Pretty Little Head

This is a request for a long time pal who really likes seeing Boys get turned into Pretty Wives and Cuties, but for this one, he isn't trans! At least I don't think he is. He's just a wife, who is a boy. As one does! Lots of programming, obedience, and soft squishy stuff to be had as well, with a good ending! Anyways, hope you dig it!

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It had all started as all good things do: with an MP3 file and a pair of cat ear headphones.

Sure, all kinks had to start somewhere. But River had no idea how far they'd go with this hypno fetish stuff! His girlfriend, Avery, had devoured the content voraciously, something he'd known about for as long as they'd been sharing their erotica. So many stories and pictures and videos of hotties and cuties trapped in a spellbound somnambulance, given instructions to perform, cravings to sate, even thoughts to have. Slowly, he'd been integrating that content into his own masturbation routines. Then they'd gotten off together, looking at the same stuff. Then...well, one thing led to another...

He'd been nervous at first; he wasn't exactly a super dominant guy after all. Short for a guy at around 5'7 and a little timid, he was worried that he wouldn't be able to exercise the kind of calm but authoritative presence that being a hypnodom required. But she'd been patient with him, giving him pointers and adjusting his presentation. Ironically, there were even some audio files that had helped boost his confidence. And now he could put her under and make her scream his name with the snap of a finger, just the way she liked.

Of course, River'd be lying if he said the sight of his perfect, pretty girlfriend totally under his control didn't get his engine going too. The power of telling her she was a princess or a puppygirl or a nurse and her totally believing it...it was intoxicating! So when she'd told him, point blank, that they'd be doing something much more intense when she came home from work this Friday Afternoon, he'd had to keep himself from pacing a hole in the carpet.

Last week, she'd told him to whip up a special file. They'd experimented with custom files before for little things, like giving her a propensity to giggle when she saw the colour pink, or play with her hair when she was thinking. But this time, she said to go all out. Pull out all the stops, dig straight into the good stuff.

She wanted a file to make her into a dizzy, cutesy housewife.

His phone buzzed. His excitement made him nearly lose his grip on the device, entering his password and reading the text message.

*Package inbound. Get ready!*

"Package?" he said, a feral smile crossing his lips. Another costume, perhaps? Oh he couldn't get enough of the last one. He'd asked to fuck her while dressed as a magical girl several times, once even while she wasn't even hypno'd. It had been so hot, just lifting her pleated skirt and going to town. Just the memory made him stiffen in his track pants and old concert tee, his default work-from-home clothes. Not sexy, but then again, he wouldn't be the one on display today!

A knock at the door. River took a moment to rearrange his junk before going to greet the poor, unwitting delivery person. They'd left the package on his door, and he snatched it up, unable to help giving it a shake. Something rattled from within, but the rest of the noise was muffled. Clothes, likely. Another sexy outfit? He could only hope!

*Package arrived!* he confirmed, a few moments later, he got back-

*Open it up! I'll be home soon. Project meeting's running long.*

He frowned.

*Don't you want me to wait?*

*Nah, go ahead. There's a little something extra in there too, if you catch my drift ;)*

River chuckled to himself. God he had the best girlfriend! He was practically licking his lips when he sliced open the packaging and threw open the cardboard. Inside was an outfit, but not one he was expecting.

Wrapped up in a neat bow was what looked like a traditional shirtwaist dress, the kind you might see in a 1950s sitcom. It was pink, with white polkadots and buttons. It was pretty though. And the fabric was silky smooth! Must have cost a fortune. He caught himself feeling up the sleeves before taking out a safety knife and cutting it free of the little ribbons that kept it in place. But as he unfurled it out of its box, he noticed something strange about the outfit. It wasn't her size! In fact, it was much larger.

He texted her to let her know that something about the shipment was wrong, that it was easily three sizes too big for her. As he played with the skirt, however, an object fell out of the wrinkled fabric.

It was a bright pink chastity cage.

River blushed. That was a new one. They'd never talked about chastity play before. But how could he be the dom if he wasn't allowed to get an erection?

His phone buzzed again. He was still examining the little plastic cage, opening his phone up with his off hand. Absently, his eyes roamed over to the screen to see her response.

