Chapter 1: Introduction
As I stepped out of the elevator, Ashley greeted me with a devious grin. The corner of her left eye was creased, and her eyes sparkled with excitement. Ashley stood 5'7, slender, with a pair of eyes so mesmerizing that men fell under their spell. Her short black hair, cropped bluntly just above her Chin, bounced as she shook her head.
"Kate, come on in. I have a surprise for you," said Ashley, biting her full bottom lip while beckoning me with her fingers.
As I closed the door behind me, she led me to her living room—an open space offering an incredible view of Downtown. The glass walls seamlessly blended with its modern design, allowing sunlight to warm every room during the day and casting a serene glow as night sets in. I understood why Ashley called this place home. It embodied class, convenience, and comfort.
Without hesitation, Ashley spun me around to face her bookshelf—a beautifully crafted wall of wooden squares with titles displayed in each slot. I squinted, trying to focus on the tidy rows.
Ashley reached over me and pulled a book that had my name on it and the wall swung inward revealing a sex playroom. In the center was the anal orgasm training machine we talk about several weeks ago. I had sighed wishing I could afford that when I told Ashley about my attempts to cum with my ass
. She insisted she could help me get there and would take care of the cost. With the promise of an exquisite adventure ahead, I hoped it would be worth it.
"Well, Kate. What do you think?" she asked, her grin boundless, eyes twinkling with amusement, barely containing her pleasure.
My nervousness battled with the thrill of newfound excitement. It was intimidating; the machine a sleek, pearly-white device, looking like an artifact from a futuristic world. It included a bondage bench,fucking machine and an array of different sizes heads for the machine. sitting on the bondage bench is a steel chastity cage with my name engraved on it
. Ashley must have ordered it custom made.
"I-it's impressive," I managed to croak out, trying to keep up appearances. But internally, my anticipation swelled, and the rest of my apprehension faded away. I couldn't help but imagine all the new sensations that awaited me.
Ashley giggled, walking over to the machine lovingly nicknamed "The Boss." Resting her hand on it, she looked back at me, her excitement infectious. "This is going to change your life, Kate. I promise. I'm so proud of you for coming to me about this. Now." She holds up the Chastity cage "this is your payment, you will spend until I say so locked in chastity, remember?
This way, you have no choice but to learn and focus solely on the pleasure the machine can provide. I've kept it nice and tight, just as you like it."
My cheeks flushed, the heat rising up from my neck and spreading across my face. There was something thrilling about surrendering complete control to someone like Ashley. She was confident and experienced in the ways of the bedroom, which comforted me. I wanted to please her, but I also trusted her artistic, erotic nurturing abilities. "On your back on the bench, kate~ let's lock that cocklete away
and get you ready for your first training session," Ashley demanded, her voice firm yet loving.
Her certainty in her friend's desires was something I'd come to rely on over the years. I adored Ashley; she'd effortlessly become my protector and confidant the day we met, our first year of undergrad. With her, I could find solace and share the darkest secrets without judgment or derision. She was a rare breed of kindness and pleasure.
She patted the synth-leather bound bench.
"Up, up, take your position, kate~" she crooned.
The bench was cool against my skin, and I lowered myself into it. Ashley locked the cage securely around my cock and balls. The sensation a shivering chill that instantly reminded me of my submission to this new experience. It was strange but comforting – as if I was entrusting my pleasure into the hands of my most trusted friend.
She giggled and pushed me down on the belt lovingly, holding the key up to my eyes, before putting it in my hand. "Kneel and give it to me. Ask me to be your keyholder."
Ashley's eyes were playful as she dangled the key to my newfound chastity cage. I knew she wasn't going to let me hold on to it for long, but it was thrilling to feel the power temporarily in my grasp – a silent reminder of the trust she placed in me.
"Please, Ashley," I said softly, swallowing down my nerves. "Make me yours." I opened my hands and lowered my gaze in reverence. I willingly surrendered the key to the cage enclosing my cock and balls.
Ashley's mouth curled into a satisfied smile as she locked the key away in a drawer.
"I'm so glad we're doing this, Kate," Ashley said as she leaned over the bondage bench, brushing my cheek. Her hand found its way to my thigh, giving it a reassuring squeeze. She could tell I was still nervous, but she knew that would quickly fade. "Remember what we discussed? You agreed to daily training. And I won't take it easy on you.
You'll wear this chastity device for as long as I say, and every day, we'll introduce you to new experiences. Because, little kate, submitting to this process means embracing the chance of ultimate self-discovery." Ashley winked as she spoke, making sure I knew she meant every word.
"strip, lay down on your stomach, abs place your hands out to be bound,same with your legs."
Ashley purred with authority.
