Sissy Stories: Cuckolded Sissy by Submission 01

August 23, 2023

In this chapter, we’re introduced to a world where passion and control intertwine seamlessly. We witness the protagonist, a man whose very identity becomes entwined with a life of submissive longing. As the narrative unfolds, we delve into the interactions that define his relationships – a girlfriend named Jennifer and the dominant presence of her lover, Will. Together, they embark on a journey that blurs the lines between pleasure and humiliation, desire and surrender.

Exploring Cuckold Relationships

I observed the two of them sharing an intimate moment across the table. My heart raced, a rush of sensations stirring within me. If I dared to even graze my own arousal, it would have consumed me. Jennifer, my girlfriend, and our confident companion, Will, occupied seats on the other side of the table. Their fingers intertwined, and their lips engaged in a passionate dance.

Just minutes ago, we had all been engaged in casual conversation, until Will casually suggested that I prepare some coffee for them. This request wasn’t uncommon; he often took the lead. His dominant personality was evident, a trait that Jennifer seemed to adore. He was physically imposing, overshadowing even my own athletic build. Jennifer would often playfully point out his superiority, especially when it came to size, alluding to his more substantial physical presence in certain aspects.

While we were both undoubtedly attractive and fit, Will possessed an air of dominance that exuded confidence, even a hint of arrogance. However, I held an advantage in certain features – my flowing hair and well-defined derrière. My hair cascaded down to my waist, a dark, slightly wavy curtain that Jennifer couldn’t resist. She had a penchant for men with long hair, and mine garnered her admiration. Then there was my posterior, naturally curved and more shapely than most men’s. I diligently worked on my glutes, and it showed. Jennifer would seize any opportunity to appreciate my behind, playfully patting, squeezing, and caressing it.

When Jennifer and Will initially became a couple, she confided in me about her attraction to him. Yet, she still held a fondness for my hair and my posterior. She had remarked that despite finding Will undeniably attractive, my hair and backside held a special place in her heart. Will’s hair was long as well, albeit with a slight curl, but not as resplendent as mine, falling just past his shoulder blades.

The Cuckold's Intimate Intrigue

As time went on, it became evident to him as well that Jennifer held a distinct fondness for these physical attributes of mine over his own. Unsurprisingly, this aspect seamlessly woven itself into our complex dynamic. Will took a particular kind of pleasure in teasing me about these traits, often referring to my rear end as ‘voluptuous’ and my hair as ‘delicately feminine’. He claimed it was all in line with my role as a cuckold, a term he playfully used to accentuate my submissive nature. The way he would give my backside an affectionate pat in front of others, friends and even strangers, was designed to provoke me, knowing full well it aroused me deeply. It was a clear symbol of my submission to his dominance.

Occasionally, when he approved of the coffee I brewed or a task I completed, he would administer a firm but playful slap to my rear, accompanied by a compliment. These actions played out in front of anyone present, inducing a mixture of extreme humiliation and an unexpectedly overwhelming arousal within me.

In regard to my hair, he took it upon himself to devise new, slightly effeminate styles for me to wear. This ensured that I rarely left it flowing freely. More often than not, he had me gather it into a low ponytail, though there were instances when he opted for a low bun to conceal its length. He recognized Jennifer’s admiration for my hair and never missed an opportunity to suggest that my luscious locks were merely compensation for my more modest endowment compared to his own.

Jennifer reveled in the subtle ways he exerted his dominance over me, her fascination growing more evident with each interaction. She would observe these encounters with keen interest, her excitement escalating. Typically, these exchanges culminated in their passionate make-out sessions, a display of their undeniable chemistry.

Cuckold's Surrender

On this day, he instructed me to secure my hair into a ponytail using a pink hairband – a subtle symbol of femininity, yet another one of his methods to assert his dominance. Following his directive, I prepared the coffee as ordered. As I carried the cups to the table, an unexpected sight met my eyes: they were passionately entwined, his hands firmly placed on the upper curves of her shapely buttocks. Her long, dirty blonde hair cascaded down, brushing against his hands as they kneaded and explored her alluring rear. I stood there, frozen, the cups clutched in my trembling hands, my mouth parched, and my arousal growing undeniable.

