The bet

“There has to be something better to do…” Phil grumbles in frustration as he spins around on his squeaky desk chair with his brows furrowing in thought. You join in, mentally ticking off things you’ve done in the past few years with your best friend as you also struggle to think of a new idea. Starting off as small harmless bets made to pass time years ago, the stakes and challenges began to climb as your friendship with Phil developed. These bet-like dares typically involves you trying to outperform Phil at the same challenge, sometimes winning or losing some money and pride. The games with him finally reached a tipping point when you both were arrested for a few days after being caught stealing a vase from an antique store you pleadingly swore to return afterwards. Agreeing to tone down the stakes afterwards, you’ve been brainstorming with Phil for the past week for things to do but everything seems to have been done before.

Abruptly sitting upright in his chair with an idea, he sheepishly smiles at you before sharing his thoughts. “I bet… I can look more like a woman than you in two weeks” he says with excitement as you look at him in confusion, processing his challenge as he pulls out a roll of cash from his pocket. “No constraints and anything’s allowed” he adds as you question his odd fetishes, but you can’t decline such a unique bet after winning a few of them recently. Shaking hands in agreement, the bet begins on a hot Sunday afternoon in Phil’s bedroom. Scrolling through your phone, you start to plan for the competition, thinking about things to change to your body to look more feminine. Crossdressing or altering your appearance to look womanly has never been at the top of your mind, but you’ve been always a little curious about the opposite gender.

“I could just get plastic surgery at Bangkok” you joke, glancing at Phil’s phone to see him scrolling through flights to the city. Realizing that he’ll go to extreme lengths to win the bet, you chuckle at him in disbelief as he grins at you cryptically. Contrary to his drastic research, you cluelessly scroll through feminine products and fashion in hopes of inspiration. After a few hours of scrolling down webpages, evening slips by so you wave goodbye to Phil and return home with a handful of ideas to contemplate in the comfort of your own room.

“Holy shit… girls have so many things to consider…” you mutter in frustration, still reeling from all the foundations and lipstick options available online before you even manage to watch make-up tutorials on how to use them. Shaving yourself and wearing girly clothes seems to be the easy part, but after looking at yourself in the mirror, you realize that it’ll be near impossible to make your entire body look feminine without drastic changes. With hope and victory drastically slipping away from your grasp, you catch sight of a website that sells make-up and tutorials for female actors; without any other options, you purchase the kit and hope that it’ll arrive in time.

After a few anxious days of waiting for the package to arrive at your doorstep, you excitedly tear open the bland brown cardboard to see a meticulously designed set covered with flowers and pastel pink. Carefully opening the box, you notice a USB stick along with a small handbook of instructions and a variety of make-up products and cream. Hastily plugging the thumb drive into your computer to play the instructions, your ears are immediately greeted with relaxing meditative music behind some narration from a British woman. Clicking through the options on the screen, you decide that a more feminine Asian appearance can win you the bet, so the program alters to meet your preference. Without wasting anymore time, you begin to shave your legs and any other bodily hair to the computer’s instructions, feeling oddly relaxed from the soothing music flowing into your head. Slowly rubbing the provided oils along your smooth and hairless body, you gasp in surprise at its effectiveness to see your skin tight and unblemished with a developing yellow-ish oriental hue of an Asian girl.

Pleased with the results, your confidence in the product begins to build as you eagerly click the button on the screen for the next step. “What the…” you mutter to yourself as it instructs you to apply nail extenders and polish on your fingers and toes; expecting it to be a disaster waiting to happen from your lack of experience, you shrug your shoulders and accept whatever the outcome is. Carefully attaching the extensions onto your nails, you unscrew the polish and begin applying it onto your fingers and toes, wrinkling your nose at its toxic fumes. To your surprise, you manage to perfectly paint your nails glossy pastel pink within minutes almost as if you have the muscle memory to do so. Wriggling your fingers and toes to air them dry, you notice them smaller and slimmer than before but you blame it on the illusion from your long nails. “Hmmm… what’s next…” you mumble to yourself, beginning to enjoy the music echoing in your room, unaware of your wrists and biceps thinning into dainty limbs devoid of any muscles. Clicking the screen for the next instructions, you don’t hear your shoulders simultaneously crunch inwards into narrower and rounder frame pushing your sharpening collarbone higher.

