Les Misérables

Continued from: Dream Team

Remember Remy, everyone? The sissy schoolgirl from France. Well he's back to finish off his experience with my real girls. This is Remy’s current predicament, in  the presence of my three minions, with his little penis safe and secure within the confines of a chastity cage. 

The room fell silent as Remy walked into the classroom, his Mary Jane heels clicking on the linoleum floor. All around him, he saw gorgeous women - tall, curvy, confident - dressed identically to him. 

Each one seemed to radiate an air of superiority that made him shrink even further into himself. When Mistress Andrea called on him to introduce himself, he stuttered out his sissy name of, Lena, with his eyes glued to the floor in front of him. 

"And what brings you to our all-girls institution, Remy?" she asked sweetly. 

Remy's face flamed with embarrassment as he mumbled something about wanting to learn how to be a girl. Mistress Andrea's eyebrow arched at his answer, clearly unimpressed. "Is that so?" she purred, circling him like a shark. "Well then, let's start with a demonstration. Show the real girls your chastity cage, dear." 

With a sinking feeling in his stomach, Remy reached down to lower his panties and lift the hem of his skirt, exposing the baby pink cage that encased his tiny penis. Laughter erupted from the other women as they pointed and jeered, some of them even pulling out their phones to snap pictures. 

Tears pricked at the corners of his eyes, but he didn't dare cry - not here, not like this. Instead, he stood there, frozen as Mistress Andrea continued to berate him, her words cutting deeper than any knife ever could. "Look at this pathetic excuse for a man! This is what happens ladies, when you enjoy dressing up as a naughty little schoolgirl."

Remy suddenly noticed that all the desks were equipped with a large, realistic and veiny dildos, standing at attention before the other women in the room. 

As the lesson began, Remy couldn't help but stare at the monstrous cock affixed to his own desk. His heart raced as Mistress Andrea announced that today's lesson would be focused on manual and oral pleasures. The girls all giggled, but Remy's poor face was white with embarrassment. Over the next hour, Summer, Nancy and Carley all helped their new sissy classmate to jerk off the dildo with his hands and how to use his mouth and tongue to explore its length and girth. 

When it came time for Remy to demonstrate what he'd learned, he found himself paralyzed with fear. The thought of kneeling before these beautiful women, opening his mouth wide and taking that massive dildo inside...it was too much. He shook his head, muttering a feeble protest. But Mistress Andrea wouldn't hear of it. Grabbing him roughly by the arm, she dragged him to the front of the class, positioning him on his knees. 

"You will learn to be a girl, little sissy," she growled, raising a wicked paddle high above her head. 

The crack of wood meeting flesh echoed through the classroom as Andrea brought the paddle down hard on Remy's exposed bottom. He squealed like a little girl, his body jolting forward with each strike. The women watched eagerly, some even cheering her on as she continued the brutal paddling. By the time she was finished, his pale skin was a deep crimson colour, dotted with angry white splotches and bruises. 

Sobbing openly, Remy finally obeyed and began to suck the large dildo while the girls cheered and called him names. 

 

When his humiliation had reached its apex, Remy was escorted to the Principal's office by Mistress Andrea. Her stern grip on his upper arm led him down the hallway, passing curious glances from other teachers and students. He wanted nothing more than to crawl into a hole and disappear. The door swung open, revealing a well-lit room filled with the scent of old books and leather. Principal Jones sat behind his mahogany desk, a cruel smile playing across his face as he took in Remy's sissy appearance. 

He gestured towards the corner of the room and told him how to position his feet and arms. 

Tears streamed down Remy's face as he was now alone in the office with this strange man. The sound of a zipper sounded like a chainsaw in the quiet room, followed by the wet, rhythmic slapping of a palm against an engorged penis. The Principal was masturbating at his desk, while admiring the view of Remy in the timeout corner. 

Remy was pulled from the corner by the cruel Principal, his eyes downcast as he tried to process the situation. Never in his wildest nightmares had he imaged himself in this position - kneeling before another man, his own tiny caged penis a mockery of masculinity compared to the impressive cock before him. 

