A Boy and A Red Dress

Your Matt, a 16 year old orphan who lost his parents when he was 8 in a tragic accident, lived with his Aunt Lucy, a small cloth designer who loves dancing, Matt treated Lucy like his mother, they lived in a mansion with a giant garden, and a dancing room with many dancing shoes for Aunt Lucy, his grandparents were rich, so Aunt Lucy had so much money, he was homeschooled too so he didn’t have to suffer from school homework.

Matt was in his room playing video games, it was a good spring day, it was 2pm when Aunt Lucy walked in, “Hi Matt, so I have some news”, “what is it?” Matt responded, “so I have to go overseas alone for almost 4 months, so you will stay here”, “wait so I’m staying here for 4 months alone? How am I gonna cook food? I don’t know how to cook yet”, “oh don’t worry, I paid for a babysitter to come and help you while I’m away, she is really nice and sweet, I will leave at 5pm, she will come at 5:30pm, her name is Rose, please be nice to her!”, Matt nodded as a “sure” sign, “but how old is she? Am I going to deal with an old woman or something?” Matt asked, “oh don’t be silly Matt, she is 18 years old”, “ok, I have to go pack my bags”, “ok” Matt said.

It was 5pm, Matt was saying his goodbyes to Aunt Lucy at the door until she left and closed the door behind her, Matt sat in the living room thinking of how much he will miss Aunt Lucy, he did have her number so he can call her whenever he wanted, then the doorbell rang, Matt knew it was the babysitter, he came rushing to the door, trying to look good for first impression, Matt opened the door and...

No one was there, Matt took a step outside to see if there was a prankster or something, but he almost tripped on something, it was a big box, and beside it was a black suitcase, Matt read the what the box had on it, “Babysitter” was written on the box, he was completely confused on how the babysitter could possibly be inside that box, the suitcase had a paper taped to it saying “don’t open this suitcase before the box or else you will pay”, Matt didn’t know what the message meant with “pay”, he thought of paying money, and many other possibilities, Matt took both the suitcase and the box inside and walked to Aunt Lucy’s bedroom, he placed the suitcase near the bed, and sat on her bed with the box laying in front of him, “maybe I need to wait for the actual babysitter to arrive” Matt talked to himself, he waited for almost and hour, it was almost 6:50pm, and the babysitter still didn’t arrive, Matt just gave up on waiting and opened the box...he found a piece of folded paper and a...dress?
“What on earth?” Matt said, the dress was red, looked something like this ( https://my-live.slatic.net/p/c3d46f4759b221bf253c97f8eff022e9.jpg )
There was something else too, a pair of red shoes? Looked something like this ( https://ae01.alicdn.com/kf/H87ec5fc8188640be8543355c1c1547f5e/Sexy-Red-Ankle-Str... )
Matt was confused, the box said “babysitter”, but inside were a pair of red heels and dress, but there still was the folded paper, Matt slowly unfolded the paper and found some words saying “Rose, come and take care of me, feed me, clean me, and dress me as you wish, and may you be happy with my request”, Matt read the words out loud, he was even more confused, what on earth does the outfit have to do with this paper calling Rose, nothing happened at all, he thought the writing was pretty bad written by some rookie writer, it was pretty quiet until a few seconds later...

The dress started flying, taking shape of a girl, “WHAT THE-“ Matt shouted, his sentence was cut off when the shoes started to fly too, “b*tch I’m out” Matt said leaving the room running, he went downstairs to the kitchen to grab some salt, he knew that ghosts could weaken or just vanish if salt was thrown at them, he found a plastic bowl and poured in some salt from a bag filled with salt he found in a cabinet, Matt ran up the stairs, making sure he doesn’t drop ANY salt, when he made it to Aunt Lucy’s bedroom... the full outfit was standing in front of him, standing on the ground, shaped like a girl, as if some invisible girl was wearing it and standing, “say hello to my little friend, Mr.salt!” Matt shouted and threw (YEETED) the bowl at the dress, the salt had literally no effect, the bowl was just thrown at the dress and dropped, and well...the salt was everywhere, “I’m not cleaning that” a voice came from the dress, Matt just fainted on the spot after hearing that the dress just spoke.

