Sissy Stories: Chastity’s Unforeseen Path03

August 16, 2023

In the third chapter, Adam’s humiliation and submission reach new heights as he serves both his mistresses and the unexpected guest, James. The story delves deeper into Adam’s willingness to obey and perform humiliating acts under the orders of his mistresses. While preparing breakfast and catering to their needs, Adam is surprised by the arrival of his friend James, who becomes an active participant in Adam’s degradation. The scenes escalate as Adam is instructed to unbutton James’ shirt, leading to an intimate encounter that pushes his boundaries, further solidifying his role as a submissive slave. This chapter highlights power dynamics and explores Adam’s newfound sissy identity, immersing him in a world of chastity, obedience, and devotion.

Submission to Chastity

The piercing sound of the alarm clock shattered the morning calm, jolting Adam awake. He squinted at the clock’s display – 7:30 AM. Through the window, the cloudy sky cast a subdued light into the room. Rubbing his eyes, he stretched, only to be reminded of the chastity cage that imprisoned his manhood. The uncomfortable reality of his situation flooded in as he glanced around the room.

He reached for the bowl of water within the cage, sipping carefully as he contemplated the events that had led him here. Just yesterday, he had anticipated celebrating his 25th birthday with friends. Now, he found himself naked, confined to a cage, and wearing a chastity device, his thoughts interrupted by Mistress Grace’s entrance.

“Time to rise, bitch!” her voice cut through his thoughts, and she silenced the blaring alarm clock. As she approached, she unlocked the cage door, prompting Adam’s attention. Her commanding presence loomed over him.

“Kiss my boots and crawl out,” her order echoed in the room.

Suppressing his discomfort, Adam leaned forward, pressing his lips to her boots with subservient obedience. He then crawled out of the cage, muscles protesting as he moved. He longed to stretch, but he knew better than to defy Mistress Grace’s expectations. Recognizing his unspoken need, she granted him permission to stand and stretch, though her stern expression warned against overstepping boundaries.

The morning sun filtered through the window, casting a muted glow on the scene. Memories of his abandoned birthday plans clashed with the reality of his current circumstances. Confined to a cage, wearing a chastity cage of a different kind, and under Mistress Grace’s watchful gaze, Adam’s journey into submission was unfolding. With each command, he found himself navigating uncharted territory, torn between humility and uncertainty.

The Beginning of Mysterious Desires

“Stand,” commanded Mistress Grace. “You have until 8 to shower and prepare breakfast. Be at the reception desk by 7:55 sharp, or face punishment.”

With those words, she revealed a pair of black lacy panties, throwing them onto the floor. “Wear these today. We have a special guest, and they wouldn’t want to see your clitty. Enjoy the surprise, worm!” Her laughter lingered as she exited the room.

Adam’s thoughts raced as he pondered the upcoming humiliation. Who was this mystery guest, and what embarrassing ordeal awaited him? He brushed these questions aside as he stepped into the bathroom, focusing on his tasks at hand.

The hot water of the shower soothed his tense muscles as he washed away his apprehensions. Drying off quickly, he checked the clock and hurried to groom himself. He hesitated for a moment, staring at the black lace panties on the floor. The material seemed surprisingly comfortable and inviting. His curiosity got the better of him as he slipped them on, their snug fit accentuating the bulge of his chastity cage and leaving his rear provocatively exposed. Despite his confusion, he ignored his unexpected arousal and moved forward.

Descending the stairs, Adam’s mind buzzed with worry about the mystery guest. Standing at the reception desk in his newfound panties, his nerves grew. Time ticked away, and his anticipation grew until 7:55 arrived, and Mistress Grace emerged from behind the reception desk, prompting the next phase of his enigmatic journey.

Servant In The Kitchen

“Follow me, dog. We don’t have time to waste,” Mistress Grace commanded, and Adam quickly obeyed, trailing behind her. They turned right at the corridor intersection, likely headed for the dining room. Adam recognized it as the place where he had eaten off the boots of the captivating woman just the day before.

They entered the room, and Adam closed the door behind them. The table lay bare, signaling that his role would involve setting it up. As he turned to Mistress Grace for guidance, she headed through a previously unnoticed door on the left. Adam’s unfamiliarity with the layout yesterday had likely caused him to miss it in the shock of his unique meal.

