Pent-Up

Continued from: Why the Long Face?

When we left off with this cute couple, Vanessa was exerting her dominance over her sissy husband, allowing him a small moment of scent-association training after her return from work. The dampness of her hosed-feet, came to rest on Derek's mouth and nose, as she massaged and manipulated his caged cock through his panties.

His arousal and frustration level was nearly unbearable. 

Three days without her guiding hand had left him coiled tighter than a spring, emotions and desires building to a critical point. Vanessa recognized the signs - it was time for a therapeutic intervention. A gentle, soothing phrase escaped her lips as she beckoned Derek to head upstairs and position himself in the corner: "Off you go, my little one. let's take care of everything pent-up, shall we?" 

With a mixture of humility and hope, Derek clicked up the stairs in his Mary Janes, his movements tentative, like a child seeking comfort. He had come to learn within his unique dynamic, that being "pent-up" meant tears would flow from his eyes first, before the chastity tears would flow from his cage. 

As Vanessa ascended the stairs, the commanding click of her heels echoed through the quiet hallway, a solitary sound that seemed to amplify her dominance. Her gaze drifted upwards, fixing on the figure in the corner of their bedroom, awaiting his fate. 

Derek, clad in a patterned and delicate outfit of a little girl, stood with his hands on his head, elbows out. The air was heavy with contrition, as if the very atmosphere itself was infused with shame and humility. 

With practiced rituality, Derek had accessed the dreaded "spanking cart" from their walk-in closet. A simple yet elegant two-tier cart on wheels, containing straps, paddles, hairbrushes, a Lexan cane and plenty of tissues. He knew that before positioning himself in the corner, this needed to be displayed and presented for his wife's selection.

Vanessa positioned herself on the plush loveseat, exposing her hosed thighs in invitation. Once summoned from the corner, Derek turned in response, before mincing towards his wife.

Vanessa's slender fingers extended, helping him out of his dress and bra and sliding his panties down and off. With a pat of her lap, his body conformed to the familiar contours of her strict lap, in this time-honoured position. Her hand found its way to the small of his back with a little pressure, to pin him in place, as her sturdy palm began to soundly spank his bare bum cheeks. 

After a long warm-up over her knees, Derek was positioned on an end-table to be paddled. Vanessa sat comfortably nearby, allowing his anticipation to build and tears to rise to the surface. 

With a deep breath, Vanessa launched into the rhythmic motion, paddling his bare bum in a slow, measured cadence. At first, the impact was reasonable, but as the blows continued to fall, the sounds of pain and pent-up emotion began to mingle, culminating in deep sobbing from Derek. He was crying openly now, like a little girl. 

With Derek's emotional catharsis complete, Vanessa's focus shifted to the next stage of his therapy. From the beside drawer, she retrieved her trusty strap-on harness, the supple leather creaking as she buckled it securely around her hips. 

Next she selected a suitable condom, the crinkle of its wrapper piercing the silence as she tore it open with her teeth. With deliberate slowness, she rolled the latex sheath over Derek's chastity cage, creating a reservoir to capture any cum that might be coerced from his prostate. The unspoken promise hung in the air, Vanessa would milk him dry, relieving his pent-up desires while reinforcing her control over him. 

With a subtle adjustment, Vanessa aligned her body with Derek's vulnerable form, the tip of her strap-on poised at the entrance to his "sissy pussy". The initial penetration was followed by a series of shallow, teasing thrusts, each calculated to tantalize his prostate. 

As Vanessa's thrusts gained momentum, she began to slap his already brutalized ass cheeks, to coax him into vocalizing his feelings. "Tell me darling," she urged, her voice husky with encouragement, "do you enjoy being fucked like a girl?" 

A strangled affirmative escaped Derek's lips, his admission hanging in the room like a confession. "Y-yes, Ma'am...I I-like it..." The words dripped with shame and humiliation, a potent cocktail that fueled Vanessa's passion. 

"I love it when your cage slaps against my clit!" She purred out.

Her strokes grew more insistent, driving poor Derek further into the heart of his degradation, as she crafted another memorable chapter in their ongoing tale of this female-led-relationship. All that was pent-up, had been released. 

