Want to support CHYOA?
Disable your Ad Blocker! Thanks :)

Chapter 2 by JenNS JenNS

Who are you?

A former Wonderland Employee (JenNS) (Trans, Lesbian, Humiliation, Mind Break)

Kinks Included In The Story

Trans
Lesbian
Ball Busting
Humiliation
Wrestling
Mindbreak

Profile

Age: 20
Height: 5'10
Weight: 160 lbs
Body Type: Bountiful
Genitals: Both
Sexual Disposition: Switch
Medication:
Modification:
Equipment:
Patented Equipment: Smart Safety Collar 0.5
Bio: Jess grew up like most people after the corpo wars (which caused a full collapse of society) she was raised in a state owned orphanage, when she reached adulthood she worked for Wonderland as a bunnygirl, not wanting to either have only a pussy or dick she chose the most _enjoyable _option, both. Eventually she began to hear whispers from the wealthy women who'd hire her, leading her to investigate the estate. Eventually the estate caught wind, inviting her to join, which she of course did.

Life Path: I am Curious

Training: Begineer Rogue Classes, and Novice Harlot Tutorial

MORPHD
My Maid ranking is 0 and my chosen rank within the Maid Guild is to be None
My Object ranking is 0 and my chosen rank within the Object Guild is to be None
My Rogue ranking is 5 and my chosen rank within the Rogue Guild is to be None
My Pet ranking is 0 and my chosen rank within the Pet Guild is to be None
My Harlot ranking is 5 and my chosen rank within the Harlot Guild is to be None
My Doll ranking is 0 and my chosen rank within the Doll Guild is to be None

My Average ranking is None.
My Enforcer rank is 0 and my chosen rank within the Enforcer Guild is to be None.

I have 50 PP's in the bank.
I have 10,000 EE's in the bank.

Consent Contract
Generic Sexual Contact: Y
Any Bondage: Y
****: Y
Consensual **** Order: Y
Optional
Type which your character is fine with, the things in brackets are the ones to mention.
Sexual Boundaries: Oral Access, Anal Access, Genital Access, Urethral Access, Chastity, and Contraceptive
Physical Boundaries: Breath Play, Pain, Semen, Pee, Scat, and Blood
Modification Boundaries: Tattoo, Piercings, Hormones, Limb Confiscation, Surface Level Body Modification, and Internal Remodelling
Social/Mental Boundaries: Public, Humiliation, Simulated ****, Gender Body Type: Muscular, Slender, Bountiful, Androgynous, Genitals: Penis, Vagina, Both, None, Gender Identity: Woman, Non-Binary, It, Mental Suppression, and Hypnosis
Contract Stipulations: Revoke the right to deny any specific methods, revoke the usage of safe words within the Estate, revoke the right to refuse an offer for employment, training, or punishment from a master

Accommodation
Services:
Housing:
Clubs:

Please log in to view the image


Prologue

My heart hammered against my ribcage like a trapped animal as I stood there in the dim glow of the streetlamp, staring at the imposing door of The Estate. At 6'10", I towered over most folks, my massive muscles coiled tight under my skin, but right now, I felt small and was honestly scared shitless. This place had secrets I'd poked at too hard during my off-hours snooping, away from the roaring crowds of Wonderland's octagon where I crushed opponents and claimed their wives with my swelling cock. One wrong move, and this could be it. My end. Sweat beaded on my forehead, trickling down between my heaving breasts, and I could feel my 9-inch flaccid dick twitching nervously against my thigh, hidden in my pants, while my hidden pussy clenched with dread behind my heavy balls. I hesitated, fist raised, breath coming in short bursts. Fuck it. I knocked. Three sharp raps that echoed louder than they should have in the quiet night. The door creaked open, revealing an old man with sharp eyes and a crisp suit. Majordomo, I guessed from my research. He looked me up and down without flinching at my amazonian frame, then stepped aside. "Miss Smith," he said smoothly, his voice like aged whiskey. "Please, come in. We have much to discuss."

