Punishment Due II (2023 Revision)

But today, I had a surprise for him. After he had emptied himself, I ordered him to bend over the sink once again. He eagerly complied, his anticipation palpable. As I pressed something into his tight hole, he moaned with pleasure. I could feel his body shudder as I inserted the small butt plug, and I knew he was mine.

“Keep that in there until I remove it,” I commanded. “It will help loosen you up a bit back there.”

He stood up, feeling the strange sensation of the plug inside him. It was narrow at the base, and his clenching anus held it snugly in place. I could see the look of submission in his eyes, and it made me feel powerful.

“Do you have any questions about this?” I asked.

“No, Mommy,” he replied, his voice barely above a whisper.

I smiled and reached out to stroke his head. “Good boy,” I said. “It’s nice to see you learning so quickly.”

I led him back to my room and opened a drawer, taking out a pair of pink cotton panties. I handed them to him, knowing they would fit snugly and help keep the plug in place.

“Slip these on, my love,” I purred, handing him a pair of lacy panties. “They’ll fit you like a glove and keep that plug in place.”

He hesitated for a moment, his cheeks flushing with embarrassment. But as he slid the panties up his legs, I couldn’t help but admire the way they hugged his curves, accentuating his every inch.

“Mmm, you look so pretty,” I cooed, running my fingers over his smooth skin. “My little sissy boy.”

As he sat down to breakfast, I watched him squirm in his seat, the plug nestled deep inside him. But as the day wore on, he grew more and more comfortable with the sensation, his body relaxing around the toy.

And when I led him to the kitchen to clean the floors, I couldn’t resist watching him from the doorway, his tight pink panties stretched across his pert little ass. It was all so deliciously naughty, so thrillingly taboo.

Later that night, as I removed the plug from his body, I couldn’t help but smile at the way he squirmed and moaned beneath me. He was mine, body and soul, and I was going to take him to places he’d never dreamed of before.

-oOo-

-Day 11-

I awoke to the gentle sound of a knock on my door, my heart skipping a beat in anticipation. It was still early, the sun barely peeking through the curtains, and I hadn’t even had the chance to rouse him from his slumber. With a mixture of surprise and excitement, I beckoned him to enter, my body tingling with anticipation.

As he stepped into the room, a nervous energy radiated from him, his eyes darting around the space. My gaze couldn’t help but be drawn to the undeniable evidence of his desire, his half-hard cock straining against the fabric of his sleepwear. A blush crept across his cheeks, a telltale sign of his innocence and vulnerability.

“I-I woke up with an erection, Mommy,” he stammered, his voice laced with uncertainty. “It’s starting to fade now, but I thought it best to inform you, just as you had mentioned.”

A smile danced upon my lips, a mixture of pride and admiration for my son’s willingness to heed my guidance so promptly. The connection between us deepened, a bond forged in trust and understanding.

“That’s very commendable, my dear son,” I purred, my voice laced with affection. “I’m truly proud of you. Come closer, stand beside the bed.”

He complied, his movements hesitant yet filled with a longing to please. As he stood beside me, his presence enveloped me, his vulnerability captivating my senses. I reached out, my fingers grazing his arm gently, a silent reassurance that he was safe in my embrace.

“Now, my love, tell me, what might have caused this awakening within you?” I inquired softly, my eyes locked with his, searching for the truth hidden within his depths.

“I-I don’t know, Mommy,” he confessed, his voice a mere whisper. “Sometimes, it just happens when I wake up.”

A tender smile graced my lips, understanding washing over me like a warm embrace. Boys, in their blossoming youth, often found themselves stirred by their own desires, their bodies awakening to the mysteries of pleasure. I reassured him, my voice a soothing melody.

“That’s alright, darling. It’s quite common for boys to wake up with such delightful hardness. But I couldn’t help but wonder if there was something more to it. Now, when you find yourself in such a state, what do you usually do?”

“I-I pleasure myself.”

“Well, then, my love, don’t keep me waiting.”

“You mean... right now?”

“Indeed, my sweet. Indulge in the pleasure of your little member, just for me, this very moment.” His cheeks flushed with embarrassment as he met my gaze, but with a determined resolve, he swiftly reached down and began to caress himself. Though his manhood appeared flaccid, he gave it his all, his hand gliding up and down, while I watched him with an impatient longing.

