Medieval Simp Lord Chronicles Pt. 01

As I felt the immense heat in my abdomen, I contemplated finding a private room to rub one out in, however I decided against it. That would require time, which I didn't have.

I hurriedly rose to my feet, as I remembered where the kitchen was from the map in my mind. Bringing all the plates and tableware over, I swiftly cleaned and set them over to drying.

After completing the task, I rushed out the door, not even noticing the two maids standing dumbfounded in the kitchen looking at my receding picture, 'Did the Master just clean all the tableware quicker than a maid?'

Not knowing I had apparently broken some "Dishwashing" record among the maids, I was running in happiness towards the maid dorms. 'Here I come, Paradise.'

I was standing in front of Mistress Olivia's dorm room in a matter of minutes. My heart beat violently in my chest from the anticipation building inside me. Slowly, I raised my hand to the door and knocked gently.

*knock knock*

"Come in," an authoritative female voice sounded from within the dorm room. Compelled to do everything the owner of the voice told me; I opened the door without hesitation.

Once I had closed the door behind me, I bowed towards Mistress Olivia and said, "Sorry for making you wait, Mistress."

After saying my piece, I couldn't help myself from surveying the room I had entered.

Small! The room was very small, only having room for a rough bed, a tiny old desk, and a cloudy mirror.

The room clearly only had the bare minimum for living.

Seeing the 56 years old Mistress Olivia sitting on the tiny rough bed, my heart felt indignance on her behalf, as a frown appeared on my face. This wasn't alright!

Mistress Olivia, who at first was sitting on the bed with a cold expression noticed my frown and with a stern voice, she said, "Why are you frowning slave? Dissatisfied with the accommodations?"

Sarcasm was present in her voice, yet before she could say anything else, "Yes!"

The response burst out of my mouth, surprising Mistress Olivia. A frown appeared on her face, as if thinking I was arrogantly complaining about having to be in this small room. Just as she was about to open her mouth to berate me, I swiftly continued with the rest of my speech.

"This can't continue. How can it be alright for Mistress to live in such a cramped room, without even a proper bed? I beg for Mistress to move her accommodations to one of the high-end bedrooms in the villa, or your slave won't be able to quench this indignance in my heart."

All my thoughts burst out of my mouth in a moment of frenzy. Once I was done speaking, I realized that my tone had been a little too forceful.

From my still bowing position, I directed a timid glance up towards Mistress Olivia, sitting on the bed with her legs crossed gracefully, wondering if she would be mad at me.

Unexpectedly, Mistress Olivia's face seemed a little surprised, before excitement flooded into her eyes. A sadistic smile formed on her mouth, as she teasingly said, "What is this? The lowly slave saw his Mistress in the room which he himself has accommodated for her, and then he even has the gall to spout nonsense about indignance and then even demanding that his Mistress change rooms for him. Is this the way a slave should speak to her Mistress?"

I trembled at Mistress Olivia's words. I had made a mistake. Even if I wanted her to move out of this cramped room, that didn't make it alright to beg her with such a forceful voice.

Mistress Olivia seemed to notice my trembling, as she switched to a more dominant tone and continued, "Do not worry, little slave; I had already planned to move out of this room. Though your sentiments for me please me, I still think you deserve some punishment for speaking to me in such a fashion."

As soon as the word punishment left Mistress Olivia's mouth, my whole body trembled. A weird mix between trepidation and excitement filled my body at the thought of how she would punish me.

"Get on your knees before me, slave!"

Mistress Olivia's voice contained unquestionable authority, as I obediently rushed to follow her command.

My knees plopped down in front of her as I knelt before her, awaiting her further orders.

Looking at me down on my knees before her, superiority flooded Mistress Olivia's face, "Good slave. Now then, why do you not continue your job from earlier and start kissing my dirty shoes?"

As the adage went, 'One man's punishment was another man's reward.' My crotch instantly got tight after hearing Mistress Olivia's order, as I obediently replied, "Yes, Mistress."

Moving my head down to her feet on the floor, I pressed my lips against her old black maid uniform shoes. Just from outward appearance, I could guess that they were definitely more than 5 years old and thoroughly worn.

But if the view wasn't a big enough giveaway about how used these shoes were, then the smell and taste of them were sure to make one realize it.

