Lawyer2Maid Ch. 02

The next time I jumped through a hoop, he pulled a little crumbled piece of beef jerky from a bag in his pocket, and put it up to my lips. I looked at him incredulously, and he simply said, "Eat."

Obviously, he had planned this all out meticulously. He continued to feed me treats on every subsequent jump until I finished, finally laying down on my back at his feet, doused with sweat. It was painful to lie on my backside after last night's strapping, but I knew that's what he expected. He put his sneaker under the chain of my clamps, yanking them off with his foot. The pain was fiery, but short-lived, at least. After I finally caught my breath, he reattached the leash to my collar and pulled me upright. I then bent down and begin licking his sneakers.

After a minute, Ryan commanded, "Stop! Get back on your back.". He then placed one sneakered foot over my face to lick the and the other over my cock, which he pressed down firmly.

Eventually, I got hard again, but he did not allow me a release.

"Paulo and Rebecca will be here soon. Take a shower and put on one of your dressier uniforms so you can greet them properly when they arrive."

In my room, I changed into one of my better uniforms and a new pair of stockings. I self-consciously scrutinized my figure in the mirror. If Rebecca really did end up wearing a maid uniform at some point during her visit, I knew there was no way I could compete with a pretty young woman in her early 20s. Still, I didn't want to look totally ridiculous next to her. Even though I had lost a lot of weight, I still wished I had the benefit of wearing one of the corsets that Lauren sometimes laced me into when she and Jason made use of me in the bedroom. It occurred to me that my very thought process at this moment was a mark of just how far I had fallen. Here I was a once powerful, 61-year-old man, anxious about how i would look to my superiors in my maid uniform in comparison to another maid--an actual female, no less. It was really quite surreal.

After dressing, I went down to the kitchen to prepare coffee and tea for Paulo and Rebecca. I hurried to the door when I heard the bell ring.

Opening the door, I saw a remarkably attractive young couple. This impression was only enhanced once I removed their coats. Paulo looked to be a little taller than Ryan, perhaps 6'1", with swarthy good looks. He was dressed in tight jeans and a tight black T-shirt, muscles bulging beneath his shirt. Amanda was correct in describing Rebecca as sexy. She resembled a young Uma Thurman, and oozed sexually from every pore. Somewhat flat chested, she was dressed in faded jeans that hugged her hips and a short top that left her taut midriff bare, despite the cold weather. But it was her haughty expression that was the most striking thing about her.

"Greetings, sir, and ma'am," I curtsied.

"You must be Amanda's father, the big shot lawyer," said Paolo, grinning, as I removed their coats. He spoke with a moderate accent. Rebecca looked at me with a sneer, as if I was the most contemptible creature she had ever beheld.

"I no longer practice the law, sir."

"Well, that's pretty obvious," said Rebecca.

"Please, let me take you both to the sitting room, and I will get Master Ryan. Miss Amanda is out."

"You call your daughter miss? What a loser," said Rebecca.

Ryan entered the room and warmly embraced Paulo. Rebecca gave Ryan a peck on the cheek.

"This place is something. What is it, 10,000 square feet?", asked Paulo.

"12,000," said Ryan

"And this is the superstar lawyer? It all used to be his?"

"Used to be. His name is Gregory Jenkins, but feel free to call him maid or whatever you like. The house and everything else he once had now belongs to his wife, Amanda's mom, Lauren. She's about to divorce him and marry Jason, who used to work for him. He apparently was a real asshole boss, not to mention an asshole husband and father, but he fucked with the wrong person in Jason, as you can clearly see."

"Pathetic," said Rebecca.

After they were comfortably seated, I served them tea and stood by at attention.

"So Amanda's mom and Jason are on vacation and you and Amanda are cucksitting?," asked Paolo.

"I'm not familiar with that phrase," laughed Ryan.

"You've got a lot to learn, amigo. He's a cuck, isn't he? Rebecca here needs a cucksitter, from time to time, don't you babe? Shyla usually assigns one of the sorority freshman," said Paulo.

Rebecca looked down at her lap. It was really the juxtaposition of her haughtiness with her shame that was so sexy, as I would come to learn.

"So you can do whatever you want with him? Any limits?", asked Paolo.

"Nothing scatological, nothing that would send him to the hospital or urgent care, no permanent marks, no buggering," Ryan smiled. "Pretty much anything else is fair game. Creative humiliation strongly encouraged."

"Does he ever fluff you or suck you off?, asked Paolo.

