Country Roads, Take me Home

Continued from: Tara Gregory: Revelations

[F/f] [mature] [age regression] [babygirl] [strapping] [woodshed] [cornertime]

It would seem that naughty little tart, Tara Gregory, has been completely stealing my thunder with her step-Daddy stories and using A.I. to eclipse my original works. 

Well, let me get my eclipse glasses on here, sweetheart. Two can play at this game! 

*****

The phone on my desk buzzes, interrupting my morning yoga. I take a deep exhale before answering, my voice cool and collected, ready to address whatever request the day brings.

"Good morning, this is Mistress Andrea speaking." On the line, I hear the familiar voice of Cassandra, my ever-efficient receptionist. "Nancy called, Ma'am. She has requested an appointment for the woodshed, the usual story with her, right, a good whuppin from "Daddy"...shall I confirm?"

With a satisfied smile, I nod, already envisioning the scene. "Yes, Cassie, please schedule her in for tomorrow afternoon. And remind her to bring the necessary outfit. 

As I hang up the phone, I rise from my pose and walk over to the window, gazing down at the ominous woodshed in the back garden. The sunlight filters through the trees, casting dappled patterns across the mossy ground. Tomorrow, my beloved client, Nancy, will be marched out to the shed in shame, dressed in her demure, county-girl attire. A simple gingham dress and socks with sandals, to truly tap into her age regression desires. As usual, I'll be playing the role of her farm-hardened "Daddy". 

The next day, the appointment hour arrives. Dressed in her usual Sims outfit, Nancy strides sheepishly towards the steps of my home. 

I hadn't changed into my role yet. I usually do a more therapeutic and professional consultation with her before we begin, to establish her needs and the reasons she is harbouring for wanting a trip to the strict and unforgiving woodshed. 

It had been a few months since I'd seen Nancy, so after greeting her warmly, we had some tea together and I took a little extra time to make her feel at ease, despite her inevitable fate.

When it was time, I pointed to the corner of the room. Nancy's face was stricken with embarrassment and was about to lift her skirt and lower her panties but I stopped her. Nancy is on the wrong side of 50, she has a successful career and adult children. Although naked cornertime and bare-bottomed cornertime has its time and place, sometimes it can be equally humiliating for an adult woman, to stand and face the walls fully dressed, in her adult attire.

I loosely kept an eye on her for the next 25 minutes, while I changed and got into character. Rather than "marching her" out to the shed as I usually do, this time I kindly asked her to change, do her hair properly and meet "Daddy" outside. 

This should be deliciously frightening for her, when she sees me waiting like this. And yes, I am wearing that belt for a reason! 

Pretty soon, I hear the sound of her little patent dress-sandals, crushing the pebble walk-way. Nancy walks nervously toward the woodshed, her sundress fluttering in the soft breeze, a vision of innocence and submission. 

I can't help but admire her determination to explore this side of herself. As she approaches, she lowers her eyes in respect, hands clasped tightly in front of her. 

"I'm here for my whuppin', Daddy." She sobs out, as tears pool into her eyes. 

"Nancy," I greet her sternly, taking her trembling hands in mine. "Please remove your dress right here, and place it on the straw bale, then in you go." 

Her palms instinctively clutched her bottom cheeks, clad in little cotton panties adorned with tiny pink flowers, the style a little girl would wear.

Stepping into the dimply lit woodshed, I took a moment to appreciate the ambiance. The air smelled faintly of damp earth and aged timber, lending an organic quality to the space. Cobwebs lace the corners of the ceiling, and shafts of golden light pierce the darkness through the gaps in the weathered planks. My heeled boots echo on the uneven floorboards as I lead Nancy inside. 

As I close the door behind us, the soft thud resonates in the silence, amplifying Nancy's apprehension. She looks around at the various implements hanging on the walls - straps, paddles, canes and whips - each with its unique purpose and effect. My gaze sweeps over her petite frame, noting how her braided pigtails contrast sharply with the harsh reality of her impending punishment. Her hands are clenched tightly, knuckles white, as she tried to suppress her anxiety. 

Her breath comes in short gasps as I guide her towards the sturdy oak pillory positioned in the centre of the shed. She hesitates for a fraction of a second, but then lowers her neck and wrists into the crescents, bending over and presenting her pristine bottom for correction. 

I close and secure the top portion of the pillory, applying a brass padlock to the hinged clasp. I move behind her, eyeing her exposed bottom appreciatively. Her round cheeks are milky white and unblemished, save for the goosebumps that have risen in anticipation. I run a hand along the arched expanse of her back, feeling her muscles tense beneath my touch. "You know why you're here, don't you, young lady?" My warm breath and frim touch sends shivers down her spine. 