Welcome home, Vanessa! 

Derek...you better just stay on all fours, while she gets that condom off your cage and feeds you the contents. And don't forget to thank her for it. 

Mistress Andrea

xoxo

Continued in: Mad Men

Why the Long Face?

Continued from: Fallen Angels

"Why the long face, Derek?" 

Ohhh, right, right. It's because you go to bed every night and look down and see this: 

While your wife is in some layover hotel room, probably doing this:

You wake up in the morning, Derek, and diligently make your bed and tidy your room until it looks like this:

 While your wife wakes up in the morning and diligently addresses something also...

But don't worry, she'll be home soon. 

Do you remember Vanessa and Derek? Goddess Vanessa as I like to call her, and her loving, sissy cuckold husband, Derek. Their storyline began here: Vanessa is a Goddess

God she is stunning! I have a major girl-crush on her and actually let her Domme me one night, with MY wife's permission of course. 

You can read about that steamy session here: I often envy submissives

Since these two have such a unique dynamic, I wondered if I could bring them to life using ethically sourced, text-based image generation. 

I described Vanessa as Cuban, 30 years old, a flight attendant with a proclivity toward hosiery and heels, make-up, grace and poise. 

Ummm...*panty check*

Yep, I think we can work with this version of Goddess Vanessa. 

And what about poor Derek? 

Haha...he looks like a version of Zach from Saved by the Bell. You better not let your wife catch you in those boring boy clothes, Preppy! 

That's better sissy gurl. Get your chores done and the house cleaned before your wife gets home, and make sure you're dressed like a little girl, as she had asked...or you know you'll be in deep trouble!

As the sun rose over the Miami horizon, Vanessa, the ravishing flight attendant, prepared for the final leg home to Toronto.

Her raven-haired beauty gleamed in the blossoming light, her curves accentuated by the fitted uniform she wore so elegantly. Meanwhile, back at home, her devoted sissy husband, Derek, waited anxiously, dressed in a frilly maid's outfit, complete with satin gloves and a headpiece. His heart raced with anticipation as he finished handwashing Vanessa's delicates and ironing her laundered clothing. 

By afternoon, Vanessa's arrival home was imminent. Derek assumed the position, presenting himself at the base of the couch as a willing footstool. As she lifted one foot, then the other, onto his trembling back, Derek couldn't help but emit a sigh of contentment. 

With deliberate slowness, Vanessa slipped off her stilettos, setting them carefully and neatly in front of Derek's nose. The scent of warm leather and musky nylons, mixed with lotion, wafted upward. 

His nostrils flared, drinking in the aroma as he gazed longingly at the insides of her high heels, a spot he knew his tongue would soon be put to use. Vanessa settled in, letting out a satisfied moan as she rested her hosed feet on his back, feeling the warmth of his skin through the fabric of his sissy attire.

Vanessa's weight pressed down upon him, her toes curling gently over his shoulder blades. Derek's mind wandered to the ache beneath his satin panties. The steel confines of his chastity cage seemed to tighten, a cruel reminder of his captivity. The delicate lace trim of his underwear, adorned with tiny hearts and flowers, only added to his sense of emasculation.

The contrast between his restricted cock and Vanessa's carefree sensuality was a constant thorn in his side. Yet, as he breathed in the heady aroma of her stockinged feet, now resting comfortably on his nose, Derek knew he wouldn't trade this humiliation for anything. 

For in this world, Vanessa was queen, and he was but a lowly subject, destined to serve her every whim. 

It didn't quite help his cause however, that she was the queen of a certain suit. 

Welcome back, Vanessa and Derek. We've missed you!

Mistress Andrea

xoxo

Continued in: Pent-Up

Fallen Angels

Continued from: Guilty as Charged

I came to collect the girls from their cells, about an hour after their punishments had ended. I brought them warmed oatmeal cookies at their vanilla clothing, while assuring them the scene was all over. 

