Lawyer2Maid Ch. 02

I reflexively said, "Christ, can't, I get any privacy anywhere?", before quickly correcting myself. "No! I'm very sorry, Master Ethan. Please forgive my outburst. I beg you!"

However, it was too late. Ethan was already halfway down the hall to tell his parents and Lauren and Jason about what he had just witnessed.

The nature and severity of my punishment was the subject of extended debate among Jason, Lauren, Nicole, and Bill. I was present for these discussions, but was talked about as if I was not there (I had, of course, grown, quite accustomed to this dynamic by now). Amanda entertained her young cousins with Ryan while my fate was decided.

My offense was deemed to have been egregious. Not only had I ruined Thanksgiving after what had been quite acceptable meal, I had violated Lauren's and Jason's trust by an attempt (albeit unsuccessful ) at unauthorized masturbation. In addition, and most unforgivably, I had exposed my perversion to young Ethan (never mind that I did so in my room, which he had no business entering -- in my state of powerlessness, I knew well the futility of trying to make any logical argument along these lines). Nicole felt strongly that I still needed to be punished for my rude outburst directed at Ethan the prior summer. All agreed that my punishment must be severe, and that Ethan, as the offended party, needed to play a meaningful role.

However, Bill and Nicole were clear that, even though they were young adults, they didn't want either of their children to see me naked or in my punishment tights (with my cock so barely concealed). At the same time, everyone wanted my humiliation to be maximized. It was a dilemma, but Jason was up to the task of solving it. The following course of action was decided upon: I was to be caned by Jason in my maid's uniform that evening in the family room with everyone present. The next day, Nicole and Lauren would watch Jason and Bill put me through my paces in one of my exercise sessions, attired in my usual tights and collar. Now that the weather had gotten colder, the sessions took place in the workout room in the mansion (a room used far more frequently by Lauren than by me in the pre-Jason days). I would then be required to wash and detail Bill's pickup truck under the supervision of Ethan and Isabella. The possibility of me spending a week next summer at their home in Virginia working for Ethan's burgeoning lawn care business was also discussed. Lauren also suggested that increasingly I would be confined to my chastity cage not only at night but at unsupervised times during the day.

That evening, I was summoned by Jason into the family room, where everyone was seated (except for Susan and Olivia, who had left early to beat the traffic).

Dressed in my formal serving uniform, I knelt before the entire family and said, "I'm deeply ashamed of my inexcusable behavior, and sincerely hope you can find it in your hearts forgive me."

I turned to Ethan, who looked down at me with smug satisfaction, and said, "Master Ethan, since you were the unfortunate victim of my thoughtless behavior, I beg you to please take an active part in my correction." I grew increasingly hard as I uttered these words, but fortunately, my shameful erection was concealed by my skirt.

Ethan looked at me with contempt as he said, "It will be my pleasure, uncle maid." Isabella tittered.

I was then directed to fetch the cane, which I presented to Ethan on my knees, palms upturned.

He looked uncertainly at Jason, who took the cane from him and said, "Observe me for the first five strokes, and then you can deliver the next five. There's nothing to it." Nothing to it for the wielder of the cane, perhaps. Quite another story for the one on the receiving end of the discipline.

Jason swooshed the cane his trademark three times before tapping it against my panty-clad bottom. He then methodically, but mercilessly, delivered five searing strokes to my buttocks. He next passed the cane to Ethan. I took measure of my extraordinary predicament: here I was, a 61-year old man, about to be caned by the bratty, smug 18-year old kid I had berated and intimidated a little over a year ago when he was a guest at the house where I now told toiled as the maid. My punishment was being witnessed by his equally bratty twin sister and their parents, people who always viewed me as arrogant and who no doubt took special pleasure in seeing me get my comeuppance.

A linebacker on his high school football team, Ethan was quite muscular for his age and, at 5' 11", he was taller than me. He was an attentive student, who impressively mimicked Jason in every respect from the swishing, to the tapping, to the rigorous administration of my correction. Tears were running down my cheeks by the eighth stroke. When he was finished, mindful of the seriousness of my transgression (and hopeful that my servility might result in some leniency in the punishments yet to come), I took a moment to compose myself, and then addressed Ethan.