“Will you soon grow firm again? I wouldn’t want to spend the entire morning here, my dear.”

I gazed intently, my eyes fixated on his struggling member, aching to witness its transformation. A subtle smirk played upon my lips as I observed the tears of vulnerability welling in his eyes. Unable to resist any longer, I extended my hand, delicately replacing his futile efforts with my own. My fingers danced along his length, skillfully caressing and teasing, eliciting gasps of pleasure from his quivering lips. The realization washed over him like a tidal wave, his body responding eagerly to the touch of his own Mother, his desire surging forth.

With each stroke, his manhood rose to its full glory, a testament to the forbidden passion that consumed us both. I reclined, basking in the intensity of the moment, my eyes never leaving his throbbing member.

“Now, my dear, bring yourself to completion,” I whispered, my voice laced with a mixture of authority and desire.

Still dazed by the surreal encounter, he grasped his pulsating flesh, his movements growing frantic and desperate. Sensing his need, I retrieved a tissue from the box beside my bed, placing it gently upon the mattress without uttering a single word. He understood my unspoken command, directing his pulsating manhood towards the awaiting tissue. With each fervent thrust, his release became inevitable, his essence spilling forth in a torrent of ecstasy. The intensity of his pleasure caused the first eruption to soar beyond its intended target, staining the pristine sheet beneath us. The subsequent streams found solace upon the tissue, saturating it with his essence.

Once he had finished, I delicately retrieved the tissue, a silent gesture of control and possession. My gaze shifted towards the mark upon my sheet, a silent demand for his obedience and submission.

“Delicious,” I purred, watching him hesitantly lick up his own essence from the sheet. His reluctance only fueled my desire, and I couldn’t resist taking hold of his hair and twisting his head around to face me.

“You’re mine to command,” I whispered, my breath hot against his ear. “And when I tell you to do something, you do it without hesitation.”

He nodded, his eyes wide with a mix of fear and desire. I could feel his body trembling beneath me, and I knew he was mine to mold and shape as I pleased.

“Good boy,” I cooed, releasing his hair and sitting up in bed. My nightie had ridden up, revealing my long, smooth legs and a tantalizing glimpse of my sex. I watched as his eyes lingered on my body, hunger and lust written all over his face.

“Bring me one of my slippers,” I commanded, pointing across the room. “And then come back to me, my sweet little pet.”

He swiftly grasped the delicate slipper, traversing the room with a sense of urgency, his eyes widened with a desperate plea. I gracefully positioned myself in the heart of the bed, my supple form supported by a plush pillow nestled against the ornate headboard.

“Come, my dear boy. It appears that another lesson in obedience is in order.”

A soft whimper escaped his lips as he obediently ascended onto the bed, draping himself across my lap as I had instructed. I gazed down at him, observing the fading welts on his cheeks, reassured that he was prepared to endure a thorough spanking. Succumbing to a sudden surge of sadistic desire, I decided to prolong my son’s anticipation.

“You have been quite naughty, haven’t you?”

With a gentle tap of the slipper against his backside, I relished in the way his body instinctively flinched.

“Y-yes, Mother.”

“Yes, Mother. And now, you shall receive a well-deserved spanking, won’t you?”

His entire being tensed, awaiting the commencement of his punishment.

“Y-yes, M-Mother.”

I scrutinized him, captivated by the tautness of his muscles, the glistening beads of perspiration forming upon his flawless skin.

“Yes, Mother. It will undoubtedly inflict pain upon you, won’t it?”

“Y-yes, Mother.”

Unable to restrain myself any longer, I surrendered to my primal desires.

“Let us begin, my dear!”

I gently caressed his backside with the slipper, feeling a surge of power as I prepared to unleash my desires upon him. The anticipation in the room was palpable, a mixture of both tension and longing. As the slipper made contact with his flesh, a cry escaped his lips, a symphony of pleasure and pain intertwining in the air.

With my left hand firmly pressed against the small of his back, I skillfully wielded the slipper, striking him with a fervor that matched the intensity of my own desires. His body contorted and trembled against my thighs, his tears mingling with the scent of our shared passion. The room became saturated with the intoxicating aroma of our mingled sweat and the sweet essence of my arousal.

