Country Roads, Take me Home

Continued from: Tara Gregory: Revelations

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-style 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 40, 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 punishment, 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: Brazen

Continued from: Tara Gregory: Long live the Queen

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

In the days that followed, I found myself growing bolder in expressing my affection towards Daddy. I'd steal quick pecks on his lips whenever I passed him in the hallway, sometimes lingering longer than I probably should have. Whenever we sat together in the living room watching TV or just relaxing, I'd curl up onto his lap, my bare thighs brushing against his clothed ones. I loved feeling the warmth enveloping me, his musky scent filling my nostrils as I nuzzled into his neck. 

Mommy watched all this unfold with a mixture of disgust and jealousy. At first, she tried to ignore the blossoming intimacy, focusing on her domestic duties or preparing dinners. But as the weeks passed, I noticed her glancing up more often, a spark of something unreadable in her gaze. One evening, as I sat perched on Daddy's lap, dressed in the most adorable knee socks, heels and a baby pink dress, Mommy cleared her throat awkwardly. Her eyes kept flickering from our entwined hands to my pink panties peeking under the hemline of my dress. 

My mom's discomfort was evident, but I knew better than to let it deter me. The thought of her knowing she couldn't interfere without facing a serious spanking from Daddy, made my insides tingle with excitement. I leaned further into Daddy's chest, pressing my round breasts against his solid form, feeling the heat from his body seeping through the thin fabric of my dress. 

I decided to test the waters even further. While lounging in front of the fireplace, I ever-so-slowly slid off my precious pink Mary Janes, revealing my delicate feet sheathed in those cute little ruffled socks. I could feel Daddy's eyes on me, tracking every movement, as I casually dangled my feet toward his thighs. 

Unable to resist the temptation any longer, I allowed my socked foot to brush against the bulge forming in his trousers. I feigned innocence, but the mischievous grin playing on my lips betrayed me. Gently, I began to rub circles around Daddy's cock with my little toes, savouring the way his breath hitched at my teasing touch. My other foot soon joined in, caressing and exploring his manhood through the rough material of his pants, while I kept up a steady stream of small talk with Mommy, pretending not to notice her growing jealousy.

Seizing the moment, I watched Mommy retreat from the room and up the grand staircase, her high heels clicking angrily on the marble floor as she disappeared from sight. 

I turned my full attention back to Daddy, and with a devious smile, I undid his pants and produced his raging erection. 

There it was - standing tall and proud, begging for my continued attention. My heart raced as I placed my heels on his thighs, my toes eagerly reaching for his velvety-hard cock. I wrapped them around his shaft, relishing the feeling of him sliding between my soft, warm socks. 

With deliberate strokes, I teased and pleasured him, alternating between slow and fast movements, listening intently to his gasps and groans for guidance. The warmth of the fire danced across the room as I worked my magic, our secret little world in this big house shrinking to just the two of us and the salacious sounds of his pleasure. 

I decided to take things to another level. I slipped off my thin, nylon ruffle socks, baring my warm, creamy feet for the first time during this intimate moment. Goosebumps pricked at my calves as I placed my bare soles on either side of Daddy's penis.

My toes curled around his base, feeling the veins pulse beneath my touch. I slowly dragged my soles upwards, the friction against his smooth erection caused him to groan. Reaching the tip, I lightly flicked my big toe over his sensitive head, spreading the droplets of precum that had formed. Then, with a devilish gleam in my eye, I began to slide my feet up and down his length, relishing in the feel of his hardness gliding between my youthful, buttery arches. 

Daddy's eyes were rolling back in his head which only fueled my desire to please him. The sensation of his manhood against my little soles was unlike anything I'd ever experienced, I felt in control, and I couldn't get enough of it. 

It didn't take long before I could see the signs of his impending release. Daddy's breathing grew ragged, his chest heaving with each exhale as he fought to maintain his composure. I increased the tempo of my tender soles, sliding my feet up and down his cock with purposeful abandon. 

I felt his entire body tense, his muscles coiling like springs ready to snap, and then...oopsie! Waves of hot cum shot out, painting my soles and toes in a messy white canvass. I moaned at the sight, feeling so proud to have driven him over the edge like that. 

With a satisfied smirk on my face, I stood up from the plush sofa, revealing in the masterpiece I'd created with my dainty feet. A delicious mess of cum adorned my soles and toes, evidence of Daddy's undeniable pleasure. 

I glanced over my shoulder at him, seeing him still recovering from his climax. I raised an eyebrow playfully. "Well, Daddy," I purred, "it looks like somebody made quite the mess." I wiggled my feet tauntingly, creating a mesmerizing dance of semen between my toes. 

