might be good for him to
wear when you're out in public, you know, in places where the maid
uniform or tights might not be practical"); Samantha gave me a leotard,
pink tights, and a tutu ("I thought he could entertain you and Jason with
a recital").

The two junior partners who had not yet seen me in my maid's attire
didn't bring presents, but were eager to participate in my humiliation.

The female partner, Jennifer, asked, "When can we try out the wooden
spoons?"

Jason instructed me to bend over and pulled up my dress, inviting anyone
who wished to strike my protruding bottom. Every one of them did, most
hitting me multiple times.

Jennifer said, "I'd like the former managing partner to lie over my knee
so that I can punish him properly."

I curtsied to her and did as she instructed. She struck me with her spoon
12 times, saying "When you held up my promotion, I bet you couldn't have
envisioned this moment, could you, Jenkins?"

I replied, "No ma'am."

Nor could I have envisioned Richard, the gay partner, who I had also held
back, next pulling me across his knees and rubbing my bottom, where the
cane marks from this morning were still visible.

He said, "You poor thing. Look at those welts. You need some relief."

He pulled a tube of skin cream from his pocket and proceeded to rub the
cold cream over my buttocks. He said, "Oh my, I feel something hard on my
leg. He must be happy to see me!"

The group thought this was hilarious. I stood up and thanked him,
curtsying, and pulled up my stockings, ensuring that my seams were
straight.

After I returned with fresh drinks, they began discussing how they
planned to use their service vouchers. Most of the female members
intended to avail themselves of my housekeeping services. One of the men
informed me I would be washing and detailing his pickup truck.

Samantha said, "He's going to polish all of my shoes and boots. I have a
bit of a shoe fetish. My roommates call me Imelda Marcos. Would it be
possible to have a little demonstration of his skills?"

Lauren said, "Of course, dear. Gregory, fetch the shoeshine kit, and show
everyone what you can do."

Returning, I curtsied to and knelt before this young woman who six months
earlier walked on eggshells around me, then carefully polished her high
heeled shoes as she stared down at me imperiously. Not surprisingly,
several others in the group, including two of the men, demanded the same
service.

Once the group of my former subordinates were satisfied with my strenuous
polishing and buffing, Lauren, Jason and I moved on to the next station
in my gauntlet of shame.

Across the pool, were the two more mature couples in attendance, Marilyn
and Joe York and Forrest and Jane Johnson. Both senior lawyers, Joe and
Forrest knew each other professionally and both are also members of the
same Southampton country club where I had a long been a member. Forrest
and Jane were at the bar when Lauren, Jason and I walked up to their
seats.

Joe addressed me first, "Hello, Jenkins. This is by far the best party
you have ever thrown. Nice uniform. I always say, 'The clothes make the
man.' " They all laughed.

"He's really not much of a man anymore, is he?," said Marilyn.

"It's questionable how much of a man he ever was," said Joe. "Jenkins,
you always measured your manhood by how big your house was and how big
your bank account was. How big are they now?"

"My assets are nonexistent now, sir, and I live here at the pleasure of
Mistress Lauren and Master Jason."

"Don't worry, Gregory, you're always welcome in our house -- to clean it.
I'm looking forward to using my coupon," added Marilyn.

"It would be my pleasure, ma'am, and sir," I said, curtsying to both.

"We got you a present, Jenkins," said Joe, handing me a box. Opening it
after my obligatory, curtsy and thank you, I discovered what I can only
describe as the uniform of a British school boy: shorts, a blazer, a
striped tie, and knee socks.

Lauren said, "That's very kind, but we generally prefer to keep Gregory
in more feminine attire."

Marilyn replied, "Oh no, dear, that's not for him to wear here. That will
be his uniform when he caddies for Joe and Forrest at the club."

"That's a great idea, Marilyn," said Lauren

"Perhaps we will have Jenkins model it for us later, along with some of
the other gifts he has received today," added Jason

I tried to envision what it would be like wearing this uniform, carrying
the bags of Joe, or worse yet, Forrest, at my old country club -- seen by
former peers, clients and the staff. The shorts were absurdly short, so
everyone would be able to see my hairless legs, as well as the cane marks
that were typically visible on my upper thighs.

"Well, you certainly have done a remarkable job with him, dear. Have you
considered starting him on hormone therapy?", said Marilyn.

