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

Medical Room?

Continued from: Major Renovations

By special request, we were asked if we had or could do a medical fetish room. Sure we can! I still have the outfit somewhere. 

So does nurse Summer! What a little cutie patootie...

Can you picture her, speaking to you in her French accent while her gloved finger probes cold lubricant into your asshole?

This poor fucker didn't pay for both of us, so he'll have to settle for lil' ole me. 

I was equally skilled with the cold lubricant though, as his legs hung helplessly open and vulnerable in the exam chair. 

Yikes, those were big beads! 😬

This young man was given about an hour head-start on the session, after he took a good thrashing over my knee. His penis was confined in a metal chastity device and his instructions were to clean himself out. 

Here, I'm explaining to him what an enema is and how I'm about to start the flow of warm soapy water into his bowels. He was so horrified and mesmerized he could only apologize and kiss my high heels.

There we go! Nice and full. Let those soap-suds do their job. I explained to him that in my absence, he would be required to give himself a second enema, a flush of clear, clean saline, which I had ready. 

I'll make him hold it in until I can see the beads of sweat begin to form on his forehead and lower back. The urgency to release becoming more mentally frantic. I'll torment him, telling him his cock cage won't be unlocked if he doesn't hold it for me. 

Once I see him broken and begging, this is where I will take my leave. I don't need to hear, see or smell what's about to happen. His instructions are to be fully cleaned out for me, or face severe consequences. His penis remains locked...no additional supervision is needed. 

This was the hour head-start I referenced. It will take him about that long to release, flush and release again, spending a significant amount of time with his thrashed backside on a hard toilet seat. Yes, this was by design. *evil chuckle*

It gives me time to go and change, then the actual session begins, this was all just the logistics phase.

How do I look?  

"I'll remove your cock cage if you suck a dildo on the toilet seat for me..."

How humiliating! He is returned to the scene, where he so recently experienced the sounds and splashes of his own putridity. Kneeling and sucking a dildo for me. 

His simulated and "forced" bisexual, medical scene did not end there. He took more cock for me with those giant anal beads up his ass.  

And of course...there was a a reason why I wanted him cleaned out for me! Look at this desperate little slut.

Well...how did we do? Shall we keep the medical fetish room? I just put on my skin-tight scrubs. 💝

Mistress Andrea

xoxo

Continued in: The Nurse and the Doctor

Emasculation

Continued from: He's so Screwed

When we left off, the girls had taken poor Jeremy's cock and mashed it into a chastity cage that was about the size of an Oreo cookie. And if that wasn't bad enough, they used a threaded dildo attachment to give their submissive some usefulness, all while fucking with his mind and his pre-conceived notions of masculinity. 

Jeremy got the divine honour of fucking Mistress Summer with this thing, rather than his actual penis. But Summer made it very clear that if he chose to fuck her, she would be returning the favour. 

Before this comeuppance was administered however, Cassandra wanted in on the action. The solution these two vixens chose was a dildo gag. A short intruding portion that looks and feels like a realistic penis, went into Jeremy's mouth to gag him, while a lifelike dildo triumphantly protruded from the other side.

This must be dreadfully humiliating for Jeremy. Paying to be in the presence of and serve two shockingly beautiful women, yet reduced to using stunt-cocks to fuck them.

Summer rode him slowly and deeply, making sure her asshole dabbed his nose while she bounced away. Cassie took a firm grip of his nipples like they were reins, and slammed her juicy pussy into his chastity dildo. 

His desperation by this point, must have been unbearable. I'm sure he was begging to be fucked, if it meant he was one step closer to release, to having his cock-cage removed. 

The girls ran a train on him and took turns destroying his asshole with their own stunt cocks!

If he spurted from his tiny device, like a sissygasm from anal only, his cage would not have been removed. After several rounds of ass-fucking from both of gorgeous Dommes, the chastity-gasm eluded poor Jeremy. 