I ducked under the lintel. Doors were always a hassle for someone my size. And followed him through a hallway lined with flickering sconces that cast long shadows. My wide hips brushed the walls, and I fought the urge to bolt. He led me to an office, all dark wood and leather, the air thick with the scent of polished oak and something faintly herbal. "Have a seat," he gestured to a couch that looked plush as hell. I sank into it, and damn, it molded to my body like it was custom-made for a giant like me. The most comfortable thing I'd ever parked my ass on, cradling my muscles and letting my balls settle heavy between my thighs. Majordomo poured a cup of tea from a silver pot and set it in front of me on a low table. "Decaf," he noted with a small smile. "No need to add jitters to your evening." I wrapped my thick fingers around the cup, the warmth seeping into my palms, but I didn't sip yet. My mind raced. Publicly, I was the unbreakable futa powerhouse, smirking as I ground my veiny length into some married guy's wife until she squirted and begged, leaving him cucked and broken. But here? Alone with this guy? My switch side itched, that hidden craving to drop the mask and let someone else take control bubbling up, making my pussy throb faintly.

He settled into a chair across from me, folding his hands. "I know about your investigation, John. Wonderland's top star poking into our affairs. Impressive, really. Most don't get that far." My stomach twisted. "You gonna make this disappear? Me, I mean?" He chuckled softly, waving a hand. "Not at all. The Estate doesn't kill curious souls like you. A cease and desist, perhaps, to keep things quiet. But we admire initiative. In fact, I'd like to offer you a place here. A role that suits your... talents." A place? My mind reeled. The Estate was whispered about in the neon underbelly of Wonderland. Power, pleasure, no holds barred. My hypersexual drive flared at the thought, cock stirring slightly as I imagined what 'talents' he meant. Dominating in the octagon was one thing, but here? Maybe a chance to flip the script, to finally scratch that submissive itch without the stigma crushing me. I nodded, voice steady despite the nerves. "Yeah. I accept." Majordomo's eyes gleamed as he reached into a drawer and slid a thick sheaf of papers across the table. A consent contract, the cover read in elegant script. "Excellent. Now, to formalize things. Read it over, but I assure you, it's comprehensive. Every detail laid out clearly."

I flipped through the pages, my eyes scanning the dense text. The clauses were precise, outlining permissions and scenarios in stark terms that left nothing to interpretation. Specific acts, boundaries, and exchanges spelled out without ambiguity. My pulse quickened as I went through the checkboxes, mentally aligning them with my own drives and limits. I ticked off almost every single one, my body responding with a subtle heat that made my dick twitch faintly in my pants, balls shifting with building tension. But two stayed unchecked, ones that didn't fit my current edges or public life. The rest, though? They unlocked something deep, promising the balance I'd craved amid the expectations of my world. I set the pen down, signing with a flourish. "Done. What's next?" Majordomo leaned back in his chair, his expression shifting to one of measured satisfaction as he watched me sign the contract. He took the papers back, filing them away with a nod. "Very good, John. Welcome to the fold. As a member of the gentry class here at The Estate, you'll have certain privileges and responsibilities. One of the first is selecting basic training from our guilds. This preparatory phase will last six months, conducted off-site before you fully integrate into the estate proper. It ensures you're versed in the dynamics that make our world tick." I shifted on the couch, my massive frame making the cushions dip deeper, my cock still half-stirred from the contract's implications, pressing warmly against my thigh. Gentry class? The words hung in the air, exotic and loaded, stirring that mix of dominance and hidden yearning in my gut. "Guilds? Like what?"