"Thank you for correcting me, Master Jason and Master Ethan. Given the serious nature of my failings, I humbly request that you give me two additional strokes of the cane, Master Ethan, if your parents approve."

Nicole said, "I think it's only fitting."

Ethan enthusiastically indulged my request. I fell to my knees after the second additional stroke.

Although Ethan and Isabella bicker constantly, she gave him a high five when he finished. After being given a moment to go to the bathroom, I was directed by Jason to hold a quarter against the wall with my nose for the next 30 minutes, while everyone largely ignored me to watch TV. Fortunately, I managed not to drop the coin despite the intense discomfort in my neck muscles.

The next day, after serving lunch, I went to the gym to prepare for my exercise session. Amanda, Ryan, Ethan, and Isabella meanwhile left to see a movie in town. The exercise session was similar to what I had described earlier -- most recently at the garden party. The difference was that this time Bill took the place of Ryan as Jason's second, and the punishment was a bit more fierce than usual. However, given the condition of my bottom, Jason at least directed most of the attention of his crop to my back, mercifully.

Later that afternoon, I changed into gray, spandex yoga pants, a T-shirt, and sneakers, and began the laborious task of washing and detailing every inch of Bill's oversized pickup truck. Jason and Isabella sat on lawn chairs in the driveway, supervising. Ethan helpfully let me know whenever I missed a spot. He walked over to me, carrying a handmade switch -- a long branch from one of the large oak trees on the grounds that he carved with his pocket knife. On a couple of occasions, when he was dissatisfied with my efforts, he switched my still very tender buttocks and thighs.

"My dad always said you were probably a fag. I can't wait until next summer when you work for me for a week. I promise it will be an experience you'll never forget."

"Yes, sir," I replied, worried that my growing erection would be visible through my yoga pants, and validate his conclusion

I still did not believe it was accurate, however. My sexual identity had now become wrapped up inextricably with humiliation. The greater my degradation, the deeper my arousal. It's fair to say, however, that I found the homoerotic situations intrinsically more humiliating -- especially in the presence of females. The smirking Isabella, watching her brother in such command of her uncle, provided the extra spark in this particular moment of ignominy.

As I noted before, it was a complex situation.

Why did I stay and take all of the abuse, you may ask? Why not take my reduced (I was not yet 65) Social Security check payment and get a studio apartment somewhere, maybe take a job as a cashier or something? Well, there were several reasons.

First, thanks to my diet and Jason's rigorous exercise regimen, at 61 years old, I could honestly say that I was in the best shape of my life -- or at least since my early 20s. I had better endurance, a smaller waistline, and felt better physically (my perennially sore ass notwithstanding) than I ever had felt before.

I had lost a lot of weight, and secretly had begun to admire my figure in the mirror when I wore my uniforms.

No longer burdened with all of the responsibilities I had running the firm, arguing cases in court, investing my money, etc., I had less stress than ever.

Because of all the exercise and lack of stress (as well as the forced alcohol abstinence, probably), I was sleeping better than I had in years, even on my spartan cot. As I got into my late 50s, I started having to get up multiple times during the night to urinate, which prevented me from getting restful sleep. Now, thanks to Jason and Lauren, I was so physically spent from working all day that I often would sleep through the night (or, at least, most of it). I was getting deeper, more regular sleep with vivid dreams. I think it is probably no exaggeration to say that my dramatic change in lifestyle had the potential to add years to my life.

Lauren continued to finance my top-notch healthcare. I even was able to continue to see my long time GP (a doctor in his late 40s who at my annual physical in October had the tact not to inquire about my blue toenails, the welts on my backside, or my newly subdued manner).

Although I was a servant, I still got to live in the opulent surroundings to which I had grown accustomed. Jason and Lauren had even begun allowing me to swim in the pool (when no one else was using it, obviously) to reward me for good behavior. Similarly, for good behavior, and with their approval, I was permitted to read certain novels and watch certain films. With few exceptions, the authorized books and films involved some aspect of sexual subservience or social downgrade. But these could range from the movie Tar to James Joyce's Ulysses to the film the Duke of Burgundy to Somerset Maugham's Of Human Bondage to Edith Wharton's House of Mirth to Polansky's Bitter Moon. There was a surprisingly large range of options, actually. Jason and I had both been English majors before going to law school, and we would often discuss the books and movies. He had even begun requiring me to write book reports on some of the novels, and would grade my work. Obviously, there were punishments for poor grades (and he was a tough grader).