“Oh… some body cream” you say to yourself, digging into the package to pull out the matching product before checking the computer once more on where to apply it. Taking off your clothes to help spread the ointment throughout your body, you toss them carelessly onto your bed and open the container. Inhaling sharply in surprise, your body flinches as the cold cream makes contact with your sensitive and smooth skin. “Oooh… wow” you grunt, spreading the thick substance across your thighs and ass before pushing it higher to your stomach and back. Without warning, a warm wave of heat rushes through all the areas you smeared the cream onto as it starts to be absorbed into your body. Massaging the lotion into your thighs to speed up the process, you yelp as your slender fingers rub against your extremely sensitive inner-thighs, unaware of all the fat gathering under your skin making them thicker and juicer than before. “W-woah… were they always this big?” you ask yourself, squeezing your pillowy thighs and feeling them jiggle in your hand as they smother your balls in between.

The same warm sensation radiates in your belly as you look down to see it much flatter and toned than before. “Holy shit… also helps with weight loss” you laugh but furrow your brow in confusion; you’ve been dieting and exercising for a body like this for years. Shaking the conflicting thoughts out of your head, you let the music and narrator’s voice into your ears to calm yourself. Taking a deep breath with your smaller diaphragm, you feel your waist contract into an hour-glass figure you pride yourself with before letting the air out through your mouth. “Mhhm… much better…” you slur peacefully but it abruptly ends as your short arms accidently knocks the jar of cream onto the floor with a loud thud. Sighing with frustration, you lean down to pick it up only to yelp in pain as your spine suddenly cracks and your hips momentarily dislocates, sending you crashing to the floor. “Owww… what was that” you groan, rubbing your swollen hips, unaware of them already jutting out into child-bearing proportions. Your spine arches and pops a few more times as you push yourself off the floor, becoming permanently curvier to thrust out your ass and chest. A wave over vertigo hits you as your room feel so much bigger than before, oblivious to your petite height as you quickly get used to it and brush it off as the result of falling to the ground.

Walking back to your chair, the sway of your wide hips feel natural as more fat fills out the sides, making your hour-glass figure more prominent. “Now… where was I…” you mutter, leaning closer to the computer for a closer look as your ass begins to inflate with fat spreading your skin to its limits. Preoccupied with reading the instructions and distracted by the music, you don’t notice your ass swelling larger into a round bubble butt pushing you higher in your seat and spilling off the sides. You pause for a second to read a questionnaire asking for your feedback on the feminizing kit, so without a second thought, your long nails clack against the keyboard as you write a positive review. “Seems to work perfectly…” you mutter with a smile as slight oriental music begin to creep into the background and the narrator’s voice switches to an Asian woman.

“Take a shower and wash my hair?” you say quizzically, reading the instructions before grabbing the correct shampoo and body soap for the next step. You quickly increase the volume of the program so that you can hear it from the bathroom as you eagerly rush into the shower, feeling your feet crunching smaller a few sizes to match your petite body. The warm water soothes your aching bones after all the changes as you smile to yourself under the constant flow running off your curvy body. Applying shampoo to your head, you kneed the bubbles through your hair as the narrator begins to talk abut the importance of healthy and luscious hair. Nodding in agreement, you feel your hair running through your fingers as it cascades past your shoulders and forms a cute fringe over your forehead before turning jet-black. Finally rinsing the shampoo out of your hair, you tuck the long hair behind your ear as you remember spending considerable time blow drying it afterwards.

Reaching for the soap, you liberally rub it all over yourself, feeling your body tingle slightly as the narrator starts to talk about the perfect Asian body. “What the…” you mutter in surprise but continue to listen to her voice as your chest starts feel tender and soft under your hands. Massaging your nipples, you shiver from the new sensations as they harden between your fingers while your areolas double in size and darken. “Mmmphh… oooh…” you moan softly, feeling your chest pulsate as rolls of fat accumulate underneath your nipples, slowly pushing them out into your petite palms until you’re cupping your budding A-cups in your hands. The hypnotic voice of the woman rings in your ears as you succumb to the urge to clean yourself more, squeezing your breasts in your hands and feeling the flesh swell with fat as they expand into soft C-cups protruding outwards with round underboobs. Feeling aroused from all the stimulation on your tits, your hands creep closer to your dick already hardening with an erection and rub it top to bottom with the soap. “Ahnnn… mmphh… so… horny…” you moan, biting your lower lip as you feel your breasts growing heavier and ballooning into D-cups hanging off your chest like two full water-drops. Looking into your deep swaying cleavage, you giggle from the feeling of warm water gushing in between it feels completely natural to you.

