Framed Jackpot

Becoming Jessica

by BHFun

Tags: #cw:noncon #clothing #dom:male #exhibitionism #humiliation #mind_control #sub:male #bimbofication #TG_Transformation #transformation

I release all my stories for free; however, if you enjoy what you read and would like to support me, please consider subscribing to my website, where I release my chapters up to two months before publicly releasing them. bhfun.com

Chapter Two - Becoming Jessica

The following morning, a dull ache throbbed behind James’s eyes as consciousness crept back in, slow and unwelcome. The mattress beneath him felt wrong, too soft, too narrow, and the sheets lacked his traditional musky scent for a more floral texture. He shifted, trying to roll onto his side the way he always did, but his arm brushed against something rounded and firm that definitely had no business being there.

The contact jolted him fully awake. Memories slammed into him like a freight train: the news broadcast, the cops chasing after him, the abandoned SUV, the knock on Matt’s door, the flamboyant drag queen next door with her glue and her needles and her laughing red mouth. James sat bolt upright with his heart hammering below, and stared down at the smooth, hairless chest now topped with two heavy, perfectly rounded breasts that rose and fell with his panicked breathing. The silicone forms Dixie had glued on last night hadn’t come loose; they sat high and proud, the adhesive holding as if the foreign plastic belonged to him.

The fugitive swung his legs over the side of the bed and stood too quickly, the unfamiliar weight on his chest pulling him forward so that he had to catch the dresser to steady himself. The room came into focus, small and plain, white walls bare except for a single framed print of some generic beach sunset above the bed. He was in some guest room, clearly, nothing like the sprawling master suite he kept at his own place. The feminized man was completely naked, every inch of skin below his neck smooth and hairless from whatever cream he had slathered on the night before. Between his thighs, the chastity device held tight, the false pussy molded over it, giving the illusion of nothing there at all.

James yanked open the closet door, hoping for something, anything, that belonged to a man. Instead, he found a short row of hangers draped with satin and lace. A couple of halter tops, a tiny denim skirt, a latex nurse outfit that belonged on a stripper pole. There wasn’t much, but what was there repulsed the framed man. The drawer beneath was no better, with a neat stack of panties, bras, stockings, and socks in every shade of pastel colors you could imagine. Not only that, but they were clearly designed for a woman who enjoyed showing off her femininity and sex appeal.

“Where the fuck are my clothes from last night?” the man muttered to himself in his familiar baritone, the deep rumble of his own voice giving him a weird sense of comfort.

He scanned the room again, kicking at the bed skirt, checking under the dresser, even dropping to his knees to peer beneath the bed, blonde locks falling over his face. Nothing. The bastard downstairs had taken his clothes away.

James turned back to the drawer and snatched the least offensive item he could find, a plain white g-string. He stepped into it with a grimace, the thin strip of fabric sliding between his ass cheeks and settling into a wedgie that made him clench his jaw, the front fabric fitting flush up against his fake crotch. The pantied man glanced at the other items and shook his head; there was no way he was putting on a bra. Reaching for a hanger, James grabbed a light pink tank top next, soft cotton that stretched tight over his glued-on breasts, the fabric clinging to his unnatural curves. The nipples of the breastforms poked through the thin material, stiff and obvious, but he refused to give in and wear a sissy bra.

From the hanging rack, he pulled a navy blue knee-length pencil skirt that looked almost professional. Despite being a prissy skirt, it was a damn sight better than every other option he had in the closet, so he began to wrestle it up over his hips, the tight fabric hugging the curves caused by the extreme skin-colored corset he was forced into last night. The tank top and skirt didn’t match in the slightest, but it was the least feminine combination he could find in whatever was available to him.

As the runaway General Manager turned to leave, his gaze snagged on the full-length mirror attached to the back of the bedroom door. The sight stopped him cold. The makeup from last night had vanished, but everything else remained. His eyebrows arched in two razor-thin lines that gave his face a perpetual look of startled innocence. Long, dark lashes framed eyes that sparkled an unnatural, vivid blue, nothing like the sharp, fierce green he had glared at the world with yesterday morning. His lips, plump and swollen from whatever filler Dixie had pumped into them, parted in a soft, bee-stung pout that made his face look perpetually ready for a kiss he would never give. The platinum-blonde curls tumbled loose around his shoulders, framing cheekbones that seemed higher, softer, more delicate than any man’s had a right to be.

James stared and gasped. The face in the mirror belonged to some airheaded beauty he would hire for his casinos, not the ruthless manager he knew himself to be. He raised a hand, watching his manicured fingers with the glossy pink tips touch the reflection’s cheek as if it might shatter. The stranger in the glass copied the motion perfectly.

A surge of fury propelled him out of the room. His bare feet padded against the hardwood landing as he stormed down the hallway and descended the stairs.

The scent of fresh coffee hit the feminized man as he reached the bottom. His former employee and recent savior, Matt Turner, stood in the kitchen, leaning against the counter in nothing but low-slung sweatpants, a mug cradled in his hands. His gaze lifted lazily, taking in the mismatched outfit, the far feet, the furious flush on the blonde’s feminized face, and his mouth curved into a slow, satisfied smile.

“Good morning, Jessica,” he said, his voice warm with amusement. “Did you sleep well?”

“Don’t call me that!” James snapped as he stepped in the doorway, his fists clenching at his sides in a way that scratched his palms. “Now cut the crap. Where are my clothes? And why does my face still look like this?”

Matt moved forward and set his mug down on the table with deliberate calm, before folding his arms across his bare chest. He let the silence stretch just long enough for James to feel the weight of those swollen lips and ridiculous lashes.

“I threw your old suit out, burned it in a bonfire in the backyard, actually,” he said calmly, his tone matter-of-fact. “I can’t have the cops sniffing around here and discovering the very same outfit you were last seen in now, can I? It’s not like you’ll need a suit like that for some time, anyway.”

James opened his mouth to argue, but Matt raised a hand and kept talking.

“As for the face, that’s permanent for now. The lips, the brows, the lashes, the color contacts. Dixon doesn’t do half measures. You’re not playing Jessica part-time. You’re playing her until your name is cleared, and that could take weeks, maybe months. You need to look the part every day, not just when it’s convenient.”