My gaze fixated hungrily upon his blushing cheeks, watching as they transformed from a delicate pink to a fiery crimson. Only when his entire backside was adorned with the mark of my affection did I cease my ministrations, casting the slipper aside. He lay limp across my lap, and I gently lifted him, guiding him to stand beside the bed.

Positioning myself before him, my legs spread wide, I proudly displayed my glistening, wet entrance. His eyes were drawn to it, captivated by the raw desire that emanated from within me. I reveled in the knowledge that he could witness the profound effect his submission had on me, how it ignited a fire deep within my core.

“Do you understand the importance of obedience now?” I purred, my voice laced with authority.

“Y-yes, Mommy,” he stammered, his voice filled with a mixture of reverence and longing.

“Good,” I replied, a wicked smile playing upon my lips. “You had best remember that, unless you crave more of my intoxicating discipline. Now, hurry along to the bathroom, cleanse yourself, and return to me promptly.”

He scurried from the room, his eagerness evident in his hurried steps. As he disappeared, I surrendered myself to the plushness of the bed, my hands instinctively finding solace between my thighs. Fingers danced upon my aching flesh, igniting a symphony of pleasure that mirrored the intensity of the encounter.

The remainder of the morning unfolded just as before, with an air of tantalizing intimacy. I tenderly administered his enema, relishing the way his body responded to my touch. As I delicately inserted the butt plug into his quivering derrière, a shiver of desire coursed through me. To further ignite his senses, I bestowed upon him a fresh pair of panties, this time a pristine white adorned with lace that caressed his legs and waist.

After indulging in a delectable breakfast, I granted him the privilege of expressing his devotion through the art of writing lines. This time, however, I demanded a more provocative confession: “I am a sissy little cry-baby.” The blush that adorned his cheeks betrayed his embarrassment, and I reveled in the power I held over him. When he timidly presented me with his completed lines, his face aflame with humiliation, I perfunctorily inspected his work before turning my gaze upon him.

“And what, my dear, are you?” I inquired, my voice laced with a seductive undertone.

“I am a sissy little cry-baby, Mommy,” he responded, his voice trembling with a mixture of shame and desire.

“Pardon me? I’m afraid I couldn’t quite hear you,” I teased, savoring the anticipation.

“I am a sissy little cry-baby,” he proclaimed, his voice growing bolder.

“Louder,” I commanded, my eyes gleaming with wicked delight.

“I am a sissy little cry-baby!” he exclaimed, his voice resonating with newfound confidence.

“Indeed, you most certainly are,” I purred, relishing in the power dynamics that bound us. “Come, my sweet sissy, let us indulge in a sumptuous lunch together.”

After indulging in a delectable lunch, I led him into the opulent living room, beckoning him to join me on the plush couch. His eyes darted around nervously, anticipation mingling with apprehension. He had anticipated a mundane afternoon of chores, but fate had other plans in store for him. Sensing his unease, I tenderly draped my arm around his broad, masculine shoulder.

“Now, my love, it is time for you to embark on a journey of sensual enlightenment. Your delicate manhood, though petite in stature, possesses the potential to bring immense pleasure to a woman. However, it is imperative that you acquire a repertoire of skills beyond mere physical endowment. I yearn for your touch to ignite the flames of passion within me, but I desire a more nuanced approach than mere physicality. Thus, I shall guide you in the art of pleasuring a woman with your hands and mouth,” I whispered, my voice laced with a seductive allure.

With a mischievous glimmer in my eyes, I revealed our first step towards this intimate education - a tantalizing DVD that would serve as our visual guide. Together, we would explore its secrets, allowing it to unveil the intricacies of desire. And once the lessons had been absorbed, he would have the opportunity to put theory into practice, his hands and lips becoming instruments of pleasure, sculpting ecstasy with every caress.

I pressed play on the DVD player, and my lover’s eyes widened as the screen illuminated with two gorgeous women entwined on a bed. Their bodies glistened with sweat as they explored each other’s curves with their fingers and tongues. I couldn’t help but notice the bulge in his panties, a clear indication of his arousal. He was transfixed by the erotic display before him, and I relished in the power I held over him.

As the scene came to a close, I turned to him, waiting for his response. His eyes were still glazed over with desire, and I knew he was mine to command. I gave him a chance to speak, but he remained silent, lost in the lustful haze of the moment.