He steepled his fingers, his voice steady and informative, no hint of anything personal in his tone. Just business. "We have several paths for foundational training, each honing specific skills and mindsets. The Maid guild requires no introduction, it's the backbone of service and precision. Then there's Object, where one becomes living furniture or decorations, static yet integral to the ambiance, enduring in silence. Rogues are our escapist brats, masters of mischief and evasion, always one step ahead in games of chase and tease. Pets delve into petplay, embracing instinctual roles on all fours, collared and responsive. Harlot focuses on sex work, the art of transaction and seduction in its rawest forms. And Dolls, for dollplay, immobile perfection, posed and played with like exquisite toys." My mind raced through the options, each one painting vivid pictures that tugged at different parts of me. The Rogues sounded like a thrill, that bratty edge mirroring the cocky taunts I threw in the octagon, but with room to flip and get chased down, pinned, made to yield. Harlots? Straight fire. Channelling my hypersexual core into something professional, claiming and being claimed in equal measure, my swelling length buried deep or my pussy stretched wide in deals that left everyone spent. The others tempted too. The idea of holding still as an Object, muscles locked while hands roamed my body, or dropping to all fours as a Pet, tail wagging while a firm hand guided me. But those two guilds hit the sweet spot, balancing my public powerhouse vibe with the submissive itch I kept buried.

"Rogues and Harlots," I said firmly, my voice carrying that octagon gravel, even as my balls tightened with anticipation. "Those are my picks." Majordomo's eyes flickered with approval, no more, no less. "An intriguing choice. We'll arrange the details promptly. Expect your first session to begin within the week. In the meantime, maintain discretion. Your life in Wonderland continues as is." I rose from the couch, towering over him now, my body humming with a new energy that made my hidden folds pulse faintly. Six months. Training. Then the estate. Fuck, this was gonna change everything. The decision hit me like a body slam in the octagon. Quitting my wrestling gig was non-negotiable if I wanted to dive headfirst into this. Wonderland's crowds would miss my towering frame crushing opponents and leaving husbands limp while their wives begged for more, but fuck it. I handed in my notice the day after signing that contract, my manager's jaw dropping as I loomed over his desk, my 18-inch cock straining against my shorts from the sheer thrill of freedom. No more spotlights forcing me to top every damn time, this was my shot to scratch that itch without the world watching. By week's end, I'd packed my bags. Mostly workout gear and lube. And hauled my massive, muscled ass to the practice estate on the outskirts, a sprawling mock-up of The Estate's opulence, all manicured lawns and shadowed alcoves designed for 'lessons' that made my hidden pussy clench in anticipation.

Settling in felt surreal. The place buzzed with trainees from all guilds, but I stuck to my wing, a suite with reinforced furniture that could handle my 6'10" bulk and the sway of my heavy breasts and balls. Majordomo's team had prepped everything, my schedule arrived via encrypted app, splitting the six months between Rogues and Harlots, alternating weeks with joint sessions to weave the skills together. Instructors were pros. Sharp-eyed dominants and sly switches who saw right through my powerhouse facade, poking at that submissive core I kept locked down. Rogues training kicked off hard and fast, like a tag-team ambush. First week, it was all about the brat basics, evasion drills in the estate's labyrinthine gardens, dodging handlers who chased me with crops and cuffs. I'd bolt on those long legs, my cock flopping heavy between my thighs, heart pounding as they'd corner me against ivy walls, pinning my wrists and spanking my ass red until I squirmed and taunted back, 'That all you got?' But they pushed deeper. Teaching me to tease without mercy, slipping out of bonds mid-scene, only to 'accidentally' let them catch me, my body arching as rough hands yanked my pants down and fingers plunged into my slick folds. We roleplayed chases that ended in me bent over benches, their cocks slamming into my pussy while I wriggled like the escapist I was becoming, moaning defiance even as cum dripped down my legs. By month two, I was a pro at the flip: starting as the pursuer, grabbing a fellow trainee's hips and fucking their mouth deep, then 'losing' on purpose, dropping to my knees to suck greedily, balls slapping my chin as they face-fucked me into submission. It fed that hidden hunger, letting me brat out my dominance before yielding, my massive frame trembling under their control.