James felt the blood drain from his cheeks, the pout of his mouth making the expression look almost comical. “Months? I don’t think so…”

“You may not have a choice, Jessica,” the homeowner replied, using the alternate name he had given James once again. “You want a chance to clear your name? You have to play by my rules, and this is the best idea I have. After the close call we had with the detective last night, we have to be extra careful.”

The blonde-wigged man crossed his arms under the heavy breasts, the motion making them jiggle under the tank top slightly and drawing Matt’s gaze for a fraction of a second. “Well, your idea is stupid,” he growled, the deep baritone rumbling out of that delicate, pouty mouth like gravel pouring over silk.

Matt grimaced at the sound, his nose wrinkling as if he had smelled something sour. “And that voice is what’s going to give you away the second you open that pretty mouth in public,” he said, pushing off the counter and stepping closer. “You sound like a linebacker while looking like a cheerleader. No one’s going to buy the innocent-little-sister cover story with that coming out of those lips.”

He paused, letting the words sink in, then continued in the same measured tone. “We need to fix it. Say this after me, and say it in the highest, breathiest, most feminine voice you can manage: ‘I am a girl.’ Go on.”

The blonde stared at his former subordinate in disbelief. “I’m not saying that!” he growled out.

Matt sighed before turning and reaching for his cell phone on the kitchen table. “Fine. Then we may as well forget the whole thing and hand you in to the cops right now. I’m sure Detective Sanders would love to nip his investigation in the bud.”

James watched Matt’s thumb hover over the screen, and panic surged through his body. Surely he was bluffing. But what if he wasn’t? James just couldn’t take the risk, especially with him looking as he did.

“Wait,” he blurted, the word coming out rough and desperate. He swallowed hard and gave in to his host’s request, forcing his throat higher, lighter. “I… I am a girl.” He felt a flush of humiliation as he dropped his head.

The attempt sounded forced, a bad falsetto that cracked halfway through, still too deep, too obviously male. Matt lowered the phone but shook his head, unimpressed.

“That was horrible,” he said flatly. “You need to try harder. Really sell it. Like you were born to be a woman.”

James closed his eyes, humiliation burning in his chest as the glued breasts rose and fell with each breath, the tickling of the long eyelashes against his skin prompting him to shudder. He pictured various actresses, how they spoke and carried themselves. He could do this.

“I am a girl,” he tried again, pushing his voice up, letting it waver and lilt. It came out breathy this time, higher, but still carried the gravel of a man who was proud of his masculinity.

The brunette homeowner sighed and rubbed the bridge of his nose, the disappointment evident in his posture. He had hoped he would not have to use this, but the stubborn man in front of him left him no choice.

He walked over to a kitchen cabinet and opened it, rummaging around for a moment before returning to James with a small pink pill in his palm and a glass of water he had filled from the sink.

James eyed the pill suspiciously, his arms still crossed under the heavy weight of his fake chest. “What is that?” he asked, the deep timbre of his voice making the question sound more like a threat.

Matt held the pill out, his expression unreadable. “Take it.”

The feminized man didn’t move, his gaze flicking from the pill to Matt’s face and back again. “I’m not taking anything until you tell me what it is.”

The brunette man’s patience thinned, his voice rising. “Just take the damn thing before I call this experiment off.”

James knew he was trapped. He had no idea what the pill did, and it looked ominous and threatening. However, he had no choice. Taking one final look at the small pink pill, he took it from Matt’s hand and tossed it into his mouth, taking a long gulp of water to wash it down.

The blonde swallowed hard and set the glass down on the coffee table. The pill scraped going down, leaving a chalky film on his tongue that tasted of chemical bleach. He cleared his throat, only to be greeted by a hoarse cough. There was a burn low in his chest, which raced upwards as a tight, pinching sensation wrapped around his vocal cords like invisible fingers were squeezing the smaller.

“Ugh, that tasted like absolute shit,” he managed, the words starting in his usual baritone before pitching upward into something else entirely. The blonde’s eyes widened as the last syllable squeaked out in a bubbly, ultra-high soprano that belonged more to a cartoon princess.

Matt’s grins spread wide and triumphant, his hazel eyes gleaming with pure amusement.

James clapped both hands over his mouth, the glossy pink nails flashing as his face flushed red. He tried again, forcing the words out harder this time. “What the fuck have you done to me?”

The question came out in a breathy, girlish lilt, every syllable dripping with sugar and air, the kind of voice that made men want to buy a girl drinks and made women roll their eyes. It was impossible high, impossible feminine, and utterly inescapable.

Matt folded his arms as he stepped back and leaned back against the counter, savoring the moment. “Dixon slipped me a bottle last night as a last resort,” he said casually, as if discussing last night’s game. “The queens at the club use them when they need to stay in character all night. It tightens everything up and gives them that feminine sound they need. It comes in all kinds of different strengths, but he swore this one would be exactly what someone like you needed. I think he was right.” He grinned with amusement.

James dropped his hands, staring at Matt in open-mouthed horror, those swollen lips forming a perfect O of shock that only made the voice sound even more ridiculous when he spoke again. “I sound like a fucking twelve-year-old valley girl!”

The words floated out light and bubbly, entirely at odds with the fury burning behind the blue eyes.

Matt tilted his head, pretending to consider it. “Maybe a touch high,” he allowed, amusement thick in his tone, “but it’ll do the job beautifully. No one’s going to hear James Harper in that voice, trust me.”

James took a step forward. “Fix it,” he demanded, except the demand came out as a breathy, pleading whine that would have made any man want to pat his head and promise to take care of everything.

The brunette man shook his head, pushing off the counter and closing the distance between the pair. “I can’t exactly fix it,” he said softly. “However, the effects only last twenty-four hours. You’ll need to take one every morning to continue sounding like that.”

James groaned and took a barefoot step back, but Matt stepped forward to keep the distance close. “Listen carefully, Jessica,” Matt continued. “I’ve already secured you a job at the casino, so my ass is on the line now. I managed to land you a spot as a cocktail waitress, and your first shift starts tonight. Don’t disappoint me.”