Their embrace finally broke as they noticed my presence. Will flashed a mischievous grin and remarked, “That was quick. The only thing you do quicker than cum is make coffee.”

Jennifer’s laughter tinkled through the room, her touch languidly tracing his hair before sensually tracing a path to his earlobe. With deliberate slowness, she traced her way towards his waiting lips.

“Come here and place those cups down. Then return to the kitchen to clean up,” Will directed, his voice carrying a tone of commanding authority.

My arousal now almost painfully evident, I moved towards the table. Will wasted no time, resuming his fervent kisses with my girlfriend just as I set the cups down. As I turned to head back towards the kitchen, he extended his hand and casually patted my buttocks with an air of condescension.

In the kitchen, I spent nearly ten minutes tidying up the remnants of our earlier activities. The entire time, the distinct sounds of their amorous exchanges – kisses, caresses, and impassioned movements – echoed from the living room. As I neared the completion of my tasks, washing the final couple of cups, a subtle stir of movement reached my ears.

Sissy's Submission

The two of them strolled in, Jennifer’s soft giggles echoing in the room, triggered by something Will had shared. “Hey, sweetheart, just wanted to check how much longer you’ll be,” Jennifer inquired.

I continued washing the cups, not bothering to turn my head. “Almost done, Jen,” I replied, my voice steady despite the lingering tension.

Suddenly, a hand cupped my rear, squeezing possessively. “Don’t you think our cucky’s bottom has become plumper these past few weeks?” Jennifer’s laughter rippled through the room, her tone filled with a mix of playfulness and affection. “Enough, Will. My baby’s derrière is flawless,” she added, her voice a soothing counterpoint to the teasing.

Another hand tenderly caressed my opposite cheek, a gesture of intimate familiarity. Will’s amused chuckle broke through. “Well, yours is too,” he quipped, the slap of a hand meeting flesh punctuating his words. Jennifer’s delighted squeal followed, the sound swiftly melding into the renewed symphony of their kisses.

With the cups nearly cleaned, I could have stopped, but I continued scrubbing, the arousal and the undeniable humiliation fueling my determination. The passionate sounds of their affectionate interaction fueled my desire even further.

The two of them separated after a couple of minutes of fervent kissing and fervent touching. Gradually, Will’s footsteps drew near as he positioned himself directly behind me. His fingers ventured upwards, gently threading through the length of my hair. “His hair has grown quite long, hasn’t it?” His observation, no doubt intended for Jennifer’s ears, hung in the air.

I knew Jennifer’s eyes were on us, her fascination mounting with each display of his dominance. It was an intricate dance we had grown accustomed to. She thrived on his control over me, and I understood that this seemingly innocuous exchange was merely a prelude to a night of intense intimacy – for them, at least.

Her murmured agreement was a signal, the anticipation palpable, and the tension building as we navigated the complex dynamics that both challenged and aroused us.

Sissy's Surrender

He tugged gently at the hairband securing my ponytail, his other hand gathering the cascade of hair and folding it up near the base of my skull. “I think tomorrow you’ll be wearing a tight, low bun,” he declared with a trace of dominance in his tone, his fingers expertly manipulating my hair before letting it cascade down once more. His touch was both commanding and possessive.

The waves of my hair brushed against my rear, nearly concealing it from view as he straightened them out. Amid this, a playful pinch landed on my buttocks. “Come on, cucky. Living room. Now,” he instructed.

Turning on his heel, he walked toward the living room, Jennifer following suit, her movements graceful and confident. I trailed behind them, a deliberate distance separating me from their intimate proximity.

As we entered the living room, Will’s hand found its place on Jennifer’s rear, a natural and intimate gesture that accentuated their connection as a couple. With a subtle gesture, Jennifer indicated for me to recline on the sofa, my bare back coming into contact with the plush fabric. A sense of anticipation mingled with an underlying trepidation filled the air.