Matt woke up, in the dancing room? On the other side he saw the dress and shoes...dancing, Matt just stared, confused, “I’m stuck with this for 4 months...great” Matt thought to himself sarcastically, the dress saw Matt and started walking towards him, Matt got up shouting “WHO ARE YOU!?”, “I’m Rose...your babysitter, your Matt right?” Rose said, “I will take care of you for these 4 months, so let’s start” Rose said in excitement, “start what?” Matt asked, “well...I only know how to take care of good girls really...”, “so what are you planning to do with me? Put me in some dress?” Matt laughed mockingly, “yes, I wanted you to wear me, but we have to do a few changes first but...I don’t know...” Rose said in a sad way that made Matt have sympathy for her, “I mean...I don’t know about wearing you, but I don’t want to make you sad” said Matt, “it’s ok, so can you wear me or no...?”, Matt was a really nice person and never liked to see someone sad or in a bad mood, “fine, I will wear you, but don’t tell anyone ok?”, “sure, but first we need to do some things” said Rose, “what do you mean?” Matt said confused by what she said, “we must get rid of that body hair and make your skin silk smooth, and we need to grow you long hair, and put you in female underwear and you will look like a girl” Rose said,”wait...so your gonna make me crossdress?”, “yes, so what do you think...or is it a b-bad idea?” Rose went from happy to sad in that sentence,”Aunt Lucy wasn’t gonna come in 4 months, I am here alone with Rose, and no one will know!” Matt thought to himself, “yes that a great idea! But please don’t tell anyone about this” Matt told Rose, “you have my promise Matt...or should I call you Mary?” Rose giggled, “but how will you make me do all of the things you listed? Growing my hair and that stuff...” Matt asked, “that’s why I have this suitcase” Rose said looking at the black suitcase that had the paper on it telling Matt to not open it, “and what’s inside it?”, “oh you will see...”, the suitcase opened, two cream bottles started flying out of the suitcase and went to Matt, followed by white underwear, “ok, put the red bottle cream on all of your hair and the white bottle cream on each part of your body, and wear the underwear” Rose said, Matt put the cream on his hair and full body, even his...thing, his boxers left Matt’s legs and the underwear put itself on him, the bra strapped around him, and the panties slid into his legs and up, “ok now wear me” Rose said, Matt looked at the pair of shoes walking towards him and rubbing themselves to his bare feet, he slid on foot inside them, then the other, the straps strapped themselves to his feet in a way he couldn’t take them off unless he cut them, then the dress was put on Matt’s body, then tightening, Matt walked to the mirrors in the room and looked at himself, “I look like an idiot” Matt said, “just wait...” Rose said while on Matt.

All of a sudden, Matt’s body hair was gone, and his skin went from dry skin to super smooth female skin, his hair grew to his upper back, “beautiful straight brown hair, I love it!” Rose exclaimed, “ then something really unexpected happened, Matt’s face was changing to a whole new shape, it became smaller, more girly, and...cute, he looked at his new face, amazed, then Matts chest got heavier, he looked down to see 2 breasts, Matt felt like he was looking at a really cute and attractive girl, Matt felt like he would get a boner but...he didn’t, his private got lighter, “oh don’t worry, I changed your entire body” said Rose, then Rose controlled the dress and the shoes, walking Matt around the room, showing Matt her control over him, “why are you controlling me?” Matt said nervously, Matt tried to break free but Rose wouldn’t let him move an inch, “now it’s time to dance Mary” said Rose,”M-Mary?” The shoes made him dance, the dress moved him around, and the panties moved his new hips and butt around, Matt’s arms were still free, he tried to take off the dress but it wouldn’t, a pair of red rubber wristbands with white hearts on them went flying at Matt, they put themselves on Matt’s wrists, they started controlling Matt’s arms while dancing, he couldn’t stop, he didn’t want to talk as he kind of...enjoyed it.

1 hour later

Matt was dancing for the past hour, dancing something close to ballet, his back hurt and so did his feet, his belly growled loud.