The woman’s voice grows louder in your head as you listen to her describing the pleasure of satisfying a man with your body and mouth-watering pussy. “A… A pussy?” you murmur in a daze wondering what she meant as your hands wrap around your dick, stroking it up and down repeatedly. Your thoughts begin to race as something feels off, but you remind yourself of the bet with Phil to be the most feminine in a few days’ time. D-cup breasts and a curvy body is definitely girly, so why do you have a dick? You have a bet to win. Unable to hold back from the sensation of feminine hand stroking your cock, you finally give in and let out a torrent of cum into the shower as the salty stench smells oddly familiar. “Nuurghh… I need to be… a woman…” you grunt, squeezing your dick for everything until your balls run dry between your thick thighs before shrinking into your crotch with a wet slurp. Your eyes roll back in pleasure as your empty balls reform into fertile ovaries pushing your innards aside and pumping your body full of estrogen. “Hah… hah… yeesss…” you pant heavily with your breasts heaving up and down as your dick starts to become flaccid before inverting into your crotch too. The joys of being a woman and using your pussy described by the narrator fills your mind as your shrinking cock slips from your fingers and a puffy slit splits open in its place. “Ahhnnn… oh god…” you moan loudly with your knees buckling as your fingers push into your pink pussy lips and rub against your newly formed clitoris. Your vaginal muscles clench along your fingers, sending juices spraying down your leg and mixing with your cum as your body rocks with another climax.

Snapping out of your orgasmic daze, you notice your fingers starting to wrinkle from all the wet fingering in the shower, so you promptly hop out in hopes of preserving your pristine skin. “That felt… so good” you mutter to yourself with your heart still beating rapidly and your pussy aching from all the stimulation. Drying yourself off with a towel and on the verge of fingering yourself again from the rough fabric rubbing against your pussy lips, you make your way back to your computer, feeling your breasts bounce with every step and your ass jiggle in synchronization with your swaying hips.

The program asks for you to select your preferred Asian appearance to proceed with the next step, so you select a cutesy and submissive look in hopes of winning the bet by becoming a more girly and obedient woman. Accepting your request, the program begins to list out all the make-up you’ll need as the narrator starts to describe the importance of a perfect angelic face. Applying foundation and blush onto your cheeks, your jaw cracks smaller and softer while your cheekbones rise to form a more feminine appearance. Unaware of the changes to your face, you pat more powder onto your nose, feeling it shrink and narrow into a cute button nose as you let out a sneeze. “I look better already…” you grin to yourself, seeing the effect of the make-up on your face as you look almost androgynous with a slight Asian appearance.

Pursing your lips, you expertly put on lipstick as they cause your lips to plump up into juicy kissable pillows in a permanent pout. “Now for the eye--- aack” you cough from an itch in your throat, but you cover your mouth in surprise after hearing your voice cracking higher into a cute and sultry feminine tone with a thick Japanese accent. The narration and music calms you down once again as you clear your throat and giggle at your overreaction. Of course you have a girly voice to match your heavy breasts, wide hips and virgin pussy along with your family in Japan. Family in Japan? You hesitate for a second, as your memories conflict and your mind becomes hazy, losing large amounts of English vocabulary and replacing it with Japanese words as you struggle to form coherent English sentences from the limited classes you had in Japan. “I… I here to win… bet” you say repeatedly to yourself, trying to clear your mind as you remember meeting Phil and competing with him to be more feminine. You chuckle at the thought of him crossdressing and thinking that he’ll have a chance against a girl like you, so you plan on making yourself even more attractive than before. Finally putting mascara and eyeliner on, you blink a few times as your eyes widen into a doe-like appearance with visible slants on the side while your irises darken into a typical Japanese girl’s complexion. Smiling at your reflection, you let out a sigh of satisfaction after seeing your doll-like face on top of your D-cups and moist pussy.

“絶対に勝つよ [I’ll definitely win]!” you say to yourself in fluent Japanese as you lean over to turn off the computer and pack up the products all over the table. Your hand hovers above the mouse as the narrator’s voice becomes entrancing and the music blares louder in your ear. You find yourself blushing red with arousal and your pussy aching to be filled as the voice starts to speak in Japanese, detailing all the ways to satisfy man. “No… he… he my friend…” you stutter, trying to stop thinking of Phil but he seems to match everything the narrator says; his masculine scent and hulking body is the person you are made to pleasure. “My… my boyfriend?” you gasp in realization as you imagine him pinning you down and fucking you raw every night as obey his every command.