The blonde’s newly blue eyes went wide, the long lashes fluttering as he gasped in panic. “Tonight?” The words came out as a squeal, high enough to make him wince. “How the hell will I be ready to be seen in public by tonight?”

Matt’s smile turned predatory. “Oh, Jessica,” he said smoothly. “We both know someone who’d be very happy to help with that.” He looked James up and down before heading toward the staircase. “Make yourself a coffee and some breakfast, Jess. He’ll be here soon.”

The man ascended the stairs, leaving a shocked and dumbfounded James alone to contemplate his humiliating future.

James sat on the edge of the couch, pitying himself for how his life had changed so drastically in just twenty-four hours. The voice in his head now sounded nothing like the chirpy, airheaded voice that escaped his pretty mouth, and he just wanted to go to sleep and put this nightmare behind him. The blonde stared at the coffee table as his thoughts swirled, trying to ignore the way his glued forms weighed him down as he slouched over.

Then, a knock sounded at the front door, breaking the silence. Matt moved from the full-length mirror at the bottom of the stairs, buttoning the last few buttons on his ironed white shirt as he headed to the entrance. He opened the door, and a lean man stepped inside, shoulder-length black hair slicked back, dark brown eyes sparkling with mischief. He wore fitted jeans and a bright teal button-up shirt that showed off his slim figure.

The visitor gave Matt a hug before turning to James, his gaze landing immediately on him, his face lighting up with theatrical delight. “Well, hello again, gorgeous,” the man said with playful, campy warmth as he moved to the front of the sofa. “It’s so good to see you again, doll. Though that mismatched outfit is a total crime against humanity.”

James raised an eyebrow, the high arch making the motion look more delicate than he intended. “Uhm, do I know you?”

Matt closed the door and walked over, jovial amusement dancing in his eyes. “Dixon does look a little different when he’s not in character, I guess,” he explained.

James’s plump lips parted in the realization. The man standing before him was the flamboyant fruitcake who did all this to him, the blonde thought to himself. “Dixie?” he said in a high-pitched squeak before he could stop himself.

Dixon chuckled, the sound low and genuine as he sauntered closer to the feminized man. “In the flesh, darling. I love your voice by the way, so fetching,” he teased. “I only dress as Dixie when I’m working. However, Matt called and said some pretty lady needs to get ready for her first day of work.” The campy man tilted his head, taking in the travesty of an outfit with a critical eye. “And from the looks of things, we have our work cut out for us.”

James felt heat rush to his cheeks, the blush obvious on his unmade-up face. He crossed his arms tighter under the heavy breasts, the motion only serving to push them higher against the thin cotton. “Just get it over with,” he muttered, rudely, the squeaky soprano turning the demand into something closer to a pouty whine.

The flamboyant guest clapped once, his bracelets jingling, and set a large black case on the coffee table. “Music to my ears, princess. Stand up and strip.” He turned his head to Matt. “Won’t you be a doll and grab Jessica’s uniform while we get to work?”

Matt disappeared up the stairs without a word, leaving James alone with the man who had turned him into this the night before. Dixon waited expectantly, one eyebrow raised in challenge, and James knew resistance would only drag the humiliation out longer.

He rose from the couch and reached for the hem of the pink tank top. The cotton peeled away from his skin with ease, the glued, realistic-looking breast forms bouncing free, heavy and foreign. Dixon’s gaze lingered appreciatively, but he said nothing as the blonde shoved the skirt down his hips and stepped out of it, the white g-string the only thing left clinging to his body.

The dark-haired drag queen motioned toward a dining room chair he had already positioned under better light. James sat, the wood cool against his bare skin, and Dixon wasted no time. He opened the case and began working with the efficiency of someone who had done this a thousand times on himself and others.

The makeup artist started with the hair, brushing out the platinum curls until they fell in perfect, glossy waves, then pinned a few sections higher for volume that framed the face like a halo of sin. James sat rigid, eyes fixed on the wall, feeling every tug and spray as the style locked into place.

Next came the face. Dixon worked in silence now, brushes whispering over skin, powders settling in layers that changed the shape of his cheekbones and the depths of his eyes. The gay man lined and shadowed, built and blended, the occasional click of a compact the only sound. The blonde felt a brush flutter against his lengthened eyelashes, the cool swipe of liner, the sticky pull of gloss across his swollen lips. The fugitive wanted to demand a mirror, wanted to see what fresh hell was being painted on him. Still, the squeaky voice stayed behind his clenched teeth.

Footsteps sounded on the stairs. Matt returned carrying a hanger draped in shimmering silver. Dixon glanced up, took one look at the uniform, and let out a low whistle. “You’re sending her straight to the high-roller room, honey?” he asked with a grin. “Someone has a lot of faith in our budding beauty.”

James’s gaze snapped to the hanger, and his stomach dropped. The dress—if it could be called that—was a halter neck micro of liquid silver sequins, cut so low the side of the breasts would be on show whenever he moved, hem barely long enough to cover the curve of an ass. Matching clear 5-inch stripper heels and silver fishnet stockings dangled from the host’s other hand.

“What the fuck is that?” James squeaked. “I know most of your waitresses don’t have to wear that shit, so put that away.”

The F&B manager shook his head slowly, the hanger still extended like an offering he knew would be accepted in the end. “Unfortunately, the only vacancy open right now is on the VIP floor,” he said flatly. “None of the regular girls want to make the step up yet, so I have no choice but to put you in the role.”

The blonde stared at the shimmering scrap of fabric with disgust. “There’s no way in hell I’m wearing that,” he insisted, the high-pitched voice sounding childish and petulant as he stood his ground.

Matt grinned and casually pulled his phone from his pocket and thumbed the screen awake. “No problem,” he said. “I just have a phone call to make.” He grinned as he turned his back on James and Dixon, the implications sounding loud and clear in the feminized man’s mind.

James’s eyes widened, and he felt the fight drain out of him all at once. His 34D breasts rose and fell as he breathed in panic. “Alright, alright,” he replied as his fingers reached for the hanger.