“You must be hungry Mary” Rose said

“Yes I’m hungry,and why are you calling me Mary?” Matt said

“Cmon don’t be so lame, have some fun for these months as a girl, we will have some good food!” Rose said in excitement

“Who will cook? You controlling me? That’s messed up honestly” Matt said

“I’m not gonna cook silly! My friend will!” Rose said

“What the-“ Matt was cut off in his sentence as Rose walked him to the kitchen, on the way a pair of white opera gloves were put on his arms and the wristbands left his hands, it felt really weird, moving not on your own will, being controlled, it was very weird for Matt, he just wanted to eat then sleep hoping he will wake up knowing that it was all a dream.

Matt made it to the kitchen and sat on a chair, he couldn’t move at all, his hands were on his laps, his new thighs were glued to each other and his feet were pinned to the floor by the heels”.

“Your such a good and polite girl!” Rose said

“You even want to make me act like a girl?” Matt said

“I told you I only deal with good girls” Rose said

Matt was terrified at what else Rose could do to him, what if he puts makeup? What if she makes him go outside? What if she makes him to inappropriate things? Matt was lost in his thought until he realized that there was...a floating maid outfit cooking, the outfit was a maid dress ( https://encrypted-tbn0.gstatic.com/images?q=tbn:ANd9GcRPq7qCaKPimFOUxWg5jkaK1hLA... ), black heels ( https://cdn.shopify.com/s/files/1/1196/3614/products/maid-21-bw.jpg?v=1571439721... ), and white knee high socks, so this is what Rose meant by “friend”, after 5 minutes of waiting the maid outfit walked toward Matt holding a plate with something on it, when she put it down in front of him, it was 2 grilled cheese sandwiches! There was ketchup on the side too! Matt was so hungry he just grabbed the first sandwich then tried to shove it into his mouth…but that’s not how a polite girl does it innit?

The gloves Matt was wearing stopped him and put the sandwich back into the plate.

“WHY?” Matt yelled

“I said you are a POLITE girl, so eat politely” Rose stated

The gloves then grabbed a fork and a knife and started cutting the sandwiches into slices, then dipping each small slice in ketchup then putting in front of Matt’s mouth, he opened his mouth and then the gloves moved his hands to eat the slice, after he finished from eating he drank 2 cups of water, “I need to sleep, this is boring” Matt said

“Well...you will sleep now then” Rose said

The maid outfit just disappeared into the hallways, and Rose walked Matt to Aunt Lucy’s bedroom, “sorry but I sleep in my bed” Matt stated

“Well you will sleep here Mary” Rose said

“This is not my bed, AND FOR THE LOVE OF GOD STOP CALLING ME MARY!” Matt said

“Oh don’t be so silly, you will sleep here Mary, that’s your name right?” Rose said

Rose left Matt’s body, he was left in the white bra and panties she put him in, then some outfit came from under the bed, Matt tried to run out of the door, but the door closed shut and locked itself, Rose has left the room before it closed, Matt looked behind him to see the outfit, it was a pair of white thigh high socks, a white mini skirt ( https://i.pinimg.com/originals/c9/8b/06/c98b06bce6d57ec30845ba5bba8b3d17.png ), and a pink crop top hoodie ( https://i.pinimg.com/originals/69/7f/5e/697f5ec7cd66f55a805ff984c5fa29d2.jpg ).

“This isn’t too bad I guess :|” Matt thought to himself

The outfit attacked Matt, he didn’t resist but just let the cloth do it’s thing, the clothing was too strong for him, he opened his eyes to see himself in a mini skirt, crop top hoodie, and thigh high socks, the socks walked him into the bathroom the skirt and the panties pulled themselves down, the socks sat Matt down on the toilet, he looked down so he can start to pee until, he realized that his “;)” has changed, Matt screamed, but no one heard it, he then tried to pee but looked away from his new “;)”, when he was done a floating tissue floated towards him and cleaned it for him, he then stood up, washed his hands, brushed his teeth then laced down on the bed, he had control of himself now, he moved freely on the bed, then falling asleep.

Note: I need a few ideas to continue this story, reply with tips or suggestion :)