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Jamie has great Attributes
🕑 Added 2025-10-06 14:06:55 +0000 UTCA NSFW Feminization Story - enjoy
Jamie Has Great Attributes
Everyone on the office floor looks around and towards the manager's door.
“Jamie, Clark,” the manager, Mr. Sterling, calls out. “Can I see you in my office, please?”
Jamie, sitting in his cubicle, looks over the partition wall to see Mr. Sterling standing in his doorway with a stern expression. He glups, hoping he’s not in trouble.
“C-Coming, sir!” Jamie replies, awkwardly standing, getting trapped between the chair he’s sitting in and the desk.
Catching himself on the desk, he stands up arrow straight and brushes the long hair from his eyes. Clearing his throat, he tentatively steps out of his cubicle to make his way around to his boss's office.
“Psst, Jamie….” Karen, his co-worker, whispers as he passes her booth. “If you’re in trouble with the bigwigs, flutter those big blue eyes and present that big ass of yours. Trust me, those dirty pervs love it.”
Jamie stops and glares at Karen for a second. “Stop saying I look like a girl, Karen.” He grumbles. “You know I’m sensitive about how fat my ass is. I told you last week that people used to bully me.”
Karen rolls her eyes and lifts her hands in defeat. “I was only playing, dude. They ain’t going to fire you. I overheard Mr Sterling and the big boss man talking about how much ‘potential’ you have the other day.”
“S-Seriouly….!?” Jamie leans on her cubicle wall with real interest. “W-What else did they say!?”
Karen leans back in her chair and bites the end of her pen with a smug grin.
“You'd best hurry, pretty boy. You don’t wanna keep Mr. Sterling waiting now, do you?”
Jamie’s face drops as Karen begins to chuckle to herself. He flips her off in a playful manner before letting out a sigh.
“We still going for noodles after work?”
“You betcha.” Karen turns back to her PC and waves him off with one hand. “Don’t get fired, okay. You’re the only person I like here.”
With a tut and some dramatic flair, Jaime resumes his walk back to Mr. Sterling's office. “Why am I still sporting this hairstyle?” He grumbles quietly to himself. “I haven’t been surfing for so many years….”
He looks down at himself and then tries to peek a look at his own backside. “Why do I keep wearing the tightest trousers. Urgh….” He complains as it wiggles and jiggles.
Reaching Mr. Sterling's office, he knocks once. “S-Sir….?”
“Mr. Clark….” Mr. Sterling calls out from within. “Come in, young man.”
Jaime pushes open the doors to Mr. Sterling's office and steps inside. It’s a corner office with actual windows that overlook the city park. It’s a huge difference from his sterile cube and the fluorescent lights that he jokes are making his skin transparent.
“Y-You wanted to see me, sir?”
“Yes, yes….” Mr. Sterling looks up from his laptop screen and smiles. “Sit, young man. Please, sit.”
Jamie looks around as he approaches the chair in front of Mr. Sterling's desk. The rich mahogany wood adorning the shelves makes him almost gasp in wonder. As he sits, Jamie daydreams, imagining himself in a plush corner office, calling workers into his office.
“I know I say this every time I come in here, sir,” Jamie says, looking out at the blue sky through the large office windows. “But your office is so nice. I gotta get me one of these corner offices!”
Mr Sterling looks back in the direction that Jamie is staring. He lets out a small laugh before leaning on his desk towards the young man sitting opposite.
“So, I assume that means you want to move up in the company, yes?” Mr. Sterling asks, waiting keenly for a reply.
“Yes,” Jamie nods. “Yes, very much so, Sir. I’ve been working really hard recently.”
“Good,” Mr. Sterling's smile widens. “You’ve been… noticed. I’ve got a real peach of an opportunity for you this weekend. I think it would be a huge step in the right direction for you, in particular.
“M-Me, sir….?” Jamie asks, almost lost for words
“Please, young man,” Mr. Sterling grins. “Call me Nigel.” Nigel then looks at the papers on his desk and clears his throat. “Did you know it’s the major conference this weekend? All the major players in our sector get together to network, etc…”
“Yes, Sir—Nigel. I’m aware.”
“Good,” Nigel casually throws a folder across his large desk in Jamie’s direction. “Here are your tickets, passes, and conference documents.”
“S-sir….?”
“I assume you are able to make it, Mr. Clark?”
“I-I….I don’t understand.”
“What is there to understand, young man?” Nigel leans back in his chair with a confident smile. “Every year, Mr. Miller, our CEO, takes an….an employee with great…umm….attributes with him each year.”
Jamie points at himself in disbelief.
Nigel nods and smiles. “Yes, you’ve been chosen. What a wonderful opportunity for you. A weekend away with the CEO. I assume you’re able to… attend?”
“Y-Yes… of course!” Jamie doesn’t know what to do with himself, so he fidgets in his seat. “B-But are you sure they want me? This isn’t some mistake or a joke?”
Nigel looks down at his paperwork. “No, says here. Jaime.”
“My goodness, Sir. I’ll do my best to make sure I don’t let anyone down!” Jamie grabs the file on the desk and clutches it close to his chest. “T-Thank you, Sir! This is wonderful!”
“Good,” Nigel then looks at his door. “That’s all, young man. Back to work.”
Jaime thanks Nigel again as he stumbles out of the office in excitement, clutching the folder tightly against his chest. Nigel calls after him with a calm smile, wishing him luck for the weekend.
Jamie walks quickly back toward his cubicle, his head buzzing with disbelief. Karen swivels in her chair the moment she spots him, eyebrows arched in curiosity.
“Well?” she asks, tilting her head.
Jamie leans against her partition wall, unable to hide the grin spreading across his face. “I’m going to the conference,” he blurts out, his voice a mix of nerves and pride.
“Kiss ass….” Karen grumbles to herself and then turns back to talk to her computer screen. “That won’t be the only thing you’re kissing….I’m sure.”