"Take it in your hand, girl," the Principal ordered, smirking at the look of revulsion on Remy's face. Slowly, trembling, Remy reached out and wrapped his fingers around the warm, velvety length, trying not to cry as he began to stroke it tentatively. 

Eventually Principal Jones leaned back on the desk and spread his legs wider. "Now, sissy," he purred, "I want you to put that pretty mouth of yours to work." 

Swallowing hard, Remy leaned forward, the tip of the Principal's cock brushing against his lips. He closed his eyes, steeling himself for the worst. 

But then, the strangest thing happened: instead of feeling repulsed, he felt...excited? Desperate? Hungry for more cock? He didn't know why, but suddenly all he wanted was to please this powerful man, as he could feel his penis growing hard inside his mouth. 

In a moment of pure desperation, Remy looked up at Principal Jones, tears pooling in his eyes. "Please Sir," he begged, his voice cracking with need. "Please fuck me like a girl." The words left his mouth before he even realized what he was saying, but once they were out there, there was no turning back. 

Beneath the harsh fluorescent lights of the Principal's office, Remy was bent over a counter, his plaid skirt lifted and his panties pulled down to his ankles. The sounds of feminine laughter and excited whispers filled his ears, as the real girls entered the room to watch him be claimed by this dominant male figure. Each time Principal Jones thrust deep into his tight, unwilling hole, the pink chastity cage would rattle and slap about between his thighs, reminding him of his status as a "man". 

He could feel the head of the Principal's cock hit his prostate, sending sparks of pleasure to his growing penis, only to be snuffed out by the rigid cage that kept it limp and lifeless. 

Carley, of all people, who was watching the fucking intently, cried out in encouragement, driving the other girls into a fit of laughter and excitement. "Cum inside him!" she yelled it again. The heat of Remy's embarrassment flooded his face as he felt the Principal begin to tense-up, and then, with one final thrust, he released himself deep into Remy's asshole. The sensation of hot jizz filling him up was indescribable - both humiliating and thrilling at the same time. 

As he pulled out, leaving Remy gasping and trembling on the desk, the girls erupted into applause, their voices ringing in his ears like a symphony of sissy shame.  

****

Thank you to the real Remy for his collaboration and content on this one. He ended up messing around with his own face and an AI image generator to create the following. This is how Remy actually dresses, behind closed doors, when he is Lena - the chaste sissy gurl. Please enjoy:

 

Mistress Andrea

xoxo

Continued in: Choose your own Adventure

Dream Team

Continued from: The Tears of the Sissies will Water the Meadows of France

The day had arrived for Remy, the sissy boy from France, to join the girls and I for his fantasy session. I would be playing the role of the strict Schoolmarm. 

(Not sure what I'm doing with my hands in this one)

I arranged for one of my older, male, slightly creepy clients to play the role of the leering Principal in this all-girls school. Then, as I stated in the previous post, I put together my dream team of fellow students. Beautiful women who would like nothing more than to tease, humiliate and belittle poor Remy, as the new foreign exchange student. 

Check out my dream team: 

We have Summer.

The bubbly best friend who's skirt is not regulation length, just to drive the boys mental. 

Nancy. 

The more mature, senior schoolgirl who is the leader of this group and close assistant to the teacher. "Assistant" could be synonymous with tattle-tale. 

Finally, the new girl, Carley. 

The goth-girl, maybe the wild-child, believed to be unpredictable. This will be her first playdate at my Facility so I'm not sure what this little pixie is gonna do. She does look great in her uniform though. I can't wait to see what this little sniper is capable of.  

There was absolutely no fuckin' around when this French wiener arrived. I booked him in personally, dressed in my role and wielding a cane. He was booked in through the cellblock area so he could truly appreciate his impending peril. Every stich of his clothing was removed, right down to the little pink, clit cage that he wore to his session. 

This was my view as I towered over him. He was completely hairless below the eyebrows, he lacked muscle tone for a man, and his pathetic little thingy looked like so: 

Ick! We need to get that little clit hidden beneath some panties, forthwith! I seized control of the keys to his little clit cage and locked them away with his boring, boy clothes. 