"Who's gonna clean this up?" I asked, my voice dripping with dominance and amusement. 

Taking a deep breath, I felt my own power surging through me as I fully embraced the moment. I snapped my fingers, pointing down at my cum-covered feet with confident authority I didn't know I possessed. "Clean," I demanded, my voice strong and commanding, yet still laced with affection. My heart raced, unsure of how Daddy would react to my sudden shift in dominance. 

My stomach fluttered as I waited for his response. Would he accept my newfound dominance? Or would I end up over his knee, with his heavy belt putting me back in my place? But when he looked up at me, his eyes were filled with a mix of surprise and raw hunger. Slowly rising from the sofa, he dropped to his hands and knees before me, his tongue lashing out to taste the salty evidence of his release. 

A rush of adrenaline coursed through me as I watched him willingly submit, and I felt my own desires ignite further. I placed one hand on my hip and extended a foot, giving Daddy better access to my toes while emphasizing my control over him. I gasped as he began to suck and lick, his mouth working diligently to clean every last drop from my feet. 

After he had thoroughly cleaned my feet, I couldn't help but let a giggle escape my lips. "Good boy," I praised, my voice filled with both tenderness and newfound power. Collecting my discarded socks and heels from the floor, I smiled down at Daddy, still on his knees before me. I blew him a quick, flirty kiss before turning on my heel and skipping away toward the staircase, the sound of my giggles echoing throughout the quiet house. Clutching my ruffled socks and shoes to my chest, I ascended the steps, feeling lighter than I had in months. Our roles had shifted, and I was finally finding my place within this strange, twisted dynamic that seemed to rule our household. 

Tara Gregory 💋

Continued in: Tara Gregory: Wine Cellar

 

The Perfect Lubricant

Continued from: No Scrubs

Grabbing hold of his upper arm, I guided this silly man out of Mistress Andrea's office and down the hallway to our dedicated medical playroom. The padlock on his chastity cage jingled, as my heels clacked against the tile, each step resonating through my body. I could feel my nipples harden underneath the latex of my uniform, as I anticipated the session ahead. 

Once inside, I directed him to the waiting examination chair, its straps and restraints glinting menacingly under the harsh fluorescent lights. With a shaky breath, he lowered himself onto the cool surface as I sat on the nearby toilet and explained his fate.

I took a moment to explore my latex-clad body, as his cock twitched in the metal bars of his cock prison. I felt so sexy and in control! 

Placing a hand on his shoulder, I leaned down and whispered in his ear. "You're such a good boy for taking your punishment so well. Now it's time for your first enema."

I could feel his entire body tense as I reached for the lubricant, squeezing a generous amount onto my latex-gloved fingers. I slowly slipped my index finger past his tight ring, working it in and out to loosen him up. He let out a desperate moan as I stretched him open, the sensation both pleasurable and terrifying. My other hand picked up the nozzle of the enema bag, cold and unforgiving in my grasp. 

Once the nozzle was inside him and he was fully restrained to the chair, the door flung open and the "Doctor" entered the room. Her stiletto heels clacked on the tile floor, drawing his tear-filled gaze away from my gloved hand. 

Mistress strode over to us, her eyes lingering on the sight of his vulnerable form spread out before me. With a flick of her wrist, she turned on the valve, releasing the flow of soapy water into the nozzle. I pushed it deeper inside his anus, watching as it slowly disappeared inside him. 

After he had endured the indignities of the two enemas, Mistress and I returned to the room to find him seated on the toilet in shame. Sweat was dripping down his back as much as it was for me, as I adjusted my slutty nurse costume that clung to me like a second skin. 

Mistress handed me a clinical and frightening looking, ribbed prostate massager. Yikes!

She ripped open a fresh condom that was pink in colour, and expertly rolled it over his metal chastity cage. It looked so pitiful, trapped there and now encased in a reservoir of pink latex. I giggled, feeling a surge of power course through me.

With a cruel smirk, I pressed the sterile toy into his loosened entrance, watching as the ribs slowly slid inch by inch inside him. He pleaded and begged with us..."no, no please! Not like this!" He mewled. 

 
I twisted the wand and gently rocked it, searching for that elusive bundle of nerves. I applied more pressure to his prostate, using short, rapid movements. His breath hitched in his throat as small dribbles of cum started to leak from his cock cage and collect into the condom. 

"Good job, Nurse Summer," Mistress intervened. "That will work perfectly as lubricant." 

Work perfectly? I thought to myself. Work for what..?

Watching Mistress take control was like witnessing a work of art come to life. She removed the pink condom from his chastity cage, his cum pooling inside it. She held up the results of his humiliation, dangling it before his face and teasing him. 