"No, I think that's kind of gay."

"Don't knock it until you try it. Rebecca has a cuck. He's not too bad at giving head".

"Owen is not my cuck. I have never slept with him. He's my simp," said Rebecca.

"Distinction without a difference," said Paolo.

"I'll have to think about that one," said Ryan. "Whenever you're ready, I can give you a tour of the place and then we can go down to the gym and work out, if you want."

Rebecca said, "While you boys work out, I'm going try to catch up on my studies. I'm failing macroeconomics."

"Shyla is such a slave driver that Rebecca doesn't have enough time to study and isn't doing so well this semester. Isn't that right, babe?"

Rebecca looked down and mumbled, "I guess so."

Dressed solely in navy blue tights, I was Ryan and Paolo's spotter, and wiped up their sweat off the equipment while they worked out. Before showering, they sat around talking with Rebecca. I lay prostrate at their feet with one of Paolo's sneakers tied with masking tape over my face. He felt he needed to give the novice Ryan lessons in humiliating a submissive-- as if Ryan needed any.

I wore my sweaty face mask, inhaling Pedro's foot sweat, for about an hour.

At one point, Rebecca looked down and said, "Look baby, he's hard for the smell of your feet."

Pedro brought down his bare foot on my hard cock and said, "Down boy!", laughing.

"Don't worry, old maid. If I was a faggy, sissy maid, I'd get hard for the smell of my man's foot sweat too," snickered Rebecca.

After Rebecca returned to the library to study more, as Ryan and Paulo continued to catch up, I learned more of the fascinating backstory of the unconventional threesome of Paulo, Rebecca, and Shyla. After transferring from Dartmouth to Brown, Rebecca entered one of the top sororities on campus and began making a big push to position herself to become its future president. In order to do so, however, she had to first undermine another popular girl, Shyla. They quickly grew to be pretty serious rivals, each with their own factions of support. Shyla, like Ryan, had grown up partly in the UK and partly in the US. Her father was a wealthy business process outsourcing entrepreneur who built and sold a company, making billions. Rebecca, by contrast, came from a middle class upbringing outside of Philadelphia. But she was bright (salutatorian of her high school class) and ambitious. She was quite effective in syphoning off support from Shyla, partly through spreading false rumors about her. It sort of reminded me of yours truly in how I sabotaged Forrest at my former law firm. Apparently, Rebecca even used a racial slur to denigrate Shyla on a couple of occasions, which, of course got back to Shyla, infuriating her. In any case, Rebecca ultimately prevailed in being elected to the #2 leadership post, even though Shyla had been a member of the sorority since her freshman year at Brown.

Rebecca had told Paulo about her power struggle which Shyla, of course, and how she had triumphed. So, after she confessed her fantasy to Paulo that he cheat on her and relegate her to the third wheel in the relationship, he did not hesitate to seek out Shyla. Furious with Rebecca, and believing herself superior, Shyla became a very willing participant in the unusual love triangle. Paulo made it clear to Rebecca that, to remain a part of his life, she must submit herself completely to Shyla's authority. Rebecca reluctantly stepped aside from sorority leadership, clearing the path for Shyla to become president the semester that just ended. It turns out that most of the girls in the sorority, even Shyla's former so-called friends and supporters, thought of her as entitled and bitchy, and reveled in her downfall. This all certainly sounded familiar to me.

Paulo said to Ryan, "So you see, there's no one I could've picked to humiliate Rebecca more, but that's what really turns her on -- even though she won't admit it. She hates it but loves it at the same time, as you'll get to see you tomorrow when Shyla arrives. It's a trip."

Paolo and Ryan were still talking an hour later, when Amanda got home. She walked into the room to see both of them using my back as a footstool.

"Hi Paulo, nice to see you. I see you've met my father. Ryan, did you and father enjoy your bonding time together?"

"Yes, I think we're starting to get a better understanding of each other. But we definitely need a lot more time together."

Then Rebecca walked into the room.

Amanda said, "Well, if it is iisn't the long lost Rebecca. What the hell happened to you?"

Rebecca looked down at the floor and said sheepishly, "Hi, Amanda, nice to see you again. After I met Paulo, I just sort of felt I needed a change and I thought it was good idea to make a clean break. I'm sorry I didn't say goodbye."

Amanda replied, "From what I've heard, you certainly have gotten a change. I'll be sure to update everyone at Pi Beta Phi."

Rebecca said meekly, "Please don't, Amanda."

