Difficult Choices

Continued from: Secretary Fantasy

After a wonderful session with my "secretary" Bella, I had a blissful sleep that night. Summer got home late and nuzzled in beside me, her silken jammies caressing and cooling my skin. She was so stealthy that I actually didn't wake up, despite her big-spooning me.  

I was however, woken up this morning by high-pitched squealing and giggling, coming from downstairs...Cassandra must have been back from her date with Carley and Robbie. It seems their date was an all-nighter. My maternal den-mother instinct took over. I can't say I approved of this out-call, impromptu sleepover, she only just met this couple. 

As I entered the room to investigate and possibly scold, there's my wife with her hand around Cassie's throat, giggling and urging her to spill the beans on all the dirty and depraved details of her threesome evening. 

Next thing I know, these two end up wrestling around on the floor and laughing, as Cassandra begins to describe her experience with the British couple. 

"Robbie said he felt faint, cuz we fucked him so hard!" Cassie blurted out. 

"Cassandra Leigh Goth!" I barked at her, trying to force a judgey-face but fighting off laughter at the same time. 

"Whaaaat?" She mewled at me. "You know how much I hate dick! I was only there for Carley."

"Will you be seeing these two again?" I asked, genuinely curious. 

Cassandra just smiled, and bucked Summer off her hips, before declaring that she had to go shower and change, she had a client booked for today. 

I was quite surprised. "Oh...Cassie, you have a booking for today!?" 

"Yes Ma'am. Some dude wants me to kick him in the balls." She abruptly replied, while Summer tickled her and they both laughed. 

"I have three booked for spankings Cassie." I remarked to her. 

"That's ok. He can go in the waiting room with the rest of them..."

 Amidst the renovations dear readers, we reinstated the dreaded waiting room. This time it is a bit more clinical, a bit more judicial, and housed in the cell-block area near the spanking court. Clients are booked in groups deliberately, to amplify their shame and humiliation, as they are made to wait for their session and listen to the sounds from down the hall, of wood and leather meeting bare flesh. 

Their stomachs will twist and sicken with butterflies, as fellow clients will ascend the stage to serve their mandatory cornertime at the conclusion of their sessions. 

Bondage and gags are used in the waiting area, along with spreader bars, to keep glistening female genitals spread and exposed to whomever is sitting across. Male's are spread also, to display the pathetic little nub of a chastity cage, that they are required to wear to their session.

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

Paul was looking down at the floor in shame and dread, but his attention was soon drawn to the central stage. A flushed and tear-streaked mature woman stood, hands on her head, buttocks still crimson from her recent trip over my knee. 

The soft, humiliating sobbing accompanying each of her laboured breaths, served as a stark reminder of what awaited those brave (or foolhardy) enough to seek out my unique form of therapy. Paul's own face burned with empathy as he gazed at the poor woman's spanked bottom. He however, was not here for a spanking.  

His attention was snapped from a mere daydream to his ultimate, fetish nightmare, as Miss Cassandra entered the room. Her saunter and swagger was a whirlwind of dark beauty and unapologetic attitude. 

Fishnet stockings, once the purview of retro pin-ups, seemed reborn on her toned, dancer's legs, paired with bitchy jean shorts and Converse all-stars, that gave her an air of rebellious nonconformity. 

Paul's penis twitched in the confides of its cage as she approached. He drank-in the stunning beauty of this gothic princess, turned Dominatrix.  

"It's time, Paul," she hissed, her nails like daggers, roving over his naked and vulnerable form. 

"I trust you're prepared to make some difficult choices today?" 

Paul nodded in the affirmative, as his restraints were unlocked. His arms and legs flexed in relief, though his gaze remained fixed on Miss Cassandra, mesmerized by the studied cruelty dancing in her eyes. The gag, still lodged in his mouth, was slowly withdrawn, that sent a reservoir of saliva and drool cascading down his chin. With a gentle tug on his collar and leash, Miss Cassandra guided him out of the waiting room and into the unknown depths of her lair.  