Curious yet obedient, he followed her into the kitchen, where stainless steel appliances gleamed. Wooden cupboards lined one side, while a sink and cooker occupied the other. Upon the workspace, he spotted a small piece of paper, but he refrained from touching it until given instructions. The anticipation of what culinary tasks awaited him loomed in his mind.

Morning Culinary Duties

You will be making breakfast for Mistress Alice, our guest, and myself. Oh, and I suppose you’ll need to eat as well,” Mistress Grace’s sarcastic tone filled the room. “Our order is on that piece of paper. Make everything as specified and make yourself a two-egg omelette, a slice of buttered toast, and two sausages. These must be ready by 8:30 on the dot. Chop chop,” she concluded before leaving the kitchen.

Adam glanced at the piece of paper detailing the orders:

Mistress Grace: Scrambled eggs, 2 pieces of toast with strawberry jam, 3 sausages, and 2 hash browns

Mistress Alice: A two-egg omelette, 1 slice of toast buttered, 2 sausages, and 4 strips of bacon

Guest: Scrambled eggs, 2 pieces of toast with Nutella, 3 sausages, 3 hash browns, and 4 strips of bacon

With a sense of urgency, he started preparing the meals. The clock on the wall became his reference point as he worked diligently. As the minutes ticked away, Adam focused on cooking the dishes. It was 8:27 when he checked the clock again. He had managed to complete all the orders, including his own omelette and sausages. He hurried to put his bread in the toaster and quickly plated the meals. Just as he finished, Mistress Grace entered the kitchen.

“Bring through the plates one at a time. The guest’s plate will go at the head of the table, and then mine and Mistress Alice’s at either side of our guest’s,” she directed Adam.

Serving Breakfast

Adam carefully brought the guest’s plate into the dining room and set it at the head of the table. His nerves were on edge, knowing that the guest could arrive any moment. He quickly returned to the kitchen to fetch the remaining two dishes. As he entered the dining room with Mistress Grace, he couldn’t help but feel the weight of the situation.

“Now get a dog bowl from the cupboard and put your food in it,” Mistress Grace commanded him.

Obediently, Adam retrieved a dog bowl from the cupboard and transferred his own meal into it. As he focused on his task, he heard movement coming from the dining room.

The Turning Point for Chastity Slaves

“Pick up your bowl and bring it through, slave. You will stand until we tell you otherwise. The guest is going to be quite shocking for you, but do not deviate from what you have learned so far. We’re going to chuck you in the deep end now, bitch,” Mistress Grace instructed, opening the door to the dining room. Adam followed, his heart pounding with anticipation.

Inside the dining room, a tall figure was seated at the head of the table, facing away from Adam. Mistress Alice sat to his right, and Mistress Grace took the left. They all turned to look at Adam as he entered. The sight before him nearly caused him to drop his bowl of food. Seated at the head of the table was none other than his close friend, James.

Frozen in place, Adam struggled to process the situation. James, with his commanding presence and corporate attire, exuded an air of authority that Adam had always respected. James’s dark eyes bore into Adam’s, and his lips curled into a wide grin. The room echoed with James’s deep laughter as he took in the unexpected scene before him.

In that moment, Adam stood humiliated and exposed, confronted by a friend who had seemingly embraced his role as an alpha male. The encounter marked a turning point in Adam’s journey of submission and servitude.

Sissy Shaming

“What the fuck have you become?” James roared, struggling to contain his laughter as he looked at Adam. Adam stood there, silent and submissive, not wanting to provoke any anger from his mistresses or his friend.

“Sit next to your friend, Adam, on the floor, of course,” ordered mistress Alice, motioning for him to come closer. Adam obediently placed his bowl of food on the floor between James and mistress Alice, then knelt down on the floor, his eyes cast downward.

Amidst the awkward and humiliating situation, James continued to address Adam. “This is fucking hilarious, Adam. I got a text yesterday inviting me for breakfast and to witness an old friend’s humiliation, but I was not expecting this. Are you wearing women’s panties?” James asked with amusement.

“Yes, sir,” Adam replied in a quiet voice.

“You can call him bitch boy or slave,” mistress Grace interjected, her tone dripping with superiority. “His test showed that he was a complete, 100% beta male, so he’s worthless, really,” she added, enjoying her power over Adam.