The smell was sour, best described as moldy and stale. As my lips touched the shoes repeatedly, spreading devoted kisses over their entire surface, the taste entering my mouth was sour and dirty. Even though this was only like spice on my meal, I still couldn't help frowning my mouth and nose a little.

Mistress Olivia was looking down at me enthusiastically kissing her dirty maid boots with a frown on my face from the taste, with a smile of pleasure.

"You seem to be enjoying yourself slave. Maybe I was being too kind with the punishment. Since that is the case, let us try something else. I have been wearing these shoes for a little over 7 years now, but I have been enjoying them so much that I have never wanted to switch them. Unfortunately, I have not had much time or energy to clean them, but now I have you. Stick out your tongue and clean my dirty shoes!"

Mistress Olivia's words ended with a slight tremble of excitement. I, too, couldn't stop a wildfire from brewing in my stomach at those words.

"Yes, Mistress," I replied, before letting my tongue slip out of my mouth and onto her shoes. The previous sour and dirty taste intensified. The more I slid my tongue over Mistress Olivia's shoes, the more of the nasty taste accumulated in my mouth. Every time my tongue became dry from the constant licking, I had to pull it back into my mouth to wet it, which only spread the vile flavor of her shoes further into my mouth.

As I slid my tongue up the soles of Mistress Olivia's, grayed from the wear, I could feel small grains of filth entering my mouth. Afraid of angering Mistress Olivia by spitting it out, I could only swallow it in reluctance, as I felt the taste spread down in my throat.

Mistress Olivia saw that I had begun struggling as soon as my tongue reached her soles but looked delighted at me swallowing the grime gathered under her boots instead of spitting it out. "What a good slave you are, swallowing the dirt without your Mistress ordering you to. You are the best shoe cleaner I could have wished for."

Even though it sounded like praise, the content of what she said was clearly degrading. However, how could I feel humiliated by Mistress Olivia's degradation? The only thing I felt was arousal at her words despising me.

"Thank you, Mistress."

"Hehe. Well, since you have cleaned the outsides of my shoes so nicely now, you can remove them from my feet and clean out the inside too."

"Yes, Mistress."

I lifted my hands to her shoes to remove them from her feet. This was a time before shoelaces, so the shoes would slip off with just a little pull.

However, before I could reach out to touch them, Mistress Olivia flicked her foot against my cheek. Of course, not with full power, but not gently either.

"Not with your hands, slave. Use your mouth," a stern command sounded from her mouth.

"Sorry, Mistress," realizing my mistake, I let my hands fall to the ground again. Then, with my teeth I gently bit the part of her shoes around Mistress Olivia's heel and pulled. After successfully removing one, and gently placing it on the floor, I repeated the same act with the other shoe.

"Before you start cleaning slave, I want you to stick your nose deep in one of my shoes and take a thorough whiff of the smell," Mistress Olivia said. Once again, a sadistic smile appeared on her lips.

I lowered my head to one of her shoes. Even from just being in the near vicinity of the shoe, I was able to get a sample of how sweaty and sour her shoes would smell.

Gathering determination inside me, I stuck my nose deep into her shoe and took a deep, loud sniff, making sure Mistress Olivia could hear it.

The smell that hit me was disgusting. If I ever wonder what shoes soaked in a bucket of sweat for 5 days smelt like, I found the answer in my nose at the moment.

Sweaty! The salty and sour stench of sweat flowed into my nostrils, yet it wasn't even the main ingredient. Something akin to the smell of moldy cheese dashed into my breathing ways right in the heels of the disgusting smell of sweat.

*cough*

I coughed and retched at the smell. Mistress Olivia seem to have expected this, and with a teasing look she asked, "How do my shoes smell, slave?"

Even though my head was still light from the nauseating smell of the shoes, I still realized that I could only answer in one way, "They smell fantastic, Mistress."

"Hmm, really? That's surprising. I have really sweaty feet, so even I myself cannot help but frown when I take them off. Sometimes in summer, they become so soaked in sweat that I need to place them outside my room because they reek so bad. For you to say they smell good, you really are a perverted slave."

I lowered my head in face of Mistress Olivia's contempt. This was still probably better than if I had honestly said how bad they reeked.