"Jason and I have discussed it, but we don't want him identifying as a
woman. We really prefer him to be acutely conscious that he is an
emasculated, feminized male. That is why we still call him Gregory and
use male pronouns. We believe it heightens his humiliation. Sometimes,
just for amusement, we have him go a couple of days without shaving his
face. Watching him prance around in his tights or uniform with stubble is
pretty funny."

The next thing I know I feel my dress lifted in a hard swat to my ass. I
turned around to see Forrest wielding his wooden spoon.

"Good afternoon, sir and ma'am, may I get you anything?," I said to
Forrest and Jane.

Forrest answered, "Later. I've been looking forward to this visit,
Jenkins. We've been trying to decide which hole to punch. I feel like I
need a test drive, so to speak. Kneel down and massage my feet."

"Of course, sir."

As I began to kneel Jane commanded, "Wait!" She removed a bag of rice
from her bag and emptied its contents onto the pavement around her
husband's feet. I knelt down on the rice, removed Forrest's shoes and
socks, and began to knead his soles.

As I did so, he said, "Hiring Collins was the best thing you ever did at
the firm," looking over Jason, who had walked over to the bar to get
another gin and tonic. "He's a good man. He will make partner early. His
idea for the punch cards with a nice touch. I see the 'H' of Harvard on
the back of mine. I always told you a degree from Yale had more value."

I reflexively thought, "arrogant bastard", before remembering my place
and the bigger picture.

As I continued to attend to Forrest's feet, trying my best to ignore the
rice digging into my nylon covered knees, I saw several of the younger
members of the firm start to move closer to our table. I am sure the
spectacle of their former managing partner, dressed as a maid and
kneeling before their current managing partner, massaging his feet, must
have been too compelling to resist. Jason returned with his drink and
asked Forrest if my massage was adequate.

Forrest answered, "I think Jenkins is finally starting to realize what
types of work are a better match with his talents. You know, Jenkins, the
punishment lines were my idea. After all, you are proofing documents for
MY clients."

I surprised myself by replying, "Perhaps you and Mrs. Johnson should
attend my punishments for mistakes in proofreading, sir. I'm sure Master
Jason would be grateful for assistance in administering my correction."

This marked a milestone. Up until now, all of my indignities had been
imposed upon me by others. This was the first time that I volunteered an
idea to further my own humiliation. I saw Jason and Lauren exchange a
knowing smile, and felt my cock grow still harder.

Forrest replied, "You can count on it, Jenkins."

Penny, listening with the others, asked, "Can I attend too?", and
snickered.

Following the massage, Forrest directed me to remain on my knees, and to
also place my hands on the rice covered ground. He and Jason rested their
feet on my back as they discussed the feasibility of me coming into the
office in Manhattan two evenings a week to perform janitorial duties.

My former subordinates watched and listened intently, no doubt savoring
the prospect of watching the man who used to lord it over them mop floors
and scrub toilets as they burn the midnight oil.

The next stop on our tour was the one I dreaded the most.

Lauren, Jason and I walked over to the table where Amanda and Ryan were
talking with Amanda's childhood friend, Mia. Mia was not as striking as
Amanda, but had a pretty girl-next-door quality. She was home from
college on the West Coast, and today was the first time she had seen me
since I had assumed my new status. It was quite recently that Amanda had
expressed to Lauren her never being able to forgive me for the
humiliating spanking I had given her in front of Mia and her crush when
she was 12. Recalling this, I had a little doubt about what laid in store
for me. Indeed, Amanda and Ryan had both changed into their equestrian
attire, their long legs sheathed in tight, tan leggings and black leather
boots that came up nearly to their knees. Resting against Amanda's
buttoned, black jacket was a riding crop.

"Miss Amanda, Master Ryan, Miss Mia, may I refresh your drinks?", I
nervously asked as I curtsied.

"No, father, we have more pressing business with you. Miss Mia has kindly
bought you a present." Unwrapping the box Mia handed me, I found a
pedicure kit, probably of professional quality, containing a variety of
files, clippers, buffers, pumice stones, soaking solutions and nail
polishes.

Curtsying, I said, "Thank you, Miss Mia. You are much too kind."

Mia said to Amanda, "With practice, I am sure he will learn to be a
wonderful foot girl for you and your mom."

"And for Jason and Ryan," laughed Amanda. "There's no reason why they
should have gnarly toes just because they're men. Perhaps he can do all
four of our feet when we watch movies in our home theater."

"Amanda, have you noticed that your father has badly laddered his
stockings, and his stocking seams are a mess?", said Mia.

