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

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