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Fitting Punishment?                 by: Ashley

 

"What do you think you are doing?!!"

James froze in place knowing full well that he has been caught red-handed snooping in his sister’s room. He was afraid to turn around thinking that maybe she will just disappear. How wrong he was. Becky grabbed him by the arm and threw him on her bed. "What are you doing? Looking for my diary? Maybe some clothes to fantasize with? Or maybe even better, some clothes for you to wear? I tell you what. You want to know what it is like to wear my clothes? We will find you something really pretty to wear. We may even take a little trip to the mall so you can get more experience as a girl?"

"No that is not what I was doing? I was just looking" yelled James.

"Shut up you little sissy. Now strip those awful boy clothes. No sister of mine is going to wear such dreadful things." Becky started to take James’ T-shirt off. He knew very well he better do as she says or he may get a beating.

Becky is 17 and James is 13. At that age an older sister can do some damage to a scrawny little 13 old boy if he is not careful. Becky would constantly torment him because of his small size and his long hair. She would call him a sissy or a girl just to get him going. He would end up being the one in trouble from there mother when he would try and retaliate.

Once James was stripped Becky pulled out a matching bra and panty set in white. She forced James to put it on. She also pulled out some breast forms she had used for Halloween one year and put them into the bra.

"Why are you doing this to me?", James Asked.

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"Because you must want to be a girl. That has to be the reason you were snooping in my room. Because I know you were not spying on me or looking for my diary because you know I would kill you." Becky proceeded to look through her clothes to find something fitting for her new little sister. She pulled out a pair of jeans and white T-shirt that only cam half way down James’ body leaving his stomach open for all to see. She also put on some blue sneakers that look like a little girl’s shoes. Looking at James you could tell he was wearing his sister’s clothes. He started to cry but Becky just pushed him out the door of her bedroom and down the stairs. "We are going to the mall to do a little shopping. Once we get to the mall, we have a couple of places to stop before we can actually begin y shopping". James was scared and continued to cry. Becky yelled. "Stop that crying you little sissy. " Then Becky lightened her tone and said, " Oh, I know, you are crying because you do not have a name yet little sister? Well, how about Jamie. It is close to your boy name… But no, it is still kind of masculine and we all know that you are far from masculine. You are just the most feminine and sweet little thing aren’t you? Let’s try Missy. That is a sweet little name for my sweet little sister. Do you like you new name, Missy?"

"No. I hate it. I hate you" screamed James. "You can’t make me do this. You just can’t."

"I can make you do whatever I want. Or would you rather I tell mom that I caught you wearing my clothes. What do you think she would say to that?" James knew his mother would freak if she thought he was wearing Beck’s clothes. He settled down and sat in the front seat of Becky’s car putting.

"Now Missy. You don’t expect to sit there pouting. How do you expect to impress the boys at the mall with a face like that. Don’t you worry. We will fix that face up real pretty for you so all the boys will want to know who that pretty little girl is over there. Is that what you want?"

"I want to go home Becky." James Yelled.

Becky retorted sternly and with losing her patience, "Like I said, would you rather me tell mom you were wearing my clothes. And maybe I will tell her that it was not the first time I caught you doing it. You know she would believe e well before even thinking about believing you." Her tone softened a bit. "Now, do you want us to fix that face of yours so all the boys will notice you?"

"Fine."

"I can’t hear you. I want you to ask me nicely." Becky taunted.

"Alright. Can we fix my face up all pretty? Please?". James mocked Becky.

"Why do you want it done?"

"Oh Jeez. So all the boys will notice me." James said with a defeated tone in his voice.

"There don’t you feel better now that you have admitted you like the boys to pay attention o you and you like being a girl?"

The rest of the drive to the mall was quiet except for the few comments Becky would make about the cute boy over there or the cute boy playing ball. When they arrived at the mall Becky had to drag James(Missy) out of the car. "Either you come with me willingly or I get those boys over there to help me get my sissy brother out of the car so he can get his hair done. I am sure they would have no problem getting you out and what ever they do to you after that, I cannot stop them because I am no match for them." Missy got out of the car and looked around to see if anyone could recognize him. "Now once we get your hair and makeup done, no one would know you are a boy unless you let them now. Until then you better not cause a commotion or someone will know you are a boy wearing girl clothes."

James slowly followed Becky into the mall and to the hair salon. Becky walked up to the desk and said, "My brother here just loves long blonde hair and wants to have his hair look very feminine and cute so all the boys will notice him. He is such a sissy. Can you help him out? " This got a laugh out of the girl at the front desk and she laughed even harder when she saw Missy standing there. " He wants to be called Missy. So please let him have his wish?"

The girl walked over to Missy and said, "Missy huh? That is a very pretty name for such a pretty boy. Do you like being a pretty boy, Missy?"

Missy looked over at Becky hoping she may stop this but with the look she was giving him, he knew what his answer better be. "Yes" he said very demurely.

"Would you rather be a pretty little girl instead. You know, the ones that walk around the mall hoping all the boys will look at her and ask her out on a date?"

Missy again softly said, "I guess so."

"Well, let’s get a good look at you so we know what we can do."

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"Well aren’t you just the cutest little thing. I think we can help you out sweetie. Come this way." Missy started to run but Beck was too quick for him and grabbed him and sat him down in the seat. They quickly put a pink cape on him and tied it to the chair so Missy could not get up.