*Don't you worry your Pretty Little Head about it, sweetie*

His eyes froze. Everything about his current train of thought exploded into little pink sparkles. He smiled broadly, unashamedly, for the first time in a long time. All the weight of the world seemed so far away, and the only thing he could focus on was just how cute this dress was! He held it up to his shoulders, like he was trying it on at the shop before buying it. Funnily enough, it looked to be his exact size!

*Haha, okay!~* he sent back, really struggling to find the tilde button. They always had to hide it!

*Why don't you try it on? You know we both love playing dress up together* she sent in reply. That was...partially true. He'd never been the one in the costume, though. But that didn't mean he wasn't up to trying it out! With a giddy thrill of doing something naughty, he stripped out of his yucky, bland clothes and tried slipping on the dress. It was a little snug, but then he remembered the buttons! Laughing at his silliness, he tried again, this time unbuttoning the pink garment before slipping it around his shoulders. Success!

*Done!* he texted, a little proud of putting on his very first dress.

*Good Girl*

The words hit River like they were a shot of a literal drug. He moaned out loud, causing him to clap a hand around his mouth afterward in total shock. What was getting into him?! Before he could wonder further, however, he got another text.

*Did you put on everything in the box?*

He looked back to the chastity cage. It looked so small, barely enough room for his cock when it was fresh out of the shower, let alone if he was excited. Which, looking down at the tent in the fabric, he very much was.

*I don't think it'll fit...*

A pause, then a reply.

*That's alright sweetie. You can focus on your chores for now.*

He tilted his head. *Chores?*

*Of course! Housewives always do their chores, don't they Princess?*

His fingers moved on the phone before he knew what they were doing.

*Of course, hubby! Dishes first!*

Hubby? River thought he was the husband! But he looked down at the text message he'd sent, he'd just called Avery his hubby. But what did that make him?

*Thank you, wifey~* came the answer, and the reply, and his little heart surged with joy. He was the wife! Of course! But...he shook his dizzy head lightly, trying to form a coherent web of thoughts. He was...he was River. River was a pretty name, but he was a boy...but the text said he was also a wife. Also: new information had just come in that said he was a good girl too. It was very confusing! For now, he decided to just go with what felt good. Maybe his hubby would clear it all up later.

The first chore he had to do (ugh, chores!) was the dishes. It was just last night's pasta preparation and the two plates, thankfully not a laborious task. With a sigh, he ran the tap and got out the dishwashing liquid. But as he squirted some soap onto one of the messy plates, he discovered something peculiar.

Whenever he did something to further his goal, he felt a flicker of pleasure. Not a huge parcel of endorphins like he'd gotten from the texts from Avery, but a little smidge, a little glimmer of bliss. He carried on to wiping the plate clean under the hot tap, and it was like connecting to a drip feed of puppies and pink frosting. He quickly cleaned both plates, the forks, and got deep into the pans that needed scrubbing. And they needed scrubbing! He pulled out a pair of dainty gloves that they'd gotten at the dollar store but never used. Wouldn't want to ruin his nails! Wait, his nails? He pulled the glove back. Oh my gosh, they were a mess! That would have to change the moment he got his chores done!

Soon the dishes from last night were all done and sparkling and on the drying rack...but he wanted more. He opened the cabinet and looked at row upon row of clean plates. Surely there must be something still left on those! He carried them over to the area next to the sink and got to washing!

Plate after plate fell to his persistent cleaning mania, all while the strange pleasure seeped into his spine and made it tingle. The bulge in his pretty dress didn't go away. If anything, it got worse! He was washing plates in a frenzy, rock hard, and couldn't have been happier.

Relenting as the last dish they had finally fell to his cleansing clutches, he regretfully determined that the dishes had been done. Slipping off the gloves, he went back to text Avery the good news.

*Good Girl* she replied, then *You may open the second box now*

It took a long moment to come down from the euphoria of the first message to read the second. A slight stain had appeared in the front of the pink skirt. Oops! Must have spilled some water down there!

*Second box?* River asked, getting a little excited at the prospect of more dresses!

