Lawyer2Maid Ch. 02

"Yes, Miss Amanda," I curtsied and scurried away, my bells jingling.

I promptly returned, dressed in the absurd red and green tights and tunic, and we began to open our gifts. I sat on the floor at their feet to open mine. This was my first Christmas since assuming my new status, and I made the calculation that shamelessly (or, perhaps it would be more accurate to say, "shamefully") sucking up in my gift selection was the prudent approach. For Lauren and Amanda, expensive perfume (Chanel No.5 and Chance by Chanel, respectively); for Jason, a personalized mahogany whip rack for his riding crops, engraved "Property of Master Jason." ; for Ryan, a reproduction of a Canadian prison strap from The London Tanners. I knew Amanda would approve of me buying an implement for her fiancé to discipline me with and I knew Ryan would approve of the store. They both would also approve once they researched the strap and discovered that its distinctive eight holes were designed to inflict maximum pain.

"Excellent choice," said Ryan, after opening his gift.

"Thank you, Master Ryan."

Amanda gave me a cedar shoe shine valet and, immediately following, asked Ryan to open her gift to him of a pair of expensive Italian leather boots. Ryan's gift to me was a feather duster.

Jason gave me a DVD of The Servant, which I was to learn is a 1963 British film written by Harold Pinter about a British aristocrat who hires a male servant. Over time, the servant and master reverse roles. The aristocrat's female lover kisses the former servant when she sees how he has subjugated her boyfriend. It is quite a remarkable film.

Amanda gave me the T-shirts "Ryan's Flunky " and Amanda Puppet " to go with the two shirts Alyson had given me at the garden party.

Lauren gave me the Buddy the Elf costume that Will Ferrell wore in the movie Elf, complete with yellow tights, black, pointy shoes, green coat with white collar and cuffs, black belt, and a green and yellow hat.

When I opened Lauren's present, Amanda exclaimed, "Oh, how fun! Father, put it on immediately."

Having just been ordered to change outfits not 20 minutes earlier, I must have unconsciously shown some annoyance in my expression, because Amanda angrily said, "How dare you look at me like that! When I say jump, you say 'How high?', and do so with a smile on your face. Ryan, it's time for you to try out father's present to you-- on his backside. Change into your elf costume first, father. You have three minutes."

"Yes, Miss Amanda," I said, hurrying off and questioning the wisdom of my choice for Ryan's gift. It appeared as though my plan had quite seriously (not to mention, rapidly) backfired.

I was out of breath when I rushed back into the room in the preposterous elf outfit. Ryan, wearing a Santa hat, removed his bathrobe, and was dressed in a tank top and sweatpants. He was caressing the fine brown leather of the prison strap as he ordered me to remove my green jacket and bend over a chair, my yellow tights-clad bottom jutting out.

Amanda said, laughing, "The strapping, young Santa is about to strap the naughty, old elf. Ha ha. It could be the start of a new fairytale."

Ryan rubbed the strap against my bottom before delivering the first of the ten blows stipulated by Amanda. It was excruciatingly painful, far worse than a caning. By the fifth stroke, tears were streaming down my cheeks, and I felt I had no choice but to take the risk of speaking -- or, to be more precise, beseeching.

"Please, Miss Amanda. Mercy, I beg you. This strap is notoriously painful. I'm not sure I can take five more. Is there any other way I can be punished?"

Jason said, "I've been researching this strap on my phone. Jenkins is not lying. It is supposedly wicked. It probably should be reserved for the most serious transgressions." Jason coming to my rescue was most unexpected but most welcome.

Amanda replied, "Very well. It is Christmas after all. Just give him one more please, Ryan, for good measure."

After the final withering stroke, I took a moment to compose myself and wipe the tears from my eyes, before dropping to the floor. I then crawled on my belly to Amanda and kissed her slippered foot. "Thank you for your kind forbearance, Miss Amanda," I groveled, "I truly do not deserve it. I promise to be more careful in the future."

I then slithered over to Ryan and kissed his bare foot. "Thank you for correcting me, Master Ryan, and for your leniency." Next, I crawled to Lauren and Jason and kissed their slippered feet as well, apologizing for my insolence.

When I stood up, Amanda looked at me calmly, and said, simply, "Father, jump"

Knowing exactly what was expected of me, my eyes still moist, I forced myself to smile -- I had smiled so seldomly over the last 10 months that it felt strange even using those facial muscles -- and said, "How high, Miss Amanda?"