I had foolishly neglected to check my appearance after completing
Forrest's massage. So now Amanda had her pretext. No matter; if not this,
she surely would've found something else.

"My sincere apologies Miss Amanda, Master Ryan, and Miss Mia. May I
please be excused to put on fresh stockings?"

Amanda answered sharply, "No, you may not, father. Mia, who witnessed you
spank and  humiliate me nine years ago, will now get the opportunity to
see you punished and humiliated. Go put on the Peter Pan outfit I bought
you for your birthday last month and report back to me. Hop to it."

"Yes, Miss Amanda," I replied, curtsying deeply before scampering off to
the house.

Although Amanda expressed disgust whenever I was visibly aroused in her
presence, I believe she was amused by the deep shame I felt on those
(increasingly frequent) occasions, as she often demanded that I dress in
tights or pantyhose when being disciplined. My punishment tights, she
called them. With its silly hat, translucent, bright green tights, and
short tunic that barely covered half of my ass, the Peter Pan costume had
surely been designed with humiliation top of mind.

I received much attention when I returned to the yard, dressed in my
absurd, new punishment attire, hearing laughter and sniggers from all
around me. I had expected Amanda to ask Jason (or perhaps, Ryan) to
deliver my correction while she looked on and directed, as was customary.
I was quite startled, therefore, when, after ordering me to bend over a
chair, she stood behind me and started swooshing her crop. Amanda had
never personally delivered my corporal punishment before. She tapped the
crop three times against my tights-clad bottom, which was fully exposed
to the crowd. I noticed that nearly everyone in attendance had gathered
around the area where my chastisement was occurring, no doubt captivated
by the prospect of seeing this regal, beautiful young women about to whip
this much older man, her father no less, dressed so ridiculously.

Amanda proceeded to deliver 20 searing strikes to my buttocks and upper
thighs, requiring me to say, "Thank you, Miss Amanda, may I please have
another?" after each one. The crowd found the clichéd nature of making me
ask for more punishment to be highly amusing. Tears were running down my
eyes by the 15th stroke (whether more of pain or of shame, it was
difficult to tell).

At the 15th stroke, I said beseechingly, "Mercy, Miss Amanda. I have been
whipped many times today. I'm not sure I can take anymore."

She ignored me as she delivered five additional strokes. At the
conclusion, Master Ryan, instructed me to kiss my daughter's boots in
gratitude. As I did, so, they embraced and kissed amorously. Amanda next
commanded me to assume my penance position, legs spread and hands behind
my head. The burning sensation in my bottom notwithstanding (or perhaps
in part because of it), it was not long before my cock began to stir.
Unable to meet anyone's eyes, I stared down in shame.

I had now visited with all the guests, but there were still a couple of
hours left before the party was scheduled to conclude. Jason decided that
an impromptu fashion show would be entertaining. There was a raised
platform in the middle of the yard with a paved path leading up to it,
guest chairs on either side of the path. That path served as my runway as
I modeled the various girts I had received throughout the day. First,
were Alyson's two T-shirts, Lauren's Lackey and Jason's Skivvy, wearing
nothing but the shirts and my green tights. Next, I modeled the British
schoolboy outfit, carrying Jason's golf club bag.  Beneath the
ridiculously short tight shorts, the marks Amanda had left on my thighs
were clearly visible. Finally, I modeled the ballet ensemble. Jason
insisted I do a pirouette, standing on my toes with my hands over my
head, in a preposterous imitation of a ballerina. Each outfit was greeted
by animated applause and laughter from the guests.

We had now come to the penultimate event of the day.

Following my fashion show of the absurd, Lauren ascended the platform and
addressed the guests: "I am sure that you all have noticed that Gregory
has lost some weight. This is thanks to his diet, as well as to the
rigorous exercise regimen that Jason has put him on as his personal
trainer. However, before treating you to one of Jason's unconventional,
yet highly effective personal training sessions with Gregory, Amanda has
an absolutely delightful, surprise announcement to make."

Amanda came up onto the platform, beaming, and announced: "Ryan proposed
to me just a little while ago in the house, and I'm happy to say that I
immediately accepted! I am overjoyed! We will be getting married next
July, just a couple of months after Mom and Jason, right here in this
very garden. Given our unusual circumstances, I have asked Mom if Jason
could give me away, and they have agreed. All of you are invited to our
wedding! My father, of course, will be among those serving the guests."

This news was met with rapturous applause, and much clinking of glasses
to toast Amanda and Ryan. Ryan came up onto the platform in the happy
couple passionately kissed. I had to admit that they were a stunningly
attractive couple.

