Chastity Stories: Forced Into Chastity 03

July 21, 2023

Forced Chastity for Crossdressers 03

In this riveting tale of submission and redemption, I continue to navigate the complexities of chastity, driven by a desire to find solace and a renewed connection with Emma, whom I now embrace as Maitresse.

Through the trials and tribulations of my submissive journey, I surrender myself completely to Maitresse’s desires. Learning the art of proper submission through curtsies, foot worship, and dedicated service, I find myself willingly entangled in the web of pleasure and fulfillment. As boundaries blur and desires intertwine, I am left questioning the true nature of redemption and the transformation taking place within.

The Desire for Chastity and Humiliation

For several weeks, my life took a surreal turn as I found myself dressing up in the most outrageous uniforms and following Emma’s newfound rule. Unbelievably, I complied with her wishes, performing acts of intimacy without receiving anything in return except for the occasional touch on my aroused state. Despite maintaining appearances in our social circles and family gatherings, I couldn’t help but notice a change in myself—a gentler, subdued version of who I once was.

Attempting to hide the truth, I casually mentioned seeing a marriage counselor to my concerned sister. Yet, the telltale signs of my plight were impossible to conceal, revealed through red stripes even beneath the cover of my black pantyhose.

A Challenging Phase in Our Relationship

As the weeks passed, an intriguing shift occurred in our relationship. Emma, now addressed as “maitresse,” introduced a new level of intimacy where I no longer needed to plead for certain privileges but instead was asked to beg to fulfill her desires, explicitly stated in her own words. This act of devotion, which we playfully called “worshipping her,” became an integral part of our routine.

Though I had the freedom to end this arrangement at any time, a powerful and intriguing masochistic desire within me compelled me to keep submitting to maitresse. This willingness to explore new dynamics was both exhilarating and challenging, especially when, during a casual dinner, I accidentally referred to Emma as “maitresse.” While we laughed it off as a silly mistake, my sister Tiffany’s expression hinted that she might have sensed a deeper meaning behind the slip.

Despite the potentially embarrassing moments, this journey of exploration and surrender has opened new doors in our relationship, leading us to discover aspects of ourselves we never knew existed.

A New Rule of Chastity

As the evening progressed and we returned home, I found myself engaged in worshipping maitresse, embracing the newfound intimacy in our relationship. During this intimate moment, she introduced a new Rules of Chastity that would impact our public interactions. Around people, I was to address her as “maitresse” and use her given name, Emma, as sparingly as possible, except when in the company of friends.

With my lips softly parting in agreement, I tenderly continued to express my devotion while on my knees. This exchange of desires and boundaries allowed us to delve deeper into our mutual understanding, cultivating an enchanting sense of closeness between us.

Later that night as I worshiped maitresse after we returned home she made a new rule that in public around people that I was to refer to her as maitresse, and I was to call her Emma as infrequently as possible except around friends. I muffled an affirmative as I lapped at her on my knees.

A Journey of Reflection and Acceptance

A persistent, dull ache gnawed at me almost constantly, a reminder of the chastity cage that kept my desires at bay. The frustration was palpable, and I longed to break free, to experience a sense of normalcy once more. Yet, the unyielding cage remained, removed only occasionally for cleaning, leaving me yearning for a release that seemed elusive.

Maitresse’s seductive attire and teasing remarks about her desires further fueled my frustration. I could only groan in response, feeling the weight of my commitment to this unconventional journey. She urged me to recognize that a truly devoted partner would embrace her satisfaction, even if not directly through me.

Strangely, as I gazed at myself dressed in a french maid uniform, any resentment towards Emma dissolved. Instead, I directed my anger inward, regretting the years I had taken her for granted, neglecting to cherish the love we shared. In a way, this experience became my penance, a path towards self-discovery and a fresh start with the woman I deeply loved. Accepting this newfound vulnerability allowed me to embark on a journey of reflection and growth, ultimately leading to a profound sense of liberation.

Struggling with Desires

Inside my mind, conflicting emotions played a constant tug-of-war. On one hand, I found myself hating the relentless nature of the pain and humiliation I experienced, yet on a masochistic level, there was an undeniable enjoyment. However, the intensity of this 24/7 experience overwhelmed me. The physical exhaustion from the demanding daily tasks, coupled with a monotonous diet, left my brain reeling, struggling to cope.