"We'll see. Father, shouldn't you be starting on our dinner?"

That night after dinner, the two couples sat around in the rec room listening to loud music. Pedro pulled out a joint which they passed around. I also served them cocktails and, before too long, the four of them were getting more and more inebriated and less inhibited.

Paolo said to Ryan, "My feet hurt from my game on Tuesday. How's the maid at giving foot massages?"

Ryan replied, "Not bad. He's been getting a lot of practice. Old man, show Ryan what you can do."

I knelt before this athletic, alpha male, still in my maid uniform, and began earnestly kneading the soles of his large feet.

When I finished, Ryan said to me, "Maid, don't forget our other guest." He was sending me a clear message: Rebecca may be a submissive, but she was still superior to me.

Rebecca was curled up next to Ryan on the couch and looked down at me contemptuously as I worked on her feet.

Out of the corner of my eye, I could see that Ryan and Amanda were getting increasingly amorous on the loveseat.

Also, observing this, I heard Rebecca say to Paolo, "Please baby, I haven't had any relief in nearly three weeks. I really need it bad. I need your beautiful cock. Please fuck me, baby."

"I'm afraid I can't do that, babe. I put the decision of when you next come completely in Shyla's hands. She'll be here early tomorrow, so maybe you can convince her to let you, if you are an especially good girl."

"Please baby, it's been so long. I'm losing my mind." She pouted. "Shyla is so mean to me."

"Don't forget it was you who wanted this."

"So you always remind me, but not with her! It was just a fantasy. I can't take it anymore. Please, I beg you -- at least unlock me so I can jill off. You have a key too. Why does Shyla get to decide?"

"Shyla's control is good for you. She is teaching you some humility, which you are solely in need of."

After finishing with Rebecca, I then moved on to massage the feet of Ryan and my daughter, until they left for their bedroom.

I got an early start the next morning, cleaning the mansion in my working maid uniform, including laundering the soiled sheets in both couples' bedrooms. While there was no question of the intent of my daughter and Ryan as they headed off to their bedroom last night, from the condition of their sheets, I can only speculate that Paulo compelled Rebecca to provide him some form of unreciprocated sexual release. I also had to prepare a third guest room; with Shyla's impending arrival, Paulo made it clear to Rebecca that she needed to move her things into the new room.

I put on my serving uniform to serve the four of them breakfast, before changing into my red and green striped tights -- Amanda liked to prolong the Christmas spirit as long as possible -- to accompany the two gym rats, Ryan and Paulo, through yet another workout. I fulfilled the same role of towel boy as I had yesterday, cleaning up their sweat as they moved between equipment. Fortunately, I was spared another workout session of my own (there were some allowances made for my age, thankfully).

As it turned out, Shyla was coming from nearby Sagaponack, where her parents owned a still more imposing 20,000 square-foot oceanfront mansion. I hurried to answer the doorbell just before noon. Shana was a stunning young woman, straight out of Bollywood central casting (I did a Google search to find a point of comparison, and the closest I could come up with was the actress Deepika Padukone ). She had silky, long, black hair and, at 5'10", was about 2 inches taller than Rebecca. Wearing opaque, black tights and black leather boots that came up to her knees, her short dress flattered her ample breasts; she was clearly better endowed in that department than Rebecca. What was most remarkable about her, however, was her regal bearing (in this respect, ironically, she bore some resemblance to Rebecca).

"You must be the father. I've heard about you. I have to laugh because it's so incomprehensible to imagine my own father ever being in such a position as you." She had a mild accent, Indian, with a hint of British perhaps.

I served tea while Paulo introduced her to Ryan and Amanda. Rebecca was conspicuously absent.

"Where is my little Becky?", Shyla asked. "I texted her a little while ago."

Paula explained, "Rebecca absolutely hates being called Becky."

Amanda said, "I remember."

Surprised, Shyla asked, "You know Becky?

After Amanda explained the history, Shyla said, "You mean to tell me that she came from your sorority at Dartmouth to create all of the trouble she did at my sorority at Brown? Incredible. Also exceedingly rude of her to have left Dartmouth the way she did. She will have to atone for that."

Paulo yelled up the stairs, "Rebecca, Shyla is here! You better get your little ass down here, pronto."

When Rebecca came reluctantly downstairs, I was startled to see that she was dressed as a sexy, parochial schoolgirl: short plaid skirt, white shirt and plaid tie, white knee socks, and black Mary Jane shoes. Her straight, light brown hair was tied into two pigtails.