"Listen up, because I don't repeat myself. You want out of that chastity cage, the pathetic symbol of your inadequacy as male, than it's going to cost you." Her leather glove cupped and cradled his dangling balls, like a coiling serpent.

"Are you willing to take a full-force kick to the balls, just to experience the thrill of freedom?" The cold calculation in her expression made it clear that she didn't particularly care which option he chose; his suffering was merely a means to an end. 

Tears welled up in Paul's eyes, as the brutal simplicity of Miss Cassandra's proposal ravaged his fragile ego. The sting of her disdain for men, seeped into his pores, infecting him with a genuine fear. Yet, after a moment's hesitation, he politely asked her if she would kick him in the balls, if it meant his penis could be free from the cage. 

Miss Cassandra moved with purpose, securing a gag into his mouth and blindfolding him with a silky scarf. As he stumbled, disoriented, she positioned him in the middle of the room and removed his chastity cage. Cassandra scoffed in disgust and raised her arms like she was using "the force", as his penis sprung to life before her eyes. 

She ordered his legs splayed open with feet firmly planted on the floor, she ordered his hands behind his back, and the silence that followed was oppressive, punctuated only by Paul's ragged breathing and whimpers of what was imminently going to happen. 

Just as his penis reached a fully erected and offensive state, the little Converse all-star connected with thunderous force. WHAM! 

Paul dropped in a heap to the floor, his mind recoiled, registering the sensation of his scrotum essentially imploding. He choked and sputtered into the ball gag, before Cassandra eventually helped him to his feet and into a chair. 

Without gentleness, she guided him toward the bondage chair, its cold leather awaiting his surrender. The restraints were secured with practiced ease, his limbs arranged to showcase his ultimate vulnerabilities. Spread-eagled, his throbbing testicles dangled like ripe fruit, trembling with every twitch of fear. With his blindfold removed, he was forced to watch her unlace her tiny runners and cast them aside. 

Ever so slowly, she reached for a tall pair of Doc Martin boots, black and perfectly polished. As Paul watched on in horror, Miss Cassandra slowly and deliberately drew each lace through the brass eyelets before snugging the strands tightly. 

As Paul was released from the chair, his poor legs surrendered, dropping him to his knees in a posture of abject submission. 

"Mercy, please Mistress...don't make me choose that, anything but..." 

She merely raised an eyebrow, her cruelty unwavering as she outlined the terms of his next choice. 

"Silence! You've been given two options to consider: endure a kick from my Doc Martin's" - she paused to admire the weight of her heavy footwear, - "or, submit to a pegging up your slutty little asshole."  

"This way, no matter what you decide, you'll be fucked like the bitch you've proven yourself to be!" 

Mistress Andrea

xoxo

Continued in: Sinister Intent

 

   

Secretary Fantasy

Continued from: Mad Men

I was going to give this post more of a clever name...but nope. It's a Secretary fantasy, plain and simple.

I did however, learn a new term while I was thumbing around for images for this post. Someone was referring to their page as the "DiD Domain", with lovely pictures of corporately dressed women in extensive rope bondage, tape gags and handkerchief gags; always hosiery, always heels. Then, despite my black hair, I had a blonde moment for a quick second as I thought, "wtf does DiD stand for...?" 

Lightbulb...Damsel in Distress!

I saw a meme once that said: "blame Sunday morning cartoons for my current kinks" .

Fair point...

Check out the below shot. The camera seems to have captured and somehow emphasized the ring-finger of the woman in this image. If this is like a marriage or engagement announcement by this couple, that's pretty friggen cute and creative! 

Speaking of other damsels in distress, let us get back to Bella shall we? I had her dress into something more sexualized that entailed slutty "office" boots. The image below is how the scene ended for my bound and gagged damsel. I'll narrate the juicy details leading up to this. 