Dixon watched the exchange with one eyebrow arched high, curiosity flickering behind the playful mask, but he kept his mouth shut. Whatever was going on between these two was none of his business, but he loved a good gossip and conspiracy.

James took the dress and slowly stepped into it, the sequins sliding sensuously over his smooth skin. The halter tied behind his back, an act Dixon helped him with, the fabric stretching tight across the heavy forms, plunging so deep that the inner curves spilled into view with every breath.

“It’s a good thing you’re averse to wearing bras, honey,” Dixon commented. “It would be impossible in this thing anyway.”

The feminized man ignored his tormentor’s remark and straightened the dress up, the back cut low enough to reveal the humiliating curve of the g-string above his ass. He found he was in a sticky spot. The dress only just managed to cover his ass, but if he pulled it down further, it would show off more of his breasts. However, if he tried to cover his fake tits up, the dress would rise and show off his derriere.

Dixon pushed James back onto the chair before kneeling to roll the silver fishnets up the man’s legs, the mesh sliding against his hairless, smooth skin. There was a good 3-inch gap between the lace of the stockings and the hem of James’s dress, giving him a uniquely slutty aesthetic. Dixon finally buckled the clear platforms around each ankle, the five-inch lift forcing James to point his toes. The gay man helped James up as he wobbled, struggling to keep his balance and needing to rest his hand on Dixon’s shoulder to stay upright.

The dark-haired drag queen steadied James with both hands on his hips. He gave an approving once-over, then spun the blonde around with a flourish and marched him toward the mirror at the bottom of the stairs.

“Feast your eyes, princess,” Dixon purred, stepping aside so James had no choice but to face the reflection head-on.

The woman staring back looked built for one purpose and one purpose only: entertainment. Wavy platinum blonde hair tumbled in glossy, teased perfection, framing a face that screamed expensive fantasy. Smoky silver shadow swept across the woman’s lids, making the vivid blue eyes look enormous and perpetually wide with innocent shock. Black line winged out sharp and dramatic, lashes so long and thick they brushed just below the arched brows as they opened wide. Cheekbones shimmered under layers of highlight, giving the face a sculpted, almost plastic glow, while the swollen lips glistened candy-pink, parted just enough to look inviting and vacant at the same time.

The silver sequined halter dress strained against the heavy D-cup forms, the plunge so deep that the inner curves spilled forward, threatening to escape entirely. The fabric clung tight to the smooth skin, stopping high enough on the thigh to flash the lace tops of the fishnets adorning her legs. Clear platform heels lifted the legs into an endless line, forcing the ass to jut out in shameless display.

James stood frozen, the squeaky gasp that escaped those glossy lips the only sound in the hallway. The reflection was pure high-roller bait, the kind of girl men threw thousand-dollar tips at just to watch bend over to pick up. Every inch screamed sex, from the teased hair to the painted face to the body poured into silver like it had been designed in some back-room fantasy. But worst of all, the sex kitten in the mirror was him. How was this possible?

Matt stepped up behind the transformed man, resting both hands on his shoulders, meeting the reflection’s horrified stare. “Isn’t Dixon a magician or what?” he asked rhetorically. “I think you’re finally ready to earn your rent, Jessica.”

The host backed away and thanked Dixon, leading his next-door neighbor back to the front door as James stared gormlessly at the sexy woman in the mirror. How was this possible? How had he gone from commanding general manager to sexy cocktail waitress in under a day? As he heard the door close, he knew the time was ticking until Jessica’s humiliating debut.

The late-afternoon sun slanted through the windshield as Matt guided his car onto the ramp that led beneath the Royal Crest Hotel & Casino. James sat rigid in the passenger seat, arms folded tight beneath the heavy swell of silicone that strained against his barely-there dress. The platform heels forced his knees up as he stared dead ahead, his jaw clenched and lips pressed into a glossy pink line that only made the pout look sulky and inviting.

Matt flicked the indicator and eased into a staff space marked with yellow paint. He killed the engine and turned toward his undercover charge, one eyebrow raised in amusement.

“You could at least try to look less miserable,” he said mockingly. “You got yourself in this mess after all. You didn’t have to go through with this. It’s not too late to turn yourself in.”

The feminized man refused to reply. E kept his gaze fixed on the concrete wall ahead, arms still locked across his chest as if he could hide the plunging neckline through sheer willpower.

The man in the suit chuckled and opened the door. “Fine. Stay quiet. Remember, you just need to blend in, learn the tricks of the trade, and in just a few days you’ll have free access to the back of house where you can search for the evidence you need to clear your name.”

He stepped out and circled to the passenger side, pulling the door open with a mocking bow. James hesitated; he didn’t want to leave the car, and he certainly didn’t want anyone seeing him like this. However, the feminized man relented and stood from his seat. The platforms he wasn’t yet used to made the motion clumsy as Matt shut the door behind him and pressed the key fob, the car chirping in response.

Matt led the way toward the staff entrance without waiting. James followed, precariously trying to keep up with each step, his heels clicking loudly against the concrete in the underground garage. The feminized blonde attempted to ignore the leers of every male employee the moment he set foot in the building. He had never felt so humiliated in his life, and he hadn’t even started the undercover job yet. A porter pushing an empty cart slowed to stare openly, his eyes traveling from the wavy hair to the impressive silhouette of his fake tits. James kept his gaze fixed on Matt’s back, trying his best to act like he didn’t notice the stare.

They passed through a heavy metal door into the back-of-house corridors. The noise hit at once, shouted orders in between kitchens, the clatter of trays, the distant thump of music from the main floor above. Male cooks and porters turned as they walked past, conversations dying with their gazes lingered on the silver-clad newcomer. One whistled low under his breath, which elicited a chorus of chuckles from his friends.

James felt every stare like intrusive fingers on his skin. He wanted to snarl, to tell them all to fuck off in his real voice. Still, he knew what he sounded like now, and how his voice would remain for the next 18 hours, and he also knew how he needed to play nice if he were to escape this nightmare. Work was all about politics, and James knew a thing or two about corporate politics.