Nodding and weeping, Nancy confirms her awareness of the awaiting punishment. I pat her gently, reassuringly. "Good girl. You know this is for your own good, honey." 

Reaching for my heavy leather belt, I jingle the buckle free and slide it slowly through the loops of my jeans, the sound seemingly amplified in the quiet woodshed. I double it over, testing its weight in my hand before resting it against her vulnerable backside, allowing her to feel its presence. 

With one final look at my target, I raise the belt high above my shoulder. Time seems to slow as it arcs through the air, landing with a resounding crack against the seat of her panties. Nancy's entire body jolts, a strangled cry escaping her lips - the symphony of discipline and surrender. I watch intently as the first welt rises, a stark line marring her perfect complexion, partially obstructed by the cotton veil of her panties which were offering modesty but little protection. 

I instructed Nancy to count each stroke of the belt aloud, teaching her the value of humility and obedience. With every impact, her cries grow louder, her apologies more fervent. 

Twenty lashes with her panties up and twenty lashes with her panties down. It was a thorough and exhaustive strapping for her. Her bottom is a sight to behold, a beautiful canvass of welts, red stripes and some bruising. 

Like an artist adding the final touches, I used my hand to try and blend out her colour and spread the welting more evenly. 

Once Nancy was released from the pillory, I took her outside the shed as-IS! I took her by the bicep as she used her free arm to wipe her tears and snot, before I led her silently down the pebble path and into the main house. 

I lead her to the designated corner of my living room - nose pressed to the wall and hands on her head. Her reddened bottom points toward the centre of the room, a visual testament to her submission and vulnerability. 

"One hour, young lady!" I declare sternly, listening to her whimper in response to my harsh sentence. 

I sat down and played on my phone after setting her timer, keeping a close watch on this adult woman in my living room corner. She remained motionless, save for the occasional hitching of her chest when she resumed her sobbing. I can't help but feel a sense of satisfaction at her absolute submission, knowing that I am providing her with the escape that she needs. 

Mistress Andrea

xoxo

Continued in: Tara Gregory: Anal Virginity

Tara Gregory: Revelations

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Tara Gregory: Wine Cellar

Continued from: Tara Gregory: Brazen

[M/ff] [family taboo] [step-dad] [DDLG] [Daddy] [little] [babygirl] [BDSM] [kink] [cuckquean] [spanking] [humiliation] [cornertime] [dungeon] [bondage]

**Warning - This story contains taboo, family-dynamic, BDSM content** 

**Everyone depicted in this story and A.I. generated are adults, over the age of 18** 

The sun streamed through my bedroom windows as Daddy snuck into my room this morning and went down on me. Despite my dominant ministrations from the night before, I couldn't help but fall deeply into submission once again, as his strong hands gripped my throat while he ate me out in a diaper position. While I was basking in the afterglow of a powerful orgasm, Daddy announced that he had a surprise for me. 

I immediately rushed to the shower to start the day, and spent the next while dressing like a little girl for him and doing myself up to look like a doll. I selected an innocent lavender dress with little ankle socks and matching heels. I half-assumed the little socks would at least stir his memories of last night. 

A thrill ran through my body at the prospect of another secret shared between us. My curiosity piqued, I obediently followed him as he led me down the unfamiliar wooden staircase to the basement. The air grew noticeably colder, and the distant hum of furnaces gave way to an eerie white noise. My heartbeat quickened in anticipation, each echoing step down the hallway leading us further from the safety of the main house. 

Finally, we reached a heavy oak door that I had never noticed before, hidden amongst the shadows of the storage area. The metal lock clinked open under Daddy's firm hand, and he pushed it aside to reveal a dimly lit corridor. The scent of damp earth and aged wood wafted towards me, making my mouth water in excitement. I had no idea what awaited me beyond this threshold, but I trusted him completely. 

Hand in hand, we ventured down the labyrinth, my breath hitching with every click of my heels. As we rounded the corner, a vast space unfolded before us - a hidden wine cellar!

It's ancient stone walls were lined with countless bottles, casting a warm, golden glow onto the cold, damp floor. But as my eyes adjusted, I saw that this wasn't just any ordinary wine cellar. 

In a far corner of the room, my jaw dropped as I discovered an array of sinister objects that seemed out of place amidst the elegant rows of wine bottles. Racks upon racks of leather whips, floggers, and paddles stood sentinel, their tails swaying as we approached. I could almost hear their whispers of pain and pleasure. To my left, a large cage loomed menacingly, its bars thick and unyielding - a stark reminder of the captivating bondage games that were played here. And to my right, several spanking benches and apparatus, their padded surfaces and strategic restraints promising hours of disciplinary delight. 