Cassandra was of course pissed-off, she didn't want to remove his cock-cage. I'm surprised she didn't kick his balls again, out of frustration. Rather, they subjected Jeremy to one final torment and made him watch, as Summer and Cassie had sex on the couch. 

Jeremy eventually earned his release, after an hour or so of suffering at the hands of these two beauties. Maybe not the release he was hoping for, but after 10 weeks in chastity, he took what was offered. 

The girls made him stand in the corner and face the walls. They sat close-by to supervise and humiliate him. Jeremy was permitted to masturbate while facing the corner, orgasm into his own palm, then consume his entire load. 

He was then required to turn and thank the dominant duo for the load of cum he just consumed. About five minutes after this, limp and shriveled once again, they had him locked back into his day-to-day chastity cage. 

Was it worth it Jeremy? A 30-second wank into your palm in exchange for humiliation, pain, mental torture, degradation and having your arse raped by these two? I'm hearing that no safewords were used... 

I'm sure you wouldn't trade it for all the tea in China, Jeremy...

As usual, I'll be keeping your chastity key as you return to the vanilla world. When you're ready for more heavenly hash, feel free to book with me again. 

Mistress Andrea

xoxo

 

Continued in: 'Tis the Season

 

 
    

Call me "Sir"

Continued from: Sissy husband Fluffs

Vanessa wasted no time in springing from the bed to access her nightside drawer, housing her strap-on. The sensation of her husband's tongue lapping Anthony's cum from off her bare asshole had her ravenous with sexual aggression. Earlier, she clearly stated she wanted to fuck, it was becoming abundantly clear to Derek that she wasn't done yet!

Anthony, sensing that his role in the evening was nearing its expiration, chuckled awkwardly, suggesting he should leave the two love-birds alone. 

"Anthony baby, I think there's a pair of my husband's old trackies in the top drawer. He doesn't need male clothes anymore, help yourself." 

Derek curls up in a little victim-pose on the bed, his mind races with conflicting thoughts and emotions as he contemplates his heterosexuality in light of the events that just occurred. Orally pleasing a man challenged his deeply ingrained sexual orientation and stirs a potent mix of confusion, humiliation, and curiosity within him.

Feelings of shame and vulnerability wash over Derek as he confronts his own internal conflicts. He questions his identity, grappling with the complex interplay between his innate desires and the expectations placed upon him within the context of his FLR with Vanessa.

"Go downstairs and watch Cocaine Bear, baby, I'll be down soon," Vanessa remarks, kissing Anthony on the cheek as her dildo pokes him in the leg. 

Vanessa's apex-predator instincts re-focus to the prey before her, still curled into a fetal position. 

"Take off your dress and panties sissy." 

As he reflects, Derek recognizes that his submission to Vanessa extends beyond traditional notions of sexual orientation. It transcends societal norms and delves into the intricate realms of power dynamics and surrender. He acknowledges that his obedience to Vanessa’s directives is an expression of his devotion and the trust he places in her as his dominant partner.

In the midst of his introspection, Derek acknowledges the potency of the humiliation he experiences. It is a profound element of their dynamic, testing the limits of his submission and pushing him to confront his deepest fears and vulnerabilities.

As Derek’s legs remain suspended in the air, exposing his vulnerability and submission, his gaze is drawn downwards, forced to confront the image of his delicate knee socks and dainty Mary Jane heels. The juxtaposition of his feminine attire with the act of being penetrated like a girl amplifies the psychological and emotional impact of their play.

With each thrust, Derek’s attention is split between the sensations within his body and the visual reminder of his femininity. The sight of his own legs adorned in knee socks and the dainty heels reinforces his role as a submissive, evoking a profound sense of surrender and further blurring the lines of his once heterosexuality.

Vanessa’s dominant presence looms above him, her gaze fixated on his vulnerable state. She revels in the visual tableau before her, the contrast between Derek’s sissy attire and his experience of being penetrated like a girl igniting a powerful mix of dominance and desire.

