Last Day of Servitude (First Part)

LINK FOR CLIP  MEGA OR GDRIVE

(it's the last part of the story 7 days of servitude, the rest of the story is available on my deviantart page. I split this one in 2 as it's massive in size—next part probably in a couple of month)

The last day of my servitude had arrived. Seven days of obedience, housework, and well, other lewd things I never expected —but kind of hoped for— when I first lost that bet. For this final part, she had one last surprise.

After a speedy and light breakfast, we went to the study. Standing there, in that dimly lit room, she beckoned me forward and gestured toward the bookcase.

“I have something naughty to show you,” she said giggling.

“What? A raunchy book? I already dusted that bookshelf, I know there isn’t any” I answered, half-joking.

She reached for a book on the shelf —The Crimson Oath: Whispers of Grace by Sibylla Callipygous— and pulled hard. With a loud click, the entire bookcase shifted, sliding open to reveal a flight of steps leading to a narrow, candlelit corridor. My pulse spiked instantly.

I gasped. “What the hell is this?”

She glanced back at me with a smile, her lips curving upward. “You’ll see. Follow me”

I hesitated, but she didn’t give me time to think. She stepped inside, her long, elegant fingers curling around my wrist as she pulled me forward. The door shut behind us with a soft thud, and I squinted. The flickering candlelight cast long shadows against the crimson walls. I noticed a large door at the end of the corridor. The air here was warmer than the rest of her vast house, carrying the scent of polished wood, leather, and something faintly sweet. My feet padded against the intricate wooden floor as I followed her deeper into the unknown.

My breath hitched. “You...uh...don’t bring guests down here often, do you?” I asked nervously, trying to keep my voice steady.

She laughed softly. “No, only the special ones.”

That answer freaked me out. For a second, murder or kidnapping scenarios popped into my mind, but as she reached the end of the corridor and pushed the heavy door open, a bright and spacious room appeared and my mind blanked for a second.

Without thinking, I stepped inside and my eyes swept across the space. Natural light filtered in from a glass dome in the left corner, probably concealed somewhere in her garden, I assumed. The whole room was filled with curious things I barely had the vocabulary to describe.

Leather. Steel. Velvet. Ropes. Bondage.

Someone was already in the room. A woman stood by one of the shelves, a vacuum cleaner in hand. She was tall and imposing —over 1.80 meters, I guessed— with sun-kissed brown skin, curves that made my brain short-circuit, and long brown hair arranged in a chic yet simple updo. She wore a black and white frilly maid outfit, the tight corset emphasizing her ample bust and the short skirt her wide hips. Dark eyes flicked toward me, full lips quirking into an amused smirk.

She greeted my host with a kiss on the cheek and they chatted a bit before she turned her gaze fully on me.

Her voice was rich, carrying an accent I couldn’t quite place —Sulani, maybe? My throat went dry.

“Greetings, Mister. A pleasure to meet you.”

I greeted her back and turned to my host, my heart pounding.

“So uhm... what is this place?”

She took a slow step forward, her boots brushed against the polished floor.

“My sanctuary. A playground. A place where control is given… and taken,” she said in a weighty tone before switching back to her usual voice. “Oh! And it’s also my workspace.”

I exhaled shakily, the weight of her words pressing into my chest.

She tilted her head, watching me closely, the way a cat watches a mouse. “What did you assume I did for a living? You know... I wasn’t born into wealth. How did you think I could afford this estate?”

My skin burned, not just with disconcertment, but something deeper.

“So, you’re a... uh... professional d-dominatrix?” I asked, dumbfounded.

She took another step toward me, closing the distance, her fingers grazing my collarbone before trailing down my chest. “If you will. My official title is Discipline Tutor or at least, that's what appears on the invoice.” She crossed her arms, a smirk playing on her lips. “You wouldn’t believe the clientele I have. Famous, powerful, rich men. Some women too. The names on that list would make your head spin.”

I swallowed. “What now?”

Her smile widened, dark and wicked.

“Well, I’ll give you a taste, silly boy. Why do you think I brought you here? Plus, you’re still not off the hook for that game night.”