“Eat in silence now, piggy. This alpha doesn’t want to hear your bitching while we eat,” mistress Grace commanded. With that, she grabbed James’s bicep playfully through his suit jacket and began to enjoy her breakfast, leaving Adam to his submissive position on the floor.

Sissy Lifestyle

The four of them ate in silence for around fifteen minutes before mistress Grace spoke.

“Tell me James, you’ve known Adam for a while, but did you think that he would be a beta male?” She asked.

“To be honest I always knew that he was a bit of a beta male, he’d always change in private in the locker rooms and just did whatever we told him, a real submissive.” James chuckled as his words stung Adam.

“Well it’s no surprise that he changed in private just look at that clitty between his legs!” laughed mistress Grace.

James glanced down at Adam who was kneeling on the floor. He turned back to mistress Grace before speaking.

“His dick is so tiny that you can’t even make it out in the panties! You’d think he was a woman with a vagina! I wonder if his penis even grows?” he laughed as he spoke asked mistress Grace.

“Funny you should say that James,” she cooed, “When he went to the testing centre, he only measured 1.8″ soft and the hardest he could get was easily under 4!” all three of the people above him burst into laughter as mistress Grace told the tale of Adam’s premature ejaculation at the testing centre.

“To make things worse, he literally came in under 2 minutes!” mistress Alice chimed in, revelling at the humiliation. The three of them laughed again while Adam bowed his head and continued eating. He was confused and extremely turned on by this and wondered if they had been right all along; that he enjoyed being humiliated. The four of them all continued to eat in silence until they were all finished.

“Take all of the plates into the kitchen slave and leave them in the sink to be washed and then come back bitch.” Commanded mistress Grace.

Exploring Submission

Adam followed the command, carrying the plates with trembling hands and trying his best not to drop them. Mistress Grace’s harsh words echoed in his mind as he carefully placed the pile in the sink. After a quick rinse, he returned to the dining room, only to find an unexpected scene unfolding.

Mistress Alice and James were locked in a passionate kiss, while mistress Grace was busy removing James’ suit jacket. When mistress Grace noticed Adam’s presence, she instructed him, “Get over here, bitch, and undo this alpha’s shirt and tie.”

A mix of nervousness and excitement surged through Adam as he approached the table where James sat. With trembling hands, he untied James’ tie and placed it on the table. Slowly, he began unbuttoning James’ shirt from the top, his gaze fixed on his task. Throughout, James’ lips remained locked with mistress Alice’s.

Adam’s fingers moved methodically, revealing James’ well-defined chest and abs. As the shirt was fully unbuttoned, Adam helped James slip out of it, exposing his muscular physique. Mistress Grace stood behind Adam, guiding his hand over James’ chest and abs, ensuring he felt every contour of an alpha male’s body.

With each touch, Adam’s body reacted, his confined penis straining against the chastity cage. The conflicting emotions of humiliation and desire coursed through him as he continued to explore his submissive role.

Awakening Desires

Mistress Grace’s words hung in the air, stirring Adam’s curiosity. His thoughts raced as he wondered what it would be like to see James’ erect manhood up close. Mistress Grace’s command cut through his contemplation, instructing him to beg James for permission.

“Ask the alpha male if you can,” she said, changing her mind, “Actually no, beg him to let you see his cock.”

Adam felt a mix of anticipation and humiliation as he lowered himself to his knees. His position on the floor was a stark reminder of his submissive role. He faced James, who had shifted his chair back to accommodate Adam’s kneeling form. Their eyes locked, and Adam took a deep breath.

“Sir, you are a complete alpha male, a truly powerful man,” Adam’s voice trembled with a blend of excitement and vulnerability. “It would be an honour if I was allowed to see your penis. Please let me see your cock so that I can learn my place as a pathetic beta worm.”

James chuckled, his amusement evident. “You’re pathetic,” he remarked, but then he rose from his seat, clearly considering Adam’s request.

In a moment of tantalizing suspense, James began to undo his belt, only to pause, leaving Adam on edge, wondering what would happen next.

Sissy's Submission to Alpha Power

James’ demand cut through the air, sparking a mixture of excitement and trepidation within Adam. His hands moved quickly to comply, undoing James’ belt and then hesitating, awaiting further instructions.