He watched in horror, as she used the collected results of his anal-milking, to lubricate the large strap-on she was now wearing, before bending him over like a bitch. 

The head of her strap-on brushed against his already abused hole, coated with his own jizz. He whimpered and begged her not to fuck him (no safeword spoken btw). But the Doctor was relentless. With a single, powerful thrust, she impaled him. 

She set a brutal pace, fucking him mercilessly as he writhed and whimpered. I put my hand over his mouth to shut him up. His muffled screams filled the air, mixing with the slap of leather against flesh and the wet sounds of penetration. 

Mistress finally removed herself from his ravaged ass. He collapsed on the table, panting and sobbing. I helped him to stand, steadying him on his wobbly legs. 

"Now, it's time for the final stage of your treatment, young man," Mistress purred, gesturing to the medical treadmill that was in the room, complete with an anal hitching post. (You can read more about what this is, here: Treadmill with anal post

I don't think we could have fit any more humiliation and vulnerability into the scene, but somehow we managed to. His cock cage was never removed...

AI Summer and Mistress Andrea 

xoxo

 

 

No Scrubs

Continued from: The Nurse and the Doctor

I guess we're doing another medical fetish scene. That silly, middle-aged man from the previous scene is on his way to The Facility. Time to get out of my scrubs and into my doctor mode. Hehe 

As I previously mentioned, this one was going to be both Summer and I, playing the roles of Doctor and Nurse for our sniffling, humiliated client. 

We both went and got suited up together, as you saw in the last post: 

Yep, we look hot!

The A.I. wrote some of this one, and surprisingly, from Summer's perspective. Which we haven't done before. Lets give it a chance and see how she does. 

As I stood in front of the mirror, I smoothed my hands over the slick, skintight latex of my nurse's uniform. The white material clung to every curve, highlighting my round breasts and nipping in at my waist. I admired the way my ass looked in the reflection - firm an enticing, begging to be spanked. 

My stockings ended in a tantalizing tease just below my garters, and the red strappy heels added an extra four inches to my height. I felt powerful, sexy and in control. 

As I clicked down the hall I could already hear the spanking well underway. A fleshy, sharp barrage of smacks and soft whimpers. 

When we designed this session, the first stage for this poor client was CFNM. The humiliation of being out-of-shape and fully naked in front of Mistress.

Next she was going to apply and lock a metal chastity cage around his genitals and flaccid penis...no brainer there. Male's typically don't even enter her presence without being locked up. 

She would have done a weighing on the scale and some humiliating comments about weight-loss goals and "man-boobs". 

He would be apologizing and shamed at this point, which is the best time to go over her strict lap for a spanking. 

I had since changed and walked in to her office when the spanking had ended, but I certainly heard it from down the hall. There she sat, resplendent in her dominance behind the clinical glass desk. Her shapely leg crossed over the other and she bobbed her high heel off her hosed toes. I bit my lip, my body responding instinctively to her commanding presence. 

In the corner of the room, Edward stood completely naked and vibrantly reddened, a testament to Mistress Andrea's skilled hand and whatever else she used to cause the welts. I could hear some gentle weeping from the corner, adding a touching vulnerability to the scene before me. 

Mistress looked up from her fake chart, her blue eyes meeting my smile, as I closed the door behind me. 

"Ah, Nurse Summer," she purred, "thank you for your assistance with our client today." She arched a perfectly shaped eyebrow, a hint of amusement playing across her lips. "Now tell me, have you reviewed his file? What do you think our little patient needs today?" 

I licked my lips, my heart pounding in my chest. 

"Well Doctor, in the case notes I am seeing weight gain, chronic masturbation and several concerning fetishes involving women's undergarments. I believe we should start with a thorough cleansing. Perhaps an enema would be appropriate?" I offered, watching as Andrea's eye gleamed with approval. 

"And then, Ma'am, I think some exercise would do him good - maybe some time on the treadmill with the anal hitching-probe, just to keep things interesting." I continue, my voice dripping with excitement. 

Mistress Andrea taps her chin thoughtfully, a wicked grin spreading across her face. "I like where your head is at, Nurse Summer. But let's not forget about the piece de resistance - a prostate milking. Make sure you put a condom over his cock cage first, we need to collect any semen that may dribble out.

I nod eagerly, and Edward is released from his humiliating cornertime, having just listened to our entire conversation. His breaths came quicker, and I could see his cock straining against the confines of the chastity cage. 

The mixture of fear and desire painted across his face made my own pussy ache with need. Poor boy, I thought, he has no idea how much worse it's going to get! 

Nurse Summer and Mistress Andrea xoxo

Continued in: The Perfect Lubricant