And just like that, I knew—this entire past week, she had been slowly and deliberately easing me into this moment.

In the meantime, the maid, composed and quiet, observed our conversation with amusement, her dark eyes flicking between my host and me. She seemed entirely at ease in this space, while I stood like a deer in headlights.

“I’ll go change into something more appropriate. Would you kindly keep him company, my dear? she said glancing at the maid before disappearing in another room behind a curtain.

The maid and I took seats on a nearby sofa, and she struck up a conversation. She praised my work in maintaining the house, mentioning that she often handled it herself, and even asked for advice on caring for the wooden floors. From there, we talked about the house, our host, and various other subjects. She listened attentively, engaged, and enthusiastic.

Our talk lingered before suddenly, a rather familiar voice, sharp and commanding shouted at me.

“Greet and praise your mistress, you miserable fool!”

I blinked. My host was standing right there in a different outfit, my heart stuttering for a moment before realization dawned. I wouldn’t have even recognized her if not for the fact that she was role-playing again and it wasn’t the first time—just like with the pirate queen.

A slow smile crept onto my lips. I exhaled and straightened my posture, lowering my gaze just enough to appear chastened.

"Forgive me," I said, keeping my voice steady, playing along.

“Forgive me, Mistress Sybilla!” she yelled, her eyes wide open.

I repeated it the way she wanted and she strolled toward the counter, the click of her heels sharp against the polished floor. She sat down with an effortless grace, draping one leg over the other as she rested her elbow on the marble surface. She looked beautiful and mysterious with a beak mask on her face and an intricate glittering top and tight black pants.

"That's better, worm." she mused, watching me with an amused glint in her eye. "But why are you still dressed in my presence?”

I gasped and stuttered; the words caught in my mouth.

"You’re a little dense, aren’t you? Undress, I said!" she commanded.

A small pause. Just enough to make her eyebrow twitch in warning. Then I pulled my shirt over my head, letting it fall to the floor and removed my pants.

"Good," she stated with no emotion. "Now, put this on."

She lifted a sleek, white sleeping mask and a collar from the counter and held them out to me.

I hesitated but finally tied it securely around my neck and the mask over my eyes, the world slipped into darkness.

"Serve me a drink, will you my dear?" She instructed to the maid.

"Yes, Mistress," the maid replied dutifully.

I heard the gentle slosh of liquid being poured, the ice clinking. A faint aroma of something rich and smoky filled the air. Then, the sound of the glass being placed on the counter.

Silence stretched between us. I stood there, blindfolded, vulnerable, every nerve in my body taut with expectation.

Then came her voice, soft but edged with command.

"Now, let’s give you some proper discipline, my boy."

A firm grip seized me, guiding me into position and my legs were spread apart.

"You know, like all men, the source of all your misdeeds is right there, between your legs."

The first strike landed sharp and sudden, pain blooming in my groin like wildfire. I reeled, instinctively trying to recoil, but unseen hands held me steady. Another hit—stronger this time—stole the breath from my lungs. Then another. My world collapsed into waves of sharp, biting pain. My knees buckled, and I crumpled onto the floor.

"Stay down," came the order, and I obeyed, lying on my back, my body thrumming with agony.

A firm, solid object pressed into my aching balls, at first soothing, then harsher, sending fresh shocks through my already overwhelmed senses. Nausea coiled in my stomach, dizziness creeping in. And yet, as the torment continued, something inside me adjusted, endured.

She suddenly lifted my legs up, pressing harder, faster, pushing me to the edge of my endurance until, at last, she relented.

"Impressive," she said, reaching for my blindfold and peeling it away. Her piercing gaze met mine, unreadable yet satisfied. "You sure can take a hit, boy."

A slow smile curled her lips as she leaned back, stretching lazily.

"Crawl over here, little worm" she commanded as she sat down on a sofa nearby, extending her foot expectantly. "I'm in dire need of a footstool."

The moment my body touched the floor beneath her, she pressed her feet against my back, claiming me as furniture. Time stretched. Occasionally, she nudged me with her toes, taunted me, amused herself while the maid served her coffee.

Eventually, she spoke to me directly.

"I know how you enjoy games so much, footstool. I want to play one."