“W-What was that?” Jamie asks, looking through the paperwork in his hands. “I…erm…” he smiles wide when he sees a plane ticket. “I wasn’t listening,” he finishes, looking up at Karen with a smile.
“Nothing, dude…” Karen grumbles, slouching at her desk. “Have a good time and don’t forget about me, okay…..”
Still not listening, Jamie speaks as he reads the manifesto. “I won’t be able to go for noodles tonight, Karen.”
“It’s fine,” Karen huffs. “It’s not like I fancy you or anything….”
Jamie’s heart is still racing when he finishes the last of his packing that Friday night, and by the next morning, he’s sitting on a plane bound for the city where the conference is held. The flight is long, and the recycled air and cramped seats make him feel wrung out, but the folder of conference documents never leaves his lap.
The cab ride from the airport feels surreal, the skyline glittering like something out of a movie. When the car finally pulls up to the towering glass hotel, Jamie stares in awe at the massive revolving doors and the suited staff waiting just outside. Tugging his bag along, he steps into the marble lobby, where a giant chandelier sparkles overhead.
He approaches the reception desk, still adjusting his wrinkled shirt, and gives his name. The receptionist types something into the computer before pausing, then looking up at him with a polite smile.
“Ah, yes, Mr. Clark,” she says smoothly. “You do have a room booked for the weekend. However, Mr. Miller has requested that you meet him first in his presidential suite.”
Jamie’s breath hitches. “H-He does?”
“Yes, sir,” the receptionist confirms, sliding a small card toward him with a room number written neatly across it. “He’s expecting you now.”
Clutching his bag a little tighter, Jamie nods quickly. “R-Right. Of course. Thank you.”
He makes his way through the hushed hallways, the carpet thick under his shoes, his stomach tying itself in knots. By the time he reaches the door with the gleaming brass numbers, his palms are damp. He takes a steadying breath, lifts his hand, and knocks.
Almost at once, a deep voice calls from within. “Come in.”
Jamie swallows hard, pushes the door open, and steps inside.
The room is beyond swanky, and the large French doors at the back of the living space open out onto a balcony that overlooks the crystal-clear waters. Sitting on one of the regal-looking sofas is Mr. Miller. He’s looking out of the large windows at the blue skies with a coffee in hand.
“M-Morning, Sir…” Jamie stands beside the sofa, all but saluting the large, rounded older gentleman who is the CEO of the company he works for.”
“I like them sunnyside up,” Mr. Miller grunts, clicking his fingers. “And a fincical times, bell boy. Now, mush.”
Jamie rubs his neck with anxiety. “Erm… N-no, Sir. I’m from the company. I-I…I don’t work at the hotel. I’ve been asked by Mr. Sterling to attend the conference with you…”
Mr. Miller’s face slowly turns to look in disgust at Jamie, who stands before him.
“I-It’s an honor to be here….S-Sir. I will do my best! Thank you for having me!” Jamie continues, his heart now thudding wildly in his chest
Mr Miller looks unimpressed. He looks Jamie up and down, frowning with displeasure. “You’re going to my assistant this weekend?” he asks rudely.
“Y-Yeah…?” Jamie grits his teeth.
“You’re not a woman,” Mr Miller observes, drinking his coffee. “Is your name Ms. Jamie Lescott?” Nigel places his coffee down onto the glass coffee table in front of him and crosses his legs.
“That’s who’s supposed to be attending this conference with me. The Jamie from the 3rd floor with the big tits….”
“M-My name’s Jaime, but I’m not Jamie Lescott,” Jamie explains, throwing his head back in frustration. “I knew it. I knew this was some big mistake.”
Mr Miller stomps the arm of the chair he’s sitting in. “Fuck sake,” he growls, hitting the arm again. “They’ve sent the wrong fucking Jamie. This just won’t do.”
“I’m really sorry, Sir,” Jamie hands his head in shame. “I-I…I think it might be too late to correct this mistake, Sir, but I shall do my best to assist you.”
Mr. Miller lets out a long, exasperated breath. “Ah, it’s not that, young man. I’m sure you’re just as capable, it’s just…” Mr Miller clears his throat. “It’s just…. My fellow CEOs and I enjoy a bit of friendly competition at these events to liven them up. Every year, we try out do each other by bringing to sexiest assistant we can….”
“S-Sir…..?”
“I know it’s rather sexist of us, but it’s all good-natured fun. See, that’s why I needed Ms. Jamie Lescott here because she’s got a fat ass, massive tits, and a cracking pair of legs.” Mr Miller points at Jamie. “You don’t have—”
Mr Miller stops mid-sentence and just stares in Jamie’s direction. It’s an incredibly awkward moment, and Jamie forces a smile. He does all he can to stand up straight and look presentable, although, in his mind, he knows he’s not what Mr. Miller truly wants.
“S-sir….?”
Mr. Miller takes a long sip of his coffee, checking out every inch of Jamie’s body, as if he’s a prime turkey being readied for slaughter.
“Boy,” Mr Miller says abruptly. “You’ve got very girly hair and a fat ass for a man.”
Jamie blushes. “T-Thank you,” he replies through gritted teeth.
Mr. Miller stands, and his height, weight, and sheer presence make Jamie step back slightly. Jamie’s just over five foot seven, but Mr Miller must stand at least six foot four. Jamie can’t help but think it’s no wonder this man is the CEO. It’s always taller men.
“I’ve got an idea on how we can save this situation, Jamie, the assistant who isn’t a woman.” Mr Miller says in a commanding tone, clicking his fingers as he walks into another room of the hotel suite.”Wait here.”
Jamie stands stiffly as he mumbles under his breath. “Of course, this would happen to me. Wrong Jamie. Karen’s never gonna let me live this down.”
