Jessie's Daughter (Patreon)

Ash Ketchum was not in a good mood at all. He had another argument with Misty over what was more important for a Pokemon and its trainer. He had thought she'd of learnt her lesson the last time they were in Scissor Street when she was made to look like a idiot literally by Team Rocket's salon, but no, she made the remark again that it was important what was on the outside, where's Ash argued it was the inside and they went back and forth on the arguing till Ash decided to walk off.

Ash felt he needed some time to himself after being so mad at Misty, even leaving Pikachu with Misty and Brock. They had returned to Scissor Street to kill some time for the Pokemon League. Granted, Ash was supposed to be training for the League, but occasional mishaps kept putting him off or distracting him, and since they were in the area, they decided to stop by, since Brock insisted on catching up with Suzy. Honestly, it felt to Ash like he was in a weekly TV Show with all these random events going on in his life, whether it be Team Rocket or some trainer or Pokemon somewhere that needed his help or advice.

Soon enough, Ash found himself in front of a salon called Salon Beauty. It reminded him of Salon Roquet, an operation by Team Rocket in the past he, Brock and Suzy stopped last time they were here. He did not know why, but he was drawn to it, like something was telling him to go in. Was it to somehow prove Misty wrong, or did he fear this was another plan by Team Rocket to exploit trainers and their Pokemon with fashion? Whatever it was, a look couldn’t hurt. He had learnt by now that if he was dealt by a trio that seemed familiar in some way, there was a 99.99% chance it was Team Rocket in disguise.

“Welcome!” greeted the lady at the desk inside the salon. “You hear for a make over young boy?”

So far so good, there was only one woman running the salon. Ash relaxed at this point and was no longer suspicious.

“Oh me?” Ash pointed to himself. “Well, I dunno, I just...”

“Oh nonsense!”  The woman walked over to Ash. “You cannot possibly think this scruffy hair is trendy, or these clothes look appealing? Honestly, it's like you've been wearing and travelling in them for over a year!”

“Well actually...”

“Worse then I thought! This calls for a free make over young man! I will make sure you come out of here looking so fabulous, you'll look like a different person!”

The woman began pushing Ash into another room.

“But Miss, I....”

“No buts, I insist I make you over and make you my greatest work! You don't wanna look like a tramp for the Pokemon League now do you?”

“Hey, how did you...”

Before Ash could finish talking, he was forced onto a table faced upwards. With back felt against the cold metal table, the woman began strapping him in. Straps were applied to his wrists, his ankles, and his neck, tightly securing the young trainer and making escape impossible.

“Who are you?” Ash demanded. “And why in Kanto are you doing this?”

The woman only grinned and giggled in response as she threw off her pink salon uniform to reveal who she really was.

“Jessie!” Ash growled at her.

“Surprised twerp?”

“I should of known, this was yet another Team Rocket operation, isn’t it?”

“Not quite.”

“Huh?”

“While I did open this salon, it wasn’t for Team Rocket purposes. It was for my own use and plans.”

“Then where are...the other two you hang around with?”

“Oh, James and Meowth? I sent them on their own errand...”

At the exact same moment on top of Mount Silver in the closest and most hectic blizzard, James and Meowth were stood freezing to death on look out, searching for their objective.

“I-I-I-I-I D-D-D-Don't t-t-t-think that s-s-s-shiny heard of A-A-A-A-Artic-c-c-cuno are gonna s-s-s-s-show J-J-J-James!!!” Meowth stuttered as his teeth grinned from the sheer coldness.

“M-M-M-Me n-n-n-n-neither....” James said likewise.

Back at the salon.

“...but either about them, it's time for your make over!” Jessie smiled, holding up a pair of scissors and a make up kit, while slowly walking towards the bound boy. She began by cutting his t shirt in a straight cut, revealing his chest, before cutting his vest and the rest of his shirt off, leaving him topless.

“Hey, those are my favourite clothes!” Ash complained.

“Oh zip it!” Jessie told it, taking out some tape from her pocket and applying some to Ash's mouth, in effect silencing him. “There, that should keep you quiet.”

“Mrrrph mrrrph mrrrph!” Ash moaned through his tape gag.

“Oh just be glad I didn’t shove your underwear in your mouth before I gagged you! Besides, I'll take the gag off shortly when I need to.”   