My pulse quickened as I waited for her to continue.

"There are many bondage devices in this room. You’ll pick a number between one and twelve, and I’ll tell you which one you get." Her smirk widened. "I won’t lie, some of them are painful or very unpleasant. Think carefully before you decide."

She turned towards the maid.

"I’ll also tell my lovely and helpful assistant which is which. That way, she’ll be the one announcing your selection, so no trickery on my part."

A slow thrill crept up my spine, tangled with nervous energy. My mouth felt dry.

"You can roll the dice too, if you'd like," she offered teasingly, a big grin on her face. "That's in fact the preferred method."

I swallowed hard, my pulse hammering in my ears. One to twelve she said? That many choices, each carrying its own weight, its own punishment. I needed to think about this, was there any hint hidden around? I couldn’t think of anything so I finally blurted out the first number that came into my mind.

"Three."

A beat of silence. She didn’t seem too pleased which was... good, I think?

“The pillory," announced the maid in a casual way.

A shiver ran through me. The pillory. One of the more conspicuous objects in the room, I noticed it right under the glass dome as I entered. The maid moved efficiently, guiding me across the room to the platform where it stood. The floor there was smooth, cool marble.

"Could you kindly get down on your knees, sir?” she asked in a friendly tone.

I obeyed, shifting onto my knees as rough hands gripped my arms, guiding me forward. The wood was cold beneath my fingers as I was positioned into place.

"Head down, please" she murmured, her voice warm but firm.

I exhaled shakily and lowered my head. The wooden yoke came down over my neck and wrists, locking me in. The air felt thicker now, my breathing louder. The lock clicked shut and I was now captive. I tested the restraints but no give and no escape. Trapped.

For a while, my host was nowhere to be seen. Only the maid stood across the room, watching over me. I was just starting to feel uncomfortable when I heard the sharp click of stilettos approaching.

“Right where you belong, worm,” she sneered, striking my rear with an open palm.

Crouching down, she caressed my face. “Oh, you’re so cute when you’re helpless. I just wanna squeeze that face so hard.” She pressed a kiss to my cheek before dragging her tongue across my face.

“Oh, you know what? I just might...” she muttered mischievously as she began rubbing her breasts against my face, pressing them harder and harder. She was almost using them as weapons, slapping me left and right.

“Hmmm I’m going to need something larger to cover that face entirely and properly squash it,” she mused, turning around. “Heads-up.”

With a playful exclamation, she launched herself backward, using the pillory for leverage as she bent over and smothered me with her derriere. The pressure intensified as she pressed harder against my head, effectively cutting off almost all air.

Fear began to creep in, but then, with a wicked chuckle, she lifted herself slightly, granting me a moment of much-needed respite… only to drop back down with a forceful bounce.

The impact sent a sharp jolt through me. My vision blurred for a moment as she rocked against my face, almost as if was punching me with her fully clad ass. Fortunately for me, the fabric was soft and light.

She bounced rhythmically, her laughter filled with amusement and satisfaction. The weight of her pressing and releasing, again and again, left me gasping for breath whenever she lifted—only to be smothered once more as she slammed back down.

“Mmm, this is so nice,” she swooned.

Then, without hesitation, she slid off her pants, leaving only a thin layer of fabric between us. My skin burned with heat and excitation as she settled back onto me, this time with even more intimacy.

My senses overwhelmed by the warmth and softness enveloping my face. She writhed above me, her breaths growing heavier, her movements more deliberate. I started to panic as she didn’t pay much attention to my air supply and was just pressing her butt harder and harder into my face.

The maid, still standing nearby, brought attention to my plight.

“He’s turning red, Mistress.”

“Thank you, dear,” she replied smoothly. “I do love a little squirming, but that’s too much this early in the session.”

She leaned forward slightly, giving me just enough air to keep me on edge before delivering a final, forceful press from her big ass as a parting shot.

“Right,” she continued, brushing herself off with an air of satisfaction. “Next choice, worm. Give me a number.”

Out of breath and dizzy, I couldn’t think straight and just said, “number nine please, mistress Sybilla”

“Excellent choice, worm… but unfortunately for you, it’s more of the same.”