He rubs his temples and glances at the door through which Mr. Miller disappeared, fighting the urge to just walk out of the hotel altogether rather than continue living through this embarrassment.
After a long stretch of silence, the door opens again and heavy footsteps cross the plush carpet. Mr. Miller strides back into the room, a wide smile on his face now, his earlier irritation replaced with something far more deliberate.
“Jamie,” he says smoothly, his voice carrying authority. “Let’s do this properly. Please, call me David when we are in private.” He settles back into the armchair and studies Jamie with sharp eyes. “I’ve been thinking, and I’ve sorted this silly little situation we find ourselves in…”
Jamie grips his bag tighter and leans forward. “S-Sir?”
David nods, his smile curling into something pointed. “Yes. You can stay, agree to my ingenious solution. Or you can leave now and head home.” He tilts his head, his gaze firm. “But I’ll warn you, walking away would be very disappointing to me. And the company doesn’t tend to keep people who disappoint.”
Jamie’s eyes light up, and he speaks without thinking. “Y-Yes, Sir—David. Whatever it is…. I’m happy to do it for you and the company!”
“Wonderful,” David claps a hand on his knee in delight. “Good, well then. I want you to present as a woman for the weekend. You’ll dress, act, and BE a woman for the entire conference, and that’ll give us a shot at winning the…umm… little bet I have.”
Jamie’s mouth falls open, and his thudding heart beat fills his ears. “S-Sir….?”
“Did I mumble?” David grows agitated before passing a small handwritten note. “Well, lucky for us, we’ve only got meet and greets this morning. I don’t need your assistance with that, so that gives you ample time to head to that address.”
Jamie takes the note and looks at the address. It’s for a salon nearby.
“Mrs. Sandra at the salon will help you with the makeover,” David sips again at his coffee, hiding a smile. “When you’ve become a pretty woman, head to the clothing shop a few doors down, get suited and booted….”
David chuckles to himself. “Well, not so much boots, more high heels… You understand.” David smiles as he amuses himself, before turning more serious as he looks at the surprised and shock on Jamie’s face.
“You seem unimpressed?” David asks sternly, leaning forward in his chair to assert dominance. “I suggest you wipe that frown off your face and smile. Young ladies always look nicer when they smile.
“B-But….a woman? Dress as a woman?”
“Yes.” David nods once and then tilts his head. “Or are you trying to disappoint me and the company?"
Jamie instantly shakes his head. “N-No… Sir. I’d never do that.
“Well then!” David stands, smacking Jamie on the arm in celebration. “I can’t wait to see your transformation, Jamie. I’m sure you’ll represent our company as a fine young lady….” David’s smile turns to a glare. “Won’t you….young lady.”
Jamie nods only once. “Y-Yes… sir.”
“Good.” David looks him up and down for the last time and then shuffles off. “Now, get going. I’ll see you for the first conference.”
Jamie nods before being spooked by David, who clicks for him to leave. Awkwardly gathering his things, he quickly leaves. Knowing the first conference starts at ten thirty sharp, it only leaves Jamie a few hours to get transformed.
Ruishing, Jamie throws his luggage into his room and, with the address clutched tight in his hand, he rushes out of the hotel and in the salon's direction. Only a block away from the hotel, the rather posh-looking salon looks intimidating.
Not somewhere Jamie would ever frequent.
Bashfully stepping inside, Jamie keeps his head low as the noise of hair blowers and chattering women drowns out his father's nervous footsteps. He approaches the reception desk and awkwardly smiles at the young lady behind the counter.
"I-I….I’m here to see a Mrs Sandra….” Jamie says, his voice barely audible over the sound of the busy salon.
The receptionist guides Jamie past the rows of chairs and gossiping women until they reach a frosted glass door at the back of the salon. She opens it with a knowing smile and ushers him inside.
The private room smells faintly of hairspray and roses. At the center stands a tall woman with sharp cheekbones and a cascade of perfectly styled silver hair. She folds her arms as Jamie steps timidly inside.
“You must be Jamie,” she says with a voice like velvet, her eyes sweeping over him in one slow, deliberate motion. “Please, call me Alice. It’s nice to meet you.”
Jamie blinks. “L-Likewise….”
She steps closer, circling him like a cat inspecting prey. “Though in all my years of working with Mr. Miller, this is the first time he’s ever sent me a man and not some busty young blonde.”
Jamie shifts uncomfortably, tugging at the hem of his shirt. “I-It was a mistake… I wasn’t supposed to be the Jamie he wanted. But… he said I have to, uh, present as a woman for the weekend.”
Alice lets out a soft, low laugh, one that is knowing. She tilts his chin up with a manicured finger, forcing him to meet her sharp gaze. “Oh, I see. A complete feminization, then. How delicious.”
Jamie’s cheeks burn red. “C-Complete…?”
Alice walks to a cabinet and pulls out a tray of brushes, powders, and gleaming scissors. He moves fast, as if this is a normal occurrence for her.
“Relax, sweet boy. Mr. Miller sends his girls here all the time for a touch-up before the conference. A manicure, a new blowout, maybe a fresh shade of lipstick.” She sets the tray down with a clink and turns back to him, her eyes glinting. “But you… Oh, you’re special. You’re a blank canvas.”
Jamie swallows hard, watching her move elegantly around the space. “I don’t know if I can…”
“You can,” Alice interrupts, her smirk widening. “And you will. By the time I’m finished with you, no one will ever believe you weren’t one of Mr. Miller’s pretty little assistants from the start.”
She pats the tall salon chair with one hand. “Sit. Let’s make a woman of you.”
Alice stands behind him, her fingers combing through his long hair with expert precision. “Yes… This will be fun. Very fun.”
Jamie is then instructed to strip down to his birthday suit. He does so after so protest. To hide his modesty, Alice gives him a small towel to cover himself. After the initial awkwardness, Alice starts attaching body forms, checking for fit and skin tone.