For Derek, this moment is both transformative and challenging. The combination of physical sensations, visual stimuli, and his submissive role deepens his surrender, confronting him with the complexity of his desires and the fluidity of his identity.

Vanessa doesn't let up, not with her girl-cock and not with her relentless tormenting of her sissy. 

"Do you wish this was a real cock young lady? Tell me you want a real cock, sissy. Do you wish I was Anthony right now?" Vanessa purred, not letting up. 

Vanessa’s questions hang amidst the moans in the room, eliciting a mix of vulnerability and desire within Derek. The implication of her words penetrates his thoughts, stirring a whirlwind of conflicting emotions.

In a voice laden with submission, Derek responds, his words carrying the weight of his humiliating admission. “Yes, Ma'am,” he whispers, his voice quivering with a mix of longing and surrender. “I wish it was a real cock that was fucking me.”

"Call me 'Sir'", Vanessa snaps, slapping his smooth ass and grabbing his hair. 

"Please Sir, please fuck my pussy. I want your real cock Sir!" Derek gasps out. 

The confession unveils a deeper layer of Derek’s emasculation, exposing his longing for a more authentic experience. It reflects the complexity of his submission and his willingness to embrace both the physical and psychological aspects of his role.

Vanessa’s gaze narrows, her expression a mix of understanding and dominance. She absorbs Derek’s response, acknowledging the depths of his vulnerability and the significance of his longing.

“Your desires are noted, sissy,” she affirms, her voice resonating with authority. “Rest assured, I will continue to guide you through an exploration of pleasure and surrender. The next time you need to be fucked or spanked, Anthony will be doing both!" 

"Yes Sir," Derek cried out between grunts and moans. 

When Vanessa felt her husband had suffered enough, she pulled her strap-on out of his spent asshole and returned his panties to him. 

"Put those back on honey, make sure your cage is showing," Vanessa commanded, before they both attend downstairs.  

Once downstairs, Cocaine Bear was put on pause, while Vanessa again led the conversation about their future dynamics. 

"Anthony huni, my husband and I had a little chat upstairs," she started to explain. 

"That didn't sound like much of chat," he replied with a smirk. Derek's face burned with embarrassment. 

"We decided that in future, if Derek is not meeting your "needs", you have my permission to spank him," Vanessa added, her voice now smoky and devious. 

Vanessa’s suggestion silences the room, introducing a new element of discipline and control to their dynamic. Derek’s heart skips a beat, knowing that the consequences of his actions could now involve not only the disciplinary strict measures from Vanessa but also the firm hand of Anthony.

Anthony takes a moment to consider Vanessa’s proposal, his gaze shifting between her and Derek. He understands the significance of this suggestion, the power it gives him to assert dominance and reinforce Derek’s submission. After a brief pause, he responds with a tone of authority, his voice carrying weight and intent.

“I accept your proposition, Vanessa,” Anthony states, his voice firm. “If your husband fails to meet my expectations or disrespects the boundaries of our dynamic, I will administer the discipline he requires.”

Derek’s heart sinks at Anthony’s words, fully comprehending the gravity of the situation. He knows that his behavior and obedience will now be scrutinized more closely, his actions directly impacting the consequences he may face under Anthony’s hand and probably his belt. 

Vanessa’s eyes gleam with a mix of excitement and anticipation, her dominance asserting itself in this new facet of their dynamic. She nods in agreement with Anthony’s response, acknowledging the power and responsibility he now holds in their relationship.

All had been settled, for the next chapter of sickening humiliation and vulnerability for poor sissy Derek. Throughout this entire ordeal, the keys to his chastity cage never made an appearance. 

They likely never will. 

Mistress Andrea and "Chatty" 

xoxo

Continued in: The Secretary

More of Vanessa, Anthony and Derek is also continued in: "Thank you for Fucking my Wife"