Enigma

Continued from: Guilty Pleasures

[F/m] [F/sissy] [feminization] [humiliation] [spanking] [OTK] [BDSM] [femdom] [Mistress]

It was shortly after Christmas, and I was in the kitchen, preparing breakfast when Russell shuffled in, looking rather flustered. 

"There's a very young and jacked, angry-looking woman in the living room, Andrea," he announced, his voice tinged with confusion and a hint of jocularity. 

I couldn't help but chuckle at his bewildered expression, realizing that he'd never met Skylar before. And...I may have forgot to tell him she appears in the vanilla wing of the mansion from time to time. I guess she must have just finished a session on the heavenly-hash side of the house.

"That would be the Doctor," I explained, rather nonchalantly, all while pouring Russell a coffee. "She's one of my new gals at the Facility." 

"The Doctor?!" Russell remarked with a laugh. "She does, umm...like your medical fetish stuff?" 

"No, honey," I laughed, "she's an actual doctor. PhD in astrodynamics or something." 

"The-hell d'you find her?" Russell spoke, now sounding awe-struck, but not nearly as awe-struck as I was, the night I first met this young enigma of a woman. 

"I think I interrupted something, she just glared at me, and didn't say a thing. Like she was looking right through me." Russell stated, now sounding a bit amused with all of this. 

I will admit, Skylar does possess a bit of a distant glare, robotic looking and a bit spacey. It's like there's about sixteen other conversations going on in her mind, as she's maintaining a conversation with you. 

"It's because her brain is working about ten times faster than yours is, darling." I cooed to Russell, placing a hand on his shoulder. 

"C'mon, I'll show you, and introduce you to her." 

Still clad in her dominatrix leathers and heeled boots, looking every bit the intimidating goddess, she simply lounged by the fire, smoking a weed pen and mumbling to herself under her breath. I whispered to Russell, as not to disturb her. 

"She's running through the 'data' from her latest session, analyzing every detail of her sub's reactions, every nuance of her client's behaviour, and making notes about it."

It's a surreal scene, really - this stunning, powerful woman, lost in thought, her mind working overtime to dissect and understand the intricacies of human submission as a sexual kink. I pause for a moment, watching her in fascination. Her brow furrowed in concentration, her lips moving silently as she processes the her inner dialogue. 

*********************

Meanwhile, inside Skylar's mind: 

My client, a middle-aged man with a successful career and loving family, had broken down in tears the moment I presented him with the frilly pink dress and matching Mary Janes he would be wearing for his spanking. His reaction was fascinating - a raw, visceral display of emotion that seemed to stem from somewhere deep within his psyche. 

As I guided him over my knees and began his spanking, his sobs intensified, mingling with gasps and pleas for forgiveness, yet I wasn't spanking him hard, nor did he require my forgiveness for anything.

It's clear that the humiliation of being dressed like a little girl had struck a nerve, tapping into some long-buried shame or insecurity. But why? What was it about this particular stimuli that elicited such a profound response? 

Was it a manifestation of some childhood trauma, a desperate attempt to atone for perceived failures as a father or husband? Or perhaps it was a way of reclaiming a lost innocence, a chance to experience the unconditional love and guidance that only strict maternal discipline can provide.    

Halfway through his spanking, with his panties down to his knees, I decided to introduce a new element to the scene - a full-length mirror, positioned directly in front of my client as he lay over my lap. 

As I resumed his spanking on his reddening cheeks, I observed his reflection in the glass, noting the way his tear-streaked face contorted with each impact. The effect of the mirror was immediate and profound - his crying became more intense, his body writhing beneath my grip as if trying to escape the image before him. 

It was clear that seeing himself in such a vulnerable, humiliating state only served to heighten his emotional response. But why? What was it about witnessing his own degradation that pushed him over the edge? 

I hypothesized that the mirror acted as a physical manifestation of his inner turmoil, forcing him to confront the aspects of himself he had long sought to suppress. By dressing him as a little girl and subjecting him to a punishment typically associated to misbehaving children, I had tapped into a wellspring of guilt, shame and self-loathing that had festered within him for years. 

The mirror merely served as a catalyst, brining these feelings to the surface and allowing him to experience a cathartic release. As I continued his spanking, I marveled at the complexity of BDSM and the ability it has to break down barriers and expose raw, unfiltered emotions that lay beneath. 

With each snap of my palm against his tender bottom, I could feel him surrendering more deeply to the experience, letting go of the inhibitions and hang-ups that had held him back for so long. By the end of the session, he was a quivering, sobbing mess - but there was a palpable sense of relief in his demeanour, as if a great weight had been lifted from his shoulders. 

I'll make a mental note to incorporate the mirror technique into future sessions, eager to see how other clients might would respond to this potent tool of psychological manipulation.

When I close my eyes I can see the room again, I can smell it. It had a distinct aroma of pink baby lotion. The space was deliberately decorated like a little girl's bedroom, complete with pastel colours, frilly lace curtains, and an abundance of stuffed animals perched on every surface. But the centerpiece, the element that may be adding to the session, was the massive mural adorning the wall above the bed. 

A gathering of Disney princesses, each rendered in vibrant detail, the artwork seemed to watch over the proceedings with knowing smiles and sparkling eyes. I couldn't help but wonder what effect this visual stimulus had on my clients, particularly the men who found themselves in this feminine domain. 

Did they feel as though their spanking was being witnessed by a chorus of giggling, judgmental women, their embarrassment magnified tenfold by the presence of these iconic figures? Was this Mistress Andrea's intention all along - to create a space where our clients' shame and vulnerability were constantly reinforced, even in the absence of a real audience?  

By surrounding our clients with symbols of femininity and innocence, we were effectively stripping them of their adult identities, reducing them to the status of helpless, naughty children in need of correction. 

I'm only scratching the surface of what this world has to offer. There was so much more to learn, so much more data to collect - and I am determined to uncover all of it, one spanking at a time.

***************************

As I cleared my throat, Skylar snapped out of her scientific state. She looked up, startled as if she'd forgotten where she was. "Oh, hello, Mistress Andrea," she said, a slight blush creeping into her cheeks. "I hope you don't mind me making myself at home. I just needed a quiet space to think after my session." 

I assured her it was no problem at all and gestured to Russell, to introduce him. 

"Sky, I'd like you to meet someone very special to me. This is Russell Burnett, the one I've told you about." 

She tilted her head to the side, almost like a synthetic human processing new information. She fixed her distant gaze on Russell, her eyes narrowing to study his face. 

"Mr. Burnett, you used to provide Mistress Andrea with spankings, didn't you?" she blurted out, her voice low and curious. 

"Did you ever position a mirror in front of her?" 

Mistress Andrea

xoxo

Continued in: Scientific Method

Little Spoon

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Pent-Up

Continued from: Why the Long Face?

[F/m] [sissy] [FLR] [chastity] [pegging] [spanking] [cornertime] [humiliation] [sissy husband]

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

[F/m] [sissy] [FLR] [chastity] [pegging] [cuckold] [queen of spades] [humiliation] [sissy husband] [Flight Attendant] [hosiery] [feet]

"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