She turned to the maid, who was already waiting to announce my fate.

“The Queening Chair,” the maid declared with a hint of a smile.

I barely had a moment to process before the maid unlocked the pillory, freeing me just long enough to guide me toward the centre of the room.

My host took over halfway.

“I’ll do this one myself, dear,” she said smoothly, brushing the maid aside.

Without warning, she reached down and yanked off my pants.

“As I thought,” she smirked, wrapping her fingers around my stiffened penis. “Already rock hard, hmm?”

A flush of humiliation and arousal shot through me as she tightened her grip, using it to tug me forward across the room like I was nothing more than an obedient pet on a leash. Her firm grasp, the occasional squeeze, the way she led me with complete ownership. It was both degrading and utterly exhilarating.

When we reached the so-called Queening chair —which was nothing more than the stool chair she was sitting on earlier— she wasted no time. With practiced efficiency, she made me sit beneath it and secured my wrists and ankles in place with manacles and ties. My head was carefully positioned through the convenient opening in the seat, and with a slow, deliberate turn of a small crank, the mechanism locked into place. I was again trapped, this time in a chair, with my face serving as a seat cushion. The idea was... incredibly arousing.

“There,” she said, stepping back to admire her work. “You’re now a fancy human chair!”

This wasn’t the first time this week, however, today I was firmly tied up and my movements severely restricted which got me a bit nervous. And she probably noticed my unease as, with deliberate slowness, she circled the chair like if she were furniture shopping, building the anticipation. She trailed her fingers along my exposed body, occasionally brushing against my face.

Then, she turned her back to me, bent over slightly and gave her perfectly shaped ass a few playful slaps.

“Ready to serve, chair?” she asked.

Apparently, in her eyes, I had graduated from worm to chair. Progress.

She hovered just above me, her body close enough that I could feel the heat radiating through the fabric of her pants. But she didn’t sit, or at least, not right away. Instead, she teased me, shifting her weight from side to side, rocking her hips tantalizingly above my trapped face.

She plopped down suddenly, her weight embracing my head. The abruptness of it stole my breath, but thankfully, the sturdy padding of the seat prevented the cushion from sinking too low. There wasn’t too much strain on my face, in fact, after adjusting, it was quite comfortable. Comfortable enough that I could enjoy the intimate face-to-face with her wonderful derriere without too much pain.

A pity that she was still wearing her pants...

Settling in, she let out a contented sigh, then casually picked up her drink. She began chatting with the maid, speaking as if I weren’t even there. Occasionally, she shifted her weight, adjusting herself for comfort, pressing down just a little harder, probably just enough to remind me of my place beneath her.

Time passed. Ten minutes? Fifteen? It was difficult to tell from my position. The world had shrunk to the warmth of her body above me, the muffled sounds of conversation, and the occasional flex of her thighs.

Then, finally, she acknowledged me again.

“You seem to be enjoying this too much,” she considered. “I don’t hear enough groaning.”

She stood abruptly, the loss of her weight making me gasp softly. My face, no doubt, was flushed red from the prolonged pressure. She glanced down at me with a smug expression before turning toward the maid, who had been watching the entire scene unfold with phlegm.

“Tell me… how much do you weigh, my dear?” she asked, her tone as casual as if she were discussing the weather.

The maid’s eyes widened slightly before she answered, nonchalantly, yet with a hint of mischief in her voice. She placed a hand on her hip as she eyed me with a subtle grin.

“About 97kg, Mistress,” she said smoothly, her sun-kissed skin glowing under the soft lights.

My breath hitched. I knew exactly where this was going.

Mistress clicked her tongue thoughtfully. “That might be a little much for my delicate chair,” she teased, giving my body a playful tap with her foot. “But… I suppose we won’t know until we try.”

A grin spread across the maid’s face. “As Mistress wishes.”

My heart pounded as the towering woman I barely knew stepped closer. She was tall but also much wider than my host, with strong, curvy thighs and an imposing presence that made me feel even smaller in my confined state.

Mistress sat on the nearby sofa, took a sip of her drink, clearly enjoying my predicament. “Sit down,” she said firmly.

