Chastity Stories: Forced Into Chastity 01

July 18, 2023

Forced Chastity for Crossdressers 01

Join me as I navigate the complexities of chastity, seeking redemption and a renewed connection with Emma. This is a story that challenges societal norms, delves into the complexities of human emotions, and poses the question: Can true redemption be found in the confines of chastity?

Lost in the Abyss of Chastity

My name is Tom, and I had a stable life with my wife Emma. But I made a terrible mistake—I had an affair with a colleague named Christine. This decision turned my life upside down.

Once a successful businessman, I found myself lost and in a state of confusion. Emma and I had a comfortable life, living in a beautiful California home, and enjoying our success. But for reasons I still struggle to understand, I threw it all away for a momentary fling.

Emma discovered the truth, and our relationship was shattered. Determined to rebuild trust and address my commitment issues, Emma proposed an unconventional solution—chastity. She believed that by denying me sexual gratification and asserting her dominance, we could rebuild our connection.

Reluctantly, I agreed to embark on this journey, hoping to find redemption and mend the damage I had caused. Little did I know that this path of chastity would lead me to explore the depths of my desires, vulnerabilities, and the true nature of our relationship.

Unveiled Desires

One day I walked in the door after a day at work and was greeted by Emma sitting in our living room with pictures of my affair spread all over the table. She must’ve suspected something and hired a private eye to follow me I thought. This wasn’t your typical affair, the pictures presented me in a dog collar on the floor being led on a leash and being spanked with a long wooden paddle among other things.

” I have certain needs that I just never felt comfortable fully exploring with the woman I loved. This meant absolutely nothing…” I blurted out.

Emma’s eyes burned a cold blue, a blue that showed the hurt and pain.

“You son of a bitch! All these years, it’s always been about what you think or you want. With or without you, that ends now!” she screamed.

Her intensity caused me to freeze.

A Journey of Total Submission

“All these years of putting my life on hold so you could pursue your career from city to city. All to see you run off with some bimbo. I NEVER said no to any of your desires. I refuse to let you turn me into some shrew always wondering where you are or what you are doing.”

“Emma, I never meant to hurt you, and the last thing I want is to lose you. I screwed up big time, I will admit that.” I choked through tearful eyes. I did mean it, deep down I wasn’t sure why I did what I did.

“There’s only one way I see of getting through this. You want what is in these pictures? You’re going to get it, and so much more than you bargained for, but on my terms. true submission, not just playing at it for an afternoon or two.”

I blushed, remembering the times we experimented with the tight plastic cock cage for a day of teasing and fun. It was just a playful game for us, nothing more than a temporary thrill.

“I’ll take your reaction as a yes. Well, that game is going to become your reality. I want complete control over my life back. The only way I see a future for us is if you listen to me 24/7/365. I’ve spent fifteen years supporting your dreams, and where did that lead us? I still love you, and I hope we can eventually find some sense of normalcy. But for now, it’s going to be demanding and degrading for you. This is the only way we can move forward. I understand this is a major commitment, so I had a contract prepared…”

Embracing a New Dynamic

Emma’s voice was firm as she laid out the terms of the contract, presenting me with a stack of papers. My heart raced as I realized the magnitude of what she was proposing. It was a make-or-break moment for our marriage.

“Either we agree to this contract or we go our separate ways,” Emma stated, her eyes unwavering. “If you choose to proceed, understand that your choices will be limited. Think of it as a terms of continued marriage contract, not legally binding but a framework for our future.”

I scanned the pages, my mind racing with a mix of apprehension and curiosity.

“Let me highlight the key points,” Emma continued, her voice steady. “First, you will no longer have access to joint bank accounts or credit cards without my approval. Financial decisions will be under my control.”

“Second, you will be required to wear a cock cage at all times, subject to my discretion. Requests for its removal or any mention of sex will be forbidden.”

I couldn’t help but gulp, my eyes widening at the unexpected terms.

“Don’t worry,” Emma reassured me. “We will still engage in sexual activities, but most of the time, your pleasure will come from a strap-on. Your release will be infrequent, and I will ensure your prostate is properly taken care of for health reasons.”

“Lastly, you will adhere to a specific dress code, including women’s undergarments such as stockings, pantyhose, or tights, unless permission to remove them is granted. Your clothing choices will require my approval, and upon returning home from work, you will report to me for your evening attire.”

I sat in stunned silence, absorbing the weight of Emma’s demands. This was far beyond the playful experimentation we had dabbled in before. It was a complete redefinition of our relationship, with Emma at the helm.

I knew I had a difficult decision to make, one that would shape the future of our marriage.

Sissy's Choice

Emma’s wicked smile grew wider as she rolled out a metal rack filled with an array of garish, feminine dresses. My heart raced as I recalled the joy of dressing Emma in posh outfits and reveling in the finest hosiery.

“And that’s not all,” Emma exclaimed, her voice dripping with anticipation. She revealed another rack, adorned with various maid uniforms in pink, blue, black, yellow, lace, satin, latex, and even leather.

“On weekends, Tom will serve as Emma’s personal maid,” she declared, her eyes glinting with dominance.

Emma handed me the contract, urging me to read through the remaining terms myself. The underlying message was clear: she would take ownership of me completely. I would be at her beck and call, following her every command without question.

“If you demonstrate good behavior, we can reevaluate these terms in a year, once I’m convinced that you’ve truly changed and can be fully trusted,” Emma explained. “I understand that this may seem extreme to you, but deep down, you know that it’s the best way forward. It may be more intense than what you had envisioned in this kind of relationship, but it’s not entirely out of the realm of your desires.”