As I explained before, I was in a near constant state of sexual arousal, due to my near constant state of humiliation -- and while my releases were carefully regulated by Jason and Lauren, I never felt more carnal than at any time previously. Indeed, I had never felt more alive.

I was living a truly exceptional life. It may have been a life of degradation, subservience, and a certain amount of pain, but there is no denying that it was exceptional. Even as a highly successful lawyer, I could not say my life was truly exceptional; there are a lot of successful lawyers and executives out there. But how many successful people had fallen to my level, lost what I had lost, were reduced to a position of abject servitude in the places where they had once reigned supreme? How many powerful men had become their family's maid--not just for occasional games in the bedroom, but as their daily existence? It could be credibly argued that Jason had enabled me to truly achieve the exceptionalism I had always strived for but never really attained.

Jason's blackmail tapes were still hanging out there as well. Remarkably, I had not yet popped up on page 6 of the New York Post. Maybe that was because most of the people who participated in my humiliation were family members or had signed NDAs. I would be seen around town by people I knew, but perhaps my appearance had changed sufficiently that I was not recognized by too many people. It probably was just a question of time...But Jason and Lauren still had it in their power to forever stain my legacy in the public domain.

Furthermore, Jason and I were engaged in sort of an intellectual battle of wills that I found to be irresistibly compelling. He, of course, had already decisively won the battle -- had completely vanquished me in fact-- but I remained a consequential player in the ongoing game. Certainly, there were other key players as well: Lauren, Amanda, and more and more so, Ryan. But Jason and I would look each other in the eyes, and there was a sort of unspoken understanding between us. He would come up with ever more creative and demeaning trials to subject me to. Would I throw in the towel? Would I lose my mind, run away, commit suicide? I was determined to prove to him that I could endure anything he or the others could come up with. Perhaps that would be my sole victory over him, but it was something.

Finally, as I discussed earlier, I genuinely believe that my suffering is a form of cosmic justice, and that, by balancing the scales of karma somewhat, I would at least have some possible chance of peace or redemption.

Jason and Lauren continued to make use of me in the bedroom before, during, and after they had sex -- sometimes all of the above. They often had me dress in thigh high stockings, panties, and a corset -- which Lauren would lace tightly. Other times I would wear only my punishment tights. Still other times, I would wear a ridiculous court jester outfit to entertain my king and queen. Depending on their whim, I would sometimes be caged and other times my cock would be exposed for them to ridicule, smack, and toy with. Even when I was uncaged, there was no guarantee they would allow me to come. The superior manner in which Jason was able to pleasure Lauren, with his endurance and much larger cock, was also not lost on me, and enhanced my humiliation. Thinking back, I had to wonder: did she ever orgasm when she and I had sex, or was she always faking it to humor me?

Jason recently had started putting me into a humbler, an aptly named device, which I would wear as I fluffed him or cleaned up his mess from Lauren's pussy. The humbler prevented me from standing. (As an aside, it occurs to me that I now spend most of my life either standing, often in heels, waiting on people or cleaning, or on the floor at everyone's feet; where you won't find me is where most people spend so much of their time, seated on couches, tables, etc.-- except when lying in my cot at night, eating at my little table next to the pantry or driving in my Subaru). Jason and Lauren liked to toy with my exposed balls with their feet, or sometimes lightly tap them with a riding crop.

Both of them liked for me to worship their feet while they kissed, made love, or sometimes just talked. Often, they would have me lie prostate on the floor as they rubbed their feet on my face or pressed them down on my cock. On other occasions, I would be directed to suck their toes. Jason liked to remind me of all that I had lost -- Lauren, my house and assets, my position as a respected (or, at least, feared) father and boss, my dignity, etc. -- as I sucked his big toe, with Lauren looking on, smiling. If I failed to suck with sufficient abject enthusiasm, he would take me over his knees and spank me brutally with his bare hands until my leg legs kicked frantically.