“So, young man,” Alice talks ideally, fitting him with some rather realistic-looking breasts. “How is it that this year, Mr. Miller has brought a man?”
Wincing as Alice smooths a strange adhesive paste across his chest, Jamie tries to make sense of it all. “I… guess it was a mistake?” he mutters, flinching again when the heavy breast forms are pressed firmly against his skin, Alice leaning on him to secure them in place. “The Jamie that I’ve been mixed up with also has blonde hair.”
Alice steps back and slowly lets go, her hands slipping away as the forms settle heavily against Jamie’s chest. They hang there with surprising weight, the edges blending almost seamlessly into his skin as though they’ve always belonged.
“How do they feel?”
Jamie looks down with interest, having never seen breasts from that point of view.
“Errr….” he cups one and feels its heft. “How is it supposed to feel. I-I…I’ve never done anything like this before.
“Are they pulling on your skin?”
Jamie doesn’t answer. His eyes are fixed downward, wide with disbelief at the full breasts now adorning his chest. They lift and fall in time with each anxious breath, and the nipples jut so prominently they look as if they could cut glass.
Stifling a laugh, Alice struts over to a nearby chair and snatches at a lacy red bra. Before Jamie can say a word, she lifts his arms, threads them inside the bra, and fastens it tight around his back.
Stepping to the front, she guides each breast into its cup and looks up at Jamie with a smile.
“Are they pinching at the skin now you’ve got a bra on?”
Jamie lifts his gaze to Alice, innocence written across his face. For a moment, he looks less like a grown man and more like a bewildered teenager, standing awkwardly as though learning womanhood at the side of a patient mother.
“N-No pinching.”
Alice gives one tit a squeeze. “Good.” She scurries over and gathers something from a nearby table. She then walks slowly toward Jamie with a cheeky smile on her face.
“Young man…” she kneels in front of him and looks up. “No getting excited now. I want to put this on you with no drama. Do you understand?”
Not even a second to answer, Jamie jumps in fright at the cold hands that have found their way up his modesty towel and are jiggling with his balls. He bites at his bottom lip to try and control himself as the rather dashing, but older lady, fondles his cock.
“Errr….Um…..Ma’am….?”
“Nearly done.”
“N-No…. please s-stop….”
Click
“Ma’am…” Jamie thinks about pushing Alice away from down there, but before he knows it, Alice is standing once again.
She’s got a rather childish-looking grin on her face.
“Jamie….” She winks and blushes. “It’s all about the motion of the ocean, huh?”
Jamie frowns hard and glares as she walks away and gathers the matching red lacey panties to go with his new bra.
“What’s that supposed to mean, and what have you done to me down there? Why does it feel like you’ve attached something to my—”
“Mr. Miller was very clear,” Alice struts over, the panties dangling from her fingertips as she shows them off. “You were to be caged to ensure maximum compliance.”
Jamie looks down and tries to see what’s been put on his little gentleman, but he can’t see over the breasts hanging from his chest. He tries to flatten them down to see, but he just can’t. He becomes frustrated.
“A cage!?” he groans, reaching down to feel it instead.
“Ah, don’t be so upset about it,” Alice replies, kneeling down again to help him into the red panties. “The cage will stop you from having a wardrobe malfunction. The last thing you wanna get is a stiffy in front of a bunch of stuffy old blokes.”
Alice glides the panties up his legs, making sure the panties cradle his newly attached cage and that the material around the back nestles nicely between his plump ass cheeks.
“How's that feel?”
“Like I’ve got a cage on my cock….”
Alice rises gracefully, her fingers brushing Jamie’s chin in a teasing touch. “I’ll give Mr. Miller the key to the cage, alright?” she says with a sly smile. As she turns back to her table, she throws him a playful wink, leaving Jamie frozen in place.
A hush settles as Alice studies the array of tools on her table. When she turns back to Jamie, her playful smile is gone, replaced by a cool, professional stare. One finger rests thoughtfully against her cheek as the sharp click of her heels fills the room. She circles him slowly.
“Jamie….” She says politely. “Do you shave your body?”
He looks around at her as she comes into view from behind. “No…why?”
“You’re virtually hairless,” Alice comments as she stops just behind him and looks intently at his backside. “You also have a really plump backside for a man.”
Jamie sighs. “I know. Don’t remind me.”
“In this case…” Alice leans into Jamie’s view from behind, her smile curling with amusement. “It works for us. I was considering adding forms to your hips and backside, but it seems we won’t need them after all. And since you’re already smooth and hairless, we can skip ahead to the makeup.”
Alice claps her hands together lightly, her professional mask slipping back into something playful again. “Alright, sweetheart. Let’s bring that face to life.”
Jamie fidgets where he stands, tugging at the straps of the bra as Alice wheels over a tall vanity chair. She pats the seat expectantly.
With a sigh, Jamie lowers himself into it, the lace digging against his skin as he sits. Alice tilts his chin upward with two fingers and hums approvingly. “Good bone structure. This will be fun.”
She starts with eyeliner, pulling his lids taut as she sweeps the pencil with a steady hand. Jamie winces at the unfamiliar sensation, his lashes twitching, but Alice hushes him with a gentle shush. “Don’t fight it.”
Dark, smoky eyeshadow follows, brushed across his lids in confident strokes that make his wide blue eyes pop even more. Then comes the mascara, lengthening every lash until they fan dramatically.
Jamie blinks at the mirror in disbelief. “I… I look—”
“Stunning already,” Alice cuts in, plucking a tube of lipstick from her collection. “Now hold still. No pouting unless I tell you to.”
The deep red spreads across his lips, glossy and perfect. Alice leans back, tilting her head as though studying a painting. “Mmm. You’ll break hearts before the day is over.”
Jamie’s cheeks flush, though whether from embarrassment or the blush she dusts across them, even he isn’t sure.