"Well, since you enjoy the smell so much, you will doubtlessly enjoy the taste inside them even more. Now get your tongue in there and start cleaning. I want to test if it is possible to remove the smell with your tongue."

"Yes, Mistress."

I reluctantly stuck my face into the first shoe. The smell was just as bad as before, yet this time I couldn't pull my face away to escape it. Frowning, I stuck my tongue out and tasted the sole inside Mistress Olivia's shoe.

Salty and sour, like the sweat had fermented in her shoe, which probably wasn't far from the truth. If the suffering of the stench on top of the acrid taste wasn't enough, small bits of dirt entered my mouth as I cleaned the inside of her shoe.

Every time I collected some dirt in my mouth, a sour bomb would follow, forcing me to use all my willpower to swallow it down.

Mistress Olivia, watching me twitch and tremble inside her shoe, but still performing my duty obediently, carried excitement in her, as well as some slight shock, "I am astonished, slave. I had expected some more resistance and complaining, considering how vile my shoes are, but you are staunchly performing your duty.

"If I ever doubted your submissiveness before, you have really convinced me this time. You are nothing more than a lowly human slave, lost without his Mistress' command."

I imagine that if she before contained even some slight respect for me as a human, it was gone now. Replacing it was only a feeling of contempt and superiority.

Understanding this, I felt slightly aroused and happy, feeling like I had accomplished my goal, yet also feeling inferiority. I could always wish to serve someone, but it was only when at this moment, that I realized the feeling of inferiority which naturally permeated you.

My reverence of Mistress Olivia was only rising as I lowly cleaned her shoes with my tongue, while she was intently staring down at me.

Five minutes passed before I felt that most of the smell which previously emanated from Mistress Olivia's shoes was removed. Lifting my head and breathing fresh air again, I understood that I had never had enough appreciation for fresh air.

That only lasted a moment however, before my head dove into Mistress Olivia's other shoe. The odor of this shoe was just as bad as the other smelt in the beginning. Once again feeling my stomach churning, I started once again lapping my tongue to clean Mistress Olivia's shoes.

Another five minutes passed, and the smell also finally disappeared from the second shoe. I lifted my head and said, "Your slave has completed the task, Mistress."

Mistress reached her hand down and held it under her nose, giving it a slight whiff. Then with a satisfied smile, she said, "Success. Most of the smell has really disappeared, though a slight stale odor remains... but I believe with continuous cleanings that will also disappear at some point, do you not think slave?"

My stomach churned at the thought of having to clean Mistress Olivia's shoes every day, continuously, until they didn't smell anymore, yet the only thing that left my mouth was, "Yes, Mistress, your slave will do his best."

"Good answer, slave. You might deserve a small reward later, but first you will have to satisfy me to earn it.

"I want you to be naked. Strip your clothes for me."

The order was rather sudden, but I still swiftly moved to follow it, standing up and stripping my clothes before Mistress Olivia's dominant staredown.

Once fully naked, I once again got down on my knees in front of Mistress Olivia, slightly embarrassed. Not just because I was naked in front of a fully-clothed Mistress Olivia, but also because my erect cock, which I had previously tried to hide, was now on full display.

Mistress Olivia also quickly noticed how erect I was, and with a teasing smile said, "Getting so erect from licking the dirt inside my shoes...your perverseness never ceases to amaze me, slave."

After saying that, Mistress Olivia placed her shoe down on the floor. Then, she grabbed the hem of her black maid dress, and pulled it over her waist, allowing me the most exquisite view.

Even though Mistress Olivia was 56 years old, her skin wasn't so loose as to be noticeable. Her body wasn't so thin either, so her legs and thighs were very full and looked soft to the touch, as if you could drown in them.

Since she was sitting down, some fat rolls had gathered at her abdomen area, which only furthered my arousal. In my mind, this full-figured body was a sign of leisure, which was the only thing I wanted from my Mistress.

Then, Mistress Olivia's grabbed the panty cloth around her crotch, and pulled it down to her ankles, making my jaw drop slightly and my cock, which was already hard from the earlier foot service, become so erect it started twitching, as if wishing to grow further than it already had.

Above and around Mistress Olivia's pink and luscious pussy was a heavy bush. My mind thanked the heavens for sending me back in the Middle Ages, before shaving your pubic hair was a thing.