I followed her instructions, feeling my heart beat faster as I let my inhibitions dissolve. I knew Ashley wouldn't push me beyond my limits, but the buzzing anticipation propelled me forward. The feeling was raw and real, comforting to my soul in a way I'd never experienced. My hands and feet adjusted to the gentle restraints of the bench, as my own vulnerability was laid bare—respecting and owning my femininity.
Ashley continued to lock me in, allowing myself to melt into her promise to guide me.
As the final restraint tightened around my ankles, I became immobile, ready for the journey ahead. The anticipation swelled at the very center of my being, my excited breaths shallow and uneven. I had never felt more alive.
"Kate, my dear friend – look at how far you've come," Ashley said in wonder. "As I buckle you in, I want you to know something. I am committed to tending to your needs, in every single way." Her hand traced along my arm, leaving me longing for more. "You're going to be sooo horny after every single session, but until you can from just your prostate, you won't be cumming "
Ashley giggled and planted a tender kiss on my forehead. Her short black hair, damp with sweat, tickled my skin. As she pulled away, her gaze met mine, filled with so much warmth it sent a shiver of excitement down my spine.
The thrill and allure of being bound and at Ashley's mercy surged through every nerve in my body. I was willingly placing myself in her gifted hands, entrusting her with my most secret desires and expectations. I believed in my dear friend, her experience, and her unrelenting passion for the art of eroticism.
"let's begin sweetie~" Ashley said, and a shiver unexpectedly ran down my spine. I silently cursed the flutter of nerves, but realizing who was taking me into her fierce wings calmed my anxieties. Ashley stood confidently before me, adorned in a silk knee-length robe, open to reveal a tantalizing glimpse of her slender figure. She was, undoubtedly, in her element.
Her fingers grazed the stainless-steel panel adorned with buttons and dials.
"time to activate the scanning mode~ you don't mind if I masturbate while you're teased right" she says with a grin .
Ashley unabashedly shed her robe, her bare chest heaving with breathless enthusiasm. She brushed her hair back and winked at me, biting her lip, giving me a moment to fully appreciate her energetic and erotic spirit.
She guided her fingers to the rows of buttons before her, pressing a particular sequence that would allow the machine to analyze every inch of my insides.
"I'm activating the scanning mode, Kate," Ashley said breathlessly, the desire in her eyes apparent.
The machine pulled a dildo off the rack, one with a squirting tip, and lines it up
with my ass. Ashley smiled in anticipation.
"So you're aware, this device will be controlled remotely by me, and it's designed specifically for anal pleasure. It'll tease and stimulate your prostate while you're locked in the chastity cage. Just remember what you're here for, Kate—exploring pleasure in ways you've never experienced." Ashley's voice was soft as problematic, her words excuse with tantalizing promises.
I swallowed hard, nodding, accepting the commitment I'd made.
The machine squirted lube inside me with a pulse, continuing for a few seconds, thoroughly lubing me
up. The silicone tip of the device then pressed gently against my entrance, applying the perfect amount of pressure as it forced its way in bit by bit. The sensation was nothing short of luxurious, creating waves of engulfing warmth radiating throughout my lower half.
A sigh escaped my lips as the dildo thrust deeper into me, its rhythmic pulses matching the beat of my racing heart. The device entered and retreated, hitting every spot with painful precision. Ashley started laughing.
"I-I can feel every inch of it," I said between gasps, blissfully overwhelmed by the device's skillful movements.
The machine paused, leaving me writhing in the restraints with pleasure, aching for more. It was all the way inside, and I gasped as it began vibrating "begin scan~ oooh you look soooo cute like this"
Ashley teased.
As the dildo palpitated against my inner walls, I took a moment to feel my body's response to the relentless, profound pleasure. I moaned, no longer fighting the intensity of the moment. Electricity sizzled within me.
The mighty 'Boss' whirred to life, scanning every inch of my interior in silence, with immeasurable accuracy. This profound, sensual exploration could only be described as kate's awakening. Then it began fucking me
in earnest. Slowly at first, with gentle determination before picking up the pace. Ashley, with a glint of excitement, observed as I arched my back and succumbed to the device, reveling in the enveloping euphoria that reached the edge of my awareness.
"Ahh! Yes, right there, Ash," I moaned as the dildo heightened its assault on my besieged nerve endings.
It pulled all the wayout , swapping to a much larger, ribbed dildo
that slowly teasingly eased into me,
Soft rumblings escaped from the 'Boss' as it resumed scanning,
plunging deeper with pulse-like rhythm that owned every inch of me.
Around me, the room felt electrified, charged with every fervor and passion coursing
through my trembling, submissive frame.
My body pulsed with pleasure, my heart raced furiously, and a seemingly endless supply
of desire flooded my core.