With Ash silenced, Jessie began cutting away at his jeans. Tough as it was, the scissors were strong enough to cut through the jeans like a soft fabric. After slashing away at the jeans, Jessie threw off his shoes, socks and baseball cap, leaving him bound in nothing but his boxers. It was not for long though, as Jessie cut off the boxers, afterwards Jessie stood back to admire the sight before her.

“Tut tut.” she tutted, looking down at a particular area. “I must say, you make a rubbish boy Ash Ketchum, judging by that body of yours! Still, that can be fixed!”

The red haired Team Rocket member walked over to a dresser in the room and took out something that took Ash by surprise, a red and black corset.

“Mrrrph? Mrrph mrrrph mrrrph!!!” he moaned through his gave as Jessie came closer to his holding up the corset.   

“You should count ya self lucky, this is one of the corsets I personally use to get this fine ass body of mine! Wonder if I can get it to fit on you and eventually, into shaped?” Jessie winked, beginning to put the garment around his waist. Once fitted on, Jessie places her hands behind Ash's back to do up the lacing as best she could with the boy strapped to the table. Ash could only scream through his gag as the corset grew tighter against his body. Clearly it was not meant for a boy his size, let alone a boy, but Jessie got it on tight enough.

“Hmm, not bad.” Jessie looked at the corset. “You'll get used to it as it shapes your body to how I want it. Then I'll tighten it more and more till you match my own shaped, haha!”

While the corset was tight, Ash could still breathe properly, but it did feel like he was being squeezed like a tight rope around him tied too tightly. Jessie returned to the dresser and then returned to him with something else. If the corset was shocking to Ash, the two new things would be jaw dropping.

“I think now you get the idea where I going with this by now.” Jessie explained, holding what looked like two breasts in her hands. “These false boobies are made of the finest and more realistic materials. They're designed so people can hardly tell the different and they're designed to STAY on the body without fail!”

Jessie began applying a gel on the back of each fake breast, then firmly sticking each one onto Ash's chest, hiding away his man nipples. The gel felt cold at first but then warmed up as it stuck onto his body.

“See?” Jessie pulled one of the breasts tightly. “They can only come off with a special gel, which only I know where to order!”

“MRRRRRRRRPH!”

“If you want me to take these off after I'm done with me, you'll do as I say, or forever be the boy with girl boobies, understand?”

Ash stayed silent, not sure of what to do.

“UNDERSTAND?”

With tears in his eyes, Ash slowly nodded his head. This was already humiliating as it was, so he did not want to be stuck as he was. Even without his newly given fake breasts, he knew Team Rocket could be dangerous, remembering back to that incident at the Safari Zone with the warden and the gun that got into Team Rocket's hands. He had no choice, he had to do as Jessie instructed, or things could get ugly.

“Now, let's sort out that scruffy hair! But before that, let's get you into a more fitting setting...”

Jessie began undoing the straps holding Ash to the table. Standing by his word, or rather silent agreement, Ash did not struggle or try and get free, instead letting Jessie take him to another room, one that looked more like a salon then the last, with a red salon chair, a large mirror for those sitting in the chair could see themselves, along with a wash bowl and tap below it, and all sorts of scissors, hair products and make up.

“There, isn’t this a much nicer setting?” Jessie smiled. “Now, let's get you into something less......nude.”

From a coat hanger, Jessie grabbed a pink fluffy robe and helped Ash into it. Ash had no objection, since after all, he was just given fake breasts that he could not get off on his own, so it could not compare to that.

“Now onto that hair.” Jessie spoke as she pushed Ash into the salon chair and then strapped his wrists into the chair arms. “Head back twerp.”

Ash did as he was told and moved his head down into the bowl. Jessie began by turning the tap on, soaking Ash's hair with warm water.

“First off, we're gonna sort the length of your hair. It's too short for what I have in mind, so this hair growth conditioner should do the trick!”

Squeezing a yellow bottle labelled Hair Extender; Jessie put the conditioner in Ash's wet hair and began to massacre it into his scalp. The poor boy could only see the ceiling, but feeling Jessie's fingers massacring his head and rubbing the conditioner into his hair actually felt nice and made him relax a bit more. He also felt his roots spring to life as his hair grew longer and longer, beginning to fill the bowl with black soggy hair.

“Like that don't you? Well, wait till I put this formula in your hair!”