The maid looked directly in my eyes and smiled. “Right away, Mistress”

Without another word, she turned, giving me a full, breathtaking view of her round, generous backside beneath her skirt. I gasped —Was she even wearing underwear? Unlike her mistress, she wasn’t one for teasing. She simply positioned herself above me, adjusted her stance… and took a seat.

A heavy thump echoed through the room.

I groaned instinctively as my vision went dark, her massive, plush bottom completely enclosing my face. She was so much heavier than Mistress; the sturdy chair barely kept my head from being utterly smothered. I struggled for breath, panic creeping in, until she wiggled her hips slightly to settle in, just enough for me to gasp against the warmth of her flesh.

My host let out a soft giggle while sipping her drink. “Much Better.”

The maid leaned forward slightly, pressing down just enough to make me squirm. I could do nothing but endure; I groaned; the pressure was overwhelming and the heat coming from her naked buttocks along with her scent was powerful and intoxicating. It was undeniably a more intense experience than before.

Minutes stretched on. The maid remained perched on top of me, as she idly conversed with Mistress. Occasionally, she would lean back, rolling her hips as if adjusting for comfort, her weight momentarily increasing before shifting again.

Suffering grew into arousal and I, mindlessly started to kiss and lick frantically the radiating juicy mass above, my tongue slipping out to taste her.

Mistress sighed dramatically. “I must say, having a human chair is such a treat. We really should do this more often.”

The maid hummed in agreement before letting an exaggerated gasp. “Mistress, the chair has started to use his tongue on my posterior! May I have permission to use him properly?”

Mistress’ playful tone faltered for just a second. Her fingers drummed lightly against her wine glass as she watched the scene unfold, her amusement shifting into something else. “I suppose it’s only fair to let my dear assistant enjoy herself for a little while…”

The maid, oblivious to Mistress’ sudden change in mood, let out a soft moan and swiftly removed her clothes as I continued my desperate worship, my tongue moving up and down instinctively against the form above. She adjusted her position again, cool air rushed in as she bent over to allow me to access her whole naked ass and pussy.

“Well, well…” mistress murmured, watching as the maid ground herself repeatedly against my lips, her breath hitching with every wild flick of my tongue.

The maid rocked her hips left and right against my eager tongue. Meanwhile, I was working feverishly to please her as I licked and sucked her asshole and pussy with reckless abandon.

“Such enthusiasm… Is he performing well?” Enquired Mistress.

The maid shuddered, bracing herself against the arm of the chair. "Mmm… yes, Mistress…" she breathed, her voice breaking between moans. "He’s… very… diligent."

The maid groaned and, without warning, pressed her ass down extra hard on my face, her plush flesh sealing me in completely. My muffled moan vibrated beneath her, my entire world reduced again to the warmth, the fragrance, and the taste of her rear end.

“Okay, that’s quite enough!” Mistress suddenly announced, her tone carrying a sharper edge. “I’m beginning to feel a bit envious over here”

The maid paused and followed the command as she slowly rose from my face, lifting the suffocating weight off me. Cool air hit my face again, and I panted, my skin burning from the heat and pressure that had overwhelmed me moments ago. My nose and jaw felt a bit bruised.

Hidden from Mistress' view, the maid winked at me, then puckered her lips in a teasing kiss before swiftly fastening her outfit back in place.

With a snap of her fingers, Mistress gestured toward my bindings. “Release him.”

“Of course, Mistress.” The maid quickly moved to undo them, releasing my wrists and ankles from their restraints. My limbs were sore and weak from the prolonged captivity but I steadied myself as I crawled down and stood back up.

Mistress was laying on her side on the sofa, presenting me her naked backside, her legs partially bent, her pants and panties discarded in a careless heap on the floor. Her curves were framed perfectly against the plush fabric, her ass round and inviting, her gaze smouldering as she looked at me over her shoulder.

"Get over here and start licking, worm." She called impatiently.

Even though my breath was uneven and my body still aching, I ignored the discomfort and approached quickly, lowering myself between her parted thighs, my hand resting on the sofa as I leaned in to plunge into her inviting rump.