I squealed, squirming, attempting to pull at the restraints and getting nowhere. Ashley leaned back in her chair, pulling off her skirt and lanties
. She spread her legs wide, teasing me with her bare dripping pussy while she casually felt herself. My cheeks burned with the wanting and my world reeled moreso with the sensations surging through me.
I existed in a euphoric realm, where every thrust of the machine's extension became more dedicated and satisfying. I surrendered all control, reservations, and inhibitions, lost in the electricity of infinite pleasure the Boss inflicted upon me. The friction of the endless anal f*cking create oh so enticing sensations. But I just couldn't cum.
And I yearned for it—for a release that felt close but elusive. It was both maddening and disheartening, despite the ever-growing pleasure inside me. My breath hitched, and I cried out, as the 'Boss' mercilessly pistoned deeper.
Ashley didn't let up; she was determined to drive me to the brink of insanity. Her hand moved furiously between her legs, her fingers working her clit with purpose. I squeaked as the dildo was removed, replaced with a horse dildo, chance I think it was called
. It slicked myself with more lube and pressed agonizingly slow against my entrance.
"Let you just enjoy this euphoria, I know you can feel every silky ridge as it slides into you, reaching deeper than ever, am I right?" Ashley whispered as she deepened her touch, her voice wrought with hunger. I could only nod frantically in response, feeling the thickness spread me wide, stretching me as intimately as ever.
"I am so incredibly proud of you, Kate." I moan as the thing squirts more lube, that was unaware was also mixed with aphrodisiacs, inside me
, further heightening my ardor. "Never underestimate your capacity for experiencing such a magnificent wave of pleasure," Ashley says breathlessly, fingering herself; her nectar trickles down her thighs like an ode to my own yearning.
The mammoth horse-sized silicone device silently eases itself into me, inch by exquisite inch, until I am utterly filled, wonderfully stuffed with every single invigorating millimeter. The intense, unyielding pressure is extraordinary, beckoning me to let go while whisking away my thoughts. The machine kept attacking my prostate
incessantly with achingly precise motions. I lay trapped in a cascade of paradoxical sensations. My nerves thrummed with longing while craving an escape, and my core throbbed with insistent heat, building steadily as it flowed through me. My breath hitched, and I cried out. I desired with every atom in my body to just cum, to release myself of these rising pressures, temporarily quenching my overwhelming thirst.
Ashley teased, “Ahh, right there, Kate?
You’re so close, but you can’t quite get there on your own, can you?” She grinned, watching my helpless flail within the restraints, her skilled hands darting between her own legs, provoking herself with eager fervor. I could feel myself slipping further and further, my resolve slowly crumbling with euphoric pressure. The machine had begun rotating ever so subtly, reverberating along that elusive sweet spot which begged for a climax.
Ashley began to finger herself intensely
; the soft echoes of her moans heightening my own frenzy as my body writhed under the maddening grip of forbidden release.
My muscles tensed, coiled, trembling on the precipice of surrender to the endless cascade of profound sensation. The 'Boss' continued thrusting, mercilessly probing deeper, my horizontal rope bridge.
Time slowed to a syrupy crawl; moments stretched to minutes, with every hungry gasp echoing through the air as we danced together on the cusp of insanity
Ashley came with a loud set of moans while I whimper as the machine stopped deep inside me, still vibrating
. My muscles, clenched with need, begged for a release that seemed unattainable. Denied the pleasure, my yearnings bubbled like a spring of molten lava beneath my skin.
"Turn it off," I whispered, my begging voice belying the depths of my internal strife.
Her dark eyes glinted mischievously. "No."
Her response caught me off guard, but then, my beautiful and wicked friend continued, "I'm not going to turn it off until you beg for it, Kate. You're sooooo desprate to cum. But you can't can you? Your ass pussy isn't trained well enough. Just one little touch of your cocklet would let you cum
," Ashley taunted.
Her words pierced deeper than a million needles. The torment and the agony of being teased combined caused my body to writhe, and my breaths came out in short, sharp pants. I wanted to beg, plead, and do anything just to release the tension and frustration building deep within me.
"For god's sake, Ashley, please!" I cried, arching my back and straining against the leather cuffs. "Please, I can't take it anymore.
Make it stop," I begged with desperation in my voice. I was helpless, shaking, and completely at Ashley's mercy. But she remained resolute, watching with a wickedly amused grin as I twisted and turned in my restraints.
"Look at you, so desperate to cum, sweating, and shaking, your hole gripping the dildo so tightly. And yet, the simple touch of your manhood is all it would take to push you over the edge. You're learning your lesson, Kate. That good little femboys cum just from their ass... And since you can't yet ... You don't get to cum.