As Carley stepped out of the dimly lit cell, blinking in the bright fluorescent lights of the facility, her cramped muscles stretched in relief. Beside her, Cassandra emerged, her lovely features still showing signs of remorse from their shared ordeal. They exchanged sheepish glances, a tacit understanding passing between them - they'd faced a trial by fire, emerging bonded by their secret enjoyment of it all. 

They shed what was left of their prison garb, trading it for the comfort of their normal clothes before returning to the main portion of the home. 

"Do you really hafta go?" Cassandra whined to Carley, as I quietly watched this exchange from the bar. 

"Yes, I better get back to Robbie." Carley replied, causing Cassie to crinkle her nose in defiance. 

 

"Hey, Carley...um...do you wanna maybe hang out sometime or grab a coffee or sumthin?" Her query hung like a tentative thread, testing the waters of their fragile connection. 

I could see Carley's heart skip a beat as mine flooded with a maternal sense of warmth and pride. My eyes immediately glossed over with tears. 

Awwwwww my heart!! My sweet little Cassie. She's asking Carley out on a date!

I held my breath and continued to eavesdrop, anxiously waiting for Carley's response as I'm sure Cassandra was as well. 

"I'd like that Cassie. That sounds lovely, really lovely actually...it's just...there's Robbie, right?"

"Oh just fuckin' bring him too. He'll think he's won the lottery. Here, put your number in my phone," Cassandra boldly offered, handing her phone to Carley as both girls began to giggle. 

This of course led to Cassie's tongue darting into Carley's pretty mouth. I pretended I was polishing glasses at the bar while the two stole a final little make-out session, just as I heard Robbie's car pull up the driveway. 

As Carley stood, enveloped in Cassandra's gentle embrace, soft words were whispered against her ear. "I don't want you to go, Carley. Stay with me for a little while longer?" Carley reveled in the sweet pressure of Cassandra's arms, but eventually pulled away and headed towards the door. 

As the door closed behind Carley, Cassandra turned to me, her vision blurred by unshed tears. "Andrea," she murmured, her voice trembling like a leaf. "I think I'm falling for her." 

The admission spilled from her lips like a confession, a fragile hope nestled within the folds of uncertainty. My maternal instincts stirred and my expression softened, as I opened my arms to enfold Cassandra in a comforting embrace. 

I stroked her hair to calm her turbulent emotions, before ushering her over to the window to let my experience guide sweet Cassie. I nudged her to peer out the window. 

"Watch closely, little one," I counselled, my tone low and infusing confidence. "If Carley turns to look back at you, if she smiles, it will be a sign - a signal that her heart beats in tandem with yours." 

With bated breath, Cassandra leaned forward, her palms pressed against the cool glass pane as she scanned the fading horizon. Then, like a fleeting sunrise, Carley's petite form reappeared in the distance, pausing momentarily on the sidewalk. Time suspended as their gazes met across the chasm of space, Cassandra's pulse pounding in anticipation. 

And then, like a promise sealed, Carley's lips curved upward - a gentle smile that conveyed the tender stirrings of her own affection. 

Cassandra spun on her heels toward me, squealing and leaping into my arms, radiant joy illuminating her tear-stained face. 

I have never seen her so happy. 

Mistress Andrea 🥲

xoxo 

Continued in: Why the long face?

Guilty as Charged

Continued from: Ethically Sourced

Here's Carley's conclusion of her fateful day at my Spanking Court, please enjoy and don't mind her eloquence in the language she uses...she's very well spoken ; ) 

Unbeknownst to Cassandra and I, Mistress had an ace up her sleeve when she entertained our pleas of not guilty, concealing a sinister smirk on her face. As it turned out, one of her gentleman clients, who sees her to be spanked, is an actual lawyer. Fuck! 

He even looked like a lawyer, with his cheap suit, 900-dollar shoes and a smug look on his face. 

Cassandra, my accomplice in crime, stood beside me, her lovely features pale and pinched, her grip on my hand tightening as Mistress Andrea (the Judge) began the proceedings. The charges - anilingus and lewdness - seemed to hang in the air like an unspoken promise, each syllable imbuing me with a sense of illicit thrill. 