Harlots was a whole other rush, pure transactional heat from day one. The instructors threw me into seduction sims. Private booths where I'd negotiate 'deals' with clients played by staff. 'How much for your throat around my dick?' one growled, and I'd counter with a smirk, hiking my skirt to flash my swelling length and dripping slit. 'Double if you make me cum first.' Then it'd escalate, me on my back, legs spread wide as they pounded my ass, or riding their faces, grinding my pussy until they lapped up every drop. We covered the spectrum. Blowjobs in alleys behind the estate, where I'd kneel in the dirt, lips stretched around thick shafts, swallowing loads while haggling tips, gang scenarios in the lounge, taking three cocks at once, one in my mouth, one stretching my cunt, another reaming my hole until I was a slick, quivering mess covered in jizz. They drilled pricing for kinks too. Extra for **** me out while I deepthroated, or tying me spread-eagle for hours of edging, my 18-inch beast throbbing untouched as vibrators buzzed against my clit. Month three blurred the lines, I'd brat into a Harlot scene, teasing a 'client' by evading his grabs, only to get tackled and railed relentlessly, my cries echoing as he filled my womb with hot seed. It was raw, professional filth. Learning to detach just enough to perform, but my switch side loved when sessions flipped, me topping with brutal thrusts into their asses, claiming payment in their submission.

The joint weeks were the wildfire, blending Rogue mischief with Harlot hustle. We'd run 'heists'. Stealing props from secured rooms, but if caught, it turned into paid play, me bartering my body for escape, sucking off guards in exchange for keys, or leading a bratty crew in a tease orgy, dodging whips while fucking our way to victory. My body adapted, muscles honed from endless chases and positions, my cock and pussy constantly aching from use. Nights ended with me collapsed in bed, fingering myself to the day's highs, imagining the full estate's depths. Conflicts arose too, that dominant wrestler in me rebelled at first, shoving instructors away mid-yield, but they broke it down, sessions turning therapeutic. Me on all fours, collared loosely, as a domme whispered commands, her strap-on burying deep until I begged, tears mixing with sweat, finally voicing that craving to be owned. By month six, I was transformed, a seamless Rogue-Harlot hybrid, sly enough to vanish into shadows for a quick fuck-for-fee, bold enough to chase and conquer before surrendering my holes. Quitting the ring had been right, no more faking the top-only life. As graduation loomed. Final assessment with mock clients and pursuits that left me bruised, blissed-out, and leaking cum from every orifice. I felt ready. The estate awaited, my gentry spot earned through sweat, seed, and surrender. Fuck, I couldn't wait to unleash it all.

The train whistle pierced the crisp morning air like a sharp intake of breath before a plunge, and there I was, John Doe, fresh from six months of sweat-soaked surrender at the practice estate, standing on the platform in my uniform drab: the mandated collar snug around my thick neck, a plain white shirt straining over my massive tits and shoulders, and jeans that hugged my wide hips and the heavy sway of my cock and balls. At 6'10", I towered over the cluster of thirty other initiates. Nineteen women catching my eye with their varied curves and glances, the twenty men blending into irrelevance. My hidden pussy tingled with that familiar post-training ache, a reminder of all the ways I'd been stretched, filled, and edged during those Rogue-Harlot drills, but now? Now I was bound for the real deal, the estate proper, where my gentry spot waited like a promise of deeper games. The train rumbled in, sleek and anonymous, doors hissing open to swallow us all. I boarded last, my long strides eating up the space, ducking slightly under the frame as I claimed a spot by the window in the half-full car. Bodies shuffled around me. Perfume and cologne mixing with the faint musk of anticipation. But my gaze snagged on the women, scanning for sparks. That's when they spotted me first, a duo cutting through the crowd like they owned the rhythm of the rails.