Alice’s gaze drifts up to his hair. She circles him once more, lips pursed. “This surfer boy mess won’t do.”
Jamie stiffens. “Wait! What? No, the hair is fine, really, I—”
Before he can finish, Alice is already snapping her fingers. A young assistant appears from behind a partition, arms laden with hair extensions and styling tools.
“Extensions,” Alice says simply. “Long, soft, and curled. He’s got the face now, he needs the frame.”
Jamie protests weakly as the assistant begins clipping the glossy strands into place, but Alice only smirks, arms crossed as she watches. “Don’t wriggle. Unless you want them glued in crooked.”
An hour slips by. The smell of hairspray lingers in the air as the final curls fall into place, framing Jamie’s face in soft waves. The extensions blend seamlessly with his natural hair, giving him a lush, feminine look that makes his own reflection feel like that of a stranger.
Alice finally steps forward, heels clicking against the polished floor. She runs a hand gently over one curl, tucks it behind his ear, then steps back to admire him fully.
Jamie rises awkwardly from the chair, standing in nothing but the lace bra and panties, his new hair cascading in soft curls around his shoulders, his face transformed into something striking and undeniably pretty.
Alice’s smile widens. She crosses her arms, taking in the sight like a painter finishing a masterpiece.
“Well,” she murmurs, eyes glittering. “There’s the Jamie Mr. Miller was expecting. Now, shall we get you dressed for the conference and back to work?”
Alice turns, grabs some high heels, and then holds them up with a cheeky smile.
“Ever worn these things to work before, Jamie?”
Blushing like crazy, Jamie just shakes his head.
“Ah, well…. once you’re dressed, I’ll give you some tips on how to look effortlessly feminine.”
“T-Thank you?”
“You’re welcome, young lady!” Alice winks. “Now, let’s get you dressed. I know I’ve got a suitable mini skirt around here somewhere.”
Alice rifles through her racks with a hum before plucking out a sharp, little office mini-skirt. “This one,” she says, holding it against Jamie’s hips. “Mr. Miller wouldn’t want you wearing anything longer.”
Jamie blushes as she guides the skirt up his legs, tugging it into place until it hugs his hips and backside. The snug fit makes him wriggle.
“Stop squirming,” Alice chides with a smirk. “You’ll get used to it.”
Next comes a white, fitted blouse. Alice slips it over his arms, buttoning it up slowly so it molds around the curve of his new breasts. Jamie looks down, mortified at how the fabric strains in all the right places.
“Now the jacket,” Alice continues, slipping him into a sleek black suit jacket that pinches in at the waist, exaggerating his curves. She smooths the fabric against him with proud little pats. “Delicious.”
Jamie swallows hard, glancing at himself in the mirror. The man he was is vanishing fast.
Alice lowers herself gracefully, a roll of sheer pantyhose in her hands. “Feet first,” she instructs.
She gathers the fabric and guides it over Jamie’s toes, then slowly works it up along his calves and thighs. The nylon clings snugly to his skin, smoothing every curve until his legs effortlessly feminize.
Once satisfied, she rises and retrieves the final touch: a pair of tall, glossy black heels. Holding them up with a mischievous smile, she says, “Now let’s see if you can handle these.”
Jamie groans, but slips his feet into the shoes. Alice helps fasten the straps, then steps back, grinning at her handiwork.
He pushes up from the chair, but the moment he takes a step, his ankle wobbles and he nearly topples forward. He grabs Alice’s arm in panic.
“Careful, darling.” She steadies him with a laugh. “We can’t have you breaking an ankle.”
Jamie steadies himself and looks into the mirror. The girl staring back at him is unrecognizable. With her flushed cheeks, glossy lips, curls, breasts filling her blouse, skirt hugging her hips, and smooth legs
“Th-This is crazy….”
“Maybe….” Alice smiles as she clasps her hands together. “But kinda perfect for you. Now, anyway. Time for a crash course in being a lady….”
She moves behind him, gently tugging his shoulders back. “Posture. Stand tall, tits out. You want those nipples pointing at people, not the floor.”
Jamie obeys, stiff and awkward.
“Better,” Alice says, circling him. “Now, let’s try walking. Heels first, then toe. Small steps, hips relaxed. Like this.” She demonstrates a strut across the room, her hips swaying effortlessly.
Jamie tries, nearly stumbling again. Alice steadies him with a firm grip on his waist. “Not like a soldier. Like a woman. Let your body… flow.”
He takes another pass, his movements stilted but improving.
“Now,” Alice says with a glint in her eye, “bending forward.” She places him before the mirror, presses lightly at the small of his back, and makes him lean down. The blouse gapes open at his chest, the swell of cleavage spilling into view.
Jamie gasps as he watches his reflection. “T-This is wrong…”
Alice smirks. “It’s effective. Old men love to think they’re seeing something they shouldn’t. You give them just enough to keep them hooked.”
Jamie groans, covering his face, but Alice isn’t done. She tilts his chin up with a finger. “And last lesson to help you in the world of men. When one of them makes some crude joke, you don’t roll your eyes, you don’t scowl. You giggle. Light, airy, playful. Try.”
Jamie hesitates, then lets out a pitiful little laugh. Alice bursts out laughing, shaking her head in disbelief. “No, no. Not like you’re choking. Like this.” She demonstrates a soft, practiced giggle that sounds effortless.
Jamie tries again, softer this time, higher-pitched. It sounds shockingly natural.
Alice’s eyes glitter. “Perfect. With a little more practice, they’ll eat from your palm.”
Jamie stares at the reflection in the mirror, horrified. “D-Do I want them eating from my hand?”
Alice steps up beside him, her hand smoothing over his curled hair, her lips brushing his ear. “Oh, darling,” she whispers, “You’ll soon understand, but this is as far as my help goes. You are ready.