My mind swirled with a mixture of trepidation and fascination. The contract represented a complete surrender of control, a transformation of our dynamic. I knew that accepting these terms would change our lives forever.

Into the Unknown

“I don’t like the idea of dressing like a woman,” I whimpered, my voice filled with uncertainty.

Emma’s gaze softened, and she reached out to hold my trembling hands. “Honey, it’s an all-or-nothing deal. You’ve dressed me up like your little doll over the years, and now it’s time for me to return the favor. We can’t have half measures in this journey.”

She was right. As much as the thought frightened me, it also excited me deep down. I had dabbled with crossdressing in my teenage years, but eventually outgrew the phase. However, a part of me had always been captivated by the sight of my partners in beautiful dresses, silky hosiery, and high heels.

“If you agree, there’s a pile of clothes and shower accessories in the bathroom. Remove all your body hair below the neck and put on the clothes. I’ll be in shortly to assist you,” Emma instructed.

The options before me seemed unconventional and slightly crazy, but I was convinced that this would be a temporary arrangement. Besides, somewhere in the recesses of my mind, the idea aroused me. Growing up with four older sisters, I had always found assertive women incredibly attractive.

“I love you, and I don’t want to lose you. I understand how much I’ve hurt you, and I want to make things right, whatever it takes, Emma,” I declared earnestly.

Emma’s expression softened, but a hint of dominance flickered in her eyes. “Good, but ‘Emma’ feels too familiar for our new relationship. Many of the other titles seem crude and unrefined. I’ve been doing some thinking, and from now on, I am your Maitresse. Perhaps one day, you’ll earn the right to call me Emma again, but that won’t be anytime soon. Now, get in that shower!” She punctuated her words with a swat from the riding crop she held, which emerged from behind her.

As I stood in the shower, lathering my body with Nair to remove the hair, Emma joined me to meticulously shave my genitals. “Don’t get used to this,” she murmured, her tone a mix of warning and excitement. “You won’t be feeling bare skin down here for a long, long time.”

The Advent of the Chastity Cage

With a mischievous smile, Emma revealed a shockingly short metal chastity cage, barely two inches in length. I watched in awe as she skillfully worked the ring around my balls and slid the snug tube over me, hearing the satisfying click of the lock.

“Now, I believe you understand the depth of your remorse. But rest assured, you have yet to comprehend the extent of your penance. Let’s finish preparing you and get you dressed,” Emma declared with a hint of dominance in her voice.

As I stepped out of the shower, I examined the new clothing Emma held in her hands. She gently slid a pair of powder blue satin panties over my legs, the fabric clinging tightly to the confines of the chastity cage. Next, she rolled up a pair of white floral tights and guided my feet into them, skillfully pulling them up my legs. The sensation stirred a tinge of arousal within me, but the unforgiving cage left no room for expansion. Emma then presented a white slip, followed by a wide white petticoat that settled just below my genitals. My anxiety grew as I anticipated what would come next.

Turning around, Emma revealed a dress that took my breath away. It was a powder blue satin maid dress adorned with bows at every turn. The high lace peter pan collar and the overall design left no doubt that this was far from ordinary attire for a woman. As she dropped the dress over my head, I heard the sound of a zipper and a faint “schnikt” noise, causing me to spin around in surprise.

Trying on my Maid's Outfit

With a triumphant smirk, Emma proudly displayed a small brass key, symbolizing my imprisonment in the maid dress. Kneeling down, she opened a shoebox to reveal a matching pair of powder blue pumps with a modest 3-inch heel. As I obediently lifted my feet and slipped them into the shoes, the familiar “schnikt” sound confirmed that they were locked on as well. The dress, embarrassingly short, barely reached my mid-thigh, while the petticoat added an extra poof. The length prevented me from even catching a glimpse of my feet. I extended my leg to the side and behind me, straining to catch a glimpse of the locked heels and examine my tights more closely. The swirling floral patterns on the semi-opaque fabric confirmed that these were not typical women’s legs.

“I won’t give you girly breasts or makeup just yet, although there will come a day when you’ll beg me for them. Tomorrow, we’ll begin your lessons on walking in high heels. But for now, I apologize for the late hour. I need my satisfaction, and you need to acclimate to your new attire, so you’ll be sleeping in it tonight. Typically, you’ll sleep in the tights—I intend to keep you in them, except when you’re showering. I hope you enjoy them. However, unless you disobey, the heels and dress will be removed most nights.”

It was an unwelcome development, but at least I wouldn’t be compelled to sleep in the shoes.

A Night of Unfulfilled Desires

With a heavy heart, I found myself on my knees at the foot of what used to be our shared bed but was now Emma’s domain alone. She wasted no time in barking her orders.

“You rejected my desire for intimacy, so now you won’t have access to my pussy. Instead, you may beg to lick my ass. Every night before bed, I expect you to kneel and beg to worship my ass.”

“Please, Maitresse, may I lick your ass?” I reluctantly pleaded.

“Yes, you may,” Emma replied. The idea repulsed me, but I consoled myself with the belief that this was just a temporary game and things would soon return to normal. I obediently licked and sucked at her back entrance, the taste distinctly tangy. Catching a glimpse of myself in a floor-length mirror, shame washed over me. Here I was, a distinguished man in my late forties, dressed in a sissy maid outfit, licking my wife’s asshole. After about twenty minutes, Emma shuddered with satisfaction. I held out hope for some form of reciprocation, but as I would soon come to realize, such acts were rare in our new dynamic.

“You are dismissed for bed,” Emma declared, leaving me with unfulfilled desires and a longing for the intimacy we once shared.

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