"Three feet."

My 61-year-old legs were not able to propel me even close to 3 feet into the air.

Amanda said, "Since you are physically incapable of fulfilling my command, you can make up for it by jumping around the room. Your yellow tights remind me of Easter. Hop like the Easter bunny, father."

As I started to hop in a circle around the room, smiling idiotically, she added, "Hold your hands up like bunny paws," demonstrating with her hands what she expected.

Given Lauren's and Amanda's seemingly insatiable desire to treat me as their living dress up doll, that night I was to have nightmares about what humiliating outfits awaited me at future holidays: Cupid for Valentine's Day, a leprechaun for St. Patrick's Day, and, of course, the Easter bunny (probably with a cottontail and floppy ears to go along with my yellow tights)? And who knew what else...

After five laps of hopping absurdly around the room, my bells jingling incessantly, I was ordered to assume my penance position -- on this occasion with a bit of variation. Instead of facing them as usual, I was instructed to kneel in the corner with my shins and toes elevated and pointed straight out, hands held behind my head, fingers intertwined. My yellow tights were pulled down to my knees, so my bruised and battered bottom was fully exposed. After 15 minutes, as my legs started to visibly tremble from the stress position, I was then granted still more Christmas clemency by Amanda.

"You may stand, father. Pull up your tights and face us, legs apart, hands behind your head, for another 15 minutes." Up until that point I had been in too much pain to have any hint of arousal. However, facing the four of them, it didn't take long for my body to begin to betray me yet again.

Fortunately, that evening there were no guests as I served an abridged Feast of Seven Fishes -- even though we were not Italian. They didn't think I was fully ready for such an elaborate meal yet, so I prepared four dishes and Lauren bought three from Citarella's seafood market. I served the dinner in my green maid's uniform to maintain the festive spirit of the day. They generously allowed me to eat a small portion of the seven dishes at my small table in the kitchen while they had coffee and dessert in the dining room.

After dinner, the five of us watched The Servant in the home theater. Amanda had directed me to change into the striped Christmas tights and an ugly Christmas sweater ("I've been Naughty"). The four of them sat in the plush theater seats, while I lay on my side on the hardwood floor at their feet, trying to avoid putting any pressure whatsoever on my still smarting bottom. Since it was my gift that we were watching, Jason was kind enough to pause the DVD for me while I made fresh popcorn and opened up a new bottle of wine to serve. After I resumed my place on the floor, Lauren tousled my hair with her socked foot. I then felt a light but persistent kicking against my balls. I looked up to see Ryan struggling to suppress a grin as he ostensibly watched the film.

Following the movie, Jason asked, "Did you identify with any of the characters, Jenkins?"

"Yes, sir, I did. I identified with the main character, the aristocrat, who becomes a servant in his home."

Jason then let me know that he expected a 20-page essay analyzing the firm's social downgrade, homoerotic and cuckoldry themes, as well as analyzing the characters and comparing the script to other Pinter screenplays. I had a little over a week to research and compose my paper, which would be graded.

The next morning, Lauren and Jason were scheduled to fly to Saint Barts for a weeklong vacation. Because Amanda and Ryan were staying at the mansion for the first three weeks of their five week break, I would not be unsupervised. This was a source of not a little anxiety for me. While Jason and Ryan were both sadists, Ryan was far more insecure than Jason, and had a chip on his shoulder. The combination of his sadism and insecurity -- along with the obvious thrill Amanda experienced whenever Ryan exerted his authority over me -- did not bode well for me.

I was up at 5 AM the next morning as Lauren and Jason had 9 AM flight out of JFK. Despite the early hour, I wore my formal serving uniform, because I knew it would please Lauren. When their car service arrived, I took their bags out to the car. The young man driving the car had picked me up for various business trips in the past, and smirked at me as he put the luggage in the trunk.

Lauren said, "You better be obedient for Amanda and Ryan, Gregory. We don't want to hear any negative reports."

Jason added, "And I expect your essay to be complete when I return. When I'm away, you will have access to my Amazon Prime and Criterion accounts to do your research."

Curtsying, I replied, "Yes, ma'am. Yes, sir. Thank you, sir. I hope you both have a wonderful trip."