When Remy originally booked this multi-day session, he wanted to be dressed like the other girls. But just to make things worse for him, I didn't do a full transformation with makeup or a wig. I wanted him to still look male, just to humiliate him further, in the presence of my beautiful girls. 

Appearing outwardly male for day one was my rule, but dressed like a schoolgirl. He will have to show me that he truly wants to be a girl. He will need to behave like one, sit like one and learn how to please men like one, before I'll continue his transformation beyond his mere attire alone. 

Which outfit should we go with? I had three options that fit him. 

Option A:

(Not a huge fan of the shorts, but you can see his locked up little clit-bulge in the front)

Option B:

(It's important that he be in high heels, as he clicks around the classroom)

Option C:

(Look how ridiculous he is, dressed like that!)

Once I get him dressed, he will feel sick to his stomach with humiliation. Then I'll finally present him before the girls and tell him to introduce himself as Lena, his sissy name. 

Poor Lena is going to be in for a long few days! She's already crying and I haven't even caned her yet. 

Stay tuned. 

Mistress Andrea 

xoxo

Continued in: Les Misérables

 

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: Early Days

Continued from: Tara Gregory: Beginnings

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

I remember the early days of moving back home with Mom and her new husband, Richard. I was 20 years old at the time and still carrying some of the essence of my former self, the turbulent memories I had, and the weight of a significant chip on my shoulder. I think I was struggling with conflicting emotions. Was I disappointed in myself, for letting ME down, or was I angry at the world around me, for failing me so miserably?

I didn't quite conform to my new surroundings very eagerly. I was still that rebellious teen, ass hanging out of my shorts, bitchy High Dunks on and my tits and tummy spilling out of whatever I had up top.

Don't I look sweet and innocent? Don't be fooled, it was all a masquerade. I so desperately wanted to be someone's perfect little angel as I once was, loved and cared for, but my horns were still holding up my halo.   

Mom seemed to have found her utopia somehow, her harmonious balance, as she minced around the house like a Stepford Wife in pearls and pantyhose. This isn't the mother I remember, back when she was with my real Dad. I resented this version of her and how content she seemed, I even started calling her Deborah instead of Mom, just to be a bitch. 

I desperately wanted to know what her secret was. What I discovered however, was more than I ever could have imagined. 

After a few weeks in the new house, I could already tell something was different...about her relationship with my stepdad. The day of this revelation eventually came, when Mom tried to explain what a head-of-household (HoH) relationship meant. 

She sat me down on my bed and told me that Richard would be making all the decisions for our family, including disciplinary actions if necessary. 

I was confused and a bit defensive, not understanding why my mom wouldn't have any say in matters pertaining to me. But as I had already witnessed since coming here, she was quite happy with this arrangement. She seemed to thrive under Richard's guidance and protection.

When I asked her why she doesn't stand up for herself, she just looked at me with a soft smile. She explained that she trusted Richard implicitly. He always had her best interests at heart, and she knew that he would never do anything to harm her. Plus, she admitted there was something deeply satisfying about surrendering control to someone else, about letting go of the burdens of decision-making. 

During this same conversation, Mom carefully tiptoed around a term that I had not heard before, domestic discipline. She explained that part of being in a HoH relationship meant submitting to punishments when warranted. These punishments could range from mild lectures to more severe correction, like spanking...

The butterflies in my tummy grabbed-hold of that word and held it, as they fluttered within me. "Spanking"...I mouthed the word quietly back to her, but not framed as a question, I just wanted to hear the word spanking said aloud again. 

I was shocked by this realization. It seemed so unfair that Mom would allow herself to be treated this way. But as she continued to talk, I began to understand that these punishments weren't about abuse or domination. Instead, they were a way for Richard to help my Mother correct her behaviour and grow as a person. On one hand, the idea of surrendering control to someone like this sounded liberating. But on the other hand, the thought of my Mother being disciplined like a child was terrifying...I couldn't believe this world existed, among adults... 