“Take off my trousers now, worm,” James commanded.

The rush of submission coursed through Adam as he obeyed. He carefully slid down James’ trousers, revealing his friend’s grey Calvin Klein boxer briefs, which outlined the impressive bulge beneath. Adam’s own arousal was undeniable, his fantasies mingling with the reality of the situation.

Mistress Alice’s voice intervened, gently but firmly reinforcing the significance of James’ presence and his virility. She emphasized the potency of an alpha male’s attributes, underlining how Adam could never replicate the pleasure James could provide. Adam’s submission was reaffirmed, solidifying his role in this power dynamic.

“Your mistresses tell me that you’ll do anything that I say, bitch. Is that correct?” James questioned.

Adam hesitated momentarily, then replied, “Yes, sir.”

James pressed further, challenging Adam’s boundaries. “Even if it was the most humiliating thing ever? Like sucking my cock?”

In that moment, Adam grappled with his desires and his role in this new reality. His response, however, was a testament to his surrender, his willingness to fulfill the desires of a superior man.

“Yes, sir. It would be a great honour for me to suck your cock.”

James’ dominance intensified as he issued his next command. “Good. Take my underwear off with your mouth, bitch.”

The words echoed in the room, igniting an inferno of humiliation and submission within Adam.

Forced Humiliation and Kissing

Adam eagerly complied, moving his mouth towards James’ crotch. He was met with a musky smell, and as he grabbed the bottom of the boxer briefs with his teeth, he was ready to do anything that the women or men in the room instructed him to do. He bit down firmly, gripping the fabric between his teeth, before slowly tugging downwards. The underwear began to part ways with James’ body, but Adam struggled to pull them past James’ large cock, which was obstructing the way. Eventually, Adam managed to tug the underwear past his cock, and he quickly lowered his head to James’ feet. James stepped out of his boxer briefs, and Adam knelt up again. In front of him was a penis that he thought was reserved for male pornstars, one he never expected to encounter in real life. James’ cock was just under 5 inches in length and had a girth of at least 4 inches. The part that shocked Adam was that the penis that was in front of him was limp. Adam was struggling to wrap his head around the fact that James’ penis was 5 inches soft. He couldn’t believe what was in front of him and began to wonder how long it would be when it was hard.

As if reading his mind, Mistress Grace rounded the table and stood next to James. She gently lifted his limp cock before speaking. “Look at how big this cock is. An average guy is this big when he’s hard, and this alpha male is soft at 5 inches, bitch. Slave, when your clitty is fully hard, you are half the man that this alpha is when he is soft!” she said. They all laughed in unison as Adam took in the words that further solidified his place as a beta male.

Mistress Alice spoke up next, “any girl would go wild for a cock like this. I myself would do anything this man asked of me. I’d let him use my body in any way he wanted, even letting him fuck my throat if he desired! You’d probably cum immediately if I touched your pathetic dicklet!” They all laughed again.

“Kiss his cock, bitch!” commanded Mistress Grace excitedly.

A New Realm of Chastity For Slaves

Adam hesitated before moving his head forward and placing his lips on the head of James’ penis. He initially thought that he would be repulsed by this, but he was entranced by the penis in front of him.

“You want to suck it, don’t you, bitch?” James asked from above.

“Yes, sir. Please let me suck your cock, sir!” Adam begged.

Without saying anything, James’ large hands parted Adam’s lips, and he gently pushed his penis into Adam’s mouth. Adam could feel that James was still soft, and he began drooling as his mouth was left with little space as James’ cock slid in and out of his mouth. Adam could sense that James’ cock was growing, and very quickly the cock in his mouth became hard, pushing at the back of Adam’s throat. Adam sucked on James’ cock for a few minutes before Mistress Grace rounded the table and pushed Adam’s head back, away from his friend’s cock. Adam could now see that James’ penis had grown to just under 8 inches, and its girth was around 5 inches now. The cock in front of him was huge. Adam wiped the drool from his mouth.

“Holy shit!” Mistress Alice squealed.

“Lie down on the floor, slave,” commanded Mistress Grace. “We’re going to push your limits. If you pass this element of training, there won’t be anything that gets in your way of servitude!”

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