Matt guided his new ‘employee’ up past the main floor and onto the VIP mezzanine above. The bar gleamed with dark wood and fancy chrome, with only the top-shelf booze on offer under the amber lighting. A small handful of early high-rollers already occupied their seats at the tables and slots, a couple of them turning their heads to view the newest hostess.

Matt approached the bar, where an attractive woman with auburn hair in a sleek ponytail stood, wiping down the surface. She wore the same silver sequined uniform as James, though her much smaller bosom seemed to fit the attire better and looked far more presentable. Her green eyes flicked up as the pair neared, and her glossy red lips curled into a wide smile that carried a familiar warmth.

“Hey, Maddie,” Matt said, leaning in to give the woman a hug. “How’s my favorite team leader doing?”

Maddie returned the embrace as they hugged for a moment before the woman pulled away and rested both palms on the bar. “I’m doing just fine, babe,” she answered confidently. “And who is this ray of sunshine?” She asked, glancing at the shy-looking blonde behind the F&B manager.

Matt straightened and gestured toward his former boss with an easy smile. “This is Jessica, my little sister. She just moved down from Vicksburg and needs a job. I figured I’d give her a helping hand, and we could use an extra pair of heels on the floor. Go easy on her, yeah?”

The auburn-haired woman’s gaze traveled over James from head to toe, lingering on the plunging neckline and the way the dress clung to every curve. Her smile stayed in place, but something sharpened behind her eyes. “Well,” he said, her voice dripping honey, “she certainly knows how to fill out that uniform.”

James felt the heat crawl up his neck, the blush burning beneath the heavy makeup Dixon had layered on earlier. He forced his arms to the sides, the motion only drawing more attention to the way the sequins strained across his chest. A pair of gamblers at the nearest blackjack table had stopped playing entirely, their eyes fixed on the new girl like wolves spotting fresh meat.

Matt laughed. “I think you two will get on like a house on fire,” he said, resting his hand on James’s shoulder. “She just needs a little friendly guidance.”

Maddie’s smile widened, all teeth. “Oh, I’ll take very good care of her,” she said as she slipped her arm around the feminized man’s waist, pulling him away from Matt and toward the bar. “After all, she’s family.”

The dark-haired F&B manager gave the pair a wink and stepped back. “I’ll leave you two to get acquainted. Have fun, Jess.”

Matt walked away without another glance, his footsteps fading toward the back of house area. The moment he disappeared, the warmth in Maddie’s expression evaporated. She released James’s waist as if the touch suddenly disgusted her and planted both hands on her own hips, her eyes narrowing as she glanced at her newest employee.

“So,” she said, her voice suddenly icy. “What hospitality experience do you have, sweetheart?”

James swallowed, the movement making the halter shift against his glued forms. He had plenty of hospitality experience before, but he was supposed to act like some 22-year-old girl from a backwater town. How was he supposed to do that? The blonde decided to take the easy route. “Uhmm,” he stuttered in his squeaky soprano. “This is my first job in hospitality.”

Maddie rolled her eyes the moment she heard James’s voice. She leaned forward on the bar, her red nails tapping an impatient rhythm against the wood. “Of course it is,” she muttered. “Look, I don’t have time to train some redneck bimbo just because her big brother is my boss, understand?”

The insult landed like a slap. James opened his mouth to protest, but the only sound that came out was a soft, breathy exhale as he didn’t know how to act.

The floor supervisor straightened up, smoothing an invisible wrinkle from her own dress. “Listen up, Jessica. I don’t do nepotism. Family connections mean nothing on my floor. I’m the boss around here, and my word is your bible. If you make me look bad, we’re going to have problems, you got it?”

The blonde shuddered and felt the weight of every stare from the nearby tables, the gamblers pretending to play while their eyes stayed fixed on the drama at the bar. He managed a tiny nod, the blonde curls of his stuck-on wig brushing his bare shoulders.

“Good,” Maddie said, her smile returning. “Now head backstage and find Daisy. She’ll give you whatever training that pretty little head can handle.”

She turned away without another word, her hips swaying as she moved toward the ice bin, already dismissing him.

James stood rooted for a heartbeat longer, his pulse hammering in his ears. The VIP floor stretched out around him, and he felt incredibly small and helpless. Could he really do this? He thought to himself.

The question burned in his skull as he forced his platforms to move, one wobbling step after another, toward whatever fresh hell waited backstage.

The humiliated James pushed through the staff-only door into the narrow backstage corridor and looked around. That bitch told him to find Daisy, but he had no idea where to start looking. He spotted a waitress wearing the more modest red dress uniform of the main floor scrolling on her phone, obviously enjoying her break in peace.

The feminized man tottered over to her and cleared his throat, the sound coming out in that ridiculous squeak. “Excuse me. Do you know where Daisy is?”

The dark-haired woman glanced up, took one look at the platinum curls and plunging halter, and her mouth twisted into a scowl. She returned to her screen without a word and walked away, her hips swaying with deliberate indifference. What the fuck was her problem? James wondered.

James stood there, his long fingernails crashing into his palms as his hands formed frustrated fists, when a male table dealer in a white shirt and black vest appeared beside him. Tall, dark hair, easy smile. His eyes traveled down the length of the silver dress and back up again, lingering just long enough to make the point.

“I couldn’t help overhearing,” the dealer said smoothly. “Daisy just headed down to the cellar for some fresh bottles. I can take you to her if you like.”

James forced a tight smile from his overinflated pink lips. “Thanks. That would be great.”

The dealer extended a hand. “Luca.”

“Jessica,” the blonde answered, the name tasting wrong on his tongue.

Luca’s grin widened. “No problem at all, Jessica.”

He started walking, and James had no choice but to follow. Halfway down the corridor, Luca’s hand settled on the small of the scantily-clad undercover waitress’s back, then slid lower, palm cupping the curve of an ass cheek through the thin sequins. James stiffened, every muscle locking, but Luca kept talking like nothing was happening.

“So, first night on the VIP floor? I saw you talking to Maddie up there,” he asked conversationally, fingers giving a light squeeze. “You’ll do great. You really got the body to fill out that uniform properly.”