Ashley's words hung heavy in the air, and I could barely process the immense frustration coursing through me. I could feel a deep, unfulfilled yearning that centered around my denied sex, and the mixed sensations of pleasure and denial rendered me utterly helpless.
Her gaze never wavered, and she stood tall, her perfectly toned legs spread apart in confident power. Ashley didn't break eye contact as she removed her fingers from her own dripping pussy, slowly bringing them towards her mouth.
Then paused, and put them in mine
so I can taste how she enjoyed herself during my training. I moaned as she slipped those fingers in, my tongue swirling around her digits. I could taste the essence of her arousal, bitter yet tantalizing as the taste defied all reason and filled me with an unexpectedly intense craving for more.
The machine slowly removed the dildo, moving it to the cleaning bay , before selecting a smaller plug adorned with a gemstone and returning to the edge of my entrance. Ashley pressed the remote and the plug started its descent, slowly filling every nook of my passage as I squirmed and moaned under the overwhelming sensation. I could barely believe it, as the silky texture of the gemstone pressuring my prostate had me on the verge of capitulating to the powerful waves of ecstasy.Ashley smiled wickedly as she pressed a button, setting the plug's vibrations to pulse rhythmically at a gradually increasing rate. It also began to expand and a locking noise was heard
as she pressed another button confirming it was locked into place trapping it. There was no turning back now, I was truly in her care from this point forward.
Captivated,burying my head into the restraints, I felt the plug inside of me, surging and pulsating with energy;a vehicle for Ashley's unyielding control as my prostate was massaged mercilessly. Breathlessly,my body quivered and shuddered uncontrollably, repeating the words "please" and "no more" like a mantra. Ashley slowly began to untie me as the machine returned to standby, leaving the plug inside
me, and the cage secured around my frail, long-denied cocklette.
"Remember how you begged me to stop earlier?" Ashley said quietly as she cradled my exhausted form, untying the last of my restraints. "That was just the beginning, kate. Together, we will explore your limits, pushing you beyond what you ever thought possible. You did suuuuch a good job today." I squeaked as the plug started vibrating
again, Ashley's finger tracing the length of my sensitive inner thigh. The fluttering, delectable sensation of her feather-light touch tickled my nerves, sending ripples of anticipation coursing through my veins.
My cheeks flushed at her words, and I blushingly thanked her as she helped me from the bench, embracing me gently. Ashley effortlessly supported me, guiding me towards the plush couch in the center of the room.
Her loving embrace served as a soft landing, cushioning my weary limbs against the exquisite pressure of the mind-altering session that had just transpired.
"sooo, how was it?"
Ashley asked with a devious grin, her mischievous eyes a mirror of her own satisfaction. Her fingers gently caressed the plug that had left me vulnerable just moments before. Her touch ignited an intricate dance between aching pleasure and humbling denial, the persistent being pushed deeper.
"the plug will stay in till your session tomorrow~
it will be activated when you least expect it, to remind you of your training," she teased.
"that... That was" I stuttered "amazing. It felt so good but... I just couldn't cum."
A wave of exhaustion washed over me, and Ashley reclined back into the plush couch, pulling me into her arms.
"That was just the start, kate. The road to self-discovery is long, arduous, and unpredictable, but I'll be here, right beside you the entire way, every single step along the path." Ashley's hand swept a loose strand of hair from my face, tucking it gently behind my ear. Her loving smile was one of understanding, comfort, and absolute adoration.
"I can't wait till you have your first anal orgasm. You're going to be sooooo cute."
Ashley giggled with unbridled excitement, her eyes sparkling with an insatiable lust for life. "Imagine, Kate, what it's going to feel like when you finally experience the Big-O from nothing but anal pleasure. Oh, honey, your world will be rocked. For now, I'll let you stay here for tonight, since your definitely exhausted."
"
thank you" I muttered graciously, unable to hide the increasing weariness in my voice. Ashley graciously gestured to the luxurious queen-sized bed draped in emerald green silk, ensconced within her spacious bedroom. The room exuded an understated elegance, seamlessly coming alive with warm ambient lighting and a collection of tastefully arranged perfume bottles, sitting proudly on her velvet-draped vanity table.
As we layed down togerher I gasped as the butt plug began to vibrate
unexpectedly, causing me to shudder and squirm. Ashley giggled beside me, her fingers absently tracing the line of my shoulder and helping me ease into submission. She assured me that the device would please me throughout the day and night to comes.
In the quiet intimacy, our bodies intertwined, I felt safe, cradled in Ashley's gentle care. I reveled in the security, knowing she would aid me in exploring a new world of pleasure, one that I had been too timid to venture into; but now, there was no turning back.