Jessie squeezed another larger red bottle of a different liquid into the bowl and on Ash's head and began massacring again. Rather then lengthen Ash's hair this time, the conditioner began to change Ash's hair into a different colour, from the darkest black to the brightest red. As Jessie pulled Ash's head out of the bowl when she finished, so much hair hung from Ash's head, touching the floor in a small pile and damping the floor so much in its wetness. To solve this problem, Jessie took out the biggest hair dryer Ash had ever seen in his life from a cupboard, one that required Jessie to hold with both hands. Switching it on, she blew the dryer at Ash's long hair, drying it so very quickly. It felt so hot to Ash, almost feeling like his fire was on fire.

“MRRRRPH!” He moaned as his hot hair blew in the dryer air.

“Relax, its perfectly safe.” Jessie reassured Ash. “The heat is just below the point of burning your hair and head!”

“MRRRRRRPH!” The calmness Ash had from the hair washing had now returned to panic, as he clear thought she was insane and begged for her hair to completely dry as soon as possible. Soon enough, his hair was completely dry, if a little hot.

“There we got, all dry for the big reveal!” Jessie smiled, putting the dryer away and the returning to Ash to swirl the around so Ash could see his reflection in the mirror. His eyes widened at his appearance, having longer red hair that ran down the back of his chair and on the floor. He knew it was long, but the red was news to him, Jessie even dyed his eyebrows in the same colour. He felt like a cross between a relative of Jessie's and a red-headed Rapunzel. Jessie then placed a small photo of a girl on the bottom of the mirror.

“See this? It's me when I was eighteen. Don't I look so much prettier then that twerpet you hang around with?”

“MMRRRRPH MRRRRPH!”

“Well anyway, this is the look I'm going for you! But first, we've gotta cut off all that excess hair of yours!”

Ash's heart went beating like crazy when he saw that evil grin in Jessie's face and the large scissor in her hands that looked almost like hedge cutters.

“Now hold still. You don't want a cut now do you?”

Ash was so frozen in fear he could do anything but move as Jessie began by cutting a large snip of the hair, leaving Ash with enough hair to reach his lower back. A few careful snips here and there to tidy the twerp's hair, and Jessie had finished successfully without harming Ash...physically. Mentally, he felt a mess.

“Time for curlers!” Jessie sung happily, opening a draw fully of pink curlers. With each one, she rolled it into Ash's red hair till Ash had no hair hanging from his back and had over a dozen curlers on his head.

“Now let's turn them on!” Jessie took out a remote and pressed a red button. The curlers began to heat on Ash's head, warming not too hot like the hair dryer, but at a more relaxing temperature. If only Ash was not gagged, he would be sighing right now, looking more like his mom when she's curling her hair then a normal boy.  Five minutes passed and Jessie switched off the curlers via the remote. She began to slowly remove each curler as gently as she could.

“There, miles better then scruffy hair isn’t it?” Jessie smiled once she took out the last curler. Ash was now a redhead with curly hair. For the first time in his life, Ash's hair felt so soft and bright, like if he could brush his fingers though it, they would not get stuck in the hair and feel really nice to touch.

“Not quite like mine yet though, we need to curl them one more time!”

Return from the cupboard, Jessie brought out two larger pink curlers the size of six packs of soda cans. The first one, she rolled up Ash's hair on the left and with the second, rolled up the right side. The two curlers were now rolled up on each side of Ash's head, like two hair buns. Once again, Jessie pressed the button on the remote to make the large curler heat up. Ten minutes later, Jessie switched off the curlers and removed each one from Ash's hair. Instead of curly, Ash's hair now looked like it split in half and curled up like a W.

“Now to just style it a bit more and...” Jessie explained as she brushed the hair with a hairbrush and cutting small bits of hair with the scissors. “...PERFECT! Your hair's the spitting image of my youth!”

Jessie was right, as Ash looked at himself in the mirror; his hair did look spot on with the photograph. He sighed again in his mind, thanking god that his ordeal was over.

“Now, where to start on the make up...” Jessie pondered, as Ash's eyes lit up into panic again, struggling to get up. Gluing fake breasts onto him and ruining his hair was one thing, but wearing girl's make up? Jessie was now diving into his limitations.

“YEOOOOOW!” The boy screamed once Jessie took off his tape gag as it stung his lips and mouth like hell.

“Ah excellent, the special tape has enlarged your lips as big as mine! With a bit of lippy, you'll have a perfect set of lips for any guy to kiss!”

Ash looked at his reflection once more; his lips had indeed grown in size, about as thick as his thumbs.