Please log in to view the image

Please log in to view the image

The goth shortstack moved like liquid shadow, all busty curves packed into a frame that barely cleared five feet, her half-red, half-black hair cascading in wild waves that screamed 'touch me and regret it. Or don't.' Green eyes locked on mine, sharp and hungry, black lips curling into a smirk that promised mischief. Flanking her was the blonde, athletic and unapologetic, her long golden hair tied back in a ponytail that bounced with each step, blue eyes twinkling with recognition. And yeah, that sizeable bulge in her jeans? It drew my stare for a beat. Futa like me, or close enough. Before she closed the distance, hips swaying with easy confidence. "John Doe? No fucking way," the goth purred, sliding into the seat across from me, her thighs pressing together as she leaned in, cleavage spilling against her shirt like an invitation. Her voice was velvet over gravel, eyes raking down my body, lingering on the outline of my breasts and the denim bulge that never quite hid my 9-inch flaccid length. "Wrestling queen of Wonderland, turning Rogue-Harlot? Saw your matches. Hot as hell. Bet you're even better up close." She bit her black lip, shifting so her knee brushed mine, electric.

The blonde chuckled low, dropping into the seat beside her, close enough that I caught the scent of her. Clean sweat and something floral. "Guilty as charged. I'm Kira," she said, extending a hand, her grip firm when I took it, calluses speaking of her own training grind. "And this firecracker's Raven. We've heard the rumors about you quitting the ring for... this." Her blue eyes dipped to my collar, then lower, bold as she adjusted her stance, that bulge twitching visibly. "Makes a girl wonder what a powerhouse like you craves after all that topping. Care to share the car with us? Or should we make it interesting?" Heat flushed through me, my cock stirring lazily in my jeans as their flirtation wrapped around us like smoke. Raven's foot nudged my calf under the table, teasing, while Kira's gaze held mine, challenging. No men in sight for me to even glance at. These two were all woman, all fire, and in the rocking anonymity of the train, my switch side whispered to play along. "Rumors don't do justice," I rumbled back, voice low and rough from disuse, leaning forward so my shirt pulled tight. "But if you're offering a preview of estate life, ladies... show me what you've got." The train lurched forward, carrying us toward whatever delicious chaos awaited, and I let their energy pull me in, pussy clenching at the possibilities.

Their flirtation hung in the air like the hum of the tracks beneath us, Raven's knee still brushing mine, Kira's blue eyes locked on with that challenging spark. I shifted in my seat, the denim of my jeans pulling tight over my thickening cock, my hidden pussy already warming at the proximity of these two women. Six months of training had honed me sharp. Rogue evasion mixed with Harlot seduction. But it had also unearthed cravings I'd buried under layers of ring dominance. No more masks, the estate demanded authenticity, and with the train rocking us toward it, I let the words spill out, raw and unfiltered. "I did love it, you know. The cucking, the humiliation," I said, my voice a low rumble that cut through the carriage noise, leaning forward so my massive tits strained the white shirt buttons. "In the octagon, nothing beat pinning a married woman down, making her man watch while I fucked his wife senseless right there on the mat. Her moans echoing off the neon lights, his face twisting in that delicious defeat as I claimed her pussy, stretched her wide with every thrust of my cock until she came screaming my name. God, publicly breaking them. Slamming them into submission, their bodies quivering under me as I made them beg for more, humiliating them with every slap of skin and gush of their juices. It was electric."

I paused, feeling the heat rise in my cheeks, but the confession flowed on, lighter now, like shedding weight. "But that's not all I want. Not anymore. I crave freedom. Where I don't have to top every damn time, where I can submit too. Let someone else take the reins, pin me down, use my body however they want. Fill my pussy, make me **** on their strap or cock, edge me until I'm a begging mess. The ring **** me to dominate, but here? I want the balance, the surrender, the thrill of being owned as much as owning." Raven's green eyes widened, her black lips parting in a slow, wicked grin as she absorbed my words, her busty chest heaving with a quick breath. Kira's athletic frame tensed beside her, that sizeable bulge in her jeans twitching visibly as she licked her lips, blue gaze turning molten. "Fuck, Jen," Kira murmured, voice husky, "that's hotter than any match footage. A switch like you? Estate's gonna eat that up." Raven nodded, her half-red, half-black hair swaying as she pulled out a sleek device from her pocket. A standard estate scanner, the kind we all carried for contracts and clearances. "Mind if we peek at that consent form of yours? Just to see how far we can push this preview."