It pained me to say this, because Lauren and I usually went away the week between Christmas and New Year's to a different Caribbean island each year. Last year on the 26th, around the same time in fact, we were leaving in an Uber to catch our flight to St. Martin. Now, instead of sipping cocktails on the beach, I would be waiting hand and foot on Amanda, Ryan and their guests.

I changed into my working uniform and began scrubbing the bathrooms and kitchen to prepare for the arrival of Ryan's good friend, Paulo, and his girlfriend, Rebecca, in the early afternoon. Paulo was from Brazil and had met Ryan when they were together at boarding school in Connecticut. He was the star player on Brown University's soccer team.

Amanda was planning on spending the day at Manhattan with her friend Mia, who was also home for winter break. This would be the first time I would be left alone with Ryan, and I was very apprehensive about it.

Back in my serving uniform, I served Amanda and Ryan breakfast around 9 AM, standing at attention next to the table, ready to refill their cups of coffee, or get anything else they wanted. Meanwhile, I heard them discuss the impending visit of Ryan's friends.

Amanda said, "Are you sure we can trust them? Won't they be shocked, scandalized even, when they're introduced to my father dressed as maid?"

Ryan said, "Are you kidding? I thought I had told you. Paulo has quite a bit of experience in this area, and I would trust him with anything. His girlfriend, Rebecca, is his submissive. She is sort of the female equivalent to your father here, just not as extreme; I believe she's what's called a cuckquean."

"Rebecca? Not Rebecca Langston?"

"Yes, that's her. Do you know her?"

"Do I know her? She was in my sorority freshman year and then, over the summer, she mysteriously transferred to Brown. We couldn't figure it out. I knew her to be really stuck up and bitchy. Definitely pretty, even sort of sexy. But I couldn't imagine her being submissive to anyone. I used to see her be sort of abusive to her boyfriends, if anything."

"Well, Paulo has that effect on women. He's a very dominant kind of guy, full of machismo. You've met him a couple of times, you know what I mean. Rebecca transferred to Brown after meeting him at a party. They went on a couple of dates afterwards, and she completely fell for him. I understand what you mean about her treating guys like dirt. She has this 30-year-old simp who follows her around like a puppy dog. Paulo dominates him as well. Paulo told me that Rebecca confessed to him about having this fantasy of him cheating on her, and her becoming the third wheel in the relationship. So, the person he chooses to do it with is this beautiful Indian girl, Shyla. Rebecca and Shyla were bitter rivals in their sorority and, in fact, it was Rebecca who won out in being elected to one of the top leadership positions in the sorority. I'm sure Paulo knew all this when he decided to sleep with Shyla.

Anyhow, Rebecca is now Shyla's little lackey and maid, sort of like your father is for Jason. Shyla is now president of their sorority and Rebecca has been demoted to sorority bitch. She's bossed around by all the girls she used to lord it over, even the lowliest pledges. She cleans the sorority house dressed in a skimpy French maid uniform, and gives her sorority sisters foot and body massages on command. They even have a sorority paddle with her name engraved on it. It's pretty hot, actually. So I don't think there will be any issue with Paulo and Rebecca understanding the situation with your father. Or keeping it private."

"That's amazing. I can't believe it! I wonder why Rebecca puts up with it?"

"I think she's in love with Paulo and hopes that he will marry her someday -- which I sincerely doubt. But stranger things have happened, I guess. When Shyla isn't around, they almost seem like a vanilla couple much of the time. I also think Rebecca is just really turned on by the whole submission thing. She seems to be addicted to the humiliation. She gets off on it. I think she must be bisexual. There's a good chance you will get to see this dynamic in action, because Paulo said that he invited Shyla to come down the day after tomorrow, and stay for a night or two. I hope that's okay."

"That's fine. It sounds like it could be quite interesting."

"Yes, we might have a couple of maids to serve us this week."

I couldn't recall college kids being this kinky when I was in school. I have to admit, however, that I was intrigued. But, if I'm being honest, I was also somewhat uneasy about having to share the submissive spotlight with someone.

Truthfully, that's probably another reason why I stuck around in my state of enslavement, rather than leave. I had always liked being the center of attention -- in the boardroom, the courtroom, sitting at the head of the table in the mansion, etc. Never in my prior, privileged life, however, had I been the center of attention in the intense way I had been over the last 10 months in my subjugation. There were many times I was ignored, of course, but when I was punished or humiliated, the focus was squarely on me. This egocentrism is not a particularly admirable trait, I confess, but at least I was learning to be more honest about myself.