She momentarily disappeared into our bedroom, reappearing with restraints in hand, her intentions evident. I quickly shed my clothing, the room’s ambience heavy with tension. Will’s smirk was unmistakable as his eyes settled on my aroused state. He advanced, his fingers encircling my erect shaft, a teasing squeeze following. “Even when aroused, it’s so small,” he remarked, his words laced with playful derision. The truth was, I was of average size, but in comparison to Will’s more generously endowed physique, my own dimensions paled in comparison.

Jennifer’s laughter intermingled with the atmosphere, her amusement evident. “You’re getting him even harder, Will.”

His chuckle reverberated through the room. “It’s not going to make him any bigger, though, will it?” His taunting humor underscored the undeniable reality of my submissive arousal.

Beads of precum adorned the tip of my penis, a visible testament to my intense arousal. Climbing onto the sofa, I positioned myself as instructed, my bare skin making contact with the fabric. The softness of the material contrasted starkly with the intensity of the situation. The subtle sounds of Jennifer’s movements in the kitchen filtered through, signaling the impending initiation of their carefully orchestrated encounter.

Cuckold's Chastity Vigil

I came to the realization that there would be no release for me on that day. Within mere seconds, an icy sensation encased my engorged member, causing it to rapidly diminish in size. Soon after, a frigid, plastic enclosure enveloped my penis and testicles, while Will manipulated a device with practiced ease. In just a minute’s time, the chastity cage was securely locked in place, rendering my manhood imprisoned. The erotic intensity of the situation was undeniable – my girlfriend’s lover had, quite literally, imprisoned my penis.

Meanwhile, Jennifer had been occupied with securing my restraints. Once she had completed her task, I found myself immobilized, my hands and feet bound, and my now-caged penis at the mercy of their desires.

Unable to free my hands, I was left incapable of any self-soothing over the plastic barrier that confined my manhood. Will’s laughter filled the room as he toyed with my vulnerability. Taking a position beside the sofa, he reached under my head and brought my ponytail to the fore. Playfully, he brushed the ends of my hair against the cage that held my arousal captive. “Perhaps if your hair was a tad longer, you might have found some pleasure, huh, cucky?”

Jennifer’s gaze remained fixed on this spectacle, her lips slightly parted in astonishment. If her heightened arousal could be gauged by any physical sign, it would have been a telltale droplet at the corner of her mouth.

Leaving me in my bound state on the sofa, they arranged themselves comfortably on the loveseat across from me. The initial hour was consumed by their passionate embraces and fleeting conversations. As the TV flickered to life, the passage of another hour saw their affections evolve into something more visceral. Will and Jennifer’s bodies intertwined, their movements a symphony of passion. I could witness their shifting positions, their kisses infused with fervor. They traversed the range of lovemaking possibilities, a testament to their genuine connection.

Decorated cock cage

For the next three hours, I lay there, an immobile spectator to the intimate connection between Will and Jennifer. With the passage of time, I ceased attempting to catch glimpses of their actions, instead focusing on the symphony of sounds that told their own story.

As their fervent encounter concluded, Will approached the sofa. His semi-erect member was a testament to their activities, and his hand bore the remnants of his recent climax. His malevolent smile was directed at me, a silent promise of further humiliation. In a single, deliberate motion, he streaked his own essence across the surface of my chastity cage. His grip shifted, seizing my ponytail before he rotated my body, positioning me face-down. The feeling of his warm semen being rubbed onto my buttocks filled me with both degradation and arousal.

Amidst the charged atmosphere, Jennifer neared, their soft kisses mingling with the air. “He looks so utterly submissive lying there,” she observed, her voice carrying a mix of fascination and satisfaction.

“He does. And I love that your cum adorns his cage,” she added in a hushed tone, her approval evident. A playful slap landed on Will’s buttocks, a silent affirmation of their shared understanding. Their embrace resumed, lips meeting in an intimate dance.

Time seemed to elongate, each passing moment laden with both tension and desire. Will’s condescending hand patted my buttocks, a gesture that communicated his unspoken dominance.

“I’ll be with you again next weekend, cucky. Enjoy your time in the cage until then,” he remarked with a mixture of amusement and authority, a clear indicator of our ongoing arrangement.

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