“Now hold still Twerp.” Jessie ordered as she picked out some lipstick from a draw and applied it to Ash's larger lips. He felt the lipstick rub against his lips, coating them in a darker shade of red then his hair. Ash could taste it in his mouth, tasting unpleasant to him, but he had tasted worse in his life. Seeing the transformation in the mirror, his boy looked were slowly vanishing away step by step.

“W-W-Why are you doing this to me?” Ash sobbed, almost in tears.

“Don't cry, or I can't apply your eye liner, eye shadow or mascara.” Jessie replied as she took the three spoken items from the same draw as the lipstick. Ash she spoke, Jessie applied both to her eyes. “Well, I guess you could say I always wanted a daughter. Not like a baby I have to look after and raise, but the part where the daughter's a teen and I'm like the cool mom that does stuff with her like shopping, clubbing, you know that sort of stuff.”

“But why me?”

“Revenge, it kills two birds with one stone. I get the daughter I desire and I get even with you for all the times you've humiliated me and my comrades. That, and the idea kind of evolved in my head when we dressed you up as a girl to get you into that Gym, remember that ASHLEY?”

“...Yes...” Ash sighed.

“You looked cute back then, and nooooooooow there! You looked even cuter now!”

Ash's eyes looked at their reflection. His eyelashes were now much longer and coated in the darkest black, while his eyelids were now a bright shade of purple.

“Don't you dare cry and ruin my work, or else...” Jessie threatened.

“No, no I won't...”

“Good, now let's hide those Z's of yours with some blush!”

For her next sample of make up, Jessie open a pot of blush, tipped a blush brush into it and then started to apply the blush to Ash's cheeks, which as well as reddening his cheeks and began to give him a more younger look then before, it also hide the Z's just under his eyes. Ash now looked nothing like his former self in regards to his face and hair, his reflection looking like a stranger looking back at him.

“Well you'll be pleased to know that's the last of the make up...” said Jessie.

“Oh thank god!” Ash breathed a sigh of relief.

“...so now let's get on with your Pedicure and Manicure!”  

“My what and what?”

“Your hands and feet.” Jessie explained, opening her make up box to reveal a whole range of fake artificial nails for both finger and toe nails, ranging in all different shapes, sizes and colours, and plastic tubes of lotion and moisturising cream. Squeezing out some lotion onto Ash's hand, Jessie began to massage it into his skin, giving off a more youthful and fragile look, then selecting a type of long fake finger nail and gluing each one onto Ash's real ones. Next came to nail varnish, which gave off a very strong smell to Ash, unfamiliar of this scent, as Jessie brushed the dark red onto the fake nails. The same sequence of events happened to Ash's legs and feet, only rubbed and massaged with a moisturising cream, giving him legs that looked like they were made of silk and a million dollars. Toe nails were also applied with fake toe nails, made to look more like female nails and then coated in the same coloured nail varnish.

“Okay, we're just about ready for your new wardrobe, now stand up!” Jessie ordered and Ash obeyed. Jessie then took off Ash's robe, returning him to the almost nakedness, and then made her way towards the wardrobe in the room. Ash looked at the contents as Jessie opened it up. All sorts of dresses were hung on hangers, from the very revealing to the outright embarrassing. Ash dreaded what dress would be chosen as Jessie went though each dress on the rail, but stopping on one Ash did not expect.

“Here we are!” Jessie took out a Team Rocket uniform similar to hers. “Think we'll make the great mother daughter team, don't you think?”

“You're gonna make me join Team Rocket?”

“More or less, but it's more to do the mother daughter stuff then it is doing the Team Rocket stuff.”

“Phew...”

“Now let's get you into some bra and panties!”

“BRA AND PANTIES?!?!?” Ash spoke loudly in shock. “C-Can't I wear my boxers?”

“Tut tut.” Jessie waved her finger. “Girls aren’t meant to wear boy's boxers, and no daughter of mine's gonna wear boy's things!”

“But I'm not...”   

“Do you want me to put the tape back on to shut you up? Bet you'll look really cute with even bigger enlarged lips...”

“...no Jessie.”

“No, no it's mommy or mother from now on. Understand?”

“.........yes Mother.”

“That's better. Now put these on.” Jessie threw a pair of white panties at Ash, who caught them with his hands. They were made out of Mareep cotton, feeling much softer against his fingers then Ash's normal underwear, and in the middle had a  red R, much like the Team Rocket logo.

