Sissy Stories: Cuckolded Sissy by Submission 02

August 23, 2023

As the night advances, the spotlight shifts to the unfolding interactions between the characters, unveiling hidden yearnings and exposing vulnerabilities. Amidst whispered confessions and daring gestures, the chapter lays bare the intricate tapestry of relationships that flourish under the cover of darkness.

Sissy's Ache

I lay sprawled at the room’s center, my hair a disheveled cascade over the carpet. The sensation in my hands was slightly dulled from the restraints, yet the pulsating ache against the plastic prison of the chastity cage encapsulated my desire. Will’s chosen confinement only amplified the intensity of my arousal, a peculiar blend of longing and restriction.

The allure of being denied even the ability to achieve an erection by my girlfriend’s paramour was a sensation that stirred me to my core. The chastity cage, though a familiar accessory, took on new meaning when placed upon me by Will’s hands.

This scene played out a couple of days after my restrained encounter on the sofa. This time, their intimacy was focused on passionate kisses rather than explicit acts. There was a unique intensity in witnessing my girlfriend tenderly kiss him – an act so intimate that it surpassed even their physical connection.

Here I was, now on the floor, my limbs slightly sore from the constrained position I had been in. The neatness of my hair’s re-tied ponytail contrasted with its previous tousled state. Gradually, I rose with a muted groan, the stiffness in my muscles reminding me of the position I had held.

Jennifer and Will reappeared in the room, their arms entwined, a symbol of their connection. Jennifer’s dirty blonde hair, typically cascading to her buttocks, was now elegantly restrained in a low bun. Her white top and form-fitting jeans emphasized her alluring physique. As Will’s hands ventured to her rear, a playful squeeze prompted Jennifer’s laughter. A natural instinct drew her towards him, their lips merging in a passionate kiss, a dance of tongues that spoke volumes of their shared desires.

With their embrace finally breaking, the telltale bulge in Will’s jeans was undeniable. Jennifer’s hand traced over the fabric, eliciting a soft moan from him, his hands still firmly cupping her behind.

Meanwhile, my own locked-away manhood strained against its confines, a mixture of desperation and discomfort coursing through me. Jennifer caught my gaze, her grin widening. A swift slap landed on Will’s rear, a cue that ceased her playful touch on his erection.

The Cuckold's Nightclub Temptation

We were headed to a nightclub, a trendy hotspot frequented by young, open-minded individuals. It wasn’t exactly a swinger’s club, but it skirted the edges of that realm without fully descending into explicit debauchery.

We’d ventured to this venue numerous times before – sometimes just Jennifer and I, but more often with her lover in tow. On those occasions, I transformed into the third wheel, an eager yet frustrated cuckold who watched from the sidelines as his girlfriend danced, made out, and reveled in the company of her dominant paramour. Although technically her boyfriend, when she was with Will, I took on the role of her cuckold.

As we entered the club, the thumping music filled the air, accompanied by a group of giggling girls who gathered around the entrance. Amidst the energetic atmosphere, a seemingly confident man commanded the attention of the crowd, delivering what appeared to be a public announcement but was, in fact, a display of arrogance typical to this scene.

“The secret, ladies, is in the art of pussy eating,” he proclaimed loudly, his words carrying over the music. “A man who knows how to please a woman down there is a keeper.”

“Robbie, do you eat pussy?” one of the girls called out, her tone a mixture of teasing and amusement.

“That, my dear, is a mystery that remains locked away,” he replied with a self-assured grin and a theatrical flourish.

Inside the club’s dimly lit interior, I finally had a clearer view of Robbie. He appeared to be around our age, perhaps slightly older, his long, straight black hair cascading down to his shoulder blades. At that moment, it was tied back in a ponytail. His attire was as flamboyant as his persona, boasting a garish shirt paired with equally boisterous, distressed jeans. An aura of conceit and ego surrounded him, a familiar disposition that I recognized all too well.

Sissy's Submission Unveiled

“Robbie! Hey there, man. Good to see you around!” Will’s enthusiastic greeting filled the air, earning an eye-roll from me. Of course, he knew Robbie.

