Alice: Down the Rabbit Hole

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Alice: Through the Looking Glass

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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"

Shattered Masculinity

Continued from: Smooth Reflections

"Don't be shy sweetheart, open your closet," Vanessa mischievously purred to her husband Derek, as he stood in a ridiculous pair of satin panties and ruffled knee socks, ending at pastel pink Mary Janes.

Derek audibly gasped as the closet door creaked open. 

Ruffles, lace, and an abundance of pink dominate the space. The once-dull and monotonous men's wardrobe has been replaced with a kaleidoscope of colors and textures, reflecting his sissy persona.

Vanessa, with a smirk on her face, guides Derek through the treasure trove of garments. She takes great pleasure in presenting each piece, highlighting its unique features and the significance it holds in their dynamic. From frilly dresses to lacy petticoats, the closet tells a story of what is expected of Derek in the future of their relationship. 

Derek's eyes widen with a mix of excitement and apprehension as he explores the feminine ensembles before him. He runs his fingers over the delicate fabrics, feeling their softness against his skin. Each item is meticulously chosen to accentuate his curves, emphasizing his sissy identity and reinforcing his submission.

Vanessa, understanding Derek’s need for deep humiliation, indulges his desire to be dressed as an elaborate little girl. She selects an ensemble with meticulous care, ensuring that every detail contributes to the transformation.

The new outfit, tailored to accentuate Derek’s femininity, features a fluffy, pastel-colored dress adorned with lace and ribbons. The fabric is soft and comfortable, designed to create a sense of innocence and playfulness. She accessorizes the outfit with a matching hair bow, to compliment the frilly socks he was already wearing.

As Vanessa dresses Derek in the elaborate little girl attire, a sense of vulnerability and surrender washes over him. He allows himself to embrace the childlike innocence and playfulness that the outfit represents, willingly surrendering to the nurturing care and guidance provided by his wife.

In this new persona, Derek finds solace and a temporary escape from the responsibilities of adulthood. The transformation into an elaborately dressed little girl allows him to explore a different facet of his submission, finding comfort and security in the role that Vanessa guides him through.

"Go ahead little one, twirl in the mirror for me," Vanessa teasingly cooed. 

Derek's stomach was sickened with butterflies of humiliation, as he took in his full form in the floor-length mirror and performed a twirl. His bottom lip began to tremble as he crawled to Vanessa's lap for support. 

As Derek kneels before Vanessa, with her commanding presence, she poses a thought-provoking question, asking if he deserves to have conventional sex like a “real man” would.

The question hangs in the air, laden with implications and challenging societal expectations. Derek’s heart skips a beat as he processes the inquiry, his mind racing to find an answer that aligns with their unique dynamic. He understands that their FLR encompasses a different set of norms and desires, and conventional definitions of masculinity may not hold the same weight within their relationship.

Derek’s thoughts swirl as he contemplates his response. The chastity cage restrains his desires, reinforcing the control that Vanessa holds over his sexual pleasure. He considers the depth of their connection, the fulfillment he finds in his humiliation, and the satisfaction he derives from serving her in ways that extend beyond conventional notions of sex.

With a mixture of vulnerability and conviction, Derek meets Vanessa’s gaze and answers truthfully, his voice trembles with shame and inadequacy. 

"No Ma'am."

He acknowledges that their dynamic transcends conventional expectations and that the fulfillment he experiences through his submission and service to her far outweighs the desire for conventional sexual encounters.

Vanessa observes Derek’s response, her eyes softening with empathy and understanding. She recognizes the vulnerability it takes for him to acknowledge his limitations within their dynamic. In that moment, she reassures him that his worth and value as a submissive partner are not tied to conforming to conventional expectations of masculinity or sexual encounters.

"This is why I have to fuck Anthony, honey, I hope you understand that?" Vanessa coos. 

With a gentle touch, Vanessa places her hand on Derek’s cheek, imparting a sense of acceptance and reassurance. She reminds him that Anthony should be here soon and that she needs to get Derek's make-up on. 

"Make sure you curtsy and address him 'Sir', as you answer the door sweetheart," Vanessa sternly reminds Derek of the respectful protocols. 

As the doorbell rings, signaling Anthony’s arrival, Derek’s heart races. He takes a deep breath, summoning the courage to step into the next phase of their dynamic. With Vanessa’s guidance, he descends the stairs, his frilly dress fluttering with each step. Her words ring out in his mind, making his tummy ill with butterflies. 

“Remember, sissy, your purpose is to please and serve. Embrace your role and trust in our dynamic.”

With those words echoing in his mind, Derek opens the door, revealing Anthony standing before him. Derek performs a dainty curtsy, his voice soft and submissive. “Welcome, Sir,” he utters, his wispy feminine voice carrying a mix of nervousness and obedience.

Anthony’s eyes scan Derek from head to toe, taking in the sight before him. A smirk forms on his face, a mix of amusement and intrigue. He nods in acknowledgment and steps inside, ready to explore the depths of Vanessa’s desires with Derek as a submissive participant. A participant who was swiftly excused to the corner of the room by Vanessa. 

After some small talk between Anthony and Vanessa, she summons her husband from the corner and asks him to "look after" Anthony. 

Derek approaches, swallowing a lump of jealously in his throat and fighting off tears. 

"May I show you to my wife's bedroom, Sir?" 

As Derek utters his request in his wispy feminine voice, a moment of anticipation hangs in the air. Anthony’s gaze lingers on him, studying the submissive sissy before him. He takes a moment to consider the proposition, understanding the dynamics at play and the power exchange that has brought them together.

With a nod of approval, Anthony acknowledges Derek’s request, his voice commanding yet tinged with a hint of amusement. “Lead the way, little girl,” he responds, his tone conveying a mix of authority and ridicule.

Derek’s heart quickens as he guides Anthony toward the bedroom, his delicate hand gripping Anthony’s firmly. He feels a sense of both nervousness and excitement, knowing that his purpose in this moment is to serve and prepare Anthony to please Vanessa.

As they enter the bedroom, Derek’s submissive nature takes over, and he gracefully takes on the role of Anthony’s obedient attendant. He fetches towels, lubricant and discreetly arranges the room, ensuring an environment that will cater to Anthony’s desires and his wife's pleasures. 

With each subtle movement, Derek's femininity and submission are on full display. He maintains an air of grace and obedience, his voice remaining soft and deferential as he addresses Anthony. “Is there anything else I can do to assist you, Sir?” he asks, his words carrying a mixture of deep shame and humiliation. 

Anthony’s gaze travels over Derek’s delicate form, appreciating the effort and devotion he has put into his sissy role. A smile dances upon his lips as he responds, his voice firm yet appreciative. “For now, sissy girl, your presence is enough. Remain attentive and ready to serve.” Derek dipped into a shallow curtsy and responded. 

"Yes Sir," 

Derek's words trembled from his mouth, as he kneels to wait for the arrival of Vanessa. 

Mistress Andrea and "Chatty" 

xoxo

Continued in: Sissy Husband Fluffs