Her bush was mixed with brown and gray hairs, and the hair around Mistress Olivia's pussy was clearly moist, proving how aroused Mistress Olivia was over her dominant position.

At first, when Mistress Olivia revealed her whole naked lower body, she looked kind of embarrassed, but noticing my cock twitching with arousal and my face, which was dazedly lost in her body her eyes instead glowed with excitement and said, "What does the slave think of his Mistress' body?"

I had been confused over her embarrassment. This was the Middle Ages, where nakedness wasn't anything new. On top of that, Mistress Olivia was over 50 years old and previously married. For her to become embarrassed from being naked should be impossible.

After hearing her question however, I understood. She wasn't embarrassed from being naked but instead the appearance of her naked body.

Mistress Olivia was old now, and nearly everyone would become disappointed in how their body naturally started losing its shine and becoming more unattractive with age. Also, it was clear that Mistress Olivia didn't try to keep herself in shape or look appealing, as proven by the excess fat on her body.

Yet all this had the opposite effect on me. I bowed towards Mistress Olivia and said, "Mistress' body is natural and curvy, bringing out all the most beautiful shapes of a woman. Thank you, Mistress, for showing your lowly slave this beautiful body."

A pleased expression appeared on Mistress Olivia's face, as she said, "Your words have thrilled me, slave. You can ask for a reward."

I didn't even need a second to think before replying excitedly, "Please allow your slave to pleasure Mistress' pussy."

Mistress Olivia seemed slightly stunned from my heartfelt request of giving her pleasure. Then she lightly shook her head before smiling, "I want to say it is unexpected, but I should probably have expected it. You want nothing else besides pleasuring me, do you not, my obedient little slave. Then I shall be kind and allow you to pleasure me. Show your gratitude."

I bowed my already bowed head all the way down to the floor before saying, "Your slave thanks Mistress, for her benevolent reward of giving her pleasure."

As I said those words my arousal burned in my stomach. A crawled over towards Mistress Olivia, who had already spread her legs to let my face into her pussy and was watching me with eyes of anticipation.

I first started with placing a few kisses up her thighs. With every kiss, Mistress Olivia trembled slightly from the pleasure. Then, I started placing kisses around her outer labia, before finally dragging my tongue up against her open clit.

"Haahhh."

Mistress Olivia released a deep sigh of relaxation and enjoyment as I slid my tongue in between her labia.

Since this was the Middle Ages, cleanliness wasn't easily accessible, plus Mistress Olivia was a house maid who couldn't even afford the rent to live in a house at the moment. Therefore, together with her erotic smell of pussy juices, there was a slight hint of staleness and urine.

In my mind though, this was like adding cheese to a burger. It was already good without it, but with it, it was magical.

As my tongue was relishing in all the tastes of her pussy, Mistress Olivia's hand grabbed the back of my head, forcing my head against her pussy. Even though she probably knew I would never move my head away without her command, she was probably just seeking the feeling of control that came with her forcing my head into her pussy.

Matching this guess, as soon as she had my head in her hands, her sighs and groans of pleasure started getting more frequent and louder.

"Oh, oh, hhaaahhh. Use that slave tongue of yours to pleasure your Mistress. You are only a tool for my pleasure. Mmmmhhm, yesssss."

Her open show of pleasure and the accompanying humiliating words made my mind nearly go insane with arousal, as my tongue started digging deeper into Mistress Olivia's pussy.

As I said earlier when massaging Mistress Olivia's shoulders, I had practiced all forms of service a woman could desire; of course cunnilingus was one of them.

As my tongue skillfully moved over her pussy, sometimes digging deeply into her vagina, sometimes teasing her clitoris and other times running full tracks through her pussy, covering all her most sensitive parts.

The effects were evident. Mistress Olivia was grunting and moaning, and her hands were forcing my head into her pussy even harder. Her mind had clearly become consumed with pleasure as she mindlessly started to even rub against my face between her thighs with her hips.

"Yeesss, yesss. This feeling of pleasure and power at the same time is too addictive. I will keep you forever as my tool for pleasure and your only reason to live is to follow my desires and obey my order. YOU'RE MINE, MY TOOL."

Her words were becoming more and more possessive and dominant as I could feel her getting closer to climaxing. Her grunts entering my brain and her dominant yells made me lose reason in lust, as I only sought to pleasure her as best as I could.