Please log in to view the image

I shrugged, a thrill zipping down my spine as I tilted my collar to expose the embedded chip. "Go ahead. Ticked damn near everything." The scanner beeped softly, projecting a holographic summary between us. Vague outlines of permissions, but the core clause glowed clear: All women granted unrestricted access to initiate, engage, and escalate interactions at their discretion. Raven whistled low, her curvy thighs squeezing together. "Holy shit, it says all women can do whatever they want to you. No limits from your end." Kira's hand brushed my arm, electric. "That's an open invitation if I've ever seen one." Before I could respond, the train swayed, and a new presence slid into the empty seat beside me. Close, her hip pressing warm against mine. She was a curvy and busty brunette, all soft swells and confident poise, her dark hair tumbling in loose waves over shoulders that filled out her white shirt just right, the fabric hinting at full, heavy breasts begging for attention. Hazel eyes flicked up to mine, recognition flashing as she settled in, her jeans hugging wide hips and a plush ass that molded to the cushion. "Jen Smith? The octagon legend herself," she said, voice smooth and teasing, a smile playing on full lips as she crossed her legs, knee grazing my thigh. "Quitting the ring for the estate? Bold move. I'm Lena. Heard you're Rogue-Harlot bound. Makes me curious what a giant like you does when she's not crushing crowds." Her gaze roamed boldly, lingering on my collar, my chest, the subtle outline of my arousal, and the air thickened with her addition, three sets of eyes now fixed on me like predators circling fresh game.

The train hummed onward, slicing through the dimming landscape outside the windows. Rolling hills giving way to shadowed forests as the two-hour journey unfolded without a single halt. Kira, Raven, and now Lena formed a tight circle around me in our row of seats, their presence a constant, electric buzz that kept my nerves alight. We talked in low tones, the conversation weaving through my past glories in the octagon and the pull of the estate's unknown rhythms, their questions probing gently but insistently, drawing out more fragments of my switch nature without pushing into anything physical. Kira leaned back against the window, her long blonde hair catching the fading light, blue eyes flicking between us as she shared snippets of her own Harlot days. Quick escapes from high-society marks, the thrill of turning a chase into a game. "Sounds like your ring moves could translate here," she said, smirking, her athletic frame relaxed but alert. Raven, wedged on my other side, toyed with a strand of her half-red, half-black hair, her green gaze sharp as she described Rogue pranks in the estate's hidden corridors, the kind that left targets flushed and wanting. "Freedom's what you get when you flip the script," she added, her black-nailed fingers drumming lightly on her knee, close enough to mine to send sparks up my leg.

Lena pressed warm against my hip, chimed in with her own tales. She was a curvy **** in the Dolls guild judging by her stories, she explained further, she's specializing in those poised, enigmatic type roles that lured people into vulnerability. Her hazel eyes sparkled with amusement as she recounted a setup where she'd posed as estate decor, only to unravel the scene on her terms. "A giant like you switching sides? That's going to stir things up," she murmured, her full lips curving as she adjusted her position, her bust shifting under her shirt. The three of them traded stories seamlessly, pulling me into the mix, their laughter punctuating the train's steady clatter, building a web of camaraderie that chipped away at my lingering nerves from the wrestling world. I opened up in bits. Admitting how the cucking highs had fuelled me, but the weight of constant dominance had worn thin, how the training had shown me glimpses of yielding that I now chased. They listened without judgment, nodding, offering nods of understanding that made the carriage feel like a confessional. No hands wandered, no touches escalated, it was all words and glances, the air thickening with unspoken promises as the sun dipped low, painting the interior in warm oranges.

The estate's silhouette loomed on the horizon. Towers piercing the twilight sky. The train slowed at last, brakes hissing softly. The doors slid open to a platform bathed in soft lantern glow, and we rose together, the quartet stepping out into the crisp evening air, the estate's pull now tangible, ready to swallow us whole.

What's next?

Want to support CHYOA?
Disable your Ad Blocker! Thanks :)