James opened his mouth to snap something, but his mind was conflicted between giving the overconfident dealer a piece of his mind and simply staying out of trouble. The result was a nervous laugh that sounded an awful lot like a vapid giggle from his high-pitched vocal register. Luca’s thumb traced lazy circles as they walked, and they reached the cellar door before James could figure out how to make the man remove his hand without causing a scene.

Daisy stood just outside, arms full of champagne bottles, her brunette ponytail swinging as she turned. She took one look at Luca’s hand placement and rolled her eyes. “Luca, do your hands need another sexual-harassment seminar?” she said dryly.

Luca moved his hand away and lifted both palms up in mock surrender, taking a step back. “Just being friendly, Daisy,” he said, winking at the experienced waitress before sauntering off.

The brunette shook her head and set the bottles on a crate, and offered James a warm, genuine smile that felt like the first kindness he’d tasted all day. “If you’re gonna survive around here, hon,” she started, “you need to learn how to shrug off advances while still playing nice. It’s a skill.”

James offered a subtle nod.

“Anyway, you must be Jessica,” the woman said, brushing a loose strand behind her ear before extending a hand, her long French-tipped fingernails outstretched. “I’m Daisy. Maddie said you needed training. Let’s go somewhere private and get you started before the floor eats you alive.”

Daisy led them into a small, unused storage room lit by a single bulb that swung overhead. It looked like one of those rooms in the old casino movies they’d take you to break your legs or smash your fingers. The brunette set an empty silver serving tray on the table and turned to face her new student.

“First things first,” she said. “You walk like you’re afraid of those heels. They take some getting used to, especially if you’re used to the practical footwear on the main floor, but you gotta own them. Place your shoulders back, chest out, hips loose, and stare directly at where you’re heading. Watch me.”

The experienced waitress took three smooth steps across the room, her tray balanced effortlessly on one palm, her hips rolling in a slow, confident rhythm. Every movement looked natural and practiced, the kind of sway that made James’s trapped, locked-away cock shift, prompting the blonde to gasp.

James swallowed and tried to copy her. The platforms threw his balance forward, and the tray wobbled dangerously. He caught it just before an empty glass slid off the edge.

Daisy winced but kept her tone gentle. “Again. Slower this time. Feel the weight in your hips, not your knees.”

The feminized man tried a second time. The tray steadied for two steps before tipping. The glass hit the floor and shattered, shards scattering across the concrete.

The trainer sighed and crouched to pick up the large pieces. “It’s okay. Everyone drops a glass once in a while. Just breathe.”

James stood frozen, cheeks burning beneath the makeup. How the hell had he gotten into this predicament? Two days ago, he was riding high, openly enjoying the view of the waitresses he forced to dress as he was now. How had it all gone so wrong so quickly? He needed to make this work so he could get rid of these tits and go back to working in suits.

“Next,” Daisy said, standing and brushing glass from her fingers. “The lean. When you hand a drink, you bend at the hips, not the waist. It keeps the tray level and gives the customer a nice view without making it look like you’re trying too hard. This is how we make our tips.”

She demonstrated, bending smoothly, her tray steady and her smile bright. The motion was pure invitation without ever crossing into the crude or inappropriate.

James tried. However, his bend was too sharp and quick, and he looked like an oaf bending forward without an ounce of grace in the world.

Daisy closed her eyes for a moment. How the hell did someone looking like this have the grace of an ogre? She wondered. The brunette reopened her eyes and offered a patient smile. “We’ll get there. Let’s try the smile. Men tip for the fantasy of a night with you. They won’t ever realize that fantasy, but it’s good to give them a naughty glimpse.”

James sighed, not wanting to play along but finding himself with no choice. He forced his glossy lips into a bright smile, finally something that ignited a positive response from his trainer. “Wow, beautiful,” she remarked. “Now we have something to work with.”

Half an hour passed in a blur of dropped glasses, wobbling trays, and Daisy’s endless patience. James’s arms ached from holding the tray constantly, and his calves burned from the platforms.

Footsteps approached fast from the corridor, and Maddie appeared in the doorway, her expression stern. “There you two are,” she said with an impatient tone. “Daisy, I need you and Jessica on the floor now,” he said. “Mr. West just walked in, and we need all the help we can get.”

Daisy glanced at the scattered glass, then at James, worry flickering across her face. “Now? She’s not nearly ready enough to start yet, Maddie.”

Maddie’s smile didn’t reach her eyes. “She doesn’t have a choice. Now move, both of you!” The team leader turned on her heel and disappeared.

The brunette waitress sighed, flicking a strand of hair to one side. “Well, I guess it’s time for your debut, Jessica,” she said with slight worry in her throat. “Go out there and show them what you’ve learned.”

James stared at the doorway Maddie had vanished through, the tray still trembling in his manicured hands, and felt the first real spike of dread settle down his spine. How was he going to navigate this humiliating challenge?

The F&B Team Leader, Maddie Waters, stood at the edge of the VIP floor with her arms folded, watching her newest charge wobble toward a quiet corner table where two small-time VIPs sat at a Blackjack table. She had deliberately assigned him the dead section, far from the real money and far from Kevin West’s usual perch at Baccarat 4. Mr. West was one of the Royal Crest’s biggest fish, and Maddie wasn’t going to give her new girl an opportunity to humiliate the department in front of him. James had attempted to poach the high roller a few months ago, but the wealthy man remained loyal to the competitor.

James held out the silver tray as he had been trained, two flutes of house champagne balanced precariously. The platforms made every step a gamble as he tottered slowly toward the two men. The blonde almost reached the table when he misjudged a step forward, his heel twisting as the tray caught off balance. One flute slid, then another, and before he could catch them, the pair of glasses, along with the bottle, crashed to the carpet in a spectacular explosion of glass.

The two players jumped back, startled by the noise. Heads turned from every direction as Maddie quietly grinned to herself, knowing she had this girl’s ‘skills’ figured out from the beginning. She didn’t need to babysit her boss’s baby sister.