Amanda then said, "Since my father will now have two masters, I have
asked Ryan to partake in his training session, and he has graciously
agreed. Please enjoy! "

Amanda's big announcement was not that surprising to me. After this
weekend, Ryan could clearly see that in Amanda, not only would he be
getting a beautiful woman who stood to inherit a multi million dollar
fortune one day, but that, whenever he visited, he would get her
61-year-old father as his lackey, boot boy, and maid, to wait on him hand
and foot -- a living, breathing aphrodisiac, someone he could punish at
will to light a fire in Amandas loins. Not a bad deal, if you could get
it.

Inside the pool house, Jason instructed me to remove the tutu and
leotard, but keep on the pink tights. After fixing a collar around my
neck, he led me back out to the yard by a leash, accompanied by Ryan.
Both were shirtless and dressed in jodhpurs and riding boots. While more
slender than Jason, Ryan had a well defined toso that clearly showed to
the party guests part of his appeal to Amanda. Jason then proceeded to
put me through the same paces that he did on the earlier day in front of
Penny, Alyson and Samantha. Ryan observed carefully. Following my second
water break, Ryan took over, forcing me, under the lash, to perform the
same high steps, push-ups, deep knee bends, and jumping jacks I had just
done with Jason, as if I was his marionette. When I collapsed at his feet
at one point to catch my breath, he even copied Jason's practice of
tapping my balls through my tights with his riding crop, to ensure I
didn't extend my rest a second beyond what was absolutely necessary.
 When the 45 minutes were up, sweat drenched and exhausted, I crawled
over to Jason and Ryan, standing together, and began to slavishly lick
the boots of both of my unsparing, young masters.

My gauntlet of punishment and ridicule was nearly complete, but not
quite. >From the lawn, Jason led me by my leash up to the platform where
my fashion show had taken place. The sun was now setting, and the light
was resplendent. Seated on the platform were Lauren, Amanda and Ryan.
Amanda and Ryan were still dressed in their equestrian attire, as was
Jason. Lauren was wearing the same short dress with black stockings and
heels that she had worn all day. Jason directed me to lay prostate on the
platform, my face near the feet of my wife and daughter, with Ryan seated
by my midsection. Lauren bent over and grabbed both of my nipples,
squeezing them tightly. Once they were suitably erect, she and Amanda
affixed nipple clamps. Amanda removed her boots and placed her moist
socked feet over my face. Ryan rested his boots on my chest.  Lauren
begin inserting her stocking-clad toes into my mouth for me to suck.
Jason stepped onto the platform and placed the sole of his boot firmly on
my cock, the heel pushing into my balls. I had been denied release for
the prior three weeks, so my cock was impossibly hard despite my
overwhelming pain and fatigue. Jason and I then commenced a dialogue that
we had refined in his and Lauren's bedroom over the previous couple of
weeks:

"What are you, Jenkins?"

"I am your paralegal, sir."

"How old are you?"

"I am 61, sir."

"So, you are 61 and still a paralegal? You must be pretty incompetent."

"Yes, sir."

"What else are you?

"I am you're lacky, sir."

"What else?"

"I am your maid."

"What else?"

"I am the maid to my family."

"What else?"

"I am the oldest here and the lowest."

"What else?"

"I am the ground beneath everyone's feet."

"What else?"

"I am your lowly slave, master."

Jason smiled down at me, maliciously, and said, "Slave, you may now hump
my boot."

Looking up at the superior faces of the two women and two men above me,
inhaling the commingled odor of leather and my daughter's foot sweat, and
sucking on my soon to be ex-wife's toes, I was deep in what I have now
come to understand is the state of mind known as subspace. I thrust my
pelvis up against Master Jason's boot as he continued to press it down
firmly on my cock and balls. As Jason looked around the crowd, confident
in his complete and utter victory over me, my cock erupted prodigiously
through my tights and onto the bottom of his boot. I heard laughter and
applause in the background, but I was a depleted, quivering mass of flesh
on the ground, barely conscious. After a few minutes, I licked my
ejaculate off my master's boot.

I was given a few minutes to compose myself before going to the pool
house to shower and put back on my maid's uniform and fresh stockings.
There was still an hour left of the party, and I had work to do. I
thought about the day and the balance of karma. Of the 30+ years of my
horrendous behavior, how much could I possibly have atoned for over the
course of one afternoon, no matter how intense? Two months? Three,
perhaps?

My journey had only just begun.