As Bella knelt before me, her normally composed demeanour was now fractured by the desperation of her roleplay "script". She clasped her hands together in a pleading gesture. 

"Please, Sir...don't fire me. I'll do anything. Anything at all."

The quaver in her voice was almost palpable, her body language screaming surrender. I leaned in to explain our next steps and after a deliberate pause, I spoke, my tone strict and unforgiving. 

"Very well, Mrs. Goth. You may keep your job - but there will be conditions." Her face lit with hope, only to flush crimson red as I continued. "You will receive a corrective spanking, on the bare, followed by a more...intimate demonstration of your appreciation."

With a reluctant nod, she sealed her fate, acknowledging the terms of our little arrangement... 

As Bella rose from her supplicant position, her trembling legs barely supporting her weight, I issued the inevitable command. "Remove your pants and panties, Mrs. Goth, lets get this over with." 

As I led Bella to the sleek, polished expanse of the boardroom table, her slutty heeled boots clicking against the floor in rhythmic obedience, I couldn't help but admire the vision before me. Her gorgeous figure, attired in such provocative clothing, seemed tailor-made for the debauched scenario unfolding. 

Her slender fingers fumbled at the zipper, hesitant yet resigned, as she shed the confining fabric of her dignity. It was a sight both poignant and surreal - a grown woman stripped of her defenses, about to submit to a punishment more suited to a naughty schoolgirl than a capable, executive secretary. 

I ran my hand over the smooth curves of her bum, usually hidden beneath layers of professionalism, lay bare and vulnerable, framed perfectly but her suspender straps. 

Bella's palms came to rest on the boardroom table, steeling herself for the impending correction. Without being prompted, she bent forward, presenting her bare bottom and blooming princess parts, as she arched her lower back. 

She turned and looked to the corporate office windows, shuddering at the thought of someone witnessing this from the street below. My hand rose, paused, and descended with a resounding crack onto her bare bum. 

Well spanked and contrite, Bella knelt before me as I settled into one of the office chairs. Her trembling hands reached up to grasp the button tab of my pants. From the fly, my substantial strap-on cock sprang forth, hidden beneath my pin-stripes this whole time. 

The velvety grip of her fingers encircled the base, stabilizing the monstrous shaft as she prepared to take me into her throat. 

The sweet and degrading sounds of Bella's sloppy blowjob, echoed through the room. Strings of saliva connecting her lips to the cockhead, was evidence enough that my strap-on was lubricated enough for her slutty pussy. 

Her legs, still clad in stockings and boots, formed a shameless 'V', as I laid her prone on the board table. Her exposed pussy glistened with arousal and trembled in anticipation for the impending invasion. The very same cock that had so recently brutalized her mouth, now menaced her delicate opening. 

In a fluid motion, I flipped Bella onto her tummy and bent her forward. A crisp, authoritative smack landed on her already-spanked backside, reminding her to arch her back like a whore. 

I grasped a handful of Bella's hair, forcing her to look out the window while she was being fucked. Simultaneously, my free hand slapped her bare ass, ensuring that her climax would be entwined with the shame and debasement she felt. 

And then, it happened - a pitiful, helpless cry escaped Bella's lips as her body betrayed her, yielding to the overwhelming sensations of orgasm. I released her hair, allowing her to collapse to the table as she began to giggle in disbelief at just how shattering her orgasm was.

The scene was over. We shared a joyful, tender giggle and a passionate kiss, as we basked in the afterglow of our unique dynamic. 

Hold on a second!

How can Bella be my Secretary? Her daughter, Cassandra, is my actual admin assistant and receptionist...

Hmm...

Maybe I should just get the pair of them together, and back into my boardroom? A little Mommy / Daughter session...what do you think? 

Or maybe a Mommy / Daughter school spanking? The sky is the limit. Let me know what I should do.