After breakfast, as she was leaving to take the train into the city, Amanda said to me, "Well, father, this will be an opportunity for you to spend some quality one-on-one time with your future son-in-law. I expect you to behave. I'll see you both this evening."

When she had left, Ryan turned to me and said, "I'm looking forward to bonding with you, old man. Put on your orange tights and meet me down in the gym."

Jason had entrusted Ryan with the key to my chastity cage while he was in the Caribbean. When I got down to the gym, I found Ryan shirtless, wearing sneakers and black sweatpants. I stood before him in my tights, and looked him in the eye.

"Pull down your tights, old man."

After I did as he commanded, Ryan took the key from his pocket and unlocked me, pulling my tights back up sharply. The feeling of my newly freed cock pressing up against the nylon, together with the overall strangeness of the situation, caused me to get hard almost immediately. Ryan stared down at my orange tent, smiling, causing me intense shame.

He then put my leather collar around my neck and tightened it, one notch tighter than Jason usually did. It was quite snug, but I could still breathe. He next instructed me to place my hands in front of me and handcuffed me.

"We're going to do your workout session with a bit of a twist today. I don't want you to get complacent."

He suddenly grabbed both of my nipples and twisted them with force. Once my nipples were hard, he put nipple clamps on me, causing my cock to grow harder still in my tights. He pulled on the chain to ensure the clamps were on securely.

As he did so, he said, "The first time I met you, you humiliated me in front of Amanda. I was falling in love with her, and I thought you might ruin it. I wasn't aware then of what an asshole you had always been to her and Lauren, so that your talking down to me probably only made Amanda like me more. But I will never forgive you for that. I'm going to enjoy paying you back for many years to come."

I really didn't know what to say, so I averted glance, looking down at the floor.

"I'll bet you're sorry now that you talked to me that way, you pompous old fuck"

"Indeed I am, Master Ryan. I am ashamed, and I am truly sorry", I said meekly.

"Not as sorry as you're going to be. I think you should be able to do all of your exercises with your hands cuffed with the exception of jumping jacks and push-ups. Let's begin."

After I did my high steps in a circle around him a few times, tapping my knees against the cane he held at waist level -- encouraged by slashes of his riding crop across my bare back, -- Ryan produced a large hoop. Think of a hula hoop, but maybe twice the size. He also brought out what appeared to be a dog whip.

After giving me a moment to catch my breath, he said to me, "They say you can't teach an old dog new tricks, but I intend to prove that's wrong. I'm going to hold the hoop up a couple of feet off the floor and you're going to crouch down on your haunches and jump through it. I will then keep raising it incrementally higher, and you're going to continue jumping through it, either till I say stop, or till you are no longer able."

I did as he commanded, leaping through the hoop, as he slashed my back, upper thighs, and even occasionally my still very sore buttocks with the dog whip. It was difficult to keep my balance with my hands cuffed, as I had to land on my feet. It was not long before I was sweating profusely, and finding it difficult to breathe

"Please, Master Ryan, I need some water," I pleaded.

"Very well, you may stop."

He then pulled out from behind the treadmill a dog bowl filled with water and pointed to it. Still handcuffed, I got on my knees, lowered my head down to the bowl on the floor, and began greedily lapping up the water to quench my thirst.

Following my usual sit ups and knee bends, I again became very winded and laid down on my back at Ryan's feet. As was Jason's customary practice, Ryan tapped my balls through my tights with a riding crop as I caught my breath. But whereas Jason tapped lightly but persistently, Ryan used more force. One of the strokes caused me real pain. I groaned and started to get up, but in the contest between giving relief to my lungs or to my balls, my lungs won and I fell back on the ground. Ryan did not relent in striking me.

"Don't get too comfortable down there, old man. You really should have more endurance by now. I think Jason may be going too soft on you."

After I caught my breath somewhat, he allowed me to lap more water from the bowl before saying, "It's time to practice your jumping more. I'm going to remove your cuffs to make it easier for you to land. You can now land on your hands and feet like a proper dog. Your front and hind paws, I should say. Ha ha. We're going to practice jumping several more times this week to prepare a little show for Lauren and Jason when they get back from their holiday-- and Amanda, of course. She really loves watching me bring you to heel, as I'm sure you have noticed. Maybe we'll invite a few others such as Penny, and Forrest and Jane." I groaned at the thought.