Breaking out of your daze, your focus returns to the computer as you backtrack a few steps in the system and select a new appearance you want to obtain. “M-make him love me… and win!” you grin at your new plan before taking out a comb and brushing your hair with it. Within seconds, your hair cascades down to your lower back, becoming dense and wavy with brown highlights you know Phil secretly adores. Applying more eyeliner onto your top eyelid, you feel your eyes narrowing into a seductive foxy slant while your irises take on a lighter grey color. Batting you long eyelashes, you smile at your new appearance before applying another tone of lipstick, causing your lips to rapidly swell further out into pillowy cock sleeves. “Me sexy!” you giggle, giving yourself a playful wink in the mirror as you hear your doorbell ring.

Reaching for the door with your hips swaying side to side, you hear a familiar voice echoing from behind, “Hey… about the bet… I don’t think I ca---” Phil mumbles awkwardly as you swing the door open to reveal your naked petite Asian body to him. His jaw drops open in surprise as you lustfully eye him top to bottom, noticing a boner rising in his pants. The narrator’s voice continues to ring in your head as the urge to obey her and be the perfect submissive girl for your boyfriend becomes overwhelming. “W-who are you?!” he splutters, unable to tear his eyes away from your jiggling breasts and leaking pussy as you hungrily stare at his crotch.

“Mayumi…” you blurt out with a giggle, the name feels so natural in your mind as if you had it your entire life. “Me win… bet?” you slur in broken English as you lead Phil into your room before pushing him against the wall and placing your small hands on his crotch, feeling his cock pulsate in your palms. Just looking into his eyes makes your heart race as his masculine scent makes you makes you even more aroused than before. “M-me so horrrrnyyyy” you moan softly, breathing into his ear as he begins to passionately kiss you, invading your mouth with his tongue before effortlessly picking you up and pinning you onto your bed. You smile at him encouragingly as he tears off his pants, confident that you’ve won the bet by becoming his dream girl, before feeling the tip of his cock tease your pussy lips.

“H-how did you do it? It’s so… real” Phil stutters, hesitating on whether to impregnate you but you giggle at the stupidity of his question. The basic beauty kit you used to make your already feminine body even sexier seems to be a big deal to him; boys just never understand the effect of some simple make-up. “Y-you’re like someone completely different…” he mutters but you prove him wrong as you grab his hand and place it on your breast, remembering all the times he groped you and sucked on your puffy nipples. You moan softly as he squeezes your tits with one hand while the other strokes your pillowy thighs, making you shiver in anticipation.

“Mmhm… fuck… me…” you whisper with a wink as he finally gives in to his burning arousal and thrusts his dick between your open legs, making you yelp in surprise. You feel your breasts sway as his dick slides into your virgin pussy, spreading your tight lips apart and pushing deeper into your vagina. Your toes curl and eyes clench shut in both pain and immense pleasure as his girthy cock breaks your hymen and splits your insides apart, aided by all the juices you lubricated around his shaft. “Ahhnn… もっと深く [Go deeper]” you pant as the tip rams against your womb, forcing your vaginal muscles to clench against his dick; the slightest touch of his veiny cock rubbing against your clitoris sends you into an orgasm. Overwhelmed with the desire to pleasure your boyfriend, you arch your back and shift your hips around his dick in hopes of enveloping every part of his cock in your warm and moist pussy. “Nurrgghh… m-moreee…” you moan with your breasts bouncing as he thrusts his dick in and out of your gaping pussy, letting juices run down your thighs as your eyes roll back from another orgasm. You finally feel his cock twitch inside as you eagerly clamp your muscles against his shaft, hoping to milk him for his hot seed as the prize for winning the bet and looking more feminine. Without warning, you feel a wave of cum flood your insides as he blows his load into you, making you giggle with happiness; you’ve fulfilled you duty as a woman to pleasure your man.

Panting for breath on the bed, you feel your heavy breasts rise and fall as your boyfriend slides his dick out of your pussy, sending a stream of cum and juices from your overfilled vagina. “I… have a bet… first to cum wins…” Phil grins as you look at him with lust. That’s a bet you’ll win for sure you think to yourself as you shake his hand to accept the competition.