The room buzzed with unspoken desires, and my body responded instinctively, my nipples hardening and my pussy growing slick with anticipation.

Standing before the display of dungeon furniture, I felt the weight of Daddy's expectant gaze upon me. My breath caught in my throat as he issued his command: "Strip, Tara." His tone was firm, yet steady, betraying none of the emotions I knew must be swirling within him. I hesitated for only a moment, savouring the mixture of fear and arousal coursing through my veins.

Piece by piece, I removed my articles of clothing, starting with my frilly lavender dress, which I let fall carelessly to the ground. Next came my bra and panties, equally as frilly and adorable. As I slipped those off too, I could feel the cool air caress my bare skin, making goosebumps rise in their wake. My socks and heels followed suit, leaving me standing naked in this clandestine wine cellar.

The combination of being naked and in such proximity to this torture chamber only heightened my sense of vulnerability and curiosity, knowing that I was about to explore a side of myself I never thought possible. I cast my discarded clothing aside, taking a moment to appreciate the sight of my own body, bathed in the dim light of the wall sconces. 

My breasts rose and fell with every shallow breath, my pert nipples stiff and begging for attention. My hips swayed subtly from side to side, and my legs trembled as I anticipated what Daddy had planned for me in this forbidden lair. 

Daddy's commands became increasingly short and authoritative, as if the atmosphere of the room had taken hold of him. He walked over to a sturdy bondage apparatus nestled amongst the wine barrels and gestured for me to come to him. I stepped onto the smooth surface of a platform and positioned my ankles and wrists near the restraints. 

Daddy approached me slowly, savouring the sight of my exposed and vulnerable form. He attached the heavy metal cuffs supported by the frame, securing one ankle, then the other, spreading my legs wide. The sounds of metal teeth clicking into place sent shivers directly to my pussy, as I realized that I was truly at his mercy. Next came my wrists, bound helplessly above my head, rendering me drawn and stretched onto my helpless tiptoes.

I felt the unforgiving rigidness of the metal shackles as they encircled my dainty wrists, holding me in place and arching my bottom invitingly. I whimpered softly, my breaths coming in rapid gasps, unable to tear my eyes away from the various collection of implements that hung nearby, wondering which ones would soon make contact with my defenseless flesh. 

In a swift movement that surprised me, Daddy grabbed a large ball gag from the rack of hanging implements. Without a word, he stuffed it forcefully into my mouth, effectively silencing my protests and pleas. The intrusion made my eyes water, but also heightened my sensitivity to the sounds around me, the wetness between my legs growing more pronounced. 

I squirmed slightly as he fastened the straps behind my head, ensuring the gag remained securely in place. Next, a soft piece of fabric brushed against my face. I blinked rapidly, trying to focus before my world went dark. 

With my vision obscured and my body immobilized, I was acutely aware of every sound that reverberated through the stone chamber. My ears strained to pick up any indication of Daddy's intentions, and I soon detected the unmistakable sound of a flogger being taken down from its rack. The leather tendrils whispered together as he practiced a few swings, the anticipation building within me like a crescendo. 

And then, the agony of waiting was over. The air cracked around me as the flogger connected with my tender flesh, eliciting a strangled cry from deep within my throat. The pain was exquisite, radiating outwards from the point of impact and causing my entire body to convulse. I couldn't believe it. I was being whipped! 

Over and over again, the lashes rained down, alternating between my ass, thighs, back and tits, each strike more intense that the last. My skin burned and stung, yet beneath it all, I could feel the heat of desire pooling inside me. 

With each skillful stroke, my body writhed in ecstatic torment. Unbidden, my hips rocked back and fourth, seeking relief from the fiery ache that consumed me. 

 

I couldn't believe it - I was actually enjoying this! But then, something else happened. I felt a warm, wet sensation between my legs, and I knew with a sudden rush of shame, I was soaking my inner thighs. My juices trickled down my tender folds, creating little strands of connecting precum. I wanted to hide, to curl up a die from embarrassment, but the relentless whipping continued, driving me higher and higher until I was trembling. 

The knowledge that Daddy could see this intimate display, this proof of my submission, only added to my mortification. Yet, deep down, I couldn't deny the twisted pride that swelled within me at having pleased him so thoroughly. 