Nervous Jamie looks again at the mirror and the stunning blonde woman glaring back. “Are you sure I’m ready!?”
“Indeed,” Alice pats his backside. “I’ve sent spare clothing to your hotel room. Now, you'd best hurry before the first meeting takes place. You’ll be needed at Mr. Miller’s side.”
Jamie nods.
“T-Thank you, Ma’am…” he gestures at himself “F-For all this.”
“You’re welcome, sweetheart,” Alice tilts her head to one side. “Just remember, you’re a lady. Do your best to act like one at all times. Soft, delicate, elegant, beautiful, and most of all, strong.”
Jamie nods again. “Yes, Ma’ma. Thank you, Ma’am.”
“Go on, sexy…” Alice waves him away with a hand. “Fingers crossed this gets you a promotion, huh?”
Jamie smiles, nods a third time, and turns to slowly and carefully walk away in his heels. As she does, Alice smiles softly at her creation and speaks under her breath.
“Good luck with the after conference, young man.”
Jamie steps out of the shop and carefully walks back towards the hotel. His heart thudding in his chest as every step is an adventure. Eventually, he reaches the hotel with a long sigh of relief.
Stepping inside, his heels click sharply against the marble as he traverses the lobby. Every movement still feels foreign, awkward, and a little humiliating, but with each careful stride, he begins to find a rhythm.
By the time he reaches the elevator, the sway of his hips feels more natural, and he catches himself adjusting his posture automatically, with his shoulders back and chest lifted.
Inside the elevator, he practices tiny steps, heels first, letting the nylon of his pantyhose stretch and cling smoothly around his legs. By the time the doors open onto the conference floor, Jamie is still nervous, but he carries himself with a newfound confidence. He adjusts his skirt and smooths the jacket at his waist, straightens his hair, and takes a deep breath.
The moment he steps into the conference room, heads turn. Jamie’s face flushes, a mix of fear and embarrassment, as men in suits glance curiously at the striking woman who has just appeared. He fidgets slightly, letting his eyes search the room until they land on Mr. Miller.
Mr. Miller sits at the head of the room, clipboard in hand, and his eyes narrow. Jamie shuffles his way over to him.
“Miss?” Mr Miller looks up at Jamie, a touch confused.
Jamie straightens, tilts his chin up, and forces himself to smile. “Mr. Miller… It’s me, Jamie,” he says, voice softer, lighter than usual. “Remember, you asked me to….” Jamie leans slightly forward, exposing his chest a little. “You asked me to get a makeover, remember?”
Recognition flickers across Miller’s face, then his expression changes to delight.
“Ah! Of course!” he exclaims. He stands and gestures for Jamie to come closer. “Gentleman. This is my assistant, Jamie. She sends her apologies about not attending the meet and greet.” Mr. Miller chuckles to himself as she slaps Jamie’s ass. “You know what women are like. She had to get her hair done before meeting everyone!
The room erupts in polite applause, with men nodding and some offering warm smiles. Jamie’s cheeks burn as he steps forward, smooths the skirt over his hips, and offers a timid but professional smile.
Everyone then settles down as the meeting starts. Mr. Miller reaches for Jamie to whisper in his ear. “Good work. You look fantastic in that get-up. Now, don’t let up. Keep acting like a little tease to these guys and you’ll be in my good books.”
“Y-Yes, sir,” Jamie whispers back, noticing how some of the men are still looking.
Jamie then takes a deep breath and slides into his chair at the conference table, behind Mr Miller.
He forces himself to cross his legs gracefully, the cage making it slightly uncomfortable, but far preferable to giving anyone a direct view up his skirt. His hands settle on the notepad before him, pen poised. He’s ready.
The day continues as Jamie expected. He passes out notepads, fetches coffee, and takes meticulous notes as Mr. Miller discusses strategies with other executives. It’s all rather normal, except for the high heels and constant lust-filled stares.
At lunch, the conference room buzzes with polite chatter. Jamie hovers nearby, carefully observing each conversation, offering smiles and nods where appropriate, and laughing politely at Mr. Miller’s jokes.
Across the room, Mr. Patel, a rival CEO, arrives with his assistant, a young woman in a sharply tailored suit. The two men exchange greetings, each subtly assessing the other’s companion.
“David!” Mr. Patel pats his shoulder. “And who is your lovely young lady here?”
Mr. Miller puts his arm around Jamie’s side and thrusts him forward, like prime cattle ready for sale.
“This is Jamie. She’s a real go-getter, aren’t you, sweetheart!” Mr. Miller playfully pats Jamie’s ass.
Jamie giggles, just like Alice taught him, before reaching across to shake Mr. Patel’s hand.
“I hear you’ve got some wonderful….attributes, young lady….” Mr Patel smirks, looking over Jamie’s shoulder at Mr. Miller behind.
“T-Thank you, sir,” Jamie replies, quickly stepping back behind Mr. Miller.
“Polite too,” Mr. Patel then pulls his assistant forward. “This is Sarah. She also has some….very nice attributes.”
Mr. Miller greets the young lady, before reaching behind to give her ass a quick squeeze.
“Ha, yes, Rohan!” Mr. Miller squeezes Mr. Patel’s assistant ass a second time. “Very nice attributes, young lady…”
“Can I…?” Mr. Patel gestures towards Jamie with a smirk tugging at his lips.
“Yes,” Mr. Miller nods at Mr. Patel. “Please, Rohan. She’s very firm.”
Mr. Patel clutches at Jamie’s ass, making him jump a little, much to Mr. Patel's amusement.
“Seems she doesn’t like to be shared, David!”
“Indeed, but please don’t be offended,” Mr. Miller laughs, bringing his arm around Jamie’s sides. “She’s just a company girl, that’s all.”
As the two men laugh and talk, Sarah, Mr. Patel’s assistant, leans over to Jamie to whisper.