James knelt down in humiliation, his ankle killing him, and began to collect the large shards of glass that fell at the foot of the gaming table. When she approached the bar with the broken glass sitting on the tray, the female bartender leaned over the counter and spoke with a sharp hiss. “That was Dom Perignon, you dopey bitch,” she snarled. “The cost of the bottle is coming out of your tips.”

The feminized man stood frozen at the bar, the tray of broken glass trembling in his manicured hands, while the bartender continued her scolding tirade about how many hours he would have to work to cover the cost. Every eye on the VIP floor seemed to be on him now, some amused, some annoyed.

Maddie moved from her perch and glided across the floor effortlessly in her own stilettos, heading over toward the high-stakes Baccarat table where Mr. West sat with a growing stack of chips. She bent low beside him, the sequins of her dress catching the light as she offered her sweetest smile.

“How has your visit been tonight, Mr. West?” she asked.

Kevin didn’t even glance at her. His eyes were fixed across the room on the blonde now removing the broken shards of glass from her tray, the silver dress stretched tight across her ass as she bent over the bar.

He chuckled a filthy laugh. “Who’s the new girl?”

Maddie followed his gaze and kept her expression pleasant. “That’s Jessica. She’s in training at the moment.”

The high roller’s tongue traced his lower lip as he watched the blonde stand. “Training, huh?” he said with amusement. “I like her. I want her serving me for the rest of the night.”

The team leader’s smile stayed in place, but her fingers curled against her palm. “Uhmm, I’m sorry, Mr. West,” she stammered. “I’m afraid that’s not possible. We always aim to give you the very best, and Jessica isn’t quite ready to give you the top service you need. Tiffany has been looking after you all evening and—”

Kevin cut her off with a lazy wave. “Your job is to give me exactly what I ask for, sweetheart. And right now I’m asking for the new girl.”

Maddie felt the words land like a slap. She was caught between a rock and a hard place. She knew the clumsy new girl shouldn’t be anywhere near the most valuable players, but she also knew she needed to keep the high roller happy, and he wouldn’t take no for an answer. She nodded once as she stood straight. “Of course, sir.”

She turned on her heel and crossed the floor to the bar, where the bartender was still hissing at the undercover waitress. “Change of plans,” Maddie interrupted. “Jessica’s been reassigned to VIP Baccarat 4 for the rest of the night.”

The bartender’s jaw dropped. “Are you serious?” she snapped.

“Customer request,” Maddie replied, looking over at the important man.

James looked up and followed the supervisor’s gaze across the room. Kevin West raised his almost empty scotch glass in a mocking salute, that slimy smile never leaving his face, eyes locked on the silver-clad blonde like she belonged to him.

Maddie stepped beside the blonde, her voice quiet enough so only she could hear. “Get over there and introduce yourself. Mr. West is an important player, so try not to get yourself fired.”

James lowered his head, gripped his tray, and forced his legs to move. He still couldn’t walk competently on the tall heels, something Kevin had noticed, which made his grin grow wider.

Kevin leaned back in his chair as James approached, his legs spread wide. His stare crawled over every inch of the blonde’s busty appearance, lingering on the plunging neckline. “Well, hello there, gorgeous,” the man drawled. “I hear you’re new around here. Are you here to come take care of me?”

The undercover blonde swallowed, the squeaky voice he had tried to limit trembling as he forced the words out. “Hi, sir. I’m Jessica, and I’ll be your server tonight.”

The man’s grin widened. He reached out without asking, his fingers brushing the inside of James’s wrist before sliding up to toy with a strand of his luscious hair. “Jessica,” he repeated, testing the name. “Pretty name for a pretty girl. Jessica, bring me another scotch; the bartender knows what I like. And take your time coming back. I love watching you walk away.”

James managed a tiny nod and turned carefully, terrified of another fall. He started the long walk back to the bar, feeling the perverted high roller’s ass burning into his ass as he tottered precariously.

At the bar, the same bartender who had just torn into him now looked almost sympathetic. She poured the scotch without a word, sliding the heavy crystal glass across the polished wood.

James placed the drink on the tray and lifted the surface; the single glass centered perfectly this time. He turned, took a breath, and started the return journey. The platform heels made his hips roll whether he wanted them to or not, the most exaggerated and unmistakable. Kevin watched every second, lips parted, completely ignoring the baccarat game as he enjoyed the show.

The blonde reached the table without disaster and bent at the hips the way Daisy had shown him, offering the glass with both hands. James looked uncomfortable and rigid, but at least he stayed on his feet this time. Kevin took it slowly, keeping his eyes on James as he did.

“Thank you, Jessica,” he said, drawing the name out like he was tasting it. “You’re doing just fine.”

From across the room, Maddie watched the exchange with her arms folded tight, her smile long gone.

The general manager of the casino, and James’s arch-nemesis, Clifford Moss, appeared at Maddie’s elbow without warning. The woman startled, nearly toppling over in her own heels as the man stood beside her.

“Who’s the new girl?” the general manager asked, his gaze fixed on the silver-clad figure now trapped at Kevin’s table.

Maddie recovered quickly. “Jessica Turner. She’s Matt’s little sister. She’s been an absolute disaster so far.”

Clifford’s eyes narrowed, noticing the nervousness in the scantily clad blonde’s posture. “Well, why is she serving Kevin West, then?”

“Mr. West requested her,” Maddie replied through gritted teeth. “I tried to steer him in the other direction, but you know how he can get.”

Clifford nodded slowly. “Mhmm,” he muttered as he watched the scene. “I understand what he sees in her.”

The auburn-haired team leader straightened. What is up with these men, she thought. “She’s been a trainwreck so far. Lord knows how many glasses she’s broken today, and she can’t even stand in her footwear. I’ll let her go when her shift is through.”

“No,” the 40-year-old man snapped. “You won’t let her go, not without my permission.” He turned his head to his trusted waitress. “Get her trained properly. That’s an order, Maddie.”

The general manager walked away before Maddie could retort, leaving her staring after him with fury burning behind her eyes. She turned her head back to the floor, watching Kevin’s hand slide possessively to the small of a visibly nervous James’s back. Maddie groaned and muttered under her breath.”