Stepping away from the crowd, Robbie approached us with an air of confidence. “Hey, dude. It’s great to run into you here,” he addressed Will before directing a smile at Jennifer, a grin that managed to be both sly and inviting. “And who might this stunning beauty be, gracing your company?”

Will turned, his smile fleeting yet wickedly meaningful, before shifting his attention back to Robbie. “This,” he said, emphasizing the word with a playful squeeze to Jennifer’s rear, “is my friend.” Jennifer’s stifled squeal morphed into a mischievous grin as she glanced back at me. “And,” Will continued, gesturing towards me, “this is her boyfriend.”

Embarrassment crept into my cheeks, a flush of heat accompanying the revelation. Confined within the chastity cage, my arousal mixed with discomfort, the tightness serving as a constant reminder of my submissive state.

Robbie’s smile took on a salacious quality, his tone laden with implication. “Boyfriend, huh? You sure there isn’t a more fitting term for him?”

The humiliation stirred a heightened response within me, my caged penis straining against its confines, a futile attempt at expansion. Oddly enough, I reveled in this sensation. Standing before an audacious stranger who unabashedly recognized my role as a cuckold, his snide remarks only stoked the flames of my arousal. It was a paradox, one that formed the very essence of cuckold relationships – a unique blend of trust, vulnerability, and titillation.

The dynamics were unorthodox, yet we navigated this terrain with a mutual understanding. Jennifer’s respect for my emotions and our shared boundaries was unwavering, a testament to the depth of our connection. This intricate dance, fueled by desire and consent, was our secret, our unique brand of intimacy that both perplexed and enticed.

Sissy in the Swingers' Spotlight

A cascade of dark curls and an array of shimmering jewelry announced her arrival – “Baby! Who do we have here?” Her presence was a vision of allure, her raven-black hair cascading down to her rear, adorned with necklaces and bracelets that glinted a touch too brightly.

She breezed toward us with a wide, welcoming smile, pinching Robbie’s ass playfully before leaning into him, her lips claiming his in an affectionate kiss. Robbie, mirroring the introduction orchestrated by Will earlier, introduced us with a touch of familiarity. My reaction, had I not been encased within the chastity cage, would have undoubtedly been a sticky mess of precum.

Her name was Lana, a captivating beauty who happened to be Robbie’s girlfriend. Their history included a penchant for swinging, a lifestyle that occasionally invited a third participant into their bedroom. As they exchanged animated conversations, I remained a silent observer, a cocktail of frustration, arousal, and denial coursing through me.

Lana and Jennifer seemed to hit it off splendidly, their camaraderie evident as Lana unabashedly praised Jennifer’s figure, playfully patting her enticing derrière. We secured a table for the five of us, or rather, four of them and me, the designated drink-fetcher, dispatched to the counter at twenty-minute intervals. With each departure from the table, Will seized the opportunity to nonchalantly pat my rear, a gesture designed for all to witness. My cheeks burned with humiliation as I embarked on my excursions.

Jennifer reveled in the dynamic, cuddling up to Will and indulging in frequent displays of affection, her lips seeking his or her fingers playfully squeezing his behind. On Jennifer’s other side, Lana sat, occasionally bestowing soft caresses on Jennifer’s backside or delivering compliments that danced on the edge of flirtation.

After an hour of this intoxicating mix of emotions and sensations, Robbie’s demeanor shifted, his posture subtly straightening. Clearing his throat, he seemed poised for something – an announcement, a suggestion, something that I knew was inevitably anticipated.

Sissy's Intimate Gaze into the Swinging Temptation

“We’re interested in getting to know you all better. How about we head to our apartment upstairs? It’s a bit more private,” Robbie suggested with an enthusiastic smile, though it was clear his gaze was fixed on Jennifer and Will.

Jennifer giggled, her playful demeanor infectious as she rose from her seat, tugging Will along. “Took you long enough to ask,” she quipped, her hand landing with a teasing smack on Will’s rear. “Lana and I will go first, and then you guys can follow. Give us a little while – I need to freshen up.”