I leaned in close to him, my lips brushing against his ear. “Do you think you could do that?” I whispered, my voice dripping with seduction.

He stammered for a moment before finally responding. “I-I think so, Mommy. I’ll try.”

My heart raced with excitement as I realized the depths of his submission to me. I knew that I had him completely under my spell, and I couldn’t wait to explore every inch of his body in the same way those two women had explored each other.

I rose to my feet, feeling the heat of his gaze on my skin. Slowly, I shed my clothes, revealing every inch of my curves to him. His breath caught in his throat as he took in the sight before him, his cock straining against the fabric of his panties.

“Please, Mommy,” he whimpered, his voice thick with desire. “I can’t take it anymore.”

I smirked, enjoying the power I held over him. “And what caused that, my little pet?”

“It was the movie, and seeing you undress,” he confessed, his cheeks flushing with embarrassment.

I arched an eyebrow, feigning surprise. “But you didn’t say anything during the movie, or after. Why is that?”

“I...I forgot,” he stammered, his eyes downcast. “I was just so surprised by what I saw.”

I sauntered over to him, my hips swaying seductively. “Well, let’s see if you can make it up to me,” I purred. “If you please me, maybe I’ll let you off the hook.”

Relief flooded his features, and he dropped to his knees beside me. I reclined on the couch, watching as he tentatively reached out to touch me. His fingers were hesitant at first, but soon he was exploring every inch of my body with a hunger that made my pulse race.

“Good boy,” I murmured, my fingers tangling in his hair. “Now, let’s see what that tongue of yours can do.”

I reclined, surrendering to the intoxicating sensations that awaited me. With closed eyes, I felt his hesitant touch, a delicate caress upon my most intimate place. His fingers explored me with a tender curiosity, seeking out the hidden depths of pleasure. And then, with a skilled precision, he discovered my most sensitive spot, my pearl of desire. A shiver of anticipation coursed through me as he began to rub it, igniting a fire within.

Moans escaped my lips, mingling with the sweet symphony of our desires. I writhed and squirmed, unable to contain the mounting pleasure that surged through my body. My son’s fingers, once uncertain, now danced with confidence, skillfully manipulating my throbbing nub. Each stroke, each flick, sent waves of ecstasy crashing over me, building towards an inevitable climax.

As the waves of pleasure subsided, leaving me breathless and satiated, I slowly sat up, spreading my legs before him. The air crackled with anticipation, a silent invitation for him to continue his exploration. His gaze met mine, a mix of desire and uncertainty.

“Not bad at all,” I purred, my voice laced with satisfaction. “Now, my dear, it’s time to use that talented tongue of yours.”

He leaned forward, his desire evident, but hesitated. A flicker of concern crossed his face, his eagerness tempered by a newfound awareness.

“Mommy, I-I’ve become aroused again,” he confessed, his voice laced with a mix of embarrassment and longing.

A knowing smile graced my lips, understanding his internal struggle. It was clear he yearned to please me without faltering, to avoid repeating his previous misstep. In that moment, I decided to reward his determination, setting aside the temptation to indulge in the pleasure of discipline.

“I know, my love. Don’t fret about it,” I reassured him, my voice a soothing balm. “When we engage in these intimate acts together, you need not speak of your arousal. It’s only natural for you to feel excited. You won’t be punished for it.”

Relief washed over him, gratitude shining in his eyes as he absorbed my words.

“Thank you, Mommy,” he whispered, his voice filled with gratitude and renewed enthusiasm.

“Get down on your knees, my love,” I whispered, my voice dripping with desire. “I want to feel your tongue on me, just like your hands.”

Without hesitation, he obeyed, his lips and tongue exploring every inch of my wetness. I moaned and writhed beneath him, my body trembling with pleasure. He was a master at this, and I couldn’t get enough.

As he continued to pleasure me, I couldn’t help but think about how taboo this was. My own son, pleasuring me in ways that no one else ever had. It was so wrong, yet so incredibly arousing.

Later that night, I took him to the bedroom and gave him a punishment that he would never forget. I teased and taunted him, working my fingers deep into his tight little hole until he was writhing and moaning beneath me. It was so erotic, watching him squirm and beg for more.

By the time I was finished, he was left panting and gasping for air, his body trembling with pleasure. And I knew that he was ready for more.

-oOo-

The End!