And so, I endured.

The post Thanksgiving weekend proved to be a long one with me at the constant beck and call of the power drunk twins, Ethan and Isabella. I was relieved when they headed back to Virginia Sunday after lunch.

In the weeks leading up to Christmas, I assisted Lauren and Jason with their Christmas shopping. They did a lot online, but also brought me along to some of the high-end boutiques in East Hampton. I would walk three steps behind the couple, attired in my Lauren's Lackey T-shirt, carrying their shopping bags. One afternoon, we went to lunch at one of the steakhouses that Lauren and I used to frequent as a couple. While Jason and Lauren split a 26-ounce porterhouse for two and a bottle of Stags' Leap Cabernet Sauvignon -- the same meal and vintage she and I often enjoyed in the pre-Jason days -- I quietly ate the salad and bowl of soup that Lauren had ordered me, sipping a glass of ice water. I looked greedily at their porterhouse, hoping they might allow me some of the leftovers for dinner (as they occasionally did). It was the wine that I truly missed, however.

The maitre d, who had known Lauren and I for years, greeted our threesome uncertainly. Lauren warmly introduced him to Jason ("my fiancé"). I wasn't able to meet his eyes as he shook hands with me and observed my T-shirt. While Lauren and Jason were dressed smartly, I wore tattered jeans and frayed sneakers along with my T-shirt. The maitre d had been around the block a few times, and probably had some vague idea what was going on. In any case, he had the tact not to ask. The waitress who served our table had waited on Lauren and me several times in the past (and, no doubt, been the target of my rudeness); I could see her whispering to another waitress who also knew us, the two of them staring in my direction, giggling.

Holidays presented excellent opportunities for Jason, Lauren, and Amanda to humiliate me in novel, creative ways. On Christmas Eve, Jason invited Forrest and Jane over for cocktails and eggnog. I was dressed in a red satin, formal maid's uniform. It had black petticoats, and I wore it with black fishnet stockings with glistening rhinestones. Fortunately, I had not made any mistakes in my last proofreading assignment, so was not facing any planned punishment that evening.

Lauren and Amanda had also bought me a green satin maid's uniform. While I found a modicum of practical dignity (yes, I'm aware of the irony of that statement) to the black-and-white, formal uniforms, and even the spartan working maid's uniforms, I found other colors to be particularly demeaning in that they clearly could not be credibly worn by anyone save for a sissified male.

The couples exchanged gifts, as I served eggnog to the ladies and scotch to the gentlemen. Jason's and Lauren's gift to Jane and Forrest was a coupon book good for five cleanings of their 7000 square-foot house. I dreaded this because, from prior experience, I knew how exacting Jane was -- my inability to meet her standards (was it even possible?) had resulted in a couple of blistering sessions over both Jason's and Forrest's knees..

The next morning, Lauren, Jason, Amanda and Ryan sat around the Christmas tree, ready to open their presents. By now, I was receiving a $100 per week allowance from Jason and Lauren (I had even been given token tips from a couple of my former law firm subordinates after caddying or cleaning). Because they provided all my basic necessities (except for gas for the Subaru), I had managed to save up a small amount to spend on presents.

A couple of days earlier, Amanda had given me a pre-Christmas gift of festive attire that she made clear I was expected to wear on and around Christmas. This included three pairs of tights: one red plaid, one with horizontal red and green stripes, and one (doubtlessly inspired by Penny's recent gift to me) that had one red leg and one green leg. In addition, Amanda gave me a red velvet male Nutcracker ballet dancer tunic with gold embroidery. The tunic was very short, ending 3 inches above my crotch in the front, and covering about an inch of my bottom. It was accompanied by white tights and ballet slippers, and a red hat with a white feather. She also gave me an ankle bracelet with three small bells on it.

As instructed, I was attired in the Nutcracker outfit on Christmas morning as I delivered the packages under the tree to the four of them.

After I bought everyone their presents, Amanda said to me, "I'm tired of the Nutcracker look, father. Put on the red and green tights I gave you. Lose the hat and the slippers, but keep on the tunic. Make it snappy. We are ready to open our presents."