Mistress Andrea

xoxo

Continued in: Difficult Choices

 

 

Mad Men

Continued from: Pent-Up

During these early months of warm weather I had certainly been seeing enough of Cassandra, throughout that whole court scene we did. This ultimately culminated in my sweet Cassandra developing big feelings for her newfound girl-crush, Carley. It was adorable to watch. She had the look of her mother in those moments of deep emotion. 

Which reminded me...I actually miss Bella. I haven't seen her in awhile for any form of play, despite her practically begging me over text for a session. With Cassandra now gone on a hot date with not only Carley but Carley's boyfriend too *shakes my head*. Summer was at work for a few days on flights, it seemed like the best time than any to reconnect with my original slave girl, the stunning and elegant Bella Goth. 

But...whatever shall we do? What scene should I construct for her. I have so many options with this beauty. The innocence and vulnerability of knee-socks and a short plaid skirt, as she is made to write "I'm sorry for being a naughty girl", over and over on the chalkboard in my classroom? 

Which would no doubt lead to a trip to the female Principal's office where special equipment is available for her correction. Look how vulnerable and beautiful this set-up is: 

I have a table just like this, with bondage options and a bolster for her naked hips. She's probably quite overdue for a good thrashing on that bare bum of hers. 

Maybe...just maybe we'll end up here. Perhaps the objectification of serving me as a maid would be better for today? She could mince around the house in her heels, feather-dusting and scrubbing on her hands and knees while I leer up her dress and whistle in her direction. 

Pony play seems like too much work for today. I could do deep age regression and dress her up like a precious little girl, she hates those outfits! Hates them, that is, until I draw attention to how wet her pussy gets, after dressing her up like a little doll. 

Ahhh. I've got it! Something she and I haven't played in awhile. I reached for my phone to message: 

What a sweetheart! 

You're about to witness Bella's "Mad Men" fantasy. She will actually flip-flop and start calling me "Sir", when she arrives. We've done this scene before, and with little to no instruction, she'll arrive here dressed perfectly and ready to go. Sexualized but timid, meek and demure, ultra-feminine and a bit of an office tart with the right encouragement. 

I'm playing the role of her misogynistic, dickhead of a boss from another era. A time when it was completely normal to slap your Secretary's ass and call her 'toots'. A time where if she wasn't at a typewriter, she'd be out buying the boss a bottle of scotch, as he burnt through the first one during another liquid lunch with "important clients". 

How do I look? Jacket or no jacket? 

No jacket I think... 

Sure as God's got sandals, my shy and timid Secretary clicked into my boardroom about an hour after I text her. I cleared my throat and braced myself for my very best of chauvinism and toxic masculinity.

"Ahh, Miss Goth, please enter..." I spoke as I began our scene. 

"Good morning, Sir", she meekly responded with her eyes down, "I picked up your dry cleaning on the way in to work." Bella ventured out into perfect character. 

In some of these roleplays, especially this one, it's difficult not to break character and burst out laughing, as I was being such a douche-bag...

"Thanks, Sweet Cheeks." I replied, while putting my feet up on the board table like an a-hole. 

"You know, the senior partners and I were talkin'...that big promotion might be in your future, if you start dressing a little sexier around here..." I said with a chuckle. 

Omg I can't even! lol

My, my ladies, we've come a long way. I apologize in advance for this one, it's just a fantasy scene! 

My dickish comment made Bella blush, but she didn't miss a beat with her role. She let out a ditzy giggle and flipped her hair to the side. "Yes Sir, I'll try harder, Sir." 

I seem to remember an old story on this blog where this young lady named Julie, was blowin' the boss to try to earn that big promotion. She ended up getting a spanking from the boss instead...

Perhaps Bella will end up down that same path today? 

She's a good sport, isn't she?! 

Stay tuned for the conclusion of this one. 

Mistress Andrea 

xoxo 

Continued in: Secretary Fantasy

 

 

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