She glanced at me briefly, a knowing smile playing on her lips. Unspoken yet understood, every move she made was for my voyeuristic pleasure. A pleasure that coursed through me, mingling with the whirlwind of emotions within.

Lana eagerly joined the unfolding scenario, clapping her hands with glee. “Oh, I’m definitely on board with this plan,” she declared, her touch unapologetically roaming Jennifer’s behind, eliciting a delighted squeal.

“How about you and I take this fantastic booty elsewhere, baby?” Lana teased, her intent palpable.

Jennifer’s snicker carried a blend of excitement and amusement. Leaning in, she boldly grabbed a handful of Lana’s ass, her voice a husky murmur. “Absolutely,” she responded, a promise laced in her words. As they exchanged that charged moment, their lingering glances and the trail of smiles they cast my way were an acknowledgment of my presence in their dynamic.

Robbie’s cough served as a transition, bringing attention back to the unfolding conversation. “So, how long have you been a cuckold?” he inquired, a question that left my face flushed once again.

Yielding in a Tangle

“Yeah, I guess so,” I responded, my voice carrying a hint of uncertainty.

His grin widened, as if he had expected my answer. “Good. Stand up and turn around.”

Accustomed to being given orders, even though they ignited a mix of emotions within me, I complied eagerly. Rising to my feet, I pivoted slowly, every movement taking on a heightened intensity, as though the room’s energy had become concentrated. Will remained off to the side, casually sipping his drink with an air of smug satisfaction.

Our table occupied a corner, offering us a semblance of privacy within the bustling club. It was a discreet haven where our interactions remained unseen by the curious eyes around us.

Facing the wall, I waited with bated breath, the anticipation amplifying the persistent undercurrent of sexual excitement that pulsed through me.

Approaching from behind, Robbie gently tugged at my ponytail. “How long have you been growing your hair out?” he inquired softly.

“About ten years or so.”

He let out a low whistle. “That’s quite a commitment. Perhaps overcompensating for something?”

My caged penis twitched, the discomfort of its constraints mingling with the fervent arousal that surged within me. Despite the mild pain, my heightened state left little room for such sensations to deter me.

His hands deftly gathered the length of my hair, his fingers sliding through the dark strands. “Will mentioned he selects styles for you, almost like a hair dominant.”

“Yes, that’s right,” I admitted, my voice wavering slightly under the weight of the admission.

“Do you enjoy it?” Robbie probed further, his tone carrying a note of demand.

Caught off guard by the directness, I stumbled over my response, eliciting an immediate sharp swat to my ass.

“Answer me, cuck,” he insisted, his dominance asserting itself.

“Yes, I enjoy it,” I managed to reply.

“So, you’re willing to let me fashion your hair however I desire?” he pressed, his amusement evident in his voice.

“Yes, I will,” I conceded, feeling the weight of his satisfaction in every word.

Chastity Cage Trembling

He gathered the midpoint of my ponytail, deftly securing it with another hairband. Stepping back, he instructed, “Turn around now, cuck.”

As I pivoted to face him, I noticed that his own hair had been released, likely employing his hairband to tie mine.

With a slight lean, he reached around and brought my now double ponytail forward. The tips of my hair brushed against the tip of the chastity cage beneath my jeans, a sensation that sent shivers of both discomfort and arousal through me.

Robbie seemed content with his handiwork, his smile confirming his satisfaction. Sweeping his hair away from his face, he directed his attention to Will. “Shall we not keep our captivating ladies waiting for too long?”

Will’s nod signaled his agreement. Downing his drink in one swift motion, he stood up, exuding an aura of quiet dominance.

Completing the tableau, Robbie reached over and patted my rear with a condescending familiarity. “Why don’t you settle the tab here and join us in a few minutes, cucky?”

I managed a nod in response, my voice suspended in the grip of my heightened arousal. My penis throbbed insistently within its plastic confinement as I watched the two alpha figures walk away. The promise of an intriguing night lay ahead, wrapped in a cocktail of desire and submission.

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