Each night, as I attempted to remove my shoes and dress, I felt utterly drained, collapsing into bed, utterly fatigued by the day’s relentless schedule. Emma, on the other hand, underwent a remarkable transformation. She exuded newfound confidence and displayed a toned, alluring physique, adorned in provocatively figure-hugging skirts and dresses that seemed designed to tease and tantalize me, knowing how they ignited my desires. Her choice of leather mini skirts and sheer black pantyhose was a potent combination, driving me wild with longing for the unattainable.

As I navigated this complex emotional landscape, finding a balance between pleasure and overwhelm, I grappled with the evolving dynamics of our relationship, seeking a path of understanding and self-discovery.

The Last Submission

Several times a week, my sister Tiffany would reach out for a casual brother-sister chat, unaware of the complexities hiding beneath the surface. Forced to pretend that everything was ordinary, I skillfully concealed the truth during these conversations. However, her suspicions grew when, during one call, I mentioned Emma’s absence, and she curiously questioned the faint sound of clicking high heels in the background.

Little did she know that those high heels were the locked 4-inch stilettos I was compelled to wear, adding to the intricacy of my double life. In the moment, I brushed off the sound, attributing it to a misunderstanding, yet looking back, I wished I had quickly come up with an excuse about Emma’s sudden return to avoid arousing further suspicion. Feeling flustered at the time, playing dumb was all I could muster.

Juggling the delicate art of secrecy became an intricate balancing act, as I yearned to maintain a sense of normalcy in my family connections while concealing the hidden truths that defined my private world with Emma.

The Desires Within

Massaging Emma’s naked body while confined in the cage evoked both ecstasy and torment within me. The mundane chores and tasteless diet remained far from enjoyable, yet a revelation emerged amidst the verbal and physical teasing – a surprising affinity for the sense of humiliation. Each moment spent worshipping her felt like pure bliss, and the occasional brief humping session against her leg was the closest I came to experiencing intimacy during those initial two months.

As the days stretched on within the confines of the chastity cage, the overwhelming urge to request release for sexual fulfillment became undeniable. My vulnerability reached a tipping point, and the words burst forth from my lips, trembling with need, “Please, I can’t bear this any longer. I crave SEX.” Tears streamed down my face, leaving me feeling more submissive and powerless than I had ever felt before.

In this complex web of emotions, I found myself entangled in desires that encompassed both pleasure and vulnerability, forming a profound dichotomy within my being.

A Tempting Proposition

Emma’s wicked smile sent a shiver down my spine as she dangled an enticing offer before me. After enduring 59 days of submission, she proposed granting me sexual satisfaction, but at a cost. The catch was that I had to agree to a reduction in some of my privileges, leaving me wondering what privileges I even had in the first place.

With a cunning glint in her eyes, she revealed my two options – I could either beg to wear makeup or embrace “girlie boobies.” The prospect of making a choice was both exciting and nerve-wracking, as I rarely had the chance to decide anything in my current situation. However, she was confident that eventually, I would give in to one of these desires, knowing that my craving for release would push me to do so.

Her sinister laughter echoed in the room, a sound I had grown accustomed to during these intense 59 days of exploration and self-discovery. The decision before me felt like a pivotal moment, one that could further blur the lines between my desires and the constraints of this unconventional relationship.

The Unexpected Pleasures of Submission

As Emma presented her proposition, I found myself wrestling with conflicting emotions. While submission and humiliation were becoming increasingly appealing to me, the idea of wearing makeup or fake boobs didn’t quite resonate. However, in those crucial moments, a surprising revelation washed over me—I yearned to submit to her request, to relinquish more freedom, and, above all, to make maitresse happy. Admitting this twisted enjoyment within myself was both shocking and liberating.

Considering my options, I recognized that wearing makeup would not physically interfere with me as much as the idea of donning a bra, making it the more tolerable choice. With determination building inside, I knelt before her, reverently kissing her feet, and softly pleaded, “Please, may I wear makeup, maitresse? I want to feel like a pretty girl.”

The impact of my words visibly moved Emma, and she couldn’t contain her joy, exclaiming loudly, “I love my fucking life!” This unexpected turn of events signaled a profound shift in our dynamic, as I willingly embraced a new facet of my desires, forging deeper into the realm of submission and fulfillment.

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