As suddenly as it had begun, the flogging ceased. For a brief moment, silence reigned supreme, broken only by the sound of my laboured breaths echoing off the stone walls. Then, like a lion claiming its prey, I heard the unmistakable sound of Daddy's zipper being yanked down and his pants falling to the floor. Before I could process what was happening, I felt him behind me, his solid presence filling the empty space. He positioned himself between my spread legs, and the blunt tip of his cock nudged against my dripping entrance. 

With no warning, Daddy thrust forward, impaling me on his rigid cock. I moaned wantonly into the ball gag, my body yielding to his brutal invasion. 

Each powerful stroke sent shockwaves through me, my breasts bouncing and jiggling in prefect rhythm. My hands clenched and unclenched uselessly in their restraints, seeking some semblance of control as he ravaged me.

My remaining senses were overwhelmed - the scent of aged leather mingled with sweat and sex, the feel of Daddy's hot breath on the nape of my neck, the taste of the rubber gag filling my mouth. I was utterly consumed by this experience, and it didn't take long before I felt the telltale signs of a ferocious orgasm. It started low in my tummy, like a distant rumble, before exploding outward like a tidal wave. I screamed into the gag, the sound muffled but still ringing out in the cavernous space. My muscles clenched around him, milking his cock for everything it had, as I rode the crest of pleasure and pain. 

After what seemed like hours of ceaseless pleasure and torment, Daddy finally released me from my bonds. He carefully unlocked the cuffs away from my raw skin, his gentle touch in stark contrast to the brutality that had just transpired. I collapsed onto my knees, my legs feeling like gelatin.  

Lifting me effortlessly into his strong arms, he carried me up the narrow, dimly lit steps leading out of the cellar and toward the ruffled pink warmth of my bedroom. I felt small and delicate in his embrace, my legs weak from exhaustion. 

When we reached the sanctuary of my room, he deposited me onto the plush comforter of my princess bed. I collapsed into a boneless heap, the remnants of my release still pulsing through me. Daddy didn't say a word as he pulled the blankets up to my shoulders, his movements slow and loving. He stroked my tangled hair back from my forehead, his fingers lingering for a moment as if to memorize the contours of my face. Then, with a final squeeze of my hand, he turned and left me alone with my thoughts. 

As the door clicked shut behind Daddy, I couldn't help but let my hand drift down between my legs, tracing the slick trail he left behind. My mind raced with memories of the cellar, the delicious combination of fear, arousal and humiliation threatening to consume me once more. With trembling fingers, I began to massage my clit, replaying every lash of the whip, every thrust of Daddy's cock, in vivid detail. 

Within seconds my body responded eagerly, my nipples hardening to tiny points and my breath quickening. My other hand found its way to my tits, pinching and pulling at the sensitive peak. I imagined myself back in the cellar, bound and helpless, completely at Daddy's mercy. My fingers slipped inside my aching pussy, sliding easily through the slickness that coated my petals. 

I reached for a toy and as I began to fuck myself, I recalled the way Daddy's eyes darkened with lust as he watched my body writhe in response to his dominance. I remembered how his cock felt, slick with my own desire, as he plunged it mercilessly into me. My hips bucked involuntarily, seeking friction against the toy that would send me spiralling over the edge once more. My breaths grew shallow and ragged, as I chased after the fleeting fragments of pleasure that lingered in the wake of our encounter. 

Once the final waves of my post-orgasmic haze subsided, I reluctantly slipped out of bed, my body still singing with the sweet agony of satisfaction. I quickly cleaned myself up in the en-suite bathroom before rummaging through my lingerie drawer for the perfect, skimpy outfit. The lace trim tickled my thighs as I pulled on the baby doll nightie, adding over the knee socks and high heels. I couldn't resist a small giggle at how ridiculously cute I looked. I brushed my hair into pigtails and applied a hint of gloss to my lips, knowing full well the effect it would have on Daddy. 

Descending the grand staircase, I tried my best to walk gracefully in my high heels. The sound of my clicking footsteps echoed throughout the expansive foyer. I approached the living room where I knew Daddy would be, my cheeks flushing with equal parts trepidation and excitement. 

My eyes immediately locked onto Daddy's, drinking in the sight of him sitting comfortably and reading. He stood as I entered the room, admiring my darling outfit selection. Without hesitation, I launched myself into his waiting arms, wrapping my legs around his waist and pressing my body flush against his. 

I could feel his surprise, but also the stirring of desire as I nestled my head into the crook of his neck, inhaling deeply of his familiar scent. 

"Thank you, Daddy," I whispered against his ear. "I love you!"

Tara Gregory 💋

Continued in: Tara Gregory: Revelations