Cassandra attempted a futile defence of herself, pleading with the court and making me blush in the process, when I heard her describe my own little bum hole. 

"The room was dark. I thought it was her pussy because she's so beautiful and pink back there."

"And the first time you made her cum, Miss Goth, is it safe to assume you knew it was her vagina then?" The lawyer attacked. 

"I was just cleaning it and it went off." Cassandra plead in her own defence.

After that line dropped, I glanced to Mistress Andrea who was doing her best to fight-off a giggle-fit behind the bench. 

"You were cleaning Miss Chapman's vagina and it just went off?" The lawyer repeated back to Cassie, his own voice cracking with the humour of it all. 

And with that, he bluntly turned to the bench and issued his final statement to the court. 

"The prosecution rests its case, your Worship."

With every fiber of my being screaming 'guilty,' I awaited the verdict, suspended in a state of exquisite butterflies. 

Mistress Andrea read our sentences to the court. I think mine was more lenient as I was only charged as a party to the offence. Nevertheless, I was still assigned 18 strokes of the judicial wooden paddle on my bare bum, and two months probation. 

Poor Cassandra, who still gripped my hand tightly during sentencing, would be receiving 36 strokes of the cane on the bare, and four months probation. 

Both sentences, to be carried out immediately before the court. 

The spanking bench, with its buckling leather restraints was produced, along with the caning stockade and finally the dreaded implements. A wicked thrill coursed through my veins like liquid fire, mingling with dread as I beheld the polished surface of the wooden paddle. My imagination ran wild with visions of not sitting comfortably for a week, and - dare I confess it? - a certain shameful exhilaration. 

The guards assisted us in removing our remaining dignity, the protective layers of clothing. Pants, then panties - each item surrendered like shed petals - until we were both naked from the waist down. A low whimper escaped my lips as reality crashed home; I would soon present my quivering flesh to the merciless gaze of the court. 

The guard's grip tightened on my upper arm, as I was lead to the spanking bench and restrained. 

The Judge's nod set the wheels of fate in motion, and with a deliberate slowness, the executioner approached, armed with the wooden paddle. 

Stroke after stroke followed until we reached the full 18, each one meticulously spaced to ensure maximum suffering. Tears pricked at the corners of my eyes, threatening to spill forth in a deluge of surrender. Yet even amidst this maelstrom of pain and humiliation, something perverse within me was thrilled with each brutal caress of the paddle. 

With my paddling complete, I was released from my crucible of correction and summarily deposited onto a hardwood pew of the courtroom, the unforgiving surface biting into my spanked bottom. From here, I was forced to sit quietly and witness Cassandra's ordeal unfold. 

My heart went out to my fellow transgressor, as the pretty guard flexed the cane in her hands, so sleek and unforgiving. 36 sizzling strokes followed, leaving her bare bum a network of fine lines, raised across her skin like stripes of shame. 

Amidst the fiery storm of pain and discipline, her very core responded with instinctual surrender, releasing a silken rivulet of arousal that glistened across her exposed pussy. My mouth watered at the spectacle before me, itching to explore the tender folds of her most intimate area. If only the constraints of the courtroom could be shed, I'd ravage her right on the spot. 

Alas, we soon found our wrists and ankles encircled in cold metal shackles, as we were led bare bottomed from the courtroom. Ball gags came next, an intrusive presence that muffled our whimpers of desire for each other. Locked securely into our cells, shackled and gagged. The court seemed to anticipate how we'd feel toward each other, after this ordeal, and decided to add this additional layer of torture. Jailed for one hour, to reflect on our punishments in silence. 

From my vantage point however, all I could reflect on was the area of the cellblock that I could see from my cell, and the sign that hung above it, illuminated with the words: 

"FEMALE PROBATION AREA"

The area looked like a stage, complete with directed lighting and a microphone boom, elevated and facing several rows of spectator seating. 

My stomach sank with a familiar sickness of butterflies as drool bubbled from my gag. I laid eyes on the apparatus that made up the centerpiece of this stage...

Female probation...

Written by: Carley Chapman 

Continued in: Fallen Angels