Becky stared straight into Missy’s eyes and said, "If you do not sit there like a good girl, I will tell mom how bad you were for the girl and she will have a fit about it and you would be lucky if you only get a spanking." Missy stopped fighting and sat there still through the whole ordeal. The girl started by getting a box of hair color and showing Becky a few colors. Becky finally chose one and told the girl to not let Missy see her hair or face as she is doing it. She washed the hair color into Missy’s hair and put what looked to be a shower cap over his head. Then she decided she would do his makeup for him. She started with putting a foundation on his face. She smoothed it until she was satisfied with what she had done. Next she put eye shadow on. She decided that since it was daytime, Missy should have a brown eye shadow on. "We will put this eye shadow on. IT ii called Cocoa. Just so when the boys ask you how you make your eyes so pretty. HeeHeeHee." She finished with that and put mascara on him and then lipstick. She put a brown shade to match his eyes. When she was done with his face she saw it was time to take the hair color out. She proceeded to take the shower cap thing off and then rinsed his hair. Then took him back to the chair he originally started in. The girl blew dry his hair and played around for a while until she must have been satisfied with how he, or should I say She now, looked. Missy stood up and turned to look in the mirror. Before she could get around to look, Becky grabbed her and said, "Now look at the mess you made on your shirt missy. We will have to get you a new shirt to wear. And the hair color is all over your shoes too. Get those off. Take that shirt off too. " Missy did not move but started to cry. "Now do not cry me sweet little sister. We will get you a new shirt."

The girl at the salon said, "I have a T-shirt for her to wear. I often bring extra clothes in case I get something on mine. Let me get it." The girl went into the back and brought out a white T-shirt that has ‘Angel’ on the front. " I think this shirt is perfect for your little angel of a sister because I know she is just the sweetest little angel. " Missy took the shirt and put it on. "There is nothing I can do about the shoes but there is a show store down on the right about 4 stores down.

"Thank you very much" becky said to the girl. "Now thank her for your new shirt Missy. Don’t be rude."

"Thank you, " Missy said softly.

"Thank her for th pretty shirt to wear"

"Thank you for the pretty shirt to wear." Missy said.

"And what will you hope will happen to you with this shirt on?" Becky taunted.

Missy knew what Becky wanted to hear so he swallowed hard and repeated his previous embarrassment, "Thank you for the pretty shirt to wear so the boys in the mall will notice how pretty I am."

"Good. Now lets look at you in the mirror". Becky led Missy to the mirror to get a look at herself. "Now pose like a pretty girl. Put the arm out to your side now. That’s it."

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Missy was shocked. She could not believe it. She looked like a girl. A pretty girl that looked like she was ready to cruise the mall. She started to cry.

Becky saw this and said. "What is the matter sister? Don’t you like your new look? I know. It is because you do not have any pretty clothes to go with your new look. We will make sure you get some before today is through. Or is it because you do not have a boyfriend to show off your new look to. Don’t you worry, we will take care of both before the end of today. First though we need to get you some shoes. Come on sissy." Becky accentuated that last remark to make sure everyone in the salon heard her.

They made their way to the shoe store. As Becky and Missy walked in, Becky announced the arrival of her brother the sissy. Missy’s cheeks burned with embarrassment and her eyes started to swell with tears. "Stop crying you little sissy or I will give you something to cry about." Beck said.

"Hello. My name is Tiffany. Can I help you." The girl in the shoe store said as she approached Becky and Missy.

"Becky clearly and loudly stated, "My brother here got hair color all over his pretty little sissy shoes when he was so excited to see his new look in the mirror and we need to find him a new pair. Maybe more. "

Tiffany chuckled as becky was finishing her speech. "I am sure we can find something for you that would fit your ‘New Look’. What is you name?"

Missy looked at Becky and she gave him the I will tell mother look. "Missy." He said quietly.

"Oh that is such a pretty little name. I have a little sister named Missy. Maybe you two can play sometime. " Tiffany laughed a little as she said that. Let’s see what we have for you in this section. Oh no these will not do. They are way to masculine for such a pretty little thing like you." After looking through a few boxes, tiffany pulled a pair of white sandals with four straps going across the top of the foot and a 2-inch heel. Becky liked these so they wen onto the counter to wait for the others Becky wanted to buy. In all she bought a pair of knee high boots in both black and white, a pair of sandals with one wide strap across the top in white and black. All with about a 3-inch heel. Also a pair of pink calf high boots with a 2-inch heel. This made Becky very happy to be getting all these pretty shoes for Missy. "Now Missy, you put on the white sandals that you bought first. I know they are not your favorite, but they do go the best with your outfit. Now let’s go get you some new clothes for your new look shall we sweetie?"

Just by the way she said that, Missy knew this day would be a long one.

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Becky and Missy walked through the mall until Becky saw a store she knew wold have the clothes she wanted to get for Missy. She grabbed Missy and dragged her into the store. Immediately, she saw an outfit she wanted. She ran to it and grabbed it and told Missy to try it on. Missy grudgingly took the outfit from her and went into the dressing room. Becky followed closely to make sure she put it on right. Missy undressed out of the jeans and T-shirt and started to put the new shirt on. It is a body suit replica of Sailor Saturn. Then Missy grabbed the skirt. It was the blue one that went with the body suit. This did nothing to hide Missy’s legs. Becky made her "Put on the white knee high boots… Ohhhh, that outfit is just the cutest on you. Keep that on while we look around for others." Missy knew she was in for trouble. As Missy walked out of the dressing room, she caught a glimpse of herself in the mirror.

 

 

(To be continued)

 


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