*It's under the bed. Put on everything inside, then go do the laundry. Do you understand, honeybunch?*

He nodded. Then, dimly realizing she couldn't see him nod, followed up with an actual *Uh huh!* to let her know he understood! Gosh, two whole packages? How lucky a wife was he?

As he ascended the staircase, something tickled at the back of his mind. Something was telling him that this was wrong somehow. This was roleplay, he countered. It was different from actual life! He remembered lots of times they'd roleplayed together, and how much fun it had been. But in all his memories...hadn't he been the one in charge? Hadn't she been the one wearing the pretty outfits?

He reached their bedroom and pulled out the box he found there. It must have been from the same company as the first. How long had Avery been planning this, he wondered. With barely any restraint, he tossed it open upon the bedspread and peered in. At first, he was disappointed. It wasn't a new dress! But as he pulled out the gaudy tissue paper covering the contents, he realized it was something much more fun!

Inside was a set of lacy underwear: bra and panties, specifically, fitted just for him! And underneath it...a pair of long white socks and some pretty pink flats to match!

He opened up his dress for a moment, suddenly reluctant to take it off entirely. Settling for letting the top half fall, he worked to reverse engineer how he'd taken off Avery's bra on many occasions to put his own on. When the last hook slipped into place, he felt a sudden...presence, on his own chest. He squeezed himself, and gasped! It was like his nipples had become super sensitive! Maybe these really were breasts this whole time, and he'd been just exposing them to everyone whenever he went to the pool! Blushing, he turned to the panties.

These were more difficult than the bra, but for a completely different reason. They were specialized panties for cuties with a little extra between their legs, but even then, his rock hard cock was not cooperating. He whimpered pathetically, trying to fit the cute clothes around his cock but it kept slipping out!

*Honey...my panties won't fit!* he sent, completely without shame.

*Oh no! Did you put on your pretty pink cage?*

*No, that didn't fit either.*

*Sweetie, only bad girls don't follow their instructions...you don't want to be a Bad Girl, do you?*

His fingers stabbed at the letters N and O so fast the screen nearly cracked.

*Then,* she sent after too long a wait, *You're going to need to make your little thing get small enough to slip it on*

The screen filled with hypnosis videos, sent one after the other in a chaingun stream of mind-melting content. Each featured a Good Wife just like him, utterly blissed out and obedient. Appended at random intervals were words like "Good Girl" and "Obey Your Husband" and, most importantly, "Touch Yourself".

That was all the permission River needed! Lifting his skirt, he stroked himself into a frenzy, his other hand keeping the stream of hypno porn in direct eyesight at all times. This time, unlike any other, he imagined it was him on his knees for his hubby. His eyes staring blankly at a swinging watch. His ass presenting and ready for inspection as an enormous cock pressed against him and threatened to take him completely.

*I'm close.* he told her, reacting to some unknown stimuli that made it imperative to ask permission before climaxing.

*Yes, but only inside your panties* she replied. He groaned, seizing his fresh, barely out of the store garment and pressing it to his cock. In moments he was debasing it, corrupting its wholesome softness with thin ropes of girly seed, his masturbation session apparently not long enough to shoot anything but a few pathetic squirts. It was enough to make him cry out though, doubling over as if he'd just had the best sex of his life...directly into his own underwear.

But, as the orgasm faded out, he noted with pride that his cock was shrinking! He put on the rest of his clothes, feeling the dirty panties slide against his flesh, then slipping on the socks and shoes, only to bolt downstairs just in time! He quickly slipped the parts of the cage on before he could start feeling tingly down there again, clicking it in place. A part of him relaxed, safe knowing that his erections were no longer out of control. He didn't have to worry about that, at least for a little while. He played with the cage, watching his imprisoned shaft wiggle. So cute!

He hustled to the next room to get to work. The laundry had been piling up, after all! The dirty stuff was almost done, so some quick shoves and lifts got the washer on the go. But when it came to emptying the side-loading dryer, a part of him...lingered, on the act. He thought about bending with his knees, like he ought to. But something told him it would be hotter if he bent with his back. If he bent in such a way to show off his rear...