“So, does Team Rocket actually manufacture their own underwear?” Ash asked out of curiousness as his stepping into each opening of the panties and called them up to his hips and groin.

“Not really, just comes with the uniform.” Jessie replied as she took out a large matching bra for Ash. “You might need help with this.”      

Helping Ash's arms into the bra straps, Jessie assisted Ash with hooking the back of the bra on and then positioning the fake breasts into position. Once done, apart from a bulge in the underwear, Ash was really looking the part as a girl.

“Just one more thing before we put your uniform on.” Jessie said while taking something out of the table draw.

“Oh, what's that?”

Jessie looked back at Ash with a sinister smile as she held up something she knew Ash hated the most out of girly things.

“N-No! Not the perfume!” Ash cried. “Anything but that!!”

“Oh yes, and it's the same brand from the Celedon Gym too! You'll smell of roses in ten seconds flat!”

Despite his pleas, Ash was soon engulfed in a cloud of perfume that Jessie sprayed all over him, not missing a single spot of his body. The smell was unbearable for the poor boy disguised as a girl, coughing up the perfume cloud and holding his nose. A good minute was spent spraying Ash before Jessie finally stopped.

“Now to get you dressed!” Jessie put the bottle of perfume away, and holding up a black shirt. “Since we need to hide the corset, this shirt is longer then mine. Other then that, you'll look identical to me like if I join Team Rocket many years earlier!”

After helping him put the shirt on, Jessie then helped him with the second white shirt with the familiar red R, which just like her own, was smaller then the black one. Next came the mini skirt, then long black gloves which were fingerless unlike Jessie's to show off his nails, then finally, a pair of white socks and long boots. At long last Ash's transformation was complete.

“Well, what do ya think?” Jessie laughed to herself, as she turned the funny looking boy around to show him his reflection one last time in the mirror. His response was a mix of shock and embarrassment. Not a trace of his boyhood showed anything that would give away his real gender. He looked like a girl, he smelt like a girl, and how was even feeling like a girl.

“So what....GULP!” Ash was interrupted as Jessie flicked something tablet shaped in his mouth. Almost an immediate reaction, he swallowed it. “So what...sorry so......EEK! WHAT HAVE YOU DONE TO MY VOICE?!?” No longer sounding normal, his voice was now of a higher pitch, one like a girl's voice.

“Oh you have to sound the part too you know. Now, let's take you out on the town!”

“Like this?”

“Yes like that, and you better get used to it!”

Grabbing Ash's hand like a misbehaved child, Jessie dragged her so called daughter out of the room and salon to the outside of the street. Ash felt so uncomfortable being seen like that and every person walking past them. No one seem to notice that something was off about Ash, but he was scared of what someone would think if they found him out.

Soon enough, the mother and pretend daughter arrived at a shopping busy mall. Jessie took Ash to a part of the mall where a lot of boys his age seem to hang out, not looking for Pokemon battles or such, but because they had nothing to do, the rough kind that just went through puberty and who's eyes immediately lit up once they saw Ash.

“What are we doing here?” Ash whispered.

“Testing you out.” Jessie whispered back. “If none of these boys see through you, you pass and get to stay as my daughter for as long as I see fit.”

“WHAT?!? I can't...”

“You can and you will! This is just the start, I have so many outfits and cosmetics to try out on you and buy when we go shopping together, so many Team Rocket social get togethers, and so on! Now go show those boys what you're made of!”

Jessie pushed Ash towards the boys as the surrounded him, scanning their eyes all over his body. If he felt nervous before, he was now scared to death about what could happen now.

“Hey good looking.” spoke one boy with a grin. “Nice tits.”

Ash only responded by looking down at the floor shy and depressed.

“You sure having it going nice for you huh bitch?” spoke a second. “Oooe, the things I'd do with those legs of yours.”

At this point, Ash was shaking in fear. He didn’t look up till a third boy spanked him on the ass.

“Oww!” he yelled.

“A nice round ass.” the third smiled. “You're my type a girl. Shy, scared but sexy as hell!”

Ash looked to see where Jessie was, only to see her far away sitting on a bench sipping a cup of coffee.

“Enjoying yourself, Jessica?” Jessie laughed. She wouldn’t let the boys go too far with Ash, not that the poor boy knew that, but she was enjoying his humiliation as it made her revenge all the sweeter.

“That's my daughter!” Jessie smiled, sipping her coffee. “She got her mother's looks and gets all the boys, hehheh!”

The End