“Dirty old gits, huh?”
Jamie looks at her frustrated smile.
“Y-Yeah…” he fidgets awkwardly as his cage suddenly feels so much smaller from all the attention.
“All this for a promotion, huh?” Sarah continues to whisper.
“Y-Yeah….” Jamie nods. “For a promotion…”
By the end of lunch, Jamie’s confidence increases. He anticipates Mr. Miller’s requests before they are spoken, presents materials neatly, and subtly notes the moods of other executives. Mr. Miller gives him quiet nods of approval each time, clearly impressed.
When the conference wraps up, Jamie exhales in relief, his body tired from standing on his heels and constantly being aware of his posture and gestures. To his surprise, Mr. Miller signals for him to follow.
“Jamie, excellent work today,” Mr. Miller says as they walk toward the elevator. “I want to review a few points in detail in my hotel suite. I trust you can handle a bit more responsibility tonight.”
Jamie nods, pulse quickening with pride and anticipation. “Of course, Sir. Yes, Sir,” he says, straightening his skirt, smoothing his jacket, and adjusting a curl of hair. A small smile creeps onto his face.
Once in the suite, Jamie sets his notepad on the table and takes a deep breath. He smooths his blouse and stands waiting for Mr. Miller’s direction. However, David just takes off his jacket and immediately grabs something from the mini fridge.
“Here,” Mr. Miller takes a small bottle of champagne out, opens it, and pours a glass for Jamie. “Too a job well done today.”
The two clink their glasses before taking a sip.
Mr. Miller watches Jamie carefully, taking in every detail, which makes him a little uncomfortable.
“S-Sir…?” Jamie sips again before placing his glass onto a nearby table. “Is something wrong?”
“David, please,” Mr Miller smiles. “No, nothing is wrong. I was just wondering where all the man in you went. You look so… sexy. Like you were born a woman.”
“Oh… thank you…” Jamie blushes a looks away
Silence for a moment as David continues to drink. Then, as she pours himself another glass, David leans forward and touches Jamie’s chin to lift his gaze.
“Well, young lady,” David smiles, then gestures down to Jamie’s skirt. “Show me where your manhood has gone. I wanna see it.”
“S-Sir….?”
“Young lady,” Mr. Miller commands, sipping his drink. “I’m the CEO. I want to see you pretty little cage.”
Slowly, Jamie lifts his mini skirt, exposing the bulge hidden beneath his pantyhose and panties.
“Ah, very pretty,” Mr. Miller stares before chuckling to himself. “How's that feel?”
“Erm….” Jamie looks away before brushing hair from his eyes. “I’d kinda forgotten about it. At some points, it was uncomfortable.”
“Ah, very good.” Mr. Miller swigs back his entire glass. He then heads into his bedroom, leaving the door open and Jamie standing awkwardly, still holding up his skirt.
Then, after a moment and a lowering of his skirt, Jamie hears Mr. Miller shouting all sorts of curses from his bedroom. Not sure what to expect, Jamie rushes into the room and finds Mr Miller glaring out of the bedroom window and across the hotel courtyard.
“Is everything okay, sir?”
Mr. Miller looks back and then points out the window, which overlooks the suits across the other side of the hotel.
“No. That bloody Rohan has his hands all over his assistant! He’s taunting me.”
Jamie steps closer to the window, and Mr. Miller is indeed correct. Mr. Patel is passionately kissing his assistant in full view of the window and anyone who cares to peer inside.
Jamie just stares for a moment before Mr. Miller positions himself directly behind.
“Quite the sight, huh?” Mr. Miller says and then begins to press himself up against Jamie from behind.
At first, Jamie thinks nothing of it, but then something hard gazes at his hand. It’s Mr. Miller’s erect cock through his trousers.
Expecting that to at least make him recoil away, Jamie surprises even himself as he slowly turns his hand and holds it on Mr. Miller’s bluge, feeling just how big and hard his boss has truly become.
“Young lady?” Mr Miller makes Jamie turn on the spot as he continues to hold one hand on his powerful bulge.
Even in his heels, Mr. Miller stands taller. Jamie just looks up timidly into his eyes while slowly rubbing his hands across Mr. Miller’s bulge buried inside his pants. A gasp soon follows as Jamie’s cage becomes increasingly uncomfortable.
He’s excited by this.
Jamie bites his bottom lip.
He is very excited by this.
“Found something you like, Jamie?” Mr. Miller comments as Jamie’s rubbing of his cock continues.
Jamie, whether instinct or desire, falls to his knees in front of his boss and finds himself looking directly at the bulge he was just rubbing. He looks up at Mr. Miller and bashfully smiles.
“C-Can I…?”
“Young lady,” Mr Miller laughs. “Only if you want to.”
Nervous, but growing with excitement, Jamie slowly unzips the man standing before him. Throbbing within his own cock cage, Jamie reaches into Mr. Miller’s pants and, with a tiny gasp of excitement, pulls out his boss’s cock
Hard and ready for action, Mr. Miller’s cock points directly at Jamie’s mouth.
“Go on…” Mr. Miller whispers, placing a hand on Jamie’s head.
Heart thudding wildly in his chest, Jamie opens his mouth and slowly guides his boss's cock into his mouth. Sliding against his tongue, Jamie can taste the saltiness of the day. Musty cock fills his every sense.
“Mmmmm.” Mr. Miller leans forward, pushing his cock further into Jamie’s mouth.”You feel just like a woman, Jamie. Keep going.”
Encouraged, Jamie slides Mr. Miller's cock as far back in his throat as he dares. Seconds later, Jamie coughs and gags, taking the cock from his mouth as saliva strings across the gap.
“Too deep…” Jamie gags and then composes himself.
“I’ll take that as a compliment,” Mr. Miller chuckles, holding Jamie’s head just enough to start guiding his cock back into Jamie’s mouth.