He did so, and grinned. What if Avery was here to see this? Him bending over and showing off his ass like a total perv. He turned to the full-length mirror they had down here and tried it, looking over his shoulder to watch. Devoid of context clues and familiar features, there was a cute person wearing a pretty dress trying to get his attention. His nethers stirred, then halted, as the plastic prison proved too much for him. He showed his face to the mirror, biting his lip seductively. More twitching, as his own antics tried to get him hard...

Realization dawned on him gently. Oh, he realized, he was under a hypno spell! It was the only explanation for all this strange behaviour on his part, but...he couldn't quite remember how or why he'd been so thoroughly programmed! This was critical information, he knew, but the more he thought about it, the less it mattered in the moment. As he strained his overtaxed brain, trying to think, that demure hottie in the mirror was waiting for him. He pushed the thought aside, flipped up his skirt, and did a silly little dance to entertain his equally slutty reflection.

Only the lure of more tasks got him back from being a flirt. He left the mirror with a wink and an air kiss and dived straight into folding clothes. He remembered that it had once been such a boring job. But the same joys he felt washing dishes transferred over to the laundry! As he got started, he couldn't stop! The individual folds left a little to be desired....he was kinda bad at it normally. So he folded all the clean clothes a second time, this time slowly, savouring every crease and twist to make it a project worth being proud of!

As he sectioned off their clothing onto either side of their couch, where they lay out the laundry normally, a sense of sadness lingered. Avery always had such cute outfits. Such pretty dresses. Such gorgeous blouses! And when he looked at his clothes, they all looked so drab. So colourless! Greys and blacks and dark blues, with a smattering of whites and a single red shirt. It just wouldn't do! Briefly, he imagined throwing away all the boring clothes and picking out some new ones at the mall. Maybe with Avery! She always had such good taste, and she picked out the pretty dress he was wearing! They could go to the nice ladies at the counter and ask for all the prettiest dresses in his size and golly his heart nearly burst out of his chest!

He had to calm down! A little excitement could go a long way! He flopped onto the couch in the space between the two sets of clothes, fanning himself like a Southern Belle in distress. A quick inspection of his panties let him know that he'd actually started leaking into them somewhere around rolling up the socks and folding the last of the towels. Chores were just a little too fun, he surmised, and flicked the skirt back down, smoothing it out. With a start, he dashed back up the stairs to fetch his phone. Drat! The one thing dresses needed was pockets!

*Finished folding!* he announced proudly. Then, after a little while-

*Good Girl! You're doing so well! You earned another box. Check behind the dryer.*

Obediently, River went over to where she'd indicated, pulling out another package. This one was a different colour, and slightly smaller. But opening it up on top of the washer, it was proven to him that sometimes great things come in small packages!

Inside was his very first makeup kit! It had lipstick, and eyeliner, and blush, and all the amazing wonderful things that pretty cuties wore when they wanted to feel extra cute and pretty! And besides that...he gasped! Inside the box was an actual set of earrings...and a pearl necklace!

*OMG* was all he could manage, fumbling with his gifts totally unsure where to start

*You're very welcome. Just follow the instructions with the makeup and take your time. The earrings are clip ons for now, we'll get your ears pierced later, okay sweetie?*

He nodded again, this time totally forgetting she couldn't see that. Taking a cue from her text, she tried the makeup first. Inside, next to the box of cosmetics was a little primer on how to makeup your face for the first time!

River took the box to the bathroom and followed the instructions as best he could. With his brain so full of pink cotton it was difficult to focus on hard words like "contour" and "accentuate", but the pictures were really helpful!

First, a shave! Warm water and a razor made quick work of his stubble. He hummed the whole way while he softened his face to look smooth and pretty, masculinity melting off his skin and sliding down the drain. Then he got to work with the serious business! Foundation and concealer, just like the pictures showed. He got a little turned around after this, so he skipped straight to a ridiculous amount of blush, some quick smokey eyeliner, followed by what else but some ruby red lipstick! River's eyes locked onto the pretty cutie in the mirror as he went round and round with the red tube of cosmetics, making a kissy face at his own reflection at the end.