Shyla said, "Good I'm glad to see you got my text, Becky. Come and remove my boots."

Rebecca ran to where Shyla was sitting on the couch and knelt down to grab the boot of Shyla's extended left leg. Struggling to pull it off, Rebecca stood up to get leverage. The boot suddenly came loose, causing Rebecca to fall on her bottom. Everyone laughed except for me.

"Be careful with those boots., Becky. They cost more than your father probably earns in a month."

"Yes, princess. Princess, I remembered to bring my school girl uniform but forgot my maid uniform."

"That was very negligent of you, Becky. I certainly hope it wasn't on purpose. You will be punished for that. Fortunately, I remembered to bring one of your spare maid uniforms in the trunk of my Maserati."

"Thank you, princess."

It readily became clear to me why Paulo and Shyla so enjoyed subjugating Rebecca. She was a jumble of conflicting emotions, evident in her ever-changing facial expressions. From one moment to the next she would go from disgusted to aroused, defiant to compliant, agony to ecstasy. She was a mess. But a singularly erotic one.

This was apparent from the start of her interactions with Shyla. After removing Shyla's first boot, Rebecca put her nose into the boot and inhaled deeply, as she had no doubt been instructed. With the first boot, she scrunched up her nose and grimaced as though the odor disgusted her. However, by the time she had removed the second boot, Rebecca seemed to savor the aroma; she took a second deep breath and lingered over it longer than was necessary.

"I have been in these boots for hours. My feet are sweaty. The odor must be nectar to you, Becky. I got them for Christmas and still need to break them in. My feet hurt. Massage them."

As Rebecca began to knead her soles, Shyla asked imperiously, "Aren't you forgetting something, peasant?"

"I'm sorry, Princess." Rebecca kissed the top of each stockinged foot reverently and then put her nose under each foot and inhaled deeply before resuming her massage.

"Do you see what's on my ankle, Becky?", pointing to an anklet on her right foot with a little key dangling from it.

"The key to my chastity, princess."

"I was planning on granting you a release today, because it's been a while, and I know how shamefully horny you get. But first I get a report from Princess Kyla that your last paper received a B and now I hear that you forgot your uniform."

Ryan explained to Amanda and Ryan, "Kyla is Shyla's younger sister, a high school senior. Shyla has appointed Rebecca as Kyla's homework slave. Shyla has to address Kyla as princess too. They do Zoom calls each week for Kyla to give Rebecca any assignment she's having trouble with. If Kyla's work receives any grade lower than an A, it's bad news for Rebecca. Isn't it, babe?"

"Yes, sir. I'm sorry princess. I was just so busy cleaning the sorority house and trying to get my homework done, I didn't have time to do as good as job as usual."

"That's another thing, Becky. I heard from Julie that there were hairs in my shower. You must learn to manage your time better. Meanwhile, not only will you need to work extra hard to earn your cummies, but you will need you will be punished for your shortcomings."

Pressing still harder into Shyla's soles, Rebecca begged, "Please, princess, I accept that I have to be punished, but you have to unlock me. I can't take it anymore."

"I don't HAVE to do anything."

After Rebecca finished massaging Shyla's feet to her satisfaction, I was ordered to prepare lunch.

Shyla said, "I think it's only appropriate as your guests that we help out. Go get your maid uniform from my car and assist Gregory here in making us lunch, Becky."

Rebecca looked at me with an expression of pure hatred as she ran out to the driveway.

When Rebecca returned, uniform in hand, Amanda said to me, "Father, you obviously know where things are in the kitchen, so you will show Rebecca around. But remember your place. She is a guest in our house and you will be the junior maid today."

So that was how I came to check off the box on my bucket list of indignities of being the junior maid in the house where not 10 months ago I reigned as master.

Amanda instructed me to put on my frivolous green maid's uniform. I felt this only added to my long list of disadvantages in comparison to Rebecca, which included my gender, age and weight, just to name a few. When I met her in the kitchen, she was wearing a sexy, but still practical black and white uniform, with a white hat and black and white lace choker around her neck. Her skirt was shorter than mine, which was already on the short side. Probably the biggest similarity in our attire was that we were both wearing black, seamed stockings and 3 inch heels. But that's about where the similarities ended. Whereas she presented as a highly attractive, sexy, young French maid, I was a ridiculous, sissified older man. She was an object of lust and fantasy; I was merely an object of ridicule and scorn. My confidence was not bolstered when she looked at me with undisguised contempt and rolled her eyes.