Very willing, Jamie takes in a deep breath and gobbles the cock gladly. Moans and deep sucking later, Jamie is getting more and more excited with each passing moment.
Every time Mr Miller calls him a good girl, his cock throbs, pressing desperately pressing against his tiny cage.
Faster and faster, Jamie sucks. More and more, he starts to moan as the thrill of sucking cock turns him on. Wearing heels, breasts, and a skirt just heightens how submissive he’s become.
Flash, Click.
Mr. Miller chuckles to himself as Jamie continues to go to town on his cock.
“That’s a keeper of a picture,” Mr Miller groans, holding Jamie’s head. “You’re such a good girl!”
Just like that, Mr. Miller’s cock throbs and pulsates in Jamie’s mouth. He knows what’s coming, and that makes him even more excited. He bobs up and down on Mr. Miller’s cock faster and faster until…
Mr. Miller grabs Jamie’s head and forces himself deep. Cum spirts from his cock, coating Jamie’s mouth and filling the back of his throat.
Salty, sticky, and viscous, Jamie tries to swallow, but he’s overwhelmed with sensations. From sore knees kneeling on the floor, to breasts hanging from his chest, to the smell of his boss's crotch, to the cum swilling in his mouth
“Swallow it.”
Jamie looks up at Mr. Miller’s delight expression. He swallows down, but it’s like salty gross honey.
“Good girl,” Mr. Miller strokes Jamie’s long hair. “Now, give it a suck clean for me.”
Jamie obliges and does exactly that, licking Mr. Miller’s cock like a salty, sticky ice lolly. Eventually, Mr. Miller pats Jamie on the head, puts his cock back into his pants, and smiles.
“Well, we skipped all the kissing and got to the good part!” Mr. Miller laughs as she types out a message on his phone. “I hope Mr. Patel saw you on your knees in front of me just then.”
He laughs again, looking at Jamie, who’s still kneeling on the floor, catching his breath. “You, young lady, have taken everything I’ve thrown at you today, literally. I’m very impressed!”
“It’s a pleasure, Sir!” Jamie eventually replies, still trying to swallow down his boss’s seed.
“Need a drink? Mr. Miller throws his phone down on the bed after sending a few messages. “I’ll get us one. Heaven knows you deserve one for such a wonderful performance.”
Jamie nods and gets to his feet. Wobbling a little because of his heels, he falls forward and catches himself on the bed. Mr. Miller laughs as he leaves the room to get drinks, making Jamie blush even harder than he already was.
Now alone, Jamie tries to catch his breath and compose himself. He tucks away stray hairs and flattens down his skirt and jacket. As he does, Mr. Miller’s phone, still open, vibrates with a message.
Jamie can’t help but look down and see the message chain.
It’s from the company's CFO.
Richard – Wow, is that really him sucking your cock?
David – Yup. Looks at him noshing away at it like a big meaty lolly pop
Richard – Is that seriously the same Jamie?
David – Yeah. The same one we talked about last week. The guy with a fat ass that I bet would like fantastic as a femboy.
Richard. The one with great attributes?
David – Yup. Look again. He’s it’s him and he’s sucking on my cock. Which means, you owe me money. I told you I could get him to dress like a little whore and suck me off, didn’t I?
Richard – double or nothing.
David -?
Richard – Double or nothing. I bet you can’t have anal sex with him by the end of the conference.
David – I’ll take that bet!
Mr. Miller appears at the door, drink in hand. He sees Jamie reading the messages on his phone.
“Ah, sorry. I shouldn’t have left that open.” Mr. Miller leans against the door frame and lets out a long breath. “I’d imagine you're pretty pissed off. It wasn’t a mistake inviting you here, as I’m sure you’ve now gathered. I bet Richard I could get you to dress as a girl…”
Mr. Miller points at Jamie and smiles. “I did that.”
He then steps into the room and hands Jamie another glass of champagne. Jamie took the glass and just looked on, a mix of shock and excitement.
“And yes, I just sent him a picture of you sucking my dick to win the bet. Which you’ve done wonderfully at.” Mr Miller sips his drink. “I hope this doesn’t sour our trip away, young lady, just as things are starting to get interesting.”
Mr. Miller points out the window across to Mr. Patel's suit. “We’ve got my rival CEO jealous, I can tell. He couldn’t take his eyes off you. You should be very proud of the sexy little lady you’ve become. I knew you had great….. attributes!”
Mr. Miller stops talking and looks hopeful in Jamie’s direction.
“Well… are you angry at me?”
Still throbbing away in his panties, Jamie can feel his cock wanting to explode with excitement. He’s never felt so dirty and used, yet he kinda likes it.
He looks down at the floor, wondering if it’s because he’s pretending to be a girl.
“This bet….” Jamie finally speaks, pointing at Mr. Miller's phone. “What are you betting on?”
“Oh… erm…” Mr. Miller sips his drink with an almost sinister smile. “Who gets the biggest bonus this year?”
A smile tugs across Jamie’s face as she struts towards Mr. Miller with confidence. He leans in and whispers in his ear.
“I’ll let you fuck my ass if you cut me in.”
Mr. Miller is taken aback for a second before he reaches around to Jamie’s ass to give it a squeeze.
“Excellent negotiating, young lady!” he laughs, and squeezes again. “Consider this ass paid for. I want it ready for tomorrow night. We’re going to celebrate this new working relationship with a bang!”
“Yes, sir!” Jamie giggles playfully. “I can’t wait!”
Jamie smiles to himself. Karen’s never going to believe this…
Comments
GenderPlay Books
Ah yeah.... it was a commission so its not my usual work tbh
Annah Rourke
I read it, it was enjoyable, and not quite where I thought it was going is all
GenderPlay Books
So is it good or is it bad?
Annah Rourke
Not quite what I expected but im just one person and definitely no stranger to any of it