“I’ll train her up, alright.”

James sat rigid in the passenger seat of Matt’s car, his arms locked so tight across his chest that the glued breastforms pressed painfully against his forearms. The platform heels lay discarded on the floor mat, kicked off the moment the car door shut, leaving his stockinged feet curled up below him.

Matt guided the car through the quiet streets, one hand relaxed on the wheel, the other resting on the gearshift. He glanced sideways and chuckled under his breath. “You need to calm down, James,” he said with amusement, purposefully choosing to use the feminized man’s real name. “You look like you’re about to explode.”

James whipped his blonde-haired head around with fury. “That’s easy for you to say,” he squeaked, the high-pitched soprano making the words sound more petulant than the anger he intended. “I’m not some dumb blonde waitress. I’m done with this shit.”

The former subordinate’s grin widened, his eyes flicking back to the road. “If you have any better ideas, I’m all ears. Feel free to share them.”

Silence stretched between the pair, thick and angry. James stared out the windshield, his lips pressed into an amusing glossy pout, his fists clenched so hard the acrylic nails dug half-moons into his palms.

Matt let the quiet linger for another block before he spoke again. “I watched some of it from the CCTV room,” he said casually. “It was hard to watch at times. You dropped more glass than any new start I can remember.”

The blonde huffed and pouted. “You need to find me a new job,” he demanded, the squeaky voice turning the order into something almost pleading. “Or at least put me on the main floor. Those uniforms don’t look half as bad.”

The driver shook his head slowly. “It’s too late for that,” he answered. “One of the high rollers has already taken a real liking to Jessica. And the general manager knows which department you’re in now. Reassigning you would raise too many questions.”

James’s eyes widened as bile simmered in the pit of his stomach. “Clifford saw me?” he squeaked, fists clenching harder. That was the same bastard who framed him in the first place. “You’re telling me Clifford fucking Moss watched me prance around like this?”

Matt nodded, the grin never leaving his face. “Well, he does run the place after all. But your makeover may have worked a little too well,” he said comically. “He seems interested in you. And Kevin West practically claimed you for the rest of the night. You’re stuck on the VIP floor, sweetheart.”

The feminized man opened his mouth, then closed it again, the words tangling behind those swollen lips. He stared at Matt in open horror. “I can’t go back there,” he finally managed, his high voice trembling. “I’m terrible at this. You saw what happened.

Matt’s expression turned serious for the first time all night. “Exactly, you are really bad at it,” he said. “Which is why we’re going to need to take more drastic measures if this plan is going to work.”

The car rolled to a stop at a red light. James sat frozen, the air conditioning cool against his bare skin as the weight of Matt’s words settled in the silence.

He turned slowly, his blue eyes wide, glossy lips parted in a perfect O of dread. “What do you mean by drastic measures?” he whispered.

Matt only smiled and pressed the accelerator as the light turned green, leaving James gasping in silence. He had no idea what was in his former employee’s mind, but he was sure he wouldn’t like it.

“No, no, absolutely not!” James repeated the words tumbling out in that high, breathy soprano that still sounded like a stranger every time he opened his mouth. He paced the living room in quick, agitated steps, the hem of the pink negligee fluttering around his thighs with every turn. The satin clung to the glued curves of his chest and hips, the thin straps doing nothing to hide how the fabric brushed his breast forms whenever he moved. He was pleased to be out of the disgracefully slutty uniform, but the night gown was the only piece of sleepwear Matt had placed in his closet, and it wasn’t much better. His bare feet stomped against the hardwood of the living room as he paced.

Matt sat relaxed on the couch, one ankle crossed over the opposite knee, his coffee mug balancing on his thigh. He watched the pacing with the calm amusement of a man who already knew how this conversation would end. James was backed into a corner, after all.

The transformed blonde spun towards the man, his arms crossed tight beneath his breasts. “I’m not letting some faggot get inside my head. You can forget about it!”

Matt raised an eyebrow at the feminized man’s homophobic remark before setting his cup down with deliberate care. He leaned forward with his elbows resting on his knees. “If you’re going to survive day two on that floor, you’re going to need a little extra help. We agreed on this,” he said calmly.

James stopped mid-step. “Agreed? We had no agreement. Look at me!” he squealed in a childish tone. “I’ve had no part in this.”

Matt shrugged, unconcerned. “You decided to walk into my house instead of turning yourself in. I told you that I’d help you, but on my terms, and you agreed.” He leaned back again, stretching his arms along the back of the couch. “Now, let’s get serious. Dixon did a great job on your makeover, maybe too good a job. His husband, Paul, is one of the best hypnotherapists in the state. He has a talent for stifling unwanted behaviors and bringing out desired outcomes. That’s exactly what we need.”

The blonde shuddered. “No way! I can do this without some sissy trying to hypnotize me.”

Matt grinned at the ironic choice of words. “Mhmm,” he said with amusement. “But let’s get real. We don’t have the time for you to learn how to play the part, unless you want to be stuck as Jessica for months.”

James parted his plump lips to speak, the retort already forming on his tongue. However, the doorbell suddenly rang, cutting off his complaint.

Matt rose without a word and walked to the entrance, leaving James frozen mid-breath. The door opened, and the handsome Paul Bishop stepped inside, tall and composed, dark-blonde hair neatly trimmed, blue eyes calm behind a polite smile. He wore a pale gray button-up shirt tucked into dark gray slacks, his sleeves rolled once to reveal an extravagant Rolex watch. A small black case swung from one hand.

Paul’s gaze found James immediately and softened with an appreciative warmth. He crossed the room in a few unhurried steps and extended his free hand.

“You must be the infamous Jessica,” he chuckled. “Matt says you need some help adjusting to the new you.”

James stared at the offered hand, his manicured fingers trembling as he accepted it. The blonde mouth was agape in shock. Did this bastard think he was some sissy or trans? What had Matt told them?

Paul’s smile never wavered as he placed the case on the coffee table before turning back to the feminized blonde. “Now,” he said happily. “Shall we begin?”

End of Chapter Two

x4

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