It was a weekend morning, and I had just woken up to the smell of fresh coffee brewing downstairs. I dressed and made my way to the kitchen, expecting to find my mom bustling around, but instead, I heard voices coming from the living room. 

Curiosity getting the better of me, I peeked around the corner and saw my mother standing in the corner of the room, completely naked! 

She had her hands on her head, causing her back to arch and her bare bum to protrude. My heart raced as I wondered what could possibly be going on. 

Then, I heard Stepdad's deep voice behind me. "Ah, Tara, you're awake. Come join us, young lady."

Confused and slightly mortified, I hesitantly walked into the living room. That's when I saw him - Richard was sitting on the couch holding a doubled-over belt in his hand, looking at my mother with a stern expression. 

"Mom?" I managed to croak out, my eyes darting between her and Richard. 

"Tara, honey," Mom turned her head slightly to whisper from the corner, her cheeks flushed red. "I messed up, and now I have to be punished." 

I stared in disbelief. Punished? Like a child? Was this some twisted game they were playing or was this for real? 

Before I could ask any questions, Stepdad spoke up. "Tara, since you're already here, why don't you stay and observe how things are handled in my home? Maybe you'll learn something from it."

Feeling both intrigued and uncomfortable, I sat down on the loveseat across from them. Richard instructed my mother out of the corner to stand in front of him, her hands never leaving her head. 

Mom looked so vulnerable and small in this moment. Her nipples had hardened from the goosebumps on her body, and I could tell she was fighting back tears. 

Richard then instructed her to lay over his lap, exposing her bare bottom and her most intimate areas to my view. Then, without warning, he raised his hand high above his head and brought it down hard onto her fleshy bum. 

Mom let out a sharp cry, her body jolting forward for the impact. I winced in sympathy, watching as my Stepdad delivered several more strokes to her already reddening skin. Each smack echoed through the room, filling the air with the sound of his strong palm meeting her tender bottom.

She was then instructed to drape her naked body over the arm of the sofa, as Richard retrieved and doubled over his leather belt. Tears streamed down Mom's face, and I could see the shame written all over her features. Yet, despite the impending belt thrashing, she didn't try to escape or cover her bottom or protest. She took her punishment like a good, kept wife, just as Richard expected her to.

When he finally finished the strapping, Mom slowly stood up, her legs wobbling beneath her. Stepdad handed her a tissue to wipe away her tears and then pulled her into a tight embrace. 

"I love you, Deborah," he whispered softly. "But you know that doesn't excuse poor behaviour."

Mom nodded, sniffling into his shoulder. "I know, Sir, I'm sorry." 

As they held each other close, I sat there in silence, trying to process everything I had just witnessed. Domestic discipline was clearly a normal part of their relationship, but seeing it play out right in front of me was something else entirely. It was equal parts shocking, fascinating and strangely arousing.

I was suddenly stricken with a flush to my cheeks and unexpected and involuntary arousal, I didn't know what to do but stand and ask to be excused. 

"Mm----may I be excused to my room now?" 

Richard answered me, while still caressing and comforted my naked mother. "Yes, Tara, and please, from now on in this household, call me "Daddy".

That night as I lay in bed, I couldn't stop thinking about what I had witnessed. The sound of my mother's cries and the sight of her naked body so helplessly draped over Richard's lap, played over and over again in my mind. It was a strange mix of fear and excitement that coursed through my veins. 

I slipped my hand beneath the sheets, touching myself gently. 

My fingers traced over my sensitive clit, causing a shiver to run down my spine. I imagined what it would feel like to be in my mother's place, bent over this very bed with my bottom exposed to Richard's wrath. The thought sent a wave through my body.

I continued to masturbate, pushing myself deeper into my folds as I fantasized about the firm hand of Richard, landing on my bare skin. 

Each stroke of my fingers sent a jolt of electricity through me, building up until I finally reached my climax. I'm embarrassed to admit I may have moaned out, "Ohhhh, Daddy",  as I came. As I lay there, panting and satisfied, I knew that this was just the beginning of a new chapter in my life. Things were about to change forever. 

Tara Gregory 💋

  

 Continued in: Daddy's Girl